Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
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Isolation and NMR Assignment of a Pennogenin Glycoside from Dioscorea bulbifera L. var sativa

  • Teponno, Remy Bertrand (Department of Chemistry, Faculty of Science, University of Dschang) ;
  • Tapondjou, Azefack Leon (Department of Chemistry, Faculty of Science, University of Dschang) ;
  • Djoukeng, Jules Desire (Department of Chemistry, Faculty of Science, University of Dschang,Institute of Chemistry, University of Neuchatel) ;
  • Abou-Mansour, Eliane (Institute of Chemistry, University of Neuchatel) ;
  • Tabacci, Raphael (Institute of Chemistry, University of Neuchatel) ;
  • Tane, Pierre (Department of Chemistry, Faculty of Science, University of Dschang) ;
  • Lontsi, David (Department of Organic Chemistry, Faculty of Science, University of Yaounde) ;
  • Park, Hee-Juhn (Department of Botanical Resources, Sangji University)
  • Published : 2006.03.01
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Abstract

A steroidal saponin, $3-O-{\alpha}-L-rhamnopyranosyl-(1{\rightarrow}2)-[{\alpha}-L-rhamnopyranosyl-(1{\rightarrow}3)]-{\beta}-D-glucopyranosylpennogenin$ ;(1, spiroconazole A) was isolated from the tubers of Dioscorea bulbifera L. var sativa and $^1H-and\;^{13}C-NMR$ assignment was completed using HMBC correlation. In addition, four phenolic substances, 2,7-dihydroxy-4-methoxyphenanthrene (2), quercetin (3), $quercetin-3-O-{\beta}-D-glucopyranoside$ (4), and $quercetin-3-O-{\beta}-D-galactopyranoside$ (5) were also isolated.

Keywords

References

  1. Agrawal, P.K., NMR spectroscopy in the structural elucidation of oligosaccharides and glycosides. Phytochemistry, 31, 3307-3330 (1992) https://doi.org/10.1016/0031-9422(92)83678-R
  2. Agrawal, P.K., Jain, D.C., Gupta, R.K., Thakur, R.S., Carbon-13 NMR spectroscopy of steroidal sapogenins and steroidal saponins, Phytochemistry, 24, 2479-2496 (1985) https://doi.org/10.1016/S0031-9422(00)80653-6
  3. Arot, L.O.M. and Williams L.A.D., A flavonol glycoside from Embelia schimperi leaves. Phytochemistry, 44, 1397-1398 (1997) https://doi.org/10.1016/S0031-9422(96)00706-6
  4. Dong, M., Feng, X., Wang, B57, 501-50., Wu, L., and Ikejima, T., Two novel furostanol saponins from the rhizomes of Dioscorea panthaica Pesrain et Burkill and their cytotoxic activity. Tetrahedron, 6-12 (2001)
  5. EI-Mousallamy, A.M.D., Hussein, S.A.M., Merfort, I., and Mewwar, M. A. M., Unusual phenolic glycosides from Cotoneaster orbicularis, Phytochemistry, 53, 699-704 (2000) https://doi.org/10.1016/S0031-9422(99)00598-1
  6. Hufford, C.D., Liu, S., and Clark, A.M., Antifungal activity of Trillium grandiflorum constituents. J. Nat. Prod., 51, 94-98 (1988) https://doi.org/10.1021/np50055a013
  7. Komori, T., Glycosides from Dioscorea bulbifera, Toxicon, 35, 1531-1536 (1997) https://doi.org/10.1016/S0041-0101(97)00032-9
  8. Mahato, S.B., Sahu, N.P., and Ganguly, A.N., Steroidal saponins from Dioscorea foribunda: structures of floribundasaponins A and B. Phytochemistry, 20, 1943-1946 (1981) https://doi.org/10.1016/0031-9422(81)84040-X
  9. Majumder, P.L., Pal, S., and Majumder, S., Dimeric phenanthrenes from the orchid Bulbophyllum reptans, Phytochemistry, 50, 891-897 (1999) https://doi.org/10.1016/S0031-9422(98)00609-8
  10. Mimaki, Y., Kuroda, M., Ide, A., Kameyama, A., Yokosuka, A., and Sashida, Y., Steroidal saponins from the aerial parts of Dracaena draco and their cytostatic activity on HL-60 cells. Phytochemistry, 50, 808-813 (1999)
  11. Murray, R.D.H., Jorge, Z., Khan, N.H., Shahjahan, M., and Quaisuddin, M., Diosbulbin D and 8-Epidiosbulbin E acetate, norclerodane diterpenoids from Dioscorea bulbifera tubers. Phytochemistry, 23, 623-625 (1984) https://doi.org/10.1016/S0031-9422(00)80394-5
  12. Naheed, F., Tapondjou, A.L., Lontsi, D., Sondengam, B.L., Atta-UUr-Rahman, Choudhary, M.I., Quinovic acid glycosides from Mitragyna stipulosa-frrst examples of natural inhibitors of snake venom Phosphodiesterase I, Nat. Prod. Lett., 16, 389-393 (2002) https://doi.org/10.1080/10575630290033169
  13. Nohara, T., Miyahara, K., and Kawasaki, T., Steroid saponins and sapogenins of underground parts of Trillium kamtschaticum Pail. I. Component sapogenins and structure of pennogenins. Chem. Pharm. Bull. 22, 1772-1780 (1974) https://doi.org/10.1248/cpb.22.1772
  14. Okunji, C.O., Iwu, M.M., Jackson, J.E., Tally, J.D., Biological activity of saponins from two Dracaena species, Adv. Exp. Med. Biol., 404, 415-428 (1996)
  15. Sautour, M., Miyamoto, T., and Lacaille-Dubois M.-A, Steroidal saponins and flavan-3-olglycosides from Dioscorea villosa. Biochem. Sys. Ecol., 34, 60-63 (2006) https://doi.org/10.1016/j.bse.2005.07.007
  16. Tapondjou, A.L., Lontsi, D., Sondengam, B.L., Choudhary, M.I., Atta-Ur-Rahman, Park, H. J., Choi, J., and Lee, K. T., Structureactivity relationship of triterpenoids isolated from Mitragyna stipulosa on cytotoxicity. Arch. Pharm. Res., 25, 270-274 (2002) https://doi.org/10.1007/BF02976624
  17. Tapondjou, A.L., Lontsi, D., Sondengam, B.L., Shaheen, F., Choudhary, M.I., Atta-Ur-Rahman, Heerden, F.R., Park, H.J., and Lee K. T. Saponins from Cussonia bancoensis and their inhibitory effects on nitric oxide production. J. Nat. Prod. 66, 1266-1269 (2003) https://doi.org/10.1021/np020412g
  18. Tapondjou, A.L., Miyamoto, T., Mirjolet, J-F., Guilbaud, N., and Lacaille-Dubois M-A., Pursaethosides A-E, triterpenes saponins from Entada pursaetha. J. Nat. Prod. 68, 1185-1190 (2005) https://doi.org/10.1021/np0580311