بررسی و مقایسه ترکیبات شیمیایی اسانس عصاره سه گونه از گیاه دارویی Benth. Phlomis olivieri ، Phlomis persica Boiss. و Phlomis herba-venti جمع‌آوری شده از شمال غرب ایران
محورهای موضوعی : گیاهان دارویی
1 - دانشیار، گروه علوم باغبانی، دانشکده کشاورزی، دانشگاه ارومیه، ارومیه، تهران
2 - دانشجوی کارشناسی‌ارشد، گروه علوم باغبانی، دانشکده کشاورزی، دانشگاه ارومیه، ارومیه، تهران
کلید واژه: اسانس, آنتی‌اکسیدان, فنل, فلاونوئید, شمال غرب, دی‌اکتیل‌فتالات, گوش‌بره,
چکیده مقاله :
گونه‌های مختلف گوش‌بره (Phlomis sp.) به‌دلیل داشتن ترکیبات ترپنوییدی و فلاونوئیدی ضدالتهاب و آنتی اکسیدان در اسانس حائز اهمیت می‌باشند. در این مطالعه اندامهای هوایی گلدار سه گونه از گوش‌برهolivieri Benth. Phlomis،Phlomis persica Boiss. و Phlomis herba-venti در خرداد ماه 1396 از رویشگاه‌های طبیعی واقع در آذرشهر (1671 متری)، ارومیه (1598 متر) و تویسرکان (354 متری) جمع‌آوری گردید . ترکیبات اسانس و برخی خصوصیات فیتوشیمیایی عصاره ها مورد ارزیابی قرار گرفت. اسانس‌گیری به روش تقطیر با آب (طرح کلونجر) و آنالیز اسانس توسط دستگاه GC و GC-MS صورت پذیرفت. عصاره‌گیری با استفاده از دستگاه التراسونیک انجام و شاخص‌های فیتوشیمیایی بر‌‌اساس محتوای فنل کل (روش فولین سیکاتیو)، فلاونوئید کل (روش آلومینیوم کلراید) و فعالیت آنتی‌اکسیدانی (DPPH[1]) ارزیابی شدند. تعداد 38 ترکیب در اسانس سه گونه گیاه شناسایی شد که ترکیبات اصلی گونهolivieri Ph. شامل دی‌اکتیل‌فتالات (71/69 درصد)، گاما-المن (93/7 درصد) و ژرماکرون-دی (44/7 درصد) بودند و دیگر ترکیبات: نپتالاکتون (24/45 درصد)، بیس (2-اتیل هگزیل) فتالات (72/32 درصد) و ژرماکرون-دی (59/5 درصد) اجزای اصلی اسانس گونه Ph. herba-venti، معرفی شدند. همچنین در اسانس گونهPh. persica، دی‌اکتیل‌فتالات (74/49 درصد)، آلفا-مورولن (18/16 درصد) و هگزا‌هیدرو‌فارنسیل‌استون (82/7 درصد) عمده‌ترین ترکیبات را شامل شدند. مقایسه ترکیبات شناسایی شده در اسانس سه گونه نشان‌دهنده درصد بالاتر ترکیب دی‌اکتیل‌فتالات در Ph. olivieri (71/69 درصد)، نسبت به دو گونه دیگر بود. بالاترین میزان فنل کل (34/136 میلی‌گرم گالیک‌اسید بر گرم وزن خشک)، فلاونوئید کل (29/49 میلی‌گرم کوئرسیتین بر وزن خشک) و فعالیت آنتی‌اکسیدانی (68/48 درصد) مربوط به گونه Ph. Persica بود.
چکیده انگلیسی:
Different species of Phlomis are important for terpenoid compounds and anti-inflammatory and antioxidant flavonoids in their essential oils. In the present study, three species of Phlomis including Ph. olivieri Benth, Ph. persica Boiss, and Ph. herba-venti were collected from the natural habitats located in Azarshahr (elevation 1671 m), Urmia (elev. 1598 m) and Tuyserkan (elev. 1598 m) at the full-flowering stage in June 2017. Then, their essential oil constituents and some phytochemical properties the extracts were evaluated. The essential oils were extracted by the hydro-distillation method (Clevenger apparatus). CG and CG-MS were used to analyze chemical constituents. Extraction was performed using an ultrasonic device and phytochemical indices were evaluated in terms of total phenol content, total flavonoid, and antioxidant activity (%DPPH). A total of 38 compounds were identified in the essential oils of three plant species, which among them, Diisooctyl phthalate (69.71%), γ-Elemene (7.93%), and Germacrene D (7.44%) in Phlomis olivieri Benth. and Nepetalactone (45.24%), Bis (2-ethylhexyl) phthalate (32.72%), and Germacrene D (5.59%) in Phlomis herba-venti were the main compounds. Diisooctyl phthalate (49.74%), t-muurolol (16.18%) and Hexahydrofarnesyl acetone (7.82%) were identified as major compounds of Ph. persica Boiss. Comparison of identified compounds among the three species showed a higher percentage of Diisooctyl phthalate (69.71%) in Ph. Olivieri. Also, the highest amount of total phenol (136.34 GAE/g DW), total flavonoid (49.29 mg Qu. g-1 DW) and antioxidant activity (68.48%) were related to Plomis persica Boiss.
منابع و مأخذ:
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Aghakhany Kaji, F. 2016. Biosystemati study of phlomis (Lamiaceae) in Iran using morphology and flavonoid markers. fulfillment of the requirements for the degree of Master of Science in plant systematic entitled, 72-76.
Akerstrom, A., Jaakola, L., Bang, U. and Jaderlund, A. 2010. Effects of latitude- related factors and geographical origin on anthocyanidin concentrations in fruits of Vaccinium myrtillus Journal of Agricultural and Food Chemistry, 58(23): 11939-11945.
Akramian, M., Hadian, J., Joharchi, M.R., Asghari, B. and Mumivand, H. 2010. Volatile constituents of Phlomis elliptica a rare plant endemic to Iran. Journal of Essential Oil Bearing Plants, 13(6): 747-752.
Amor, I.L.B., Boubaker, J., Sgaier, M.B., Skandrani, I., Bhouri, W., Neffati, A., Kilani, S., Bouhlel, I., Ghedira, K. and Chekir-Ghedira, L. 2009. Phytochemistry and biological activities of Phlomis Journal of ethnopharmacology, 125(2): 183-202.
Asgarpanah, J. and Mohammadi Motamed, S. 2013. A review on phytochemistry and pharmacology of Otostegia persica (Burm. f.) Boiss. Quarterly Journal of Medicinal Plants, 3(47) 8-18.
Bajalan, I., Rouzbahani, R., Pirbalouti, A.G. and Maggi, F. 2017. Variation in chemical composition and antibacterial activity of the essential oil of wild populations of Phlomis olivieri. Chemistry and biodiversity, 14(5): e1600444.
Baranska, M., Schulz, H., Kruger, H. and Quilitzsch, R. 2005. Chemotaxonomy of aromatic plants of the genus Origanum via vibrational spectroscopy. Analytical and bioanalytical chemistry, 381(6): 1241-1247.
Cao, X.L. 2010. Phthalate esters in foods: sources, occurrence, and analytical methods. Comprehensive reviews in food science and food safety, 9(1): 21-43.
Carvalho, I.S., Cavaco, T., Carvalho, L.M. and Duque, P. 2010. Effect of photoperiod on flavonoid pathway activity in sweet potato (Ipomoea batatas (L. Lam.) leaves. Food chemistry, 118(2): 384-390.
Chalchat, J. and Pasquier, B. 1998. Morphological and chemical studies of Origanum clones: Origanum vulgare ssp. vulgare. Journal of Essential Oil Research, 10(2): 119-125.
Chan, K.W., Iqbal, S., Khong, N.M. and Babji, A.S. 2011. Preparation of deodorized antioxidant rich extracts from 15 selected spices through optimized aqueous extraction. Journal of Medicinal Plants Research, 5(25): 6067-6075.
Chang, Q., Zuo, Z., Harrison, F. and Chow, M.S.S. 2002. Hawthorn, Int. Journal of Clinical Pharmacy and Therapeutics, 42(6): 605–612.
Ebrahimzadeh, M.A., Hosseinimehr, S.J., Hamidinia, A. and Jafari, M. 2008. Antioxidant and free radical scavenging activity of Feijoa sallowiana fruits peel and leaves. Journal of Pharmacol-online, 1: 7-14.
Eghdami, A., Sadeghi, F., Asli, D.E. and Houshmandfar, A. 2011. Antioxidant activity of methanolic and aqueous extract of Stachys Inflata. Advances in Environmental Biology, 5: 1256-1259.
El-Beltagi, H., Ahmed, O.K. and El-Desouky, W. 2011. Effect of low dose gamma radiation on oxidative stress and secondary metabolites production of Rosemary (Rosmarinum officinalis) callus culture. Radiation Physics and chemistry, 80(9): 968-976.
Fini, A., Brunetti, C., Ferdinande, M., Ferrini, F. and Tattini, M. 2011. Stress-induced flavonoid biosynthesis and the antioxidant machinery of plant. Plant Signaling and Behavior, 6(5): 709-711.
Gogere, G., Turkyolu, U., Gursen, EN., YUR, S., Karaduman, A.B., Goger, F., Tekin, M., Özek, O. 2021. Phytochemical characterisation of Phlomis linearis & Bal and screening for anticholinesterase, antiamylase, antimicrobial and cytotoxic properties. Turk. J. Chem. 45(2): 387–399.
Ghasemi Pirbalouti, A. 2008. Medicinal and aromatic plants (identifying and studying their effects). Shahrekord Branch, Islamic Azad University Press, 541 p.
Heydari, F., Ghafarzadegan, R., Mofasseri, M., Ghasemi, S.V., Kashefi, M., Hajiaghaee, R., and Tavakoli, S. 2021. Phytochemical analysis and biological activities of essential oil and extract of Phlomis rigida J. Med. Plants. 20 (80): 13-22.
