Effect of different distillation methods on quantity and quality of essential oil of two Ziziphora L. species
محورهای موضوعی : مجله گیاهان داروییحسین بتولی 1 , مریم اخباری 2 , سید محمد جواد حسینی‌زاده 3
1 - مرکز تحقیقات کشاورزی و منابع طبیعی استان اصفهان (باغ گیاه‌شناسی کاشان)، کاشان، ایران؛
2 - پژوهشکده اسانس‌های طبیعی دانشگاه کاشان)، کاشان، ایران؛
3 - پژوهشکده اسانس‌های طبیعی دانشگاه کاشان)، کاشان، ایران؛
کلید واژه: lamiaceae, Ziziphora, Essential oil, Aromatic plants, Pulegon,
چکیده مقاله :
Background & Aim: Ziziphora L. genus belongs to the Lamiaceae family, which has important medicinal and aromatic plant species. In current study, essential oil chemical compositions of two Ziziphora L. species (Z. tenuior L. and Z. clinopodioides Lam.) were investigated. Experimental: The flowering branches of Z. tenuior and Z. clinopodioides were collected in spring and summer 2011. The aerial parts dried in shade at room temperature. The flowering branches of these species subjected to volatile fraction were isolated by simultaneous distillation extraction (SDE), hydro distillation (using a Clevenger-type apparatus), steam-cooled distillation (ultrasonic) and steam distillation. The analysis of the oils was performed by using GC and GC-MS. Results & Discussion: The results indicated the essential oil yield of Z. tenuior ranged 0.2% to 2.3% (w/w), and Z. clinopodioides ranged 0.3% to 1.3% (w/w(. In total, 18 components were identified in Z. tenuior essential oil, and 33 components were identified in Z. clinopodioides essential oil. The main components of Z. tenuior essential oil were pulegon (80.01% - 90.10%), and piperitenone (4.5% - 7.14%). The major compounds in Z. clinopodioides essential oil were pulegon (25.87% - 35.20%), piperitenone (10.11% - 27.88%), menthol (11.41%-17.50%), and menthon (0 - 7.69%). The highest percentage of menthol in essential oil in two species obtained from SDE method. Industrial and practical recommendations: According to the purity 81% of pulegon combination in essential oil of Ziziphora with 2% essential oil yield, can be purified in production of Ziziphora.
مقدمه و هدف: جنس "کاکوتی"(Ziziphora L.) متعلق به خانواده نعناعیان(Lamiaceae)، دارای گونههای داروئی و معطره بسیار ارزشمندی است که تاکنون بالغ بر 25 گونه از این جنس در جهان و 4 گونه یک ساله و چند ساله از ایران گزارش شده است. در این تحقیق ترکیب‌های شیمیائی اسانس دو گونهی کاکوتی(Z. tenuior L.، Z. clinopodioides Lam.) منطقه قمصر کاشان مورد بررسی قرار گرفته است. روش تحقیق: سرشاخه‌های گل‌دار گونههای مذکور در بهار سال 1390 جمع‌آوری و به روش های مختلف شامل تقطیر و استخراج با بخار همزمان با حلال آلی (SDE)، کلونجر، اسانسگیری با بخار سرد (با استفاده از امواج فراصوت) و تقطیر با بخار آب اسانسگیری شدند. برای شناسائی ترکیب‌های تشکیل‌دهنده اسانس، از دستگاه‌های گاز کروماتوگرافی(GC) و گاز کروماتوگرافی متصل شده به طیف‌سنج جرمی(GC/MS) استفاده شد. نتایج و بحث: عملکرد اسانس در روش‌های مختلف، در گیاه کاکوتی یا Z. tenuior بین 2/0 تا 3/2% و در گیاه کاکوتی کوهی یا Z. clinopodioides بین 3/0 تا 3/1% متغییر بود. 18 ترکیب شیمیائی در اسانس سرشاخه‌های گل‌دار گیاه کاکوتی و 33 ترکیب در اسانس گیاه کاکوتیکوهی شناسایی شدند. اجزای اصلی اسانس کاکوتی شامل پولگون (1/90%-0/80%) و پیپریتنون (1/7%-5/4%) بودند. بیشترین ترکیب‌های تشکیل‌دهنده اسانس کاکوتیکوهی شامل پولگون (2/35%-9/25)، پیپریتنون (9/27%-1/10%)، منتول(5/17%-4/11%) و منتون (7/7%-0) بودند. حضور درصد بالای منتول در اسانس گیاه کاکوتیکوهی، باعث مرغوبیت اسانس این گیاه شده است. بهترین راندمان اسانس در دو گیاه، متعلق به روش تقطیر و استخراج با بخار همزمان با حلال آلی بود. توصیه کاربردی/صنعتی: با توجه به خلوص 81 درصدی ترکیب پولگون در اسانس گیاه کاکوتی و با در نظر داشتن بازده حدوداً دو درصدی استحصال اسانس، میتوان در صورت کشت مکانیزه این گیاه، ترکیب مورد نظر را خالص سازی نمود.
Ai-long, S., Hong-ling, C. and Qing-yan, M. 2012. Anti-flammatory and antalgic effects of Ziziphora clinopodioides and its acute toxicity. Chinese Journal of Experimental Traditional Medical Formulae., 4: 202-204.
Amin, G.R. 1997. Traditional medicinal plants of Iran. Research Deputy Publications of Hygiene Ministry, Islamic Republic of Iran, pp: 230. [in Persian].
Amiri, H. 2009. Composition and antioxidant activity of the essential oil and methanolic extract of Ziziphora Clinopodioides Lam. in pre-flowering stage. Journal of Kerman University of Medical Sciences., 16(1): 79-86.
Babakhanloo, P., Mirza, M., Sefidkon, F., Barazandeh, M.M. and Asgari, F. 1998. Chemical composition of essential oil of Z. clinopodioides Lam. Iranian Medicinal Plants Research Journal., 2: 103-114..
Batooli, H. 2003. Biodiversity and species richness of plant elements in Qazaan reserve of Kashan. Pajouheh & Sazandegi., 61(4): 85-103.
Chachoyan, A.A. and Oganesyan, G.B. 1991. Antitumor activity of some spices of the family Lamiaceae. Rastitelnye Resursy., 32(4): 59-64.
Davies, N.W. 1990. Gas chromatographic retention index of monoterpenes and sesquiterpenes on methyl silicone and carbowax 20 M phases. Journal of Chromatography., 503: 1-24.
De Sousa, D.P., Junior, E.V., Oliveira, F.S., De Almeida, R.N., Nunes, X.P. and Barbosa-Filho, J.M. 2007. Antinociceptive activity of structural analogues of rotundifolone: structure-activity relationship. Z. Nature. Forsch., 62 (1-2): 39-42.
Dembitskii, A.D., Bergaliev, E.S. and Kyazimov, I.M. 1994. Chemical composition of the essential oils of Ziziphora growing under various ecological conditions. Chemistry of Natural Compounds., 30(6): 673-5.
Economou, K.D., Oreopoulou, V. and Thomopoulos, C.D. 1991. Antioxidant activity of some plant extracts of the family labiatae. Journal of the American Chemical Society., 68: 109-113.
Enghashte Vahed, A.A. 2012. Developed a new system of plant oils by Steam-Cooled distillation (Ultrasonic) through cavitation and compared with conventional methods on native plant two species of the family compositae and phytochemical and biological properties of these two plants. Master's thesis of Essential oils Research Institute, University of Kashan, Kashan pp 130. [in Persian].
Franzios, G., Maria Mirotsou, M., Hatziapostolou, E., Kral, J., Zacharias Scouras, G. and Mavragani-Tsipidou, P. 1997. Insecticidal and genotoxic activities of mint essential oils. Journal of Agricultural and Food Chemistry., 45(7): 2690-2694.
