Skip to main content
SpringerLink
Log in

Synthesis of Glycosides of Lupane-Type Triterpene Acids

  • Published:
Chemistry of Natural Compounds Aims and scope

Abstract

A preparative synthesis of glucosides of the lupane-type triterpene acids betulinic, dihydrobetulinic, betulonic, dihydrobetulonic, and 3,20-dioxo-30-norlupan-28-oic was proposed. Glycosylation of 3-hydroxyacids by α-acetobromoglucose (ABG) with Ag2O was performed in pyridine (Py)to formglycosides at C-28, repeated glycosylation of which by these same reagents but in CH2Cl2 generated a glycoside bond at C-3 to form bisglucosides. 28-Glucosides of ketoacids were formed in high yields in both Py and CH2Cl2.

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

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

REFERENCES

  1. T. Fujioka, Y. Kashiwada, R. E. Kilkuskie, L. M. Cosentino, L. M. Ballas, J. B. Jiang, W. P. Janzen, I. S. Chen, and K. H. Lee, J. Nat. Prod., 57, No. 2, 243 (1994).

    Google Scholar 

  2. Y. Kashiwada, F. Hashimoto, L. M. Cosentino, C. H. Chen. P. E. Garret, and K. H. Lee, J. Med. Chem., 39, No. 5, 1016 (1996).

    Google Scholar 

  3. E. Klinotova, V. Krecek, J. Klinot, M. Endova, J. Eisenreichova, M. Budesinnsky, and M. Sticha, Collect. Czech. Chem. Commun., 62, 1776 (1997).

    Google Scholar 

  4. B. N. Kuznetsov, V. A. Levdanskii, A. P. Es?kin, and N. I. Polezhaeva, Khim. Rastit. Syr?ya, 2, No. 1, 5 (1998).

    Google Scholar 

  5. O. B. Flekhter, L. A. Baltina, L. V. Spirikhin, I. P. Baikova, and G. A. Tolstikov, Izv. Akad. Nauk, Ser. Khim., No. 3, 531 (1998).

  6. J. M. Pezzuto and M. T. Hamann, J. Nat. Prod., 63, No. 12, 1653 (2000).

    Google Scholar 

  7. O. B. Flekhter, L. T. Karachurina, V. V. Poroikov, L. R. Nigmatullina, L. A. Baltina, F. S. Zarudii, V. A. Davydova, L. V. Spirikhin, I. P. Baikova, F. Z. Galin, and G. A. Tolstikov, Bioorg. Khim., 26, No. 3, 215 (2000).

    Google Scholar 

  8. A. G. Pokrovskii, O. A. Plyasunova, T. N. Il?icheva, O. A. Borisova, N. V. Fedyuk, N. I. Petrenko, V. Z. Petukhova, E. E. Shul?ts, and G. A. Tolstikov, Khim. V Interesakh Ustoich. Razvit., No. 9, 485 (2001).

  9. J. D. Connoly and R. A. Hill, Nat. Prod. Rep., 18, 560 (2001).

    Google Scholar 

  10. I.-C. Sun, C. H. Chen, Y. Kashivada, J. H. Wu, H. K. Wang, and K. H. Lee, J. Med. Chem., 45, No. 19, 4271 (2002).

    Google Scholar 

  11. S. N. Stekhova, N. F. Samoshina, M. V. Denisenko, V. A. Denisenko, V. V. Logachev, M. M. Anisimov, and N. I. Uvarova, Rastit. Resur., 38, No. 2, 92 (2002).

    Google Scholar 

  12. A. M. Yuodvirshis, L. G. Sinyakova, and A. T. Troshchenko, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim., No. 4, No. 2, 123 (1968).

  13. A. M. Yuodvirshis and A. T. Troshchenko, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim., No. 4, No. 2, 129 (1969).

  14. N. I. Uvarova, G. I. Oshitok, V. V. Isakov, A. K. Dzizenko, and G. B. Elyakov, Dokl. Akad. Nauk SSSR, 202, No. 2, 368 (1972).

    Google Scholar 

  15. N. I. Uvarova, G. I. Oshitok, and G. B. Elyakov, Carbohydr. Res., 27, No. 1, 79 (1973).

    Google Scholar 

  16. L. E. Odinokova, G. I. Oshitok, V. A. Denisenko, V. F. Anufriev, A. M. Tolkach, and N. I. Uvarova, Khim. Prir. Soedin., 182 (1984).

  17. A. S. Ivanov, T. S. Zakharova, L. E. Odinokova, and N. I. Uvarova, Khim.-Farm. Zh., No. 9, 1091 (1987).

  18. F. M. K. Ukkonen and V. Era, Kemia-Kemi, 6, No. 5, 217 (1979).

    Google Scholar 

  19. N. D. Pokhilo, A. V. Lebedev, and N. I. Uvarova, Khim. Drev., No. 4, 99 (1988).

  20. N. D. Pokhilo and N. I. Uvarova Khim. Prir. Soedin., 325 (1988).

  21. E. W. H. Hayek, U. Jordis, W. Moche, and F. Sauter, Phytochemistry, 28, No. 9, 2229 (1989).

    Google Scholar 

  22. A. C. Pinto, A. L. Pereira, A. Kelecom, L. M. Porreca, N. M. Ribeiro, and R. A. Barnes, Chem. Pharm. Bull., 36, No. 12, 4689 (1988).

    Google Scholar 

  23. J. M. Lehn and G. Ourisson, Bull. Soc. Chim. Fr., No. 6, 1133 (1962).

  24. R. Vesterberg, Ber., 65B, 1305 (1932); Chem. Abstr., 26, 5934 (1932).

    Google Scholar 

  25. M. V. Denisenko, L. E. Odinokova, and N. I. Uvarova, Khim. Prir. Soedin., 655 (1989).

  26. L. Ruzicka, M. Brenner, and E. Rey, Helv. Chim. Acta, 85, 161 (1942); Chem. Abstr., 36, 44956 (1942).

    Google Scholar 

  27. Le Bang Shon, A. P. Kaplun, A. A. Shpilevskii, Yu. E. Andiya-Pravdivyi, S. G. Alekseeva, V. B. Grigor?ev, and V. I. Shvets, Bioorg. Khim., 24, No. 10, 787 (1998).

    Google Scholar 

  28. M. V. Denisenko, L. E. Odinokova, V. A. Denisenko, and N. I. Uvarova, Khim. Prir. Soedin., 430 (1991).

  29. A. V. Symon, A. P. Kaplun, N. K. Vlasenkova, G. K. Gerasimova, Le Bang Shon, E. F. Litvin, L. M. Kozlova, E. L. Surkova, and V. I. Shvets, Bioorg. Khim., 29, No. 2, 208 (2003).

    Google Scholar 

  30. R. T. Aplin, T. G. Halsal, and T. Norin, J. Chem. Soc., 3269 (1963).

Download references

Author information

Authors and Affiliations

  1. Far-East Division, Russian Academy of Sciences, Pacific Institute of Bioorganic Chemistry, 690022, Vladivostok, pr. 100-Let Vladivostoku, 159

    N. F. Samoshina, M. V. Denisenko, V. A. Denisenko & N. I. Uvarova

Authors
  1. N. F. Samoshina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. V. Denisenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. A. Denisenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. I. Uvarova
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Samoshina, N.F., Denisenko, M.V., Denisenko, V.A. et al. Synthesis of Glycosides of Lupane-Type Triterpene Acids. Chemistry of Natural Compounds 39, 575–582 (2003). https://doi.org/10.1023/B:CONC.0000018113.79735.34

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/B:CONC.0000018113.79735.34

Search

Navigation