Storage stability of essential oil of cumin

International Journal of Food Properties

ISSN: 1094-2912 (Print) 1532-2386 (Online) Journal homepage: http://www.tandfonline.com/loi/ljfp20

Storage stability of essential oil of cumin (Cuminum Cyminum L.) as a function of temperature Leila Mehdizadeh, Abdollah Ghasemi Pirbalouti & Mohammad Moghaddam To cite this article: Leila Mehdizadeh, Abdollah Ghasemi Pirbalouti & Mohammad Moghaddam (2017): Storage stability of essential oil of cumin (Cuminum Cyminum L.) as a function of temperature, International Journal of Food Properties, DOI: 10.1080/10942912.2017.1354018 To link to this article: http://dx.doi.org/10.1080/10942912.2017.1354018

Accepted author version posted online: 04 Aug 2017.

Submit your article to this journal

View related articles

View Crossmark data

Full Terms & Conditions of access and use can be found at http://www.tandfonline.com/action/journalInformation?journalCode=ljfp20 Download by: [University of Florida]

Date: 04 August 2017, At: 06:38

International Journal of Food Properties

STORAGE STABILITY OF ESSENTIAL OIL OF CUMIN

TEMPERATURE

ip t

(CUMINUM CYMINUM L.) AS A FUNCTION OF

cr

1

an

us

Department of Horticulture, Faculty of Agriculture, Ferdowsi University of Mashhad, P.O. Box 91775-1163, Mashhad, Iran

2

M

Department of Medicinal Plants, Shahrekord Branch, Islamic Azad University, P.O. Box 166, Shahrekord, Iran

ce pt

ABSTRACT

ed

* Corresponding author; Mohammad Moghaddam E-mail address: [email protected]; [email protected] Tel.: +98 51 38796818; Fax: +98 51 38787430

Cumin (Cuminum cyminum L.) is one of the most important herbs known for stomach

disorders. In this study, during and temperature storage effects on the quality of cumin

Ac

Downloaded by [University of Florida] at 06:38 04 August 2017

Leila Mehdizadeh1, Abdollah Ghasemi Pirbalouti2, Mohammad Moghaddam1,*

essential oil were investigated. Changes in essential oils compositions were detected during storage for six months in a refrigerator (4°C), a freezer (-20°C), and at room temperature (25°C). The main constituents of the essential oil from the cumin fruits under different conditions of storage were cumin aldehyde belonging to oxygenated monoterpenes and p-cymene, and β-pinene belonging to monoterpene hydrocarbons. 1

Results indicated that at room temperature, the proportions of compounds with lower boiling temperatures such as β-pinene (1.57-10.03%) and p-cymene (14.93-24.9%) were decreased, however, cumin aldehyde (45.45-64.31%) increased during the cumin oil storage. Furthermore, the oil compositions showed the least alterations and C. cyminum

ip t cr

us

Keywords: Cuminum cyminum L.; Storage conditions; Temperature; Essential oil; Cumin

an

aldehyde. Received: 2017-02-10

ed

M

Accepted: 2017-07-07

ce pt

INTRODUCTION

Essential oils are aromatic and volatile liquids obtained from various species and parts of plants, herbs, and spices such as flowers, roots, bark, leaves, seeds, peel, fruits, and wood that described by a strong and generally pleasant odor and flavor.[1] For centuries, these

Ac


kept its primary quality when stored at low temperatures.

substances have been widely utilized in medicine, perfumery and cosmetics industries. Moreover, they have been added to foods as part of spices or herbs.[2] They constitute of very potent natural biologically active agents with various properties. They have been possessed a range of pharmaceutically relevant activities due to antioxidant, antifungal,

2

antibacterial, anti-parasitic, and insecticidal properties which are resulted in a wide field of applications.[3-5]

ip t

The essential oils are complex mixtures of several chemical components that mainly

include hydrocarbons, monoterpenes and sesquiterpenes, with the general formula

cr

us

ketones, phenols and oxides obtained from these hydrocarbons.[2, 6]Cuminum cyminum L. (“Zireh-e-Sabz” Persian name means green cumin), which is a well-known herbal

an

medicine in Iran, is an annual herb belonging to the family Apiaceae. The origin of C. cyminum is Egypt, Turkistan, and the east of Mediterranean area. Moreover, the herb is

ed

Algeria, and Turkey.[7]

M

cultivated widely in Iran, China, India, Morocco, southern Russia, Japan, Indonesia,

ce pt

The cumin fruit provide additional taste and flavor to foods as well as it has medicinal and therapeutic properties for centuries. In folk medicine, the cumin fruit is used as a diuretic, emmanogogic, antispasmodic, carminative, stimulant, astringent as well as remedy against indigestion, flatulence, toothache, dyspepsia, diarrhea, colic, epilepsy and

