Two Isoflavonoid Glucoside Derivatives from Ononis serrata Growing in Egypt

  • Published : 2004.12.30

Abstract

The n-butanol soluble fraction of the extract obtained from the whole plants of Ononis serrata afforded the pterocarpan derivative medicarpin-3-O-glucoside and the isoflavone glucoside rothindin. Structures were elucidated by chemical methods, detailed spectral analyses as well as comparison with the literature data.

Keywords

References

  1. Abdel-Kader, M.S. Two new norphenylpropanoid glucosides and hemipholin from the flowers of Ononis vaginalis. J. Eraz. Chon. Soc., 8(6), 637- 9 (1997)
  2. Abdel-Kader, M.S. Phenolic constituents of Ononis vaginalis roots. Planta Medica, 67(4), 388- 90 (2001) https://doi.org/10.1055/s-2001-14325
  3. Agrawal, P.K. Carbon-13 NMR of Flavonoids. Elsevier, Amesterdam, Oxford, New York, Tokyo (1989)
  4. AI-Khalil, S.; Masalmeh, A; Abdalla, S.; Tosa, H. and Iinuma, M., N-Arachidylanthranilic acid, a new derivative from Ononis natrix. J. Nat. Prod., 58(5), 760- 3 (1995) https://doi.org/10.1021/np50119a018
  5. Amer, M.E. 9-0-Methyl spinonin, a novel glucoside from Ononis samta. Alex. J. Pharm. Sci., 15(1), 47- 9 (2001)
  6. Amer, M.E.; Abdel-Kader, M.S.; Mahmoud, Z.F; Abdel-Salam, N.A.; Yang, S.S. and Mabry, TJ. Flavonoids of Ononis vaginalis Vahl. Symb. Rev. Latinoamer. Quim., 20, 152- 3 (1989)
  7. Amer, M.E.; Kassem, FF, and Abdel-Kader, M.S., Flavonoids from Ononis serrata growing in Egypt. Alex. J. Pharm. Sci., 15 (2), 99- 102 (2001)
  8. Amer, M.E.; Kassem, FE, and Abdel-Kader, M.S., Rare 2Phenoxychromones from Ononis sarata growing in Egypt. Nat. Prod. Sci., 10(1), 32- 4 (2004)
  9. Chalmers, A.A; Rall, G.J.H., and Oberholzer, M.E., $^{13}C$ NMR of pterocarpans. Tetrahedron, 33, 1735- 7 (1977) https://doi.org/10.1016/0040-4020(77)84051-9
  10. Fraishtat, PD.; Popravko, S.A., and Vul'fson, N.S., Clover secondary metabolites. VII. Isoflavones from the roots of red clover (Trifolium pratense). Bioorganicheskaya Khimiya, 6 (11), 1722- 32 (1980)
  11. Haznagy, A; Toth, G., and Tamas, J., Constituents of the aqueous extracts from Ononis spinosa L. Arch. Pharm., 311(4), 318- 23 (1978) https://doi.org/10.1002/ardp.19783110408
  12. Jia, S.; Dong, Y.; Zheng, F; Hao, J.. and Qiu, G., Isolation and identifIcation of isoflavone glycosides from the roots of Zhongjian Jinjier (Caragana intermedia). Zhongcaoyao, 22 (10),441-3 (1991)
  13. Li, W.; Koike, K.; Asada, Y.; Hirotani, M.; Rui, H.; Yoshikawa, T, and Nikaido, T, Flavonoids from Glycyrrhiza pallidiflora hairy root cultures. Phytochemistry, 60(4), 351- 5 (2002) https://doi.org/10.1016/S0031-9422(02)00093-6
  14. Mabry, T.J.; Markham, K.R., and Thomas, M.B., The Systematic Identification of Flavonoids. Springer Verlag, Berlin, Heidelberg, New York (1974)
  15. Mahasneh, A.M., and EI-Oqlah, AA, Antimicrobial activity of extracts of herbal plants used in the traditional medicine of Jordan. J. Ethnopharrnacol., 64(3), 271- 6 (1999) https://doi.org/10.1016/S0378-8741(98)00132-9
  16. Nair, A.G.R., and Subramanian, S.S., Rothindin- a new isoflavone glucoside from Rothia indica Linn. Ind. J Chem. (B)., 14(10), 801- 2 (1976)
  17. Ohashi, H., and Imamura, H., The extractives of Japanese Cladrastis species. IX. Chemotaxonomical comparison of flavonoid constituents between Cladrastis platycarpa and C. shikokiana. Mokuzai Gakkaishi., 24(10), 750- 9 (1978)
  18. Rao, G.Y., and Rao, P.S., Chemical constituents of Rothia trifoliata. Fitoterapia, 56(5), 287- 8 (1985)
  19. Sakagami, Y; Kumai, S., and Suzuki, A, Isolation and structure of Medicarpin-$\beta$-D-glucoside in Alfalfa. Agr. Bioi. Chem., 38 (5),1031- 4 (1974) https://doi.org/10.1271/bbb1961.38.1031
  20. Shaker, K.H.; Dockendorff, K; Bernhardt, M., and Seifert, K, A new triterpenoid saponin from Ononis spinosa and two new flavonoid glycosides from Ononis vaginalis. Z Natuiforsch (B)., 59(1), 124- 8 (2004)
  21. Wollenweber, E.; Dorr, M.; Rivera, D., and Roitman J.N., Externally accumulated flavonoids in three Mediterranean Ononis species. Z Natuiforsch (C), 58(11- 12), 771- 5 (2003)
  22. Yuldashev, M.P.; Batirov, E.K.; Vdovin, A.D.; Malikov, V.M., and Yagudaev, M.R., Flavonoids of Thermopsis alterniflora. Crotonoy1thermopsoside and crotonoylcosmosiin, new acylated flavonoid glycosides. Khirn. Prir. Soedin., 3, 352- 9 (1989)