(مقاله کوتاه علمی) استخراج، جداسازی و تعیین ساختار شیمیایی گلیکوزید قلبی دیگوکسین از عصارۀ گیاهLeonurus cardiaca L.
محورهای موضوعی :
فیتوشیمی
محبوبه طاهرخانی
1
(استادیار، دانشگاه آزاد اسلامی واحد تاکستان، دانشکده علوم پایه، گروه شیمی، تاکستان، ایران)
شبنم ارجمندی
2
(دانشجوی کارشناسی ارشد، گروه آموزشی فیتوشیمی و شیمی فناوری اسانس، دانشکده شیمی دارویی، واحد علوم دارویی دانشگاه آزاد اسلامی، تهران، ایران)
مجید قربانی نهوجی
3
(هیات علمی مرکز تحقیقات گیاهان دارویی، پژوهشکده گیاهان دارویی جهاد دانشگاهی)
تاریخ دریافت : 1396/10/10
تاریخ پذیرش : 1397/11/14
تاریخ انتشار : 1398/09/01
کلید واژه:
ایران,
کروماتوگرافی ستونی,
گلیکوزید قلبی,
گیاه دم شیر,
منبع جدید دیگوکسین,
چکیده مقاله :
گیاه دارویی دم شیر با نام علمی Leonurus cardiaca L. گیاهی علفی و چند ساله متعلق به تیرۀ نعنائیان (Lamiaceae) است که بطور گسترده ای در طب سنتی ایران و دیگر کشورها به عنوان گیاهی آرام بخش، خواب آور، مدر، کاهنده فشار خون و بویژه به عنوان درمان بیماری‌های قلبی شناخته می‌شود. از این گیاه ترکیبات فیتوشیمیایی مهمی نظیر آلکالوییدها، ایریدوییدها، ساپونین‌ها، فلاونوییدها، کاردنولیدها و دی ترپنوییدها استخراج و شناسایی شده است. با توجه به اهمیت و پراکندگی این گیاه در ایران، هدف از این پژوهش بررسی فیتوشیمیایی عصارۀ گیاهL. cardiaca در جهت ارزیابی و شناسایی ترکیبات طبیعی موجود در آن می‌باشد. در راستای این تحقیق، ابتدا اندام‌های هوایی گیاه مذکور در مرحلۀ گلدهی از دامنه‌های کوه دماوند در مردادماه 1395 جمع آوری و به روش خیساندن در حلال عصاره گیری گردید. سپس به منظور جداسازی چربی‌ها و ترکیبات اشباع با زنجیره‌های بلند، عمل چربی‌گیری توسط حلال هگزان و در قیف جداکننده انجام شد. در مرحله بعد به منظور جداسازی فراکسیون‌های مختلف، بر روی ستون کروماتوگرافی برده و نهایتاً از میان 32 فراکسیون بدست آمده، از فراکسیون 8+9+10 بلور مربوط به ترکیبی طبیعی ظاهر گردید. برای اولین بار در دنیا از گیاه دم شیر ترکیب طبیعی یک گلیکوزید قلبی با نام دیگوکسین استخراج، جداسازی و خالص سازی شده و با استفاده از روش‌های طیف سنجی 13C-NMR، 1H-NMR، DEPT و IR ساختمان شیمیایی آن شناسایی و معرفی گردید.
چکیده انگلیسی:
The Leonurus cardiaca L. is a perennial herbaceous medicinal plant. This species belongs to Lamiaceae family and commonly known as “lion's tail” in Persian. L. cardiaca is widely used in Iranian traditional medicine and others as sedative, hypnotic, diuretic and blood pressure reducer agent. This species is using in remedy of heart diseases. Many important phytochemical compounds such as alkaloid, iridoid, saponins, flavonoids, carotenoids and diterpenoids have been previously extracted and identified from L. cardiaca. Regarding the importance of plant and also presence in the Country, this study was defined to investigate the phytochemical constituents of L. cardiaca extract in order to evaluate and identify of natural compounds. Hence the aerial parts of plant were collected from natural habitat in hillsides of Damavand Mountain (Mazandaran Province) in flowering growth stage. The shade dried materials were powdered and then were extracted using maceration method. The extract was defatted using Hexane solvent in next step. Chromatography column was used for fractionation of extract and 32 different fractions were isolated as the result. A natural compound's crystal was appeared in fraction 8+9+10 and so its chemical structure was evaluated using spectro-photometric methods (1H-NMR,13C-NMR, IR and DEPT Techniques). Based on the obtained spectra, natural compound of Digoxin (a well-known cardiac glycoside from other plant species) was extracted, purified and identified from L. cardiaca extract for the first time in the world.