Ac


(C5H8)n. In addition, oxygenated compounds include alcohols, aldehydes, esters, ethers,

jaundice.[8, 9] Moreover, the cumin fruits contain yellow-colored fresh volatile oil (2 to

5% v/w) that imparts the characteristic aroma and medicinal value from the ripe fruits. Results of investigations[7-12] indicated that the essential oil from the cumin fruits have

high antifungal, antibacterial and antioxidant activities. Therefore, it is also used as a fumigant or additive in the storage of foodstuffs.[10] 3

Many phytochemical studies have been conducted to investigate the composition of the essential oil of cumin fruits.[11,

12]

These state that the major components of cumin

prominent one is cumin aldehyde in different percentage.[13,

ip t

essential oil are oxygenated compounds, especially aldehydes where in the most 14]

Variation in chemical

cr

composition of essential oils, although genetically controlled, may be influenced by the

us

season and phenological stage of harvest, drying and extraction methods, storage

an

conditions and distillation time and type which are led to higher essential oil content and better quality.[15-18] In addition, according to the previous investigations, the essential oils

M

compositions change due to the processing and storage of the isolated oil. Several factors such as temperature, light and oxygen availability make a very important influence on

ed

modification processes.[19] The impact of different storage conditions on the essential oils composition of Leonurus cardiac,[20] Majorana hortensis,[21] Rosa damascena (petals),[22]

ce pt

Thymus daenensis[23] and Myrtus communis[24] were studied before.

There is little chemical information about compositional changes of essential oils during

Ac


origin and environmental conditions, harvesting and post-harvesting stages like the

storage conditions. Therefore, the aim of this study was to evaluate the effect of storage conditions on the chemical composition of essential oil of C. cyminum. In this regard the

essential oil components of C. cyminum was analyzed in different storage condition include

room

temperature

(25°C),

(-20°C) during six month storage. 4

refrigerator

(4°C),

and

freezer

MATERIAL AND METHODS

ip t

Plant Material Cumin fruits were collected from the plants cultivated in Khorasan-e-Razavi province

cr

us

room temperature until oil extraction.

M

an

Isolation of Essential Oil and Storage Conditions

Cumin fruits were crashed and the essential oil isolated by hydrodistillation for 4 h, using

ed

a Clevenger-type apparatus. The distillated oils were dried over anhydrous sodium sulfate. In order to investigate the impacts of temperatures and different storage

ce pt

conditions on the compositions of distilled oils, the oil samples pour in three dark glasses, sealed and were subjected to different storage temperatures such as, refrigerator (4°C), freezer (-20°C), and room temperature (25°C) for six continuous months. The oils analysis of all storage treatments performed monthly. Every month each sample was injected to GC-FID and GC/MS and the compounds were detected. Moreover, to

Ac


region, North-eastern of Iran. The fruits were harvested at full mature stage and stored in

determine the exact effects of storage conditions on essential oil composition during the experiment period, the fresh extracted oil was analyzed immediately after extraction. The extracted essential oil was yellow in colour and had distinct sharp odor.

5

Oil Analysis Procedure

Composition of the essential oils was determined by gas chromatography (GC) and mass spectrophotometry (GC/MS). The GC analysis was done on an Agilent Technologies

ip t

7890 GC (Agilent Technologies, Santa Clara, CA) equipped with a single injector and a flame ionization detector (FID) using a HP–5MS capillary column (30 m × 0.25 mm,

cr

us

gas was helium (99.999% pure) at a flow rate of 0.8 mL/min. Initial column temperature was 60°C and programmed to increase at 4°C/min to 280°C. The injector temperature

an

was set at 300°C. Split injection was conducted with a ratio split of 1:40. Essential oil

M

samples of 0.1 µL were injected neat (directly).

GC-MS analyses of aromatic oil samples were performed on an Agilent Technologies

ed

7890 gas chromatograph coupled to Agilent 5975 C mass selective detector (MSD) and quadrupole EI mass analyzer (Agilent Technologies, Palo Alto, CA, USA). A HP–5MS

ce pt

5% column (coated with methyl silicone) (30 m × 0.25 mm, 0.25 µm film thicknesses) was used as the stationary phase. Helium was used as the carrier gas at 0.8 mL/min flow rate. The temperature was programmed from 60 to 280°C at 4°C/min ramp rate. The injector and the GC-MS interface temperatures were maintained at 290°C and 300°C,

Ac


0.25 µm film thicknesses) coated with 5% phenyl, 95% methyl polysiloxane. The carrier

respectively. Mass spectra were recorded at 70 eV. Mass range was from m/z 50-550. The ion source and the detector temperatures were maintained at 250 and 150°C, respectively. The samples (0.1 µL) were injected neat with 1:40 split ratio.

