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Schiff bases of some 2-phenyl quinazoline-4(3)H-ones. Eur. J. Med. Chem., 45, 5474-5479. 22. Jarrahpour, A., Khalili, D., De. Clercq, E.et al. (2007). Synthesis ...
International Journal of Chemical and Natural Sciences Vol. 2, No. 5 (2014): 157-163 Research Article Open Access

ISSN: 2347-6672

Synthesis, characterization and biological activities of turmeric curcumin schiff base complex Jayandran. M1, Muhamed haneefa. M1* and Balasubramanian. V2 1 2

Mahendra Engineering College, Faculty of Chemistry, Namakkal, India. AMET University, Dean & HOD, Faculty of Chemistry, Chennai, India.

* Corresponding author: Muhamed haneefa. M; email: [email protected]

Received: 16 September 2014

Accepted: 01 October 2014

Online: 10 October 2014

ABSTRACT Schiff bases are an important class of compounds in medicinal and biological fields. However, various studies have shown that schiff bases derived from bioactive ingredients presence in medicinal plants are more effective in biological and medicinal activities than in its pure form. In this paper we have extracted curcumin from turmeric and the resultant curcumin was used to prepare the schiff base complexes by the reaction of curcumin with amino compounds.The curcumin and its schiff base complex were characterized by UV- visible, IR spectroscopy, elemental analytical techniques and biological activities are investigated.

Keywords: Curcumin, Curcuma longa L, Curcuminaniline, Solvent extraction, Soxhlet method INTRODUCTION Turmeric is a significant medicinal spice that comes from the root Curcuma longa L. Its bright yellow pigment is used as a food coloring agent. Tumeric has been used for over 2500 years in India as a spice a food preservative and a dye. After a long period the medicinal properties of this spice have been found out [1-8]. The turmeric rhizome contains a variety of pigments among which curcumin is a major pigment. The curcuminoids are polyphenols and are responsible for the yellow color of turmeric and which has been shown to have a wide range of therapeutic effects. Curcumin incorporates several functional groups. The aromatic ring systems, which are phenols, are connected by two α,β-unsaturated carbonyl groups. The diketones form stable enols and are readily deprotonated to form enolates; the α,β-unsaturated carbonyl group is a good Michael acceptor and undergoes nucleophilic addition. The structure was first identified in 1910 by J. Miłobędzka, Stanisław Kostanecki and Wiktor Lampe.Curcumin is a liposoluble compound and can be easily dissolved into organic solvent such as methanol, ethanol, and acetone [10-11]. Schiff bases derived from an amino and carbonyl compound are an important class of ligands which http://ijcns.aizeonpublishers.net/content/2014/5/ijcns157-163.pdf

contains azomethine nitrogen, i.e., C=N linkage [12-13]. Schiff bases have wide applications in food industry, dye industry, analytical industry, catalysis, fungicidal, agrochemical and biological activities [14]. Several azomethines were reported to possess remarkable antibacterial [15-16], antifungal [17-18], antitumor [19-20], antiviral [21-22], anti-HIV [23], anti proliferative [24], herbicidal [25] and diuretic activities [26]. In general the most common method for preparing schiff bases is the reacion of aldehydes and ketones with primary amines. The reaction is generally carried out by refluxing the carbonyl compounds and amines in organic solvents by separating the water as formed with an azeotroping agent or by anhydrous Na2SO4 and MgSO4 [27-32]. Nowadays, the research field dealing with schiff base coordination chemistry has expanded enormously. The importance of schiff base complexes for bioinorganic chemistry, biomedical applications, supramolecular chemisty, catalysis and material sciences, marine applications, separation and encapsulation processes and formation of compounds with unusual properties and structures has been well recognized and reviewed [33-36]. A considerable number of schiff base complexes have potential biological interest, being used 157

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as more or less successful models of biological compounds. Not only have they played a seminal role in the development of modern coordination chemistry, but also they can also be found at key points in the development of inorganic biochemistry, catalysis and optical materials [37-38]. In recent years natural medicinal plants are used very much in the various fields of chemistry to enhance the biological and medicinal activities of the material. Based upon this we were focused on the curcumin due to its significant medicinal purposes to prepare bioactive schiff base complexes. Recently, we reported the synthesis of curcumin from selected commercial turmeric plants to find out the curcumin rich turmeric variety [39]. In continuation with our research work in the present protocol we used the curcumin rich turmeric to synthesize curcumin for better result followed by schiff base ligands effectively. Curcumin have been extracted first from turmeric by using soxhlet extraction technique with 95% ethanol as a solvent then the synthesized curcumin was reacted with aniline under certain conditions to prepare bioactive schiff base curcuminaniline. The quantification of curcumin in turmeric is normally based on spectrophotometric measurement. We found that the synthesized curcumin and curcuminaniline were shown better yield and significant biological activities.

MATERIALS AND METHODS The experiment is carried out by the method of soxhlet solvent extraction technique to extract the curcumin from turmeric. The turmeric sample with rich curcmin (BSR-01) has been collected from Agricultural College and Research Institute, Madurai. The purification was carried out by the boiling process of this turmeric with water and finally dried and powdered. The solvent used for extraction process 95% ethanol and the main chemical aniline were purchased from E.Merck (India) O

Ltd. Pure curcumin powder was obtained from HPLC, India to prepare standard solution. All reagents were of analytical grade and used as received. Synthesis of curcumin from turmeric The main component of turmeric, curcumin is quantitatively extracted from turmeric in soxhlet apparatus by using 95% ethanol as a solvent and the curcumin content was estimated as per the method of Manjunath et al. [40]. The process is described as follows briefly. 5.0 g of turmeric dried powder weighed and taken in soxhlet apparatus with 250 ml of ethanol. The extraction process carried out for 2 1/2 hrs and the final curcumin extract absorbance was measured at 425 nm against alcohol blank. Using the absorbance value the curcumin percentage was calculated. The above ethanolic residual extract was evaporated and dried then recrystalized by 95% ethanol. The standard curcumin was also processed as the same above and this standard solution (containing 0.0025g/1ml) was read at 425 nm against alcohol blank in spectrophotometer and the curcumin content obtained by this method is determined and expressed as percent. Synthesis of curcumin schiff base complex Double distilled water has been used throughout the synthesis process. The synthesized pure curcumin (10 mmol) was dissolved in ethanol and stirred well at room temperature. Then aniline (10 mmol) solution was added to the prepared curcumin solution. The obtained orange coloured mixture was stirred and refluxed at 50ο C for 6 hrs in mild acidic condition. After cooling the resulting orange fine precipitate of curcuminaniline schiff base was filtered and washed well with double distilled water repeatedly to remove any unreacted chemicals then dried in vacuum oven at 100ο C for 1 hr. The obtained orange powdered curcuminaniline was kept in a desiccator over silica gel for further analyses. The synthesis process was followed according to the scheme presented in figure 1.

O

H2N

500C

+ HO O CH3

-H2O

OH

O H3C

Curcumin (C21H20O6) O

N

HO O CH3

O

OH

H3C

Curcuminaniline (C27H25O5N) Fig 1. Representation of Schiff base formation

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Characterization All samples were stored in a desiccator containing silica gel for atleast 48 hr at room temperature to ensure minimal moisture content before spectroscopic analysis. The UV-Visible absorption spectra of the curcumin and its schiff base complex were measured on a Shimadzu UV-Vis V-530A spectrophotometer in the range of 300 to 600 nm. Elemental analyses were carried out with ElementarVario EL III series used to collect the micro analytical data (C, H and N) and compared with the calculated theoretical values. The unmodified and chemically modified curcumin and schiff base complex were examined for FT-IR spectra analysis and recorded on a jasco FT-IR/4100 spectrophotometer with 4cm-1 resolution in the range of 4000 to 400 cm-1. Biological assay The antibacterial and antifungal activity of the synthesized Curcumin and Curcuminaniline were tested against two gram positive bacteria (Staphylococcus aureus and Bacillus subtilis), two gram negative bacteria (Escherichia coli and Staphylococcus bacillus) and four fungal species (Candida albicans, Curvularia lunata, Aspergillus niger and Trichophyton simii). A comparative study of the growth inhibition zone values for curcumin and its schiff base were evolved. Antibacterial activity test The disc diffusion method (Bauer et al., 1966) was used to screen the antimicrobial activity [41]. Stock cultures were maintained at 4oC on slopes of nutrient agar. Active cultures of experiment were prepared by transferring a loopful of cells from the stock cultures to test tube of Muller-Hinton broth (MHB) for bacteria that were incubated without agitation for 24 hrs at 37oC and 25oC respectively. The cultures were diluted with fresh Muller-Hinton broth to achieve optical densities corresponding to 2.0×106 colony forming units (CFU/ml) for bacteria. The Muller Hinton Agar (MHA) plates were prepared by pouring 15 ml of molten media into sterile petriplates. The plates were allowed to solidify for 5 minutes and 0.1% inoculum

