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19 New Steroidal Saponins from Allium Plants: Isolation, Structural Elucidation and Effect on Blood Coagulability

  • Jun-peng Peng
  • Xin-sheng Yao
Chapter
Part of the Advances in Experimental Medicine and Biology book series (AEMB, volume 404)

Abstract

Allium plants have been grown for many centuries for their characteristic, pungent flavor and medicinal properties. In ancient China, Egypt, and India, Allium plants (especially onion and garlic) are highly prized as foodstuffs. With regard to the chemical constituents in Allium plants, early investigations have been focused on the volatile compounds (sulfur-containing compounds) and their products, their (involatile) precursors, and the biochemical basis of flavor production.1 Since the tremendous improvements over the last two decades in techniques for the isolation, separation, and analysis of complex structures have been achieved, a variety of steroidal saponins have been isolated from Allium spp. such as A. sativum,2 A. ampeloprasum,3 A. vineale,4 and A. cepa 5. The important biological activities of the saponins are of increasing interest as recently illustrated by their potential value as antifungal agents 2,3 and anti-thrombotic agents.6

Keywords

Platelet Aggregation HMBC Spectrum Allium Sativum Steroidal Saponin Blood Coagulation Time 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.(a)
    M.H. Brodnitz, C.L. Pollock, and P.P. Vallon, Flavor components of onion oil, J. Agric. Food Chem. 17: 760 (1969);CrossRefGoogle Scholar
  2. (b).
    M. H. Brodnitz and J. V. Pascale, Thiopropanal S-oxide, a lachrymatory factor in onion, J. Agric. Food Chem. 19: 269 (1971);PubMedCrossRefGoogle Scholar
  3. (c).
    M. Boelens, P. J. deValois, H. J. Wobben, and A. Van der Gan, Volatile flavor compouds from onion, J. Agric. Food Chem. 19: 984 (1971).CrossRefGoogle Scholar
  4. (d).
    L. Schreyen, P. Dirinck, F.Van Wassenhove, and N. Schamp, Volatile flavor components of leek, J Agric. Food Chem. 24: 336 (1976).CrossRefGoogle Scholar
  5. 2.(a)
    a) H. Mutsuura, T. Ushiroguchi, Y. Itakura, N. Hayashi, and T. Fuwa, A furostanol glycoside from garlic, bulbs of Allium sativum L., Chem. Pharm. Bull., 36: 3659 (1988);CrossRefGoogle Scholar
  6. (b).
    H. Mutsuura, T. Ushiroguchi, Y. Itakura, and T. Fuwa, Further studies on steroidal glycosides from bulbs, roots, and leaves of Allium sativum L., Chem. Pharm. Bull., 37: 2741 (1989).CrossRefGoogle Scholar
  7. 3.
    T. Morita, T. Ushiroguchi, N. Hayashi, H. Matsuura, Y. Itakura, and T. Fuwa, Steroidal saponins from elephant garlic, bulbs of Allium ampeloprasum L., Chem. Pharm. Bull. 36: 3480 (1988).PubMedCrossRefGoogle Scholar
  8. 4.
    S. X. Chen and J. K. Snyder, Diosgenin-bearing, molluscicidal saponins from Allium vineale: an NMR approach for the structural assignment of oligosaccharide units, J. Org. Chem. 54: 3679 (1989).CrossRefGoogle Scholar
  9. 5.
    P. K. Kintya and L. P. Degtyareva, Steroid glycosides of garden onion seeds. Structure of ceposide D, Khim. Prir. Soedin. (1): 139 (1988).Google Scholar
  10. 6.(a)
    A. Niwa, O. Takeda, M. Ishimaru, Y. Nakamoto, K. Yamasaki, H. Konda, H. Nishio, T. Segawa, K. Fujimura, and A. Kuramoto, Screening test for platelet aggregation inhibitor in natural products. The active principle of Anmarrhenae rhizoma, Yakugaku Zasshi 108: 555 (1988);PubMedGoogle Scholar
  11. (b).
    J. X. Dong and G.Y. Han, Studies on the active constituents of Anemarrhena asphodeloides Bunge, Acta Pharm. Sinica, 27: 26 (1992).Google Scholar
  12. 7.
    Jiang Su New Medical College (ed.). Encyclopedia of Chinese Materia Medica, Shanghai Science and Technology Publisher, Shanghai 2642 (1977).Google Scholar
