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Manuscript ID : EJMP-1712-1308 (R7) Visit : 301 Page: 89 - 100

20.1001.1.23223235.1398.7.3.8.5

Article Type: Original Research

(Short paper) Extraction, isolation and chemical structure elucidation of Digoxin cardiac glycoside from Leonurus cardiaca L. extract

Subject Areas : Phytochemistry

Mahboubeh Taherkhani 1 , Shabnam Arjmandi 2 , Majid Ghorbani Nohooji3 3

1 - Department of Chemistry, College of Science, Takestan Branch, Islamic Azad University, Takestan, Iran
2 - Department of Phytochemistry and Essential Oils Technology, Faculty of Pharmaceutical Chemistry, Pharmaceutical Sciences Branch, Islamic Azad University (IAUPS) ,Tehran, Iran
3 - Medicinal Plants Research Center, Institute of Medicinal Plants, ACECR, Karaj, Iran

Received: 2017-12-31 Accepted : 2019-02-03 Published : 2019-11-22

Keywords: Iran, Cardiac glycoside, Column chromatography, Leonurus cardiaca, New source of Digoxin,

Abstract :

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.

References:


References

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    2.
  2. 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.
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    22.
  22. 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.
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  25. Mil kowska-Leyck, K., Filipek, B. and Strzelecka, H. 2002. Pharmacological effects of lavandulifolioside from Leonurus cardiaca. Journal of Ethnopharmacology, 80(1): 85-90.
    26.
  26. 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.
    27.
  27. 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.
    28.
  28. 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.
    29.
  29. Mozaffarian, V. 2012. Identification of medicinal and Aromatic Plants of Iran. Farhange Moase publication, Tehran, Iran, 1444 p.
    30.
  30. 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.
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  31. 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.
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  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.
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  43. Trumbeckaite, S., Bernatoniene, J., Majiene, D., Jakstas, V., Savickas, A. and Toleikis, A. 2006. The effect of flavonoids on rat heart mitochondrial function. Biomedicine &Pharmacotherapy, 60(5): 245-248.
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_||_

References

  1. 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.
    2.
  2. 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.
    3.
  3. 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.
    4.
  4. 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.
    5.
  5. 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.
    6.
  6. Blumenthal, M., Goldberg, A. and Brinckmann, J. 2000. Herbal medicine expanded commission e monographs. Integrative Medicine Communication. American Botanical Council: Austin, Texas, 267 p.
    7.
  7. 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.
    8.
  8. Bradley, P.R. 1992. British Herbal Compendium (Vol. 1). British Herbal Medicine Association: Bournemouth, 161p.
    9.
  9. Brieskorn, C.H. and Hofmann, R. 1979. Bitter substances from labiate plants: a clerodane derivative from Leonurus cardiac. Tetrahedron Letters, 20(27): 2511-2512.
    10.
  10. 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.
    11.
  11. 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.
    12.
  12. 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.
    13.
  13. Ewy, G.A. 2015. Digoxin: The Art and Science. The American Journal of Medicine, 128(12): 1272-1274.
    14.
  14. 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.
    15.
  15. Fleming, T. 2000. PDR for herbal medicines. Medical Economics Company, Montrale, Canada, 858 p.
    16.
  16. 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.
    17.
  17. Gulubov, A. and Chervenkova, V. 1970. Structure of alkaloids from Leonurus cardiaca. Materialia Fizika Khimicheskaya Biologica, 8(1): 129-132.
    18.
  18. 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.
    19.
  19. 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.
    20.
  20. 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.
    21.
  21. 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.
    22.
  22. 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.
    23.
  23. 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.
    24.
  24. King, R.E. and Gisvold, O. 1950. Some extraction studies on Digitalis. Journal of the American Pharmaceutical Association, 39(2): 109-112.
    25.
  25. Mil kowska-Leyck, K., Filipek, B. and Strzelecka, H. 2002. Pharmacological effects of lavandulifolioside from Leonurus cardiaca. Journal of Ethnopharmacology, 80(1): 85-90.
    26.
  26. 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.
    27.
  27. 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.
    28.
  28. 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.
    29.
  29. Mozaffarian, V. 2012. Identification of medicinal and Aromatic Plants of Iran. Farhange Moase publication, Tehran, Iran, 1444 p.
    30.
  30. 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.
    31.
  31. 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.
    32.
  32. 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.
    33.
  33. 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.
    34.
  34. Racz-Kotilla, E., Racz, G. and Bartha, R. 1981. Antihypertensive action of Leonurus quinquelobatus and L. turkestanicus extracts. Review of Medicine, 27: 32-35.
    35.
  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.
    36.
  36. 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.
    37.
  37. 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.
    38.
  38. 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.
    39.
  39. 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.
    40.
  40. Shekari, A., Nazeri, V. and Shokrpour, M. 2016. Pollen viability and storage life in Leonurus cardiaca L. Journal of Applied Research on Medicinal and Aromatic Plants, 3(3): 101-104.
    41.
  41. Sun, J., Huang, S.H., Zhu, Y.C., Whiteman, M., Wang, M.J., Tan, B.K., Zhu, Y.Z. 2005. Anti-oxidative stress effects of Herba Leonuri on ischemic hearts. Life Sciences, 76(26): 3043-3056.
    42.
  42. Taherkhani, M. and Rustaiyan, A., 2016. Investigation of in vitro cytotoxic, mutagenic and anti-mutagenic effects of shirazolide extracted from Jurinea leptoloba. Natural Product Research, 30(23): 2743-2746.
    43.
  43. Trumbeckaite, S., Bernatoniene, J., Majiene, D., Jakstas, V., Savickas, A. and Toleikis, A. 2006. The effect of flavonoids on rat heart mitochondrial function. Biomedicine &Pharmacotherapy, 60(5): 245-248.
    44.
  44. Weinges, K., Kloss, P. and Henkels, W.D. 1973. Natural products from medicinal plants. XVIII. isolation and structure elucidation of a new C15-iridoid glucoside from Leonurus cardiaca. Justus Liebigs Annalen der Chemie, 4: 566-572.
    45.
  45. Winnicka, K., Bielawski, K. and Bielawska, A. 2006. Cardiac glycosides in cancer research and cancer therapy. Acta Poloniae Pharmaceutica, 63: 109-115.
    46.
  46. Withering, W., 1785. An account of the foxglove and some of its medical uses: with Practical Remarks on Dropsy and other Diseases, Birmingham, England, 230 p.
    47.
  47. Wojtyniak, K., Szymański, M. and Matławska, I. 2013. Leonurus cardiaca L. (Motherwort): A review of its Phytochemistry and pharmacology. phytotherapy Research, 27(8): 1115-1120.
    48.
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