suspension was swabbed uniformly and allowed to dry for 5 minutes. The concentration of sample at 40 mg/disc was loaded on 6 mm sterile disc. The loaded disc was placed on the surface of medium and the extract was allowed to diffuse for 5 minutes and the plates were kept for incubation at 37oC for 24 hrs. At the end of incubation, inhibition zones formed around the disc were measured with transparent ruler in millimeter. Antifungal activity test The fungal strains were inoculated separately in Sabouraud’s dextrose broth for 6 h and the suspensions were checked to provide approximately 10 5 CFU/ml. The agar well diffusion method (Perez, 1993) was modified. Sabouraud’s dextrose agar (SDA) was used for fungal cultures. The culture medium was inoculated with the fungal strains separately suspended in Sabourauds dextrose broth. A total of 8 mm diameter wells were punched into the agar and filled with the sample and solvent blanks (hydro alcohol, and hexane). Standard antibiotic (Fluconazole, concentration 1 mg/ml) was used as positive control and fungal plates were incubated at 37oC for 72 h. The diameters of zone of inhibition observed were measured.

RESULTS AND DISCUSSION UV-Vis spectra studies

Curcumin was quantitatively extracted by refluxing the material in alcohol and was estimated spectrophotometrically. The UV-Vis spectra of curcumin and curcuminaniline are given in figure 2(ab) respectively. Curcumin exhibits absorption maxima at around 425 nm can be due either to an n- π* transition or to a combination of π - π* and n- π* transitions (Figure 2a). The UV-Vis absorption of free curcuminaniline under investigation display mainly two bands observed in ethanol within the range 250500 nm. The first band showed absorption bands at the range 255-295 nm which could be assigned to π - π* and n - π* transitions in the aromatic ring or azomethine (C=N) while the second band 440-460 nm was assigned to curcumin moiety (Figure 2b).

2.4 2

Abs 1

-0.1 300

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600

Wavelength [nm] Fig 2a. UV-vis spectrum of CR http://ijcns.aizeonpublishers.net/content/2014/5/ijcns157-163.pdf

Fig 2b. UV-vis spectrum of CA 159

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The extracted curcumin have been quantitatively estimated spectrophotometrically and it was converted into percentage of curcumin. The amount of curcumin obtained from this method was around 9.24%. This is the higher curcumin percentage obtained from turmeric by the Soxhlet extraction technique.

Elemental Analysis The analytical data of curcumin and its schiff base complex are summarized in table 1. The complexes prepared are stable at room temperature and non-hygroscopic.

Table 1. Elemental analysis data of Curcumin (CR) and Curcuminaniline(CA). Sample code C 69.43 70.16

CR CA

Experimental value H N 5.20 6.12 4.71

C 68.47 73.12

Theoretical value H N 5.47 5.68 3.16

FT-IR Spectra Studies

Fig 3. FT-IR spectra of Curcumin (Bottom); Curcuminaniline (Top) IR spectra provide the valuable information about the nature of the binding mode and functional group present in the complexes. IR spectrographs of curcumin and curcuminaniline were taken by the Shimadzu FTIR 8700 instrument. From the data obtained, phenolic OH showed its weak broad band in the range of 3500-3200 cm-1 which were assigned to phenolic –OH group of curcumin moiety in both the formulations. The weak and broadness of these peaks could be observed mainly due to intra-molecular hydrogen bonding between the enolic –OH group with azomethine nitrogen atom. Existence of this enolic –OH group in all the ligands could be possible only due to stabilization of –OH

group by the conjugation present the curcumin system. The strong peak for (C=C) unsaturation remains outside the ring was confirmed by the observed peak in the region 1600 cm-1. The (C-O) band presence was assigned by the peak found at 1000-1250 cm-1. The peak due to the carboxyl group (C=O) was observed in both curcumin and its schiff base at around 1625 cm-1. This band in curcuminaniline is shifted to lower frequency 1584 cm-1 suggesting the bond breaking of oxygen with carbon and formation of azomethine C=N stretching vibration. Three characteristic peaks in the range of 1520 – 1350 cm-1 conforms the aromatic unsaturation (C=C) as in table 2.