Hemmati Hassan Gavyar, P. and Amiri, H. 2018. Chemical composition of essential oil and antioxidant activity of leaves and stems of Phlomis lurestanica. International Journal of Food Properties, 21(1): 1414-1422.
Jaakola, L. and Hohtola, A. 2010. Effect of latitude on flavonoid biosynthesis in plants. Plant cell and environment, 33(8): 1239-1247.
Jabeen, B., Riaz, N., Saleem, M., Naveed, M.A., Ashraf, M., Alam, U., Rafiq, H.M., Tareen, R.B. and Jabbar, A. 2013. Isolation of natural compounds from Phlomis stewartii showing
α-glucosidase inhibitory activity. Phytochemistry, 96: 443-448.
Jamzad, Z. 2012. Lamiaceae. In Flora of Iran, Vol. 76. RIFR: Tehran; 152–251 p.
Kalinova, J. and Vrchotova, N. 2011. The influence of organic and conventional crop management, variety and year on the yield and flavonoid level in common buckwheat groats. Food Chemistry, 127(2): 602-608.
Khanavi, M., Mannan Hajimahmoodi, M., Cheraghi-Niroomand, M., Kargar, Z., Ajani, Y., Hadjiakhoondi, A. and Oveisi, M.R., 2009. Comparison of the antioxidant activity and total phenolic contents in some Stachys African Journal of Biotechnology, 8(6):1143-1147.
Ko, M.J., Lee, J.H., Nam, H.H. and Chung, M.S. 2017. Subcritical water extraction of phytochemicals from Phlomis umbrosa Innovative Food Science and Emerging Technologies, 42: 1-7.
Li, H., Chen, B. and Yao, S. 2005. Application of ultrasonic technique for extracting chlorogenic acid from Eucommia ulmodies (E. ulmodies). Ultrasonics Sonochemistry, 12(4): 295–300.
Li, M.X., Shang, X.F., Jia, Z.P. and Zhang, R.X. 2010. Phytochemical and biological studies of plants from the genus Phlomis. Chemistry and Biodiversity, 7(2): 283-301.
Mavar-Manga, H., Haddad, M., Pieters, L., Baccelli, C., Penge, A. and Quetin-Leclercq, J. 2008. Anti-inflammatory compounds from leaves and root bark of Alchornea cordifolia (Schumach. & Thonn.) Mull. Arg. Journal of ethnopharmacology, 115(1): 25-29.
Mockute, D., Bernotiene, G. and Judzentiene, A. 2003. The β-ocimene chemotype of essential oils of the inflorescences and the leaves with stems from Origanum vulgare vulgare growing wild in Lithuania. Biochemical systematics and ecology, 31(3): 269-278.
Mohammadifar, F., Delnavazi, M.R. and Yassa, N. 2015. Chemical analysis and toxicity screening of Phlomis olivieri and Phlomis persica Boiss. essential oils. Pharmaceutical Sciences, 21(1): 12.
Morteza‐Semnani, K., Azadbakht, M. and Goodarzi, A. 2004. The essential oils composition of Phlomis herba‐venti leaves and flowers of Iranian origin. Flavour and fragrance journal, 19(1): 29-31.
Nakajima, J.I., Tanaka, I., Seo, S., Yamazaki, M. and Saito, K. 2004. LC/PDA/ESI-MS profiling and radical scavenging activity of anthocyanins in various berries. Journal of BioMed Research International, 5: 241-247.
Nikan, M., Saeidnia, S., Manayi, A. and Saadatmand, S., 2017. Essential oils of four Phlomis species growing in Iran: chemical composition, antimicrobial and antifungal activity. Progress in Nutrition, 19(1): 75-79.
Ogunlesi, M., Okiei, W., Ofor, E. and Osibote, A.E. 2009. Analysis of the essential oil from the dried leaves of Euphorbia hirta Linn (Euphorbiaceae), a potential medication for asthma. African Journal of Biotechnology, 8(24).
Okoye, F.B., Obonga, W.O., Onyegbule, F.A., Ndu, O.O. and Ihekwereme, C.P., 2014. Chemical composition and anti-inflammatory activity of essential oils from the leaves of Ocimum basilicum and Ocimum gratissimum L. (Lamiaceae). International Journal of Pharmaceutical Sciences and Research, 5(6): 2174.
Omidbaigi, R. 2014. Production and Processing of Medicinal Plants. Quds Razavi Publishing House, 1(7): 348 p.
Omidbaigi, R. 2014. Production and Processing of Medicinal Plants. Quds Razavi Publishing House, 3(7): 400 p.
Ozdemir, F.A., Kilic, O. and Yildirimli, S. 2017. Essential oil composition and antimicrobial activity of endemic Phlomis sieheana from Bingol (Turkey). Journal of Essential Oil Bearing Plants, 20(2): 516-523.
Raman, V., La, S., Saradhi, P., Rao, N., Krishna, N.V., Sudhakar, M. and Radhakrishnan T.M. 2012. Antibacterial, antioxidant activity and GC-MS analysis of Eupatorium odoratum. Asian Journal of Pharmaceutical and Clinical Research, 5(2): 99-106.
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α-glucosidase inhibitory activity. Phytochemistry, 96: 443-448.