Identiﬁcation of Compounds 6

Constituents were identified by comparison of their RI (retention index) relative to C5-C24 n-alkanes obtained on a nonpolar HP-5MS column by comparison of the RI, provided in the literature, by comparison of the mass spectra with those recorded by the NIST 08

ip t

(National Institute of Standards and Technology) and Willey (ChemStation data system). The individual constituents were identified by retention indices and compared with

cr

M

an

RESULTS AND DISCUSSION

us

from the GC-FID peak areas without using any correction factors.

Different storage conditions can influence the chemical components of the essential oil.

ed

There are little researches about storage conditions of plant secondary metabolites, especially essential oils as volatile compounds. In this investigation, the compositions of

ce pt

hydro-distilled essential oils of C. cyminum were determined at different storage temperature and time. In total, 16 components were identified which are represented 92.6 to 99.86% of total detected compounds in essential oil samples (Tables 1 to 3). According to the GC/MS analysis shown in Tables, the main components of the essential oils from

Ac


constituents known from the literature.[25, 26] The percentage composition was computed

the fruits of cumin under all storage conditions during six months were cumin aldehyde belonging to oxygenated monoterpenes and p-cymene, and β-pinene belonging to monoterpene hydrocarbons.

7

According to the results of previous studies, the major components of cumin essential oil from various regions and phenological stages were cumin aldehyde, cumin alcohol, βpinene, ocimene, γ-terpinene, p-cymene, and safranal in different percentages.[12, 30, 31] In most studies, aldehyds compounds especially cumin aldehyde is the most prominent one, which was the same as our report. According to our knowledge, the pathway for

ip t

[32]

biosynthesis of cumin aldehyde and its precursor is not understood yet and the

cr

us

fresh and spicy notes of cumin oil are related to γ-terpinene and cumin aldehyde,

an

respectively.[33]

M

Results of this study indicated that the concentration of components with lower molecular weight decreased with the storage time especially at room temperature conditions (Tables

ed

1-3 and Fig. 1-3). The findings of this investigation indicated that at room temperature, the changes in the amounts of some compounds are as follow: β-pinene, as a main

ce pt

constituent of the cumin oil, was 10.93% immediately after oil extraction, then gradually decreased to 1.57% and indicated that about 85.63% decline at the end of storage period. The trend of β-pinene evolution following one to six months after essential oils storage was 8.23, 42.45, 51.87, 55.26, 75.85, and 85.63%, respectively.

Ac


mechanism of transformation for essential oils compound is in doubt. In addition, the

The second main component which showed a same trend with β-pinene was p-cymene which showed a decreasing trend with the storage time. The quantity of p-cymene was 26.3% at the time of oil extraction and then its amounts were 24.81, 24.09, 23.78, 19.71, 8

16.19, and 14.93%, after one to six months, respectively. The concentration of p-cymene decreased up to 43.23% after six months storage (Table 1 and Fig. 1). It can be due to evaporation, oxidation and other unwanted changes in essential oils constituents during storage period. It is clear that with passing time, lower boiling compounds have markedly

ip t cr

us

The most important results of the present study were the increasing trend in the quantities of cumin aldehyde by the storage time at room temperature. The cumin aldehyde was

an

46.10% immediately after oil extraction, then gradually reached to 63.31% after six months and showed a trend of 37.33% growth at the end of storage period. The

M

increasing trend of this components evolution following one to six months after essential oil storage were 46.67, 48.46, 52.32, 56.29, 60.21, and 63.31%, respectively (Table 1 and

ed

Fig. 1). At refrigerator and freezer temperature the same trends was observed. β-Pinene and p-cymene showed a decreasing trend with the storage time, however, cumin

ce pt

aldehyde, as the major constituent in the cumin oil, increased during the cumin oil storage (Table 2, 3 and Fig. 2). The comparison of essential oils constituents between different conditions of storage (temperature and time) indicated that the major components amounts were intensively changed during storage at room temperature compared to other

Ac


decreased at room temperature storage condition.

storage conditions (Fig. 2). Moreover, according to the results of this study, 2thiophenecarboxaldehyde was identified in the essential oil of cumin. It seems to be a new compound for the essential oil of cumin (Table 1).

