Skip to main content

Triterpenoid Saponins from a Siberian Chemorace of the Thalictrum Genus

  • Chapter
Saponins Used in Food and Agriculture

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.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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).

    Article  CAS  Google Scholar 

  15. L. Fieser and M. Fieser. Steroids, Reinhold Publishing Corporation, New York and Chapman & Hall, Ltd., London (1959).

    Google Scholar 

  16. W. Wehrli and T. Nishida. Progress in the Chemistry of Organic Natural Products, Springer—Verlag, Wien (1979).

    Google Scholar 

  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. 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. 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. 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. 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. 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. 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. 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. 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. 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 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1996 Plenum Press, New York

About this chapter

Cite this chapter

Semenov, A.A., Lutsky, V.I., Gromova, A.S., Ganenko, T.V., Khamidullina, E.A., Trofimova, N.N. (1996). Triterpenoid Saponins from a Siberian Chemorace of the Thalictrum Genus. In: Waller, G.R., Yamasaki, K. (eds) Saponins Used in Food and Agriculture. Advances in Experimental Medicine and Biology, vol 405. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-0413-5_16

Download citation

  • DOI: https://doi.org/10.1007/978-1-4613-0413-5_16

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4613-8041-2

  • Online ISBN: 978-1-4613-0413-5

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics