9 International Symposium on The Chemistry of

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Shafiya Biotechnology Co. Ltd. ... Bureau of International Co-operation. Chinese ...... HPLC ASSAYS FOR ISATIS INDIGOTICA FORTUNE EX. LINDL. .... HSCCC has been successfully applied to the isolation of various natural ...... The present research provides a new and efficiency strategy for the isolation of the highly.
Abstracts

9 th International Symposium on The Chemistry of Natural Compounds

Host: Xinjiang Technical Institute of Physics & Chemistry, Chinese Academy of Sciences Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan Eskisehir Anadolu University, Turkey

Organizer: Key Laboratory of Xinjiang Indigenous Medicinal Plants Resource Utilization Key Laboratory of Plant Resources and Chemistry in Arid Regions, CAS

October 16 - 19, 2011 Urumqi Xinjiang China

9th International Symposium on the Chemistry of Natural Compounds Chairman: Prof. Dr. H. A. Aisa, Urumqi, China Co-Chairman: Prof. Dr. Sh. Sh. Sagdullaev, Director ICPS, Uzbekistan Co-Chairman: Prof. Dr. K. H. C. Baser, Eskisehir, Turkey Co-Chairman: Prof. Xiao Li, Director XJIPC, CAS, China Members of the Academic Committee: Haji Akber Aisa Shamansur Sagdullaev K. Husnu Can Baser Ling-Hua Cao Abbaskhan Turaev Guo-Wei Qin Khusnutdin Shakhidoyatov Ablimiti Yili Xiao-Jiang Hao Temel Ozek Xiang-Ren Tan Firuza Tursunkhodjaeva Xu-Lei Xin Shoei-Sheng Lee Gen Li Yi Yang Qiao-Ying Lv Lan Jiang

9 th International Symposium on The Chemistry of Natural Compounds Supporting-Organization

National Natural Science Foundation of China 中 国 自 然 科 学 基 金 委 员 会

Bureau of International Co-operation Chinese Academy of Sciences

Foreign Experts Bureau of Xinjiang Uighur Autonomous Region

新疆燕山圣泉农业科技开发有限公司

Shafiya Biot echnology Co. Lt d.

9th International Symposium on the Chemistry of Natural Compounds

Abstracts THE ESSENTIAL OILS AND THEIR CONSTITUENTS - BIOLOGICAL AND BIOTECHNOLOGICAL APPLICATIONS …………………………………………………………K.H.C. Başer, F. Demirci(1) ALKALOIDS FROM MENISPERMACEAE PLANTS ………………………………………………………………………Guo-wei QIN(2) NOVEL CYTOTOXIC ORTHOESTER ELEMANOLIDE DIMERS FROM SEEDS OF VERNONIA ANTHELMINTICA ………………………………………………………………Y. Q. Liu, H. A. Aisa(4) STUDY ON GENETIC DIVERSITY OF GERMPLASM RESOURCE AND IDENTIFICATION OF INTRINSIC QUALITY FOR XINJIANG ESTATE GARLIC………………………………………………………M. Guan, J. Chen(5) LABDANE DITERPENOIDS FROM LEONOTIS LEONURUS ……………………………………H. K. Wu, D. Ferreira, C. L. Burandt Jr, et al(7) INTERACTION OF 5,6-DIMETHYL-2,3-TRI(TETRA)METHYLENETHIENO [2,3-d]PYRIMIDINE-4-ONES WITH NITRATING AGENT ………………………B. Zh. Elmuradov, Kh. A. Bozorov, Kh. M. Shakhidoyatov(8) STUDY ON CHEMICAL COMPOSITIONS AND BIOLOGICAL ACTIVITY OF CHICKPEA (CICER ARIETINUM L.) IN XINJIANG ……………………………………………A. Yili, Y. H. Gao, Q. L. Ma, et al(9) STEROIDAL COMPOSITION OF THE AERIAL PARTS OF HELLEBORUS CAUCASICUS A. BR. ………………………………T. Muzashvili, E. Kemertelidze, A. Perrone, et al(10)

STUDY ON THE ANTITUMOR CONSTITUENTS OF THE HERBS IN XINJIANG ……………………………………………J. H. Wang, G. Y. Li, J. Huang, et al(11) ONE-STEP MULTIPLE FRACTIONATION OF VOLATILE COMPOUNDS FROM ESSENTIAL OILS BY PREPARATIVE FRACTION COLLECTOR SYSTEM ………………………………………………T. Özek, G. Özek, K. H. C. Başer(13) ALKALOIDS AND OTHER LOW MOLECULAR METABOLITES OF CRAMBE GENUS PLANTS ……………………………I. I Ohunov, S. F. Aripova, Kh. M. Bobakulov,et al(14) CHINESE HERBAL MEDICINE BASED ANTIMICROBIAL AGENT SCREENING USING 1-DEOXY-D-XYLULOSE 5-PHOSPHATE REDUCTOISOMERASE AS A TARGET……………………………………………………………W. Y. Gao(16) DEVELOPMENT AND OPTIMIZATION OF HP-TLC AND HPLC ASSAYS FOR ISATIS INDIGOTICA FORTUNE EX LINDL. (ISATIDIS RADIX, BANLANGEN) …………………………………………………………G. Özek, K. H. C. Başer(18) THE ANTI-DIABETIC PROPERTIES OF TWO SESQUITERPENE LACTONES FROM CICHORIUM GLANDULOSUM …………………………………………………X. L. Xin, H. A. Aisa, J. P. Ye(19) THE CHEMICAL COMPOSITION AND ANTIOXIDANT ACTIVITY OF AVOCADO (PERSEA GRATISSIMA GAERTNER.) SEED AND LEAF ESSENTIAL OILS ………………………………………H. T. Kiyan, B. Demirci, F. Demirci, et al(20) PREPARATIVE SEPARATION AND PURIFICATION OF NATURAL COMPOUNDS FROM TRADITIONAL UIGHUR MEDICINES BY HSCCC ………………………………………………………………Y. Yang, H. A. Aisa(21) ABOUT THE PREDIABETOGENIC EFFECT OF LEMON JUICE CITRUS LIMON L. ………………………Yu. N. Nuraliev, Kh. A. Ghaniev, T. M. Zubaydova, et al(22) GC-MS ANALYSIS ON THE CHEMICAL COMPONENTS OF VOLATILE CONSTITUENTS IN COREOPSIS TINCTORIA FLOWERS ………………………………………………Alijan Abdureyim, Hayrat Sultan(24) SYNTHESIS OF CHLORACETYLIC DERIVATIVES OF PHENOLS AND THEIR USING IN AGRICULTURE ………………………A. K. Abdushukurov, N. N. Mamatkulov, A. U. Choriev(26)

NEW TRENDS IN CHEMISTRY OF NATURAL SESQUITERPENE LACTONES ……………………………………………………………………S.M. Adekenov(27) CHEMICAL COMPOSITION OF ESSENTIAL OIL FROM CO2-EXTRACT OF ARTEMISIA GLABELLA KAR. ET KIR. …………………………A.S.Adekenova,S.A. Ivassenko, R. Seidakhmetova,et al(29) CONTENTS OF PIGMENTS AND ALKALOIDS IN THE INTRODUCED PLANT CROTALARIA ALATA …………………Z. Ch. Abraeva, V. I. Akhmedjanova, N. K. Rakhimova, et al(31) NATURAL PRODUCTS FROM TRADITIONAL CHINESE MEDICINES ………………………………………………J. L. Yang, R. Wang, L. L. Liu,et al(32) DETERMINATION OF VITAMIN A IN THE CUMIN ……………………………………………………………………………G. Aider(34) ALKALOIDS OF HAPLOPHYLLUM FOLIOSUM …………………………………………………V. I. Akhmedjanova, L. Angenot(35) SYNTHESIS OF GUANIDINE CONTAINING CELLULOSE DERIVATIVES ……………………………O. R. Akhmedov, Sh. A. Shomuratov, A. S. Turaev(36) BIOLOGICALLY ACTIVE COMPOUNDS FROM SOME PLANTS OF GEORGIAN FLORA……………M. D. Alania, N. Sh. Kavtaradze, K. G. Shalashvili, et al(37) COMPARATIVE STUDY OF THE ESSENTIAL OILS OF OCIMUM BASILICUM L. CULTIVATED IN MONGOLIAN GOBI ………………………………………………………Sh. Altantsetseg, S. Shatar(39) ANTI-INFLAMMATORY

AND

ANTIOXIDANT

EFFECT

OF

TRADITIONAL

UIGHUR MEDICINE FORMULA ABNORMAL SAVDA MUNZIQ ………………………………………………………………N. Amat, H. Upur(41) THE FEATURES OF -HYDROXYSULFOXSIDE OF PINANE SERIES SYNTHESIS ………………………………A. V. Arefev, L. E. Nikitina, V. A. Startseva, et al(42) THERMODESTRUCTIVE PROPERTIES OF THE PECTIN SUBSTANCES OBTAINED USING A MICROWAVE TREATMENT …………………L. B. Azimova, M. Yu. Mukhamedjanova, L. Yu. Izotova, et al(44) ENDOGLUCANASE OF THE LOCAL STRAIN ASPERGILLUS TERREUS FUNGUS …………………………S. D. Baltabaeva,N. Sh. Berdiev,Sh. S. Olimjanov, et al(45)

SYNTHESIS, STRUCTURE, PROPERTIES AND THE USE OF ESTERS OF ORGANIC CARBONIC ACIDS WITH CARBOHYDRATES ……………………………G. T. Baramisova, A. F. Artamonov, B. J. Dzhimbaev(47) CHEMOSYSTEMATICS OF POPULATION OF KAZAKHSTAN’S SPECIES OF EPHEDRA L. ………………G. T. Baramisova, L. S. Kozhamzharova, K. N. Sarsenbaev,et al(48) ENDOGLUCANASE OF THE TRICHODERMA XORDIANUS FUNGUS ………………………N. Sh. Berdiev, Sh. S. Olimjanov, S. D. Baltabaeva, et al(49) BF3-CATALYZED ADDITION OF THIOLS TO (+)-CAMPHENE …………………………A. V. Bodrov, L. E. Nikitina, O. A. Lodochnikova, et al(51) NEW ARYLIDENEDERIVATIVES OF 5,6-PENTAMETHYLENE-2,3-TETRAMETHYLENE-THIENO[2,3-d]PYRIMIDINE-4-ONE ………………………Kh. A. Bozorov, B. Zh. Elmuradov, Kh. M. Shakhidoyatov(52) DFT STUDY ON THE INTRAMOLECULAR PROTON TRANSFER OF PYRIMIDINE DERIVATIVES …………………………………………………………………L. T. Chen, S. Zhu(54) TETRAHYDROFURAN

LIGNANS

AND

FLAVONOIDS

FROM

ARTEMISIA

ABSINTHIUM ……………………………………………………N. J. Chi, Y. Q. Liu, H. A. Aisa(55) MODELING OF SUPRAMOLECULAR COMPLEX OF GLYCYRHIZIC ACID WITH 2-AMINO-1,2,4-TRIAZOLE ……………………………………………………S. I. Dalimov, D. N. Dalimov(57) WATER-SOLUBLE COMPLEXES OF LAGOHILINA AND LAGOHIRZINA ……………………………D. N. Dalimov, A. D. Matchanov, N. L. Vypova, et al(58) PRELIMINARY CHEMICAL STUDIES ON SAMBUCUS NIGRA FRUITS GROWING IN TURKEY………………………………………H. G. Duymus, K. H. C. Baser(59) ETHERIFICATION OF PEAT IN THE PRESENCE OF SODIUM HYDROXIDE …………………………………………………M. V. Efanov, P. V. Ovchinnikov(60)

CARBOXYMETHYLATION OF PEAT IN MEDIUM PROPANOL-2 ………………………………………………………M. V. Efanov, A. A. Popova(62) CHEMICAL CONSTITUENTS OF MENTHA LONGIFOLIA FROM XINJIANG ……………………………………………Y. Eli, A. Yili, Y. Q. Liu, H. A. Aisa(63) SYNTHESIS OF NEW BIOLOGICALLY ACTIVE DERIVATIVES OF GUAIANOLIDЕS OF LUDARTIN AND ESTAFIATIN ………………………………A.E. Esenbaeva, A.S. Kishkentaeva, S.M. Adekenov(64) SYNTHESIS AND SPATIAL STRUCTURE OF 1α-CHLOR-3α,4β,10β-TRIHYDROXY -5,7α,6β(Н)-GUAI-11(13)-EN-12,6-OLIDE ………………………A.E. Esenbaeva, A.S. Kishkentaeva, B.S. Temirgaziev, et al(66) DESIGN OF PHENAZINE FRAGMENT ON THE BASE OF DIBENZO-18-CROWN-6 DERIVATIVES …………………A. K. Eshmotov, D. V. Kuznetsov, and A. K. Tashmukhamedova(67) PREPARATIVE ISOLATION AND PURIFICATION OF HIGHLY POLAR COMPOUNDS IN THE RESIDUE EXTRACTION OF OLIVE FRUIT EXTRACTED OIL BY HIGH SPEED COUNTER-CURRENT CHROMATOGRAPHY ……………………………………………………Z. F. Feng, M. R. Shi, D. L. Di(68) FLAVONOIDS RUMEX CRISPUS L. AND R. HALAСZII RECHING., GROWING IN AZERBAIJAN………………………………E. A. Garayev, I. S. Movsumov(70) EXTRACTION, PURIFICATION AND CHARACTERIZATION OF THE WATER-SOLUBLE POLYSACCHARIDES FROM CICER ARIETINUM L. ………………………………………S. Ghulamidin, G. Zhang, A. Yili, H. A. Aisa(72) RAPID IDENTIFICATION OF CHEMICAL INGREDIENTS FROM ARTEMISIA RUPESTRIS L. BY LC-QTOF -MS …………………………………………D. Y. Gu, Y. Yang, R. Abdulla, H. A. Aisa(74) SAPONINS FROM DIGITALIS CILIATA TRAUTV. AND THEIR BIOLOGICAL ACTIVITY…………………………………………………………L. N. Gvazava(75) A NEW METHOD TO ASSAY THE ACID VALUE OF LYCOPERSICIN ………………………………………………………H. J. Han, F. B. Wu, J. K. Liu(76)

LIGNAN AND SESQUITERPENE GLYCOSIDES FROM ARTEMISIA RUPESTRIS L. ………………………………………………………F. He, H. A. Aisa, H. Morita(77) CRYSTAL STRUCTURE OF N-ARYL-RUPESTONIC AMIDE ………………………………………………Y. W. He, L. H. Cao, J. Y. Zhao, et al(78) VOLATILE COMPOUNDS OF CYDONIA OBLONGA. VAR. MALIFORMIS DRIED FRUITS AND SEEDS FROM XINJIANG CHINA ………………………………………………………………H. Hopur, H. A. Aisa(79) ANTI TUMOR EFFECTS AND MECHANISM OF ZEYLENONE FROM UVARIA ACCUMINATA……………………………Y. Huang, D. Zhang, Y. H. Liao, et al(80) STUDY ON THE MOLECULAR MECHANISMS OF THE ANTITUMOR EFFECTS OF ORIDONIN VIA APOPTOSIS AND AUTOPHAGE ……………………………………………J. Huang, Y. Cheng, J. H. Wang, et al(81) RECEPTION OF POLYMERIC COMPOSITION ON THE BASIS OF POLYMALEIC ACID…………………I. A. Hudoynazarov, N. S. Normahamatov, A. S. Turaev(83) STUDY ON NUTRITIONAL COMPONENTS OF THE WHITE CORNMEAL AND ITS ANTI-OXIDATION ACTIVITY …………………………………………M. Imerhasan, S. Helil, K. Osman, et al(84) STUDY OF CHITOSAN BINDING WITH SPECIFIC DNA SITES IN THE TREATMENT OF THERMAL BURNS ………………………………………………F. Kh. Inoyatova, A. K. Baykulov(85) SESQUITERPENE LACTONES FROM SAUSSUREA INVOLUCRATA …………………………………………………X. G. Jia, M. Bolati, L. Pan, et al(87) TOXICOLOGICAL EVALUATION AQUEOUS EXTRACT OF THE GALLES OF QUERCUS INFECTORIA OLIVIER IN RODENT ……………………………………………Kasimjan, N. Amat, Mubarak, H. Upur(88) CHEMICAL CONSTITUENTS OF YUCCA GLORIOSA L. INTRODUCED IN GEORGIA………………………E. Kemertelidze, M. Benidze, A. Skhirtladze(89) PLANT POLYSACCHARIDES FOR RECEPTION OF NEW PREPARATIONS …………………………S. S. Khalikov, Kh. M. Shakhidoyatov, M. S. Khalikov(91)

SYNTHESIS OF 2-SUBSTITUTED 4-METHOXYTHIENO-[2,3-d]PYRIMIDINES …………………Kh. U. Khatamov, F. E. Saitkulov, Kh. U. Khodjaniyazov, et al(93) SESQUITERPENE LACTONES FROM RHAPONTICUM KARATAVICUM RGL. ET SCHMALH. ……………………A.S. Kishkentaeva, B.S. Temirgaziev, A.E. Esenbaeva, et al(94) ALKALOIDS OF PLANTS HAPLOPHYLLUM GRIFFITHIANUM …………………………D. R. Kodirova, H. A. Rasulova, H. M. Bobakulov, et al(96) SYNTHESIS OF 5-PRENYLOXY APIGENIN AND ITS ANTIOXIDANT ACTIVITY IN LINOLEIC ACID SYSTEM …………………………………………………Korbanjhon, B. G. Liu, Y.Y. Ou(98) HEPATOPROTECTIVE EFFECT OF CHITOSAN ……………………………M. U. Kulmanova, R. Yu. Milusheva, R. A. Sabirova(99) CHEMICAL AND ANALYTICAL INVESTIGATION OF SOME MEDICINAL PLANTS CONTAINING FLAVONOIDS ……………………………V. A. Kurkin, E. V. Avdeeva, V. B. Braslavsky, et al(100) STUDY CHEMICAL CONSTITUENTS ON LAGOTIS BREVITUBA MAXIM. …………………………………………………C. T. Li, Y. R. Suo, H. A. Aisa(101) COMPARATIVE PHYTOCHEMICAL ANALYSIS BY HPLC-MS/MS BETWEEN INFLORESCENCE AND SEEDS OF SAUSSUREA INVOLUCRATION ………………………………………………………J. R. Li, L. Liu, H. A. Aisa(102) ACTIVE COMPONENTS OF GARLIC AND CATALYTIC KINETICS OF ALLIIN/ ALLIINASE…………………………………………………X. X. Li, J. Chen(103) PRELIMINARY STUDY OF THE CHEMICAL INGREDIENTS OF CENTRAL ASIAN SEA BUCKTHORN FRUIT………………………Y. Q. Li, A. Yili, H. A. Aisa(107) CHEMICAL CONSTITUENTS FROM THE ROOT BARK OF CHINESE PLANT FOENICULUM VULGARE MILL.……………J. B. Lin, G. Sabir, H. A. Aisa(109) NATURAL BACTERIAL MAGNETOSOMES AS POTENTIAL MATERIALS USED IN MAGNETIC FLUID HYPERTHERMIA …………………………………………………R.T. Liu, J.Q. Tong, J. Liu, et al(111)

EPOXY OCTADECENOIC ESTERS FROM VERNONIA ANTHELMINTICA SEEDS ……………………………………………………Y. Q. Liu, Y. Yang, H. A. Aisa(113) EFFECT OF LUTEOLIN ON PROLIFERATION AND APOPTOSIS OF HUMAN GASTRIC CANCER CELL LINE BGC-823 IN VITRO ……………………………………………X. Y. Lu, Y. H. Li, X. W. Xiao, et al(114) RESEARCH ON ANTI-OXIDATION AND ANTI-CANCER ACTIVITIES OF BIOACTIVE COMPONENTS FROM POMEGRANATE PEELS IN VITRO ………………………………………………X. Y. Lu, Y. H. Li, H. A. Aisa, et al(115) DETERMINATION OF PUNICALAGIN AND ELLAGIC ACID IN THE PURIFIED PRODUCTS OF PUNICA GRANATUM PEEL BY RP-HPLC …………………………………………………Y.Q.Luo,Rahima,Y.Li,L.Liu,et al(116) ESTROGENIC ACTIVITY OF ISOFLAVONES EXTRACTED FROM CICER ARIETIUM L. SPROUTS ………………………………………………H. R. Ma, J. Wang, H. B. Wei,et al(118) PRODUCTION AND CHARACTERIZATION OF PROTEIN HYDROLYZATES FROM LOCAL RAW MATERIAL ……………………Sh. R.Madyarov, P. B. Usmanov, B. A.Tashmukhamedov(119) ISOLATION, CHARACTERIZATION AND STABILIZATION OF PHOSPHOLIPASE D FROM DAIKON RAPHANUS SATIVUS LONGIPINNATUS ………………………………………………………………Sh. R. Madyarov(121) ISOMERIC REFERENCE SUBSTANCES PREPARATION OF ISORHAMNETIN -3-O--D-GLUCOSYL-(61)--L-RHAMNOSIDE AND ISORHAMNETIN-3 -O--D-GALACTOSYL-(61)--L-RHAMNOSIDE FROM ALHAGI SPARSIFOLIA………………………S. Mansur, K. F. Han, A. Ayupbek, et al(123) NEW INDUCTOR OF INTERFERON ON THE BASES OF CMC AND SALICYLAMINE ………………S. A. Maulyanov, A. A. Sarimsakov, A. N. Narovlyanskiy, et al(124) MATRICARIN - SESQUITERPENE LACTONE FROM CANCRINIA DISCOIDEA (LEDEB.) POLJAK. …………………………O.V. Morozova, N.K. Zhappar, S.A. Ivassenko, et al(125)

STUDY OF THE EFFECTS OF CELLULOSE SULFATE ON THE INFECTIVITY OF TOBACCO MOSAIC VIRUS …………………B. I.Muhitdinov, N. S.Normakhamatov, Z. N.Kadyrova, et al(126) BROMINATION OF HYDROCHLORIDES OF 2,3-TRI(TETRA)METHYLENE-3, 4-DIHYDROPYRI-MIDINE-4-ONES WITH N-BROMOSUCCINIMIDE ……………N. I. Mukarramov, Kh. Z. Khakimova, Kh. U. Khodjaniyazov, et al(128) NUCLEOPHILIC SUBSTITUTION REACTIONS OF Α-OXYMETHYLIDENE-2,3,4, 10-TETRAHYDRO-1H-PYRIDO[2,1-b]QUINAZOLIN-10-ONE ……………………A. O. Nasrullaev, B. Zh. Elmuradov, Zh. E. Turdibaev, et al(129) NEW INDUCTOR OF INTERFERON ON THE BASES OF CMC AND SALICYLAMINE …………………S. A. Maulyanov, A. A. Sarimsakov, A. N. Narovlyanskiy, et al(131) ANTIVIRAL ACTIVITY OF SULFATED POLYSACCHARIDES ………………N. S. Normakhamatov, J. P. Zuo, Ye Yang, B. I. Muhitdinov, et al(132) STUDY OF ANTIVIRUS ACTIVITY OF ALKALOID STACHYDRINE FOR VIRUS OF SHEEP-POX ………Zh.S.Nurmaganbetov, E.O.Abduraimov, A.Zh.Turmukhambetov, et al(134) ALKALOID COMPOSITION OF THE CULTIVATED SPECIES DIPTHYCHOCARPUS STRICTUS…………………I. I. Ohunov, M. G/ Levkovich, S. F. Aripova,et al(135) CORRELATION OF DATA NMR 13C AND 1H SPECTROSCOPY WITH INTERNAL SULPHUR CONTAINING ALKALOIDS OF DIPPTHYCHOCARPUS STRICTUS………………I. I. Okhunov, S. F. Aripova, M. G. Levkovich, et al(137) AMIDES OF 6-NITROQUINAZOLINE-4-YL-2-THIOCARBONIC ACID – POTENTIAL BIOLOGICALLY ACTIVE COMPOUNDS ………………N. B. Pirnazarova,U. M. Yakubov,Kh. U. Khodjaniyazov, et al(140) SYNTHESIS OF SOME DERIVATIVES OF TWO MAJOR STILBENE GLYCOSIDE OF PINUS SIBIRICA BARK ………………………A. V. Pozdeeva, N. I. Komarova, A. D. Rogachev,etal(141)

ANALYSIS OF ACTIVE COMPONENTS IN NATURAL PRODUCTS WITH CAPILLARY ELECTROPHORESIS ………………………………………………S. D. Qi, H. G. Zhang, X. G. Chen(142) STUDYING OF COLLAGEN AS A HAEMOSTATIC AGENT ………………………………O. I. Radzhabov, Т. Gulyamov, A. S. Turaev, et al(144) EVODIAMINE INDUCES CELL DEATH VIA SIMULTANEOUS INSTIGATION OF APOPTOSIS AND AUTOPHAGY IN HUMAN GASTRIC ADENOCARCINOMA SGC-7901 CELLS …………………………………………………A. Rasul, B. Yu, K. Zhang, et al(145) HYPOCOAGULATORY PROPERTIES OF SULFAPORIN IN HYPERCHOLESTERO -LEMIA……………Kh. A. Rasulova, F. Kh. Inoyatova, G. M. Kutlikova, et al(146) TRANS ISOMERIZATOIN IN PROCESSING PRODUCTS OF NATURAL VEGETABLE OIL…………M. N. Raximov, J. S. Abduvaliyev, K. X. Majidov(148) ON PHARMACOLOGICAL PROPERTIES OF “ROMETIN” PREPARATION ……………………………K. Zh. Rezhepov, Kh. L. Ziyaev,D. S. Kazantseva(149) IR-SPECTROSCOPY FOR ANALYSIS AND STANDARDIZATION OF GOSSYPOL DERIVATIVES ……………………………K. Zh. Rezhepov, Kh. L. Ziyaev, A. I. Ismailov, et al(150) QUALITY CONTROL, STANDARDIZATION OF MEBAVIN AND ITS DRUG FORM …………………………………………………K. Zh. Rezhepov, Kh. L. Ziyaev(151) MEBAVIN-MEDICAL POLYMER BASED IMMUNOSUPPRESSANT …………………………………K. Zh. Rezhepov, Kh. L. Ziyaev,A. I. Ismailov(152) WATER–SOLUBLE COMPLEXES OF GOSSYPOL DERIVATIVES …………………………………………………K. Zh. Rezhepov, Kh. L. Ziyaev(153) DETERMINATION OF 6-NITRO-2,3-POLYMETHYLENE-3,4-DIHYDROQUINAZO LINE-4-ONES BY HPLC METHOD …………………I. Kh. Ruziev, N. I. Mukarramov, N. K. Mukhamadiyev, et al(154) HPTLC VERSUS TLC …………………………………………………………G. Sabir, G. E. Morlock(155)

INFLUENCE OF CHITOSAN ON THE STATE OF GASTRIC AND INTESTINAL MUCOSA IN EXPERIMENTAL HEPATITIS …………………………R. A. Sabirova, M. U. Kulmanova, R. Yu. Milusheva(157) IN CREASING THE QUALITY OF CEREALS AND CEREALS PRODUCTS WITH USAGE OF CONCENTRATE FROM BLOSSOMS OF ROSE. …………………………S. S. Saidvaliyev, A. M. Raximov, K. X. Majidov, et al(159) SYNTHESIS AND PHYSIC-CHEMICAL CHARACTERISTIC2-METHYLTHIO4H(SUBSTITUTED) AMINOQUINAZOLINES …………………………………………F. E. Saitkulov, Kh. M. Shakhidoyatov(160) MICROELEMENT COMPOSITION OF BIOLOGICALLY ACTIVE ADDITIVE Ver-Mol-2………………O. Kh. Saitmuratova , F. T. Yakubova, J. Kutliev, et al(161) NEUROPROTECTIVE AND ANTI-ISCHEMIC EFFECTS OF POLYPRENOLCONTAINING DRUG ROPREN ………………………………………………P. D. Shabanov, V. S. Soultanov(162) SUCCESSES IN THE FIELD OF PYRIMIDIN-4-ONES, CONTAINING POLYMETHYLENE CHAINS IN THE 2,3-POSITIONS ………………………………………Kh. M. Shakhidoyatov, B. Zh. Elmuradov(163) DESIGN AND SYNTHESIS OF ISOFURANODIENE DERIVATIVES …………………………………………C. Q. Shang, L. Y. Du, Y. L. Wei, et al(165) COMPLEXING PROPERTIES OF CROWN-ETHERS INDUCING A "CHANNEL" CONDUCTANCE OF THE BILAYERS ………U. T. Sharafutdinova, U. Z. Mirkhodjaev, A. K. Tashmukhamedova,et al(166) CLASSIFICATION OF PREDIABETES AT THE INTERSECTION OF MODERN MEDICINE AND THE MEDICAL SYSTEM OF IBN SINA ………………………………………………M. Y. Sharofova, Yu. N. Nuraliyev(167) THE NEW ORIGIN OF CAMPHOR AND 1,8-CINEOL (EUCALYPTOL) OF THE ESSENTIAL OILS OF SOME ARTEMISIA SPECIES FROM MONGOLIAN GOBI-DESERT…………………S. Shatar, Sh. Altantsetseg, N. Javzmaa, et al(170) HSCCC: AN APPROACH TO ISOLATION AND PURIFICATION OF THE HIGHLY POLARITY COMPONENTS FROM SPHALLEROCARPUS GRACILIS …………………………………………………M. R. Shi, Z. F. Feng, D. L. Di(172)

SYNTHESIS OF NEW HYDRAZONES OF EPIANDROSTERONE AS POTENTIALLY BIOLOGICALLY ACTIVE AGENTS ………………………M. Sikharulidze, N. Nadaraia, MegiKakhabrishvili, et al(174) DETERMINATION OF THE CONTENTS OF LUTEOLIN AND APIGENIN IN APIUM GRAVEOLEN L. BY HPLC SIMULTANEOUSLY ……………………………………………………L. Sun, L. Meng, H. Yimamu(175) SESQUITERPENE LACTONES FROM ARTEMISIA SEMIARIDA ………………………………Zh.R. Smailova, B.B. Rakhimova, S.M. Adekenov(177) INCREASING THE FOOD VALUE OF FOOD PRODUCTS WITH USAGE OF NATURAL ADDITIVES ………………………………A. A. Sultanov, N. K. Majidova, K. X. Majidov(178) INCREASING THE QUALITY AND IMPROVEMENT OF THE CHEMICAL COMPOSITION OF NATURAL OIL …………………………A. A. Sultanov, O. A. Akramov, N. K. Majidova, et al(179) CHEMICAL CONSTITUENTS OF COMPOSITE MUNZIQ ………………………………………………………………Z. Talat, H. A. Aisa(180) PHARMACOGNOSTIC IDENTIFICATION OF FERULA SYREITSCHIKOWII …………………………………………………Y. Tan, T. T. Gao, Y. Ma, et al(181) GOSSYPOL AND GOSSYPOLONE: COMPARISON OF REACTIONS WITH NUCLEOPHILES ……………………………K. Z. Tilyabaev, A. M. Yuldashev, B. T. Ibragimov(182) SYNTHESIS AND ANTITUBERCULAR ACTIVITY OF THE NEW DERIVATIVES ANABASINE ………………………………………………………R. T. Tlegenov, Karakalpak(183) CROWN-ETHERS AT THE WATER-AIR INTERFACE ………………U. B.Toyirov, U. Z. Mirkhodjaev, A. K. Tashmukhamedova,et al(184) ABSORPTION OF ANTI-ARRHYTHMIC ALKALOIDS IN THE CACO-2 MODEL ………………………………L. K. Tsiklauri, H. Hoyer, G. Chkhikvadze, et al(186) STUDY ON THE CELL MODEL OF ANTI-VITILIGO ACTIVITY OF VERNONIA ANTHELMINTICA ………………………………………A. Tuerxuntayi, Maidina, Y. Q. Liu, et al(188)

STUDY ON EXTRACTION OF FLAVONOIDS FROM DRACOEPHALUM MOLOLARIE L. AND ITS ANTIOXIDANT ACTIVITY ………………………………………………………Y. Turahun, T. Muhammad(190) ANALYSIS OF VOLATILE COMPOUNDS IN DRACOCEPHALUM HETEROPHYLLUM GROWING IN XINJIANG BY USING HS-SPME-GC-MS TECHNIQUE

……………………………………………M. Tuxun, Q. Wang, H. J. Han, et al(191) BIOLOGICALLY AND PHARMACOLOGICALLY ACTIVE ALKALOIDS FROM THE FLORA OF GEORGIA …………………………V. U.Vachnadze, L. G. Kintsurahvili, N. D. Gagua, et al(192) CHEMICAL COMPOSITION AND ANTIOXIDANT ACTIVITY OF THE ESSENTIAL OILS AND VARIOUS SOLVENT EXTRACTS FROM WILD AND CULTIVATED CARROT (DAUCUS CARROT L.) SEEDS OF XINJIANG IN CHINA ……………………………………………………Q. Wang, L. Liu, H. A. Aisa(193) ANTI TUMOR EFFECTS OF SQUAMOCIN-LOADED ELECTROSPUN FIBERS …………………………………………X. W. Wang, D. Zhang,Y. H. Liao, et al(194) PROTEIN-IMPRINTED POLYMERS GRAFTED TO FLOW THROUGH POLY (TRIMETHYLOLPROPANE TRIMETHACRYLATE) MONOLITHS ……………………………………X. H. Wang,Y. P. Huang,Z. S. Liu,et al(195) STUDY ON POLYSACCHARIDES FROM UYGUR MEDICINE DIAPHRAGMA JUGLANDIS FRUCTUS BY PHENOL-SULFURIC ACID METHOD ………………………………………………Y. Wang, R. Kasim, Aziguli, et al(196) SYNTHESIS OF 2-METHYLENE-OLEANONIC ACID AS A POTENTIAL ANTITUMOR AGENT …………………………………………………H. K. Wu, G. Li, H. H. Li, et al(197) PROBING THE MECHANISM OF DIRECT MANNICH-TYPE -METHYLENATION OF OLEANONIC ACID VIA UPLC-ESI-TOF-MS ………………………………………H. K. Wu, J. S. Zhang, D. H. Deng, et al(198)

ANTI-INFLAMMATORY ACTIVITY,ANALGESIC ACTIVITY AND CHEMICAL CONSTITUENTS OF LACTUCA SATIVA L. SEEDS ………………………………………………………………F. Xu, H. A. Aisa(199) MOLECULAR COMPLEXATION OF IVY AND LICORICE SAPONINS …………………………L. A. Yakovishin, V. I. Grishkovets, D. Yu. Belash, et al(200) "VER-MOL-2" ZINC CONTAINING NATURAL BIOLOGICALLY ACTIVE SUBSTANCES ………………………………F. T. Yakubova, O. Kh. aitmuratova, N. J. Sagdiev(201) SEPARATION OF DEHYDROVOMIFOLIOL FROM LEAVES OF NITRARIA SIBIRICA BY HIGH-SPEED COUNTER-CURRENT CHROMATOGRAPHY ………………………………………………Y. Yang, M. Bakri, D. Y. Gu, et al(202) STUDY ON THE IDENTIFICATION OF CICHORIUM GLANDULOSUM BOISS.ET HUET. AND CICHORIUM INTYBUS L.BY MULTI-STEPS INFRARED MACRO-F INGERPRINT METHOD ……………………………………………W. J. Yang, Zaynap, Marhaba, et al(203) CHEMICAL CONSTITUENTS OF ZIZIPHORA CLINOPODIOIDES …………………………………Y. H. Ye, Bahang, Y. Q. Liu, G. A. Zou, et al(205) COMPARATIVE ANALYSIS OF BIOLOGICALLY ACTIVE COMPOUNDS OF GENUS CLIMACOPTERA …………………………B. K. Yeskaliyeva, G. A. Seitimova, A. T. Kaliyev, et al(206) LIPOPHILIC COMPOSITION OF SEEDS OF SAFFLOWER “AK MAI”, GROWING IN KAZAKHSTAN ………………B. K. Yeskaliyeva, A. A. Turgumbayeva, G. Sh. Burasheva, et al(207) EXTRACTION, PURIFICATION AND CHARACTERIZATION OF THE WATERSOLUBLE POLYSACCHARIDES FROM SEED OF OCIMUM BASILICUM ……………………………………………H. Yimamu, H. A. Aisa, R. Kasimu(209) PROTECTION OF UIGUR MEDICINE CICHORIUM GLANDULOSUM EXTRACT ON TYPEⅡ DIABETES RATS …………………………………………………Y. Zhang, X. L. Xin, H. A. Aisa(210)

STUDYING ON ULTRASONIC-MICROWAVE SYNERGISTIC EXTRACTION FLAVONOIDS OF KUNLUN CHRYSANTHEMUM ………………………………………………Y. L. Zhang, A. Simayil, Y. Wang(211) ALKALOIDS OF ECHINOPS NANUS BUNGE ……………………G.T.Zharylgasina, E.E.Shults, A.Z.Turmukhambetov, et al(212) THE QUICK-MAKING METHOD OF ROSE PIGMENT ………………………………………………………B. Zhao, A. Yili, H. A. Aisa(213) SYNTHESIS AND ANTI-INFLUENZA ACTIVITY OF RUPESTONIC ACID DERIVATIVES …………………………………………………J. Y. Zhao, Y. W. He, H. A. Aisa(214) NEUROLOGICAL EFFECTS OF THE COMPOUNDS DERIVED FROM GOSSYPIUM HERBACEUM L. IN PC12 CELLS …………………………………………Y. X. Zhao, T. X. Dong, H. A. Aisa,et al(215) FATTY ACID COMPOSITION OF LIPIDS OF MICROALGAE ……………………………J. F. Ziyavitdinov, U. J. Ishimov, Sh. I. Salikhov,et al(217) PRIMARY STRUCTURE OF ACTIVE CENTER OF LIPASE FROM FUNGUS PENICILLIUM MELINII ………………………………………………J. F. Ziyavitdinov, Sh. I. Salikhov(218) CHEMICAL CONSTITUENTS FROM LEAVES OF CROTON LAEVIGATUS …………………………………………G. A. Zou, H. A. Aisa, J. S. Yang, et al(220) SCREENING OF THE ANTIBACTERIAL ACTIVITY, CYTOTOXICITY AND ANTIOXIDANT PROPERTIES OF EXTRACTS OF SOME UZBEK PLANTS ………………………S.A. Sasmakov, Zh.M. Putieva, A.M. Nigmatullaev, et al(222) LIPIDS OF CORTUSA TURKESTANICA AERIAL PART ………………………D.T. Asilbekova, F.Yu. Gazizov, A.I. Glushenkova, et al(223) CONVERSION OF SONGORINE INTO RELATED ALKALOIDS OF SOME ACONITUM SPECIES …………………………………………………B.T. Salimov, N.D. Abdullayev(224) OBTAINING DRY EXTRACT FROM PLANT GERANIUM SAXATILE ……………………D. R. Siddikov, B. M. Makhmudova, S. Z. Nishanbaev, et al(225)

SYNTHESIS OF ISOQUINOLINE ON THE BASE OF HOMOVERATRYLAMINE AND PHTALIC ACID …………………………………A. Sh. Saidov, M. Alimova, V. I. Vinogradova(227) LIPIDS OF AJUGA TURKESTANICA ……………………Sh. K. Khidoyatova, N. T. Ulchenko, S. D. Gusakova, et al(228) CHEMICAL COMPONENTS AND BIOLOGICAL ACTIVITY OF SCUTELLARIA SCHACHRISTANICA AERIAL PART ……………………Z. O. Toshmatov, K. A. Eshbakova, Kh. M. Bobakulov, et al(230) PURIFICATION OF N-METHYLCYTISINE FROM WASTES OF CYTISINE MANUFACTURE ……………………………R. A. Botirov, G. B. Sotimov, V. I. Vinogradova, et al(232) ON PHARMACOLOGY OF DITERPENE ALKALOIDS DESOXYDELCORINE, DELCORINE, DEMETHYLENEDELCORINE AND C-6-BENZOYLDELCORINE …………………F. N. Dzhakhangirov, J. Rejepov, F. M. Tursunkhodjaeva, et al(233) ON

PHARMACOLOGY

OF

DEMETHYLENEELDELIDINE,

DITERPENE

ALKALOIDS

ELDELIDINE,

C-6-ACETYLELDELIDINE

AND

C-6-BENZOYLELDELIDINE …………………F. N. Dzhakhangirov, J. Rejepov, F. M. Tursunkhodjaeva, et al(235) A NEW SECOIRIDOID GLYCOSIDE FROM FRAXINUS RAIBOCARPA ………………K. A. Eshbakova, Kh. Sh. Kamoldinov, Kh. M. Bobakulov, et al(237) IMMUNOMODULATING INFLUENCE OF ECDYSTEN IN THE TREATMENT OF GIARDIASIS IN PATIENTS WITH PULMONARY TUBERCULOSIS ……………………………………J. I. Islamova, N. A. Davis, V. N. Syrov, et al(239) EVALUATION OF PHARMACOLOGICAL PROPERTIES OF PROANTHOCYANIDINS FROM ALHAGI PSEUDALHAGI …………………………Z. A. Khushbaktova, Z. A. Kuliev, Sh. Sh. Sagdullaev(240) AJUGA TURKESTANICA AND PREPARATIONS DEVELOPED ON ITS BASIS …………………………………V. N. Syrov, F. Egamova, G. I. Ismailova, et al(241) TECHNOLOGY FOR OBTAINING SONGORINE ALKALOID FROM AERIAL PART OF ACONITUM MONTICOLA ……………………O. T. Juraev, M. N. Sultankhodjaev, Sh. Sh. Sagdullaev, et al(242)

ON ACID-WATER EXTRACTION – ULTRAFILTRATION TECHNOLOGY FOR SOME BIOLOGICALLY ACTIVE ALKALOIDS PRODUCTION FROM LOCAL PLANTS ……………………Sh. Sh. Sagdullaev, A. Z. Sadykov, M. E. Tursunova, et al(243) FEATURES

OF

PHARMAСOLOGICAL

DERIVATIVES

OF

ACTIVITY

IMPERIALINE

OF

SEMISYNTHETIC

-DIHYDRO-

AND

ISODIHYDROIMPERIALINE ……………………………………………………Yu. R. Mirzaev, R. Shakirov(244) THE ROLE OF STEROIDAL ALKALOIDS IN TREATMENT OF CIRCULATORY SYSTEM DISORDERS ……………………………………………………………………Yu. R. Mirzaev(245) WATER SOLUBLE COMPLEX OF ANTIBACTERIAL PREPARATION NITROXOLIN ……………………………………………………A. M. Khvan, R. K. Karimov(247) TRANSFORMATION ON the BASE OF NORFLUOROCURARINE ……F. X. Yuldashev, M. M. Mirsaeva, B. Tashkhodjaev, M. G. Levkovich, et al(248) FUNGICIDAL ACTIVITY OF THE ETHANOLIC EXTRACT OF FERULA FOETIDA RESIN ……………………………F. A. Mustaev, E. R. Kurbanova, A. A. Umarov, et al(250) TERPENOIDS AND FLAVONOIDS OF PLANTS OF ARTEMISIA GENUS SERIPHIDIUM (BESS.) SUBGENUS FROM FLORA OF CENTRAL ASIA ……………………………………R. F. Mukhamatkhanova, I. D. Sham’yanov(251) THE COMPOSITION OF CO2-EXTRACT OF ECHINOPS RITRO …………………………Ye. M. Suleimen, S. Machmudah, M. Yu. Ishmuratova(252) INFLUENCE OF FIVE CHINESE INSECTICIDES TO PR ENZYMES ACTIVITY OF UPLAND COTTON LEAVES …………………………………A. M. Asrorov, H. A. Aisa, O. N. Veshkurova,(254) INSECTICIDE PROPERTIES OF FRACTIONS ISOLATED FROM THE SEEDS OF MALVA SYLVESTRIS …………………………M. J. Oripovaa, E. M. Sultanovaa, Yu. I. Oshepkovaa(257)

THE INFLUENCES OF SOWING DEPTH ON SEED GERMINATION OF SAUSSUREA INVOLUCRATA KAR. ET KIR. …………………………………………………………Y. R. Chen, X. J. Wang(258) ALKYLATION OF О-CRESOL BY POLYPRENOLS ………………………………U. T. Zokirova, N. K. Khidirova, А. А. Koroleva(259) STUDYING OF BIOLOGICAL ACTIVITY OF DITERPENOID ALKALOIDS AND THEIR DERIVATIVES FROM ACONITUM KARACOLICUM ………………………………………………E. O. Terenteva, Z. S. Khashimova(260) NEUTRAL COMPONENTS OF ALCEA NUDIFLORA OF FAMILY MALVACEAE ………………………………M. J. Rakhmatova, N. K. Khidirova, T. P. Kukina(261) NEUTRAL COMPOUNDS OF GRASSY PLANT HIBISCUS L. LEAVES ……………………S. E. Kiyamova, Kh. U. Khodjaniyazov, N. K. Khidyrova(263) OBTAINING DRY EXTRACTS FROM ROOTS AND RHIZOMES OF RHODIOLA LITVINOVII ………………………F. A. Melikuziev, B. M. Makhmudova, S. Z. Nishanbaev(264) PHENOLIC COMPOUNDS OF ROOTS AND RHIZOMES OF RHODIOLA LITVINOVII …………………………F. A. Melikuziev, S. Z. Nishanbaev, Kh. M. Bobakulov (266) LIPIDS OF SOLENANTHUS TURKESTANICA FRUITS …………………………N. K. Yuldasheva, N. T. Ul’chenko, A. I. Glushenkova (268) POLYISOPRENOIDS OF RHUS CORIARIA ………………………N. M. Mamatkulova, F. A. Melikuziev, N. I. Mukarramov(269) RESEARCH OF CHRONIC TOXICITY OF DIHYDROATIZINE ALKALOID …………………………………………M. S. Kodirova, F. M. Tursunkhodjaeva(271) FLAVONOIDS FROM AERIAL PARTS OF SCUTELLARIA GUTATA ………………………………Z. O. Tashmatov, K. A. Eshbakova, J. I. Tursunov (272) THE COMPLEXES OF GLYCYRRHIZIN ACID WITH THE MEDICINAL MATERIALS NITROXOLIN, ALLAPININ, LIDOKAIN …………………………………A. M. Khvana, T. A. Azizovb, R. K. Karimova(273)

INFLUENCE OF HYDROTHERMAL PROCESSING ON THE QUALITY OF GLUTEN COMPLEX OF FLOUR ………………………………………………N. V. Korablyova, T. D. Kasimova (274) EXTRACTION OF FLAVONOIDS FROM ROOTS OF AMMOTAMNUS LEHMANNII ……………………………………………R. M. Khalilov, M. A. Mamatkhanova (275) INVESTIGATION OF PROCESS OF EXTRACTION ECDYSTEROIDS SUM FROM AERIAL PART OF SILENE BRAHUICA …………………………………………M. A. Mamatkhanova, M. R. Yakubova (276) THE

QUANTUM-CHEMICAL

ANALYSIS

OF

ANTIRADICAL ACTION

OF

GOSSYPOL AND ITS DERIVATIVES ………………………………U. G. Gayibov, B. A. Salakhutdinov, V. P. Bruskov (277) STUDY OF THE IMMUNO-STIMULATING ACTION OF PHYTOECDYSTEROIDS FROM SILENE VIRIDIFLORA …………………………………I. D. Bobaev, M. T. Alimova, S. T. Kosnazarov (278) A NEW E,Z-GERMACRANOLIDE OF ARTEMISIA BALDSHUANICA ………………………………………R. F. Mukhamatkhanov, I. D. Sham’yanov(279) FLAVONES OF ARTEMISIA BALDSHUANICA ……………………R. F. Mukhamatkhanova, I. D. Sham’yanov, S. Kh. Zakirov(280) THE FLAVONOIDS OF ARTEMISIA LEUCOTRICHA, A. LEHMANNIANA AND A. TENUISECTA ……………………R. F. Mukhamatkhanova, I. D. Sham’yanov, S. Kh. Zakirov(281) SECONDARY METABOLITES OF ARTEMISIA KORSHYNSKYI …………………I. D. Sham’yanov, B. Tashkhodzhaev, R. F. Mukhamatkhanova (282) SULPHUR-CONTAINING COMPONENTS OF FERULA FOETIDA ………………………………………………E. Kh. Khalilova, I. D. Sham’yanov(283) ALKALOIDS FROM ALHAGI SPARSIFOLIA ………………………………………G. A. Zou, S. C. Hu, S. Mansur, H. A. Aisa(284) ISOLATION OF TWO ANTIOXIDATIVE PEPTIDES FROM SEEDS OF APIUM GRAVEOLENS L. INDIGENOUS TO CHINA ………………………………………………………A. Yili, Q. L. Ma, Y. H. Gao(285)

STUDY ON ANTIOXIDANT PEPTIDES FROM THE CHICKPEA’S SPROUT OF XINJIANG CHINA …………………………………A.Yili, Q. L. Ma, Q. Y. Lv, Y. H. Gao, B. Zhao(286) FLAVONES FROM ARTEMISIA RUPESTRIS L. …………………………………………………………………F. He, H. A. Aisa(287) THE FATTY ACID COMPOSITION OF ELEVEN APIACEAE PLANT SEEDS FROM CHINA ………………………………………………………Q. Wang, L. Liu, H. A. Aisa (288) NATURAL BACTERIAL MAGNETOSOMES AS POTENTIAL MATERIALS USED IN MAGNETIC FLUID HYPERTHERMIA ………………………………………………………R.T. Liu, J. Liu, J.Q. Tong (289) ANTI TUMOR EFFECTS OF SQUAMOCIN-LOADED ELECTROSPUN FIBERS ………………………………………………X. W. Wang, D. Zhang, Y. Huang (290) ANTITUMOR ACTIVITIES AND MECHANISM OF ZEYLENONE FROM UVARIA GRANDIFLORA ROXB. …………………………………………………Y. Huang, X. W. Wang, D. Zhang(292) RAPID IDENTIFICATION OF FLAVONOID GLYCOSIDES IN PASANIA KAWAKAMII AND CYCLOBALANOPSIS MORII VIA HPLC/MS AND HPLC-SPE-NMR. ……………………………………………………………C. C. Chang, S. S. Lee(293) A NEW LIGNAN FROM THE ROOTS OF STELLERA CHAMAEJASME. ………………………………………………L. P. Liu, X. Y. Wang, H. B. Wang(294) THREE NEW FLAVONES FROM FLOWERS OF GARDENIA JASMINOIDES. ………………………………………………………………G. W. Qin, Z. Y. Fan(295) A NEW FUROSTANOL GLYCOSIDE WITH FATTY ACID SYNTHASE INHIBITORY ACTIVITY FROM OPHIOPOGON JAPONICAS (THUNB.) KER-GAWL ……………………………………………………C. L. Duan, Y. Wang, X. F. Ma(296) A NOVEL C29 STEROL FROM CLERODENDRUM CYRTOPHYLLUM TURZ. ………………………………………………………P. Wang, F. J. Guo, J. J. Tan (297) A NEW TIGLIANE-TYPE DITERPENE ESTER FROM WIKSTROEMIA SCYTOPHYLLA DIELS.

………………………………………………H. Z. Jiang, Q. Y. Ma, S. Z. Huang (298) A FACILE SEMISYNTHESIS of 2,7-BISACETYLTAXOL FROM 10-DAB ………………………………………………M. Gu, Y. M. Zhang, W. Luo, W. Lu(299) BRIEF INTRODUCTION OF THE KEY LABORATORY OF XINJIANG INDIGENOUS MEDICINAL PLANTS RESOURCE UTILIZATION ……………………………………………………………………………………(300)

9th

International

Symposium

on The

Chemistry

of Natural

Compounds

THE ESSENTIAL OILS AND THEIR CONSTITUENTS BIOLOGICAL AND BIOTECHNOLOGICAL APPLICATIONS K.H.C. Başer a,b,* , F. Demircib a

King Saud University, College of Science, Botany and Microbiology Department, 11451-Riyadh, Saudi Arabia. b

Anadolu University, Faculty of Pharmacy, Department of Pharmacognosy, 26470-Eskişehir, Turkey. * [email protected]

The essential oils comprise an indispensible rich and diverse biosource for natural flavors and fragrances since centuries in various fields application an usage (1, 2). Comprehensive and systematic research on the chemical compositions of a selection of essential oils from various sources showed the wide spectrum of value added applications during our studies (3). Biological, pharmacological, agricultural, veterinary and biotechnological usages with the emphasis on the biotechnological utilization such as the biotransformation of Origanum, Nigella, Schinus essential oils and their constituens from Turkey will be presented and discussed. REFERENCES 1.

K.H.C. Başer and G. Buchbauer (Eds.) Handbook of Essential Oils: Science, Technology and Applications, CRC Press, Boca Raton, London, New York (2010).

2.

K.H.C Başer and F. Demirci, Essential Oils, Kirk-Othmer Encyclopedia of Chemical Technology, 4th Ed., Wiley, 1–37 (2011).

3.

K.H.C. Başer, Personal Website and list of publications, http://www.khcbaser.com/english/index.htm

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(accessed September 2011)

9th

International

Symposium

on The

Chemistry

of Natural

Compounds

ALKALOIDS FROM MENISPERMACEAE PLANTS Guo-wei QIN Shanghai Institute of Materai Medica, Chinese Academy of Sciences, Shanghai 201203, China Alkaloid is a large group in natural products with diversity of structural types and biological activities. The family Menispermaceae is rich in alkaloids with chemical diversity and great medical importance. According to literature survey, there are 72 genera and about 4000 species in Menispermaceae family distributed in the world. Among them, 19 genera and about 70 species grow in China. Recently we have investigated three Menispermaceae plants: Menispermum dauricum, Sinomenium acutumn and Stephania epigaea. A variety of new and known alkaloids including morphinane, oxoisoaporphine, acutumine and bisbenzylisoquinoline derivatives have been isolated and characterized. They have been screened for cytotoxicity and memory-enhancing activities in vitro and in vivo. The species Stephania epigaea is an herbaceous liana, tubers of which are used as folk medicine to treat fever, inflammation, sedation and acesodyne. During our study on the plant tubers, six known alkaloids including four bisbenzylquinolines: (+)-cepharanthine (1), cycleanine (2), (-)-norcycleanine (3), isochondodendrine (4) and two hasubananes: delavaine (5) and runanine (6) have been isolated and showed cytotoxicity against several tumor cell lines. The rhizome of Menispermum dauricum is a traditional Chinese medicine recorded in Chinese Pharmacopoeia as an analgesic and antipyretic. In our recent study, three new morphinane alkaloid dimers, 2,2-disinomenine (7), 7,8-dihydro-1,1-disinomenine (8), 9,16-N-oxide-1,1,5,5-disinomenine

(9),

together

with

two

known

alkaloids,

1,1-disinomenine (10) and sinomenine N-oxide (11) were isolated from the plant stems. Their structures were elucidated on the basis of spectroscopic methods. The absolute configuration of new alkaloids was determined by direct comparison of their CD spectra with known alkaloid sinomenine (12). All the isolated alkaloids were tested in cytotoxic assay against A549, P388 and Hela cell lines. Only 7 and 10 showed weak inhibition against A549 and Hela cell lines.

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Compounds

In the course of our study on plants Menispermum dauricum and Sinomenium acutumn, acutumine,

a

minor

morphinane

chlorine-containing

alkaloid

showed

mnemocognition-facilitating properties in three animal models (Morris water maze test in mouse, social recognition in Wistar rats and object recognition in Wistar rats). The structure modification of acutumine has been carried out. Some derivatives showed better effects than original compound in animal tests. Above results revealed that acutumine is promising lead for developing anti-Alzheimer’s diseases drugs. However, the resource of acutumine is limited due to low yield in the plant. REFERENCES 1.

B. W. Yu, G. W. Qin, et al. Phytochemistry 61, 439 (2002).

2.

B. W. Yu, G. W. Qin, et al. J. Natura Products 64, 968 (2001).

3.

H. Z. Jin, G. W. Qin, et al. J. Chinese Natural Medicines 5, 35 (2007).

4.

H. Z. Jin, G. W. Qin, et al. J. Chinese Natural Medicines 5, 112 (2007).

5.

G. H. Bao, G. W. Qin, et al. J. Natura Products 68, 1128 (2005).

6.

G. H. Bao, G. W. Qin, et al. Tetrahedron Letters 50, 4375 (2009).

7.

H. Z. Jin, G. W. Qin, et al. J. Natura Products 71, 127 (2008).

8.

B. W. Yu, G. W. Qin, et al. J. Chinese Natural Medicines 9, 249 (2011).

9.

J. Y. Chen, G. W. Qin, et al. J. Asian Natural Products Research (in press).

· 3 ·

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of Natural

Compounds

NOVEL CYTOTOXIC ORTHOESTER ELEMANOLIDE DIMERS FROM SEEDS OF VERNONIA ANTHELMINTICA Y. Q. Liu,

H. A. Aisa

Key Laboratory of Plants Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, Xinjiang, China Vernonia anthelmintica (L.) Willd., an annual herb plant of Asteraceae family, is used as traditional Uighur medicine for the treatment of skin diseases for several centuries. In our sustained investigation for structurally unique and biogenetically interesting anti-tumor agents from traditional Uighur medicinal plants in Xinjiang, China, two novel orthoester elemanolide dimmers, Vernodalidimer A (0.2 mg) and B (0.5 mg) were isolated from Chloroform extract of V. anthelmintica seeds. Their structures were elucidated by HR-MS, 2D NMR and CD spectrum. Vernodalidimer A and B showed potent inhibition against HL 60 cells (IC50 720 and 470 nM, respectively). Acknowledgements: This work was funded by the China National Founds for Distinguished Young Scientists (Grant No. 30925045).

· 4 ·

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of Natural

Compounds

STUDY ON GENETIC DIVERSITY OF GERMPLASM RESOURCE AND IDENTIFICATION OF INTRINSIC QUALITY FOR XINJIANG ESTATE GARLIC M. Guan1,2, 1

J. Chen1,3

Xinjiang Medical University, College of Pharmacy, Urumqi 830053, China; 2 Xinjiang Normal University, College of Chemistry and Chemical Engineering, Urumqi 830054, China;3 Xinjiang Ai Le Xin Pharmaceutical Co., Ltd., Urumqi 830011, China Central Asia, including China's Xinjiang Tien-shan Mountains region was the origin of

garlic. Xinjiang was located in Central Asia, the medicinal active ingredients of its estate garlic was high, which was called “Maximum-Alliin Garlic” in the international community and was the advantageous medicinal plant resources for developing drugs, health products and food supplements. At present, the study on genetic diversity of germplasm resource and identification and evaluation of advantageous germplasm for Xinjiang estate garlic had not been in depth. In this study, the garlic samples were collected from the different populations in Xinjiang and part inland traditional planting provinces for the study and the following work in two areas were finished. Firstly, based on the local origin of multi-genetic germplasm, RAPD molecular markers were used to study genetic diversity of Xinjiang estate garlic germplasm resource, in order to clarify the kinship between Xinjiang estate garlic and inland provinces garlic and the kinship within garlic of Xinjiang different populations.The results showed that 24 varieties of garlic were clustered into two groups, Xinjiang estate garlic samples were groupⅠ, while the outside samples were group Ⅱ, within two groups, varieties can be divided into five categories. The first category came from the northern region in Xinjiang, content of alliin was common; the second category came from the main southern region in Xinjiang, content of alliin was the highest; the third category came from the southern region in Xinjiang, content of alliin was high; the fourth category came from east in Xinjiang, content of alliin was low; the fifth category was samples mainly from outside of Xinjiang. The speculation for the evolution of garlic germplasm resource in Xinjiang was following: the garlic was origin from the southern in Xinjiang and firstly introduced into the northern and the eastern in Xinjiang, and then introduced into the inland provinces of China. AHeQi which was the · 5 ·

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Compounds

closest location to Central Asia may be the origin of the Xinjiang region garlic. Secondly, high performance liquid chromatography, high performance thin layer chromatography, infrared spectroscopy and other modern instrumental analysis techniques were used to identify the intrinsic quality of garlic germplasm resources, in order to compare quality of garlic germplasm from different sources. The results showed that medicinal ingredients in different sources of garlic germplasm were significantly different, the content of medicinal active ingredient from garlic in Xinjiang Wushi County and AHeQi County were higher than the garlic samples of other outside provinces of Xinjiang and other parts in Xinjiang, and diverse differentiation results showed that garlic samples can be classified into four categories, Xinjiang Tienshan Mountains was the basic foundation for the differentiation, the differentiation pattern was following :the samples from south of Tianshan Mountains were clustered into one category, the samples from north or east of Tianshan Mountains were clustered into one category, and samples of outside of Xinjiang formed a cluster, which maintain farer distance from the samples in Xinjiang. This result was consistent with the result of determination of medicinal active ingredients and RAPD molecular markers analysis of genetic diversity analysis. The above results indicated that the classification of garlic from different sources, whether genomic DNA-based classification of genetic information or content and proportion of medicinal ingredients-based classification of intrinsic quality identification, was related to the geographic area where garlic samples grew, and the main factors which had effects on the differentiation and clustering of samples were the geographical and environmental factor. This study established the biological methods and chemical methods for identification and evaluation of garlic germplasm resource, and provided not only a case for theory of identification and evaluation for medicinal plant germplasm but also the basis for the GAP standardization cultivation, good breeding and protection of germplasm resources for the advantageous medicinal garlic in Xinjiang, and laid foundation for promotion of medicinal garlic industry.

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of Natural

Compounds

LABDANE DITERPENOIDS FROM LEONOTIS LEONURUS H. K. Wua,b,

D. Ferreiraa, C. L. Burandt Jra,

J. K. Zjawionya

a

Department of Pharmacognosy, University of Mississippi, University, MS 38677-1848, USA. Tel: +1 662 915 7290. E-mail: [email protected] b College of Chemistry and Chemical Engineering, Anyang Normal University, Anyang 455002, P. R. China. Tel: +86 151 372 38927. E-mail: [email protected]

Leonotis leonurus L. (Lamiaceae), also known as Lion's Tail or Wild Dagga, is common in Southern Africa, and is used to treat fevers, headaches, dysentery, flu, chest infections, epilepsy, constipation, delayed menstruation, intestinal worms, spider bites, scorpion stings, hypertension, and snake bites[1]. In our study, eight new labdane diterpenoids, leoleorins A-G (1-8), and the known compounds leoleorins H-J (9-11), were isolated from the leaves of L. leonurus. The absolute configurations of 1 and 9 were confirmed by X-ray crystallographic analyses. Other compounds were elucidated by 1D and 2D NMR, HR-ESI-MS, as well as by comparison with our previously reported data of diterpenes from Leonurus sibiricus[2]. All pure isolates revealed the bioactivity in vitro.

O

OCOCH3 H O O REFERENCES 1. 2.

M. Iwarsson. Flora of Southern Africa 28; Botanical Research Institute: Pretoria,; p. 31-37 (1985). H.-K. Wu, F. R. Fronczek, D. Ferreira, C. L. Burandt, Jr, J. K. Zjawiony. J. Nat. Prod. 74, 831-836 (2011). · 7 ·

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of Natural

Compounds

INTERACTION OF 5,6-DIMETHYL-2,3-TRI(TETRA)METHYLENETHIENO [2,3-d]PYRIMIDINE-4-ONES WITH NITRATING AGENT B. Zh. Elmuradov, Kh. A. Bozorov,

Kh. M. Shakhidoyatov

Institute of the Chemistry of Plant Substances, Academy of Sciences, Republic of Uzbekistan, Mirzo Ulugbek Str., 77, Tashkent; Fax: 998-71-120-64-75; E-mail: [email protected] Earlier

we

have

studied

thieno[2,3-d]pyrimidine-4-ones



interaction

of

bicycle

analogies

of

2-oxo(thioxo)-5,6-dimethylthieno[2,3-d]pyrimidine-

4-ones with nitrating agent and are found, that they are exposed electrophile ipso-replacement of one methyl or both methyl groups [1]. We have shown, that as against it the tricycle thieno[2,3-d]pyrimidine-4-ones (1,2) in simulated condition do not enter this reaction, and there is an oxidation methyl groups at C-5 to

a

carboxyl

group

to

formation

of

5-carboxy-6-methyl-2,3-tri-,

-tetramethylene-3,4-dihydrothieno[2,3-d]pyrimidine-4-ones (3,4). A ratio 1,2:nitrating agent does not render essential influence on process since use of ratio 1:1, 1:2, 1:4 yields identical results: O

O HOOC

H 3C H 3C

Thus,

it

N S

is

(CH2)n

H 3C

N 1, n=1 2, n=2

shown,

N

H2SO4+HNO3

that

interaction

S

(CH2)n

N 3, n=1 4, n=2

of

5,6-dimethyl-2,3-tri-,

-tetramethylene-3,4-dihydrothieno[2,3-d]pyrimidine-4-ones with nitrating agent proceeds selective oxidation of methyl group at C-5 to corresponding carboxylic acids (3, 4). REFERANCE 1. M. Shodiev, B. A. Urakov, N. I. Mukarramov, Kh. M. Shakhidoyatov. Chem. Heterocycl. Compd. 29, 1358 (1993).

· 8 ·

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Compounds

STUDY ON CHEMICAL COMPOSITIONS AND BIOLOGICAL ACTIVITY OF CHICKPEA (CICER ARIETINUM L.) IN XINJIANG A. Yili, Y. H. Gao ,

Q. L. Ma, Z. Cheng, X. L. Xin,

H. A. Aisa

Xinjiang Key Laboratory of Plant Resources and Natural Products Chemistry, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China. [email protected] Union Laboratories of Bioactive Ingredients of Edible Plants from Central Asia, Chickpea (Cicer arietinum L.) as a Uighur traditional medicine has been grown in Xinjiang of China for nearly 2,500 years and used to treat bronchitis, diabetes and hyperlipemia as well as used for health food in Chinese Uighur prescription. Currently, limited data were available regarding to the material bases as well as mechanisms of anti-diabetes and hyperlipemia activity of Cicer arietinum L. In this paper, the anti-diabetes extract of Cicer arietinum L. was selected after comparison study of hyperlipemia activity of interesting extracts from the chickpea and enriching technology by Macroporous resin being set up. At the same time, the saponin mixture was prepared from the n-butanol fraction and hyperglycemia activity evaluated in vitro, the result shoves that concentration at 500 ppm inhibition activity of PTP1B by 100% and with IC50 of 43.21 ppm, the elucidation chemical compositions of saponin mixture is undergoing. By this works, at least eleven compounds isolated and structures of them were identified, the four isoflavones were prepared from the seeds and sprouts of chickpea by high-speed countercurrent chromatography (HSCCC). According to the above results, we have developed serials functional food products that possess anti-diabetes and hyperlipemia effective. Based on these work, we have established quality standards of chickpeas. Acknowledgements: This work was financially supported by grant (code: KGCX2-YW-503) from Key Project of Knowledge Innovation Program of Chinese Academy of Sciences and grant of 973 pre-research project of "The Study of Components of Two Edible Plants for cancer chemoprevention in Xinjiang".

· 9 ·

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of Natural

Compounds

STEROIDAL COMPOSITION OF THE AERIAL PARTS OF HELLEBORUS CAUCASICUS A. BR. T. Muzashvili1, 1

E. Kemertelidze1, A. Perrone2,

S. Piacente2

Kutateladze Institute of Pharmacochemistry, 36 P. Sarajishvili str.,0159, Tbilisi, Georgia 2

Dipartimento di Scienze Farmaceutiche e Biomediche, via Ponte Don Melillo, 84084 Fisciano, Salerno, Italy, E-mail: [email protected]

Neutral lipids have been obtained from the underground parts of Caucasian endemic plant widely distributed in Georgia - Helleborus caucasicus A. Br. (yield 14-15%). They differ from the typical vegetable fats by unusual low content of triacylglycerids(4-5%) and high content of free fatty acids(70%). The specific inhibitory activity of the aforementioned lipids against the malignant tumors has been reported[1]. Bufadienolides, an ecdysteroid, polyhydroxy and polyunsaturated spiro- and furostanol saponins including the acetylated and sulfated glycosides have been isolated from crude extract of underground parts of H. caucasicus A. Br. The sum of steroids revealed anti-tumor activity against the human lung cancer (A-549) and colorectal cancer (DLD-1) cell lines in a very low concentrations[2,3]. Arial parts of H. caucasicus are richer in steroids than roots and rhizomes. Bufadienolide glycoside, 20-hydroxyecdysone and its glucoside have been isolated from ethylacetate fractions of flowers and seeds. 20 steroidal compounds have been obtained from buthanolic extract of leaves by the CC and HPLC: a bufadienolide, an ecdysteroid, steroidal saponins, among them 9 new 5-polyhydroxy aglycones’ derivative furostanol glycosides Caucasicosides E-M. The structures of the individual compounds were unambiguously elucidated by 1D- and 2D NMR experiments including 1H-1H (COSY, 1D-TOCSY) and 1

H-13C (HSQC, HMBC) spectroscopy.

REFERENCES 1.

Ts. M. Dalakishvili, E. P. Kemertelidze, M. D. Gedevanishvili, I. G. Andguladze, V. G. Tsitsishvili. Chem. Pharm. J. 1, 146-148 (1990).

2.

C. Bassarello, T. Muzashvili, A. et al. Phytochemistry 69, 1227-1233 (2008).

3.

T. Muzashvili, A. Skhirtladze, Ts. Sulakvelidze, M. Benidze, V. Mshvildadze, J. Legault, A. Picette, E. Kemertelidze. Georgian Chem. J. 6(6), 684-685 (2006). · 10 ·

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Compounds

STUDY ON THE ANTITUMOR CONSTITUENTS OF THE HERBS IN XINJIANG J. H. Wang1, 2, G. Y. Li1, J. Huang2, S. Shen2, K. Zhang1, L. Yang1, H. Y. Gao1, M. M. Lou1, H. Y. Han1, X. Y. Li1, Q. D. Ma1,Y. Wang1, S. Xie1, R. Li1, J. B. Gao1, H. Meng2, J. X. Zhang2, C. Zhang2 1 2

School of Pharmacy, Shihezi University, Shihezi 832003, China;

School of Traditional Chinese Medicine, Shenyang Pharmaceutical University, Shenyang 110016, China Since cancer is the fatal disease that threats the health of human being, it is very urgent

to discover new effective antitumor drugs with low mammalian toxicity. Xinjiang, abundant in medicine resource, possessed advantageous traditional Chinese herbal medicine. By means of modern extraction and purification method in combination with high throughput screening, more than 20 Xinjing Traditional Chinese herbal Medicine, used in clinical for treatment of cancer, were investigated to discover their anticancer constituents, such as Fritillaria pallidiflora Schrenk, Ferula spp, Sophora alopecuroides L, Arnebia euchroma ( Royle ) Johnst., Lithospermum erythrorhizon Sieb. et Zucc, Veratrum nigrum L., Euphorbia rapulum Kar. et Kir, Coreopsis tinctoria Nutt, Trachyspermum ammi (L.) Sprague, Pleurotus ferulae Lanzi, Cynomorium songaricum Rupr., and so on. F. pallidiflora, mainly distributed in Xinjiang, was one of the well-known traditional Chinese herbal medicines, and had been used in Chinese folklore for hundreds of years. In its antitumor effective parts, Three new steroidal Saponins, pallidifloside A (1), pallidifloside B (2) and pallidifloside C (3) have been isolated from the dry bulbs of F. Pallidiflora Schrenk..

Their

structures

were

elucidated

26-O-β-D-glucopyranosyl-(25R)-furosta-5,20(22)-diene-3β,26-diol rhamnopyranosyl-4-O-β-D-xylopyranosyl]-β-D-glucopyranoside

as

3-O-[2-O-α-L(1);

26-O-β-D-

glucopyranosyl-3β,26-dihydroxyl-20,22-seco-25(R)-furost-5-ene-20,22-dione 3-O-[2-O-α-L-rhamnopyranosyl]-β-D-glucopyranoside 5-ene-3β,17α-diol

(2)

and

3-O-[4-O-β-D-glucopyranosyl]-β-D-galactopyranoside

(25R)-spirost(3)

by

spectroscopic techniques and chemical methods. In the further investigation of their antitumor effects, it was found that the three compounds showed the cytotoxicity in tumor · 11 ·

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Compounds

cells to a different degree. And the mechanisms underlying their antitumor effects were still in our investigation. R2O

21 20

22

18

23

26 25

24

27

O 19

R1O 3

R1=β-D-Glc

2

5

6

α-L-Rha

R2=β-D-Glc

4 1

I H HO

+ N

O O

(3) R1=β-D-Glc

2

I-

α-L-Rha

R2=β-D-Glc

2

HO HO

(4)

R1=β-D-Gal

+

N I-

O

4

O β-D-Glc

3

Figure 1. The structures of compounds 1, 2 and 3

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Compounds

ONE-STEP MULTIPLE FRACTIONATION OF VOLATILE COMPOUNDS FROM ESSENTIAL OILS BY PREPARATIVE FRACTION COLLECTOR SYSTEM T. Özek1, G. Özek1, K. H. C. Başer2 1

Department of Pharmacognosy, Faculty of Pharmacy, Anadolu University, 26470, Eskisehir, Turkey

2

Department of Botany and Microbiology, King Saud University, College of Science, 11451 Riyadh, Saudi Arabia The separation of small amount of pure volatile compounds from essential oils is a

matter of great importance. Besides different isolation techniques, high efficiency, sensitivity and speed of separation are important advantages for the separation of volatiles by preparative capillary gas chromatography. Due to the enormous separation power of capillary gas chromatography, the target analytes can be efficiently separated from the constituents of interest or contaminants. The aim of our studies was one-step multiple isolation of volatile compounds and optimization of fractionation parameters. Within the scope of our present study, we isolated terpenes from selected essential oils with high purity ranging from 95 to 99% by Preparative Fraction Collector (PFC) system connected to gas chromatography equipped with FID and MS detectors. This system allowed us to separate and recover sufficient quantities of individual target terpenes. Acknowledgements: The authors would like to thank TUBITAK (Turkey, TBAG project 107T498) and Anadolu University (BAP Project 090322) for financial support.

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ALKALOIDS AND OTHER LOW MOLECULAR METABOLITES OF CRAMBE GENUS PLANTS I. I Ohunov, S. F. Aripova, Kh. M. Bobakulov, N. D. Abdullaev, V. U. Khujaev The Institute of the Chemistry of Plant Substances named after Academician of S. Yu. Yunusov, Academy of Sciences, 100170, Tashkent, Republic of Uzbekistan, Fax (99871) 120 64 E-mail: [email protected] We have studied alkaloids and other low molecular metabolites of two Crambe species – C. kotschyana Boiss and C. orientalis L. (C. amabilis Butk. et Majlun) growing in Uzbekistan. Alkaloids of this genus have not studied earlier. We revealed the presence of alkaloids in these species. Chemical composition of C. kotschyana has not studied before. The chloroform extraction of alkaloids sum was subjected to chromatographic separation on silica gel. Four fractions were treated with alkaline solution after isolations of the tertiary basis with ethyl acetate and n-buthanol, and also drying of remained alkaline solution up to the dry matter then were subjected to chromato-mass-spectral analysis. From the sum of alkaloids, along with Goitrine (retention times, RT) 17.875; mass-spectrum: m/z 129 (Μ+), 102, 85, 68, 51, two compounds were obtained: 3-methyldodecane (RT-7.99; mass-spectrum: m/z 184 (Μ+) and tetradecyliodide (RT-8.89; mass-spectrum: m/z 324 (Μ+). From the sum of n-butanol fraction four neutral compounds were founded: methyl ester of oleinic acid, (RT-15.33; mass-spectrum: m/z 296 (Μ+), methyl ester of palmitinic acid (RT-13.98; mass-spectrum: m/z 270 (Μ+), 1,3-dimethoxybutane (RT-8.66; mass-spectrum: m/z 118 (Μ+). In the third fraction two compounds were founded: N-methyl-aminoheptane (RT-15.77; mass-spectrum: m/z 128 (Μ+ -1) and 5-hydroxymethyl-2-formylfurane (RT-7.99; mass-spectrum: m/z 126 (Μ+), 5-methylfuran-2-carboxyaldehyde (RT-4.33; mass-spectrum: m/z 110 (Μ+). The fourth fraction

was

obtained

from alkaline

solution

by treating with

ethyl

acetate.

Chromato-mass-spectral analysis showed possible presence of two compounds – 2,3-dihydrobenzofurane and methyl(2-methylcyclopropyl)sulfane with retention times 6.595; mass-spectrum: m/z

120 (Μ+) and RT-27.337; mass-spectrum: m/z 102 (Μ+)

respectively.

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Compounds

From the C. orientalis collected from Tashkent Province 0.06% sum of alkaloids have been isolated using 85% ethanol. Chromatographic separation of this sum on silica gel column lead to two known oily alkaloids – goitrine and goitridine. The chloroform sum was subjected to chromato-mass-spectral analysis. The basic component of the latter was 1-buten-4-isothiocyanate (allyl isothiocyanate) with RT 4.586 (mass-spectrum: m/z 113 (Μ+), 86 (13%), 72 (100%), 55 (23%)). It is revealed presence of hydrocarbons n-undecane with RT-6.76; mass-spectrum: m/z 156 (Μ+, 8%) and 2-methoxyhexene-2 (RT 10.83; mass-spectrum: m/z 114 (Μ+, 15%), 85 (100%), 70 (10%), 55 (83%), 41 (22%). According to chromato-mass-spectral analysis the alkaline solution after separating the sum of tertiary bases has the main component, identified as N-ethyl-pyrrolidine-2-one (RT 6.263 (mass-spectrum: m/z 113 (85%), 98 (100%), 84 (34%), 70 (47%), 58 (76%), after hydrolysis with 5% H2SO4 in the it gave methylisocyanate (RT 4.107; mass-spectrum: m/z 57 (100%, Μ+). Ethanolic extract of the plant was fractioned by benzene, chloroform, ethyl acetate and n-butanol and fractions were subjected to chromato-mass – spectral analysis. Chloroform fraction contained 1-butene-4-isothiocyanate (RT 4.614; mass-spectrum: m/z 113 (Μ+), 85, 72 (100%), 55); hydrocarbon – n-undecane (RT 6.789; mass-spectrum: m/z 156 (Μ+); 1-(ethyl-sulfinyl)-1,3-butadiene (RT 10.834; mass-spectrum: m/z 130 (Μ+, 12%), 114 (30%), 85 (100%), 71 (3%), 57 (18%); 5-isopropylidene-3-hydroxy-4-(2′-methoxypropionyl)2-furanone (RT 24.069; mass-spectrum: m/z 210 (Μ+ 28%), 182 (46%), 153 (32%), 124 (19%),

95

(52%),

70

(100%).

In

ethyl

acetate

fraction

presence

of

+

1-butene-4-isothiocyanate (RT 4.609; mass-spectrum: m/z 113 (Μ ), hydrocarbone n-undecane (RT 6.78; mass-spectrum: m/z 156 (Μ+), 2-methoxyhexene-2 (C7H14O) (RT 10.829; mass-spectrum: m/z 114 (Μ+, 15%), 85 (100%), 70 (10%), 55 (83%), 41 (22%), 3-methoxy-4-hydroxyvinylbenzene (RT 12.168; mass-spectrum: m/z 150 (Μ+, 100%), 135 (75%), 107 (33%), 77 (27%), 53 (8%) was establised. The hydrocarbon n-undecane (RT 6.777)

was

indicated

as

the

basic

component

of

n-butanol

fraction.

In

chromato-mass-spectrum also 1-butene-4-isothiocyanate (RT 4.165; mass-spectrum: m/z 113 (Μ+), N-methyl-pyrrolidine-2-one (RT 6.262; mass-spectrum: m/z 113 (Μ+, 100%), 98 (97%), 70 (53%), 58 (80%), 5-methylfurane-2-carboxyaldehyde (RT 4.328, mass-spectrum: m/z 110 (Μ+, 100%), 84 (11%), 70 (16%), 53 (52%) were revealed.

· 15 ·

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CHINESE HERBAL MEDICINE BASED ANTIMICROBIAL AGENT SCREENING USING 1-DEOXY-D-XYLULOSE 5-PHOSPHATE REDUCTOISOMERASE AS A TARGET W. Y. Gao College of Life Sciences, Northwest University, 229 North Taibai Road, Xi’an, Shaanxi 710069, P. R. China. E-mail: [email protected] The increasing incidence of bacterial drug resistance has stimulated the development of strategies for new antibiotics screening. Studies on the biosynthesis of terpenoids has provided useful tools because the classical mevalonate (MVA) terpenoid biosynthetic pathway operates in human beings and animals and the newly established non-mevalonate (MEP) pathway acts as the sole source of terpenoids for most human pathogenic microbials. Therefore, every enzyme of MEP pathway can be employed as an ideal target to screen antibiotics. 1-Deoxy-D-xylulose 5-phosphate reductoisomerase (DXR), one of the key enzymes of the novel pathway, catalyzes the first committed step of this nonclassic pathway by conversion of 1-deoxy-D-xylulose 5-phosphate (DXP) to 2-methyl-D-erythritol 4-phosphate (MEP) in a NADPH dependent manner and the reaction also requires a divalent metal ion for catalysis[1]. As a promising target for screening of new antibiotics, it has triggered a lot of studies on looking for its inhibitors[2]. As a result, fosmidomycin, a long known natural metabolite, isolated from Streptomyces lavendulae and its synthetic congener FR-900098 have been established as its inhibitors, which also showed excellent in vitro and in vivo activities against many bacteria and Plasmodium spp.[3]. There are rich resources of medicinal plants in our country. And lots of Chinese herbal medicines (CHMs) possess good anti-microbial activity confirmed by the clinical and pharmacological studies. Thus, based on this results, DXR can be used as a target for the antibiotic screening of CHMs to the discovery of new antimicrobial agents.

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HO HO

O (5)

+

N

I-

O

REFERENCES 1.

S. Takahashi, T. Kuzuyama, H. Watanabe, H. Seto. Proc. Natl. Acad. Sci. U.S.A. 95, 9879–9884 (1998).

2.

M. Rohmer. In Comprehensive Natural Products II, Chemistry and Biology L. Mander, H.-W. Liu, Eds.; Elsevier, Vol. 1, pp. 517-555 (2010).

3.

(a) H. Jomaa, J. Wiesner, S. Sanderbrand, B. Altincicek, C. Weidemeyer, M. Hintz, I. Türbachova, M. Eberl, J. Zeidler, H. K. Lichtenthaler, D. Soldati, E. Beck, Science, 285, 1573-1576 (1999); (b) R. P. M. Fernandes, C. Phaosiri, P. J. Proteau, Arch. Biochem. 444, 159–164 (2005); (c) M. A. Missinou, S. Borrmann,, A. Schindler, S. Issifou,, A. A. Adegnika,, P.-B. Matsiegui. Lancet 360, 1941-1942 (2002).

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DEVELOPMENT AND OPTIMIZATION OF HP-TLC AND HPLC ASSAYS FOR ISATIS INDIGOTICA FORTUNE EX LINDL. (ISATIDIS RADIX, BANLANGEN) G. Özek1, K. H. C. Başer2 1

Department of Pharmacognosy, Faculty of Pharmacy, Anadolu University, 26470, Eskisehir, Turkey

2

Department of Botany and Microbiology, King Saud University, College of Science, 11451 Riyadh, Saudi Arabia Aim of the present work was development and optimization of HP-TLC and HPLC

assays for Isatis indigotica Fortune ex Lindl. This plant is a Chinese drug known as Isatidis Radix or Banlangen. The HP-TLC analysis was performed by using a CAMAG system. Plant material was extracted with ethanol (70% in water) and then it was applied onto the plate by using Automatic TLC Sampler 4 device. Different parameters of TLC analysis were optimized to get the most reliable results. A simple and rapid HPLC assay was proposed for qualitative and quantitative evaluation of arginine (major compound) in the drug. ELSD was used for the detection of an arginine without any preliminary derivatization procedure. The ELSD utilizes a high-efficiency LED type of light source and enhanced digital signal treatment to minimize noise and deliver optimum sensitivity for trace analysis.

