July 14, 2007
Composition of the Essential Oil of the Flowering Aerial Parts of Iranian Crambe Orientalis L.
By Safaei-Ghomi, Javad Bamoniri, Abdolhamid; Hatami, Alireza; Batooli, Hossein
Abstract The essential oil of flowering aerial parts of Crambe orientalis L., which belongs to Cruciferae family, was obtained by hydrodistillation method in 0.1% yield and analyzed by GC and GC/ MS. Twenty-three compounds representing 98.7% of the oil were identified. Among them 3-butenyl isothiocyanate (51.4%), henicosane (9.3%), epoxy-oleic acid (7.6%) and hexadecanoic acid (7.2%) were the major constituents of the oil.
Key Word Index
Crambe orientalis, Crambe persica, Cruciferae, essential oil composition, 3-butenyl isothiocyanate.
Crambe, which belongs to the family Cruciferae, consists of about 40 species (1) distributed in Europe, southwest and central Asia and eastern Aferica (2). Cruciferae family is used in traditional medicines (3-5). Many genera of this family have antimicrobial effect because of their isothiocyanate derivatives (6,7). Numerous plants in this family used as vegetable produce indol-3-carbinole in cooking process thus they have anticarcinogenic and antimutagenic properties (8-10). This family has also antioridative effect (11). Crambe maritima, which is known as Sea-kale, is used as a vegetable (12, 13). It is grown for its blanched shoots that heal injury (14). Crambe abyssinica Hochst, known as Abyssinian-kale, is used as an animal food (15) and its oilseed is used in industry (16-18). Crambe cordifolia is used as potherb (13) and cooked vegetable (19, 20) as a cure for itch (21). Crambe genus in Iran includes three species, Crambe hisperica, which grows in Kouzestan, Lorestan and Pars Provinces, Crambe kotschyana, which grows in Pars, Khorasan and Mazandaran Provinces and Crambe orientalis L. that often grows in Pars, Mazandaran, Azarbayejan, Hamedan, Lorestan, Markazi, Semnan, Kerman, Isfahan, Tehran, and Yazd provinces (2,22). These species have an antipruritic effect and are used as vegetable and are nutritious (19, 20,23-25). The essential oil of Crambe orientalis (syn. C. persica Boiss.), which grows in Iran and named as "Sepideh" has not been studied to date. So we decided to characterize the chemical composition of its oil. The present paper deals with the detailed analysis of the oil by capillary GC and GC/MS with the determination of the percentage composition.
Plant Material: Flowering aerial parts ofCrambe orientate L. were collected from Kashan area (Isfahan Province, Iran) at an altitude of 2600 m in June 2005 and were dried in the shade (at room temperature). Voucher specimens of the plant were deposited in the Herbarium of Research Institute of Forests and Rangelands, Kashan, Iran.
Isolation procedure: The air-dried aerial parts of the plant (100 g) were powdered and the volatile fraction was isolated by hydrodistillation method in an all-glass Clevenger-type apparatus for 3 h according to the method recommended in the European Pharmacopoeia (26). After decanting, the yellow oil (0.1 mL) was dried over anhydrous sodium sulfate and stored in vial at low temperature (40C) before analysis.
GC and GC/MS Analysee: GC analysis of oil was conducted using a Thermoquest-Finnigan Trace GC instrument equipped with a DB-I fused silica column (60 m x 0.25 mm, film thickness 0.25 pm). Nitrogen was used as the carrier gas at the constant flow of 1.1 mL/min. Oven temperature was held at 60[degrees]C for 3 min and then programmed to 25O0C at a rate of 5[degrees]C/min, and then held at 25O0C for 10 min. The injector and detector (FID) temperatures were kept at 25O0C and 28O0C, respectively. GC/M S analysis was carried out on a Thermoquest-Finnigan Trace GC/MS instrument equipped with a DB-I fused silica column (60 m ? 0.25 mm, film thickness 0.25 pm) and operating under the same conditions as described above. The quadrupole mass spectrometer was scanned over the 45-465 amu with an ionizing voltage of 70 eV and an ionizing current of 150 uA.