Table 2. IR spectra bands of curcumin and curcuminaniline Compounds Curcumin (CR)

υ(Ph-OH) 3502

υ(C=O) 1625

Curcuminaniline (CA)

3215

1625

Functional groups (cm-1) υ(C=C) υ(Ar C=C) 1601 1505 1427(3peaks) 1358 1600 1509 1437(3peaks) 1414

υ(C-O) 1272 1024

υ(C=N) -

1239 1027

1584

Table 3. Effect of curcumin and curcuminaniline on antibacterial activity Bacterial Species S. aureus B.subtilis E. coli S.bacillus

Zone of inhibition diameter (mm sample-1) Standard drug (C) Curcumin(CR) Curcuminaniline(CA) 21 12 18 19 10 14 20 17 15 19 11 17

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Antibacterial activity The antibacterial activities of curcumin and its schiff base against two gram-positive (Staphylococcus aureus and Bacillus subtilis) and two gram-negative bacteria (Escherichia coli and Staphylococcus bacillus) were evaluated and their activity was compared to a well-known commercial antibiotic Chloramphenicol. The results are reported in table 3.

activity exhibited by the curcumin and its schiff base ligand were significantly appreciable. The results compared with standard drug have been indicated that the synthesized compounds were active but activity was lower than the standard drug and also showed nearly similar activity to the standard drug. Results of antibacterial evaluation is summarized in figure 4 a.

From these results, curcumin and curcuminaniline both were found to be more active against all the bacteria tested. The schiff base curcuminaniline has a greater effect against S.aureus, S.Bacillus and B.subtilis than the curcumin. Moreover, the zone of inhibition observed for those synthesized products (CR & CA) against E.coli showed the moderate antibacterial action when compared to the results obtained against other bacterial species. Therefore the

Antifungal activity Curcumin and its schiff base ligand were determined for their antifungal activity against four fungal strains Candida albicans, Curvularia lunata, Aspergillus niger and Trichophyton simii and their activity was compared with standard antifungal drug fluconazole. The results were shown in table 4.

Table 4. Effect of Curcumin and its schiff base on antifungal activity Fungal Species

Zone of inhibition diameter (mm sample-1) Standard drug (C) Curcumin(CR) Curcuminaniline(CA) 19 16 19 19 17 18 20 15 16 21 16 13

C.albicans C.lunata A.niger T.simii

B.subtilis

S.aureus 20

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Figure 4a. Antibacterial activity data of complexes http://ijcns.aizeonpublishers.net/content/2014/5/ijcns157-163.pdf

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Figure 4 b. Antifungal activity data of complexes From the results, it can be concluded that the activity of the schiff base ligand curcuminaniline were showed better inhibition compared to curcumin when tested against C.albicans, C.lunata and A.niger fungal species. However the activity of curcuminaniline was almost similar to the standard antibiotic (Fluconazole) but interestingly, it showed more activity than curcumin. Results of antifungal evaluation are summarized in figure 4 b.

CONCLUSION In summary, the bioactive curcumin and its schiff base ligand curcuminaniline synthesized from natural medicinal turmeric extract which showed over all significant antibacterial and antifungal activities. Moreover the schiff base ligand was more active against C.albicans, C.lunata and A.niger species which was almost similar to standard antibiotic drug and also observed appreciable inhibition activity against S.aureus and S.bacillus. From this work we could found the biologically more active turmeric (curcumin) variety (BSR-01) and its schiff base complex curcuminaniline. The synthesized curcuminaniline may http://ijcns.aizeonpublishers.net/content/2014/5/ijcns157-163.pdf

find its use in a wide variety of biological applications due to its significant bioactivities.

Acknowledgements We gratefully acknowledge Department of Chemistry, V.O.Chidambaram College, Tuticorin, India for providing UV and IR spectral analysis facility and also SAIF, Cochin, India for elemental analysis facility. We thank AMET University, India and Mahendra Engineering College, India for their support to do this work.

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