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THE ANTI-DIABETIC PROPERTIES OF TWO SESQUITERPENE LACTONES FROM CICHORIUM GLANDULOSUM X. L. Xin1,2, H. A. Aisa1, J. P. Ye2 1

State Key Laboratory Basis of Xinjiang indigenous medicinal plants resource utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, P. R. China 2 Pennington Biomedical Research Center LSU System Baton Rouge, LA 70808 USA Cichorium glandulosum is a kind of traditional Uyghur medicine, which mainly

distributed in Xinjiang and Caucasus region, it has the functions of clearing liver-heat, cholagogue, stomachic, digestive, diuretic, detumescent, and can be used in treating jaundice hepatitis, acute glomerulonephritis, and tracheitis. Up to now, more than thirty compounds and five polysaccharides were isolated from the seed; stem and root of this plant, such as sesquiterpenoids, flavonoid, triterpenoids, coumarin, etc. and three of them are new compounds. In this paper, two kinds of marker compounds of this plant –lactucin and lactucopicrin were selected to study their functions and mechanism on anti diabetes by comparing glucose consumption, glucose uptake, fatty acid oxidation, RT-PCR and western bolt with blank and positive control. The glucose consumption and glucose uptake could be enhanced by these two compounds in some concentration on H4IIE, 3T3-L1and L6 cell line, but they had no effect on fatty acid oxidation and PPARγ. Like the positive control, they also decreased the expression of HK1 and PDK1 and increased the expression of PGK1 and Aldoc, but on the expression of ERO1and PFKFb1, they were different with the blank control. Western blot analyses shown that all of this two compounds could active AMPK, P38-MAPK, GSK-3 phosphorylation in the skeletal muscles cell, stimulated translocation of GLUT1and GLUT4 transporters, no significant change could be found on IRS-1, ACC, IR, , 70S6K. Acknowledgements: This work was supported by China National Funds for Distinguished Young Scientists No. 30925045, by the modernization of Minority Medicine in Xinjiang (200733146-4). · 19 ·

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THE CHEMICAL COMPOSITION AND ANTIOXIDANT ACTIVITY OF AVOCADO (PERSEA GRATISSIMA GAERTNER.) SEED AND LEAF ESSENTIAL OILS H. T. Kiyan, B. Demirci, F. Demirci, K. H. C. Baser Anadolu University, Faculty of Pharmacy, Department of Pharmacognosy, 26470 Eskisehir, Turkey Avocado (Persea gratissima Gaertner.) leaves are used for treatment of constipation in Turkish traditional medicine. Its fruit and leaf extracts are reported to have hypotensive effect and the fixed oil of fruits is known to have use in cosmetics [1]. In the present study, essential oil composition and antioxidant activity of avocado seeds and leaves were investigated. The essential oils were obtained by hydrodistillation, which was analyzed both by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS), simultaneously. The main constituents of the oils were identified as germacrene D (26.2%), avocadenofuran (8.8%), α-pinene (7.1%) for seeds while methyl chavicol (60.7 %), β-pinene (11.9%), methyl eugenol (10.8%) for leaves, respectively. Furthermore, the essential oils were screened for their radical scavenging activity by the DPPH-TLC assay [2]. The leaf oil showed weak antioxidant acitivity whereas the seed oil showed moderate activity at low concentrations ( luteolin > quercetin > isoquercetin > kaempferol > ursolic acid. MTT assay was used to observe the inhibition of these components on growth of Hela, BGC-823 and SW-480 cancer cell lines in various concentrations for 48h, it demonstrated that gallic acid, ellagic acid and ursolic acid presented growth inhibition on the proliferation of Hela, BGC-823 and SW-480 cells in vitro. Flow cytometric analysis showed that BGC-823 cells were arrested at S phase after treated with gallic acid, arrested at G2/M phase after treated with luteolin, while arrested at G1/G0 and G2/M with ursolic acid. At the concentration of 40 μM, ursolic acid and luteolin induced obvious apoptosis in BGC-823 cells. It was showed that the anti-oxidation and anti-cancer activities of bioactive components from Pomegranate peels in vitro were tannin and triterpenoid. Proliferation inhibition, apoptosis and cell cycle arrest may be involved in the mechanism of anti-cancer. Acknowledgements: This work was supported by the Western Light Talent Culture

Project funded by Chinese Academy of Sciences (RCPY200601). We thank Zhang Xue (The First Affiliated Hospital, Xinjiang Medical University) for her expert advice and assistance on Flow cytometric analysis.

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DETERMINATION OF PUNICALAGIN AND ELLAGIC ACID IN THE PURIFIED PRODUCTS OF PUNICA GRANATUM PEEL BY RP-HPLC Y. Q. Luoa,b, Rahimaa,b,Y. Lia,b , L. Liua,b , H. A. Aisaa,b a

State Key Laboratory of Xinjiang Medicinal Plants Resource Utilization, Xinjiang

Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China b

Key Laboratory of Chemistry of Plant Resources in Arid Regions, Xinjiang Technical

Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China

The dry peel of Pomegranate (Punica granaum L.) is a traditional Chinese medicine and a type of medical herb in Uighur medicine. It was collected in Chinese pharmacopoeia (2010 edition, vol. I) and can be used as astringent, haemostasis, helminthicide, etc.. The studies of the modern pharmacology have proved that the peel of Pomegranate has the functions of antioxidant activity, antimicrobial activity, anti-inflammation activity, antivirus activity and anti-tumor activity [1-5]. These activities have relationship with the pomegranate tannins such as punicalagin and ellagic acid. The extractions of the peel of pomegranate which was extracted with 40% ethanol solution and purified by the HPD-300 macroporous resin was proved to be effective in anti-inflammation and anti-bacteria and antipruritic by using vivo pharmacodynamics experimental research. As punicalagin and ellagic acid are the main functional activity components, a RP-HPLC method for simultaneous determination them was established to control the content of punicalagin and ellagic acid of the pomegranate peel purifications: Phenomenex Gemini C18 column (4.6×250 mm, 5 μm) was used with methanol-acetonitrilewater (0.2% trifluoroacetic acid, v/v) as the mobile phase, gradient elution. The flow rate was 0.8 mL·min-1 and column temperature was 30 ºC. 280 nm was selected as the detected wavelength. The results of calibration curve was linear within the range of 0.0976 mg·mL-1-0.610 mg·mL-1(R2 =0.9991)for punicalagin and 0.0105 mg·mL-1-0.0602 mg·mL-1 (R2=0.9998)for ellagic acid, respectively. The recoveries (n=9) of punicalagin, ellagic acid

were 103.2% and 101.2%, respectively. RSD were all below 1.50%. The conclusion showed · 116 ·

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that the method was simple, accurate and exclusive, and it can be used for the quality of Pomegranate Peel Extract. Acknowledgements

This work was supported the CAS/SAFEA International Partnership Program for Creative Research Teams. REFERENCES

1.

R. P. Singh, M. K. N. Chidambara, G. K. Jayap rkasha . Studies on the antioxidant activity of pomegranate peel and seed extracts using in vitro models. J. Agric. Food Chem. 50, 81-86 (2000).

2.

P. S. Negi, G. K. Jayap Rakasha, B. S. Jena. Antioxidant and antimutagenic activities of pomegranate peel extracts. Food Chem. 80, 393-397 (2003).

3.

K. B. Ajaikumar, M. Asheef, B. H. Babu, et al. The inhibition of gastric mucosal injury Punica granatum L. methanolic extract. J. Ethnopharm. 96, 171-176 (2005).

4.

D. Prashanth, M. K. Asha, A. Amit. Antibacterial activity of Punica granatum. Fitoterapia 72, 171-173 (2001).

5.

J. Zhang, B. Y. Zhan, X. J. Yao, et al. Killing Effect of Punica granatum L. against HBV in vitro. Pharmacology and clinics of Chinese Materia Medica 13(4), 29-31 (1997).

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ESTROGENIC ACTIVITY OF ISOFLAVONES EXTRACTED FROM CICER ARIETIUM L. SPROUTS H. R. Maa, J. Wanga, b, H. B. Weia,b, Z. Chena, Y. Yanga, H. A. Aisaa a

Xinjiang Key Laboratory of Plant Resources and Natural Products Chemistry, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi,

830011, China; Tel.: +86 9913835679; fax: +86 9913838957. E-mail: [email protected] b

Key Laboratory of Xinjiang Endemic Phytomedicine Resources, Ministry of Education, College of Pharmacy, Shihezi University, Shihezi 832002, China Cicer arietinum L. (Chickpea) is one of the oldest and most widely planted legumes in

the world. As traditional Uighur medicine, chickpea has been widely applied in treating and preventing the hypertension, hyperlipidemia, diabetes, skin itching, flatulence, low libido, tumor prevention and osteoporosis. Isoflavones are the important chemical components of the seeds and sprouts of chickpea. Isoflavones as known one group of phytoestrogens, are given much attention due to their potential therapeutic application. In recent study, we systematically evaluated the estrogenic properties of isoflavone mix extracted from Cicer arietium L. sprouts (ICS) using four in vitro bioassays methods. Flow cytometric analysis showed that ICS at the concentrations of

1 μg/mL promoted MCF-7 cell growth and improved the proliferation rate. ERα/Luc transcription assay and then semi-quantitative RT-PCR analysis indicated that ICS induced ERα-mediated luciferase activity in MCF-7 cells and promotes the ER downstream target gene pS2 and PR transcription, and this effect were inhibited by ICI 182,780, a special antagonist of ER, indicating an ERα-mediating pathway. Finally, alkaline phosphatase (AP) expression in Ishikawa cells showed that ICS stimulated AP expression in Ishikawa cells. In summary, estrogenic activities of the crude isoflavones extracted from Cicer Arietium L. sprouts were described for the fist time and implied the possibly beneficial therapeutic potential.

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PRODUCTION AND CHARACTERIZATION OF PROTEIN HYDROLYZATES FROM LOCAL RAW MATERIAL Sh. R.Madyarova,b, P. B. Usmanovb, B. A.Tashmukhamedovb a

Institute of Zoology, Academy of Science of the Republic of Uzbekistan, 1, Niyazov Str., Tashkent , 700095, Uzbekistan, E-mail: [email protected]

b

Institute of Physiology and Biophysics. Academy of Science of the Republic of Uzbekistan, Tashkent, Uzbekistan

Protein hydrolyzates are broadly used for medical and allergen-free nutrition, in microbiology, as polyfunctional immunomodulatory prophylactic medicines, components of biologically-active additives and artificial diets, in cosmetics, as antioxidants, flavor additives in food industry and for many other purposes. Some potential protein products, agriculture and food industry wastes are tested in present study. Among them are: blood of agricultural animals and its components, gelatin, lacto serum, baker's yeast, proteins of cotton and soya cakes, silkworm pupae, silk fibroin and sericin and other protein materials and wastes. Resource-saving problems are solved simultaneously. Chemical and enzymatic methods, as well as autolysis of protein products we used in the work. To increase efficiency of acidic or alkaline hydrolysis we used the surplus pressure in the media, preventing oxidation and destruction of hydrolysis products. After hydrolysis the media was cooled down, neutralized without dilution, and evaporated. Fractionation, analysis and specification of hydrolysis products were carried out by ultra- filtration, dialysis, gel-permeating, paper and thin-layer chromatography as well as by spectrophotometry. Optimal conditions for efficient hydrolysis of studied plant and animal protein materials to obtain products mixture (peptides and amino acids) having biological effects were found as a result of the study, using earlier improved method of natural silk proteins hydrolysis. It is shown that hydrolysis at low temperature with use of autolysis and enzymes gives higher output of native products. The obtained products of hydrolysis were compared by physico-chemical characteristics with similar Russian preparations (baker's yeast autolysate "Alexandrina") and with Chinese · 119 ·

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and South Korean preparations of silk fibroin hydrolyzates, as well as with other commercial preparations of protein hydrolyzates. Protein hydrolyzates obtained by proposed method did not yield to foreign analogues by its characteristics. For example, fibroin hydrolyzates obtained in the present work did not require the additional purification. At present these and other characterized hydrolyzates are tested in composition of artificial diets as biostimulators of development and productivity in biotechnology of insects and biopesticides of last generation.

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ISOLATION, CHARACTERIZATION AND STABILIZATION OF PHOSPHOLIPASE D FROM DAIKON RAPHANUS SATIVUS LONGIPINNATUS Sh. R. Madyarov Institute of Zoology, Academy of Sciences of the Republic of Uzbekistan 1, Niyazov Str., Tashkent, 700095, Uzbekistan, E-mail: [email protected]

Phospholipases are often used for hydrolysis and synthesis of phospholipids, for analysis and soft modification of biomembranes. Phospholipase D (PLD) EC-3.1.4.4. is a multifunctional enzyme participating in membrane homeostasis, in intracellular signaling and regulation, catalyses reactions of hydrolysis and trans- alkylation of phospholipids. Properties of PLD isolated from daikon which is one of the perfect sources for obtaining of this enzyme have been studied in the present work. Daikon radish PLD immobilized into silk matrices has been obtained also for pharmaceutical synthesis of phospholipids in organic solvents. Isolation of PLD was performed by homogenization of daikon radish in appropriate buffer, centrifugation of homogenate and by double step precipitation of supernatant by cooled acetone (-15 оС). This crude PLD preparation did not contain other lipolytic activities and proteolytic enzymes and can be used for practical tasks. PLD from peanut and Streptomyces cromofuscus for comparison, L-α-lysophosphatidyl choline from hen egg yolks

and soya beans, palmitoyl L-α-phosphatidyl choline were the products of Sigma Chem. Company. Product formation of lysophosphatidilcholine’s hydrolysis (L-a-lysophosphatidic acid calcium salt) in the process of reaction was determined by TLC and spectrophotometrically. Some PLD properties in comparison with analogous purchased preparations from cabbage and Central Asian radish

and

are represented. Purified PLD was obtained from

this crude preparation by one-stage hydrophobic chromatography on Octyl-sepharose CL-4B. For comparison purified PLD from Central Asian radish was obtained by the same method. Molecular weight of PLD from daikon is 75 kD and molecular weight of Central · 121 ·

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Asian radish is 82 kD. These enzymes are able to perform hydrolysis and transphosphatidylation of phospholipids. Specific hydrolytic activity of purified PL-D from daikon with egg yolk lysolecithin is ~1000 U/mg; pHopt. 5.0-6.0; Topt. 45-52 oC; [Ca]opt. 5-20 mM, [S]opt. 2-5 mM. Thereby daikon radish Raphanus sativus longipinnatus introduced to culture in Uzbekistan represents significant resource for biotechnological manufacture of PL-D and its use in food industry and pharmacy. Purified PLD can be used in study of its mode of action on artificial and natural membranes. Nano-matrix PL-D preparations for prolonged biocatalysis in organic media have been obtained on the basis of silk industry wastes.

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ISOMERIC REFERENCE SUBSTANCES PREPARATION OF ISORHAMNETIN-3-O--D-GLUCOSYL(61)--L-RHAMNOSIDE AND ISORHAMNETIN -3-O--D-GALACTOSYL-(61)--L-RHAMNOSIDE FROM ALHAGI SPARSIFOLIA S. Mansura, K. F. Hana, A. Ayupbekb, G. A. Zoub, H. A. Aisab a

Institute of Science, Beijing University of Chemical Technology, Beijing 10029, P. R. China;

b

Key Laboratory of Chemistry of Plant Resources in Arid Regions, Xinjiang Technical

Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, P.R. China. Tel: +86-991-3835679, E-mail: [email protected] Alhagi sparsifolia Shap. (camelthorn) is a perennial subshrub of the family Leguminosae. It is mainly distributed in Central Asia and Xinjiang Autonomous Region of P. R. China, and commonly used in traditional Uyghur medicine for the treatment of physically weak, dizzy, cold, rheumatism, joint swelling, abdominal pain, diarrhea, stomachache, neurogenic headache, toothache, and cancer. In our research of bioactive chemical constituents from A. sparsifolia,

two

isomers

of

isorhamnetin-3-O--D-glucosyl-(61)-α-L-rhamnoside

(isorhamnetin-3-O-rutinoside) and isorhamnetin-3-O--D-galactosyl-(61)-α-L-rhamnoside were yielded with high content up to 0.1355% and 0.1250%, respectively. The n-BuOH fraction from the EtOH extract of A. sparsifolia was subject to column chromatography on silica gel, eluted with a gradient of CHCl3–MeOH (90 : 10 to 70 : 30) and CHCl3–MeOH–H2O (70 : 30 : 10 to 60 : 40 : 10). The fraction contained these two isomers was rechromatographied and purified by Sephadex LH-20 column chromatography and preparative HPLC, using methanol-acetonitrile-0.3% formic acid/water (14: 11: 75) as mobile phase. Their structures were identified by spectroscopic analysis. The purity of both isomers analyzed by HPLC was more than 99%. The isomers acquired by this method meet the relevant requirements of the chemical reference substances and could supply scientific evidence for the quality control and the active substance basis of A. sparsifolia as well as its related preparations. Acknowledgements: This research work was financially supported by West Light Foundation of the Chinese Academy of Sciences (to G. A. Zou, Year 2009). · 123 ·

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NEW INDUCTOR OF INTERFERON ON THE BASES OF CMC AND SALICYLAMINE S. A. Maulyanova, A. A. Sarimsakovb, A. N. Narovlyanskiyc, D. N. Dalimova a

National university of Uzbekistan named after M. Ulugbek , Tashkent, Uzbekistan b

c

Institute of chemistry and physics of polymers of SA RUz, Tashkent, Uzbekistan

Institute of epidemiology and microbiology named after E. F. Gamal, Moscow, Russian

One of intensively developing directions of polymeric and bioorganic chemistry is synthesis of the new derivatives of known natural and synthetic polymers, carring out with aim of obtaining of compounds having biological activity. In this connection an addition of low molecular weight component, increasing of solubility in water and appearance of the prolonged action of the synthesized drugs. Elaboration of a high effective drug of wide spectrum of action《Savrac》on the base of salycilamine and the acidified form of the water-soluble cellulose acetate (AWSCA) Proves the above-stated assumption. We

have

carried

out

of

condensations

Salycilamine

with

dialdehyde

of

carboxymethylcellulose at constant stirring at room temperature. Products of reaction were evolved by recipitation in acetone and for removal of not reacted low molecular weight component the a deposit consistently was washed out by acetone and ethanol. Thus for the first time the new biodecomposed polymeric modification of salycylamine on the base of dialdehyde of carboxymethylcellulose was synthesized and it’s antivirus activity at hepatite was determined. Biological investigations of interferon induction action of the drug carried out in Institute of epidemiology have shown,that in doze 1mg/mL titres of interferon in some times exceed titres of known drugs Ridostine and Cycloferon applied in medical practice.

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MATRICARIN - SESQUITERPENE LACTONE FROM CANCRINIA DISCOIDEA (LEDEB.) POLJAK. O.V. Morozova, N.K. Zhappar, S.A. Ivassenko, G.A. Atazhanova, S.M. Adekenov JSC «International research and production holding «Phytochemistry», 100009, Republic of Kazakhstan, Karaganda, [email protected] Cancrinia discoidea (Ledeb.) Poljak is an annual plant with thin root and branchy stalk.

It grows on coast sands and sandy soils near to the rivers and lakes on the ballast stone and clay slopes of foothills [1]. The aerial part of Cancrinia discoidea with mass of 1,3 kg., collected near to the Gulshat village of the Aktogaisky area of the Karaganda oblast, has been extracted 4 times by chloroform in the ratio of 1:10 (raw material : solvent). The chromatographic separation has been carried out on silica gel marked by the KSK. The colorless crystal substance with m.p. 201-204°С has been isolated during the elution of column by the mixture of petroleum ether - ethyl acetate (17:3). O

OCOCH3 H O O

(1)

The comparison of the physical and chemical and spectral data (IR-, NMR 1Н, 13С, mass spectra) and X-ray analysis of the isolated compound with the literary data [2], it has been determined that compound is identified as sesquiterpene lactone matricarin (1). The yield of matricarin has made 0.06% in recalculation on air-dried raw material. Matricarin has been isolated from Cancrinia discoidea (Ledeb.) Poljak for the first time. REFERENCE

1. Flora of Kazakhstan / under N.V. Pavlov's edition - Alma-Ata: Nauka. 1965, V.-9, P.-48. 2. K.S. Rybalko Natural sesquiterpene lactones, Moscow: Medicina, 1978. · 125 ·

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STUDY OF THE EFFECTS OF CELLULOSE SULFATE ON THE INFECTIVITY OF TOBACCO MOSAIC VIRUS B. I.Muhitdinova, N. S.Normakhamatova, Z. N.Kadyrovab, K. M.Churkinaa, A. S. Turaeva a

A. S. Sadykov Institute of Bioorganic Chemistry, AS of Uzbekistan, 83, M. Ulughbek Str. Tashkent, Uzbekistan

b

Institute of Genetics and Experimental Plant Biology, AS of Uzbekistan, Tashkent

Special attention has been paid to the investigation of plant deceases in many countries of the world. For example, tomato plants grown up in field and greenhouse conditions are often very easily infected tobacco mosaic virus (TMV). In infected with TMV potato plants it is observed lowering of growth, branching, intensity of flowering and holding the fruits. Currently in practice there is no any concrete preparation against TMV infections in potato plants. It is known that, preparations on the basis sulfated polysaccharides possess antibacterial, anticoagulant, fungicidal, antiviral and other properties. In our investigations we researched antiviral activities of sulfated cellulose (SC) against TMV. SC samples were obtained with sulfation of cellulose with pyridine-chlorosulfonic acid complex. The molecular parameters of obtained samples were determined with complex physico-chemical methods. The degree of substitution of obtained samples was 2.5-3.0 and intrinsic viscosity was 0.46-5.4. Antiviral activity of SC studied on tomato strain of TMV (TMV-TS) which was isolated from the infected tomato plants growing in field conditions. TMV-TS isolation was carried out by passing to mononecrosis of Nicotiana glutinosa. A virus accumulated in N. clevliandii. Viral homogenate was prepared from fresh or frozen (-20 ºС) leaves of N. clevliandii which was ground in a mortar with the addition of carborundum and 0.1 M phosphate buffer pH 7.5. Homogenate was centrifugated at 8 000 rot./min for 10 minutes. Virus containing liquid was used for the further researches. Carried in vitro experiments showed that, the optimum inhibitory concentration of SC was 0.05% with the ratio 1:1 (SC and TMV-TS) It is established, that SC blocks the penetration of TMV into the cells of host plant. · 126 ·

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Coating the preparation on a surface of leaves N. glutinosa the local necrosis region decreased till 70-80 % comparing to control leaves. Thus, preparations of SC reduce infection TMV-TS in vitro, slow down penetration of a virus into the plant cells. Antiviral activity of SC against TMV depends on the concentration of the solution, on the time applying, molecular weight and the degree of sulfate group substitution of the macromolecule. In our future investigation we will research the relationships between antiviral activity and molecular parameters of SC.

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BROMINATION OF HYDROCHLORIDES OF 2,3-TRI(TETRA)METHYLENE-3,4-DIHYDROPYRIMIDINE-4-ONES WITH N-BROMOSUCCINIMIDE N. I. Mukarramova, Kh. Z. Khakimovab, Kh. U. Khodjaniyazova, Kh. М. Shakhidoyatov1 a

Institute of the Chemistry of Plant Substances named after Academician S. Yu. Yunusov AS RUz, Tashkent, Fax (99871) 1206475, E-mail:[email protected] b

Karshi State University

For the purpose to investigate of bromination of 2,3-tri(tetra)methylene-3, 4-dihydropyrimidine-4-ones

hydrochlorides

we

have

done

reaction

with

N-bromosuccinimide (NBS) in rate of reagents 1:1 at room temperature in water solution. By 1

the results of

Н NМR-, chromatomass-spectral analysis it was shown forming of

5-bromo-6-methyl-2,3-trimethylene-3,4-dihydropyrimidine-4-one. O

O N

H 3C

N .. HCl

(CH 2)n

NBS

Br H 3C

1,2

N

(CH 2)n

N

1,3 n=1 2,4 n=2

3,4

In a spectrum compound 3 1Н NМR presence of signals, characteristic for protons of methylene groups is observed at 4.29 ppm (2H, t, -СН2, J = 7.6 Hz), 2.44 ppm (5H, m, -СН2, 6-CH3), 3.52 ppm (2H, t, -СН2, J = 7.6 Hz). Absent of proton signals at 6.48 ppm

(1H, q, С5-м, J = 7.6 Hz) of first compound specifies that bromination goes to atom С5. Having in chromatomass-spectral peaks of molecular ions corresponding m/z 228/230 (100 %) and characteristic ions m/z 213/215 (M+-15, 23%), 197/199 (M+-28, 20%), 149 (M+- 79,

19%),

121

(M+ - 107,

48%)

also

confirm

5-brome-6-methyl-2,3-trimethylene-3,4-dihydropyrimidine-4-one.

· 128 ·

the

structure

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NUCLEOPHILIC SUBSTITUTION REACTIONS OF Α-OXYMETHYLIDENE-2,3,4,10-TETRAHYDRO-1HPYRIDO[2,1-b]QUINAZOLIN-10-ONE A. O. Nasrullaev, B. Zh. Elmuradov, Zh. E. Turdibaev, Kh. M. Shakhidoyatov Institute of the Chemistry of Plant Substances, Academy of Sciences, Republic of Uzbekistan, Mirzo Ulugbek str., 77, Tashkent; Fax: 998-71-120-64-75; E-mail: [email protected]

Formylation

of

tricyclic

quinazoline

2,3,4,10-tetrahydro-1Н-pyrido[2,1-b]quinazolin-10-one

alkaloid

(1),

isolated

from

plants

Mackinlaya subulata Philipson and M. Makrosciadia (Araliaceae) [1] with Vilsmeyer-Haack

(DMF+POCl3)

reagent

gives

-hydroxymethyliden-2,3,4,10-tetrahydro-1Н-pyrido[2,1-b]quinazolin-10-one (2) [2,3].

In the present report, we carry out the reaction of 2 with o-, m-, p-aminophenols in equimolar rations, and corresponding products (3a-c) have been synthesized with good yields: O

O

O N

N

N

N

a N

N

1

b

CH-NH

3a-c

CH-OH

2

OH

d

N

N

N

c

+ N

N

N 4

O

O

O

CH-Cl

6

CH-SeH

5

H_ Cl

CH-Cl

The reaction of 2 with thionyl chloride gives -chloromethyliden-1 (4) or its hydrochloride (5). The nucleophilic substitution of chlorine atom of compounds 4 by sodium hydroselenide gives -hydroselenylmethyliden-2,3,4,10-tetrahydro-1Н -pyrido[2,1- b ] quinazolin-10-one (6). The structure of the synthesized compounds is confirmed by data of physical methods of investigations.

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Compounds

REFERENCES

1. I. S. Fitzgerald, S. R. Johns, J. A. Lamberton, A. H. Radcliffe. Austral. J. Chem. 19(1), 151 (1966). 2.

J. E. Turdibaev, B. J. Elmuradov, Aibek Malik, Kh. M. Shakhidoyatov. 7th International Symposium on the Chemistry of Natural Compounds: Abstracts, Tashkent, 173 (2007).

3.

A. Sh. Abdurazakov, B. Zh. Elmuradov, A. O. Nasrullaev, S. A. Makhmudov, Kh. M. Shakhidoyatov Highlights in the Evolution of Phytochemistry. Abstract book, Cambridge, 122 (2007).

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NEW INDUCTOR OF INTERFERON ON THE BASES OF CMC AND SALICYLAMINE S. A. Maulyanova, A. A. Sarimsakovb, A. N. Narovlyanskiyc, D. N. Dalimova a

National University of Uzbekistan named after M. Ulugbek, Tashkent, Uzbekistan b

c

Institute of Chemistry and Physics of Polymers of SARUz, Tashkent, Uzbekistan

Institute of Epidemiology and Microbiology named after E. F. Gamal, Moscow, Russian

One of intensively developing directions of polymeric and bioorganic chemistry is synthesis of the new derivatives of known natural and synthetic polymers, carring out with aim of obtaining of compounds having biological activity. In this connection an addition of low molecular weight component, increasing of solubility in water and appearance of the prolonged action of the synthesized drugs. Elaboration of a high effective drug of wide spectrum of action《Savrac》on the base of salycilamine and the acidified form of the water-soluble cellulose acetate (AWSCA) proves the above-stated assumption. We

have

carried

out

of

condensations

Salycilamine

with

dialdehyde

of

carboxymethylcellulose at constant stirring at room temperature. Products of reaction were evolved by recipitation in acetone and for removal of not reacted low molecular weight component the deposit consistently was washed out by acetone and ethanol. Thus for the first time the new biodecomposed polymeric modification of salycylamine on the base of dialdehyde of carboxymethylcellulose was synthesized and it’s antivirus activity at hepatite was determined. Biological investigations of interferon induction action of the drug carried out in Institute of epidemiology have shown, that in doze 1 mg/mL titres of interferon in some times exceed titres of known drugs Ridostine and Cycloferon applied in medical practice.

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ANTIVIRAL ACTIVITY OF SULFATED POLYSACCHARIDES N. S. Normakhamatova, J. P. Zuo b, Ye Yang b, B. I. Muhitdinov a, A. S. Turaeva a

Institute of Bioorganic Chemistry of Uzbek Academy of Sciences, Mirzo Ulughbek Str. 83, Tashkent-100125, Uzbekistan, E-mail: [email protected] b

Shanghai Institute of Materia Medica of Academy of Sciences of the Chinese National Republic, 555 Zu Chong Zhi Road, Zhang Jiang Hi-Tech Park, Pudong, Shanghai

Sulfated polysaccharides (chondroitin sulfate, carrageenan and etc.), presenting in the plant organism provides them with protective functions from various diseaseses. However, the mechanism of implication of protective function is not well studied so far. Last years a number of scientific researches on the antimicrobial, antiviral, antimicotic activity of sulfates of polysaccharides have been reported. The last is caused apparently, with interaction of sulfates of polysaccharides with glycoprotein or polysaccharides in covers of pathogens which result in inhibiting of their activity. The present work is devoted to study of in vitro antiviral activity of the various sulfate derivatives of polysaccharides on hepatite virus C strains. Antiviral activity of sulfated polysaccharides differing among themselves by the polysaccharide nature (on conformation), on molecular weight, on the distribution of sulfate groups, i.e. under the maintenance of sulfated groups were studied. For the purpose of establishment of the influence of molecular weight sulfated saccharides (glucose, galactose), polysaccharides (cellulose, amylose, polygalacturonic acid) were synthesised differing among themselves by glucosidic bond type and accordingly by the conformation. For an establishment of influence of substitution degree (DS), i.e. the maintenance of sulfate groups, samples with DS from 0.5 to 2.85 have been synthesized. Also samples of regioselective substituted polysaccharide sulfates in the elementary repeating unit with disposition of sulfate groups in 2 and 3 carbon atoms have been received. In conditions of in vitro studying of the influence of sulfates of polysaccharides on inhibition of the virus of hepatitis C was performed through advantage of high-throughput screening technology using a cell-based assay to look for new inhibitors of post-entry events in HCV infection is made. The cytotoxicity of “active” compounds identified during the · 132 ·

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primary screening was evaluated by MTT (3-(4,5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide) assay at the end of the incubation period. Influence of sulfates of polysaccharides with various molecular weight on the inhibition of virus of hepatitis C. It was determined, that three sulfates of mono- and di- saccharides (glucose, galactose and sucrose) almost do not show an inhibition activity of viruses. Inhibition of the hepatitis virus C begins with molecular weight of 100 of sulfated polysaccharides and was increased with the further increasing of the degree of polymerization. 96.0% virus inhibition is observed by sulfated cellulose sample with degree of polymerization of 600. Inhibition of the virus of hepatitis C by sulfated polysaccharides with differing of DS was also studied. It is determined, that sulphated cellulose with DS 0.6 has inhibition effect, and it does not vary almost up to DS 2.0. From DS 2.0, inhibition activity of sulfated polysaccharides was increased with stepwise change. It confirms once again that the activity of the preparations depends from the DS. The received results indicate that sulfated polysaccharides, apparently, lead inhibition and prevention of the virus penetration to host target-cell interacting with virus domains.

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Compounds

STUDY OF ANTIVIRUS ACTIVITY OF ALKALOID STACHYDRINE FOR VIRUS OF SHEEP-POX Zh.S.Nurmaganbetov1, E.O.Abduraimov2, A.Zh.Turmukhambetov1, S.M. Mamadaliev2, S.M.Adekenov1 1

JSC “International research and production holding “Phytochemistry”, 100009, Republic of Kazakhstan, Karaganda, [email protected]

2

The Scientific Research Institute of Problems of Biological Safety, Kazakhstan, Zhambylky area, [email protected]

Pyrrolidine alkaloid stachydrine with the betaine structure has been isolated for the obtaining of valuable pharmacologically active heterocyclic compounds of the natural origin [1]. It has been isolated by the alcoholic extract of Capparis spinosa L. leaves, collected in the fruiting phase. We have studied the antivirus activity of this alkaloid for the virus of sheep-pox. It has been determined that the maximum tolerated dose (МTD) of stachydrine for cell culture of lambs’ kidney has made 0.1 mg/ml. During the determination of virus-static actions of stachydrine for virus of sheep-pox in cell culture has been defined that stachydrine in doses of 0.1 MTD, 0.5 MTD and 1 MTD has not the virus-static actions. The determination of viricidal action of stachydrine for virus of sheep-pox in cell culture has been carried out in three modes. Stachydrine has not inhibited the infectious activity of virus of sheep-pox at 37 ºС for 1 hour and at 4 ºС for 16 hours. Thus, the viricidal action of stachydrine in mode of 37 ºС for 16 hours has studied, where stachydrine has shown good viricidal property in doses of 0.05 and 0.1 mg/ml. REFERENCES

1. Kozlova L.M., Pharmacy. (6) 23 - 26 (1967).

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ALKALOID COMPOSITION OF THE CULTIVATED SPECIES DIPTHYCHOCARPUS STRICTUS I. I. Ohunov, M. G/ Levkovich, S. F. Aripova, V. U. Khujaev Institute of the Chemistry of Plant Substances named after Academican S. Y. Yunusov, Academy of Sciences, 1000170, Tashkent, Republic of Uzbekistan, fax (99871) 120 64 75, E-mail: [email protected]

Plant Dipthychocarpus strictus Trautv. belongs to the cruciferous (Cruciferae) and it is annual grass which grows in Tashkent, Kashkadarya, Surkhandarya, Bukhara regions of Uzbekistan and Karakalpakstan. D. strictus is the only member of the genus Dipthychocarpus, which grows in Central Asia and it is a source of sulfur-containing alkaloids, derivatives of N-alkylurea with expressed antihypoxic action. Studies of alkaloids of this plant led to the isolation of number of sulfur-containing alkaloids, which are based on the structural chain, combining thiomethyl, sulfoxide, nitrile group with a molecule of urea in various combinations. To determine the outcome of introducing native species D. strictus as alkaloid containing plant, we investigated the alkaloids of aerial parts of plant species introduced to the Botanical Garden in Tashkent. By quantitative studies it has been found that total alkaloids are 0.06%. Oily mixture of two alkaloids were obtained by chromatographic separation of total alkaloids D. strictus on a column of aluminum oxide of the first petrol-chloroform (4:1) eluates. Two liquid alkaloids were identified by repeat chromatograph of fraction on silica gel column eluting with a gradient mixture of petrol-chloroform. One of them with a value of Rf 0.60 (system: chloroform-methanol, 9:1) turned out to be previously isolated and known alkaloid diptocarpilidine and the other one with Rf 0.65 was a new alkaloid, not described in the literature of minor alkaloids in the past. Isolated alkaloid was oily, optically inactive substance, well soluble in acetone, ethyl acetate, chloroform, methanol, hardly soluble in hexane and petroleum ether. Its UV spectrum shows an absorption maximum at 206 nm (lg  3.05). An IR spectrum was characterized by existence of bands absorbing stretching and bending vibrations of CH3, · 135 ·

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CH2-groups, and also noted the presence of absorption bands at 2200 cm-1 corresponding to nitrile group. Unlike other alkaloids of D. strictus, there is no absorption band of sulfoxide group (1020-1050 cm-1) in the spectrum. These PMR spectrum of the alkaloid showed the presence in the structure of the molecule S-CH3-group, protons of which appear as a triple proton singlet at 1.92 ppm. The signal at 2.72 ppm (2H, m, J = 6 Hz) assigned to the protons of the CH2-S-group at 2.39 ppm detected the signal from protons N = C-CH2-group (2H, t, J = 7 Hz). In the region 1.40 - 1.80 ppm there are 3 signals: 2 multiplets for 2H each at 1.60 (2H, m, CH2 at C2 and 1.72 (2H, m, CH2 at C5) and a multiplet of intensity in the 4 proton units pri1, 4 – 1.5 (4H, m, 2 CH2 at C3 and C4). A comparative review PMR spectra of alkaloids 2 shows that the spectrum diptocarpilidine (2) at 2.57 ppm present 3 proton singlet from the protons sulfinile (CH3-S→O) - group. The PMR - spectrum of alkaloid 1, this signal undergoes a diamagnetic shift is observed at 1.92 ppm. This suggests that a missing oxygen function. Taking into account this fact, it was assumed that the base 1 is diptocarpilidine deoxy derivatives. To confirm this hypothesis held an alkaloid oxidation with hydrogen peroxide. The reaction product was identified with alkaloid diptocarpilidine. Hence, 1 has the structure of 7-(methylthio)heptanenitrile.

Isolation of a new alkaloid desoxydiptocarpilidine of introduced plants collected during the end of the growing season indicates that, apparently, desoxy produce synthesized by plants in the late period of above ground parts. Continuing chromatography total alkaloids D. strictus on a column of alumina from the chloroform eluates identified three crystalline base with m.p. 100-101 ºC, m.p. 135-136 ºC and m.p. 124-125 ºC, identified with the alkaloids diptocarpamine (3), diptocarpidine (4) and diptocarpaine (5). (СН3)2 - СН - NH - CO -NH - (СН2)6 - S (→O) - CH3

(3)

NH2 - CO - NH - (СН2)6 - S (→O) - CH3

(4)

CH3 - S (→O) - (СН2)6 - NH – CO- NH - (СН2)6 - S (→O) - CH3

(5)

All selected crystal base isolated previously from the wild species D. strictus.

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CORRELATION OF DATA NMR 13C AND 1H SPECTROSCOPY WITH INTERNAL SULPHUR CONTAINING ALKALOIDS OF DIPPTHYCHOCARPUS STRICTUS I. I. Okhunov, S. F. Aripova , M. G. Levkovich, N. D. Abdullaev, V. U. Khujaev Institute of the Chemistry of Plant Substances named after Academican S. Y. Yunusov, Academy of Sciences, 1000170, Tashkent, Republic of Uzbekistan, Fax (99871) 120 64 75, E-mail: [email protected]

A number of sulphur containing alkaloids, derivatives of N-alkylurea were isolated earlier from the wild growing plant Dippthychocarpus strictus of Cruciferae family. There is no data on NMR 13C spectra parameters of sulfur containing alkaloids in the state of the art. We studied spectra of NMR 13C sulfur- containing alkaloids for the first time. Table 1 Alkaloids of Dipthychocarpus structures A H

Dipthychocarpaine (3)

H

H

N

N

O 2

4

S

6

O

B Desooxydipthochocarpaine

H

H

H

N

N 2

(4)

C

4

S

6

CH3

O

H 3C

Dipthochocarpamine (5)

CH 3

H 3C

2'

H

H

N

N

3'

· 137 ·

O 2

O

4

6

S CH3

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Chemistry

O S

(1)

of Natural

H

H

N

N

CH3

CH3

H

H

Dipthochocarpiline

N

N

(2)

F Dipthochocarpilidine

S

O S

O

E H3C

Compounds

6'

2'

4'

O 2

4

6

S CH3

O

O

N 2

4

6

S CH3

(6)

NMR spectra of compounds A-F were registered in CD3OD with an internal etalons HMDSO (0 m.d.), on spectrometer UNITY 400+ (Varian) with working frequency 400 MHz for protons and 100 MHz for carbon nuclear. Signals of protons were separated on two characteristic groups. Methyls and methylenes groups, neighboring with heteroatom resonated at 2.5-3.1 m.d., but methylenes signals were on H-3 to H-6 - at 1.3-1.8 m.d. In compounds A, B and C the signals from NH-protons at 4.6 m.d. were detected. In NMR spectrum of compounds A protons of gem-heteroatom formed two clear signals: H-2 (triplet at 3.31 m.d.), two signals H-7 with complex shape as “ddd” (2.775 and 2.708 m.d.) and singlet of methyl group on sulfur (2.567 m.d.). Using methods of double resonance their neighbors - methylenes groups H-3 and H-6 were identified. Double resonance, due to signals of protons of methylene group on H-6 (1.697 m.d), and COSY spectra identified the signals of remaining methylene protons at H-5 and H-4. Using the methods of direct heterocorrelation 1H-13C the signals of carbons in

13

C NMR identified

(Table 1). It was succeeded to measure KCCB for compound A only for heteroatomic methylens on H-2 and H-7 (reference in the bottom of table 1).

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Table 2 NMR specters of A-F compounds Atoms Compd.

NH, CO

2

3

4

5

6

7a

7b

CH3

A (1H)

4.580

3.031

1.449

1.346

1.440

1.697

2.708

2.775

2.567

A (13C)

162.40

4.096

29.51

27.56

31.03

23.71

54.88

B

4.587

3.015

1.540

2.420

C (H)

4.586

3.038

1.250 – 1.500 1.376– 1.499

C (H)

3.714

1.040

D

3.044

1.451

E (H)

3.049

E (H)

3.032

F

2.396

1.337

1.340

1.376 – 1.499 1.429

1.235 – 1.472 1.606

1.425 – 1.515

38.24 1.990

1.696

2.706

2.773

2.566

1.697

2.707

2.774

2.567

1.697

2.708

2.774

2.568

1.530 1.713

2.417 2.713

2.783

1.993 2.570

KCCB: A (H-2, (t, 7.0), H-7a (ddd, 13.0, 8.4, 6.0), H-7b (ddd, 13.0, 8.6, 7.4)), C (H-3', (6×d, 6.5), H-4, (d, 6.5)). In spectra of compounds B, in connection with inconstant character of sulfur atom, first of all, changing for signals of methyl group (1.990 m.d.) and methylene on H-7 (2.420 m.d.) is observed. All other remaining signals were close to those of molecule A. In compound C right part completely repeats the spectrum of compound A. In spectrum of compounds B right side of molecule completely repeats the spectrum of compound A. Left side of molecule is represented by two peculiar signals of N-isopropyl group in 3.714 m.d. (signal methyne proton with 6 KCCB) and in 1.040 m.d (doublet double methyl group). The structure of compound D looks like as dimer of compound A and corespondingly, practically repeats NMR spectrum of compound A. Molecule E can be considered as dimer of molecules A and B, which also was confirmed by NMR specter. In structure of F more considerable changes were observed - in the left side of the molecule triple bond considerably affected on methylen pair H-2 shift to strong field on 2.396 m.d. Other signals remained close to those of compound A.