منابع و مأخذ:
References
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Blumenthal, M., Goldberg, A. and Brinckmann, J. 2000. Herbal medicine expanded commission e monographs. Integrative Medicine Communication. American Botanical Council: Austin, Texas, 267 p.
Bol’shakova, I.V., Losovskaia, E.L., Sapezhinskii, I.I. 1997. Photosensitizing
and photoprotective properties of extracts from groups of medicinal plants. Biofizika, 42(4): 926-932.
Bradley, P.R. 1992. British Herbal Compendium (Vol. 1). British Herbal Medicine Association: Bournemouth, 161p.
Brieskorn, C.H. and Hofmann, R. 1979. Bitter substances from labiate plants: a clerodane derivative from Leonurus cardiac. Tetrahedron Letters, 20(27): 2511-2512.
Calderon-Montano, J.M., Burgos-Moron, E., Luis Orta, M., Maldonado-Navas, D., Garcia-Dominguez, I. and Lopez-Lazaro, M. 2014. Evaluating the cancer therapeutic potential of cardiac glycosides. BioMed Research International, Article ID 794930. 9 p.
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Chen, Z.S., Chen, C.X. and Kwan, C.Y. 2000. Leonurine, an alkaloid from Leonurus artemesia, induces contraction in mouse uterine smooth muscle but relaxation in vascular smooth muscle of rat portal vein. Biomedical Research, 11(2): 209-212.
Ewy, G.A. 2015. Digoxin: The Art and Science. The American Journal of Medicine, 128(12): 1272-1274.
Feng, Y., Lu, Y., Liu, D., Zhang, W., Liu, J., Tang, H. and Zhu, Y. 2017. Apigenin-7-O-β-d-(-6″-p-coumaroyl)-glucopyranoside pretreatment attenuates myocardial ischemia/reperfusion injury via activating AMPK signaling. Life Sciences, 15(203): 246-254.
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Flemmig, J., Noetzel, I., Arnhold, J. and Rauwald, H.W. 2015. Leonurus cardiaca L. herb extracts and their constituents promote lactoperoxidase activity. Journal of Functional Foods, 17: 328-339.
Gulubov, A. and Chervenkova, V. 1970. Structure of alkaloids from Leonurus cardiaca. Materialia Fizika Khimicheskaya Biologica, 8(1): 129-132.
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Janicsák, G., Veres, K., Kakasy, A.Z. and Máthé, I. 2006. Study of the oleanolic and ursolic acid contents of some species of the Lamiaceae. Biochemical Systematics and Ecology, 34(5): 392-396.
Ji, S., Fattahi, A., Raffel, N., Hoffmann, I., Beckmann, M.W., Dittrich, R. and Schrauder, M. 2017. Antioxidant effect of aqueous extract of four plants with therapeutic potential on gynecological diseases; Semen persicae, Leonurus cardiaca, Hedyotis diffusa, and Curcuma zedoaria. European Journal of Medical Research, 22(1): 1-8.
Kartnig, T., Gruber, A. and Menzinger, S. 1985. Flavonoid-O-Glycosides from the Herbs of Leonurus cardiaca. Journal of Natural Products, 48(3): 494-507.
King, R.E. and Gisvold, O. 1950. Some extraction studies on Digitalis. Journal of the American Pharmaceutical Association, 39(2): 109-112.
Mil kowska-Leyck, K., Filipek, B. and Strzelecka, H. 2002. Pharmacological effects of lavandulifolioside from Leonurus cardiaca. Journal of Ethnopharmacology, 80(1): 85-90.
Mockute, D., Bernotiene, G. and Judzentiene, A. 2006. Germacrene D chemotype of essential oils of Leonurus cardiaca L. growing wild in Vilnius district (Lithuania). Journal of Essential Oil Research, 18(5): 566-568.
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References
Agnihotri, V.K., Elsohly, H.N., Smillie, T.J., Khan, I.A. and Walker, L.A. 2008. New labdane diterpenes from Leonurus cardiaca. Planta Medica, 74(10):1288-1290.
Ali, M.S., Ibrahim, S.A., Jalil, S. and Choudhary, M.I. 2007. Ursolic acid: a potent inhibitor of superoxides produced in the cellular system. Phytotherapy Research, 21(6): 558-561.
Al-Snafi, A.E. 2017. Phytochemical constituents and medicinal properties of digitalis lanata and Digitalis purpurea- A review. Indo Americal Journal of Pharmaceutical science (IAJPS), 4(2): 225-234.
Bernatoniene, J., Kopustinskiene, D.M., Jakstas, V., Majiene, D., Baniene, R., Kuršvietiene, L., Masteikova, R., Savickas, A., Toleikis, A. and Trumbeckaite, S. 2014. The Effect of Leonurus cardiaca herb extract and some of its flavonoids on mitochondrial oxidative phosphorylation in the Heart. Planta Medica, 80(7): 525-532.
Bernatoniene, J., Kucinskaite, A., Masteikova, R., Kalveniene, Z., Kasparaviciene, G. and Savickas, A. 2009. The comparison of anti-oxidative kinetics in vitro of the fluid extract from maidenhair tree, motherwort and hawthorn. Acta Poloniae Pharmaceutica, 66(4): 415-421.
Blumenthal, M., Goldberg, A. and Brinckmann, J. 2000. Herbal medicine expanded commission e monographs. Integrative Medicine Communication. American Botanical Council: Austin, Texas, 267 p.
Bol’shakova, I.V., Losovskaia, E.L., Sapezhinskii, I.I. 1997. Photosensitizing
and photoprotective properties of extracts from groups of medicinal plants. Biofizika, 42(4): 926-932.
Bradley, P.R. 1992. British Herbal Compendium (Vol. 1). British Herbal Medicine Association: Bournemouth, 161p.
Brieskorn, C.H. and Hofmann, R. 1979. Bitter substances from labiate plants: a clerodane derivative from Leonurus cardiac. Tetrahedron Letters, 20(27): 2511-2512.
Calderon-Montano, J.M., Burgos-Moron, E., Luis Orta, M., Maldonado-Navas, D., Garcia-Dominguez, I. and Lopez-Lazaro, M. 2014. Evaluating the cancer therapeutic potential of cardiac glycosides. BioMed Research International, Article ID 794930. 9 p.
Chan, W.C., Wong, Y.C., Kong, Y.C., Chun, Y.T., Chang, H.T. and Chan, W.F. 1983. Clinical observation on the uterotonic effect of I-mu Ts’ao (Leonurus artemisia). American Journal of Clinical Medicine, 11: 77-83.
Chen, Z.S., Chen, C.X. and Kwan, C.Y. 2000. Leonurine, an alkaloid from Leonurus artemesia, induces contraction in mouse uterine smooth muscle but relaxation in vascular smooth muscle of rat portal vein. Biomedical Research, 11(2): 209-212.
Ewy, G.A. 2015. Digoxin: The Art and Science. The American Journal of Medicine, 128(12): 1272-1274.
Feng, Y., Lu, Y., Liu, D., Zhang, W., Liu, J., Tang, H. and Zhu, Y. 2017. Apigenin-7-O-β-d-(-6″-p-coumaroyl)-glucopyranoside pretreatment attenuates myocardial ischemia/reperfusion injury via activating AMPK signaling. Life Sciences, 15(203): 246-254.
Fleming, T. 2000. PDR for herbal medicines. Medical Economics Company, Montrale, Canada, 858 p.
Flemmig, J., Noetzel, I., Arnhold, J. and Rauwald, H.W. 2015. Leonurus cardiaca L. herb extracts and their constituents promote lactoperoxidase activity. Journal of Functional Foods, 17: 328-339.
Gulubov, A. and Chervenkova, V. 1970. Structure of alkaloids from Leonurus cardiaca. Materialia Fizika Khimicheskaya Biologica, 8(1): 129-132.
Gholipour, A., Ghorbani Nohooji, M., Rasuli, N. and Habibi, M. 2014. An ethnobotanical study on the medicinal plants of zarm-rood rural district of neka (Mazandaran Province). Journal of Medicinal Plants, 4(52): 101-121.
Hosseini, M., Taherkhani, M. and Ghorbani Nohooji, M. 2019. Introduction of Adonis aestivalis as a new source of effective cytotoxic cardiac glycoside. Natural Product Research, 33(6): 915-920.
Jafari, S., Moradi, A., Salaritabar, A., Hadjiakhoondi, A. and Khanavi, M. 2010. Determination of total phenolic and flavonoid contents of Leonurus cardiaca L. in compare with antioxidant activity. Research Journal of Biological Sciences, 5(7): 484-487.
Janicsák, G., Veres, K., Kakasy, A.Z. and Máthé, I. 2006. Study of the oleanolic and ursolic acid contents of some species of the Lamiaceae. Biochemical Systematics and Ecology, 34(5): 392-396.
