Fatty Acid Composition of Juniperus Species ( Juniperus Section) Native to Turkey

Abstract

Fatty acid compositions of seeds of five taxa of the Juniperus section of the genus Juniperus L. (Cupressaceae), i. e. J. drupacea Lab., J. communis L. var. communis, J. communis var. saxatilis Pall., J. oxycedrus L. subsp. oxycedrus, and J. oxycedrus subsp. macrocarpa (Sibth. & Sm.) Ball, were investigated. Methyl ester derivatized fatty acids of the lipophylic extracts of the five species were comparatively analyzed by capillary gas chromatography-mass spectrometry (GC-MS). Juniperus taxa showed uniform fatty acid patterns, among which linoleic (25.8–32.5%), pinolenic (11.9–24.1%) and oleic acids (12.4–17.2%) were determined to be the main fractions in the seed oils. Juniperonic acid was found to be remarkably high in J. communis var. saxatilis (11.4 %), J. oxycedrus subsp. oxycedrus (10.4 %), and J. communis var. communis (10.1 %). To the best of our knowledge, the present work discloses the first report on the fatty acid compositions of seeds of this Juniperus section grown in Turkey.

Keywords

Cupressaceae Juniperus Juniperus drupacea Fatty acid GC-MS Seed oil

References

(a) Nakanishi

, Iida

, Inatomi

, Murata

, Inada

, Murata

, Lang

F.A.

, Iinuma

, Tanaka

(2004) Neolignan and flavonoid glycosides in Juniperus communis var. depressa. Phytochemistry, 65, 207–213;(b) Townsend CC, Guest E. (1966) Flora of Iraq. 2, Ministry of Agriculture Republic of Iraq; (c) Seca AML, Silva AMS. (2007) The chemical composition of the Juniperus genus (1970–2004). Recent Progress in Medicinal Plants Source, 16, 401–522.

(a) Coode

M.J.E.

, Cullen

(1965) Juniperus L. In Flora of Turkey and the East Aegean Islands. Vol 1, Davis

P.H.

(Ed.) Edinburgh University press, Edinburgh; (b) Farjon A. (2000) Juniperus L. In Flora of Turkey and the East Aegean Islands. Vol., 11 (Supplement), Güner A, Özhatay N, Ekim T, Başer KHC (Eds.), Edinburgh University Press, Edinburgh; (c) Baytop T. (1994) Türkçe Bitki Adlarι Sözlüğü, Atatürk Kültür, Dil ve Tarih Yüksek Kurumu, Türk Dil Kurumu Yayιnlarι: 578, Ankara.

(a) PDR for Herbal Medicines (2004) 3rd ed., Thomson Medical Economics, Montvale, NJ; (b) Yeşilada E, Honda G, Sezik E, Tabata M, Goto K, Ikeshiro Y. (1993) Traditional medicine in Turkey IV. Folk medicine in the Mediterranean subdivision. Journal of Ethnopharmacology, 39, 31–38; (c) Yeşilada E, Honda G, Sezik E, Tabata M, Fujita T, Tanaka T, Takeda Y, Takaishi Y. (1995) Traditional medicine in Turkey V. Folk medicine in the inner Taurus Mountains. Journal of Ethnopharmacology, 46, 133–152; (d) Honda G, Yeşilada E, Tabata M, Sezik E, Fujita T, Takeda Y, Takaishi Y, Tanaka T. (1996) Traditional medicine in Turkey VI. Folk medicine in West Anatolia: Afyon, Kütahya, Denizli, Muğla, Aydιn provinces. Journal of Ethnopharmacology, 53, 75–87; (e) Sezik E, Yeşilada E, Honda G, Takaishi Y, Takeda Y, Tanaka T. (2001) Traditional medicine in Turkey X. Folk medicine in Central Anatolia. Journal of Ethnopharmacology, 75, 95–115.

Chang

C.I.

, Chiy-Rong Chen

C.R.

, Chen

W.C.

, Chao-Lin Kuo

C.L.

, Yueh-Hsiung Kuo

Y.H.

(2010) A New Phenolic and a New Lignan from the Roots of Juniperus chinensis. Natural Product Communications, 5, 55–57.

(a) Boti

J.B.

, Bighelli

, Cavaleiro

, Salgueiro

, Casanova

(2006) Chemical variability of Juniperus oxycedrus ssp. oxycedrus berry and leaf oils from Corsica, analysed by combination of GC, GC-MS and ¹³C-NMR. Flavour and Fragrance Journal, 21, 268–273;(b) Ottavioli J, Casanova J, Ange Bighelli A. (2010) Composition and chemical variability of the leaf oil from Corsican Juniperus thurifera integrated analysis by GC(RI), GC-MS and ¹³C NMR. Natural Product Communications, 5, 1991–1994; (c) Martin AM, Queiroz EF, Marston A, Hostettmann K. (2006) Labdane diterpenes from Juniperus communis L. berries. Phytochemical Analysis, 17, 32–35; (d) Okasaka M, Takaishi Y, Kashiwada Y, Kodzhimatov OK, Ashurmetov O, Lin AJ, Consentino LM, Lee KH. (2006) Terpenoids from Juniperus polycarpus var. seravschanica. Phytochemistry, 65, 2635–2640; (e) Chang C, Chen WC, Shao YY, Yeh GR, Yang NS, Chiang W, Kuo YH. (2008) A new labdane-type diterpene from the bark of Juniperus chinensis Linn. Natural Product Research, 22, 1158–1162; (f) Seca AML, Silva AMS, Bazzocchi IL, Jimenaez IA. (2008) Diterpene constituents of leaves from Juniperus brevifolia. Phytochemistry, 69, 498–505; (g) Seca AML, Silva AMS. (2008) The chemical composition of hexane extract from bark of Juniperus brevifolia. Natural Product Research, 22, 975–983; (h) Topcu G, Erenler R, Cakmak O, Johansson CB, Celik C, Chai HB, Pezzuto JM. (1999) Diterpenes from the berries of Juniperus excelsa. Phytochemistry, 50, 1195–1999.