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AMIDES OF 6-NITROQUINAZOLINE-4-YL-2THIOCARBONIC ACID – POTENTIAL BIOLOGICALLY ACTIVE COMPOUNDS N. B. Pirnazarovab, U. M. Yakubova, Kh. U. Khodjaniyazova, Kh. M. Shakidoyatova a

Institute of the Chemistry of Plant Substances named after Academician S. Yu. Yunusov AS RUz Tashkent, Fax (99871) 1206475, E-mail: [email protected] b

Karshi State University

Earlier by us have been synthesized amides of 6-nitroquinazolinone-4-yl-2-thiocarbonic acid by interaction of 2-methyl-6-nitroquinazolyne-4-one with amines (piperidine, morpholine, aniline) in the presence of sulfur. It was shown, that reaction goes in softer o condition (115-145 С), concerning reaction with none substituted o 2-methylquinazolyne-4-one (135-165 С) With the purpose to find the alternative root of the synthesis of amides of quinazoline-4-yl-2-thiocarbonic acid in the present work there were shown obtaining thioamides by reamidation of other thioamides. Thus, by interaction of anilide of 6-nitroquinazolinone-4-yl-2-thiocarbonic acid (1) with piperidine or morpholine there were done synthesis piperidide (2) or morpholide (3) of 6-nitroquinazolinone-4-yl-2-thiocarbonic acid by scheme: O

O O2N

O2N NH

1

N

S

+

C

HN

NH

X N

NHC6H5 2

X=CH2 3 X=O

S C N X

Under action of aniline or morpholine at 115-130 oС piperidide 6-nitroquinazolinone-4-yl-2-thiocarbonic acid (2) turns to anilide or morpholide of 6-nitroquinazolinone-4-yl-2-thiocarbonic acid (1, 3).

HN

1

C6H5NH2

2

O

3

Similarly goes reamidation 3 to 1 or 2. The data on the factors influencing reactionary process and biological activity of compounds will be resulted. · 140 ·

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SYNTHESIS OF SOME DERIVATIVES OF TWO MAJOR STILBENE GLYCOSIDE OF PINUS SIBIRICA BARK A. V. Pozdeevaa, N. I. Komarovab, A. D. Rogachevb, D. V. Korchaginab, V. G. Vasilievb, N. F. Salakhitdinovb, G. A. Tolstikovb a

Novosibirsk State University, Faculty of Natural Sciences, Russia, Novosibirsk 630090, Pirogov Str., 2

b

N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Russia, Novosibirsk 630090, Lavrentievave., 9

Stilbenes are biologically active compounds that possess various biological properties. The most famous compound of them is probably resveratrol (trans-3,5,4-trihydroxystilbene) which revealed antitumor, antiviral, cardioprotective and many other activities. It was found that the bark of Siberian pine (Pinus sibirica) contained two major stilbene

glycosides,

viz

trans-3,5,4-trihydroxystilbene-4-O-β-D-glucoside

(resveratroloside,

1)

and

trans-3,4-dihydroxy-5-methoxystilbene-4-O-β-D-glucoside

(pinostilbenoside, 2). In our work, some derivatives of these glucosides were synthesized. Methylation of glucosides 1 and 2 by CH3I with K2CO3 in boiling CH3CN gave trans-3,5-dimethoxy-4-hydroxystilbene-4-O-β-D-glucoside

(pterostilbenoside)

with

70-80% yield. Reactions of glycosides 1 and 2 with TrCl and NEt3 in dry CH3CN led to the formation of Ar-O-Tr derivatives as main products. Both the compounds 1 and 2 form 6″-O-Trityl derivatives on sugar residue when reacted with TrCl in dry pyridine. Reactions of 1 and 2 with BrCH2CO2CH3 in boiling CH3CN in the presence of K2CO3 gave Ar-O-CH2CO2CH3 derivatives. Amidation of these methyl esters by series of different primary and secondary amines in absolute CH3OH or EtOH gave a number of amides with moderate to good yields. All the compounds obtained were new.

· 141 ·

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ANALYSIS OF ACTIVE COMPONENTS IN NATURAL PRODUCTS WITH CAPILLARY ELECTROPHORESIS S. D. Qi, H. G. Zhang, X. G. Chen Department of Chemistry, Lanzhou University, Lanzhou 730000, P. R. China; E-mail: [email protected]

The bioactive components kaempferol-3-O-glucoside, 7-hydroxy-8- methoxycoumarin and 8-hydroxycoumarin-7-O-glucoside were analyzed from Sinacalia tangutica by capillary electrophoresis (CE). The effects of ionic liquids (ILs) and high electric field strengths on the separation of basic analytes in nonaqueous capillary electrophoresis were investigated. Trishydroxymethylaminomethane (Tris) and sodium cholate (SC) were used as the main BGE with methanol and acetonitrile as medium. Potentials up to 30 kV were applied with short capillary to generate unusually high electric field strengths (500-1000 V/cm). The result indicated that under optimum conditions, analysis time can be induced by the increased high electric field which cannot induce excessive Joule heating in the capillary. And the accurate results illustrated this nonaqueous capillary electrophoresis (NACE) method was feasible.

1

Fig.

1

2

Structures

of

model

analytes.

3

1:

7-hydroxy-8-methoxycoumarin (C1); 3: 8-hydroxycoumarin-7-O-glucoside (C2)

· 142 ·

kaempferol-3-O-glucoside

(F);

2:

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C1

-0.015

Compounds

(A)

-0.025

C2 F

Absorbance

-0.020

-0.030

-0.035

-0.040

-0.045 0

1

2

3

4

5

6

Migration time (min)

(B)

C2

-0.020

C1

-0.025

F

Absorbance

-0.015

-0.030

-0.035 0

1

2

3

4

5

6

Migration time (min)

Fig. 2 The electropherograms of the standards mixture solution (A) and real sample (B) in NACE,

Buffer

conditions:

10

mM

Tris,

25

mM

SC

and

5

mM

1-butyl-3-methylimidazoium tetrafluoroborate (1B-3MI-TFB) at methanol and acetonitrile (60:40, v/v). Applied voltage: 25.0 kV. REFERENCES

1.

J. W. Jorgenson, K. D. Lukacs. Anal. Chem. 53, 1298-1302 (1981).

2.

E. G. Yanes, S. R. Gratz, M. J. Baldwin, S. E. Robison, A. M. Stalcup. Anal. Chem. 73, 3838-3844 (2001).

3.

M. Vaher, M. Koel, M. Kaljurand. Electrophoresis 23, 426-430 (2002).

4.

S. D. Qi, S. Y. Cui, X. G. Chen, Z. D. Hu. J. Chromatogr. A 1059, 191-198 (2004).

5.

M. -L. Riekkola, M. Jussila, S. P. Porras and I. E. Valkó. J. Chromatogr. A 892, 155-170 (2000). · 143 ·

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STUDYING OF COLLAGEN AS A HAEMOSTATIC AGENT O. I. Radzhabov, Т. Gulyamov, A. S. Turaev, N. M. Husniddinova, D. S. Kazantseva A. S. Sadykov Institute of Bioorganic Chemistry, AS of Uzbekistan, 83, M. Ulughbek Str. Tashkent, Uzbekistan

Local hemostatics are widely used both in surgical practice, and in a life for the stopping of parenchimatous bleedings (on the liver surgery). Collagen occupies special place among the natural polymers possessing haemostatic property. Objective of this research was studying of haemostatic property of different samples of collagen: collagen in the form of large powder, a quaggy sponge and a dense sponge received from raw-leather of large horned livestock by processing by its alkali-salt solution and buffer infusion with the subsequent dehydration in the water- dehydrating mediumacetone, ethanol. Experiments have been supplied on 30 white outbred rats of both sexes in mass of 200-220 g at which under nembutal narcosis (30 mg/kg) at intraperitoneal introduction. By acute scalpel a cut on centre and stomach centerline was made and took a liver. On one of liver shares cut off a scrap in the size of 0.3 mm in width and 13 mm in length and puted filter paper scraps to the traumatic surfaces (preliminarily dried in a thermostat and weighed) and gauze tampon that served as the control, changing them through every 15 sec up to stopping of the bleeding. Results of research of haemostatic action of collagen in comparison with the control showed, that collagen in the form of large powder reduced time of

parenchymatous

bleeding in rats in 6.7 times in relation to the control (filter paper) and in 3 times in relation to the control (Hemocell-2®-knitted viscose). Collagen in the form of large powder is inferior in respect of comparison (Thrombocol®, Russia) and exceed activity of “Collastipt” (Germany) in 3.5 times. Thus, the received results indicated a good haemostatic action of the presented samples of collagen on model of a parenchymatous bleeding at rats.

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EVODIAMINE INDUCES CELL DEATH VIA SIMULTANEOUS INSTIGATION OF APOPTOSIS AND AUTOPHAGY IN HUMAN GASTRIC ADENOCARCINOMA SGC-7901 CELLS A. Rasula, B. Yu b, K. Zhanga, L. F. Yanga, M. Khana, T. Ma a,b*, H. Yangb* a

Central Research Laboratory, Jilin University Bethune Second Hospital, Changchun, 130041, People’s Republic of China, b School of Life Sciences, Liaoning Normal University, Dalian 116029, People’s Republic of China

Evodiamine, a naturally occurring alkaloid isolated from Evodia rutaecarpa, possesses potent anticancer activity. It has been reported that Evodiamine induced apoptosis in various cancer cells and autophagy in HeLa cancer cells. The relationship between Evodiamine-induced apoptosis and autophagy was still in question. However, reports indicate that relationship between autophagy and apoptosis exists. Furthermore, the simultaneous activation of the both pathways by several compounds has been observed and both the processes contributed to cell death. In this study, we examined the anti-proliferative effects of Evodiamine against adenocarcinoma SGC-7901 cells and its ability to induce autophagy, apoptosis, and cell cycle arrest for the first time. Here we report that Evodiamine induced apoptosis and autophagy in SGC-7901 cells simultaneously. Evodiamine specifically induced morphological changes in adenocarcinoma SGC-7901 cells. It was found that Evodiamine induced apoptosis in SGC-7901 cells. Autophagy was stimulated by Evodiamine, as was demonstrated by the positive autophagosomes-specific dye acridine orange (AO) staining. The autophagy effects of Evodiamine were further verified by quantification of acidic vesicular organelles (AVOs) in flow cytometry. Interestingly, inhibition of autophagy by autophagy inhibitor 3-methyladenine reversed the Evodiamine-induced cell death in SGC-7901 cells, thus indicating that Evodiamine-induced autophagy may contribute to cell death. Additionally, it was found that Evodiamine also enhanced level of ROS in SGC-7901 cells. The inhibitory effects of SGC-7901 cells were associated with apoptosis, autophagy, and cell cycle arrest at G2/M phase in a dose-dependent manner. These results suggest that Evodiamine is an effective natural compound that has worth for further mechanistic and therapeutic studies against human gastric cancer. · 145 ·

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HYPOCOAGULATORY PROPERTIES OF SULFAPORIN IN HYPERCHOLESTEROLEMIA Kh. A. Rasulova, F. Kh. Inoyatova, G. M. Kutlikova, R. Yu. Milusheva, A. T. Ergashev Tashkent Medical Academy, Uzbekistan

Atherosclerosis and hypercholesterolemia are manifested by the development of hypercoagulation that necessitates the search hypolipidemic drugs from natural compounds. In this regard, promising is the use of chitosan derivative sulfaporin obtained from Bombyx mori. Objective: To study hypocoagulatory properties of sulfaporin on models of

experimental hypercholesterolemia and atherosclerosis. Materials and methods: Hypercholesterolemia (HC) was reproduced in 26 rabbits by

the introduction of cholesterol in food within 3 months. HC development was determined by the change in lipid and lipoprotein spectrum of blood serum. We observed morphologically significant atherosclerotic changes in the aorta by the final deadline. Animals by this time divided into 3 groups: the 1st group - placebo (8 rabbits), the 2nd one received heparin at standard doses (7 rabbits), and the 3rd one – sulfaporin in a dose of 0.2 mL/kg per day intravenously within 1 month. The main parameters of platelet-vascular and coagulation hemostasis were studied. Digital material was processed by the method of variational statistics. Results: In rabbits with HC clotting time was revealed to shorten: onset – 112.2±24 sec,

end – 173.2±6.1 sec, whereas in control these indexes were 176±13.2 sec and 253±15.9 sec, respectively. At the same time, thrombin time was shortened, platelet count, their adhesive and aggregation activity, as well as prothrombin index (PTI) and the concentration of fibrinogen in plasma were increased, indicating the development of hypocoagulatory syndrome in experimental animals. Pharmacotherapy with heparin significantly improves platelet-vascular and coagulation hemostasis in animals. Compared with heparin, application of sulfaporin for a long time led to a significant decrease in platelet count to 237.8±6.2×109 / L vs. 248.1±15.7×109 / L after heparinotherapy. Intravascular blood coagulation was also significantly lengthened. Drugs decreased prothrombin and had inhibitory effect on platelet · 146 ·

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aggregation. Thrombin time was lengthened to 11.4±0.86 and 10.8±3.2 sec, whereas PTI was decreased on 17.1 and 16.5% after use of heparin and sulfaporin, respectively. Fibrinogen was significantly decreased by 39.1 and 46.9%, compared with those before treatment, respectively in the groups treated with heparin and sulfaporin. Conclusions: Pharmacotherapy of HC with sulfaporin leads to decrease in platelet

count, prolongation of intravascular blood coagulation, testifying to hypocoagulatory effect of the drug on vascular hemostasis. Sulfaporin reduces the concentration of fibrinogen and PTI, prolongs thrombin time. Sulfaporin, being an effective anticoagulant with direct action, has heparin-like effect and is a welcome additional therapy for hypercoagulatory states.

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TRANS ISOMERIZATOIN IN PROCESSING PRODUCTS OF NATURAL VEGETABLE OIL M. N. Raximov, J. S. Abduvaliyev, K. X. Majidov Bukhara Engineering-Technical Institute of High Technologies. 200017 Bukhara, Republic of Uzbekistan, Fax:+(36522)36197,e-mail:[email protected] Open Joint-Stock Company "Tashkent yog’-moy” 1000000 Tashkent city, Republic of Uzbekistan Fax: (3712) 965702. E-mail: [email protected], e-mail:[email protected].

Natural vegetable oil and fat are used for productions of wide assortment of food products. Natural oils are subjected to catalysis modification for productions of margarine products and culinary fats. In modification of vegetable oils, together with alteration of consistency, tale placed accumulation of trans isomerizes fat acids in composition of fat products. This acids has influence on nourishing value and assimilation of fat acids. In work it was researched means of decrease of content of trans isomerized fat acids in catalysis modification of vegetable cotton-seed oil. The processes of catalysis saturation and among molecule interesterification

of fat raw materials were designated as methods of

modification. It was determinated, that accumulation of trans acids depends on technological regime of realization catalysis modification, mature and composition of used catalyst and method of realization of technological processes. Increasing temperature and pressure of process results increasing the content of trans isomerizes fat acids in oil. Using of stationary catalysts allowing to regulate content of these acids in products. Promoting of stationary catalysts with rhodium and vanadium results an abrupt decrease of content of trans acids in oils. Using the technology of among molecule interesterification of hydrogenated fats supports decrease of trans acids content too. Thus, defined principal directions and scientific proved questions about increase of quality and food value of processing products natural vegetable oils.

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ON PHARMACOLOGICAL PROPERTIES OF “ROMETIN” PREPARATION K. Zh. Rezhepov, Kh. L. Ziyaev and D. S. Kazantseva A. S. Sadykov Institute of Bioorganic Chemistry of AS RUz, 100125, Tashkent, Uzbekistan, Mirzo Ulugbek str., 83, E-mail: [email protected]

The study of total action and acute toxicity of “Rometin” preparation was conducted on white mice of both sexes with body weight of 18-22 g. “Rometin” was introduced intraperitoneally at doses of 100-2000 mg/kg. Observations for the first 4 hours showed that the introduced doses of preparation caused decrease in moving activity of tested animals, the reactions on noise and pain were unaffected. Respiration was rhythmic; the closure of eye lids was detected. Increase of preparation dose up to 400 mg/kg caused suppression of moving ability, which lasted for more than 2 hours. In 24 hours after single intraperitoneal introduction of “Rometin” no change in behavior and general state of tested mice was detected. Animals ate fodder and drank water very well. Preparation in a dose of 2000 mg/kg also didn’t cause considerable changes in behavior and general state of tested mice comparatively to intact ones. Death was observed neither in 4 hours, nor in 14 days. Based on results it can be suggested that “Rometin” preparation is low toxic, since it’s toxic at the dose of more than 2000 mg/kg at single intraperitoneal administration. After long-term (30 days) perioral introduction of “Rometin” preparation in doses of 50 mg/kg, 100 mg/kg and 200 mg/kg it didn’t cause pathological changes in morphological composition of peripheral blood, it didn’t affect diuresis and liver function.

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IR-SPECTROSCOPY FOR ANALYSIS AND STANDARDIZATION OF GOSSYPOL DERIVATIVES K. Zh. Rezhepov, Kh. L. Ziyaev, A. I. Ismailov, A. M. Ermatov A. S. Sadykov Institute of Bioorganic Chemistry of AS RUz, 100125, Tashkent, Uzbekistan, Mirzo Ulugbek Str., 83, E-mail: [email protected]

Analysis of literal data shows that for modification of drugs in order to prolong their action and make them water-soluble the most effective way is to obtain their complexes, in particular with N-PVP. The method of preparing the complexes of gossypol derivatives with N-PVP involves precipitation of the complex in non-aqueous systems at room temperature

and constant stirring. We prepared some complexes of gossypol derivatives with N-PVP (M=8000±2000). These complexes are bright colored powder-like substances with a slightly specific odor. Gossypol derivatives interacting with N-PVP form complexes via hydrogen bonds between their functional groups. For characterization of such complexes UV spectroscopy is frequently used, though IR spectroscopy can give more information. Based on IR data the following structure for N-PVP complexes of gossypol derivatives was suggested:

R

N H

H C

OH

OH

O (

H C C H2 N H2C C H2

HC

N H

R O

)n O

OH

CH3

C H3C H CH3

CH2

H3C

OH C H3C H CH3

xy

x

x/y=9/1; n=75

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QUALITY CONTROL, STANDARDIZATION OF MEBAVIN AND ITS DRUG FORM K. Zh. Rezhepov, Kh. L. Ziyaev A .S. Sadykov Institute of Bioorganic Chemistry of AS RUz, 100125, Tashkent, Uzbekistan, Mirzo Ulugbek Str., 83, E-mail: [email protected]

The products of gossypol condensation with compounds containing active hydrogen have been synthesized by us for the first time. One of these gossypol derivatives is 2,2-di-(1,6,7-trihydroxy-3-methyl-5-isopropyl-8-haphthyliden-barbituric

acid)

and

its

complex with PVP (M=12000) called Mebavin is known as immunosuppressant. Mebavin is recommended by Pharmacy Committee of MH RUz for complete clinic investigations at Republic

Nephrology

Center

of

Tashkent

Medical

Academy

to

cure

chronic

glomerulonephritis and allergodermatitis. Individuality of Mebavine can be determined by TLC on Silufol-UV-254 plates eluting with DMSO:EtOH (1:9 (v/v)). Quantitative determination of Mebavine in the substance was conducted by spectrophotometric method. Metrological characteristics of spectroscopic determination of Mebavin at λ=495 nm correspond to the number of experiments, n=5; number of freedom degrees, f=4; average selection, Õ =0.101; dispersion S2=0.606; standard deviation S=0.505; standard deviation of average result S Õ =0.2525; Х=1.435;  Õ =1.280;   =±0.0013;   =±0.0040; P=95%; t (p, f) = 2.87. These results created a basis to write temporary pharmacopoeia articles on the standard sample of Mebavin, its substance and 0.1 g tablets.

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MEBAVIN-MEDICAL POLYMER BASED IMMUNOSUPPRESSANT K. Zh. Rezhepov, Kh. L. Ziyaev and A. I. Ismailov A. S. Sadykov Institute of Bioorganic Chemistry of AS RUz, 100125, Tashkent, Uzbekistan, Mirzo Ulugbek str., 83, E-mail: [email protected]

Different immunomodulating medicines acting as immunosuppressants such as anti-metabolites

(imuran,

azathiopyrine),

alkylating

medicines

(cyclophosphamide,

chlorbutyne), corticosteroids (prednezolone, urbazol) thymus preparations have limitations (toxicity, insufficient immunosuppressive activity and organospecificity at therapeutic doses at alias). Moreover, they are poorly available and expensive. Data on study of batriden complex with medical N-polyvinylpyrrolidone obtained by us suggest its high immunomodulating activity, low toxicity (LD50> 2000 mg/kg) and wide range of action. Comparative study of pharmacokinetic parameters of radioactive

14

С-labeled batriden

and mebavin samples revealed the increase in the rates of suction and accumulation of the latter one in immunocompetent organs, a faster and fuller removal of mebavin out of organism. On the model of transplantation immunity it has been shown that mebavin causes the dermal grafts’ establishment of up to 29.3±2.63 days in contrast to that of control one, which is up to 7.8±0.52 days. The above-listed data suggest the possibility of developing a new low toxic, effective medicine on base of mebavin for curing autoimmune diseases.

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WATER–SOLUBLE COMPLEXES OF GOSSYPOL DERIVATIVES K. Zh. Rezhepov, Kh. L. Ziyaev A. S. Sadykov Institute of Bioorganic Chemistry of AS RUz, 100125, Tashkent, Uzbekistan, Mirzo Ulugbek Str., 83, E-mail: [email protected]

Among limitations of medical preparations created on the basis of gossypol is their insolubility in water. One of the methods to make them water-soluble is complexation with polymer. As a polymer component N–polyvinylpyrrolidone (N–PVP) has been used, and some of gossypol derivatives complexed with N-PVP have been studied. The derived complexes are colored, powder-like substances, soluble in water. The study of interferon-inducing activity of the obtained complexes demonstrates increase in their efficiency in comparison to that of insoluble derivatives of gossypol in the same conditions. Preparation of water–soluble complexes of derivatives of gossypol causes the increase in their bioavailability, efficiency at lower doses and decrease in toxicity in comparison with initial compounds. We developed different medical preparations on the basis of water–soluble derivatives of gossypol. A complex of ragosin with N–PVP, named gozalidon, is recommended for wide medical application against Chlamydia infections in the form of 0.1 g tablets. Mebavin, a complex of batriden with N–PVP, which has been found to be effective against chronic glomerulonephrite is undergoing clinical studies

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DETERMINATION OF 6-NITRO-2,3-POLYMETHYLENE-3,4-DIHYDROQUINAZOLI NE-4-ONES BY HPLC METHOD I. Kh. Ruziev1, N. I. Mukarramov2, N. K. Mukhamadiyev1, Kh. M. Shakhidoyatov2 1

2

Samarkand State University, E-mail: [email protected], Institute of the Chemistry of Plant Substances named of academician S. Yu. Yunusov AS RUz, Tashkent, fax (99871) 1206475, E-mail: [email protected]

This report is devoted to optimization of process of division 6-nitro-2,3-tri (tetra-, -penta)methylene-3,4-dihydroquinazoline-4-ones by method HPLC. Research was carried out on liquid chromatography "Agilent-1200" with the software. As a dividing column used standard chromatographic columns filled with sorbent C-18. As a mobile phase we use a mix of solvents - acetonitryl, methanol and water with a variation of quantitative structure. As the registrar of signals used diode matrices detector. The

optimum

condition

of

division

6-nitro-2,3-tri(tetra-,

penta)methylene-3,4-dihydroquinazoline-4-ones is established: elution – water : acetonitryl : methanol = 64 : 35 : 1. Speed of a mobile phase – 0.75 mL / min. Length of a UV wave of the detector (Figure).

Fig. Chromatography of nitroquinazolones-4 mixes On the basis of the received data it is possible to ascertain, that found optimum conditions are provided with high efficiency (N=3287; HPTT = 0.03 mm) and selectivity (=1.48) under the relation 6-nitro-2,3-polimethylen-3,4- dihydroquinazolin-4-ones and completeness of division (Rs=6.75). Duration of division is 8 minutes. · 154 ·

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HPTLC VERSUS TLC G. Sabira,b, G. E. Morlockb a

Xinjiang Institute of Chinese Material Materia and Ethnodrug, Urumqi, 830002 b

Institute of Food Chemistry, University of Hohenheim, Stuttgart, Germany

Planar chromatography in the analysis includes the area of chromatographic procedures, using as a planar stationary phase medium. These include thin-layer chromatography (TLC), high-performance

thin-layer

chromatography

(HPTLC)

and

the

ultra-thin-layer

chromatography (UTLC). The TLC is due to their simple embodiment of the internationally most widely used method. The UTLC is related to the development of nanostructures coatings and office chromatography[1] is still in its infancy. The TLC is currently the most powerful version. It stands for the use of more powerful and advanced coatings and devices of automation of individual steps[2]. Analytical problems with the HPTLC to address effectively require that all instruments will be used optimally. Compared to TLC, the HPTLC well provides a quantitative cost-effective alternative[3,4]. What are the HPTLC advantages compared with TLC offers is outlined with examples from the field of food analysis. The comparison of sugars and dyes analysis by HPTLC or TLC clearly demonstrates the difference between the two methods[5]. In the analysis of food provides the HPTLC, not the TLC, a valid and powerful analytics. Often no distinction between these terms, do not know the difference. This acceptance of HPTLC difficulty is homemade, and the TLC stands in the way of HPTLC: the principle is planar without any device, even without electricity, simply and quickly explained on the state 50 years ago in the worldwide average of 5 min. This early imprinting on easy, only qualitative method without in-depth knowledge is deep and has economic consequences later. We move forward! REFERENCES

1.

G. E. Morlock, C. Oellig, L. W. Bezuidenhout, M. J. Brett, W. Schwack. Anal Chem. · 155 ·

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82(7), 2940-2946 (2010). 2.

A. Zlatkis, R. E. Kaiser (Hrsg.), HPTLC: High Performance Thin-Layer Chromatography, Elsevier Scientific Publishing Company, Amsterdam, p. 11 (1977).

3.

G. E. Morlock, W. Schwack. J. Planar. Chromatogr 20, 399 (2007).

4.

G. E. Morlock, W. Schwack. LCGC Eur. 366 (2008).

5.

G. E. Morlock, G. Sabir. J. Liquid & Rel. Techn. 34(10), 902-919 (2011).

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INFLUENCE OF CHITOSAN ON THE STATE OF GASTRIC AND INTESTINAL MUCOSA IN EXPERIMENTAL HEPATITIS R. A. Sabirova, M. U. Kulmanova, R. Yu. Milusheva Tashkent Medical Academy, Uzbekistan

A drug chitosan has a high adsorption activity at its transition from soluble to colloidal state in the duodenum where the environment is gradually changing from acid to neutral and slightly alkaline. Absorption properties of aqueous suspension of purified chitin show that the product may absorb from plasma average molecular weight peptides, creatinine, urea, cholesterol, threeacylglycerides, and K+ ions [K. S. Helmer. et. al., 2002]. In the intestinal lumen, transport of substances to the sorbent occurs by facilitated diffusion by concentration gradient and due to convection currents supported by the intestinal peristalsis. The forming of wall surface of the sorbent layer is also possible [I. N. Bolshakov. et al., 2003]. In our study, we compared the effect of chitosan in comparison with cinariks on the state of gastric and intestinal mucosa in the development of chronic heliotrine hepatitis. Chronic toxic hepatitis (CTH) was reproduced by oral administration of a similar heliotrine solution in a dose 50 mg/kg (5 mg of heliotrine per 100 g geliotrina) of body weight once a week for 42 days. Pharmacotherapy was carried out on the 50, 80 and 110 days of experiment in the next 10 days. Cobalt chitosan of silkworm was injected in a dose of 25 mg/kg, and cinariks – 0.017 mg/kg of body weight. 4 months later, after 10-day treatment both drugs significantly increased the hexosamine content in gastric and intestinal mucosa up to 12 and 8 (chitosan) and 11 and 7.4 mg/mL (cinariks), respectivly. Chitosan increased the initial parameter of hexose in 1.25 times in both fluids, respectively. Apparently, chitosan effect on the protective barrier of gastric and intestinal mucosa is based on its chemical structure - a copolymer of D-glucosamine and N-acetyl-D-glucosamine. Depending on the deacetylation reaction efficiency, chitosans with

different numbers of deacetylation (80-90%) are obtained. Deacetylation number shows the percentage of D-glucosamine in chitosan molecule. Compared with cinariks, the most significant antioxidant effect of chitosan was shown in the 90 (stomach) and 120 (intestine) days of experiment. Superoxide dismutase activity in intestinal and gastric mucosa was · 157 ·

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significantly increased after use of chitosan, especially at the 90 day of experiment. Both drugs equally increased catalase activity in gastric mucosa, whereas in intestinal mucosa the effect of chitosan was more significant, especially by the end of experiment. Chitosan more significantly increases the phospholipid content, reduces the activity of phospholipase A2 in gastric and intestinal mucosa than cinariks. The cholesterol content in gastric mucosa after treatment with both drugs varies in waves: after 2 months it normalizes, by the 3 month it increases, but by the end of experiment again comes back to normal. Thus, studies have shown the benefits of chitosan before cinariks. Chitosan by binding ions may break off the chain at the stage of initiation of oxidation and inhibit the intensification of lipid peroxidation. Activation of antioxidant enzymes indicates the balance of antioxidant pool in the body and ending of membrane-destructive processes, as well as restoration of structural components of gastric and intestinal mucosa.

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IN CREASING THE QUALITY OF CEREALS AND CEREALS PRODUCTS WITH USAGE OF CONCENTRATE

FROM

BLOSSOMS OF ROSE. S. S. Saidvaliyev, A. M. Raximov, K. X. Majidov, M. N. Raximov Bukhara Engineering-Technical Institute of High Technologies. 200017 Bukhara, Republic of Uzbekistan, Fax:+(36522)36197,e-mail:[email protected] Open Joint-Stock Company "Tashkent yog’-moy” 1000000 Tashkent city, Republic of Uzbekistan Fax: (3712) 965702. E-mail: [email protected], e-mail:[email protected].

National cereal products of Uzbekistan are characterized with high nourishing value “Shirmoy bread” takes an important role among the other products “Shirmoy bread” is prepared from the grain wheat flour of 1st sort, with using pressed yeast, baking salt, anis sugar sand, lamb fat pea flour and

water. To increase the quality and

organoleptic

property of this land of product, We added to its ingredients a concentrate , which is got from local blossoms of rose. The concentrate was reached by the way of gradual concentrating and boiling of rose liquid was used. Inserting of the concentrate was done in the order of 1….3% from the weight of prepared production. Instead of liquid a mix of the bread product was implemented by traditional technology. For getting comparison analysis of the physic- chemical and organoleptic numbers the products were prepared both with and without adding of the concentrate or the liquid. In the ready products was determined its presentation, surface, forms and sizes, color, bared ness, taste and smell. The received results showed that, the experienced samples of the bread are higher than the control samples, which were prepared by the eating reception. The experienced products characterized a nice taste and smell. The received results allowed to conclude that, inserting of new kinds of addling to the uzbek bread, lets to get a ready product completely satisfying and even surpassing the demands of actual standarts. This determines opportunities of using of products of recycled rose blossoms in new directions.

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SYNTHESIS AND PHYSIC-CHEMICAL CHARACTERISTIC2-METHYLTHIO-4H(SUBSTITUTED) AMINOQUINAZOLINES F. E. Saitkulov, Kh. M. Shakhidoyatov A. Navoiy Samarkand State University, University Avenue 15, Samarkand, Uzbekistan E-mail: [email protected]

In relationship with presence of N3 = C4 = NН- fragments which possible consider as amidine system, molecule of 2-substituted 4-aminoquinazolines can exist in different tautomeric forms, as a result isomerization of double bonds N3 = C4 = NН with formation fragment N3H= C4 = N -. For the reason clarifications of the possibility such tautomeric conversions we take as object 2-methylthio-4H(substituted) aminoquinazolines. These compounds are synthesized in several stages on scheme: O

O COOH

N

NH4SCN NH2

N

1

2

Cl N N 4

H

H

H

N

S

POCl3 SCH3

3

NHR N

RNH2 SCH3

N

CH3I

N 5

SCH3

a ) R = H; b ) C6H5; c ) C6H4 CH3 4; d ) C6H4 OCH3 4; e ) C6H4 NO2 4

Interaction of 2-methylthio-4-chloroquinazoline (4) with ammonia, aniline, p-toluidine, o-anisidine and p-nitroaniline brings to formation the compounds 5а-е with good yields. Investigation UV-spectrum of alcohol solution 5а-е in neutral, alkaline and acid medium shows that essential changes in alkaline medium does not occur. In acid medium are observe displacement of the absorption band in the field of 254 nm in 265 nm, which indicate on protonation of nitrogen N-1 atom and impossibility deprotonation in alkaline medium. Individuality, purity and structure 5а-е are confirmed by TLC, IR, 1H NMR - and mass-spectrum. There are absorption bands at 1614-1616 cm-1, 1595-1598 cm-1, 1552-1554 cm-1, 1509-1512 cm-1 characterizing N1 = C2 - and N3 = C4 - groups in IR-spectrum. In their mass spectrum the intensive molecular ions and fragments of disintegration were observed. · 160 ·

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MICROELEMENT COMPOSITION OF BIOLOGICALLY ACTIVE ADDITIVE Ver-Mol-2 O. Kh. Saitmuratova , F. T. Yakubova, J. Kutliev, N. J. Sagdiev Institute of bioorganic chemistry named after A. S. Sadikov, Academy of Sciences of Uzbekistan Tashkent Pediatric Medical Institute of Uzbekistan Institute of Microbiology Academy of Sciences of Uzbekistan, Tashkent

Trace elements play an important role in determining the structure of milk proteins; affect the quantity and nutritional value of dairy products. So, as contained in the milk of trace elements (especially Cu, Fe, Zn, Ni) can be catalysts for some chemical reactions, the lack of them leads to various pathological changes in the body. Previously, we prepared a biologically active supplement Ver-Mol-2 based on animal products and show that it is good enough antidiabetics. The advantage of Ver-Mol-2 is that it does not cause allergic reactions, is a cheap and easily digestible product and has no side effects. The purpose of this study was to determine the trace element composition Ver-Mol-2 for further standardization of the product. Trace element composition of Ver-Mol-2 is defined neutron-absorption method. Found that in the Ver-Mol-2 are the following trace elements: chlorine - 0,87% Sodium 0.48%; bromine - 26 micrograms / g of iron - 77 mg / g, zinc - 33 mg / g cobalt - 0.01 micrograms / g selenium - 0.1 micrograms / g, Chromium - 0.1 mg / g; Mercury - 0.01 mg / g; antimony - 0.91 micrograms / g cadmium - 0.1 mg / g. Thus we have established trace element composition of Ver-Mol-2. It should be noted that in the Ver-Mol-2 among more micronutrients iron and zinc by several times compared with cows milk.

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NEUROPROTECTIVE AND ANTI-ISCHEMIC EFFECTS OF POLYPRENOL-CONTAINING DRUG ROPREN P. D. Shabanov, V. S. Soultanov Military Medical Academy, 6, Acad. Lebedev street, st. Petersburg, 194044, Russia; E-mail: [email protected]; Solagran Ltd, Level 1, 480, st. Kilda Road, Melbourne 3004, Victoria, Australia; E-mail: [email protected]

Ropren®, a 95% concentrate of polyprenols, isolated from fresh green needles of European fir (Picea Abies L. Karst) is recommended as a hepatoprotective medication of plant origin. This paper presents data on the anti-ischemic and energy-stabilizing effects of Ropren in ischemia of the brain in rats. The rats were anesthetized with nembutal, both common carotid arteries were ligated and for 7 days they were injected daily with Ropren i.p. at doses 4.3 or 11.6 mg/kg. An hour after the last injection neurological status of ischemic animals was assessed using the McGraw scale and the concentration of creatine phosphate (CP), adenine nucleotides and energy charge, lactate and pyruvate in brain tissue was estimated. The nootropic drug Piracetam (200 mg/kg) was used as the comparator. The treatment resulted in a marked improvement of the neurological status of ischemic animals, normalization of brain energy metabolism and decrease of lactic acidosis. Following the usage of Piracetam on the 7th day after occlusion of arteries 67% of rats survived, as with Ropren – 56% (4.3 mg/kg) and 63% (11.6 mg/kg). Cerebral ischemia led to significant depletion of the energy resources of the brain. The content of macroergs sharply decreased (ATP, CP), the number of unoxidized products (ADP, AMP, lactate) increased, the energy charge decreased and lactic acidosis developed. The latter is due to a 5-fold increase in the level of lactic acid in the brain. In these cases Piracetam decreased lactic acidosis only by 46.5% and Ropren by 62% at 11.6 mg/kg respectively. The same dosage of Ropren increased the CP content by 73% (Piracetam – by 60%) and ATP concentration in brain tissues by 173%. Both Ropren and Piracetam affected the level of ADP quite similarly, lowering it by 40-43%. Thereby, both Piracetam and Ropren normalised the energy charge, reflecting the general state of energy metabolism in the brain. The results demonstrated the neuroprotective and energy-stabilizing effects of Ropren in ischemia of the brain.

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SUCCESSES IN THE FIELD OF PYRIMIDIN-4-ONES, CONTAINING POLYMETHYLENE CHAINS IN THE 2,3-POSITIONS Kh. M. Shakhidoyatov, B. Zh. Elmuradov Institute of the Chemistry of Plant Substances, Academy of Sciences, Republic of Uzbekistan, Mirzo Ulugbek str., 77, Tashkent; Fax: 998-71-120-64-75; E-mail: [email protected]

Pyrimidine ring is part some many natural (alkaloids, nucleic acid, antibiotics etc.) and synthetic (furo-, thieno-, pyrrolo-, pyridopyrimidines etc.) compounds. During 30-35 years in the Institute of the Chemistry of Plant Substances (ICPS) large-scale research in the field of benzopyrimidines (quinazolines), thieno- and pyridopyrimidines, for revealing laws of passing of reactions, creation of new high effective drugs is carried out on the basis of readily available substances. Therefore, studying of reactions condensed pyrimidinones is very perspective [1-3]. Besides pyrimidinones, containing methylene chains in a 2,3-positions, are very interesting objects for developing of the methods of synthesis of the new potentially active derivatives and also buildings of drugs for the blessing of people. With this purpose, we in this work generalized results received by us. As object we used polynuclear thieno- (1) and benzopyrimidinones (2): O R R1

O N

S

R2

N

(CH2)n

N

(CH2)n

N R3

1, R=R1=alkyl; R+R1=(CH2)m; n=1-4; m=3-5

2, R2=R3=H, Br, NO2 n=1-4

In the present report, we carry out the reaction of 1 and 2 with electrophilic compounds: aldehydes, ketones, acid chlorides and etc.

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REFERENCES

1. A. Lilienkampf, S. Heikkinen, I. Mutikainen, K. Wähälä. Synthesis 2699 (2007). 2. K. Csukonyi, J. Lazar, G. Bernath, I. Hermecz, Z. Meszaros. Monatsh. Chem. 117, 1295 (1986). 3. Kh. M. Shakhidoyatov. Quinazol-4-ones and Their Biological Activity, Tashkent: Fan. 99-104 (1988).

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DESIGN AND SYNTHESIS OF ISOFURANODIENE DERIVATIVES C. Q. Shang, L. Y. Du, Y. L. Wei, X. Y. Sun, Y. K. Guan* School of Pharmacy, Yantai University, Yantai, Shandong, 264005, China E-mail: [email protected]

Isofuranodiene as one of furanosesquiterpenes, which was isolated from the essential oil of the rhizome of Curcuma wenyujin, has been proved to have remarkable antitumor activity in vitro and in vivo. However, chemical lability of this molecule in air or heat exposure, to a

large extent, limits its clinical application. So, the issue how to improve its chemical stability definitely constitutes the key topic for the further biological application of isofuranodiene and its analogues. Importantly, the instability of isofuranodiene is probably due to the undesired Diels-Alder type addition of furan diene moiety in the presence of oxygen. To address this topic, a series of isofuranodiene derivatives bearing the electron withdrawing group at the C-2 position of the furan moiety, 1, 2, 3a~3d and 4a~4d were designed and synthesized. Currently, the antitumor activities of these derivatives are under evaluation.

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COMPLEXING PROPERTIES OF CROWN-ETHERS INDUCING A "CHANNEL" CONDUCTANCE OF THE BILAYERS U. T. Sharafutdinova, U. Z. Mirkhodjaev, A. K. Tashmukhamedova, B. A. Tashmukhamedov Department of Biophysics, National University of Uzbekistan, 100174, Vuzgorodok, Tashkent, Uzbekistan Е-mail: [email protected]

We have shown previously that sulfo-derivatives dibenzo-18-crown-6 (DB18K6) can induce "channel" conductance of the bilayers for various cations [1]. It was studied the interaction of sulfo-DB18K6 with conductometric method +

+

[2]

as

2+

functional analogues of natural modifiers of the membranes with the ions K , Na , Ca . The coupling constants (K) and Gibbs free energy (ΔG) were calculated in water and in ethanol. It was shown that the constant of complexation of crown ethers exhibit channel-forming activity in bilayers in order of magnitude smaller than that of crown ethers exhibit chelating properties of ionophorics. The results of conductometric studies show that for all investigated sulfo-derivatives are not stable complex formation. This gives grounds to conclude that the nature of the substances studied not ionophoric and indicates their ability to change the conductivity of the membrane bilayers to form ion-transporting structure. REFERENCES

1. O. V. Yarishkin, U. Z. Mirkhodjaev, A. K. Tashmukhamedova, B. A. Tashmukhamedov. J. Inclusion Phenomena and Macrocyclic Chemistry Vol. 49, 139-144 (2004).