Identification of components: The constituents of the oil were identified by calculation of their retention indices under temperature-programmed conditions iorn-alkanes (C6-C24) and the oil on a DB-I column under the same conditions. Identification of individual compounds was made by comparison of their mass spectra with those of the internal reference mass spectra library (Wiley 7.0) or with those of reported in the literature (27). Quantitative data were obtained from FID area percentages without the use of correction factors.
Results and Discussion
The flowering aerial parts of Crambe orientalis L. yielded 0.1% v/ w a yellowish oil which was determined by gravimetric method and calculated as percentage respecting the mass of starting dry plant material. In this oil, 23 components, which represented about 98.7% of the total composition, were identified and listed in Table I with their percentage. Constituents are listed in order of their elution from DB-I column. The major constituents are 3-butenyl isothiocyanate (51.4%), henicosane (9.3%), epoxy-oleic acid (7.6%), hexadecanoic acid (7.2%) and nonadecane (5.6%). The first major component, 3-butenyl isothicyanate, has been found in Raphanus sativus L. var. niger oil in 5.2% (5). This compound has also been determined in Diplotaxis harm Forsk. (12.8%), in Erucaria microcarpa Boiss. (26.9%) (6), and in horseradish (Armoracia rusticana) as third major component (28). In these herbal plants, which all are from Cruciferae family, isothiocyanate derivatives are the typical major components. Henicosane, which is the second major component, has also been found in D. harra, E. microcarpa (6), and Brassica oleracea var. gongylodes L. stem (29) in trace amounts. The third major component, epoxy-oleic acid has been found in Thespesia populnea L. (Malvaceae) (30). The predominance of hexadecanoic acid, which is 7.2% in Crambe orientalis oil, has also been found in the oil of D. harra (5.9%) and E. microcarpa (5.3%) (6). A comparison of the results with the literature showed significant differences for oils, which can be attributed to either climatological factors or genetic differences of the plants.
In a comparative study about the essential oils of the Cruciferae family (5-10,28,29), we found that, these herbal plants have an antimicrobial effect because of having large amounts and variety of isothiocyanate derivatives. Furthermore 3-butenyl isothiocyanate has been shown to possess an antimutagenic effect (31) and we identified 3-butenyl isothiocyanate in large amount (51.4%) in Iranian Crambe orientalis oil.
Financial support made by the Research Affairs Office of the University of Kashan, Kashan, I. R, Iran is gratefully acknowledged.
Table I. Percentage Composition of the oil of the aerial parts of Crambe orientalle Iron Kashan area
1. J. Franclsco-Ortega, J. Fuertes-Agullar, C. Gomez-Campo, A. SantosGuerra, R. K. Jansen, Internal transcribed spacer sequence phytogeny of Crambe L. ssrass\caceae):molecularoatarevealtwooMworldd/ sjunctlons. Molecular Phylogenet. Evol., 11,361-380 (1999).
2. V. Mozaffarian, A dictionary of Iranian plant names. Farhang- e Moaser, Tehran (1996).
3. A.A. Bin Slna, AI-Qanun FI-Tlbb. Book II, p. 300, Institute of History of Medicine and Medical Research, New Delhi (1987).
4. H. Mlrhaydar, Plants Used for Prevention and Treatment of Diseases. Vol. 1, p. 33, Daftare Nashre Eslamy, Tehran (1995).
5. S.AfsharypuorandM.H.Balam, Vb/ettfe Constituents ofRaphanussatlvus L. var. nlger seeds. J. Essent. oil Res., 17,440- 441 (2005).
6. F.A.HashemandM.M.Saleh,j4nt/m/c/iob/e/ componen(5ofsomecruclferae plants (Diplotaxis narra Forsk. and Erucarla mlcrocarpa Boiss.). Phytother. Res., 13,329-332 (1999).
7. C.M. LIn, J.F. Preston, and C.I WeI, Antibacterial Mechanism of AIIyI lsothlocyanate. J. Food Prot., 63.727-734 (2000).
8. A. Behfar, M.R.OvelsI, S.M. Sharlatpanahl, H.Komalll Zadeh, O.Sabzevart and M. Hamedl, Analysis oflndoto-3-cartlnole (an antlcarc/nogenlc agent In cruclferaej by Unary sweep voltammetry. J. Med. Plants, 2(5), 57-63 (2003).
9. T.A. Broadbent and H.S. Broadbent, The chemistry and pharmacology of lndole-3-carblnol (indole-3-methanol) and 3- (methoxymethyl)lndole. Part I, Curr. Med. Chern., S, 337-52 (1998).
