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Triterpenoid Saponins from a Siberian Chemorace of the Thalictrum Genus

  • A. A. Semenov
  • V. I. Lutsky
  • A. S. Gromova
  • T. V. Ganenko
  • E. A. Khamidullina
  • N. N. Trofimova
Part of the Advances in Experimental Medicine and Biology book series (AEMB, volume 405)

Abstract

Plants of the Thalictrum genus (Ranunculaceae family) grow in the temperate zones of the both hemispheres of the globe. Many of these species are met worldwide. Thalictrum minus, for example, is known in Europe, Asia, and North America. However, secondary metabolism in this species is variable. Thus, in the Bulgarian population of the plant a bisbenzylisoquinoline alkaloid, thalicarpin, has been isolated as a major secondary metabolite [1], whereas the Moldavian chemorace met hereabout produces a secoprotoberberine base, β-allocryptopine [2]. In general, all the Thalictrum species were thought to serve as producers of diverse isoquinoline and, on rare occasions, of diterpene alkaloids. T. minus widely spreads from east to west over the whole territory of Russia and is involved in the Siberian biocenoses. That is why 15 years ago we tried to assess its potential as a producer of alkaloids. However any tertiary bases have not been detected. Instead, we have found a fairly large amount of saponins. This seemed strange, since earlier in the literature there were only scarce and unreliable data on the presence of saponins of unidentified structure in the representatives of this genus. Therefore, we decided to concentrate all research efforts on the elucidation of the chemical nature of the glycosides found.