2. I. M. Andreev, G. G. Malenkov, A. M. Shcrob, M. M. Shemyakin. Molecular Biology 3, 614-623 (1971).

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CLASSIFICATION OF PREDIABETES AT THE INTERSECTION OF MODERN MEDICINE AND THE MEDICAL SYSTEM OF IBN SINA M. Y. Sharofova, Yu. N. Nuraliyev The International Institute for the Study of Ibn Sina (Avicenna) and Pharmacology Tajik State Medical University named after Abu Ali Ibn Sina

Abu Ali Ibn Sina (Avicenna) considered diabetes as a renal disease. He linked the cause of diabetes to the formation of an unknown matter in the body and with the sharp change of mizaj (nature) of man into the cold, i.e., into the acidic (Yu. N., M. Y.) side. Avicenna strictly warned at diabetes it should be treated the kidneys and the liver with a mandatory cleansing of “inside” (“endo”), i.e. cleaning the inside or body fluids. Based on the foregoing, the basic strategy of treatment of diabetes by Ibn Sina was aimed at restoring impaired renal and liver function, and cleansing the liquid medium, i.e. the endothelial system of the body. The medicine of the scientist era has absolutely known nothing about the leading role of the pancreas and insulin in the pathogenesis of diabetes. After recognition of the role and the importance of disorders of the β-cells of the pancreas as the main pathogenetic mechanism of diabetes, the teachings of Ibn Sina on diabetogenesis were recognized incorrect. Because of this, the modern medicine entirely rejected the tested over many centuries of experience of internationally recognized scholar on the problem of diabetogenesis, as well as the tactics of treatment of diabetes. Continued growth of type 2 diabetes worldwide and a high degree of disability and death from this disease served as the scientific justification at the junction of the achievements of modern medicine for the study of practical recommendations, hypothesis and ideas of Avicenna on the issues of pathogenesis, therapy and prevention tactics of diabetes. To solve our goal as a primary source were used: Book Three, Volume 2 of “Canon of Medicine” which provides information on the issues of etiology, pathogenesis and treatment of diabetes; the first book, devoted to the general rules of medicine and therapy; the second to simple medicines and the fifth book, devoted to complex drugs. As the evidence base it was used recent advances in modern medicine, dedicated to insulin resistance, prediabetes, · 167 ·

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metabolic syndrome, as well as treatment of diabetes with synthetic and hormonal medications. In this paper, on judgments of experts are presented the results, we carried out at the intersection of modern medicine and the medical system of Avicenna, directly related to the classification of pre-diabetes. At the end of the 20th century it is appeared the notion of a state of insulin resistance and its significance in the development of prediabetes (M. I. Balobolkin. 2000; M. Matsuda, R. A. Defronzo. 1999, etc.). It was proved that in the initial stage of pre-diabetes the pancreas function is not decreased, on the contrary, even sharply increased (D. Elahi. 1996, etc.). Based on this information and the teachings of Avicenna on diabetogenesis, we believe it is appropriate to classify pre-diabetes by 2 stages: 1. Prepancreal stage of prediabetes (PSP) – while the function of the pancreas is not broken, but rather increased. 2. Prepancreal stage (PS), which in fact is a consequence and not the primary cause of prepancreal stage of prediabetes. Prepancreal stage of pre-diabetes, in the frame of teachings of Ibn Sina on diabetes and appointed by the great healer the strategies of diabetes treatment and on the results of the achievements of modern medicine, was divided into 3 types: ■ PSP of prediabetes of renal aetiology, which develops in the background of renal dysfunction under the toxic effect of uric acid, uric acid salts - urate and its metabolites, especially alloxan; ■ PSP of prediabetes of hepatic etiology, such as steatosis of the liver, in the background of which in the blood it rises sharply the level of lipid peroxidation products, free radicals, atherogenic lipids and other biotic diabetogenics; ■ PSP of prediabetes of endothelial aetiology, which develops as a result of intoxication of internal environment of the body, i.e. endothelial system by various endogenous and exogenous diabetogenics, particularly by nitrates, metabolites of nitric oxide (NO) and other biotic and abiotic factors. Thus, at pre-diabetes it will be affected the total endothelial system and the endothelial system of the kidneys and the liver. In general, it emerges such a pattern: prediabetes - is continually progressing process with many interrelated with each other etiologic and pathogenetic mechanisms encouraging in general the atrophy of the β-cell islets of Langerhans, hypofunction of the pancreas, the development of the true picture of of type 2 diabetes of varying degree of severity. Relapses and vascular complications (retinopathy,

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macroangiopathy, diabetic foot, etc.), observed in severe forms of diabetes in many cases related to the lack of adequate therapy of prediabetes. Based on an analysis of the teachings of Ibn Sina on diabetogenesis, as well as the achievements of modern medicine we can say that type 2 diabetes is the consequence of untreated pre-diabetes. Without pre-diabetes there is not type 2 diabetes; and without reliable therapy there cannot be effective treatment of pre-diabetes diabetes, stopping its recurrence and prevention of vascular complications! Avicenna’s wisdom concluded in that he was treating pre-diabetes, and not the consequences of pre-diabetes. To this end, he treated the kidneys and the liver. He recommended his patients cleansing therapy aimed at cleansing the “inside”, i.e. the liquid medium or endothelial system. Ibn Sina did not treat the consequences of pre-diabetes, because then the human race and the medicine did not know anything about the role and significance of pancreatic and the importance of insulin in the development of diabetes. Modern medicine in contrast to Ibn Sina and traditional medicine treats not pre-diabetes, but the consequences of untreated pre-diabetes associated with pancreatic dysfunction and insulin deficiency. Therefore, with such tactics of therapy of diabetes the diabetogenesis process does not stop. For this reason, in the background of the temporary improvement of the patients there emerge new more severe relapses of diabetes. Continued growth of type 2 diabetes worldwide in our view confirms that the pancreatic-insulin mechanism of pathogenesis of diabetes covers incompletely the urgent issues of tactics of therapy and prevention of this disease. Modern medicine needs new ideas and hypotheses, the new strategy of therapy, allowing on the level of pre-diabetes to stop the growth and the development of diabetes. To stop growing rise of type 2 diabetes worldwide is not possible without deliberate tactics of therapy and the development of new methods for prevention of pre-diabetes as a major constantly progressing pathogenetic mechanism of the development of diabetes, its recurrence and vascular complications. We are confident that the rational use of age-old experience of traditional medicine in combination with the achievements of modern endocrinology may well complement each other and become a reliable weapon of modern medicine in the fight against this most common disease of the century!

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THE NEW ORIGIN OF CAMPHOR AND 1,8-CINEOL (EUCALYPTOL) OF THE ESSENTIAL OILS OF SOME ARTEMISIA SPECIES FROM MONGOLIAN GOBI-DESERT S. Shatara, Sh. Altantsetsega, N. Javzmaaa, Ch. Nyamsaikhana L. D. Radnaevab, S. V. Zhigzhitzhapovab a

Institute of Chemistry and Chemical Technology of the Mongolian Academy of Sciences Ulaanbaatar, Mongolia. Е-mail: [email protected] b

Baikal Institute of Nature Management. SB RAS. Ulan-ude, Russia

There are 103-106 Artemisia species in Outer Mongolian Forest-Steppe and Gobi-Desert, which grown wild in many regions1. Artemisia is a perennial Asteraceae of the Outer Mongolian regions, which has been used for centuries as spice, home remedy, drug, perfume and insecticide. In medicine, it is used as antispasmolytic, antibacterial, antifungal, secrotolytic, expectorant, anticeptic, anthelmintic and antitusive as reported by other authors2-5. The hydro distilled essential oils obtained dried plants materials were analyzed by GC-MS. The results of the essential oil composition analyses are presented in Table 1. Table 1 New origin for Camphor and 1,8-cineol contain Essential Oils of some species

Borneol

A.mongolorum

52.1

21.5

t

t

t

t

t

73.6

2

A.intricata

50.0

15.4

t

t

3.0

0.6

t

69.0

3

A.gmelinii

40.9

20.7

t

t

t

4.8

7.0

73.4

4

A.subchrysolipes

35.9

11.8

14.9

20.0

3.1

3.8

1.0

78.7

5

A.frigida

35.0

27.0

t

t

4.5

3.0

3.1

72.6

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%

Terpineol

1

Content,

1,8-Cineole

Thujone

4-ol

Compounds

Terpinene-



Camphor

Artemisia from Mongolian Desert-Gobi 3-5

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6

A.xerophytica

31.0

13.4

t

t

6.1

1.5

8.1

60.1

7

A.obtusiloba

30.0

4.5

3.9

1.0

3.5

t

t

43.5

8

A.anethifolia

26.0

1.2

10.1

4.4

t

t

5.1

45.8

9

A.schischkinii

22.1

4.4

2.8

0.9

6.7

3.4

0.1

40.4

10

A.rutifolia

21.7

25.1

-

-

3.5

1.6

0.7

52.6

11

A.sericea

18.0

25.9

-

-

2.8

1.1

22.5

70.3

12

A.gobica

15.5

18.5

22.5

3.7

-

-

-

60.2

13

A.caespitosa

12.6

31.1

7.3

1.3

-

8.1

-

60.4

14

A.davajamtsii

8.5

28.8

6.8

12.9

t

5.8

t

62.8

15

A.schrenkiana

5.4

30.0

19.3

19.4

-

-

-

74.1

REFERENCES

1. I. A. Gubanov. Conspectus of flora of Outer Mongolia, Moscow, (1996). 2. T. P. Berezovskaya, et al. Wormwood in Siberia, Novosibirsk: Nauka, (1991). 3. S. Shatar, Sh. Altantsetseg. The chemical components and technical character of the essential oils of Artemisia species in the Outer Mongolian territory, Ulaanbaatar, (2011).

4. International studies on the essential oils/bioactive constituents of aromatic and medicinal plants from the Mongolia. Editors: S. Shatar, N. Tsevegsuren. Ulaanbaatar, Mongolia, (2011) (in English). 5. S. Shatar. Chemical investigation of essential oil from Mongolian flora, Issue 1, Ulaanbaatar, (1998) (in English).

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HSCCC: AN APPROACH TO ISOLATION AND PURIFICATION OF THE HIGHLY POLARITY COMPONENTS FROM SPHALLEROCARPUS GRACILIS M. R. Shia,b, Z. F. Fenga,b, D. L. Dia,* a

Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese

Academy of Sciences, Lanzhou, 730000, P. R. China; Tel.: +86 931 4968248; Fax: +86 931 8277088; E-mail: [email protected]. b

Graduate University of the Chinese Academy of Sciences, Beijing 100049, P. R. China

The highly polarity components in the extract of natural products were difficult to isolate and purify by the silica gel column technique. In the previous paper, sephadex gel chromatography and preparative HPLC were usually used to isolate and purify the highly polarity compounds from natural products. Ascribed to many disadvantage of above mention methods, such as consuming much time, expensive cost of material and low preparation scale, those methods were difficult to scale-up preparation. Based on the advantages of high efficiency, high recovery and easiness to scale-up preparation, High speed counter-current chromatography (HSCCC) technique have been widely used for the preparative isolation and purification of various constituents from natural products. Compared to silica gel column chromatography, HSCCC was a process of liquid-liquid extraction, the preparative isolation and purification of maximus polarity compounds from natural products is prospective. In this study, a simple and reliable method based on high-speed counter-current chromatography (HSCCC) technique was successfully established for isolation and purification of polar compounds from the n-butanol fraction of the rhizome. Based on the partition coefficient values (K) of polar compounds, an optimized solvent system consisted of ethyl acetate: n-butanol: water (1:4:5), was selected for the HSCCC separation. In single injection, compounds 1 (6.8 mg), 2 (8.1 mg) and 3 (6.3 mg) with the purities of 98.1%, 96.3% and 97.7% were yielded from 300 mg of the crude extract. The structures of compounds were identified by spectroscopic methods. Comparison with the reported data, the compounds were identified as 4′-O-β-D-glucopyranosyl-5-O-methylvisamminol,

4-methylumbelliferyl-β-D-glucopyranoside · 172 ·

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5-sucrosyl-8-methoxy-2H-1-benzopyran-2-one. Acknowledgements

The National Natural Sciences Foundation of China (NSFC No. 20974116) and the “Hundred Talents Program” of the Chinese Academy of Sciences (CAS).

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SYNTHESIS OF NEW HYDRAZONES OF EPIANDROSTERONE AS POTENTIALLY BIOLOGICALLY ACTIVE AGENTS M. Sikharulidzea, N. Nadaraiaa, MegiKakhabrishvilia, N. Barbakadzea, R. Melik-Ohanjanianb a

Tbilisi State Medical University Iovel Kutateladze Institute of Pharmacochemistry, 36 P. Sarajishvili Str., 0159, Georgia. b Scientific-Technological Center of Organic and Pharmaceutic Chemistry, Academy of Science of Republic of Armenia, 26 Azatutyana Ave., 0014, Armenia

One of the most prospective approaches for designing new compounds possessing high therapeutic effect seems to be modification of natural compounds of plant origin by enriching them with pharmacophore groups. The new hydrazones of epiandrosterone were synthesized on the basis of natural steroidal sapogenin tigogenin (from plant Yucca glorioza, cultivated in Georgia). Synthesis was performed by condensation of 3β-hydroxy-5α-androstan-17-one with hydrazides of o- and p-benzyloxybenzoic acids, benzofurane and furan-2-carbon acids and 2-hydrazinoimidazole with iodinehydrate in ethanol in presence of catalytic amount of acetic acid. R

O ethanol/CH 3COOH HO

HO

2-6

1

3 R= N NH C O

2 R= N NH C O C6 H5 H 2CO

OCH2

N 4 R= N NH C O

O

5 R= N NH C O

O

6 R= N NH C O

N H

The structures of the all newly synthesized compounds 2-6 were confirmed by spectral analyses. Biostructures were transferred to USA, in order to examine their antitubercular and antiviral activities in the frame of programs TAACF and AACF. The work has been conducted by the support of Shota Rustaveli National Science Foundation (Project #GNSF/ST08/4-406). · 174 ·

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DETERMINATION OF THE CONTENTS OF LUTEOLIN AND APIGENIN IN APIUM GRAVEOLEN L. BY HPLC SIMULTANEOUSLY L. Sun, L. Meng, H. Yimamu Pharmacy college of Xinjiang Medical University, Urumqi, Xinjiang 830011 Apium graveolens L. (celery) was a plant of Umbelliferae and. have been used as a

herbal medicine since ancient times. It also was a favorite edible plant [1,2], known as the "kitchen of Chinese herbal medicine". The flavonoids especially for luteolin and apigenin were the main active ingredients in the Apium graveolens L.[3-5], which had the effect on antioxidant, sedative, analgesic, anti-hepatitis, blood pressure-lowering, lipid-lowering anti-tumor. Thus, study on the flavonoids in the celery has higher value and a great significance. In the present study, a method of simultaneous determination content of luteolin and apigenin was established for the quality control, development and utilization of Apium graveolen L. by HPLC[6,7]. The methodology was studied and the standard curve of luteolin and apigenin were produced, the regression equation and the linear range of luteolin were Y = - 324.06X+1801.2, r = 0.9991, 0.9332~4.9386 μg·mL



1

; Apigenin wereY = -

91.33X+564.29, r = 0.9994, 1.0269~5.0606 μg·mL-1. The peak area’s RSD of luteolin and apigenin were 2.9% and 1.7% respectively. The content’s RSD of luteolin and apigenin were 1.8% and 2.6% respectively, which indicated that the sample was stable in a day. The average recoveries of them were 99.7% (RSD=2.4%) and 99.0% (RSD=1.8%). The luteolin and apigenin in Apium graveolen L. were extracted by ultrasonic method and the contents of luteolin and apigenin were 0.22 mg·g-1 and 0.23 mg·g-1 respectively. This method was fast, simple and reproducible. It can be used to determine the contents of luteolin and apigenin and control the quality of Apium graveolen L.. REFERENCES

1.

X.-J. Song, Y.-T. Wang. The study of medicinal function of Apium graveolen L. Anhui · 175 ·

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Agricultural Sciences 36(15), 360-361 (2008).

2.

M.-G. Shen, Y. Jin,, W.-Y. Li. The chemical constituents and pharmacological effects of Apium graveolen L. Anhui Agricultural Sciences, 36(4), 1474 -1475, 1489 (2008).

3.

D.-Q. Liu, S.-R. Tang , H. Song.. Technology research of extraction of flavonoids in Apium graveolen L. by ultrasonic-microwave-assisted. Food and Machinery 26(5),

134-136 (2010). 4.

S.-M. He, J.-L. Liu. The extraction and determination of flavonoid in Apium graveolen L. Analytical Laboratory 25(8), 85-87 (2008).

5.

L. L. Pang, R.-L. Lee, L.-F. Zhou. The experimental study of Apigenin of inhibiting effect on transcriptional activator protein 3 in asthmatic mice and Th2 cytokines. Chinese Medicine 30(4), 383-387 (2010).

6.

K.-Q. Wang, J.-W., Luo, J.-P. Chen, et al. Determination of content of Apigenin in Apium

7.

graveolen L. by HPLC. Food and Machinery 25(2), 74-77 (2009).

K.-Q. Wang, J.-W., Luo, J.-P. Chen, L. Chen. Analysis of Apigenin in celery extract by HPLC and HPTLC quantitatively. Food Science 29(4), 291-295 (2008).

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SESQUITERPENE LACTONES FROM ARTEMISIA SEMIARIDA Zh.R. Smailova, B.B. Rakhimova, S.M. Adekenov JSC «International research and production holding «Phytochemistry», 100009, Republic of Kazakhstan, Karaganda, [email protected]

Three sesquiterpene lactones have been isolated from the chloroform extract of aerial part of endemic plant of Artemisia semiarida (Krasch. et Lavr.) Filat., collected in vegetation phase in Betpakdala desert of the Republic of Kazakhstan. The isolated compounds have identified as known eudesmanolides of taurine from Artemisia taurica Willd. [1], 8α –acetoxy-taurine and 8α –hydroxytaurine from Artemisia santonicum [2] and Artemisia pontica [3].

Taurine, 8α –acetoxy and 8α –hydroxytaurines from Artemisia semiarida (Krasch. et Lavr.) Filat. have been identified for the first time. REFERENCES

1.

Kechatova N.A., Rybalko K.S., Sheichenko V.I., Tolstykh L.P. Chemistry of natural compounds, 1968, №4, P. 205-207.

2.

Mericli A.H., Jakupovic J., Bohlmann F., Damadyan B., Ozhatay N., Cubukcu B. Planta Medica, 1988, 54, №5, P. 447-449

3.

Trendafilova A.B., Todorova M.N., Gussev C.V. Phytochemistry, 1996, 42, №2, P. 469-471

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INCREASING THE FOOD VALUE OF FOOD PRODUCTS WITH USAGE OF NATURAL ADDITIVES A. A. Sultanov, N. K. Majidova, K. X. Majidov Bukhara Engineering-Technical Institute of High Technologies. 200017 Bukhara, Republic of Uzbekistan, Fax:+(36522)36197,e-mail:[email protected] Open Joint-Stock Company "Buxoropaxtasanoat” 200011 Bukhara city, Republic of Uzbekistan, Fax: (36522) 23286.

Increasing quality and nourishing value have important meaning in direction of the improvement of the chemical composition and expansions of the assortment of the products of the feeding. For increasing of nourishing value and physiological characteristic of the products of the feeding use the different types of the food additives, basically got by syntetic way. The Cereal cultures consist of separate parts, which rich nutrients, vitamin and other biologically active join. Particularly, these feature possess the embryonic flakes grain wheats. Considering this, from local sort grain wheats are chosen embryonic flakes and they are used for production high-value nourishing vegetable oil. The analysis quality and estimation physiological characteristic embryonic oil have confirmed about his high nourishing value and light assimilation. So got oil is used for medical and pharmacological objectives. Oil-cakes, got from embryonic flakes after extraction of them oils also were a rich different nutrients and vitamin. So these oil-cakes after determined technological processing were used for production, cereal and confectionery products and they are carried in recipe of separate sort margarine to products. Analysis and estimation of the qualitative factors and chemical composition of the products of the feeding has confirmed about that they possessed high nourishing value, food and gustatory characteristic. On base got scientific and experimental results are determinate role of the new food additives in shaping quality and composition to finished products. Results of the studies have allowed to offer new recipes products of the feeding and realize their production on enterprise food production.

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INCREASING THE QUALITY AND IMPROVEMENT OF THE CHEMICAL COMPOSITION OF NATURAL OIL A. A. Sultanov, O. A. Akramov, N. K. Majidova, K. X. Majidov, A. M. Anvarov Bukhara Engineering-Technical Institute of High Technologies. 200017 Bukhara, Republic of Uzbekistan, Fax:+(36522)36197,e-mail:[email protected] Open Joint-Stock Company "Buxoropaxtasanoat” 200011 Bukhara city, Republic of Uzbekistan, Fax: (36522) 23286.

The association "Maslojirtabakprom", Tashkent city, Uzbekistan Quality and chemical composition of the natural butter belongs to the refining period that is to say refining. At present time

many ways of refining of cotton oil

are offered for refining of the

cottonseed oil. Used in production the refining ways of the oil of cotton are basic essential defect. In work explored and is offered in principal the new technology of refining natural oil-cotton. Essence proposed technologies is concluded consequent alkaline refining of the oil-cotton with solution aluminum

and hydracids sodium. The Realization to such

technologies raises the quality and perfects the chemical composition of the refined butter. The Studied influence to concentrations and excess of the solution aluminum sodium on reduction of the acid number, improvement color and change the quantitative contents accompanying butter-oil increase materials. It Is Installed that specified parameters reduce the contents of the free fat acids, phosphorous, gossypol and his derived in partly refined of butter-oil. This brings about significant improvement of the chemical composition and increasing of food value of the refined cotton-oil under final refining of the partial neutralized butter by solution hydro acids sodium. The Technological process proposed the refining of the cotton-oil intimidating of use in process of the neutralizations beforehand actuated in electromagnetic field alkaline solution. The Experimental studies have allowed vastly to shorten material and energy expenses, falls loss of the butter under its refining. The Results new technology are checked in working conditions and are received positive data. On base of the realization to new technology is reached increasing quality and improvement of the chemical composition of the refined cotton-oil, which suits to quality International standard.

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CHEMICAL CONSTITUENTS OF COMPOSITE MUNZIQ Z. Talata, b, H. A. Aisaa a

Key Laboratory of Plants Resources and Chemistry of Arid Zone, Xinjiang Technical

Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing South Road 40-1, Urumqi 830011, Xinjiang, P. R. China; b

Graduate University of the Chinese Academy of Sciences, Beijing, 100039, P.R. China Composite Munziq is a herbal prescription combimed by 14 medicinal herbs, namely

Glycyrrhiza uralensis, Pimpinella anisum L., Peganum harmal L., Nigella glandulifera

Preyn et Sint, Dracocephalum moldavica L., Althaea rosea L., Matricaria chamomilla L., Cichoium intybus L., Glycyrrhiza uralensis, Apium graveolens L., Cymbopogon casesius, Ocimum basilicum, etc. As a traditional Uighur medicine, it was used for the treatment of

pelvic inflammatory disease, cervicitis, allergic dermatitis, and acne. This

study

investigated the chemical constituents of Composite Munziq. The EtOAc fraction of Composite Munziq was subjected to silica column chromatography, eluted with a gradient of CHCl3–MeOH (100:0 to 60:40), then rechromatographied and purified by Sephadex LH-20 column chromatography. Two compounds were isolated from EtOAc fraction and their structures were identified as liquiritin and isoliquiritin by spectroscopic analysis. These compounds are isolated from Composite Munziq for the first time. Acknowledgements

This work was supported by China National Funds for Distinguished Young Scientists No. 30925045 and the CAS/SAFEA International Partnership Program for Creative Research Team.

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PHARMACOGNOSTIC IDENTIFICATION OF FERULA SYREITSCHIKOWII Y. Tan, T. T. Gao, Y. Ma, D. Xu, Y. H. Cheng Shihezi University of Pharmacy, Xinjiang, Shihezi 832000, China Objective: To identify Ferula syreitschikowii by identification of pharmacognosy and

provide the scientific evidence of identification and application. Methods of the original plant identification, morphological, UV spectrum identifications, microscopic identification and thin layer chromatography (TLC) were adopted. Results: There are exclusive in original plant morphology, microscopic characteristic,

UV spectrum identifications and thin layer chromatography (TLC). Conclusion: These characteristics can the scientific basis for gruffs identification of

crude drug and provide reference information for further development.

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GOSSYPOL AND GOSSYPOLONE: COMPARISON OF REACTIONS WITH NUCLEOPHILES K. Z. Tilyabaev, A. M. Yuldashev, B. T. Ibragimov A. S. Sadykov Institute of Bioorganic Chemistry of AS RUz; 100125, Tashkent, Mirzo Ulugbek Str., 83, E-mail: [email protected]

Gossypol (Gp) is a pigment of cottonseed. Its structural and biological polyfunctionality make it very interesting research object. Schiff bases produced by the SN reaction between Gp and RNH2 are found to exhibit less toxicity and pronounced bioactivity; that’s why their preparation and bioprofiling is still one of the most common approaches in Gp research. This reaction is also characteristic to gossypolone (Gpn), a Gp quinone. The preparation of its Schiff bases is of a particular interest, since it’s allowed revealing some compounds exerting high anticancer activity. For Gp and Gpn, the products of reactions with RNH2 as well as with other nucleophiles (Nu) are known. In this paper we compare Gp and Gpn reactions with Nu. The main difference in Gp and Gpn structures is that the Gp molecule has fairly acidic 1,1-OH groups that are absent in Gpn structure. By comparing the yields of Gp and Gpn SN reaction products obtained at the same conditions (same Nu agent: RNH2, 1,3-dithiane, 1,3-dithiolane; same solvent, reaction T etc.) it’s been found that the product yield is higher in case of using Gp. This fact may allow suggesting that 1,1-OH group protons of Gp molecule can affect the reaction yield possibly due to auto-catalysis via H+-transfer towards carbonyl O-atom, which increases the electrophilicity of neighboring C-atom and probability of its attack by Nu. This fact allows to consider this reaction of Gp as acid-base interaction and to revise its mechanism previously suggested.

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SYNTHESIS AND ANTITUBERCULAR ACTIVITY OF THE NEW DERIVATIVES ANABASINE R. T. Tlegenov, Karakalpak State University named after Berdach, 230112, Uzbekistan, Republic of the Karakalpakstan, Nukus. E-mail: [email protected]

Anabasine is main alkaloid of plants Anabasis aphylla. For anabasine having in the molecule pyridine and pipyridine of a fragment with secondary aminegroups give significant synthetic opportunities at updating structures. Derivatives of anabasine were synthesized boiling of initial components in benzine at presence catalytical of quantity of an ice acetic acid and pipyridine with constant removal of formed water as double azeotrone:

N N

Ac2O

H

RCHO

N N

O

CH3

AcOH

N N

O

R

R: Ar

The structure of the synthesized compounds is confirmed by the data IR,NMR spectra, and also data of the element analysis. The synthesized substances were investigated in vitro on antitubercular activity against М. tuberculosis R37Rv under the program TAACF, Southern Research Institute, USA. Is shown, that presence pyridine of a cycle conduct to increase of activity. The data of biological researches give the bases for continuation of search effective antibacterial of preparations among derivative alkaloid anabasine . The authors are grateful to the employees TAACF, Southern Research Institute, USA for the help at definition antitubercular of activity of the synthesized compounds.

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CROWN-ETHERS AT THE WATER-AIR INTERFACE U. B.Toyirov, U. Z. Mirkhodjaev, A. K. Tashmukhamedova, B. A. Tashmukhamedov Department of Biophysics, National University of Uzbekistan, 100174, Vuzgorodok, Tashkent, Uzbekistan. Е-mail: [email protected]

Crown-ethers, as functional analogs of membrane-active antibiotics, have complexone, channel-forming and ionophoric properties [1-3]. Here, we studied the thermodynamic state of monolayers formed by 4',4'(5')-diacetyl-dibenzo-18-crown-6 (DB18K6), which is a Ca2+-chelator, 4',4''(5'')-dibutyryl-DB18K6 and 4'4''(5'') divaleril-DB18K6, which are Ca2+-ionophores, in the presence and absence of Ca2+ ions in the underlying solution. The change of the area per one molecule of crown ether in the state of collapse has been estimated. Also, we studied the interaction of sulfoderivatives of the dibenzo-18-crown-6 (DB18K6): 4'-DB18K6-sulfonic acid, 4',4''(5'')-DB18K6-disulfonic acid (both are channel formers

K+

for

ions

in

bilayers)

with

dipalmitoylphosphatidylcholine

(DPPC).

The

phospholipid study

monolayers

was

made

of

by

the

conducted

Langmuir-Blodgett method with an accuracy of 0.05 mN/m. Structural formulas of the studied crown ethers are given below: 4'4''(5'')-diacetyl-DB18K6 (R = R1 = COCH3) R

O

O

O

O

H

O

R1

O

4'4''(5'')-dibutyryl-DB18K6

(R = R1 = COC3H7)

4'4''(5'')-divaleril-DB18K6 (R = R1 = COC4H9) 4'-DB18K6-sulfonic acid 4'4''(5'')-disulfonic DB18K6

(R = H; R1 = SO3H) (R = R1 = SO3H)

We evaluated the changes in the area attributable to a single molecule of the phospholipid monolayer in the presence of K+ ions in the sub-phase. It was found that the studied crown ethers form stable monolayers at the interface “water-air”, provoking a negative adsorption. When the concentration of Ca2+ ions in the underlying solution was equal to 10-3 M, the area per molecule of 4',4''(5'')-diacetyl-DB18K6 has changed from 0.24 nm2 to 0.05 nm2 upon compression of the monolayer to the state of collapse; likewise, for 4 '4''(5'')-dibutyryl-DB18K6

it

decreased

from 2

0.19

nm2 to 2

0.03

nm2

and

for

4',4''(5'')-divaleril-DB18K6 − from 0.17 nm to 0.045 nm , respectively. It was shown that · 184 ·

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for the most active Ca2+ ionophores, this area is reduced by more than two times compared to regular Ca2+-chelators. In the presence of K+ ions at a concentration of 2×10-5 M, the area per molecule of phospholipid changed from 1.71 nm2 down to 0.50 nm2. It turned out that for the most membrane-active 4',4''(5'')-DB18K6-disulfonic acid, the area per molecule started to change already at a concentration of 1×10-6 M and decrease from 1.8 nm2 down to 0.55 nm2. From the results obtained it was evident that for the active K+-channel-former, 4',4''(5'')-DB18K6-disulfonic, the operating threshold concentration of K+ ions was app. 20 times lower compared to the less membrane-active 4'-DB18K6-sulfonic acid. REFERENCES

1. T.

Osa,

J.

L.

Atwood.

Inclusion

aspects

of

membrane

chemistry,

Dordrecht/Boston/London: Kluwer Academic Publisher, p. 290 (1991). 2. Luis Echogoyen, E. KaiferAngel. Physical Supramolecular Chemistry, Dordrecht /Boston/ London: Published in cooperation with NATO Scientific Affairs Division, p. 466 (1996). 3. B. A. Tashmukhamedov, A. I. Gagelgans, A. K. Tashmukhamedova. U. Z. Mirкhodjaev, M. V. Zamaraeva, A. V. Shkinev, Sh. K. Norov. Synthesis, membrane active properties and biological effects of crown ethers, FAN, Tashkent, p. 264 (1987).

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ABSORPTION OF ANTI-ARRHYTHMIC ALKALOIDS IN THE CACO-2 MODEL L. K. Tsiklauria, H. Hoyerb, G. Chkhikvadzea, G. V. Tsagareishvilia, V. J. Vachnadzea, A. Bernkop-Schnurchb a

TMSU I. Kutateladze Pharmacochemistry Institute, P. Sarajishvili Str. 36, 0159 Tbilisi, Georgia b

Leopold-Franzens – University Innsbruck, Innrain 52, 6020 Innsbruck, Austria / Europe

The intestinal transport of anti-arrhythmic substance (Vingerbine) comprising by four indoline alkaloids: Vincarine (VNC), Vincamajine (VNM), Herbadine (HBD) and Herbamine (HBM) isolated from Vinca herbaceae Waldst et Kit was investigated first time using the monolayers of the human colon adenocarcinoma cell line Caco-2 as a model system for intestinal absorption. The permeability of VNC, VNM, HBD and HBM was studied from apical side (AP side) to basolateral side (BL side) or from BL side to AP side in the presence and absence of specific P-gp inhibitor. The alkaloids were measured by reversed-phase high performance liquid chromatography (HPLC) coupled with UV detector. Transport parameters and apparent permeability coefficients (Papp) were calculated. All constituent alkaloids possess similar parent skeleton structure with different substituent at secondary amino group (H, CH3) and C-2 (OH) positions. HBM and VNM exhibited time dependent permeation with Papp values in the range 10-5-10-6 cm/s. VNC and HBD exhibited significantly larger basolateral to apical P(app) than that of the reverse direction, suggesting the existence of efflux mechanisms. Verapamil pretreatment led to a significant inhibition of the efflux of VNC and HBD, whereas it had no effect on the basolateral to apical transport of HBM and VNM, suggesting that P-glycoprotein (P-gp) play a role in the intestinal efflux of VNC and HBD. These findings, together with our previous work (Pharm. Chem. J. 42(12), 693-695 (2008)) suggest that P-gp/MDR1-mediated efflux of VNC and

HBD may contribute to the low oral bioavailability of crude alkaloids with anti-arrhythmic and cardiotonic properties.

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Figure 1. Transepithelial transport of VNC (A) and HBD (B) in the absorptive (open symbols) and secretory direction (filled symbols) in the absence () or presence () of P-gp inhibitor across the Caco-2 cells. Transport data are expressed as a percentage of the total dose VNC and HBD in Vingerbine (0.02% m/v) applied to the apical or basolateral side of the cell. Each value represents the mean ± SD of at least 3 trials.

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STUDY ON THE CELL MODEL OF ANTI-VITILIGO ACTIVITY OF VERNONIA ANTHELMINTICA A. Tuerxuntayi, Maidina, Y. Q. Liu, H. A. Aisa The Key Laboratory of Chemistry of Plant Resources in Arid Regions, CAS Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, Xinjiang, China

The crude extract of the seeds of Vernonia anthelmintica Willd is a traditional Chinese medicine as vermicide, also used by Uygurs for the treatment of vitiligo for several centuries, and most recently found as an effective medicine for treating breast cancer. Our preliminary research results proven that melanin activity interesting extracts from traditional Uighur’s medicines, the chloroform extract, EtOAc extract, n-BuOH extract and EtOH extract of V. anthelmintica and enhance the activity of tyrosinase were elucidated. The tyrosinase activity was tested in the method of L-DOPA rapid oxidation. Then we select and optimiza the experimental conditions on B16 mouse melanoma cells for testing the activity of V. anthelmintica. Screening the different Kos, O., Castro Flasks, different cell concentrations, different medium, determine the tyrosinase and melanin content determination method and determine the contents of positive control (8-MOP). Finally choose the 40 μg/mL (185 μM) of 8-MOP on this condition to testing the stability of the system. The result is the added value of tyrosinase in 30%; melanocytes in 10%. The activity on B16 mouse melanoma cells of different extracts and compounds of V. anthelmintica are undergoing. Acknowledgements

This work is financially supported by National Natural Science Foundation (Grant. 20902106) and the Xinjiang Natural Science Foundation (Grant. 2009211B34).

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REFERENCES

1.

H. Yoshida, T. Kunisada, T. Grimm, et a1. Review: melanoeyte migration and survival controlled by SCF/c-kit expression. J. Invest. Dermatol Symp. Proc. 6, l-5 (200l).

2.

A. Norris, C. Todd, A. Graham, et a1. The expression of the c-kit receptor by epidermal melanocytes may be reduced in vitiligo. Br. J. Dermato1, l34, 299-306 (1996).

3.

R. Halaban. Culture of melanocytes from nornal, benign and malignant lesions, Fragner RP eds, New York: Wiley, pp. 288-3 l 8 (2004).

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STUDY ON EXTRACTION OF FLAVONOIDS FROM DRACOEPHALUM MOLOLARIE L. AND ITS ANTIOXIDANT ACTIVITY Y. Turahun, T. Muhammad College of Chemistry and Engineering, Xinjiang University, Urumqi, Xinjiang, 830046

Study on the extraction process of total flavonoids from Dracoephalum mololarie L. by ultrasonic method and its antioxidant activity. The orthogonal experimental method was designed on single factor experimental results, the scavenging effect of the extract against free radicals and reducing power was also studied by spectrophotometer. The optimum conditions: ethanol concentration 60%, ultrasonic treatment time 50 min, extraction temperature 50 ºC and solid -liquid ratio 1:40 (g/mL). Under these optimum conditions, the extraction efficiency of total flavonoids is 1.89%. Total flavonoids from Dracoephalum mololarie L. reducing power was 1 time larger than VC, the half-inhibitory concentration

(IC50) of hydroxyl radicals, DPPH and superoxide anion were 35.6, 31.1, and 56.0 μg/mL. Total flavonoids from Dracoephalum mololarie L. has strong antioxidant activity, and there exist obvious concentration-response relations.

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ANALYSIS OF VOLATILE COMPOUNDS IN DRACOCEPHALUM HETEROPHYLLUM GROWING IN XINJIANG BY USING HS-SPME-GC-MS TECHNIQUE M. Tuxuna,d , Q. Wang a,b , H. J. Han b , L. Liua , H. A. Aisaa a

Xinjiang Key Laboratory of Plant Resources and Natural Products Chemistry, Xinjiang

Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China b

The Provincial Institute for Food and Drug Control of Xinjiang, Urumqi 830001, China c

Graduate School of the Chinese Academy of Sciences, Beijing 100039, China

d

Postgraduate college of Xinjiang Medical University, Urumqi 830054, China Tel.: +86 991 3835679; fax: +86 991 3838957 E-mail: [email protected]

In this study, a head space solid-phase micro extraction (HD-SPME) method coupling with gas chromatography and gas chromatography mass spectrometry was introduced to determine the volatile organic compounds (VOCs) in the Dracocephalum heterophyllum (D. heterophyllum) in Xinjiang. Four types of solid phase micro extraction fiber coatings were

investigated including polydimethylsiloxane (PDMS), polydimethylsiloxanedivinylbenzene (PDMS/DVB), divinylbenzene carboxen polydimethylsiloxane (DVB/CAR/PDMS) and carboxenpolydimethylsiloxane (CAR/DVB). The optimized conditions were: using DVB/CAR/PDMS fiber coating, 50 oC absorption temperature and 45 min equalization time. In the optimized parameters, 38 compounds were analyzed, and the major components of D. heterophyllum were α-Citral (29.23%), β-Citra (17.29%), Sabinene hydrate (10.88%),

Isopinocamphone (3.95%), β-Citronellol (2.90%) and Cineole (2.37%). HD-SPME has been proven to be an adequate technique to determine the VOCs of D. heterophyllum.

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BIOLOGICALLY AND PHARMACOLOGICALLY ACTIVE ALKALOIDS FROM THE FLORA OF GEORGIA V. U.Vachnadzea, L. G. Kintsurahvilia, N. D. Gaguaa, T. Sh. Suladzea, N. S. Vachnadzea, I. S. Sikharulidzea, N. M. Gogitidzea, A. Dz. Bakuridzeb a

Tbilisi State Medical University I. Kutateladze Institute of Pharmacochemistry, 36 P. Saradjishvili Str., 0159, Tbilisi, Georgia

b

Tbilisi State Medical University, Department of Pharmaceutical Technology, 33 Vaja Pshavela, 0177, Tbilisi, Georgia

The phyto investigation of Georgian flora evidenced 400 species of alkaloid containing plants. According to productivity and composition of biologically active compounds, the following families need to be highlighted: Amaryllidaceae, Buxsaceae, Fabaceae, Liliaceae, Ranunculaceae, Taxaceae, Zugophyllaceae. Perspective drugs based on indolic, izochinolin, taxol alkaloids are developed and proposed with antiarythimic, anticancer activity and as stimulator of leucopoiesis and brain circulation furthermore. According to pharmacological investigations some of steroid and oxindole alkaloids increases the growth of cancer cells and increase the proliferation of fibrocites in cell culture. Chinazoline and buxan alkaloids have shown antihistamine and anticholenestherase activity. Original phytotechnologies for receipt of drugs are developed based on extraction with diluent gaz from raw material of plant origin and fractioning by microfiltration on membrane equipment.

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CHEMICAL COMPOSITION AND ANTIOXIDANT ACTIVITY OF THE ESSENTIAL OILS AND VARIOUS SOLVENT EXTRACTS FROM WILD AND CULTIVATED CARROT (DAUCUS CARROT L.) SEEDS OF XINJIANG IN CHINA Q. Wanga,b, L. Liu a, H. A. Aisaa a

Xinjiang Key Laboratory of Plant Resources and Natural Products Chemistry, Xinjiang

Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China Tel.: +86 991 3835679; Fax: +86 991 3838957. E-mail: [email protected] b

Graduate School of the Chinese Academy of Sciences, Beijing 100039, China

The essential oils of the wild and cultivated carrot (Daucus carrot L.) seeds (Apiaceae) from Xinjiang was isolated by hydrodistillation in yields of 3.89% (v/w) and 2.13% (v/w), respectively. The chemical composition of the essential oils were analysed by GC(Gas Chromatography ) and GC/MS (Gas chromatography/mass spectrometry). The major components from Carrot seed in the wild were carotol (78.61%), β-bisabolene (3.92%) and α-bergamotene (2.93%). Cultivated plants contained carotol (79.22%), β-bisabolene (4.26%)

and γ-cadinene (2.18%) as the major components. Wild and cultivated carrot (Daucus carrot L.) seed extracts (methanol, ethyl acetate, dichloromethane, hexane) contained total phenolic contents (5.81, 4.79, 3.26, 2.68, 8.11, 4.32, 3.39, 2.38, GAE (gallic acid), μg/mg) and total flavonoid contents (11.13, 8.78, 6.50, 4.94, 19.41, 12.56, 2.86, 2.50, RE (rutin), μg/mg), respectively. Antioxidant activities of the essential oils and extracts were evaluated using three different assays, DPPH, ABTS and reducing power assays. In DPPH system, the highest radical-scavenging activity was seen by the polar solvent of methanol extract. Furthermore, in the ABTS and reducing power assays, the antioxidant capacity of the polar subfraction found to be the stronger one. In systems, antioxidant capacities of butylated hydroxytoluene and L-ascorbic acid were determined in parallel experiment.