  13. 8.
    Institute of Botany, Chinese Academy of Sciences (ed.). Zhongguo Zhiwuzhi, Science Press, Beijing 14:260 (1980).Google Scholar
  14. 9.
    Beijing Institute of Materia Medica (ed.). Zhongyaozhi (II), People’s Health Publishing House, 2nd ed., Beijing 564 (1982).Google Scholar
  15. 10.
    J. P. Peng, Y. Wu, X.S. Yao, T. Okuyama, and T. Narui, Two new steroidal saponins from Allium macrostemon, Acta Pharm. Sinica 27: 918 (1992).Google Scholar
  16. 11.
    J. P. Peng, X. Wang, and X. S.Yao, Studies on two new furostanol glycosides from Allium macrostemon Bunge, Acta Pharm. Sinica 28: 526 (1993).Google Scholar
  17. 12.
    J. P. Peng, X. S. Yao, Y. Okada, and T. Okuyama, Structures of macrostemonoside J, K and L from Allium macrostemon Bunge, Acta Pharm. Sinica 29: 526 (1994).Google Scholar
  18. 13.
    P. K. Agrawal, D. C. Jain, R. K. Guita, and R. S. Thakur, Carbon-13 NMR spectroscopy of steroidal sapogenins and steroidal saponins, Phytochemistry 24: 2479 (1985).CrossRefGoogle Scholar
  19. 14.
    R. Saiji, K. Muradami, T. Nohara, T. Tomimatsu, A. Sato, and K. Matsuka, Studies on the constituents of Solanum plants. H. On the constituents of immature berries of Solanum nigrum L., Yakugaku Zasshi, 102: 300 (1982).Google Scholar
  20. 15.
    J. P. Peng, X. S. Yao, H. Kobayashi, and C. Y. Ma, Novel furostanol glycosides from Allium macrostemon. Planta Med., 61: 58 (1995).PubMedCrossRefGoogle Scholar
  21. 16.
    H. Mutsuura, T. Ushiroguchi, Y. Itakura, and T. Fuwa, A furostanol glycoside from Allium chinense G. Don, Chem. Pharm. Bull. 37: 1390 (1989).CrossRefGoogle Scholar
  22. 17.
    X. C. Li, D. Z. Wang, and C. R. Yang, Steroidal saponins from Chlorophytum maloyense, Phytochemistry 29: 3893 (1990).CrossRefGoogle Scholar
  23. 18.(a)
    T. Okuyama, S. Shibata, M. Hoson, T. Kawada, H. Osada, and T.Noguchi, Effect of oriental plant drugs on platelet aggregation; III. Effect of Chinese drug “Xiebai” on human platelet aggregation, Planta Med. 52: 171 (1986);CrossRefGoogle Scholar
  24. (b).
    T. Okuyama, K. Fujita, S. Shibata, M. Hoson, T. Kawada, M. Masaki, and N. Yamate, Effects of Chinese drugs “Xiebai” and “Dasuan” on human platelet aggregation, Planta Med. 55: 242 (1989).PubMedCrossRefGoogle Scholar
  25. 19.
    Y. Goda, M. Shibuta, and U. Sankawa, Inhibitors of the arachidonate cascade from Allium chinense and their effect on in vitro platelet aggregation, Chem. Pharm. Bull. 35: 2668 (1987).PubMedCrossRefGoogle Scholar
  26. 20.
    J. P. Peng, X. S. Yao, Y. Tezuka, and T. Kikuchi, Two furostanol glycosides from Allium chinense bulbs, Phytochemistry (accepted, 1996 )Google Scholar
  27. 21.
    J. Blackwood and S. Fulder, Garlic: Nature’s Original Remedy, Javelin Books, London 1986.Google Scholar
  28. 22.
    G. Vernin, J. Metzger, D.Fraisse, and C. Scharff, GC-MS computer analysis of volatile sulfur compounds in garlic essential oils. Application of the mass fragmentometry SIM technique, Planta Med. 52: 96 (1986).CrossRefGoogle Scholar
  29. 23.
    E. Block, S. Ahmad, M. K. Jain, R. W. Crecely, R. Apitz-Castro, and M. R. Cruz, (E, Z)-ajoene: a potent antithrombotic agent from garlic, J. Am. Chem. Soc. 106: 8295 (1984).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 1996

Authors and Affiliations

  • Jun-peng Peng
    • 1
  • Xin-sheng Yao
    • 2
  1. 1.Department of Applied MedicineBeijing Institute of Radiation MedicineBeijingPeople’s Republic of China
  2. 2.Department of PhytochemistryShenyang Pharmaceutical UniversityShenyangPeople’s Republic of China

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