9

On the other hand, our findings indicated that safranal decreased during the storage. In this regard, the findings of our work indicted that the concentration of safranal with a lower molecular weight decreased by prolonging the storage time (Table 3). This phenomenon can be due to evaporation, oxidation and other unwanted changes in the

ip t

essential oil components during storage period.[20] It is clear that with passing time, lower boiling compounds markedly decreased in refrigerator and particularly at room

cr

us

Furthermore, the effect of various temperatures such as room temperature (25°C), refrigerator (4°C), and freezer (-20°C) on the essential oil composition of different

M

an

medicinal plants were studied before.[20, 23, 28]

The primary components of essential oils from plants are monoterpenes and the effects of

ed

many medicinal herbs have been attributed to them.[27] In this study, monoterpenoids were the most components that identified in cumin essential oil. All samples at different

ce pt

storage conditions are mainly composed of oxygenated monoterpenes, represented exclusively by cumin aldehyde with different percentage from 45.59 to 63.31% in different time and temperature. In addition, monoterpene hydrocarbons, including pcymene and β-pinene were the second group of chemical components (Table 1-3 and Fig.

Ac


temperature conditions. However, it was very slight in freezing temperature.[23]

3).

Changes in essential oil compositions of Melissa officinalis[29] and Thymus daenensis[23] were evaluated during storage for four months in a refrigerator (4°C), a freezer (-20°C), and at room temperature (25°C). In conformity with our results, they reported that, at 10

room temperature, the proportions of compounds with lower boiling temperatures were decreased. Furthermore, the oil compositions showed the least alterations and kept their

ip t

primary quality when stored at low temperatures, particularly at -20°C.

Variation in chemical composition of cumin oil indicated that different chemotypes of C.

cr

us

origin of the studied cumin. In conformity with our findings, results of previous studies showed the major component in the essential oil of the Spanish cumin.[34] In agreement

an

with our findings, cumin aldehyde chemotype was found by Li & Jiang[10] and Oroojalian

M

et al.[11] that studying Turkish, Chinese and Egyptian cumin fruits.

ed

On the other hands, the essential oils should be stored in tightly closed, darkened glass containers in a cool place to ensure lasting quality.[35] According to the previous

ce pt

investigations on changing in the composition of the essential oil of marjoram during storage, in significant changes in the composition of the essential oil was observed when storage in the dark glass container for one year and its organoleptic characteristics remained largely unaffected. Whereas storage it in the light container cause to change the

Ac


cyminum L. exist in the world. In fact, several chemotypes were reported according to the

composition of the oil, due to chemical transformations of terpenoids. In significant changes in the content of substances in the dark, may be depended on their structure and reactivity. Oxidation of the most labile components of the oil was the main process. [36]

11

Only few researches have been performed to assess the effect of storage conditions on the stability of essential oils.[19, 36, 37] According to the results of preceding investigations, the composition of essential oils from cardamom (Elettaria cardamomum Maton L.) and clove (Caryophyllus aromaticus L.)[38] changed in storage condition, which affected their

ip t

properties. The oil composition may undergo considerable changes upon processing and storage conditions. Previous reports indicated that several factors such as different

cr

us

oxygen availability can affected the essential oil quality and composition.[19, 23, 39, 40, 41] This may lead to changing color, an increase in viscosity or the formation of an

an

unpleasant, often sharp aroma by alternations in composition and a rise of oxidized

ed

reactions may accrue.[42-44]

M

compounds. Moreover, due to the terpenoid oxidation products some allergic skin

ce pt

CONCLUSION

The main process during the storage of essential oil is evaporating the compounds with a lower boiling temperature, mostly monoterpene hydrocarbons. From the findings of this study, best results of the major constituents were obtained from -20°C, and 4°C (the total

Ac


harvest time, storage conditions, storage duration at different temperature, light and

of 39.67% monoterpene hydrocarbons after distillation is reduced to 31.36% and 27.59%, respectively after six months). So there was a higher decrease in the oil quality during the storage period of six months in room temperature. It is concluded that the essential oil of C. cyminum which was stored in refrigerator and freezer kept its primary quality better in comparison with room temperature storage. In total, the storage of C. cyminum oil at low 12

temperatures can prevent decreasing the concentrations of the oil compounds and helps maintaining the essential oil primary quality with the least alterations. These results may be increased to storage the essential oils of plants with the same chemical characteristics. So that, these useful findings can helps essential oil producers and consumers for using

ip t

this oil and its compounds in different related industries such as food, cosmetic and

medicinal products. In conclusion, different storage conditions of plant secondary

cr

an

us

with various aromatic plant essential oils that constitute of different chemical compounds.

M

REFERENCES

ed

1. Sanchez, E.; Garcia, S.; Heredia, N. Extracts of edible and medicinal plants damage membranes of Vibrio cholerae. Applied Environmental Microbiology 2010, 76,

ce pt

6888–6894.

2. Prabuseenivasan, S.; Jayakumar, M.; Ignacimuthu, S. In vitro antibacterial activity of some plant essential oils. BMC Complementary and Alternative Medicine 2006, 6(1), 39–44.

Ac


metabolites especially essential oils, is an interesting topic which needs further studies

3. Adorjan, B.; Buchbauer, G. Biological properties of essential oils: An updated review. Flavour and Fragrance Journal 2010, 25, 407–426.