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ANTI TUMOR EFFECTS OF SQUAMOCIN-LOADED ELECTROSPUN FIBERS X. W. Wang a, b, D. Zhang a, b ,Y. H. Liao c, J. Wang d, X. L..Deng e, X. PYangd, J. T. Tanga, b a

Institute of neurological disorders, Yuquan hospital, Tsinghua university, Beijing, 100049, China b Key Laboratory of Particle & Radiation Imaging (Tsinghua University), Ministry of Education, Beijing, 100084, China c Institute of Medicinal Plant Development, Chinese Academy of Medical Science & Peking Union Medical College, Beijing 100094,China d The key laboratory of Beijing City on preparation and Processing of novel Polymer, Beijing University of Chemical Technology, Beijing 100029 e Peking University School and Hospital of Stomatology, Beijing 100081

Squamocin is a cytotoxic bis-tetrahydrofuran containing acetogenin that was isolated from Annona squamosa two decades ago. Squamocin has been reported to have antiproliferation effects on many kinds of cancers including leukemia, liver cancer, breast adenocarcinoma, and bladder cancer. Coaxial eletrospining technique was developed for simultaneously electrospinning two different polymer solutions into core-shell structured drug-loading nanofibers. To investigate the capability of eletrospun-nanofiber delivery system to control the release of antitumor traditional Chinese medicine, squamocin was encapsulated in the eletropun fibers. Nanofibers composed of PLGA as shell and PVP containing squamocin as core were prepared. The morphology of the electrospun fibers was examined using scanning electron microscope (SEM) and transmission electron microscope (TEM). The drug release from the fibers and cytotoxicity of squamocin-loaded fiber were studied. The squamocin-loaded fiber was core-shell structure and the IR spectrum showed two strong bands around 1740 cm-1 and 1300cm-1, characteristic of the -C=O and -C-O-C-vibrations related to squamocin. The fiber loaded with squamocin presented linear release rather than burst release. Squamocin inhibited proliferation of oral cancer cell lines Tca8113 and KB cells with IC 50 values of 4.4mg/mL and 0.45mg/mL respectively. Ninety eight percent of KB cells were inhibited after being cultured in the medium containing squamocin-loaded fibers for 48h. The results of our investigation have demonstrated that electrospun fibers loaded with squamocin were successfully obtained using coaxial eletrospining technique. · 194 ·

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PROTEIN-IMPRINTED POLYMERS GRAFTED TO FLOW THROUGH POLY (TRIMETHYLOLPROPANE TRIMETHACRYLATE) MONOLITHS X. H. Wang Y. P. Huang Z. S. Liu* H. A. Aisa Key Laboratory of Plant Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, 40-1 South Beijing Road, Urumqi 830011, Xinjiang, China, E-mail: [email protected]

In this paper, a MIP coating grafted to a trimethylolpropane trimethacrylate (TRIM) core material for bovine serum albumin (BSA) was reported. The core monolith was prepared using a solution of 40% (w/w) TRIM with a mixture of porogen, toluene and isooctane. Graft polymerization took place on the resultant TRIM monolith with BSA as template, acrylamide as functional monomer, N', N-dimethylacrylamide as cross-linking agent and ammonium persulfate as initiator. Stronger retention of template protein on the grafted MIP monolith. The influence of the chromatographic conditions on molecular recognition, including the composition of the mobile phase, pH value and salt concentration was also studied. These results suggest that this grafted polymerization technique of allows the imprints to be directly created on the surface of the monolithic material using a minimum amount of protein. Acknowledgements

This work was supported by the National Natural Science Foundation of China (Grant No. 21075090). REFERENCES

1.

J. Courtois, G. Fischer, O. Sellergren, K. Irgum. J. Chromatogr. A, 1109, 92-99 (2006).

2.

L. Qin, X. W. He, M. Jia, W. Y. Li, Y. K. Zhang. Chem. Eur. J. 17, 696-704 (2011).

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STUDY ON POLYSACCHARIDES FROM UYGUR MEDICINE DIAPHRAGMA JUGLANDIS FRUCTUS BY PHENOL-SULFURIC ACID METHOD Y. Wanga, R. Kasimb, Azigulia, A. Simayila,* a b

Pharmacy College, Xinjiang Medical University, Urumqi 830011, China;

Urumqi Hospital of Traditional Chinese Medicine, Urumqi 830000, China

Objective To study Polysaccharides from Uygur Medicine diaphragma juglandis fructus

by phenol-sulfuric acid. Method 1. To select the refined polysaccharides of diaphragma juglandis fructus as a

research object, optimizing the chromomeric condition of phenol-sulfuric acid method by performing single factor experiment. 2. With the optimized phenol-sulfuric acid methods, the content of polysaccharides from diaphragma juglandis fructus was assayed. Results The linear relationship of polysaccharides’ concentration was at the range of 5.0

~ 17.5 μg/mL. And the average recover was 108.3880%, RSD was 7.3161%. The contents of polysaccharides in diaphragma juglandis fructus was 5.40%, assaying with optimized phenol-sulfuric acid method. Conclusion The assay method which acquired reliable results was proved to be simple,

convenient, accurate and stable; and can be used for the quality control of Uygur Medicine diaphragma juglandis fructus.

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SYNTHESIS OF 2-METHYLENE-OLEANONIC ACID AS A POTENTIAL ANTITUMOR AGENT H. K. Wu, G. Li, H. H. Li, Y. W. Yuan, Z. Su College of Chemistry and Chemical Engineering, Anyang Normal University, Anyang 455002, China, Tel: +86 151 372 38927. E-mail: [email protected]

Oleanolic acid is a naturally occurring triterpenoid, widely distributed in food and medicinal plants, such as Ligustrum lucidum Ait, et al. It is relatively non-toxic, antitumor, and hepatoprotective, as well as exhibiting antiviral properties, and it was found to exhibit strong anti-HIV activity[1]. , -Unsaturated carbonyl function occurs in a wide variety of bioactive natural products. It is usually associated with the bioactivities of these compounds and acts as Michael acceptors for the addition of protein nucleophilic groups. The design and synthesis of new compounds containing this functionality has provided a wide range of compounds, which can serve as building blocks of high synthetic versatility[2]. Herein, we have syntheszied a derivative named 2-methylene-oleanonic acid. The starting compound oleonolic acid was first oxidazed by Jones reagent to produce oleononic acid, and followed by -methylenenation with paraformaldehyde, mopholine, and catalysed by molecular sieves in galacial acetic acid[3]. The futher antitumor activity study of this compound is in progress.

REFERENCES

1.

J. Liu. J. Ethnopharmacol. 49, 57-68 (1995).

2.

Nuno M Xavier, Amélia P Rauter. Carbohydr. Res. 343,1523-1539 (2008).

3.

D. F. Cintia, Milagre, et al. J. Mass. Spectrom. 42, 1287-1293 (2007).

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PROBING THE MECHANISM OF DIRECT MANNICH-TYPE -METHYLENATION OF OLEANONIC ACID VIA UPLC-ESI-TOF-MS H. K. Wu, J. S. Zhang, D. H. Deng, Z. Su, H. H. Li College of Chemistry and Chemical Engineering, Anyang Normal University, Anyang 455002, China, Tel: +86 151 372 38927. E-mail: [email protected]

In the process of preparing 2-methylene oleanonic acid from oleanolic acid. Jones reagent was used and followed by -methylenation. The possible mechanism of the reaction were probed via Waters Acquity UPLC Premier XE (a high resolution UPLC-ESI-TOF-MS). The direct methylenation underwent a Mannich-type reaction, and the intermediate was detected by MS with m/z 554.4202. The mechanism was showed here.

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ANTI-INFLAMMATORY ACTIVITY,ANALGESIC ACTIVITY AND CHEMICAL CONSTITUENTS OF LACTUCA SATIVA L. SEEDS F. Xu.a,b,c, H. A. Aisaa a

State Key Laboratory Basis of Xinjiang indigenous medicinal plants resource utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China; b

Graduate University of Chinese Academy of Sciences, Beijing 100039, China; c

Xinjiang Institute of Materia Medica, Urumqi 830004, China

The extractions were obtained from Lactuca sativa L. seeds with 95% ethyl alcohol, 50% ethyl alcohol and water, respectively. Anti-inflammatory activity of the extractions were evaluated by mouse ear edema which induced by xylene. And analgesic activity of the extractions was evaluated by mouse writhing symptom caused by acetic acid. The three extracts can inhibit the ear edema and reduce writhing times. The extraction from Lactuca sativa L. seeds with 50% ethyl alcohol is best in anti-inflammatory activity among the three

extracts. The extract with 95% ethyl alcohol is best in analgesic activity among the three extracts. Chemical constituents were isolated from Lactuca sativa L. seeds via extraction with ethyl alcohol, purified by various column chromatographies, and identified on the basis of physical and spectral data. Four compounds were isolated, and three compounds were identified as caffeic acid (1), quercetin (2) and isoquercitrin (3). Compounds 1~3 were isolated from Lactuca sativa L. seeds for the first time. Acknowledgements

This work was supported by China National Funds for Distinguished Young Scientists No. 30925045. Research was also supported by the CAS/SAFEA International Partnership Program for Creative Research Teams.

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MOLECULAR COMPLEXATION OF IVY AND LICORICE SAPONINS L. A. Yakovishina, V. I. Grishkovetsb, D. Yu. Belasha, I. R. Yarovoya, E. N. Korzha a

Sevastopol National Technical University, Sevastopol, Ukraine, Е-mail: [email protected]

b

V. I. Vernadsky Taurida National University, Simferopol, Ukraine

Today the complexation of triterpene saponins with biologically active compounds is of great interest because it represents a method for creating low-dose drugs. We examined some of the most common triterpene glycosides of genus Hedera L. as promising complexants. These

included

the

-hederin

glycosides

3-О--L-rhamnopyranosyl-(12)-О--L-arabinopyranoside)

(hederagenin

and

hederasaponin

C

(hederagenin 3-О--L-rhamnopyranosyl-(12)-О--L-arabinopyranosyl-28-О--Lrhamnopyranosyl-(14)-О--D-glucopyranosyl-(16)-О--D-glucopyranoside). We prepared molecular complexes of -hederin, hederasaponin C, and monoammonium glycyrrhizate (glycyrram) among themselves. -Glycyrrhizic acid is the principal triterpene glycoside of licorice roots. The composition of the complexes was determined by method of isomolar series. IR and UV spectroscopy confirmed that intermolecular interactions exist between saponins. HOOC30

29

30

20 20

12

O 12

18 11

NH4

18

H

28

28

COOR

H

16 9

1

OH

COO

O

HO

23

O

OH

COO

-Hederin: R=?

HO

hederasaponin C: R=

O O

O

HO

7

OH

HO

H3C HO

3

9

O O

3

O

1

Glcp-(6

1)-Glcp-(4

1)-Rhap

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"VER-MOL-2" ZINC CONTAINING NATURAL BIOLOGICALLY ACTIVE SUBSTANCES F. T. Yakubova, O. Kh. aitmuratova, N. J. Sagdiev Institute of Bioorganic Chemistry Acad. AS Sadykov, Uzbekistan Academy of Tashkent Pediatric Medical Institute

In the average human body contains about 2.2 g of zinc which is concentrated primarily in the kidneys, liver, muscle, skin and hair in the prostate gland of men. In recent years, scholarly attention is directed at clarifying the role of zinc in diabetes mellitus (A. P. Avtsyn and others, 1991). Zinc deficiency conditions is an important issue for practical medicine. Zinc activates over 200 enzymes in the body and is one of the well-known immunomodulators. Zinc is essential for the synthesis and secretion of insulin and digestive enzymes of the pancreas. Zinc containing plants stimulate the synthesis of insulin and stimulate the work and the immune system. Consequently, zinc deficiency conditions affect a wide range of biological activity of zinc, which is of great importance, both in prenatal and postnatal development of the organism. The purpose of this study is determination the zinc content of the "Ver-Mol-2" and its further recommendations as a dietary supplement. "Ver-Mol-2" was isolated from the animals, made on the basis of camel shubat. Previously, we studied general and monosaccharide composition "Ver-Mol-2" Content and composition of trace elements was determined by neutron activation analysis at the Institute of Nuclear Physics of Uzbekistan Academy of Sciences. The study showed that in the "Ver-Mol-2" has a large amount of Zn compared with cow and goat milk. The data obtained allow concluding that, after complete pharmacological studies, "Ver-Mol-2", as a source of Zn, may be recommended as a dietary supplement for the treatment of zinc deficiency conditions, especially in mild diabetes.

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SEPARATION OF DEHYDROVOMIFOLIOL FROM LEAVES OF NITRARIA SIBIRICA BY HIGH-SPEED COUNTER-CURRENT CHROMATOGRAPHY Y. Yanga, M. Bakria,b, D. Y. Gua,b, H. A. Aisaa a

Key Laboratory of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang

Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China, E-mail: [email protected], Tel: +86 991 3835679. b

Graduate School of Chinese Academy of Sciences, Beijing 100039, China

An effective high-speed countercurrent chromatography (HSCCC) method was established for separation and purification of dehydrovomifoliol from the leaves of Nitraria Sibirica. HSCCC was performed with three two-phase solvent systems composed of n-hexane-ethyl acetate-methanol-water (2 : 5 : 2 : 5, v/v). 11 mg dehydrovomifoliol (HPLC

purity 96.18%) was isolated from 200 mg the crude sample of Nitraria sibirica. The chemical structure was confirmed by MS, 1H NMR and 13C NMR. Acknowledgements

This work was funded by the China National Founds for Distinguished Young Scientists (Grant No. 30925045). Research was also supported by the CAS/SAFEA International Partnership Program for Creative Research Teams and West Light Foundation of The Chinese Academy of Sciences.

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STUDY ON THE IDENTIFICATION OF CICHORIUM GLANDULOSUM BOISS.ET HUET. AND CICHORIUM INTYBUS L.BY MULTI-STEPS INFRARED MACRO-F INGERPRINT METHOD W. J. Yanga,b,d, Zaynapb, Marhabab, S. Q. Sunc, H. A. Aisaa a

Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences Urumqi 830011 China b c d

Xinjiang Institute of Materia Medica, Urumqi 830002 China

Department of Chemistry , Tsinghua University , Beijing 100084 China

Graduate University of Chinese Academy of Sciences, Beijing 100084 China

Cichorium glandulosum Boiss. et Hout which belongs to the family compositae and the

genus Cichorium L. is habitually used by the Uyghur nationality. It has the functions of clearing liver-heat, cholagogue, stomachic, digestive, diuretic and detumescent. Therefore it is used for the treatment of dampness-heat, jaundice, stomachache, anorexia, oedema and oliguria diseases. According to the Chinese Pharmacopeia (2010 edition, Part I), the drug Herba Cichorii come from the aerial parts of Cichorium glandulosum Boiss. et Hout (Compositae) and Cichorium intybus L. (Compositae). In order to clarify the bioactive basis of the medicinal plant, three kinds of infrared spectroscopy identification methods were used to distinguish Cichorium Glandulosum Boiss.et Huet and Cichorium intybus. L. Infrared spectra show that the content of sugar and aromatic component is higher in the Cichorium Glandulosum Boiss.et Huet than it in Cichorium intybus L. Observing their secondary

derivative spectra , in the range of 1800-1300 cm-1, the strongest peak of Cichorium Glandulosum Boiss.et Huet which is from the aromatic compounds is at 1593 cm-1, and it of Cichorium intybus L which is from the protein amide I band is at 1660 cm-1, the intensity of

peaks at 1593, 1509, 1421, 1377 and 1336 cm-1 of Cichorium Glandulosum Boiss.et Huet is more difference from Cichorium intybus L. In 1200-700 cm-1, they have similar peaks at the 717 and 713 cm-1, in addition, the strongest peak of Cichorium Glandulosum Boiss.et Huet. at 1063 and 957 cm-1 which is more difference from Cichorium intybus L. The distinction of 2D IR correlation spectra is more obviously. In 1800-1500 cm-1, the stronger automatic peaks of Cichorium Glandulosum Boiss.et Huet. is at 1590 and 1660 cm-1, respectively, but · 203 ·

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those of Cichorium intybus L. have a very wide area auto peak in the 1700-1500 cm-1, respectively. In 1120-880 cm-1, Cichorium Glandulosum Boiss.et Huet has three automatic peaks while Cichorium intybus L has two. All of these results show that the infrared spectra of three identification method is a simple, fast method, and can be used as a identification basis for Cichorium Glandulosum Boiss.et Huet. and Cichorium intybus L. Acknowledgements

This work was supported by China National Funds for Distinguished Young Scientists No. 30925045, by the modernization of Minority Medicine in Xinjiang (200733146-4).

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CHEMICAL CONSTITUENTS OF ZIZIPHORA CLINOPODIOIDES Y. H. Yea,b, Bahanga, Y. Q. Liua, G. A. Zoua, H. A. Aisaa a

Key Laboratory of Plant Resources and Chemistry in Arid Regions, Xinjiang Technical Institute of Physics and Chemistry, CAS, Urumqi 830011, China; Tel: +86-991-3835679, E-mail: [email protected] b Graduate School of the Chinese Academy of Sciences, Beijing 100039, P. R. China Ziziphora clinopodioides Lam. (Labiatae), mainly distributed in Xinjiang of China, Central Asia and Mongolia[1], is widely used as an Uyghur folk medicine for the treatment of hypertension, coronary artery disease and other cardiovascular diseases[2]. It was reported that total flavonoids of Z. clinopodioides showed significantly anti-myocardial ischemic activity and the volatile oil possessed good anti-bacterial and anti-oxidant activities[3]. In our research of chemical constituents from Z. clinopodioides, four compounds were isolated and their structures were identified as picein (I), daucosterol (Ⅱ), apigenin (Ⅲ), and 5,7,2′-trihydroxyflavone 2′-O-β-D-glucopyranoside (Ⅳ). Compounds I and Ⅳ were firstly isolated from the genus Ziziphora. ACKNOWLEDGEMENT: This work was supported by China National Science Fund for Distinguished Young Scholars (No. 30925045) and the CAS/SAFEA International Partnership Program for Creative Research Teams (2008-18). REFERENCES

1.

2.

3.

N. Li; X. J. Yang; D. L. Meng; X. Li. Isolation and identification of chemical constituents from stem and root of Ziziphora clinopodioides Lam. Journal of Shenyang Pharmaceutical University 26(9), 691-693 (2009). M. Tabotabaei-Anaraki; F. Chalabian; S. Masoudi; A. Rustaiyan. The chemical composition and in vitro antibacterial activities of the oil of Ziziphora clinopodioides Lam. from Iran. Planta Medica 73(9), 852-853 (2007). S. G. Tian; Y. Shi; X. Y. Zhou; L. Ge; H. Upur. Total polyphenolic (flavonoids) content and antioxidant capacity of different Ziziphora clinopodioides Lam. Extracts. Pharmacognosy Magazine 7(25), 65-68 (2011). · 205 ·

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COMPARATIVE ANALYSIS OF BIOLOGICALLY ACTIVE COMPOUNDS OF GENUS CLIMACOPTERA B. K. Yeskaliyevaa, G. A. Seitimovaa, A. T. Kaliyeva, G. Sh. Burashevaa, Zh. A. Abilova, H. A. Aisab a

Al-Farabi Kazakh National University, Chemistry department, Almaty, Kazakhstan, Е-mail: [email protected] b

Xinjiang Technical Institute of Physics and Chemistry, CAS, Urumqi, China

In recent years, expanding the study of wild plants, widely grown in saline and arid soils of the Republic of Kazakhstan and adapted to extreme conditions. These include the plant of the genus Climacoptera, family Chenopodiaceae is widely grown in the territory of Kazakhstan. Plants of the genus Climacoptera comprise 23 species, in Kazakhstan found 14 species. The objects of study are the aerial parts of C. branchiata, C. ferganica harvested in the flowering stage in 2010, from western Kazakhstan, and C. obtusifolia - from Tajikistan. In order to obtain biologically active compounds of the genus Climacoptera, crushed air-dry raw material subjected to extraction by 70% methanol. The combined extract was concentrated and successively extracted with petroleum ether-, chloroform, ethyl acetate and n-butanol. The methods of two-dimensional paper chromatography and TLC in different solvent systems revealed that the major groups of biologically active substances of plant above-ground mass are investigated saponins, tannins, flavonoids, amino acids, mono-, oligo-and polysaccharides, phenolic acids. Petroleum ether extract three species of the genus Climacoptera are put on the analysis of volatile compounds in GC-MS. As a result, defined Climacoptera obtusifolia contains 26 substances, Climacoptera brachiata - 25 substances, Climacoptera ferganica - 29 substances. For the separation of compounds ethyl acetate used silica gel adsorbent and eluent chloroform with increasing methanol. From collected fractions were separated quercetin, rutin and hyperin. The butanol-soluble extract was detected flavonoids and saponins. A study in this work continues. · 206 ·

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LIPOPHILIC COMPOSITION OF SEEDS OF SAFFLOWER “AK MAI”, GROWING IN KAZAKHSTAN B. K. Yeskaliyeva а, A. A. Turgumbayeva а,b, G. Sh. Burasheva а, M. Konirbekov b, A. M. Onzhigitov b, H. A. Aisac a

Al-Farabi Kazakh National University, Kazakhstan, Almaty, Е-mail: [email protected] b

Limited Liability Company «Adal-Agro», Kazakhstan, Almaty, Е-mail: [email protected]

c

Xinjiang Technical Institute of Physics and Chemistry, CAS, Urumqi, China

The relevancy of current research is related to the needs of pharmaceutical and food industry of Kazakhstan in new and effective phytogenous substances. In this regard, the study of local flora and breeding a new variety of safflower named "Akmai" as a source of potential medicinal and food resources meet the needs of domestic medicine and food industry. A literature analysis showed that the chemical composition of the aboveground part of the plant of "Akmai" safflower, cultivated in southern Kazakhstan had not been explored. Safflower (Carthamus tinctorius L.), a member of Asteraceae family, is one of the important aromatic and medicinal plants. The plant is 100 cm tall, with globular flower heads and commonly, brilliant yellow, orange or red flowers. Traditionally safflower was grown for their flowers, which were used as a fabric dye, for food coloring and flavoring, and for medicinal purposes. Safflower oil contains about 75% linoleic acid, which is significantly higher than its content in corn, soybeans, cotton, peanut or olive oil. The object of this study is the seeds of Kazakhstan species of “Akmai” safflower, collected in the flowering stage in Southern Kazakhstan. СО2 extraction was carried out to study the component composition of Kazakhstan “Akmai” safflower seeds. Conclusions: 1. Pale yellow oily extracts were obtained by varying the process

parameters. The mass spectrum of the oily extract showed the peak at which it was confirmed that the linoleic acid content reached 91%.

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2. Biologically active complex of seeds of Kazakhstan safflower species "Ak-Mai" was release for the first time by using subcritical CO2 – extraction. 3. CO2-extracts from the seeds of Kazakhstan safflower species "Ak-Mai" were investigated by GC/MS which allowed detecting fatty acids and esters. 4. Acidity, moisture, volatiles, iodine number, unsaponifiable matter and the flash point of the extraction oil were investigated for the first time.

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EXTRACTION, PURIFICATION AND CHARACTERIZATION OF THE WATER-SOLUBLE POLYSACCHARIDES FROM SEED OF OCIMUM BASILICUM H. Yimamub,c, S. ghulamidina, A. Yilia, H. A. Aisaa, R. Kasimuc a

Xinjiang TechnicaI Institute of Physics and Chemistry, Chinese Academy of Sciences, 830011; b c

Pharmaceutical college of Xinjiang Medical University, 830054;

Graduate School of the Chinese, Academy of Sciences, Beijing, 100049

The seeds of Ocimum basilicum (300 g) were extracted with 6.0 L distilled water at 90 ºC for 2 h and filtered through four sheets of gauze. The solid material was extracted twice again under the same condition. The filtrates were combined, centrifuged to remove water–insoluble materials, concentrated to 200 mL and precipitated by the addition of 95% ethanol (4 volumes). After then, the precipitate was dried by solvent exchange. first using 95% ethanol, then absolute ethanol and finally ether. Three identical extractions were carried out and the crude polysaccharide was obtained (8.4 g). The crude polysaccharide 8.0 g was re-dissolved in distilled water (200 mL) and treated with Sevag reagent (1:4 n-butanol:chloroform, v/v, 200 mL) to remove proteins (Sevag, Lackman, Smolens. 1938).

After precipitation by ethanol and drying by solvent exchange, the deproteined polysaccharide fraction WCP (7.0 g) was obtained. After deproteination using the Sevag method a crude polysaccharide fraction, referred to as WCP (for water soluble Cicer polysaccharides), was obtained with a yield of 8.4%

(w/w). WCP contained 82.2% total

sugar, 10% uronic acid and less than 1.5% proten. Our researches offers more further information to exploit nutraceuticals and functional food of Ocimum basilicum seeds and promote sustainable development on industry of Ocimum basilicum.

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PROTECTION OF UIGUR MEDICINE CICHORIUM GLANDULOSUM EXTRACT ON TYPEⅡ DIABETES RATS Y. Zhang a,b, X. L. Xin a, H. Q. Zhao a, H. A. Aisa a a

Key Laboratory of Plant Resources and Chemistry in Arid Regions, Xinjiang Technical

Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, P. R. China, e-mail: [email protected] b

Graduate School of the Chinese Academy of Sciences, Beijing 100039, P. R. China

Cichorium glandulosum Boiss et Hout is a kind of Uighur traditional medicine. Except

for the liver protection, some other roles were reported recently such as hypoglycemic effect, protection on kidney, and its resistance to type 2 diabetes. The aim of the present study was to reveal the possible activity of Cichorium glandulosum extract (CGE) on type 2 diabetes rats. The experiment was finished on a type 2 diabetes rats’ model, which was induced by feeding high fat diet to rats and injecting a single dose of STZ (45 mg/kg). 6 kinds of indicators (ET-Ⅰ, Ang-Ⅱ, TXB-2, 6-keto-PGF1α, blood glucose and insulin level) which related to diabetes or it’s complications were chosen to observe the effect of it. The result showed that the blood glucose level of the diabetes rats (P<0.01) could be reduced by low dosage CGE (100 mg/kg), and ET-1 and Ang-2 level were decreased significantly in the two CGE groups (100 mg/kg and 300 mg/kg) compared with the Model group (P < 0.01). In addition, 6-keto-PGF1α (P < 0.01) can be increased by the two CGE groups, while TXB-2 level (P < 0.01) only can be decreased by low dosage CGE group. However, two CGE groups have no effect on type 2 diabetes rats’ insulin level either. So Uighur medicine Cichorium glandulosum extract has some effect on type 2 diabetes rats’ blood vessel

protection and blood glucose reduction, and is benefit to cardiovascular. Based on what is concerned here, it is likely to be a potential treatment drug to diabetes or its complications. Acknowledgements: This work was supported by China National Funds for

Distinguished Young Scientists No. 30925045 and the modernization of Minority Medicine in Xinjiang (200733146-4). · 210 ·

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STUDYING ON ULTRASONIC-MICROWAVE SYNERGISTIC EXTRACTION FLAVONOIDS OF KUNLUN CHRYSANTHEMUM Y. L. Zhang, A. Simayil*, Y. Wang Pharmacy College, Xinjiang Medical University, Urumqi 830011, China Objective The extraction and content determination of flavonoids of Kunlun

Chrysanthemum were studied. Ultrasonic-mi-crowave synergistic extraction technique applied in flavonoids of Kunlun Chrysanthemum were obtained. Method With rutin as the standard substance total flavonoids in Kunlun

Chrysanthemum determined by Ultraviolet spectrophotometry. Results The linear relationship of Kunlun Chrysanthemum concentration was A =

0.01109C+0.01012 (r = 0.9997), recover was 108.69%, RSD was 2.82% (n = 6). The contents of Total Flavonoids in Kunlun Chrysanthemum was 14.25%. Conclusion The assay method was proved to be simple, convenient, accurate with good

reproducibility and can be used for the determination of Kunlun Chrysanthemum.

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ALKALOIDS OF ECHINOPS NANUS BUNGE G.T.Zharylgasina1, E.E.Shults2, A.Z.Turmukhambetov1, S.M.Adekenov1 1

JSC «International research and production holding «Phytochemistry», 100009, Republic of Kazakhstan, Karaganda, [email protected] 2

Novosibirsky institute of organic chemistry of SB RAS

630090, Russia, Novosibirsk, [email protected] Echinops nanus Bunge is plant, growing in steppe areas of Central Asia and the Western

China. Plants of this genus are widely used in phytotherapy in many countries. It is caused by rich composition of biologically active substances [1]. We have carried extraction of raw material with 80% ethanol for the purpose of study of alkaloid composition of Echinops nanus Bunge roots. The received dense extract has been processed by ammonia. It has been extracted by chloroform. It has been chromatographed on aluminum oxide. Two substances have been isolated with m.p. 150-152 ºС and 180-183 °С during the elution of column by the mixture of benzene : ethanol with gradient increase in polarity. The isolated compounds have been identified as alkaloids - echinopsine and echinopsidine accordingly on the basis of the physicochemical constants and data of IR-, UV-, NMR – spectra [2]. The yield of substances has made 0.08 % and 0.02 % from mass of the air-dried raw material. Alkaloids of echinopsine and echinopsidine have been isolated from Echinops nanus Bunge for the first time. REFERENCES

1. B. M. Abegaz, Phytochemistry. (3) 879-881(1991). 2. Prabir K. Chaudhuri., Phytochemistry. (26) 587-589 (1987).

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THE QUICK-MAKING METHOD OF ROSE PIGMENT B. Zhaoa,b, A. Yilia,b, H. A. Aisaa,b a

Key Laboratory of Plants Resources and Chemistry of Arid Zone, Xinjiang Technical

Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing South Road 40-1,Urumqi 830011, Xinjiang, P. R. China b

Graduate School of the Chinese Academy of Sciences, Beijing 100039

The waste liquid, which was reused from the rose refined oil of Xinjiang's Hotan, was adjusted to pH 2-3 by 0.5mol·L-1 HCl, filtered and concentrated after standing 2 hours. The crude extract liquid was a good source of the rose pigment. Resin AB-8 have a good separation performance and was selected to purify the rose pigment. The optimum parameters were established as following 3.5 BV sample extract flow through the column at the rate of 2 BV·h-1, 4 hours later. The column was washed with water and 70% ethanol, respectively. The 70% ethanol elutes were concentrated to yield purified rose pigment. The rose pigment which was prepared from crude extract adopted the method of spray drying. The optimal spray drying condition were:110 ºC inlet air temperature, 68 ºC outlet air temperature, 0.27 mL·min-1 flux rate, 16×103 kPa pressure, and 0.5~0.8 mL·min-1 feeding speed. Then rose pigment was obtained. This method not only achieves an effective resource recycling and reusing, but also reduces pollution of waste emissions. Thus, the companies can get more benefits and the environment was protected. The preparation method is fast, convenient, economical, non-toxic, and can be used to industrial production for resources recycle.

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SYNTHESIS AND ANTI-INFLUENZA ACTIVITY OF RUPESTONIC ACID DERIVATIVES J. Y. Zhaoa,b, Y. W. Hea,b, H. A. Aisaa a

Key Laboratory of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang

Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, China,e-mail: [email protected] b

Graduate School of Chinese Academy of Sciences, Beijing 100039, China

Artemisia rupestris L., a Traditional Chinese Medicine, had a long history as a folk

medicine in Xinjiang of China. Rupestonic acid (compound 1) is a sesquiterpene with multifunctional groups, isolated from the Artemisia rupestris L. To improve biological activity of rupestonic acid, a novel series of rupestonic acid derivatives were designed and synthesized using rupestonic acid and 1, ω-dibromalkane as the starting materials. They were evaluated for the activity in vitro against influenza viruses A (H3N2, H1N1) and B. The results showed that compounds 3e and 3f possessed better activity against influenza virus A (H3N2), and compounds 3f and 4g had higher inhibition against influenza virus A (H1N1). The synthetic pathways of compounds 2a~2g, 3a~3g and 4a~4g were outlined in Scheme 1. H

CH3

H i

O

CH3 ii

O

CO2(CH2)nBr

CO2H 1

H

CH3

O CO2(CH2)nR

3a~3g, 4a~4g

2a~2g

n= 2, 3, 4, 5, 6, 8, 10; 3a~3g: R=ONO2; 4a~4g: R= N

O

Scheme 1. Synthesis of the rupestonic acid derivatives. Reagents and conditions: (i) Br(CH2)nBr, NaOH, CHCl3, reflux, 4~10 h; (ii) morpholine or AgNO3, anhydrous acetonitrile, reflux, 10~15 h.

Acknowledgements: This work was financially supported by National Natural Science

Foundation of China (No.20872174), The Scientific-Research Plan of the Xinjiang High Technology (No.200910105) and China National Funds for Distinguished Young Scientists (No. 30925045).

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NEUROLOGICAL EFFECTS OF THE COMPOUNDS DERIVED FROM GOSSYPIUM HERBACEUM L. IN PC12 CELLS Y. X. Zhaoa, T. X. Dongb, J. Doua, A. Guob, H. A. Aisaa a

Key Laboratory of Plant Resources and Chemistry of Arid Zone, Xinjiang Technical

Institute of Physics and Chemistry, Chinese Academy of Sciences, 40-1 South Beijing Road, Urumqi 830011, Xinjiang, China b

The Hong Kong University of Science and Technology, Clear Water Bay, Hong Kong Gossypium herbaceam L., a cotton species that is widely cultivated around the world, is

an ethical herb used to treat mental retardation in Xinjiang, China. Its flower was officially listed as a Chinese medicinal herb and used as a sedative agent to treat delayed mental development and improve brain function. It is a complex mixture mainly contains of flavonoids. Through our research, G. herbaceam extracts could be considered as a potential agent for preventing or retarding the development or progression of Alzheimer’s Disease (AD). Here, 8 flavonoids (CH-1, CH-2, CH-3, CH-4, CH-5, CH-6, CH-7, CH-8) isolated from G. herbaceam and a criterion extract (CH-Z) were analyzed. The neurotrophic effect of these compounds was investigated by testing their effect on promoting cell survival and neuronal differentiation in PC12 cells. The neuroprotective effect of the compounds was also demonstrated by their ability to against oxidation-induced cytotoxicty in PC12 cells. The results demonstrated that these compounds from G. hirsutum did not possess any neurotrophic activity in potentiating or replacing the growth effect of serum in PC12 cells. At the same time, we found that the tested compounds did not promote any neuronal differentiation in stimulating neurite outgrowth in PC12 cells. However, when the cultures were pre-treated with vitamin C, it could significantly protect the cells against oxidation. It was shown that the pre-treatment of several compounds including CH-2, CH-4, CH-5, CH-8,

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and CH-Z could exert the anti-oxidation effect in protecting the tBHP-induced cell death in PC12 cells. Acknowledgements: The study was supported by the Natural Science Foundation of

autonomous region, Xinjiang (200821157), National Natural Sciences Foundation of China (0811331401) and National Key Technology R&D Program (2007BAI30B02).

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FATTY ACID COMPOSITION OF LIPIDS OF MICROALGAE J. F. Ziyavitdinov, U. J. Ishimov, R. Sh. Shouoqubov, Sh. I. Salikhov S. Sadykov Institute of Bioorganic Chemistry, Academy of Sciences of the Republic of Uzbekistan, 100143. Tashkent, Mirzo Ulugbek Street., 83. Fax (99871) 262 70 63, E-mail: [email protected]

As soon as the growing interest in biodiesel as an alternative to mineral diesel fuel, many see the deficit of oil in the cultivation of large amounts of oil crops. Produce more oil crops occupy the land for food crops. In addition, traditional oil crops - not the most productive and efficient source of oil plant origin. Therefore it is necessary to look for non-food raw materials for use. These include soap stock, fuzz, "multi source" meat-packing and poultry plants, jatropha oil, algae lipids. The aim of our study was to investigate the lipid content and fatty - acid composition four species of microalgae in Uzbekistan, which will be used later for biodiesel production. Microalgae were obtained from the collection of the Institute of Botany AS RUz. When cultured provide a combination of sufficiently large factors: selection of species of algae, density of crop, nutrition, growth phase, polyculture, as well as salinity, aeration, etc. Lipids of dry weight of microalgae isolated by extraction gasoline. The yield of lipids decreased in the order Chlorella vulgaris < Spirulina platensis. < Palmellocystis planctonica < Scenedesmus quadricatda. The obtained lipid contained 80% acylglycerols, waxes,

hydrocarbons, phospholipids, etc. Determination of the fatty acid composition of lipids obtained was carried out after esterification with methanol in alkaline conditions. Identification of the obtained fatty acid methyl esters was performed using GC/MS on "Hewlett Packard" HP 5972 with HP-5 MS detector. Mass - spectrometric data processed by database mass - spectra (Wiley 275.) In a result following fatty acids were found: lauric (C 12 : 0) 1.2 - 8.8%; myristic (C 14 : 0) 2.1 33.5%; palmitic (C 16 : 0) 33 - 68%; stearic (C 18 : 0) 4.3 - 16.9%; palmitooleic (C 16 : 1) 5.5 - 46.5%; oleic (C 18 : 1) 2.4 - 37 5%; linoleic acid (C 18 : 2) 1.0 - 15.1%; linolenic acid (C 18 : 3) 1.0 - 14.3%; arachidonic acid (C 20 : 4) 1.2 - 7.9 %.

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PRIMARY STRUCTURE OF ACTIVE CENTER OF LIPASE FROM FUNGUS PENICILLIUM MELINII J. F. Ziyavitdinov, Sh. I. Salikhov S. Sadykov Institute of Bioorganic Chemistry, Academy of Sciences of the Republic of Uzbekistan, 100143. Tashkent, Mirzo Ulugbek Street, 83, Fax (99871) 262 70 63, E-mail: [email protected]

It is known that the sequence of the active site of 70% of the lipase isolated from filamentous fungi consists of Gly-His-Ser-Leu-Gly-Gly-Ala, and hydroxyanion gap consists of a sequence Ile-Val-Val-Tyr-Leu-Val-Ile-Ala-Val-Ser-Phe-Arg-Gly and between the two active centers is still 72 amino acids. The aim of our study was to establish the primary structure of the active site of lipase isolated from the fungus P. melinii, compare the published data and identify the functional groups of amino acid radical’s tank, with which it is possible to immobilize the enzyme on a solid support while maintaining the original activity. For this purpose, lipase from the culture solution of fungus P. melinii was isolated. In the stepwise precipitation with acetone in the range from 33% to 75% in 1053 mg of protein with a specific activity of 6.7 U/mg is isolated. Further, the enzyme was isolated by gel filtration on a column of TSK HW-55f. In a result six fractions were obtained, and the third had a specific activity of 169 U/mg and the amount of protein was 100 mg. In the separation of obtained fractions by ion exchange chromatography on a column of DEAE TSK HW-650S were received four factions and the second had a specific activity of 1012 U/mg and the amount of protein was 34 mg. SDS - PAGE established its homogeneity with molecular mass of 29 kDa. Also pH and temperature optima was determined as 7.5 and 37 ºC, respectively. In order to establish the primary structure of the active site was excised from the gel band corresponding to the electrophoresis carried out hydrolysis with trypsin. Next, the sample was analyzed on the instrument Agilent 6340 Ion Trap LC / MS / MS. As a result, identified the primary structures of 28 peptide fragment. A search of the active site of lipase environment established sequences and fragments found in one peptide sequence-Gly-Ser-Leu-Ser-Leu-Gly-Gly-Ala-. This amino acid · 218 ·

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sequence differs from the well-known in the literature of the active sites of lipases in that place known -His- is replace with Ser-Leu-. Searching of oxyanions gap continues. Thus, in the course of studies established the primary structure of the active site of lipase isolated from the fungus P. melinii. In addition to the active site amino acids were not found radicals containing -NH2, -SH and -COOH groups. Therefore, when oriented immobilization of lipase on a solid matrix with -NH2, -SH and -COOH groups of the enzyme will not lose the original enzyme activity.

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CHEMICAL CONSTITUENTS FROM LEAVES OF CROTON LAEVIGATUS G. A. Zoua,b, H. A. Aisab, J. S. Yanga, Z. M. Zoua,* a

Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100193, People’s Republic of China; Tel: +86-10-62899756, E-mail: [email protected]

b

Key Laboratory of Chemistry of Plant Resources in Arid Regions, Xinjiang Technical

Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, People's Republic of China Croton laevigatus Vahl. (Euphorbiaceae) is an arbor distributed mainly in Yunnan,

Guangdong, and Hainan provinces of China. Its roots and leaves have been generally used as traditional medicines in Dai Nationality for the treatment of injury from fall, fracture, malaria, stomachache. In earlier work, we reported 7 new diterpenoids (6 cembrane skeletons and 1 trans-clerodane type) from the MeOH extract of the leaves of C. laevigatus. As part of our continuous investigation on this plant, 11 flavonoids were isolated, and their structures were identified by spectroscopic analysis as isorhamnetin (1), kaempferol (2), quercetin

(3),

kaempferol-3-O--L-arabinoside

(6′′-O-E-caffeoyl)--D-galactopyranoside kaempferol-3-O--D-galactoside

(5),

(7),

(4),

isorhamnetin-3-O-

isorhamnetin-3-O-rutinoside kaempferol-3-O-rutinoside

kaempferol-3-O--L-rhamnopyranosyl

(12)-

kaempferol-3-O--L-rhamnopyranosyl

(12)

-D-galactopyranoside [-L-

(6), (8), (9),

rhamnopyranosyl

(16)]--D-galactopyranoside) (10), and kaempferol-3-O--D- glucopyranosyl (13) [-L-rhamnopyranosyl(12)] [-L-rhamnopyranosyl (16)] --D-galactopyranoside (11), respectively. All compounds were isolated from this species for the first time, among which, compounds 4~7, 9~11 were firstly yielded from the genus Croton. The leaves of C. laevigatus were collected from Xishuangbanna County, Yunnan Province, in July, 2007, and

identified by Mr. C. Z. Peng. A voucher specimen (No. 20070716) has been deposited in the Herbarium of the Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences, Beijing. Acknowledgments: This work was supported by the Major Project of Chinese · 220 ·

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National Programs for Severe Infectious Diseases (2008ZX10003-006), National Natural Science Foundation of China (30900124), and the National S&T Major Special Project on Major New Drug Innovation (2009ZX09301-003). OCH3 OH HO

OH O

HO

O

OH

OR OH O

OH O

2 R=H

1 R=H 5 R=Gal 6 6 R=Glu 6

(E)-caff eoyl

4 R=Ara

Rha

7 R=Gal 8 R=Glu

6

9 R=Gal 2 10 R=Gal 2

OH

6

OH

Rha Rha Rha

Rha HO

O

Rha 6 11 R=Gal 3 2 Rha

OH OH O 3

Chemical structures of compounds 1-11.