(a) Sezik

, Kocakulak

, Başer

K.H.C.

, Özek

(2005) Composition of the essential oils of Juniperus oxycedrus subsp. macrocarpa from Turkey. Chemistry of Natural Compounds, 41, 352–354;(b) Stassi V, Verykokidou E, Loukis A, Harvala C, Philianos S. (1996) The antimicrobial activity of the essential oils of four Juniperus species growing wild in Greece. Flavour and Fragrance Journal, 11, 71–74; (c) Pepeljnjak S, Kosalec I, Kalodera Z, Blazevic N. (2005) Antimicrobial activity of juniper berry essential oil (Juniperus communis L., Cupressaceae) Acta Pharmaceutica, 55, 417–422; (d) Fouad B, Abderrahmane R, Youssef A, Rajae H, and M. Alaoui El Fels, MAE. (2011) Chemical composition and antibacterial activity of the essential oil of Moroccan Juniperus phoenicea. Natural Product Communications, 6, 1515–1518. (e) Wedge DE, Tabanca N, Sampson BJ, Werle C. Demirci B, Baser KHC, Nan P, Duan J, Liu Z. (2009) Antifungal and insecticidal activity of two Juniperus essential oils. Natural Product Communications, 4, 123–127; (f) Loizzo MR, Tundis R, Conforti F, Saab AM, Statti GA, Menichini F. (2007) Comparative chemical composition, antioxidant and hypogycaemic activities of Juniperus oxycedrus ssp. oxycedrus L. berry and wood oils from Lebanon. Food Chemistry, 105, 572–578.

Schepetkin

I.A.

, Faulkner

C.L.

, Nelson-Overton

L.K.

, Wiley

J.A.

, Quinn

M.T.

(2005) Macrophage immunomodulatory activity of polysaccarides isolated from Juniperus scopolorum. International Immunopharmacology, 5, 1783–1799.

(a) Fujita

, Yoshikawa

(1951) Plant wax. I. Constituents of the wax of Juniperus rigida. Yakugaku Zasshi, 71, 913–916; (b) Mongrand S, Badoc A, Patouille B, Lacomblez C, Chavent M, Cassagne C, Bessoule J-J. (2001) Taxonomy of gymnospermae: multivariate analyses of leaf fatty acid composition. Phytochemistry, 58, 101–115.

(a) Topcu

, Goren

A.C.

, Bilsel

, çakmak

(2005) Constituents of bioactive essential oil of the berries and leaves of Juniperus excelsa. Pharmaceutical Biology 43, 125–128; (b) Nuñez YO, Iraida IS, Collado IG, Hernández-Galán R. (2008) Screening study of potential lead compounds for natural product based fungicides from Juniperus lucayana. Natural Product Communications, 3, 469–473.

10.

(a) Commission E Monographs: The Complete German Commission E Monographs: Therapeutic Guide to Herbal Medicines. (1998) 1st ed., Blumenthal

, Busse

W.R.

(Eds.), American Botanical Council, Lippincott Williams & Wilkins, Austin TX; (b) European Pharmacopoeia. (2008) 6th ed., Vol 2, Council of Europe, Strasbourg.

11.

Akιncι

, Özdemir

, Topuz

, Kabaş

, çanakçι

(2004) Some physical and nutritional properties of Juniperus drupacea fruits. Journal of Food Engineering, 65, 325–331.

12.

(a) O'Brien

R.D.

(2009) Fats and oils. Formulating and processing for applications. 3th ed. CRC Press, Taylor & Francis Group; (b) Tapiero H, Nguyen Ba G, Couvreur P, Tew KD. (2002) Polyunsaturated fatty acids (PUFA) and eicosanoids in human health and pathologies. Biomedicine & Pharmacotherapy, 56, 215–222.

13.

(a) Eckey

E.W.

, Miller

L.P.

(1954) Vegetable fats and oils. American Chemical Society Monograph Series, Book Division, Reinhold Publishing Corporation, New York; (b) Hegnauer R. (1962) Chemotaxonomie der pflanzen. Band 1, Birkhauser Verlag, Basel; (c) Wolf RL, Lavialle O, Pédrono F, Pasquier E, Deluc LG, Marpeau AM, Aitzetmüller K. (2001) Fatty acid composition of Pinaceae as taxonomic markers. Lipids, 36, 439–451.

14.

(a) Association of Official Analytical Chemists. (1980) Official Methods of Analysis, 14th ed., Washington, DC; (b) Erdemoğlu N, Akalιn E, Akgöç M, çιkrιkçι S, Bilsel G. (2008) Comparison of the seed oils of Ferulago trachycarpa Boiss. different localities with respect to fatty acids. Records of Natural Products, 2, 13–18.