Keywords

Oleanolic Acid Carbohydrate Chain Sodium Periodate Cyclopropane Ring Triterpenoid Saponin 
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. Maleev, J. Stoichov, D. Todorov, K. Mikhaleva, N. Mollov, N.K. Duchevska. Antitumor effect of the alkaloid thaliblastine, Dokl Bulg. Akad. Nauk. 25: 713 (1975).Google Scholar
  2. 2.
    K.I. Kuchkova and G. V. Lazur’évskii. Alkaloids from Thalctrum minus growing in Moldavia. I. The Identity of mahctrirnine and β-allocryptopine, Izv. Akad. Nauk Mold.SSR, Ser. Khim. Biol. 11:43 (1965).Google Scholar
  3. 3.
    A.S. Gromova, V.l. Lutsky, A.A. Semenov, E.V. Slavyanov, V.K. Biyushkin, and G.I. Malinovsky. Triterpenoid saponins from Thalictrum minus. II. The structure of artefact, Khim. Prir od. Soed. 718 (1982).Google Scholar
  4. 4.
    A.S. Gromova, V.l. Lutsky, A.A. Semenov, V.A. Denisenko, and V.V. Isakov. Triterpenoid saponins from Thalictrum minus. III. The structure of thahcogenin, Khim. Prirod. Soed. 207 (1984).Google Scholar
  5. 5.
    A.S. Gromova, V.l. Lutsky, A.A. Semenov, V.A. Denisenko, and V.V. Isakov. Triterpenoid saponins from Thalictrum minus. IV. The structure of thalicoside A, Khim. Prirod. Soed. 213 (1984).Google Scholar
  6. 6.
    A.S. Gromova, V.l. Lutsky, S.V. Zinchenko, N.N. Trofimova, A.A. Semenov, and N.A. Nakhova. Triterpenoid saponins from Thalictrum minus. VI. The structure of thahcoside C, Khim. Prirod. Soed. 103 (1993).Google Scholar
  7. 7.
    A.S. Gromova, V.l. Lutsky, S.V. Zinchenko, T.V. Ganenko, and A.A. Semenov. Triterpenoid saponins from Thalictrum minus. VII. The structure of thahcoside E, Khim. Prirod. Soed. 567 (1993).Google Scholar
  8. 8.
    A.S. Gromova, V.l. Lutsky, A.A. Semenov, R.B. Valeev, G.A. Kalabin, and V.N. Elkin. Triterpenoid saponins from Thalictrum minus. V. The structure of thalicoside B, Khim. Prirod. Soed. 670 (1985).Google Scholar
  9. 9.
    A.S. Gromova, A.A. Semenov, V.l. Lutsky, S.V. Zinchenko, and N.N. Trofimova. Triterpenoid saponins from Thalictrum minus. VIII. The structure of thalicoside D, Khim. Prirod. Soed. 398 (1994).Google Scholar
  10. 10.
    A.S. Gromova, V.l. Lutsky, A.L. Vereshchagin, and A.A. Semenov. Application of 13C NMR spectroscopy and FAB—mass—spectrometry for investigation of minor triterpenoids of Thalictrum minus, Khim. Prirod. Soed. 107 (1987).Google Scholar
  11. 11.
    T.V. Ganenko, M.I. Isaev, M.B. Gorovits, N.D. Abdulaev, V.l. Lutsky, A.A. Semenov, and N.K. Abubakirov. Triterpenoid glycosides and their genols from Thalictrum foetidum. II. The structure of cyclofoetigenin A, Khim. Prirod. Soed. 370 (1985).Google Scholar
  12. 12.
    T.V. Ganenko, M.I. Isaev, V.l. Lutsky, A.A. Semenov, N.D. Abdulaev, M.B. Gorovits, and N.K. Abubakirov. Triterpenoid glycosides and their genols from Thalictrum foetidum. III. The structure of cyclofoetoside A, Khim. Prirod. Soed. 66 (1986).Google Scholar
  13. 13.
    T.V. Ganenko, M.I. Isaev, A.S. Gromova, N.D. Abdulaev, V.l. Lutsky, M.F. Larin, A.A. Semenov, M.B. Gorovits, and N.K. Abubakirov. Triterpenoid glycosides and their genols from Thalictrum foetidum. IV. The structure of cyclofoetoside B, Khim. Prirod. Soed. 312 (1986).Google Scholar
  14. 14.
    J. Dillon and K. Nakanishi. Absolute configurational studies of vicinal glycols and amino alkohols. I. With bis(acetylacetonato) nickel, J. Amer. Chem. Soc. 97:5417 (1975).CrossRefGoogle Scholar
  15. 15.
    L. Fieser and M. Fieser. Steroids, Reinhold Publishing Corporation, New York and Chapman & Hall, Ltd., London (1959).Google Scholar
  16. 16.
    W. Wehrli and T. Nishida. Progress in the Chemistry of Organic Natural Products, Springer—Verlag, Wien (1979).Google Scholar
  17. 17.
    T.V. Ganenko, M.I. Isaev, A.S. Gromova, N.D. Abdulaev, A.A. Semenov, M.B. Gorovits, and N.K. Abubakirov. Triterpenoid glycosides and their genols from Thalictrum foetidum. V. The structure of cyclofoetoside B, Khim. Prirod. Soed. 341 (1986).Google Scholar
  18. 18.
    T.V. Ganenko, M.I. Isaev, M.B. Gorovits, A.S. Gromova, V.l. Lutsky, A.A. Semenov, and N.K. Abubakirov. Triterpenoid glycosides and its genols from Thalictrum foetidum. I. The structure of foetoside C, Khim. Prirod. Soed. 458 (1984).Google Scholar
  19. 19.
    A.S. Gromova, V.l. Lutsky, A.A. Semenov, M.F. Larin, and R.B.Valeev. Triterpenoid glycosides of Thalictrum squarrosum. I. The structure of squarrofuric acid, Khim. Prirod. Soed. 376 (1987).Google Scholar
  20. 20.
    Yu.V. Gatilov, I.Yu. Bagryanskaya, V.l. Lutsky, A.S. Gromova, and A.A. Semenov. Triterpenoid glycosides of Thalictrum squarrosum. II. Molecular and crystal structure of squarrofuric acid, Khim. Prirod. Soed. 533 (1987).Google Scholar
  21. 21.
    V.l. Lutsky, E.A. Khamidullina, A.S. Gromova, and A.A. Semenov. Triterpenoid glycosides of Thalictrum squarrosum. III. The structure of squarrogenins 1 and 2, Khim. Prirod. Soed. 510 (1989).Google Scholar
  22. 22.
    H. Yosliimitsu, K. Hagoshi, M. Kumabe, and T. Nahara. Two new cycloartane glycosides from Thalictrum Herta, Chem. Pharm. Bull. 41:786 (1993).Google Scholar
  23. 23.
    E.A. Khamidullina, A.S. Gromova, V.l. Lutsky, A.L. Vereshchagin, A.A. Semenov, and M.F. Larin. Triterpenoid glycosides of Thalictrum squarrosum. IV. The structure of squarrosides Al, A2, Bl, and B2, Khim. Prirod. Soed. 516 (1989).Google Scholar
  24. 24.
    E.A. Khamidullina, A. S. Gromova, V.l. Lutsky, A.A. Semenov, and S.V. Zinchenko. Triterpenoid glycosides of Thalictrum squarrosum. V. The structure of squarrosides B3 and B4, Izv. Akad. Nauk, Ser. Khim. in press.Google Scholar
  25. 25.
    KD. Raldiimov, S.M. Vennenichev, V.l. Lutsky, A.S. Gromova, T.V. Ganenko, and A.A. Semenov. Triterpenoid glycosides of Thalictrum foetidum, Thalictrum minus and their antitumor activity, Khim.-Farm. Zhurn. 1434 (1987).Google Scholar
  26. 26.
    M.N. Matz, V.V. Korchov, V.l. Lutsky, A.S. Gromova, T.V. Ganenko, and A.A. Semenov. Triterpenoid glycosides of Thalictrum minus, and Thalictrum foetidum, and their contraceptive activity, Rastitelnye Resursy. 27:570(1988).Google Scholar

Copyright information

© Plenum Press, New York 1996

Authors and Affiliations

  • A. A. Semenov
    • 1
  • V. I. Lutsky
    • 1
  • A. S. Gromova
    • 1
  • T. V. Ganenko
    • 1
  • E. A. Khamidullina
    • 1
  • N. N. Trofimova
    • 1
  1. 1.Irkutsk Institute of Organic Chemistry, Siberian DivisionRussian Academy of SciencesIrkutskRussia

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