4. Silva, F.; Ferreira, S.; Duarte, A.; Mendonca, D.I.; Domingues, F.C. Antifungal activity of Coriandrum sativum essential oil, its mode of action against Candida species and potential synergism with amphotericin B. Phytomedicine 2011, 19, 42–47. 13

5. Bajpai, V.K.; Baek, K.-H.; Kang, S.C. Control of Salmonella in foods by using essential oils: A review. Food Research International 2011, 45, 722-734. 6. Espina, L.; Somolinos, M.; Loran, S.; Conchello, P.; Garcia, D.; Pagan, R. Chemical composition of commercial citrus fruit essential oils and evaluation of their

ip t

antimicrobial activity acting alone or in combined processes. Food Control 2011, 22, 896–902.

cr

us

quality components of cumin (Cuminum cyminum L.). Research Journal of Agriculture and Biological Sciences 2006, 2, 336–340.

an

8. El–Ghorab, A.H.; Nauman, M.; Anjum, F.M.; Hussain, S.; Nadeem, M. A Comparative Study on chemical composition and antioxidant activity of ginger (Zingiber

M

officinale) and cumin (Cuminum cyminum). Journal of Agricultural and Food Chemistry 2010, 58, 8231–8237.

ed

9. Allahghdri, T.; Rasooli, I.; Owlia, P.; Nadooshan, M.J.; Ghazanfari, T.; Taghizadeh,

ce pt

M.; Astaneh, S.D.A. Antimicrobial property, antioxidant capacity, and cytotoxicity of essential oil from cumin produced in Iran. Journal of Food Science 2010, 75,

H54–H61.

10. Li, R.; Jiang, Z.T. Chemical composition of the essential oil of Cuminum cyminum L. from China. Flavour and Fragrance Journal 2004, 19, 311–313.

Ac


7. Tuncturk, R.; Tuncturk, M. Effects of different phosphorus levels on the yield and

11. Oroojalian, F.R.; Kasra-Kermanshahi, R.; Azizi, M.; Bassami, M.R. Phytochemical composition of the essential oils from three Apiaceae species and their antibacterial effects on food-borne pathogens. Food Chemistry 2010, 120, 765–770.

14

12. Hajlaoui, H.; Mighri, H.; Noumi, E.; Snoussi, M.; Trabelsi, N.; Ksouri, R.; Bakhrouf, A. Chemical composition and biological activities of Tunisian Cuminum cyminum L. essential oil: a high effectiveness against Vibrio spp. strains. Food Chemical and Toxicology 2010, 48, 2186–2192.

ip t

13. Sowbhagya, H.B.; Sathyendra Rao, B.V.; Krishnamurthy, N. Evaluation of size reduction and expansion on yield and quality of cumin (Cuminum cyminum) seed

cr

us

14. Bettaieb, I.; Bourgou, S.; Wannes, W.A.; Hamrouni, I.; Limam, F.; Marzouk, B. Essential oils, phenolics, and antioxidant activities of different parts of cumin

an

(Cuminum cyminum L.). Journal of Agricultural and Food Chemistry 2010, 58, 10410–10418.

M

15. Moghaddam, M.; Omidbaigi, R.; Sefidkon, F. Changes in content and chemical composition of Tagetes minuta oil at various harvest times. Journal of Essential Oil

ed

Research 2007, 19, 18–20.

ce pt

16. Figueiredo, A.C.; Barroso, J.G.; Pedro, L.G.; Scheffer, J.J.C. Factors affecting secondary metabolite production in plants: volatile components and essential oils. Flavour and Fragrance Journal 2008, 23, 213–226.

17. Demuner, A.J.; Barbosa, L.C.A.; Magalhaes, C.G.; Da Silva, C.J.; Maltha, C.R.A.; Pinheiro, A.L. Seasonal variation in the chemical composition and antimicrobial

Ac


oil. Journal of Food Engineering, 2008, 84, 595–600.

activity of volatile oils of three species of Leptospermum (Myrtaceae) grown in Brazil. Molecules 2011, 16, 1181–1191.

18. Moghaddam, M.; Khaleghi Miran, S.N.; Ghasemi Pirbalouti, A.; Mehdizadeh, L.; Ghaderi, Y. Variation in essential oil composition and antioxidant activity of cumin

15

(Cuminum cyminum L.) fruits during stages of maturity. Industrial Crops and Products 2015 b, 70, 163–169. 19. Nguyen, H.; Campi, E.M.; Jackson, W.R.; Patti, A.F. Effect of oxidative deterioration on flavor and aroma components of lemon oil. Food Chemistry 2009, 112, 388–393.

ip t

20. Mockute, D.; Bernotiene, G.; Judentiene, A. Storage-induced changes in essential oil

us

21. Misharina, T.A.; Polshkov, A.N.; Ruchkina, E.L.; Medvedeva, I.B. Changes in the composition of the essential oil of Marjoram during Storage. Applied Biochemistry

an

and Microbiology 2003, 39(3), 311–316.