Ghasemi Pirbalouti, A. 2009. Medicinal plants used in Chaharmahal and Bakhtyari districts, Iran. Herba Polonica., 55: 69-75.
Jamzad, Z. 2009. Thymus and Saureja species of Iran. Publishing of Research Institute of Forests and Rangelands. pp: 171. [in Persian].
Karimi, H. 1995. Names of Iran plants. Nashre-Daneshgahi press. pp: 412. [in Persian].
Kguel, A., Pooter, H.D. and Buyck, L.D. 1991. The essential oil of Calamintha nepeta subsp. glandulosa and Ziziphora clinopodioides Lam. from Turkey. Journal of Essential oil Research., 3(1): 7-10.
Konyalioglu, S., Qzturk, B. and Elgin, M.G. 2006. Comparison of chemical compositions and antioxidant activities of the essential oils of two Ziziphora taxa from Anatolia. Pharmaceutical Biology., 44: 121-126.
Koocheki, A., Nassiri-Mahallati, M. and Azizi, G. 2004. The effects of water stress and defoliation on some of quantitative traits of Zataria multiflora, Ziziphora clinopodioides, Thymus vulgaris and Teucrium polium. Iranian Journal of Field Crops Research., 1-18.
Meral, G.E., Konyalioglu, S. and Ozturk, B. 2002. Essential oil composition and antioxidant activity of endemic Ziziphora taurica subsp. cleonioides. Fitoterapia., 73(7-8): 716-8.
Mirhaydar, Kh. 1996. Plant Encyclopedia (application of plants in cure of disease), vol:2, 2nd ed. Office of Islamic Farhag press. Tehran. pp: 514. [in Persian].
Mozaffarian, V. 2008. A pictorial dictionary of botany botanical taxonomy: in Latin - English - French - Germany - Persian/ Complied, Tehran, Iran, pp. 522.
Naghibi, F., Mosaddegh, M., Mohammadi Motamed, S. and Ghorbani, A. 2005. Labiatae family in folk medicine in Iran from ethnobotany to pharmacology. Iranian Journal of Pharmaceutical Research., 2: 63-79.
Najafi, F. and Tavakkoli, Z. 2011. Comparing essential oil composition and antibacterial effects of Ziziphora tenuior L. in two regions of Iran. Iranian Journal of Medicinal and Aromatic Plants., 27(2): 239-248.
Ozturk, S. and Ercisli, S. 2007. Antibacterial activity and chemical constitutions of Ziziphora clinopodioides. Food Control., 18(5): 535-540.
Palacios, S.M., Bertoni, A., Rossi, Y., Santander, R. and Urzúa, A. 2009. Insecticidal activity of essential oils from native medicinal plants of Central Argentina against the house fly; Musca domestica (L.). Parasitology Research., 106(1): 207-212.
Rechninger, K.H. 1982. Ziziphora (Labiatae) in Flora Iranica. Akademische Druck-U, Verlagsanstalt, Graz-Austria. 150: 480-493.
Sajjadi, S.E., Ghasemi Dehkordi, N. and Baluchi, M. 2003. Volatile constituents of Ziziphora clinopodioides Lam. Pajoohesh & Sazandeghi., 58(1): 97-100.
Salehi, P., Sonboli, A., Eftekhar, F., Nejad-Ebrahimi, S. and Yousefzadi, M. 2005. Essential oil composition, antibacterial and antioxidant activity of the oil and various extracts of Ziziphora clinopodioides subsp. rigida (Boiss.) Rech. f. from Iran. Biological & Pharmaceutical Bulletin., 28(10): 1892-6.
Scavroni, J., Boaro, C.S.F., Marques, M.O.M. and Ferreira, L.C. 2005. Yield and composition of the essential oil of Mentha piperita L. (Lamiaceae) grown with biosolid. Brazilian Journal of Plant Physiology., 17(4): 345-352.