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SCREENING OF THE ANTIBACTERIAL ACTIVITY, CYTOTOXICITY AND ANTIOXIDANT PROPERTIES OF EXTRACTS OF SOME UZBEK PLANTS S.A. Sasmakov1*, Zh.M. Putieva1, A.M. Nigmatullaev, Sh.S. Azimova1, U. Lindequist2 1

Acad. S.Yu. Yunusov Institute of the Chemistry of Plant Substances, Tashkent, Uzbekistan, e-mail*: [email protected] 2

Institute of Pharmacy, University of Greifswald, D-17487, Germany

The flora of Uzbekistan includes more than 4500 species of higher plants. More than 700 of these plants are used in traditional or conventional medicine [1]. Therefore, confirm their biological activities is essential to study these plants. The present study aims to evaluate the in vitro antibacterial, cytotoxic activities and antioxidant properties of extracts from 24 plant species belonging to different families. The extracts of Coronaria coriacea, Ligularia macrophylla, Otostegia bucharica, Phlomis bucharica, Salvia aethiopis, S. sclarea, Vaccaria segetalis and Zygophyllum gontscharovii showed remarkable antibacterial activity against Gram-positive bacteria Staphylococcus aureus (ATCC 29213) and Bacillus subtilis (ATCC 6059). The cytotoxicity

was measured by the “neutral red” uptake assay using 5637 cells, a human bladder carcinoma cell line (ATCC HTB-9). The remarkable activities were shown for Ecballium elaterium and Conium maculatum with IC50 values between 3.94 and 4.49 µg/ml. The DPPH

free radical scavenging assay was carried out for the evaluation of the antioxidant activity. The effective free radical scavenging of extracts were shown only in higher concentration (1000 µg/ml) and were 94.4%, 96.1% and 93.9% for Phlomoides labiosissima, Lactuca sp. and Tragopogon malicus, respectively. REFERENCES

1. Aprasidi G.S., Botirova Z.B., Irgashev Sh.B., Karimova S.U., Nigmatullaev A., Khalmatov Kh.Kh. et al. Medicinal means from plants of Abu Ali Ibn Sino (Avicenna), a Handbook (In Russian). Med Lit Publ Ibn Sino, Tashkent, 457, (2003). · 222 ·

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LIPIDS OF CORTUSA TURKESTANICA AERIAL PART D.T. Asilbekova, F.Yu. Gazizov, A.I. Glushenkova, A.M Nigmatullaev S.Yu. Yunusov Institute of the Chemistry of Plant Substances AS RUz, Tashkent, Uzbekistan, Fax: (99871) 120 64 75, E-mail: [email protected]

The lipids and fatty acids from dried aerial part of Cortusa turkestanica L. (Primulaceae family) has been studied for the first time. The total lipids from plant material were extracted by Folch method with chloroform-methanol (2:1, v/v), and their analysis were performed by TLC, GLC and GC-MS methods. Yield of the lipids was 4.3% of dry weight. The results of analysis by TLC shown, that the lipids consisted of typical for photosynthetic tissues of higher plants components set of the neutral lipids, glycolipids, and phospholipids. In the lipids it was revealed free fatty acids, triacylglycerols,

free

alkanols,

and

their

esters,

triterpenols,

sterols,

monogalactosyldiacylglycerols, digalactosyldiacylglycerols, free sterylglycosides and their esters,

phosphatidic

acids,

phosphatidylcholines,

lysophosphatidylcholines

and

phosphatidylinositols. The major constituents of them were galactolipids and free fatty acids. Content of the unsaponifiable compounds in lipids was 15.6% which contained hydrocarbons (29.7%), fatty and isoprenoid alkanols (27.1%), triterpenols and sterols (35.2%), carotenoides, chlorophylls, and unidentified components (sum of 9.7%) The fatty acid composition of lipids characterized as their methyl esters by GLC on an Agilent GC 7890 apparatus equipped with НР-5 (30м x 0,25мм i.d.) capillary column. The fatty acid composition were as (%, GLC): 12:0 - 1.0, 14:0 - 4.2, 16:0 - 27.0, 17:0 - 1.1, 18:0 4.3, 18:1(9Z) - 38.2, 18:2 - 11.4, 18:3(9Z,12Z,15Z) - 2.3, 18:3(6Z,9Z,12Z) - 1.0, 18:4(6Z,9Z,12Z,15Z) - 6.9, 20:0-1.3, 20:1(11Z) - 1.3, 22:0 - trace; sum of unsaturated acids – 61.1; sum of saturated acids – 38.9; sum of polyenoic ω3 and ω6 acids - 10,2. The obtained results induced that the lipids from photosynthetic tissues of Cortusa turkestanica contain Δ6 polyenoic octadeca-6Z,9Z,12Z-trienoic (γ-linolenoic) and

octadeca-6Z,9Z,12Z,15Z-tetraenoic (stearidonic) acids, and availability of these acids could be taxonomic markers for differentiation of Primulaceae family species. This work was supported by grant FА-FЗ-ТО46 of AS RUz. · 223 ·

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CONVERSION OF SONGORINE INTO RELATED ALKALOIDS OF SOME ACONITUM SPECIES B.T. Salimov*, N.D. Abdullayev Akad. S.Yu. Yunusov Institute of the Chemistry of Plant Substances, AS,100170, Tashkent, Uzbekistan

Songorine (1) discovered for the first time in the plant Aconitum soongoricum was found after in A. carmichaeli, A. karakolicum, A. monticola, A. volubile. It was converted into 1-dehydrosongorine (2) isolated early from A. finetianum. Conversion of 1 into 12-epi-19-dehydronapelline (3) and 19- dehydronapelline (4) isolated for the first time from A. liangshanum and A. flavum respectively was made through step of

formation of

12-epinapelline (5) and napelline (6) by their ozonated oxygen oxidation. It was found that compounds 3 and 4 are in ratio 3:1. It was established that isosongorine (7) yielded in high quantities in the Klemmensen reduction conditions of 1. It was also established that stable 12-epi-12-tosyloyl-19-dehydronapelline (8) is derived from 3 in p-toluyensulfochloride dehydratation conditions. R

O CH2

16

11

CH2

O

17

OH 20

O

13

CH2 N

14 1

N 4 19

8

N

OH

6

18 CH3

CH3

OH CH3

1 R

OH

O

15

10

R1

3. R=H, R1=OH 4. R=OH, R1=H 8. R=H, R1=OSO2C6H4CH3

2

R1 CH2

OH

O CH3 OH

N

OH

N

CH3 5. R=H, R1=OH 6. R=OH, R1=H

O CH3

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OBTAINING DRY EXTRACT FROM PLANT GERANIUM SAXATILE D.R. Siddikov, B.M. Makhmudova, S.Z. Nishanbaev, G.B. Sotimov S.Yu. Yunusov Institute of the Chemistry of Plant Substances Academy of Sciences 100170, Tashkent, Uzbekistan, fax (99871) 120 64 75, e-mail: [email protected]

Plant genus Geranium of Geraniaceae family is widely spread all over the world. There have been described 300 species of plants of the current genus, among of which 13 are grown in Uzbekistan. The aim of research was to determine the extraction conditions from the overground and also from the roots and rhizomes of Geranium saxatile. It’s known that extraction of biologically active compounds depend from degree of powdering and selection of an optimal extragent. Therefore to obtain extractive compounds the plant’s parts were dried in room temperature and powdered up to the particles size of 3–5 and 5–8 mm. Ethanol as extragent was used in different concentrations (20%, 40%, 60%, 80%, 90%). Obtained concentrated extracts were dried in 100C up to the constant dry matter weight. Obtained sums of extracts were estimated by gravimetric method. Table 1. Yield of extractive substances dependent from concentration of ethanol and parities size, % Particles size, mm

3–5 mm

5–8 mm

Concentration of ethanol, % 20 40 60 80 90 20 40 60 80 90

Yield of extractive substances,% Aerial part Roots and rhizomes 14.17 27.4 13.2 25 12.1 24.6 11.5 24.39 10.1 20.1 11.7 23.7 10.97 23.3 10.1 22.1 9.73 22.0 8.95 19.3 · 225 ·

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From the Tabl.1 we can see that with increased of particles size and of concentration of ethanol the yield extractive substances is reduced. The optimally size of particles is 3–5 mm and optimally concentration of ethanol is 20%. Extract of aerial part has brown color with green hue, and extract from roots and rhizomes has dark grayish–brown color. All species of Geranium contain tannins, which have a wide spectrum of pharmacological activity. Aerial part and roots contain tannins up to 10.2% and 16.1% accordingly.

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SYNTHESIS OF ISOQUINOLINE ON THE BASE OF HOMOVERATRYLAMINE AND PHTALIC ACID A. Sh. Saidova, M. Alimovaa, V. I. Vinogradovab a) Samarkand State University, University Blvd., 15, Samarkand, 703004, Uzbekistan b) S.Yu.Yunisov Institute of the Chemistry of Plant Substances, 700170, Toshkent, Republic of Uzbekistan

The isoquinoline alkaloids form a large secondary metabolites, many of which are pharmacologically important. Our synthetic studies on biologically active isoquinoline alkaloids have led to a number of total syntheses. Homoveratrylamine (1) with phthalic acid(2) and phtalic anhydride (3) boiling benzene afforded N-[2-(3,4-dimethoxyphenyl)ethyl]phtalimide (4).

O O

H3CO H3CO

NH2

+

3

O COOH

H3CO N

H3CO

O

O

1 2 H3CO H3CO

4

COOH H3CO

NH O

COOH

1. POCl3 2. NaBH4

NH

H3CO

COOH 6

5

The hydrolisis of homophtalimide 4 produced amido acid 5. Amide 5 was subjected to a B’shler-Napieralski reaction with phosphoryl chloride. Obtained 3,4-dihydroisoquinoline was converted into tetrahydroisoquinoline 6 by reduction with NaBH4.

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LIPIDS OF AJUGA TURKESTANICA Sh.K. Khidoyatova, N.T. Ulchenko, S.D. Gusakova, A.M. Nigmatullaev, Sh.Sh. Sagdullaev S.Yu. Yunusov Institute of the Chemistry of Plant Substances, 77, Mirzo Ulugbek str., Tashkent, 100170, Republic of Uzbekistan, e-mail: [email protected] Ajuga turkestanica (Rgl.) Briq. (Lamiaceae) is the endemic wild-growing plant of

Uzbekistan. On the basis of ecdysteroids and iridoid glycosides of this plant several medicinal preparations are created in our institute, and their substances are being produced at a moment. Among them there are lactation stimulating remedies and the medicines with adaptogenic, tonic, choleretic action. We have investigated the lipids of flowers and roots of A. turkestanica, being collected in 2011 in the Surkhandarya region at a flowering phase and also the lipids of the seeds of the 2010’s crop. The flowers had humidity – 30.2%, the roots – 4.2%, the seeds – 7.3 %. The general lipids from the flowers and the roots have extracted three times with mixture of chloroform and methanol (2:1, v/v) with a yield of 4.27 and 2.0 % (on а.d.w.) accordingly. Free lipids of the seeds (FLS) have extracted with gasoline using Soxlet’s apparatus and the yield of free lipids was 2.9 %. The bound lipids of seeds (BLS) have extracted from residuary (residual) raw material in similar way as the general lipids of flowers and roots with a yield of 2.3 %. The fatty acids have been isolated from lipids by hydrolysis with potassium hydroxide in methanol. Using diazomethane the methyl ethers of fatty acids have been obtained and further purified by preparation TLC in system of hexane - diethyl ether (8:2, v/v). Methyl ethers of fatty acids have analyzed by GLC method on Agilent Technologies 6890N apparatus with flame ionization detector, the 30 m at length capillary column and HP-5 phase at temperature from 60 to 250оС.

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Table. Fatty acids of lipids from Ajuga turkestanica by GLC-data (%)

Fatty acids

The sum of fatty acids

Plant organ

10:0 15:0

16:0

16:1

18:0

18:1

18:2

20:0 + 22:0

Flowers

3.0

41.0

0.4

7.4

35.6

8.9

3.6

55.1

44.9

Roots*

3.9

26.0

2.5

4.7

20.1

32.2

9.7

44.3

54.8

FLS**

0.8

18.7

0.6

3.6

37.7

35.4

1.6

24.7

73.7

BLS

2.2

43.6

-

7.3

27.4

19.5

-

53.1

46.9

Saturated Unsatu-rated

*at roots there are 0.9% 24:0, ** in free lipids of seeds – 0.5 % 20:1, and 1.0 % 22:1. Data in the table shown 16:0 and 18:1 fatty acids prevailing among the lipids of flowers and in bound lipids of seeds, 16:0 and 18:2 – among lipids of roots, 18:1 and 18:2 – among free lipids of seeds.

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CHEMICAL COMPONENTS AND BIOLOGICAL ACTIVITY OF SCUTELLARIA SCHACHRISTANICA AERIAL PART Z. O. Toshmatov1, K. A. Eshbakova1*, Kh. M. Bobakulov1, S.A. Sasmakov1, U. Lindequist2 1) S.Yu.Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences, 100170, Tashkent, Republic of Uzbekistan, e-mail:[email protected] 2) Institute of Pharmacy, Department of Pharmaceutical Biology, University of Greifswald, D-17487, Germany

We studied the chemical composition of Scutellaria schachristanica Zuzepezuk aerial part during blossoming time, which grows in the Samarkand region of Uzbekistan. We have isolated 14 known compounds and one new flavone glycoside named as shachristanoside from ethylacetate fraction by column chromatography. Structures of isolated compounds have been established on the basis of their physical and chemical properties and the analysis of their spectral data IR , UV, 1H, 13C NMR, DEPT. The isolated compounds have been identified as β-sitosterol (1), chrysin (2), vogonine (3), 3,5-dihydroxy-7-metoxyflavone (4), oroxylin (5), 5,7-dihydroxy-3-metoxyflavone (6), apigenin (7), hispidulin (8), scutellarein (9), chrysin-7-O-methylglucuronide (10), chrysin-7-O-glucuronide

(11),

5,4′-dihydroxyflavone-7-O-glucoside

scutellarein-7-O-β-glucoside (13) shachristanozid (14) and sugar (15). CH2 OH O OH

R1 R2

OH

O

OH

R5

O

HOCH2 O

R3

R4 OH

HO

1

CH2 OH

O

2-14

· 230 ·

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OH

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R1

R2

R3

R4

R5

2

Н

ОН

Н

Н

Н

3

OCH3

OH

Н

Н

Н

4

Н

OCH3

Н

ОН

Н

5

Н

ОН

OCH3

Н

Н

6

Н

ОН

Н

OCH3

Н

7

Н

ОН

Н

Н

ОН

8

Н

ОН

OCH3

Н

ОН

9

Н

ОН

ОН

Н

ОН

10

Н

D-GlcUA Met.esther

Н

Н

Н

11

Н

D-GlcUA

Н

Н

Н

12

Н

Glu

Н

Н

ОН

13

Н

Glu

ОН

Н

ОН

14

H

D-Glu-L-Ara

H

H

H

Methanolic and chloroform extracts were studied in biological activity with method in vitro. These extracts showed strongly pronounced cancer, antioxidant and antibacterial

activity. All compounds have been isolated from S. schachristanica for the first time.

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Compounds

PURIFICATION OF N-METHYLCYTISINE FROM WASTES OF CYTISINE MANUFACTURE R.A. Botirov, G.B. Sotimov, V.I. Vinogradova, A.U. Mamatkhanov, A.Z. Sadykov, Sh.Sh. Sagdullaev, A.A. Azamatov, F.M. Tursunkhodjaeva S.Yu.Yunusov Instutute of the Chemistry of Plant Substances, Academy of Sciences Republic of Uzbekistan, e-mail: [email protected]

The manufacture of analeptic medicinal preparation cytisine from aerial part of Thermopsis alterniflora was organized in the Pilot manufacturing of the Institute of the Chemistry of Plant Substances, Uzbekistan. After cytisine isolation the rest alkaloid sum contains fair quantities of biologically active alkaloid N-methylcytisine. We worked out a technology for its isolation from this sum. According this method N-methylcytisine is extracted by benzene and evaporated to dryness. Solid residual dissolved in extraction benzene at heating and boiled with active carbon, then filtered. Residue appeared during evaporation then removed, washed by extraction benzene and air dried. Yield of final product is 15% from mass of air dried waste. Pharmacological

investigations

show

N-methylcytisine.

· 232 ·

expressed

antitoxic

activity

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ON PHARMACOLOGY OF DITERPENE ALKALOIDS DESOXYDELCORINE, DELCORINE, DEMETHYLENEDELCORINE AND C-6-BENZOYLDELCORINE F.N. Dzhakhangirov, J. Rejepov*, F.M.Tursunkhodjaeva, B.T.Salimov S.Yu.Yunusov Instutute of the Chemistry of Plant Substances, Academy of Sciences Republic of Uzbekistan, e-mail: [email protected]

Diterpene alkaloids desoxydelcorine (1), delcorine (2), demethylenedelcorine (3) and C-6-benzoyldelcorine (4) were isolated from Delphinium plants. OCH3 OCH3

(1) R1= H, R2 = R3 = CH2, 1

10

4

(2) R1= OH, R2 = R3 = CH2,

8

N 6

R1

O O

(3) R1= OH, R2 = R3 = H,

R3

(4) R1= OCOC6H5, R2 = R3 = CH2

R2

H3CO

Comparative pharmacological investigations of acute toxicity on mice, effects on arterial pressure, breath, peripheral nervous system on narcotized cats, as well as on adren-, cholinand hystaminergic structures had been carried out. Local anaestetic, analgesic and antyarrhythmic activity of these substances had been investigated. LD50 for desoxydelcorine (1) was 46.5 mg/kg (i.v.) and 235 mg/kg (i.p.). Introduction of OH-group to C6 (2) lead to decreasing of toxicity for 2.5 times. Desintegration of methylenedioxy group at C7-C8 (2) and formation of (3) lead to insignificant decreasing of toxicity. Apperance of benzoyloxy group at C6 (4) resulted in increasing of toxicity for 2.5-2.6 times as compared with (2) and (4). Investigated substances displayed short-term weak hypotensive and peripheral N· 233 ·

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ganglioblocking activity. At i.v. injection they had protective antiarrhythmic action at arrhythmias caused by aconitine, CaCl2, strophantine K in anaesthetized rats, and also in coronary artery occlusion in dogs. In antyarrhythmic activity they exceeded Quinidine (5) and Novocainamide (6). In contrast to (5) and (6) the investigated substances show high neuroprotective effects. Their injection to mice poisoned by fatal doses of aconitine improved neurointoxication symptoms and prevented death of 50-80% animals. (1) – (3) didn’t exert local anesthesia in concentrations up to 1%, (4) in concentration 0.5% caused terminal anesthesia of rabbit cornea. Substance (4) in contrast to (1) – (3) in doses 5-10 mg/kg had analgesic activity in hot-plate and acetic acid writhing tests.

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ON PHARMACOLOGY OF DITERPENE ALKALOIDS ELDELIDINE, DEMETHYLENEELDELIDINE, C-6-ACETYLELDELIDINE AND C-6-BENZOYLELDELIDINE F.N. Dzhakhangirov, J. Rejepov*, F.M.Tursunkhodjaeva, B.T.Salimov S.Yu.Yunusov Instutute of the Chemistry of Plant Substances, Academy of Sciences Republic of Uzbekistan, e-mail: [email protected]

Comparative

pharmacological

investigations

of

alkaloids

eldelidine

(1),

demethyleneeldelidine (2), C-6-acetyleldelidine (3) and C-6-benzoyleldelidine (4) from Delphinium sp. had been carried out. OCH3 OCH3

(1) R = Н,

10

1

H5 C 2

OCH3

OH

(2) R=ОН,

8

N

O

6

4

O CH3

(3) R = СОСН3,

OH

(4) R = СОС6Н5

OH

O R

LD50 (i.v., mg/kg) in mice was (1) – 235, (2) – 230, (3) – 136, (4) – 16.1. On narcotized cats all substances caused short-term hypotensive effect, decreased frequency and insignificantly increased amplitude of heartbeat. Neurophysiological and pharmacological analyses of studied alkaloids influence on peripheral branch of vegetative nervous system shown that hypotensive effects of (1) – (3) based on N-acetylcholine blocking action, and (4) – on N-choline blocking, spasmolytic and cardiodepressive action. All investigated substances exerted antyarrhythmic action at arrhythmias caused by aconitine, CaCl2, strophantine K in anaesthetized rats, and also in coronary artery occlusion · 235 ·

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in dogs. In antyarrhythmic activity (1) – (3) were close, and (4) exceeded Quinidine (5), Lidocaine (6) and Novocainamide (7). In contrast to (5) – (7) the investigated substances show high neuroprotective effects. Their injection to mice poisoned by fatal doses of aconitine improved neurointoxication symptoms and prevented death of animals. Substance (4) in concentrations 10-20 mkl/l reversibly inhibited TTX-sensitive inward Na+-current in rat neurons of sensor ganglia and cardiomyocytes and didn’t influence substantially on K+ and Ca2+-currents. Substance (4) also displayed high local anaestetic and analgesic activity exceeded cocaine, acetylsalicylic acid and metamisole. (1) – (3) exerted analgesic activity in doses 50-100 mg/kg.

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A NEW SECOIRIDOID GLYCOSIDE FROM FRAXINUS RAIBOCARPA K. A. Eshbakova, Kh. Sh. Kamoldinov, Kh. M. Bobakulov, N. D. Abdullaev S.Yu.Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences, 100170, Republic of Uzbekistan, Tashkent, prosp. M. Ulugbek 77, e-mail: [email protected]

Earlier from Fraxinus raibocarpa Rgl. (Oleaceae) we have isolated tyrosol, 2-(4-hydroxyphenyl) ethyl-β-D-glucopyranoside (salidroside), 7-ketologanin, mannit and rutin [1]. Continuing our phytochemical researches, we have investigated the aerial parts of Fraxinus raibocarpa collected in the Tashkent region of Uzbekistan, in the flowering phase.

By the column chromatography of an alcoholic extract of butanol fraction on silica gel, we isolated a new secoiridoid glycoside – named as raibocarpaoside (1), with the composition C18H26O11. Structure of isolated compound have been established on the basis of their physical and chemical properties and the analysis of their spectral data IR, UV, 1H,

13

C NMR, DEPT,

NOESY, Hetcor Thus,

raibocarpaoside

is

a

new

secoiridoid

glycoside

and

has

structure

1-О--D-glucopyranosyl-4,6-dicarboxymethyl-8-methyl-7,8-seco-cyclopent-8-en[c]-1,9-dih ydropyrane.

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Chemistry

O 6

3 C OCH 12

5 9

7

O

8 10

CH3

6' CH

2 OH

5'

OH

3 1

O

O

O

OH 3'

Compounds

11

13

H3CO

of Natural

1' 2'

OH REFERENCE

1.

H.Sh. Kamoldinov, K.A.

Eshbakova, Kh.M. Bobakulov, N.D. Abdullaev, Khem.

prirod.soedin., 398 (2011)

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IMMUNOMODULATING INFLUENCE OF ECDYSTEN IN THE TREATMENT OF GIARDIASIS IN PATIENTS WITH PULMONARY TUBERCULOSIS J.I. Islamova*, N.A. Davis**, V.N. Syrov*, S.O. Osipova** Academician S. Yu. Yunusov Institute of Chemistry of Plant Substances of Academy of Sciences of the Republic of Uzbekistan, Tashkent, 100170, 77, Mirzo Ulugbek str., fax (99871) 120 64 75; e-mail [email protected] Research Institute of Epidemiology, Microbiology and Infectious Diseases of the Ministry of Public Health of the Republic of Uzbekistan**

Concomitant parasitic diseases could modify immune state of patients with pulmonary tuberculosis (PT), inhibiting protective response. TNF-α is known to be fundamental for initiation of granulomatous reactions, restricting inflammation focus and exerting protective effect in PT (Welsh et al., 2008). TNF-α is of protective significance in giardiasis (Gr), especially in early stages (Zhou et al., 2007). Previously we found that Gr in patients with PT is resistant to metronidazole in 43,3% of ecdysten

(Ec),

preparation

from

the cases, but successfully treated with

phytoecdysteroids

class,

with

hepatoprotective,

immunomodulating and other properties. We evaluated influence of concomitant Gr on the TNF-α level in patients with infiltrative PT and its dynamics after Ec treatment. Level of serum TNF-α was estimated by ELISA in patients with PT, free of parasites, patients with PT+Gr, patients with Gr without PT and healthy individuals. TNF-α concentration in sera of healthy individuals

amounted to 5,1±1,2 ng/ml, in patients with Gr without

concomitant infections - 5,0±2,0 ng/ml. These patients were disable to spontaneous elimination of G. lamblia (results of a month observation). Low TNF-α level in these patients is in the accordance with data of Zhou et al. on protective role of TNF-α in Gr. Level of TNF-α

in patients with PT without parasites amounted to 22,2± 4,3 ng/ml,

concomitant Gr decreased this value to 7,3±2,0 ng/ml. It can be considered as inhibition of cytokine production which is of protective role in the PT control. Ec eliminated G. lamblia in all the cases and improved patients state. Almost 4-fold increase of TNF-α concentration after the Ec course ( up to 97,0± 22,9 ng/ml) in patients with PT +Gr can be considered not only as the result of neutralization of inhibiting effect of Gr on TNF-α synthesis, but as stimulation of protective antituberculosis immunity by Ec. · 239 ·

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EVALUATION OF PHARMACOLOGICAL PROPERTIES OF PROANTHOCYANIDINS FROM ALHAGI PSEUDALHAGI Z.A. Khushbaktova, Z.A. Kuliev, Sh.Sh. Sagdullaev Academician S. Yu. Yunusov Institute of chemistry of plant substances of Academy of Sciences of the Republic of Uzbekistan, 100170, Tashkent, Mirzo Ulugbek str., 77 fax: (99871) 1206475; e-mail: [email protected]

The research which was conducted in order to study the pharmacological activity of total proanthocyanidins extracted from plants growing in Uzbekistan (Rhodiola Semenovii, Rhodiola pamiroalaica, Rhodiola rosea, Quercus robur, Alhagi pseudalhagi, Hypericum perforatum, Plautanus orientalis, Polygonum coriarum, Punica granatum, Thea sinensis and others) showed that most of them exhibit a wide spectrum of biological activities [1,2]. The most expressed effect among the studied compounds was shown by the total polymer proanthocyanidins from Alhagi pseudalhagi - alkachine. When Alkachine was applied into the incubation containing homogenate of liver, it inhibits lipid peroxidation (LPO) induced by iron depending on the concentrations (10 - 100 ug/mL) at 65-85%. Similar effects are observed in in-vivo experiments of Alkachine (per os 3-7 days) on animals under conditions of endogenous, tritone, ethanol, adrenaline hyperlipidemia and hyperlipidemia induced by an atherogenic diet containing methyluracil. In the meantime, along with inhibition of LPO (reduction of diene conjugates, malondialdehyde) Alkachine has also contributed to the activation of enzymes EPA, reduction of atherogenic lipoproteins. A similar normalization of lipid disorders in the application Alkachine was noted in experimental atherosclerosis and myocardial infarction (coronary artery occlusion). Moreover, the application of Alkachine led to positive changes in the pathology of the disturbed carbohydrate metabolism of myocardium, reflecting the activation of aerobic oxidation processes. Existing work shows that the drugs developed from polymeric proanthocyanidins can find a good use for preventive-curative and therapeutic purposes of diseases of cardiovascular system among number of modern means possessing antihypoxia and antioxidant activities. REFERENCES 1. K.H Kim, Z.A. Kuliev, A.D. Vdovin et al, Chem. Nat. Comp., 771 (1991). 2. C. Goncalves, T. Dinis, M. Teresa, Phytochemistry, 66, 89 (2005). · 240 ·

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AJUGA TURKESTANICA AND PREPARATIONS DEVELOPED ON ITS BASIS V.N. Syrov, F. Egamova, G.I. Ismailova, A.U. Mamatkhanov, Sh.Sh. Sagdullaev S. Yu. Yunusov Institute of chemistry of plant substances of Academy of Sciences of the Republic of Uzbekistan, Tashkent, 100170, fax

77, Mirzo Ulugbek str.,

(99871) 120 64 75; e-mail [email protected]

Ajuga genus includes more than 50 plants species growing on Europe-Asian continent

and partially in Africa. Some species occur rather rarely and they are endemic for some regions of the world. Ajuga turkestanica (Rgl) Brig. is an endemic plant of Uzbekistan. Compounds dominated in A. turkestanica (Rgl) Brig. are phytoecdysteroids: ecdysterone, cyasterone, 22-acetylcyasterone, turkesterone, etc., and iridoid glycosides: garpagide and 8-O-acetylgarpagide. On the basis of biologically active compounds of this plant medicinal preparations were developed: ecdysten (tonic, stress-protective and anabolic effects) and ayustan (optimizes metabolic processes, lactostimulating and immunomodulating effects). Besides, biologically active additives (BAD) were developed: exsumid, ecdysten plus and jisten. Exumid and ecdysten plus are applied as adaptogenic and actoprotective remedies. Recently they have been successfully used in sport medicine. BAD jisten improves metabolism of tegumental tissues. Jisten stimulates aquaporins synthesis, bettering liquid circulation among skincells and contributing to skin humidification, eventually influencing on skin beauty, softness and velvetiness. At present we are studying iridoid glycosides from A. turkestanica as a potential calmatives in increased nervous excitability, neuroses, neurocirculatory dystonia, insomnia. It was found that iridoid glycosides exert positive influence on processes of bile secretion. Thus comprehensive chemical and pharmacological study of A. turkestanica (Rgl) Brig has already contributed to introduction in practical medicine and cosmetology a number of preparations and BADs of metabolic type of action and also opened the real prospect for development of new efficient sedative remedies. Raw stock of the plant is easily renewed due to application of aerial part mostly. Picking of the plant doesn’t damage ecology in the regions of its growing.

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TECHNOLOGY FOR OBTAINING SONGORINE ALKALOID FROM AERIAL PART OF ACONITUM MONTICOLA O.T. Juraev, M.N. Sultankhodjaev, Sh.Sh. Sagdullaev, A.Z. Sadykov, F.N. Dzhakhangirov, A.M. Nigmatullaev S.Yu.Yunusov Instutute of the Chemistry of Plant Substances, Academy of Sciences Republic of Uzbekistan, e-mail: [email protected]

Aerial part of Aconitum monticola is containing valuable quantities of alkaloids, among them songorine considered as a main alkaloid. Content of songorine in the plant is achieved up to 0.3% from air-dried mass depending stage of vegetation and plant collection area. Songorine is an intermediate product for obtaining another antiarrhythmic substance. We elaborated technology for songorine manufacturing from the plant. Crushed plant material is extracted by ethanol, condensed to water residue, and floating lipid-protein complex filtering or decanting. The obtained water residue alkalinized with pregnant solution of soda, extracted by chloroform, alkaloids separated by sulphuric acid solution and washed by chloroform. After alkalinization of sulphuric acid extract by pregnant solution of soda alkaloids extracted with chloroform and evaporate to dryness. Yield of obtained alkaloids sum is 0.67% from air-dried plant. Sum of alkaloids dissolved in methanol and songorine hydrochloride precipitated with spirit solution of hydrochloric acid. Yield of obtained product is 0.2% from air-dried plant.

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ON ACID-WATER EXTRACTION – ULTRAFILTRATION TECHNOLOGY FOR SOME BIOLOGICALLY ACTIVE ALKALOIDS PRODUCTION FROM LOCAL PLANTS Sh.Sh. Sagdullaev, A.Z. Sadykov, M.E. Tursunova, N.V. Valiev, O.T. Juraev, R.A. Botirov S.Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences Republic of Uzbekistan, e-mail: [email protected]

There are some methods for manufacture of alkaloids drug substances by plants extraction with lean solutions of different mineral or organic acids and following liquid-liquid extraction from alkalinized water-acid extract. Substantial imperfection of such methods is the formation of stable emulsions on following liquid-liquid extraction stage. Formation of stable emulsions in liquid-liquid extraction with organic solvents is caused by presence of co-extracted surfactant species (proteins, polysaccharides, lipids etc.) impeding phase separation. We have used ultrafiltration in order to separate extractive substances by their molecular weights. We investigated possibility to use some types of membrane (pore sizes 0.01 mk, 0.05 mk, 0.1 mk, 0.15 mk) to remove the abovementioned high molecular surfactant species from crude extract of alkaloids. Successful results were obtained using membrane No.5 (pore size 0.01 mk) that fully prevented appearance of emulsion. As result the uniform technology for obtaining alkaloids with different basicity using plants extraction by water of lean solutions of different mineral or organic acids, following ultrafiltration and liquid-liquid extraction of target product. Technology for batch manufacturing of antiarrhythmic drugs allapinine, aklesine, axaritmine, anticholinesterase drug galantamine hydrobromide, expectoration lycorine hydrochloride, arrhythmogenic substance aconitine was developed.

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FEATURES OF PHARMAСOLOGICAL ACTIVITY OF SEMISYNTHETIC DERIVATIVES OF IMPERIALINE – DIHYDRO- AND ISODIHYDROIMPERIALINE Yu.R. Mirzaev, R. Shakirov Republic of Uzbekistan, Tashkent 100170, Mirzo Ulugbek st. 71, Institute of Chemisrty, of Plants Substances, Ac. Sci. R. Uz., e-mail: [email protected]

Alkaloid Imperialine (1) isolated from Petilium (Fritillaria) related to cevane group of steroidal alkaloids. Ester derivatives of imperialine at C-3 and haloid derivatives (Cl, I, Br) are available. These compounds are known as selective M2-cholinoblockers, they eliminate arecoline tremor, revealed expressed anxiolytic effect in several tests, have revealed nootropic and antiaggressive activity. Here we want present chemical and pharmacological features of C-6 imperialine derivatives – dihydroimperialine (2) and isodihydroimperialine (3). They were synthesed by Imperialine reduction by Na in butanol and sodium borohydricum in methanol with subsequent separation on column. Such structural modification have leaded to severe changes of pharmacological activity of mentioned C-6 derivatives. In opposite to C-3 imperialine derivatives they loss M2-cholinoblocking activity, increased arecoline tremor, caused psychomotor and reflectory excitability, tremor and seizures. In opposite to C3 derivatives they revealed anxiety in psychopharmacological tests, increased

aggressivity

of

mice.

Pharmacological

activity

of

dihydroimperialine

approximately for 30% more expressed, compared with activity of isodihydroimperialine. So, carbonyl group in molecules of imperialine and it C3 derivatives plays important role in expressing of specificity of their pharmacological activity.

Imperialine (1)

Dihydroimperialine (2)

· 244 ·

Isodihydroimperialine (3)

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THE ROLE OF STEROIDAL ALKALOIDS IN TREATMENT OF CIRCULATORY SYSTEM DISORDERS Yu.R. Mirzaev Republic of Uzbekistan, Tashkent 100170, Mirzo Ulugbek st. 71, Institute of Chemisrty of Plants Substances, Ac. Sci. R. Uz., e-mail: [email protected]

Hundreds of drugs of different classes are using for treatment of сirculatory system diseases, but the problems are known. Here presented significance of steroidal alkaloids as unique preparations in management of circulatory system disorders in past, present and its possible role in future. In the middle of past century alkaloids of Veratrum were widely used in treatment of hypertension, in particular connected to pregnancy toxicosis. About 30 drugs on Veratrum base were created in Western Europe and North America, but in 80-ties were partly displaced, due to side effects, including nausea. But in recent years mean for decrease of nausea elaborated; it was established in experiments, that germine esters are more comfortable as drugs, than protoverine esters; Veratrum preparations reveal hypotensive effects in cases, where others were failed. Besides, it was discovered its ability to surpass of multiresistance to different drugs, including hypotensives. These findings would promote the widening application of Veratrum alkaloids in medicine, as practical, as scientific. In recent years Cyclovirobuxine from Box tree was included in medicine as potent antianginal drug with concomitant antiarrhythmic, antioxidant, antihypoxant and hypocholesterolemic activities. Evaluation of other Box tree alkaloids or alkaloids sum as drug is actual. Alkaloid of Fritillaria, Sevedinine in equal doses simultaneously reveals antagonism to aconitine, CaCl2, MgSO4 models of arrhythmias. In “therapeutic” doses it has selective M2-cholinoand β1- adrenoblocking activities. It can provide neurogenic blockade of heart that sometimes will be useful for damaged heart. Derivative of Fritillaria alkaloid imperialine – iodemethylat imperialine is potent selective M2-cholinoblocking compound. It doesn’t block M3,4-receptors

of

secretory

and

smooth

muscle

· 245 ·

organs

and

doesn’t

penetrate

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throughhematoencephalic barrier. So, this compound has number of preferences compared with atropine, that using in cardiology. Diacethylsevedine from Korolkowia has high antiarrhythmic activity of I class, but increase electrical excitability of right auricle or sinus node. Pregnane alkaloids of Veratrum – Veralosine and Veralosinine have showed high expressed cardiotonic activity and by therapeutic width they surpass natural cardiac glycosides. In conclusion it may be note, steroidal alkaloids of Veratrum. Korolkowia, Fritillaria, Buxus geni plants are displaying simultaneously the combination of desirable pharmacologic activities. This combinations make these compounds original, sometimes unique drug preparations, that used in past, using now and would be introduced in future, as principally new drugs for circulatory pathology treatment.

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WATER SOLUBLE COMPLEX OF ANTIBACTERIAL PREPARATION NITROXOLIN A. M. Khvan, R. K. Karimov S.Yu. Yunusov Institute of Chemistry of Plant Substances of Sciences Republic of Uzbekistan, 100170. Uzbekistan, Tashkent,

fax 98711206475

The essential insufficiency of the known preparation Nitroxolin, possessing by antibacterial activity, is its low solubility in water and therefore a low biological accessibility. One of the efficient ways for increasing medicinal materials solubility is the including them to polyelectrolyte matrix. In the given work the process of the formation of macromolecular complex of Nitroxolin (5-NOK) with natural polyelectrolyte pectin (P) was studied. The formation of ionic linkages between carboxylic groups of pectin and nitrogen in the medicinal molecule is reflected on the shifts of the potentiometer titration curves of the solutions with the increasing of the Nitroxolin content. The results of the viscosimetric investigations show possible presence of the hydrophobic interaction alongside with ionic bindings in the studied system. The contribution of each type of the interaction to hydrodynamics of the complex solution is defined by the ratio of components and pH value. The received complex P - Nitroxolin is water soluble.

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TRANSFORMATION ON the BASE OF NORFLUOROCURARINE F.X.Yuldashev, M.M.Mirsaeva B.Tashkhodjaev, M.G.Levkovich, N.D.Abdullaev

S.Yunusov Institute of Chemistry of Plant Substanses Tashkent, Fax: 998(71)1206475, E-mail: [email protected]

Nowadays a question of modification natural materials of easy to isolation for reception on their basis new bioactivic compounds becomes more actual. One of perspective substance in this respect is norfluorocurarine (vincanine) (1) - the basic alkaloid of plant Vinca erecta. The purpose of the present work is norfluorocurarine transformation for

obtaining new derivants. Norfluorocurarine

(1)

at

reduction

N(β)-methyldihydrodesfluorocurarine

forms

is

bisindolic

(obtained

(4)

alkaloids

by

(2,

3).

hydrogenation

N(β)-methylnorfluorocurarine) is derived in disclosing of ring D with opening of bond N4-C21 (5). Norfluorocurarine at interaction by hydroxylamine forms oxime of norfluorocurarine

(6),

at

its

processing

by

ethyl

alcohol

is

formed

2-oxy-2,16-dihydroanhydrooximnorfluorocurarine (7). At acidification of 7 alcohol muriatic acid

descends

a

dehydration

anhydrooximnorfluorocurarine

(8)

of

bond

yielded.

At

С2-С16 response

and

hydrochloride

norfluorocurarine

of with

phenylhydrazine in acid medium is obtained with disclosing the indol nucleus (9). Stereochemistry of norfluorocurarine and its derivatives, their absolute configuration are determined on the basis of spectroscophy and X-Ray analysis data. The basic physicochemical parameters of the modified compounds are spotted.

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9

6

3

7

N

A

15

N H

H

CH

HO N

6.

E

3 7

B N H

C

15

D

13 12

H

15'

1

H

4

21

20

16 H

17

19

C H2

16' H

18

N

2'

H

7'

N

O

N

14

2 H 15

1

N

CH2 H

CH

3

7

11

N

5

8

10

3'

2

N H

N 2

N H OH

16

N 7

H

N H

C

8

H

CH

H

C O N

N

3 E

A 7

Cl

N

3 15

N H

C N

CH2

OH

H

O

4

H

H

N H N H

CH3

N 15

N

7

3

5

H

O

20

CH3

2

NH2

21

16

N N

CH

· 249 ·

C

9

N D

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FUNGICIDAL ACTIVITY OF THE ETHANOLIC EXTRACT OF FERULA FOETIDA RESIN F.A. Mustaev*, E.R. Kurbanova, A.A. Umarov, E.Kh. Khalilova, S.F. Aripova S.Yu. Yunusov Institute of the Chemistry of Plant Substances AS RUz, Tashkent, Uzbekistan, e-mail: fein@1982 yahoo.com

A search of nontoxic fungicides for use in agriculture is an actual problem for chemists and biologists. In this connection, we have investigated the fungicidal activity of Ferula foetida resin, which possesses the diverse biological properties according to our previous

studies and the literature data. We investigated the activity of F. foetida ethanolic extract on cotton phytopathogens Xanthomonas malvacearum, Fusarium oxysporum, Verticillium dahlae, causing the

gummosis, fusarium wilt, and wilt of cotton, respectively. Fungicidal activity was determined using the method of disks by N. A. Krasil'nikov. Vitavax and Bronotak, the preparations permitted to use in cotton against the abovementioned diseases, served as standards. It was established in laboratory tests that 10% extract of F. foetida showed the highest fungicidal activity on Verticillium dahlae growth as the zone of absence of pathogen growth reached 12–15 mm. In relation to Xanthomonas malvacearum and Fusarium oxysporum and the zone of pathogen growth absence was 5–10 and 7–9 mm, respectively,

whereas in the standard options using Bronotak and Vitavax preparations - 12 mm and 15 mm respectively.

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TERPENOIDS AND FLAVONOIDS OF PLANTS OF ARTEMISIA GENUS SERIPHIDIUM (BESS.) SUBGENUS FROM FLORA OF CENTRAL ASIA R.F. Mukhamatkhanova, I.D. Sham’yanov S.Yu.Yunusov Institute of the Chemistry of Plant Substances AS RUz, fax (99871) 1206475, e-mail: [email protected] Artemisia genus Seriphidium (Bess.) Rouy subgenus plants in Central Asia are present by

71 species, that also divided for sections Seriphidium and Junceum Poljak. This subgenus in Uzbekistan is presented by 39 species, being main edible source on arid and semiarid zones of 24 million hectares area for pasture stock-breeding. Results of phytochemical studies of Artemisia genus Seriphidium (Bess.) Rouy subgenus growing on territory of Central Asia are presented in the report. Above mentioned plants are source of different structural groups of biological active terpenoids and flavonoids partly using in medical practice and national economy.

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THE COMPOSITION OF CO2-EXTRACT OF ECHINOPS RITRO Ye.M. Suleimena, S. Machmudahb, M.Yu. Ishmuratovac, M. Sasakib, S.B. Rahmadievaa, M. Gotob a

L.N. Gumilyov Eurasian National University, Astana, Kazakhstan b c

Kumamoto University, Japan

Zhezkazgan Botanic Garden, Kazakhstan [email protected]

Alkaloids [1-2], sesquiterpene acids and triterpenes [3], flavanoids [4-6], n-alkanes [7] and lipids [8] were isolated from Echinops ritro (Asteraceae) before. Crude extracts and thiophenes of E. ritro have termiticidal activity against Coptotermes formosanus [9]. The dichloromethane extract of the radix of E. ritro and thiophenes from it has antifungal activities using a broth microdilution assay against plant pathogens Colletotrichum acutatum, C. fragariae, C. gloeosporioides, Botrytis cinerea, Fusarium oxysporum, Phomopsis viticola, and P. obscurans [10]. The essential oils from the fresh inflorescences of E. ritro were analyzed by GC and GC/MS. The oil of E. ritro showed (E)-2-hexenal (21,4%), 1,8-cineole (16,3%) and pcymene (12,2%) as the major constituents [11]. In our study we investigated by GC/MS method a composition of CO2-extract of E. ritro, which was collected in Kazakhstan, Pavlodar region., near Toraigyr lake (Bayanauyl) in the beginning of August, 2007 (flowering). Supercritical Fluid Extraction (SCFE) parameters: Extraction was carried out at a pressure of 15 МPa, flow rate of CO2 - 3 ml/min and temperature of extractor - 40 ºС. The yield of extract is 1,01%. The obtained fractions were dissolved in 1 ml of ethanol, cooled overnight at -20 ºС and analyzed by GC/MS.

