Advertisement

Chemistry of Natural Compounds

, Volume 45, Issue 1, pp 32–39 | Cite as

Structure of oligomeric proanthocyanidines from Hedysarum thienum roots studied by thiolysis and MALDI-TOF MS

  • I. V. Nechepurenko
  • N. I. Komarova
  • Yu. V. Gerasimova
  • V. V. Koval′
  • M. P. Polovinka
  • D. V. Korchagina
  • N. F. Salakhutdinov
Article

Oligomeric proanthocyanidines from Hedysarum theinum roots that were cleaved by benzylmercaptan were shown to be heterogeneous mixtures consisting of prodelphinine and procyanidine structural units with the former dominating. Fractionation of oligomeric proanthocyanidines on polyamide and MCI gel CHP20P sorbent isolated fractions containing primarily mixtures of di- and trimeric, tri- and tetrameric, or tetra- and pentameric proanthocyanidines. Analysis by mass spectrometry (MALDI-TOF) showed that fractions of trimers and tetramers contained more proanthocyanidines with a single A-type bond than fractions of dimers and trimers.

Key words

Hedysarum theinum Krasnob. Fabaceae oligomeric proanthocyanidines A-type proanthocyanidines condensed tannins acid cleavage thiolysis mass spectrometry MALDI-TOF 

References

  1. 1.
    I. V. Nechepurenko, M. P. Polovinka, N. I. Komarova, D. V. Korchagina, N. F. Salakhutdinov, and S. B. Nechepurenko, Khim. Prir. Soedin., 26 (2008).Google Scholar
  2. 2.
    O. V. Agafonova and S. B. Volodarskaya, Rastit. Resur., 36, No. 4, 47 (2000).Google Scholar
  3. 3.
    J. M. Ricardo da Silva, J. Rigaud, V. Cheynier, A. Cheminat, and M. Moutounet, Phytochemistry, 30, 1259 (1991).CrossRefGoogle Scholar
  4. 4.
    Z. A. Kuliev, K. Kh. Kim, A. D. Vdovin, N. D. Abdullaev, Z. A. Khushbaktova, and V. N. Syrov, Khim. Prir. Soedin., 47 (2000).Google Scholar
  5. 5.
    R. S. Thompson, D. Jacques, E. Haslam, and R. J. N. Tanner, J. Chem. Soc., Perkin 1, 1387 (1972).Google Scholar
  6. 6.
    S. Matthews, I. Mila, A. Scalbert, B. Pollet, C. Lapierre, C. L. Herve du Penhoat, C. Rolando, and D. M. X. Donnelly, J. Agric. Food Chem., 45, 1195 (1997).CrossRefGoogle Scholar
  7. 7.
    J. L. Torres and C. Lozano, Chromatographia, 54, 523 (2001).CrossRefGoogle Scholar
  8. 8.
    A. C. Fletcher, L. J. Porter, E. Haslam, and R. K. Gupta, J. Chem. Soc., Perkin 1, 1628 (1977).Google Scholar
  9. 9.
    E. Haslam, in: The Flavonoids, J. B. Harborne, T. J. Mabry, and H. Mabry, eds., Chapman and Hall, London (1975), pp. 527–559.Google Scholar
  10. 10.
    P. Schofield, D. M. Mbugua, and A. N. Pell, Animal Feed Sci. Technol., 91, 21 (2001).CrossRefGoogle Scholar
  11. 11.
    Y. Yang and M. Chien, J. Agric. Food Chem., 48, 3990 (2000).PubMedCrossRefGoogle Scholar
  12. 12.
    E. L. Roux, T. Doco, P. Sarni-Manchado, Y. Lozano, and V. Cheynier, Phytochemistry, 48, 1251 (1998).CrossRefGoogle Scholar
  13. 13.
    F. Hashimoto, G.-I. Nonaka, and I. Nishioka, Chem. Pharm. Bull., 37, 77 (1989).Google Scholar
  14. 14.
    F.-L. Hsu, G.-I. Nonaka, and I. Nishioka, Chem. Pharm. Bull., 33, 3293 (1985).Google Scholar
  15. 15.
    F. Geiss, M. Heinrich, D. Hunkler, and H. Rimpler, Phytochemistry, 39, 635 (1995).CrossRefGoogle Scholar
  16. 16.
    J. M. Souquet, V. Cheynier, F. Brossaud, and M. Moutounet, Phytochemistry, 43, 509 (1996).CrossRefGoogle Scholar
  17. 17.
    L. Y. Foo, Y. Lu, A. L. Molan, D. R. Woodfield, and W. C. McNabb, Phytochemistry, 54, 539 (2000).PubMedCrossRefGoogle Scholar
  18. 18.
    H. Kolodziej, Phytochemistry, 29, 1671 (1990).CrossRefGoogle Scholar
  19. 19.
    E. C. Bate-Smith, Phytochemistry, 14, 1107 (1975).CrossRefGoogle Scholar
  20. 20.
    E. B. Walker, R. A. Mickelsen, and J. N. Mickelsen, U.S. Pat. No. 5,650,432 (1997); Chem. Abstr., 127, 117374 (1997).Google Scholar
  21. 21.
    L.-C. Lin, Y.-C. Kuo, and C.-J. Chou, J. Nat. Prod., 65, 505 (2002).PubMedCrossRefGoogle Scholar
  22. 22.
    T. Bruyne, L. Pieters, M. Witvrouw, E. Clercq, D. V. Berghe, and A. J. Vlietinck, J. Nat. Prod., 62, 954 (1999); H.-Y. Cheng, C.-C. Lin, and T.-C. Lin, Antiviral Chem. Chemotherapy, 13, 223 (2002); Chem. Abstr., 139, 207137 (2003).PubMedCrossRefGoogle Scholar
  23. 23.
    K. Taguchi, S. Taguchi, and K. Miyamoto, Jpn. Pat. No. 2003212783 (2003); Chem. Abstr., 139, 122707 (2003).Google Scholar
  24. 24.
    H. G. Preuss and D. Bagchi, U.S. Pat. No. 6,500,469 (2002); Chem. Abstr., 138, 49943 (2002).Google Scholar
  25. 25.
    G. I. Baram, M. A. Grachev, N. I. Komarova, M. P. Perelroyzen, Yu. A. Bolvanov, S. V. Kuzmin, V. V. Kargaltsev, and E. A. Kuper, J. Chromatogr., 264, 69 (1983).CrossRefGoogle Scholar
  26. 26.
    J. G. Kirchner, Techniques of Chemistry, Vol. 14: Thin-Layer Chromatography, 2nd Ed., Wiley-Interscience, New York (1978).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2009

Authors and Affiliations

  • I. V. Nechepurenko
    • 1
  • N. I. Komarova
    • 1
  • Yu. V. Gerasimova
    • 2
    • 3
  • V. V. Koval′
    • 2
    • 3
  • M. P. Polovinka
    • 1
    • 3
  • D. V. Korchagina
    • 1
  • N. F. Salakhutdinov
    • 1
  1. 1.N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian BranchRussian Academy of SciencesNovosibirskRussia
  2. 2.Institute of Chemical Biology and Fundamental Medicine, Siberian BranchRussian Academy of SciencesNovosibirskRussia
  3. 3.Novosibirsk State UniversityNovosibirskRussia

Personalised recommendations