10. T.A. Broadbent and H.S. Broadbent, The chemistry and pharmacology of indole-3-carbinol(!ndole-3-methanol) and 3- (methoxymethyl)lndole. Part II, Curr. Med. Chem., 5,469-91 (1998).
11. R. Saijo, R. Wang, K. Salto, R. Nakata, S. Ofujl, T. Lnoue, Y. Morl and Y. Tabata, Antlox/dative activity /nCrucIferae family vegetables and the effect o/(rte nsgeiaWes on ediWeoAOXWafcn.!!"1 International flavor conference: Recent advances In food & flavor chemistry, Pythagorion, Samos Island (2004).
12. GAM. Scon and R.E. Randall. Biological Flora of the British Isles. J. Ecol., 64, 1077-1091 (1976).
13. S. Facclola, Cornucopia, a source book of edible plants. Kampong Publ. vista, CA (1990).
14. A. Zargari, Medicinal plants, Vol.1, pp. 243-244, Tehran University Press, Tehran (1990).
15. Q.M. Markle, Food and feed crops of the United States, 2nd ed., Meister Pub., WHIoughby, Ohio (1998).
16. U.S. Department of Agriculture. Crambe: A potential new crop for Industrial and feed uses. Agr. Res. Serv., USDA, ARS 34-42. Washington, DC. (1962).
17. R.K. Downey, Agricultural and genetic potentials of cruciferous oilseed crops. J. Amer. Oll Chem. Soc. 48, 718-722 (1971).
18. H.J. Nieschlag and I.A. Wolff, Industrial uses of high eructe oils. J. Amer. Oll. Chem. Soc. 48, 723-727 (1971). 19. T. Tanaka, Tanaka's Cyclopaedia of Edible Plants of the World. Kelgaku Publishing, Tokyo, Japan (1976).
20. G. Kunkel, Plants for Human Consumption. Koeltz Scientific Books, Koenlgsten, Germany (1984).
21. R.N. Chopra, S.L. Nayar and I.C. Chopra, Glossary of Indian Medicinal Plants (Including the Supplement). Council of Scientific and Industrial Research, New Delhi. (1986).
22. K.H. Rechinger, Flora lranlca, Cruclferae, No. 57, Akademische Druck und Verlagsanstalt, Austria (1968).
23. O. Polunin, and A. Stainton, Flowers of the Himalayas. Oxford University Press. New Dehll (1984).
24. V.L. Komarov, Flora of the USSR. Israel Program for Scientific Translation. Jerusalem, Israel (1968).
25. C.I. Wu and P.M. Raven, FloraofChlna.VoLB, p 26, SciencePress, Missouri Botanical Garden, St. Louis, MO (1994).
26. S.A. Malsonneuve, European Pharmacopoeia. Vol. 3, pp 68-80, SainteRuffine, France (1975).
27. T. Shibamoto, Retention Indices In essential oil analysis. In: Capillary Gas Chromatography In essential oil analysis. Edits P. Sandra and C. Blcchi, pp 259-274, Huethlg Verlag, NY (1987).
28. M.D. Auria, G. Maurlello and R. Racioppi, SPME-GC/MS analysis of Horseradish (Armorcia rustlcanaj. ltal. J. Food ScI., 16,487-490 (2004).
29. J.A. Duke, Handbook of phytochemlcal constituents of GRAS herbs and other economic plants. CRC press, Boca Raton, FL (1992).
30. P.M. List, and L. Horhammer, Hagefs Handbuch der Pharmazeutischen Praxis, 6, Springer-Verlag, Berlin (1979).
31. H.Wagnerand N.R. Farnsworth, Economic and medicinal plant research. Vol. 6, p. 265, U. S. edition, Academic Press Inc., San Diego, CA (1994).
Javad Safaei-Ghomi,* Abdolhamid Bamoniri and Alireza Hatami
The Essential oil Research Center, University ofKashan, 51167 Kashan, I. R. Iran, Fax: +983615552935,
E-Mail: [email protected]
Isfahan Research Center of Natural Sources, Kashan Station, Kashan, I. R. Iran
* Address for correspondence
Received: December 2005
Revised: May 2006
Accepted: May 2006
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