22. Mohamadi, M.; Mostafavi, A.; Shamspur, T. Effects of storage on essential oil

M

content and composition of Rosa damascena Mill petals under different conditions. Journal of Essential Oil Bearing Plants 2011, 14, 430–441.

ed

23. Rowshan, V.; Bahmanzadegan, A.; Saharkhiz, M.J. Influence of storage conditions on

ce pt

the essential oil composition of Thymus daenensis Celak. Industrial Crops and Products 2013, 49, 97–101.

24. Bahramzadegan, A.; Rowshan, V.; Saharkhiz, M.J. Essential oil composition of Myrtus communis L. under different storage condition. Journal of Essential Oil Bearing Plants 2015, 18(6), 1467-1475.

Ac


commercial herbs. Chemija 2005, 2, 29–32.

cr

composition of Leonurus cardiaca L. plants growing wild in Vilnius and of

25.

Adams,

R.P.

Identification

of

Essential

Oil

Components

by

Gas

Chromatography/Mass Spectrometry. Allured Publications, Carol Stream, IL. 2007.

26. McLafferty, F.W. Wiley Registry of Mass Spectral Data, 9th ed. John Wiley and Sons, Inc., Hoboken, NJ, 2009, pp.662.

16

27. Gherlardini, C.; Galeotti, N.; Mazzanti, G. Local anaesthetic activity of monoterpenes and phenylpropanes of essentialoils. Planta Medica 2001, 67, 564–566. 28. Baydar, H.; Schulz, H.; Kruger, H.; Erbas, S.; Kineci, S. Influences of fermentation time, hydro-distillation time and fractions on essential oil composition of Damask

ip t

Rose (Rosa damascena Mill.). Journal of Essential Oil Bearing Plants 2008, 11(3), 224–232.

cr

us

Balm Mint Herb (Lamiaceae) in Iran. Industrial Crops and Products 2014, 52, 575– 581.

an

30. Rebey, I.B.; Jabri-Karoui, I.; Hamrouni-Sellami, I.; Bourgou, S.; Limam, F.; Marzouk, B. Effect of drought on the biochemical composition and antioxidant

2012, 36, 238–245.

M

activities of cumin (Cuminum cyminum L.) seeds. Industrial Crops and Products

ed

31. Moghaddam, M.; Ghasemi Pirbalouti, A.; Mehdizadeh, L.; Pirmoradi, M.R. Changes

ce pt

in composition and essential oil yield of Ocimum ciliatum at different phenological stages. European Food Research Technology 2015a, 240, 199–204.

32. Derakhshan, D.; Sattari, M.; Bigdeli, M. Effect of subinhibitory concentrations of cumin (Cuminum cyminum L.) seed essential oil and alcoholic extract on the morphology capsule expression and urease activity of Klebsiella pneumonia

Ac


29. Najafian, Sh. Storage conditions affect the essential oil composition of cultivated

.International Journal of Antimicrobial Agents 2008, 32, 432–436.

33. Jirovetz, L.; Buchbauer, G.; Stoynanava, A.; Georgiev, E.; Damianova, S. Composition, quality control and antimicrobial activity of the essential oil cumin

17

(C. cyminum L.) seeds from Bulgaria that had been stored for up 36 years. International Journal of Food Science and Technology 2005, 40, 305–310. 34. Viuda-Martos, M.; Ruiz-Navajas, Y.; Fernandez-Lopez, J.; Angel Perez-Alvarez, J. Chemical composition of the essential oils obtained from some spices widely used

ip t

in Mediterranean region. Acta Chimica Slovenica 2007, 54, 921–926.

35. Buckle, J. Clinical Aromatherapy: Essential Oils in Practice, 2nd ed. Churchill

cr

us

36. Misharina, T.A.; Polshkov, A.N. Antioxidant properties of essential oils: Autoxidation of essential oils from laurel and fennel and of their mixtures with

an

essential oil from coriander. Applied Biochemistry and Microbiology 2005, 41, 610–618.

M

37. Haddouchi, F.; Chaouche, T.; Lazouni, H.A.; Benmansour, A. Physicochemical study essential oils of Thymus fontanesii according to its conservation. Der Pharma

ed

Chemica 2011, 3, 404–410.

ce pt

38. Gopalakrishnan, N. Studies on the storage quality of carbon dioxide-extracted cardamom and clove bud oils. Journal of Agricultural and Food Chemistry 1994, 42(3), 796–798.