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GC/MS: System: Hewlett Packard GCD system. Column: an Innowax FSC (60 m x 0.25 mm id.). Temperatures: Injection port: 250 ˚C. Column: at 60 ˚C for 10 min and programmed to 220 ˚C at a rate of 4 ˚C/min, and then held isothermal for 10 min. Carrier gas: Helium, with 1mL/min. Split Ratio: 50 : 1. Electron Energy: 70 eV Mass-range: m/z 35-425. Library: Wiley GC/MS Library. It has been found, that the tetradecanoic acid (32.4%), phytone (7.3%), hexadecanoic acid methyl ester (4.5%) and diisobutyl phthalate (2,9%) were found as main components.

The authors thank the Matsumae International Foundation for financial support.

REFERENCE

1.

Savin K., Tucakov J., Lukic P., Acta Pharmaceutica Jugoslavica, 4(2), 123-8 (1974).

2.

Doepke W., Fritsch G., Pharmazie, 24(12), 782 (1969).

3.

Ulubelen A., Kurucu S., Fitoterapia, 62(3), 280 (1991).

4.

Mahadyan F., Qadsi M.B. Daneshkade-ye Darusazi, 31-4 (1977).

5.

Chevrier M., Raynaud J., Bull. des Travaux de la Societe de Pharm.de Lyon, 17(2), 72-8 (1973).

6.

Chevrier M., Fitoterapia, 47(3), 115-17 (1976).

7.

Chevrier M., Abdel G.M., Bull. des Travaux de la Societe de Pharm. de Lyon , 18(2), 58-65 (1974).

8.

Chevrier M., Abdel G.M., Raynaud J., Pharmazie, 30(6), 389-90 (1975).

9.

Tellez M.R., Kobaisy M., Osbrink W.L., et all, Phytotoxic, antifungal, antialgal, and antiinsect activity of components from selected plants of Kazakhstan and Greece, AGFD-018 (2004).

10. Fokialakis N., Cantrell C.L., et all, J. Agric.and Food Chem., 54(5), 1651-1655 (2006). 11. Papadopoulou P., Couladis M., Tzakou O., J. Ess. Oil Res., 18(3), 242-243 (2006).

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INFLUENCE OF FIVE CHINESE INSECTICIDES TO PR ENZYMES ACTIVITY OF UPLAND COTTON LEAVES A.M.Asrorova, H.A.Aisab, O.N.Veshkurovaa, A.Yilib, E.M.Sultanovaa, Sh.I.Salikhova a

Institute of Bioorganic Chemistry, Sciences Academy of Uzbekistan b

Xinjiang Technical Institute of Physics and Chemistry, CAS

The influence of five Chinese insecticides to the Pathogenesis Related (PR) enzymes activity of the leaves of one Upland Cotton (Gossypium hirsutum) cultivar was learned. The insecticide preparations influence was correlated with the activities of Chitinase and Peroxidase enzymes. Table 1 the list of insecticides which were used. №

Name

1.

Awei Dusipi

2.

Zhongbao shaman

3

Jianzhu

4.

5

Chudao

Shiniao

Components

Chemical formula

Percentage

Chlorpyrifos

C 9 H 11 Cl 3 NO 3 PS

14.8%

Abamectin

C 47 H70 O 13

0.2 %

Pyridaben

C 19 H25 CIN2 OS

7.8%

Abamectin

C 47 H70 O 13

0.2%

Acetamiprid

C 10 H11 ClN4

3%

Abamectin

C 47 H70 O 13

1%

Isocarbophos

C 11 H16 NO 4 PS

14.5%

Phoxim

C 12 H15 N 2 O3 PS

14.5%

λ-Cyhalothrin

C 23 H19 ClF3 NO 3

1%

Isoprocarb

C 11 H15 NO 2

20%

Buprofezin

C 16 H23 N 3 OS

5%

Pathogenesis related (PR) proteins are plant proteins that are induced in pathological situations. They are considered a part of the multiple defense systems of plants. For example, · 254 ·

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chitinase and β-1,3-glucanase have the ability of degrading fungal and bacterial cell walls. Peroxidases are key enzymes in lignification and hypersensitive responses in plants, which limited disease. Only recently has it been shown that sap-feeding arthropods (aphids, whiteflies, mites) induce PR proteins in plants. A number of PR proteins as polyphenoloxidases, ribonucleases, peroxidases, proteases etc. have been detected in plants. Peroxidase is considered as one of factors providing defense of cotton plant against pathogens; some isoforms of this enzyme in cotton plant have been thoroughly researched. During the 14 days of the treatment there was not observed big differences in exterior of the control and treated leaves. The amount of soluble proteins of having been treated leaves was more than in control, exception belong Shiniao insecticide which active chemical constituents are Isoprocarb (CAS 2631-40-5) and Buprofezin (CAS 69327-76-0) . In the first day samples (e.g. two days after the treatment) the soluble proteins amount increased to 25-35% in the first 4 samples, then there was a slump in their amount as in control leaves. This could be connected with vegetation period of the plant. With Shiniao treated samples the amount of soluble proteins was less than in control leaves. The peroxidase activity of proteins isolated from the cotton leaves having been treated with insecticides was lower comparing to control leaves. In control leaves there were observed linear increase from the first day till the last of the experiment. In the leaves treated with Zhongbao Shaman preparations there was an increase as in control days, however by days the enzyme activity was lower than in control. In, Jianzhu, Chudao and Shiniao samples there were increases at the last days, however for the first two days samples the enzyme activity was lower than before the treatment day. The least activity counts belonged to leaves treated with Awei Dusipi preparations. The chitinase activity of proteins isolated from the cotton plant leaves treated with insecticides was lower comparing to leaves taken as control. In control leaves there was a continual increase. In the samples treated with Awei Dusipi, Zhongbao Shaman, Jianzhu and Chudao there were identical activity changes, e.g. there were increases from the 4th day till the 7th however their activity were much lower than in control. In the Shiniao samples the chitinase activities were higher. For the first three days the chitinase activities of these samples were higher than control leaves but then there was a slump in the next two days. · 255 ·

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However after the treatment of cotton plant with different insecticide preparations, the quantity of soluble proteins increased in the samples treated with Awei Dusipi, Zhongbao Shaman, Jianzhu and Chudao products, the activities of peroxidase and chitinase enzymes were lower comparing to control. The exception was in Shiniao samples, in which the soluble protein quantity was less than in control and chitinase activity were higher during the first six days. This might cotton plant less resistant to chemical agents, some pests leading to the decrease of these PR proteins activity.

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INSECTICIDE PROPERTIES OF FRACTIONS ISOLATED FROM THE SEEDS OF MALVA SYLVESTRIS M.J.Oripovaa, E.M.Sultanovaa, Yu.I.Oshepkovaa, O.N.Veshkurovaa, Sh.T.Khodjayevb, Sh.I.Salikhov1 a

Institute of Bioorganic chemistry, Sciences Academy of Uzbekistan b Uzbek Institute for Plant Protection

Conrolling of insect pests is an important activity for agriculture in Uzbekistan. Many insect species pose serious economic threat. Example insect species include: Helicoverpa armigera, Spodoptera exigua, Agrotis segetum Glyphodes pyloalis West-W. et al. In Uzbekistan, broad-spectrum chemical pesticides have been used extensively to control insect pests. This has been at a serious cost. Chemical pesticide residues have polluted the ecosystem in Uzbekistan and have killed beneficial insects. In this connection it is very significant to explore biocide peptides, the genes of which are expected to be used in engineering of genetically modified cotton cultivars, having a high resistance to pathogens and insects. We investigated several members of the Malvaceae series indigenous to Uzbekistan. These plants will be assayed for biocide peptides that could be utilized to further increase cotton's resistance to pathogens, nematodes and insects. For isolation of cationic peptides defatted seeds were extracted with 10% acetic acid for 3 hours. Extract was neutralized and centifugated. In supernatant the pH of the media was adjusted 8.5. The solution was applied at DEAE-23SN column (2.5x20 cm, Reanal). Unbounded fraction was separated at CM-Sephadex 52 column (2.5x20 cm, Tosoh Bioscience) in the gradient of 0-1M NaCI. In the experiments carried out isolated four fractions, which were further tested for insecticide properties. The obtained fractions were lyophilized. Insecticide properties were determined with microinjections in the body of caterpillar Agrotis segetum (Den). (at the stage of 5). Protein solutions in apyrogenic sterile water (until 5 μl) were given to under epidermis layer with using syringes Hamilton. Lethal counts were done four times a day within five days. In the concentration of 25 and 50 μg more than 50% of larvae died. Among the isolated fractions the insecticidal property of the third fraction was quite higher comparing to other fractions, which will further be purified. The taken results serve for further purification of fractions and isolation of proteins or other compounds with insecticide properties. · 257 ·

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THE INFLUENCES OF SOWING DEPTH ON SEED GERMINATION OF SAUSSUREA INVOLUCRATA KAR. ET KIR. Yanrui Chena, Xiaojun Wanga, Nuerbolatia, Linke Yinb a

Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi, 830011, China b

Xinjiang Institute of Ecology and Geography, CAS, Urumqi, 830011, China

Different sowing depth has greater impact on seed germination and seedling emergence of Saussurea involucrata. In this paper, seeds of S. involucrata in the Hejing region of Xinjiang were selected as test material. Using a method of covering a potted plant in a greenhouse, the effects of different sowing depth on seed germination and seedling emergence of S. involucrata were studied. The main purpose of this study is to find the appropriate sowing depth of S. involucrata for its artificial planting. The results showed that the seed germination rate of S. involucrata was first increased and then decreased with increasing sowing depth under the depth gradient of 0, 0.5, 1.0, 1.5, 2.0, 2.5, 3.0, 3.5, 4.0 cm for its seeds in the soil. The seed germination rate of S. involucrata is highest and reaches 44% in the soil depth of 1.0cm. Its seed germination rate is followed by up to 26% in the soil depth of 1.5cm. Its seed germination rate is 12% ~17% in 2.0~3.0cm depth of soil. And its seed germination rate is less than 1% in the soil depth of 4.0cm. Above all, it shows that 1.0~1.5cm is the best depth of sowing for S. involucrata under the artificial cultivation conditions in arid areas.

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ALKYLATION OF О-CRESOL BY POLYPRENOLS U.T. Zokirovaa, N.K. Khidirovaa, А.А. Korolevab,N.M. Mamatkulovaa, А.V. Kuchinb, Kh.M. Shakhidoyatova a

S.Yu. Yunusov Institute of the Chemistry of Plant Substances. M. Ulugbek str, 77, Tashkent, 100170, Uzbekistan, fax: (99871) 120 64 75, e-mail: [email protected] b

Chemistry institute of Komi NC UD AS Russian Federation

Adjusting the important vital processes the aromatic compounds containing prenyl units, are part of biologically active objects [1-3]. In this connection doubtless interest is represented with phenolic derivatives of polyprenols. In the given message we result the data on alkylation of o-cresol with polyprenols, isolated from leaves of a cotton [4], which contained 10-12 isoprene units. At alkylation on Fridel - Crafts as the catalyst we used aluminium salt of o-cresol. Alkylation o-cresol by polyprenols С50-С60 go under the scheme: OH H CH2

C CH CH2 CH3

CH2 n-1

C CH

CH3 aluminium salt of cresol

CH2OH

0

t = 135-140 C

CH3

PPre

PPre

OH H3C

HO

PPre

H3C

PPre

PPre = polyprenyl rest

It has been shown, that at temperature 135-140оС and equimolar ratio of aluminium salt of o-cresol / polyprenols are formed mainly o-polyprenylcresols which contents is achieved 41%, thus the share p-substituted isomer makes 11%. Except for them products of polymerization of polyprenols have been obtained. The structure of the obtained substances is proved with the help of physical and chemical methods.

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REFERENCE 1.

C.Huang, Z.Zhang, Y.Li. Indian J. of Chem., 38B, 1274(1999).

2.

C.Huang, Z.Zhang, Y.Li. Synthetic Commun, 29, N8, 1383(1999).

3.

E.J. Corey, I.Wu. Laurence J. Am.Chem.Soc. 115, N20, 9327(1993).

4.

H.-Y. Shen, Z.M.A.Judeh, C.B.Ching. Tetrahedron Lett. 44, 981(2003).

5.

Patent RUz №1543 from 19.12.1994. Bulletin of Invention. №1,121(1995).

А.М. Rashkes, N.К. Khidirova, Ya.V. Rashkes, U.Z. Mirkhodjaev, U.K. Nadjimov, Kh.M. Shakhidoyatov. The method obtaining of polyprenols.

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STUDYING OF BIOLOGICAL ACTIVITY OF DITERPENOID ALKALOIDS AND THEIR DERIVATIVES FROM ACONITUM KARACOLICUM E.O. Terenteva, Z.S. Khashimova, M.N. Sultankhodjaev, Sh.S. Azimova Institute of Chemistry of Plant Substances, Mirzo-Ulugbek Str. 77, 100170 Tashkent, Republic of Uzbekistan, Tel: (0998)2622099, fax: (0998) 1206475, e-mail: [email protected] Diterpenoid

alkaloids

were

isolated

from

the

plant

Aconitum

karacolicum

(Ranunculaceae). Cytotoxic activity of one of the diterpenoid alkaloid’s synthetical derivatives on HeLa and X Ag 8.653 cells have been studied. On HeLa cells line this substance in doses from 1 to 10 μg/100 μl in a dose-dependent manner suppressed growth of cells on the average on 81 % in comparison with control (cells without substances). On X Ag 8.653 cells line of the given substance suppressed growth of cells in the same concentration on the average on 60 % in comparison with control. The received results demonstrated the high cytotoxicity of the given substance. Antioxidant activity of diterpenoid alkaloid’s synthetical derivative on mitochondrions of rat’s liver and on HeLa and X Ag 8.653 cells also has been studied. In doses of 1 and 10 μg/100μl this substance reduced malondialdehyde concentration by 35 and 68 % in comparison with control. On HeLa cells given substance in doses of 1 and 10 μg/100 μl reduced formation of malondialdehyde by 67,2 and 81,3 %, on X Ag 8.653 cells - on 50,4 and

29 % accordingly. The received results show antioxidant

properties of this substance. The results indicate the need for more investigations into the significance of the biological properties of these diterpenoid alkaloids and its derivatives.

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NEUTRAL COMPONENTS OF ALCEA NUDIFLORA OF FAMILY MALVACEAE M.J. Rakhmatovaa, N.K. Khidirovaa, T.P. Kukinab, R.Kh.Shakhidoyatova, Kh.M. Shakhidoyatova a

S.Yu. Yunusov Institute of the Chemistry of Plant Substances. M. Ulugbek str, 77, Tashkent, 100170, Uzbekistan, fax: (99871) 120 64 75, e-mail: [email protected] b

N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, SB RAS, 630090, Russia, Novosibirsk

Among deciduous plants Malvaceae differ with the high contents of polyprenols (PP), being chemotoxanomic markers [1–3]. Neutral triterpenoids and bioactive polyprenols are not investigated well [4]. We had been carried out the analysis of plant extracts Alcea nudiflora and some fractions on the contents of polyprenols by method HPTLC. Componential structure and the contents of polyprenols of enriched fractions had been determined. Thus it has been established structure of polyprenols in leaves of the plants. It has been shown, that they contained 8-14 isoprene units, their contents were 0,9; 1,9; 3,0; 39,0; 44,2; 10,3; 0,6 accordingly. Among them dodeca- and undecaprenols dominated. For the first time in plants of Althaea the minor components were of polyprenols including 8, 9 and 14 isoprene units. In a neutral part of extraction sums in addition to polyprenols 28 components were determined by a method of chromato-mass-spectrometry: aliphatic hydrocarbons, triterpens, i.e. hexahydrofarnesylacetone, fitol, scvalene, - and -tocoferols, cholesterol, cholestanol, stigmasterine, β-sitosterine, fucosterin, - and -amirines, etc. Twenty four from these components not been founded in these plant before. REFERENCE 1. 2. 3. 4.

N.K. Khidirova, Kh.M. Shakhidoyatov, Khim. Prirod. Soedin. [in Russian], 87(2002) N.K. Khidirova, A.M. Rashkes, Ya.V. Rashkes, Kh.M. Shakhidoyatov, Khim. Prirod. Soedin. [in Russian], 280(1991) E.V. Van, R.Kh. Shakhidoyatov N.K. Khidirova, N.I. Mukarramov, Kh.M. Shakhidoyatov, Khim. Prirod. Soedin. [in Russian], 653(2009). R. L. Rowland, P. N. Latimer, J. A. Giles, J. Am. Chem. Soc. 78, 4680(1956) · 262 ·

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NEUTRAL COMPOUNDS OF GRASSY PLANT HIBISCUS L. LEAVES S.E. Kiyamova, Kh.U. Khodjaniyazov, N.K. Khidyrova, Kh.M. Shakhidoyatov S.Yu. Yunusov Institute of the Chemistry of Plant Substances AS RUz, Tashkent, Uzbekistan, fax: (99871) 120 64 75, e-mail: [email protected], [email protected] It is known that plant polyprenols have wide perspectives for the creation various types of medicaments (antiulcer, immunotrophic, antiviral, etc.) activities [1, 2]. Therefore revealing of sources of polyprenols and others isoprenoids from local plant raw material of Uzbekistan in order to produce production of new domestic preparations of special interest. In the Republic of Uzbekistan six kinds of plants from Malvaceae family grow: Gossypium L., Althaea L., Alcea L., Malva L., Hibiscus L, Abutilon M. Hibiscus L. is the grassy plant, widespread in the valley and delta of Amu-Darya, on pools. It is considered as an oil-bearing, fibrous and nutritional plant. In folk medicine its leaf tincture is used as an expectorant. Earlier we have reported about the components of aerial part of Abutilon M. [3]. In the current report we give research results of chemical contents of extracted substances from the leaves of the endemic plant Hibiscus L. Extracting air dried leaves of the plant with 96 % ethyl alcohol and the further with alkaline hydrolysis the sum of neutral substances have been obtained, structures has been studied by chromoto-mass-spectrometry method and by means of high performance thinlayer chromatography (HPTLC). The results show that the main components are alcohols, hydrocarbons, sito-, stigmasterols, polyprenyl alcohols, tocopherol, etc. Structure and content of polyprenyl alcohols of the leaves of Hibiscus L. are determined by HPTLC. It was revealed that like in other sorts of plants from Malvaceae family, the homological structure of polyprenols consists of 9–13 isoprene units. Among theim undecaprenols and dodecaprenols dominated. REFERENCE 1. N.K. Khidyrova, Kh.M. Shakhidoyatov, Khim.Pripod. Soedin., [in Russian] 89 (2002) 2. E. Swiezewska, W. Sasak, T. Mankowski, et al., Acta Biochim. Polon., 41, 221(1994) 3. S.E. Kiyamova, N.К. Khidyrova, T.P. Kukina, Kh.M. Shakhidoyatov, Khim.Pripod. Soedin., [in Russian] (2011 in press) · 263 ·

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OBTAINING DRY EXTRACTS FROM ROOTS AND RHIZOMES OF RHODIOLA LITVINOVII F.A. Melikuziev, B.M. Makhmudova, S.Z. Nishanbaev, G.B. Sotimov S.Yu. Yunusov Institute of the Chemistry of Plant Substances Academy of Sciences 100170, Tashkent, Uzbekistan, fax (99871) 120 64 75, e-mail: [email protected] Rhodiola plants belongs to Crassulaceae family. High biological efficiency of Rhodiola rosea preparations attracted a lot of attention to study other types of Rhodiola. Coming there purpose of the study working out optimally condition of extraction of roots and rhizomes of Rhodiola litvinovii was started. The plants was collected in phase of flowering in West Tyan-Shan (in July 2010). It is known that separation of biologically active material from plants depends on the degree of the pounding, selection of solvent as extragent. So, for obtaining of the extract material the roots and rhizomes of Rh. Litvinovii Boriss. were dried under room temperature and pounded on particles 3–5 mm and 5–8 mm, extractive solvent was ethanol under concentration (20%, 40%, 60%, 80%, 90%). After that the extracts were concentrated, dried and different extract sums were defined by the gravimetric method (tabl.1). Table 1.Yield of extractive substances dependent from concentration of ethanol and parities size, % Degree of pounding, mm

3–5 mm

5–8 mm

Concentration of ethanol,

Output of extractive material, in % to mass

%

cheese

20

33,4

40

34,6

60

42,8

80

31,4

90

30,1

20

32,5

40

33,3

60

42,6

80

30,3

90

29,8

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Data of Tabl. 1 show, that irrespective of from the particies size the highest the yield of the extractive substances was at the concentration of the ethanol 60%. Further the rise of concentration of ethanol is reduced the yield of extracts. Composition of the dry remainder tannins were studied by means of permangametric method, solidrosid - by spectrophotometric method, ascorbic acid and essential oils are determined by titration. It was determined that roots and rhizomes contain 0,7–0,9% phenol glycoside - radioloside (solidrosid); 18-20% tannins; 0,3% essential oils, as well as vitamins С and PP. Works on the study the composition of extractive material, as well as creation of new preparation on their base continued.

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PHENOLIC COMPOUNDS OF ROOTS AND RHIZOMES OF RHODIOLA LITVINOVII F.A. Melikuziev, S.Z. Nishanbaev, Kh.M. Bobakulov, N.D. Abdullaev S.Yu. Yunusov Institute of the Chemistry of Plant Substances Academy of Sciences 100170, Tashkent, Uzbekistan, fax: (99871) 120 64 75, e-mail: [email protected] The genus of Rhodiola is characterized by high content of active substances [1]. So, gold root (Rhodiola rosea) is medical plant reminding on character action of the ginseng group preparations [2]. High efficiency of preparations Rhodiola rosea has lead to research other species of Rhodiola. The object of current researches was the plant Rhodiola Litvinovii Boriss. (Crassulaceae). Roots and rhizomes of Rh. Litvinovii collected in phase of flowering in the Western Tyan– Shan (Pscem ridge, Bostanlyc district of Tashkent region, July, 2010) had been investigated. The roots and rhizomes of Rh. Litvinovii (2 kg) were subjected to exhaustive extraction by 40% ethanol. The total extract evaporated in vacuum. The condensed heavy-bodied residue diluted by water and subsequently treated by petroleum ether, chloroform, ethyl acetate and n-butanol. The condensed ethyl acetate extract was mixed with silicagel L 40/100 and obtained powder was subjected to chromatography on silicagel, eluted by chloroform and mixture of chloroform-methanol in different ratio. Separation of substances controlled by TLC analysis (Silufol UV 254) in system chloroform–methanol 4:1 and also with chloroform–methanol– water 26:14:3. In chromatographic separation of ethyl acetate fractions compounds 1 and 2 had been isolated. The obtained NMR spectral data and their comparison with literature [2, 3] have allowed to make the conclusion, that the isolated substance (1) is n-tyrosol-(n-oxyphenyl-ethanol), and compound (2) is salidroside – (n-oxyphenyl--(--D-glycopyranosyl)-ethanol). Both compound 1 and compound 2 from Rh. Litvinovii are isolated for the first time.

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REFERENCES 1.

V.A. Kurkin, G.G. Zapesochnaya, Chemical constituents and pharmacological properties of the plants of Rhodoila genus // Chem. pharm. J., 20 (10), 1231–1244, (1986).

2.

S.A. Saratikov, E.A. Krasnov «Rhodiola rosea–an important medicinal plant (golden root) », Tomsk, 252, (1987).

3.

S.A. Patov, I.G. Zaxozhiy, V.V. Pugenov, A.V. Kuchin, M.I. Kodess, Chemistry and Computational Simulation. Butlerov Communications, 7, 85-88, (2002)

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LIPIDS OF SOLENANTHUS TURKESTANICA FRUITS N.K. Yuldasheva, N.T. Ul’chenko, A.I. Glushenkova, A.M. Nigmatullaev S.Yu. Yunusov Institute of the Chemistry of Plant Substances AS RUz, Tashkent, Uzbekistan, Fax: (99871) 120 64 75, e-mail: [email protected] Uzbek species of Solenanthus (fam. Boraginaceae) includes 6 geni and it is characterized by large set of fatty acids. The fruits of Solenanthus turkestanica had been studied. They were collected in Surkhandarya region. In order to extract free lipids, fruits were pounded and extracted by benzine (tb 72–85C) three times for 5 hours every time at the room temperature. Then from these material polar lipids were extracted by chloroform-methanol (2:1 v/v). Yield of free lipids is 9.47 %, polar lipids – 2.06 % from mass of fruits. Using column chromatography on silica gel polar lipids were separated on neutral lipids (NL), gluco- (GL) and phospholipids (PhL). Free lipids were eluated by chloroform, GL - by acetone and PhL – methanol. Yields were 0.86, 0.81 and 0.39 % accordingly. Besides polar lipids had 521.6 mg % of chlorophyllic pigments. Using TLC on silica gel in the solvents system hexan – diethyl ether 7:3, we determinated the composition of NL: TAG (main component), hydrocarbons, free fatty acids, sterols and trackly of quantity of diacyl– and monoacylglycerols, carotinoides and tocopherols. In GL sterol glycosides (main component) ethers of sterol glycosides, digalactosyl – and monogalactosyldiglycerides were determinated. Double ATLC of phospholipids on silica gel showed that their composition includes phosphatidilethanolamins, phosphatidilcholins, phosphatidilinosites and phosphatidic acids. NL, GL and PhL were hydrolyzed and then fatty acids were isolated, which were methylated by diasomethan and analysed using GLC on Agilent Technologies 6890 N with flaming ionisationly detector, and capillary column, length 30 m with unpolar phase HP-5, temperature from 60 to 250. Gas was helium 30 ml/min. It was established that saturated palmitic acid was dominated in all classes, but from unsaturated fatty acids the main acids were 18:1, 18:2 and 18:3. Octadecatrienolic acids in NL were 13.01 %, in GL and PhL on 12 % in every class. NL contented the most high quantity unsaturated fatty acids. The ratio unsaturated fatty acids to saturated ones was for NL 3:1, for Gl – 2:1, PhL – 1:1.

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POLYISOPRENOIDS OF RHUS CORIARIA N.M. Mamatkulova, F.A. Melikuziev, N.I. Mukarramov, N.K. Khidirova, S.Z. Nishanbaev, Kh.M. Shakhidoyatov S.Yu. Yunusov Institute of the Chemistry of Plant Substances. M. Ulugbek str, 77, Tashkent, 100170, Uzbekistan, e-mail: [email protected] Rhus coriaria (tannic sumakh) is a many year bush, belonging family Anacardiaceae. It is distributed in Central Asia (Southern Pamir-Alay, Kopet Dagh), Caucasus, in Crimea, Iran and Uzbekistan (the Surkhan-Darya, Tashkent areas). Leaves of sumakh render knitting, blood stopping, anti-inflammatory, antiseptic and diuretic action [1]. In folk medicine tincture from fresh leaves of sumakh in quality thirst satisfying and a febrifuge at a fever, a malaria, a scarlet fever, at paralyses, and also at diseases of a throat and an oral cavity as rinsings is used. It is known, that leaves of sumakh tannic are rich for tannins [2, 3], phenol carbonic acids, their derivatives, flavonoids [4] and fatty acids [5]. In the given work we investigated sum of polyisoprenoids of leaves of sumakh tannic, collected in the period of budding in the Tashkent oasis. For isolation of the neutral substances sum the air - dry crushed raw material extracted three times gasoline, after distillation of solvent on rotor evaporator have received 206,3 g (8,26 % from air - dry weight) sum of extracted substances. Further alkaline hydrolysis carried out, none hydrolyzed part have studied with application high performance thin layer chromatography (HPTLC) compare with standard samples polyprenols of a cotton. Results of the analysis have shown, that in none hydrolyzed fractions of the extract contains polyprenols with 10–13 isoprene units. The contents of the polyprenols sum was 20,9 %. It is necessary to note, that the petrol extract of sumakh tannic can be used as raw material for obtaining of polyprenols containing preparations. REFERENCE 1.

Flora of Uzbekistan, AS UzSSR Press, Tashkent 1959, Vol.4, P.129. · 269 ·

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2.

А.К.

International

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Кarimdjanov,

Sh.Yu.

on The

Chemistry

Islambekov,

S.M.

of Natural

Compounds

Mavlyanov,

A.I.

Ismailov,

Khim.Prirod.Soedin, [in Russian] pp. 386–387 (1986). 3.

S.M. Mavlyanov, Sh.Yu. Islambekov, A.I. Ismailov, D.N. Dalimov, N.G. Abdullajanova, Khim.Prirod.Soedin, [in Russian] pp. 3–22 (2001).

4.

I.Sh. Bushashvili, N.F. Komissarenko, D.G. Kolesnilov, Khim.Prirod.Soedin, [in Russian] P. 627 (1970).

5.

M. Dogan, A. Akgul, Khim.Prirod.Soedin, [in Russian] pp. 596–597 (2005).

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RESEARCH OF CHRONIC TOXICITY OF DIHYDROATIZINE ALKALOID M.S. Kodirova, F.M. Tursunkhodjaeva, Z. Rejepov, F.N. Dzhakhangirov Institute of chemistry of plant substances named after acad. S.Y.Yunusov AS RUz, Tashkent, fax (99871 1206475, е-mail: [email protected] Pharmacological research has shown, that dihydroatizine hydrochloride possesses by high antiarrythmic activity on arrythmia induced by calcium chloride, strophanthin "K" and coronary artery occlusion. The purpose of research was studying its chronic toxicity. Researches were spent on rats in weight 200-240g and on rabbits in weight of 3,5-4 kg. To rats a preparation was introduced orally in doses 10 and 50 mg/kg, to rabbits - intravenously in dozes 1, 0,1 and 1,0 mg/kg within 30 days. In 15 days and after finishing the experiment (in 30 days), animals were killed and hematological biochemical and histological researches made. Results of peripheral blood researches have shown, that in 15 days after preparation infusion essential changes not marked in comparison with control group of animals. In the second period of research (in 30 days) beginning, from a doze of 50 mg/kg the insignificant increase of leukocytes and decrease of hemoglobin is revealed. The quantity of erythrocytes did not change essentially. Biochemical researches have shown, that dihydroatizine applied for a long time in dozes of 1 and 10 mg/kg does not render essential influence on biochemical parameters of blood rats and rabbits (0,1 and 1,0 mg/kg). At injection of the preparation to rats in a doze of 50 mg/kg the authentic increase in ALT maintenance and decrease in inorganic phosphorus in blood serum that is probably connected to infringement of exchange processes in intimate and hepatic tissues is noted. Macroscopical and histological researches of internal bodies and brain of experimental rats and rabbits has shown that the preparation in the specified dozes does not cause structural changes. Thus, it has shown, that dihydroatizine at long application in the specified dozes does not render negative influence on an organism of experimental animals. Some changes from hematological and biochemical parameters of blood at a doze of 50 mg/kg (above a 100 times from therapeutic doze) are reversible. · 271 ·

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FLAVONOIDS FROM AERIAL PARTS OF SCUTELLARIA GUTATA Z. O. Tashmatov, K. A. Eshbakova, J. I. Tursunov S.Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences, 100170, Tashkent, Republic of Uzbekistan. e-mail: [email protected] We have investigated Scutellaria gutata (Lamiaceae) collected in the Surkhandaryo region of Uzbekistan, in the flowering phase. Earlier from Scutellaria gutata by the column chromatography of an alcoholic extract of ethylacetate fraction on silica gel, we have isolated

three

flavonoids:

chrysin

(5,7-dihydroxyflavone),

apigenin

(5,7,4´-

trihydroxyflavone) and hispidulin (5,7, 4´-trihydroxy-6-methoxyflavone). Continuing our investigated with ethylacetate fraction of Scutellaria gutata, we have isolated again three flavonoids with composition С16Н12О5 , mp 215-217C. (1), С16Н12О5, mp 196-197C (2), С15Н10О6 , mp › 340 (3). Structures of isolated compounds have been established on the basis of their physical and chemical properties and the analysis of their spectral data IR , UV, as well as immediately comparison with reliable recovery. The isolated compounds have been identified as oroxylin (5,7-dihydroxy-6-methoxyflavone) (1), vogonin (5,7-dihydroxy-8methoxyflavone) (2) and scutellarin (5,6,7,4'-tetrahydroxyflavone) (3). These compounds were isolated from Scutellaria gutata for the first time.

HO

OCH3

O

HO

O

CH3O OH

O

OH

1

O

2 HO

O

HO OH

O

3 · 272 ·

OH

9th

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Chemistry

of Natural

Compounds

THE COMPLEXES OF GLYCYRRHIZIN ACID WITH THE MEDICINAL MATERIALS NITROXOLIN, ALLAPININ, LIDOKAIN А.M. Khvana, T.A. Azizovb, R.K. Karimova a

S. Yu. Yunusov Institute of Chemistry of Plant Substances, Academy of Sciences Republic of Uzbekistan, 100170, Uzbekistan, Tashkent

b

Institute of General and Inorganic Chemistry. Academy of Sciences Republic of Uzbekistan, 100170, Uzbekistan, Tashkent It is known that solubility in water solution and biological activity of a number of

medicinal materials are greatly increased in the presence of the glycyrrhizin acid (GA). This is explained by formation of the clatrat complexes, stabilized by hydrogen interactions. In the given work the formation of the GA – nitroxolin, GA - allapinin, GA - lidokain complexes by means of ionic bonds was researched. The formation of the ionic linkages between glycyrrhizin acid and investigated medicinal substances was studied by potentiometer method. This reaction is reflected on the shifts of potentiometer titration curves, which exists in the broad interval of neutral pH values, with the increasing of the medicinal compound content in solution. The fact of the formation of chemical products is acknowledged by the obtained thermo analysis data. It has been shown that the investigated medicinal substances are more thermo stable in complexes with the glycyrrhizin acid. All investigated complexes are water-soluble. The suggested method allows to vary the composition of the complexes of medicinal compound with the glycyrrhizin acid.

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INFLUENCE OF HYDROTHERMAL PROCESSING ON THE QUALITY OF GLUTEN COMPLEX OF FLOUR N. V. Korablyova, T. D. Kasimova Institute of the chemistry of plant substances Academy of science of Uzbekistan Tashkent, fax (99871) 120 64 75; e-mail: [email protected] Influence on wheat gluten quality by hydrothermal processing based on conclusions of scientists that the heating of wheat up to 45–50С strengthens weak gluten to normal, reduces quantity of water-soluble proteins, raises quantity disulfide bonds in protein complex of flour. Wheat is humidified more strongly at the rise in temperature, especially grain with low initial humidity. At cold hydrothermal processing the moisture even in an hour does not go more deeply subaleyron layer, and in 16 hours there is a difference in humidifying endosperm and membranes. Therefore, at certain parameters of hydrothermal processing it is possible to provide the directed change of gluten properties. Our experiments were carried out using various parameters of hydrothermal processing of wheat. Processes of change gluten quality have occurred in the first 2 hour humidifying at heating of grain to temperature 60–65С during 8 minutes and have made 100 units. Gluten has become stronger up to 95 units of index deformation of gluten during 4-8 hour humidifying of grains. The further humidifying grains after 10 hours has led to a relaxation of gluten (Fig1.).

Fig. 1. Changes of gluten quality in different temperature, hydrothermal parameters and duration of humidifying grains with weakened gluten. Thus, at application of hydrothermal processing in grain there are certain changes of a gluten-proteins complex as a result of which elasticity of gluten are raises. Application of hydrothermal processing of wheat with temperature of its heating up to 600С is the most productive. · 274 ·

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EXTRACTION OF FLAVONOIDS FROM ROOTS OF AMMOTAMNUS LEHMANNII R.M. Khalilov, M.A. Mamatkhanova, L.D. Kotenko, A.U. Mamatkhanov S.Y. Yunusov Institute of the Chemistry of Plant Substances, 100170, Tashkent, Mirzo Ulugbek, 77, e-mail: [email protected] In the Institute of the Chemistry of Plant Substances on the base of flavonoids from Ammotamnus lehmannii researches for develop of new medical preparation for treatments of diseases of liver are continued. In order to undertake the efficient extraction parameters, influencing upon yield of flavonoids from roots of Ammotamnus lehmanni such as selection solvent and crushed of raw materials were studied. Results of investigations have shown that the optimal solvents for extraction of raw material with a high yield of flavonoids are methanol and ethanol with concentration not less than 90%. For extraction of the sum flavonoids are recommends used crushed raw material with sizes of particles 2–6 mm. For choice of the optimal methods of extraction of flavonids from roots of Ammotamnus lehmanni such methods as matheration, matheration with mix, extraction by Soxlet method and battery way of extraction were considered. As a result it was revealed that when undertaking the extraction by matheration method with mix grows shorter time, necessities for extraction of raw materials, however, hydromodul of process increases in 2 times nearly. But this in turn brings for increase the consumption of solvent (ethyl alcohol). At extraction of raw materials by battery way and Soxlet method hydromodul and time of process of extractions grew shorter in 3-4 times in contrast with extraction by matheration method. The Results have also shown that yield of flavonoids greatly does not depend from chosen way of extraction. Considering consumption of used solvent and time, necessities for extraction, are offered battery way and extraction by Soxlet method.

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Compounds

INVESTIGATION OF PROCESS OF EXTRACTION ECDYSTEROIDS SUM FROM AERIAL PART OF SILENE BRAHUICA M.A.Mamatkhanova, M.R. Yakubova, R.M. Khalilov, A.U.Mamatkhanov S.Y.Yunusov Institute of the Chemistry of Plant Substances, 100170, Tashkent, Mirzo Ulugbek, 77. [email protected] Ecdysteroids have a great importance for maintenance of capacity to work of the organism that necessary especially athlets. These biological active substances show high anabolic activity. Anabolic action of ecdysteroids presents the big practical interest. In the Institute of the Chemistry of Plant Substances the technology of the substances of ecdysteroids sum from aerial part of Silene brahuica was developed. The study of the process of extraction is connected to labour-consuming and long experiment. Optimization of the experimental studies at all stages of the technological process enables to enlarge efficiency of the scientific studies. For increasing of efficiency of optimization and forecasting of the process of extraction in static condition the method of the mathematical planning of experiment on Box-Uilson was used. On the basis of the aprioristic information (in this case results of one-factorial experiments) and reference’s data have chosen factors, to the greatest degree, influencing on process extraction: duration of extraction, degree of crushing of raw material, temperature of the extraction, concentration of the solvent. It was established that main influence upon at the process of extraction of ecdysteroids from aerial part of Silene brahuica render such factors as duration of extractions and concentration of the alcohol in the solvent. Optimization of the process of extraction has brought to increase of output of the sum of ecdysteroids for 8%. In order to find a rational method of extraction of ecdysteroids sum from raw material the kinetics of extraction was investigated. It was established, that equilibrium concentration at the first contact of phases achieved in 6 hour. Phase balance at the second and third contacts is achieved in 5 hour, at the fourth and fifth - in 3 hour and the sixth - in 2 hour. · 276 ·

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of Natural

Compounds

THE QUANTUM-CHEMICAL ANALYSIS OF ANTIRADICAL ACTION OF GOSSYPOL AND ITS DERIVATIVES U.G. Gayibova, B. A. Salakhutdinova, V.P. Bruskovb a b

Acad. A.S. Sadikov Institute of Bioorganic Chemistry, Tashkent, Uzbekistan

S. Yu. Yunusov Institute of the Chemistry of Plant Substances, Tashkent, Uzbekistan Semiempirical quantum-chemical method PM6 by software package MOPAC2009

studied the interaction of gossypol and some of its mono-and di-derivatives with the hydroxyl radical (OH), as one of the most reactive free radicals, rendering a damaging effect on DNA, actively interacting with fragments of unsaturated fatty acids phospholipids of cell membranes. The following derivatives: monoaminogossypol, monoanilinogossypol, semibatriden, semiragosin, diaminogossypol, dianilinogossypol, batriden, ragosin were calculated. For quantitative evaluation of the antiradical action of gossypol and its derivatives is taken advantage of energy E in the transition of moving protons from their various groups to the hydroxyl radical. Proton transfer reaction always occurs with decreasing energy of the system, i.e. it is energetically favorable. Gossypol aldehyde group (E = 84.4 kcal/mol for the doublet state and E = 112.4 kcal/mol for the biradical) exhibits maximum activity. The correlation coefficient calculated parameters with experimental data from the reaction of DPPH EC50 with to the aldehyde group is 0.71.

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of Natural

Compounds

STUDY OF THE IMMUNO-STIMULATING ACTION OF PHYTOECDYSTEROIDS FROM SILENE VIRIDIFLORA I.D. Bobaeva, M.T. Alimovab, S.T. Kosnazarovc, Z.M. Putievaa, N.S. Ramazanova a

Institute of the Chemistry of Plant Substances АS RUz, Tashkent. b

c

Institute of Immunology АS Ruz, Tashkent.

Institution of Complex Natural Science Karakalpak branch АS RUz, Nukus.

It is known, that immune system is playing a big role in many diseases pathogenesis. Various stressful situations in a person daily life also make infringements in the immune system. Search and creation of new immunomodulate substances and biologically active food additives is actual. On our vision, phytoecdysteroids are perspective substances for this. Plant S. viridiflora was introduced to grow on grey oasis soils by spent botanist of the Institute of Chemistry of Plant Substances named after acad. S.Yu. Yunusov AS RUz, lets aerial part contains enough considerable ecdysteroids quantities in a flowering phase. The influence of ecdysteroids sum, isolated from methanol extract with chloroform methanol mixture (4:1) on immune system had been investigated. Experiments were spend on white mice of 20–22 g weight immunized by 5106 sheep erythrocyts in 0,5 ml of physiological solution i.p . Results shown, that in spleens of control group mice contained 12 400  979,79 APC on a spleen. At recalculation on 1 million nuclei-containing spleen cells number of АPC was 168  4,81. The investigated preparation from Silene viridiflora in all studied doses reliably (Р