Sezik, E., Tumen, G. and Baser, K.H. 2006. Ziziphora tenuior L., a new source of pulegone. Flavour Fragrance Journal., 6(1): 101-103.
Shafei, M., Sharifan, A., Aghazade Meshki, M. 2012. Composition of essential oil of Ziziphora clinopodioides and its antimicrobial activity on Kluyveromyces marxianus. Food Technology & Nutrition., 9(1): 101-108.
Sharopov, F.S. and Setzer, W.N. 2011. Chemical diversity of Ziziphora clinopodioides: composition of the essential oil of Z. clinopodioides from Tajikistan. Natural Product Communications., 6(5): 695-698.
Shibamoto, T. 1987. Retention indices in essential oil analysis: 259-274. In: Sndra, P. and Bicchi, C., (Eds.). Capillary Gas Chromatography in Essential Oil Analysis. Verlagsgruppe Huthig Jehle Rehm GmbH, New York. 435 pp.
Sigma Aldrich. 2012. (S)-(−)-Pulegone. http://www.sigmaaldrich.com/catalog/product/aldrich/328847?lang=en®ion=IR.
Si-lei, X., Pi-hong, Z., Qiao-ling, J.I., Hong-li, J. and Xue-hua, W. 2011. Essential oil compositions and antioxidant activities of two Ziziphora species in Xinjiang. Food Science., 6 (5): 695-698.
SLS. 2012. (r)-(+)-pulegon 85+%. http://www.scientificlabs.co.uk/product/W296309-100G.
Soltani Nejad, S. 2012. Chemical composition and in vitro antibacterial activity of Ziziphora clinopodioides Lam. essential oil against some pathogenic bacteria. African Journal of Microbiology Research., 6(7): 1504-1508.
Sonboli, A., Atri M. and Shafiei, S. 2010. Intraspecific variability of the essential oil of Ziziphora clinopodioides ssp. rigida from Iran. Chemistry & Biodiversity., 7(7) :1784-9.
Sonboli, A., Mirjalili, M.H., Hadian, J., Nejad Ebrahimi, S. and Yousefzadi, M. 2006. Antibacterial activity and composition of the essential oil of Ziziphora clinopodioides subsp. bungeana (Juz.) Rech. f. from Iran. Z. Naturforsch., 61(9-10): 677-80.
Talebi, S.M., Ebrahimi, J. and Mansouri, M. 2010. The phenotypic plasticity in variant population of Ziziphora tenuior L. (Labiatae). Ghiah va Zistboom., 22: 3-17. [in Persian].
Tian, S., Shi, Y., Zhou, X., Ge, L. and Upur, H. 2011. Total polyphenolic (flavonoids) content and antioxidant capacity of different Ziziphora clinopodioides Lam. Extracts. Pharmacognosy Magazine., 7(25): 65-68.
Tumen, G. and Ayhan, Z. 1992. Antimicrobial activity of essential oils of two Ziziphora species growing in Turkey. Fitoterapia., 63: 264-265.
Usher, G. 1971. A dictionary of plants. CBS Publishers and distributors, Dlhi India. pp. 619.
Yao, Q.S. and Chiou, G.C. 1993. Inhibition of crystallins-induced inflammation in rabbit eyes with five phytogenic compounds. Zhongguo Yao Li Xue Bao., 14(1):13-7.
Zarabi, M. 2000. Pharmacognosical evaluation of Ziziphora. (Pharm D. Thesis), Faculty of Pharmacy: University of Tehran, [in Persian].
Zargari, A. 1993. Medicinal plants. Tehran University Publications, pp: 696. [in Persian].
Zhong-lei, L., Jin-rong, L., Heng, W., Hang-yu, W., Fang-qun, L. and Wen-xia, L. 2008. composition analysis for the essential oil of Ziziphora clinopodioides Lam. Journal of Shihezi University (Natural Science)., 4: 483-486.