39. Kazaz, S.; Erbas, S.; Baydar, H. The effects of storage temperature and duration on essential oil content and composition oil Rose (Rosa damascena Mill.). Turkish

Ac


Livingstone, Edinburgh. 2003.

Journal of Field Crops 2009, 4, 89–96.

40. Turek, C.; Stintzing, F.C. Evaluation of selected quality parameters to monitor essential oil alteration during storage. Journal of Food Science 2011b, 76, C1365– C1375.

18

41. Kumar, R.; Shama, S.; Sood, S.; Agnihotri, V.K.; Singh, B. Effect of diurnal variability and storage conditions on essential oil content and quality of damask rose (Rosa damascena Mill.) flowers in north western Himalayas. Scientia Horticulturae 2013, 154, 102–108.

ip t

42. Hagvall, L.; Bucktorp, C.; Svensson, S.; Nyman, G.; Borje, A.; Karlberg, A.-T.

Fragrance compound geraniol forms contact allergens on air exposure.

cr

us

sensitization. Chemical Research in Toxicology 2007, 20, 807–814.

43. Brared-Christensson, J.; Forsstrom, P.; Wennberg, A.-M.; Karlberg, A.-T.; Matura,

Dermatitis 2009, 60, 32–40.

an

M. Air oxidation increases skin irritation from fragrance terpenes. Contact

M

44. Brared-Christensson, J., Matura, M., Gruvberger, B., Bruze, M., & Karlberg, A.-T. Linalool-A significant contact sensitizer after air exposure. Contact Dermatitis

ce pt

ed

2010, 62, 32–41.

Ac


Identification and quantification of oxidation products and effect on skin

19

70 60 50 40 30 20 10 0

After distillation 1 month after 2 month after 3 month after

ip t

Percantage (%)

Fig.1. Changes of the major compounds of Cuminum cyminum essential oil during six months storage at room temperature

4 month after 5 month after

cr

us

ce pt

ed

M

an

The main components

Ac


6 month after

20

Fig.2. Percentage of the main compounds of C. cyminum essential oils after six months of storage in room temperature (25°C) refrigerator (4°C) and freezer (−20°C). Cumin aldehyde

β- Pinene

p-Cymene

70

ip t

50 40

20 10 0 Room Refrigerator Storage conditions

Freezer

ce pt

ed

M

an

After distillation

us

cr

30

Ac


Percantage(%)

60

21

Fig. 3. Percentage of grouped components of C. cyminum essential oils after six months of storage in room temperature (25°C) refrigerator (4°C) and freezer (−20°C). 90

Oxygenated monoterpenes

Monoterpene hydrocarbons

Others

80

ip t

60 50 40 30

cr

Percentage (%)

70

0 After distillation

Room

us

10 Refrigerator

ce pt

ed

M

an

Storage conditions

Ac


20

22

Freezer

Table 1. Chemical composition of C. cyminum essential oils during six months storage at room temperature (25°C).

0.32 6.29 0 24.09 0.24 0.45 0.15 1.14 1.27 0.43 1.08 48.46 1.9 2.53 2.68 4.03

0.25 5.26 0 23.78 0.11 0.53 0 1.04 1.21 0.45 1.41 52.32 1.92 2.47 3.01 4.56

39.67 56.18 1.53 97.38

35.86 57 2.33 95.19

ed ce pt 23

31.09 61.29 2.68 95.06

29.4 65.91 3.01 98.32

6

0 4.89 0 19.71 0 0.65 0 1.58 1.55 0.50 1.89 56.29 2.1 2.47 3.02 4.6

0 2.64 0 16.19 0 0.55 0 2.3 2.32 0.51 1.81 60.21 2.2 1.94 3.53 5.1

0 1.57 0 14.93 0 0.51 0 2.4 0.56 0.53 0.71 63.31 2.47 1.78 4.68 6.41

24.6 71.63 3.02 99.25

18.83 76.94 3.53 99.3

16.5 78.68 4.68 99.86

ip t

0.54 10.03 0.06 24.81 0.24 0.47 0.18 0.27 0.27 0.43 1.1 46.67 1.93 2.76 2.33 3.1

Month after distillation (%) 2 3 4 5

cr

α-Pinene 932 β- Pinene 977 Myrcene 989 p-Cymene 1025 Limonene 1028 1,8-Cineole 1031 γ-Terpinene 1057 Menthone 1154 Menthol 1172 Pulegone 1194 p-Cumenol 1231 Cumin aldehyde 1245 Safranal 1249 Cumin alcohol 1292 2-Thiophenecarboxaldehyde 1320 Cuminic acid 1440 Grouped components (%) Monoterpene hydrocarbons Oxygenated monoterpenes Others Total ∗ Retention indices (RI) on HP-5 column.

1

M

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16

After distillation (%) 0.64 10.93 0.12 26.3 0.48 0.42 1.20 0.24 0.23 0.58 0.80 46.10 1.95 3.51 1.53 2.35

us

RI∗

an

Compounds

Ac


No.

Month after distillation (%) 2 3 4 5 0.54 0.59 0.73 0.67 9.85 9.83 9.05 8.54 0 0 0 0 26.32 23.11 23.09 22.45 0.41 0.36 0.34 0.28 0.49 0.83 0.63 0.38 0.3 0.31 0.34 0.33 0.87 2.28 1.2 0.23 0.93 2.94 1.14 0.27 0.47 0.44 0.4 0.41 1.20 1.23 1.04 1.28 47.31 48.63 49.6 49.97 1.93 1.9 1.96 1.99 2.77 2.69 2.13 2.27 2.72 2.92 3.36 2.45

2.35

1.5

1.2

1.78

2.09

2.43

4.6

39.67 56.18 1.53 97.38

38.46 55.62 1.84 95.92

37.42 57.17 2.72 97.31

34.2 62.72 2.92 99.84

33.55 60.19 3.36 97.1

32.27 59.23 2.45 93.95

27.59 62.33 2.68 92.6

ed ce pt 24

6 0.31 5.69 0 21.44 0 0.2 0.15 0.27 0.56 0.53 0.71 50.52 2.47 2.47 2.68

ip t

α-Pinene 932 β- Pinene 977 Myrcene 989 p-Cymene 1025 Limonene 1028 1,8-Cineole 1031 γ-Terpinene 1057 Menthone 1154 Menthol 1172 Pulegone 1194 p-Cumenol 1231 Cumin aldehyde 1245 Safranal 1249 Cumin alcohol 1292 21320 Thiophenecarboxaldehyde 16 Cuminic acid 1440 Grouped components (%) Monoterpene hydrocarbons Oxygenated monoterpenes Others Total ∗ Retention indices (RI) on HP-5 column.

1 0.5 10.91 0 26.23 0.52 0.3 0.3 0.28 0.24 0.56 1.24 46.11 1.9 3.49 1.84

M

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15

After distillation (%) 0.64 10.93 0.12 26.3 0.48 0.42 1.20 0.24 0.23 0.58 0.80 46.10 1.95 3.51 1.53

cr

RI

an

Compounds

Ac


No.

us

Table 2. Chemical composition of C. cyminum essential oils during six months storage at refrigerator temperature (4◦C).

Table 3. Chemical composition of C. cyminum essential oils during six months storage at freezer temperature (−20◦C).

0.47 9.58 0.13 26.46 0.37 0.36 1.31 0.17 0.19 0.5 1.2 45.59 0.81 3.69 2.66

0.39 9.05 0.12 26.47 0.34 0.38 1.18 0.66 0.54 0.58 1.35 47.42 0 3.04 2.7

0.55 8.94 0 26.22 0.45 0.48 1.39 0.53 0.42 0.59 1.21 48.07 0 3.08 3.99

2.35

2.22

2.74

39.67 56.18 1.53 97.38

38.32 54.73 2.66 95.71

37.55 56.71 2.7 96.96

ed ce pt 25

6

0.5 8.57 0 22.76 0.42 0.5 1.53 0.93 1.07 0.5 1.2 51.11 0 2.7 3.41

0.5 7.63 0 21.28 0.41 0.44 1.54 0.68 0.69 0.55 1.2 51.22 0 1.81 2. 73

2.72

2.75

2.96

4.15

37.55 57.1 3.99 98.64

35.77 59.77 3.02 98.56

33.78 60.97 3.41 98.16

31.36 60.74 2.73 94.83

ip t

0.53 8.73 0 24.53 0.47 0.73 1.51 1.86 1.8 0.53 1.12 48.38 0 2.6 3.02

cr

α-Pinene 932 β- Pinene 977 Myrcene 989 p-Cymene 1025 Limonene 1028 1,8-Cineole 1031 γ-Terpinene 1057 Menthone 1154 Menthol 1172 Pulegone 1194 p-Cumenol 1231 Cumin aldehyde 1245 Safranal 1249 Cumin alcohol 1292 2Thiophenecarboxaldehyde 16 Cuminic acid 1440 Grouped components (%) Monoterpene hydrocarbons Oxygenated monoterpenes Others Total ∗ Retention indices (RI) on HP-5 column.

1

M

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15

Month after distillation (%) 2 3 4 5

After distillation (%) 0.64 10.93 0.12 26.3 0.48 0.42 1.20 0.24 0.23 0.58 0.80 46.10 1.95 3.51 1.53

us

RI

an

Compounds

Ac


No.