Ji, S., Fattahi, A., Raffel, N., Hoffmann, I., Beckmann, M.W., Dittrich, R. and Schrauder, M. 2017. Antioxidant effect of aqueous extract of four plants with therapeutic potential on gynecological diseases; Semen persicae, Leonurus cardiaca, Hedyotis diffusa, and Curcuma zedoaria. European Journal of Medical Research, 22(1): 1-8.
Kartnig, T., Gruber, A. and Menzinger, S. 1985. Flavonoid-O-Glycosides from the Herbs of Leonurus cardiaca. Journal of Natural Products, 48(3): 494-507.
King, R.E. and Gisvold, O. 1950. Some extraction studies on Digitalis. Journal of the American Pharmaceutical Association, 39(2): 109-112.
Mil kowska-Leyck, K., Filipek, B. and Strzelecka, H. 2002. Pharmacological effects of lavandulifolioside from Leonurus cardiaca. Journal of Ethnopharmacology, 80(1): 85-90.
Mockute, D., Bernotiene, G. and Judzentiene, A. 2006. Germacrene D chemotype of essential oils of Leonurus cardiaca L. growing wild in Vilnius district (Lithuania). Journal of Essential Oil Research, 18(5): 566-568.
Moore, W.N. and Taylor, L.T. 1996. Extraction and quantitation of digoxin and acetyldigoxin from the digitalis lanata leaf. via near-supercritical methanol-modified carbon dioxide. Journal of Natural Products, 59(7): 690-693.
Morteza-Semnani, K., Saeedi, M. and Akbarzadeh, M. 2008. The essential oil composition of Leonurus cardiaca L. from Iran. Journal of Essential Oil Research, 20(2): 107-109.
Mozaffarian, V. 2012. Identification of medicinal and Aromatic Plants of Iran. Farhange Moase publication, Tehran, Iran, 1444 p.
Nagasawa, H., Onoyama, T., Suzuki, M., Hibino, A., Segawa, T. and Inatomi, H. 1990. Effects of motherwort (Leonurus sibiricus L.) on preneoplastic and neoplastic mammary gland growth in multiparous GR/A mice. Anticancer Research, 10:1019–1023.
Novkovic, V.M., Stanojevic, L.P., Cakic, M.D., Palic, R.M., Veljkovic, V.B. and Stankovic, M.Z. 2014. Extraction of digoxin from fermented woolly foxglove foliage by percolation. Separation Science and Technology, 49(6): 829-837.
Orosz, F., Nuridsány, M. and Ovádi, J. 1989. Isolation and quantitative determination of some cardioactive glycosides from Digitalis lanata by high-performance liquid chromatography. Analytical Biochemistry, 156(1): 171-175.
Pang, S., Tsuchiya, S., Horie, S., Uchida, M., Murayama, T. and Watanabe, K. 2001. Enhancement of phenylephrine-induced contraction in the isolated rat aorta with endothelium by H2O-extract from an Oriental medicinal plant Leonuri Herba. Japanese Journal of Pharmacology, 86(2): 215-222.
Racz-Kotilla, E., Racz, G. and Bartha, R. 1981. Antihypertensive action of Leonurus quinquelobatus and L. turkestanicus extracts. Review of Medicine, 27: 32-35.
Rezaee-Asl, M., Sabour, M., Nikoui, V., Ostadhadi, S. and Bakhtiarian, A. 2014. The study of analgesic effects of leonurus cardiaca l. in mice by formalin, tail flick and hot plate tests. International Scholarly Research Notices, Article ID 687697, 5 p.
Ritter, M., Melichar, K., Strahler, S., Kuchta, K., Schulte, J., Sartiani, L., Cerbai, E., Mugelli, A., Mohr, F.W., Rauwald, H.W. and Dhein, S. 2010. Cardiac and electrophysiological effects of primary and refined extracts from Leonurus cardiaca L. Planta Medica, 76(6): 572-582.
Sattar, A.A., Bankova, V., Kujumgiev, A., Galabov, A., Ignatova, A., Todorova, C. and Popov, S. 1995. Chemical composition and biological activity of leaf exudates from some Lamiaceae plants. Pharmazie, 50(1): 62-65.
Senatore, F., De Feo, V., De Simone, F., Mscisz, A., Mrugasiewicz, K. and Gorecki P. 1991. Sterols from Leonurus cardiaca L. growing in different geographical areas. Herba Polonica, 37(1): 3-7.
Sermukhamedova, O.V., Sakipova, Z.B., Ternynko, I.I. and Gemedzhieva, N.G., 2017. Representatives of motherwort genus (Leonurus spp.) aspects of pharmacognostic features and relevance of new species application. Acta poloniae pharmaceutica, 74(1): 31-40.
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