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Chemistry of Natural Compounds

, Volume 20, Issue 4, pp 444–450 | Cite as

Sterol sulfates from the Far Eastern holothurianCucumaria japonica

  • S. G. Batrakov
  • V. B. Muratov
  • O. G. Sakandelidze
  • O. S. Reshetova
  • B. V. Rozynov
Article
  • 33 Downloads

Abstract

A chloroform-methanol extract of the musculocutaneous sac of the Far-Eastern holothurianC. japonica has yielded a fraction of sterol sulfates (13% of the weight of the extract, 0.8% of the weight of the dry biomass), the main components of which were derivatives of cholest-5-en-3β-ol, 24-methylene-, 24-ethyl-, and 24-ethylidenecholest-5-en-3β-ols, 5α-cholestan-3β-ol, and 24-methyl- and 24-methylene-5α-cholesten-3β-ol; among the minor components were found the sulfates of 24-ethyl-5α-cholestan-3β-ol of cholesta-5,22-dien-3β-ol, of a Δ5-C30 sterol, and also of dienic and trienic C26 sterols.

Keywords

AcOH Steroid Nucleus Cholesterol Sulfate Stigmastanol Sterol Acetate 

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Literature cited

  1. 1.
    M. B. Goren and M. E. Kochansky, J. Org. Chem.,38, 3510 (1973).CrossRefGoogle Scholar
  2. 2.
    K.-A. Karlsson, B. E. Samuelson, and G. O. Steen, Biochem. Biophys. Res. Communs.,37, 22 (1969).CrossRefGoogle Scholar
  3. 3.
    T. R. Erdmann and R. H. Thomson, Tetrahedron,28, 5163 (1972).CrossRefGoogle Scholar
  4. 4.
    N. W. Wither, W. C. Kokke, M. Rohner, W. H. Fenical, and C. Djerassi, Tetrahedron Lett., 3605 (1979).Google Scholar
  5. 5.
    M. Kates, P. Tremblay, R. Anderson, and B. E. Volcani, Lipids,13, 34 (1978).CrossRefGoogle Scholar
  6. 6.
    H. Klein and C. Djerassi, Chem. Ber.,106, 1897 (1973).CrossRefGoogle Scholar
  7. 7.
    L. G. Partridge and C. Djerassi, J. Org. Chem.,42, 2799 (1977).CrossRefGoogle Scholar
  8. 8.
    J. Diekman and C. Djerassi, J. Org. Chem.,32, 1005 (1967).CrossRefGoogle Scholar
  9. 9.
    C. J. W. Brooks, E. C. Horning, and J. S. Young, Lipids,3, 391 (1968).CrossRefGoogle Scholar
  10. 10.
    C. J. W. Brooks, Philos. Trans. R. Soc. London,A293, 53 (1959).Google Scholar
  11. 11.
    S. G. Wyllie and C. Djerassi, J. Org. Chem.,33, 305 (1968).CrossRefGoogle Scholar
  12. 12.
    G. B. Elyakov, S. N. Federov, A. D. Chumak, V. V. Isakov, and V. A. Stonik, Comp. Biochem. Physiol.,71B, 325 (1982).Google Scholar
  13. 13.
    T. Yoshizawa, and Y. Nagai, Jpn. J. Exp. Med.,44, 465 (1974).PubMedGoogle Scholar
  14. 14.
    L. R. Björkman, K.-A. Karlsson, I. Pascher, and B. E. Samuelsson, Biochim. Biophys. Acta,270, 260 (1972).CrossRefGoogle Scholar
  15. 15.
    R. Goodfellow and L. J. Goad, Biochem. Soc. Trans.,1, 759 (1973).CrossRefGoogle Scholar
  16. 16.
    O. F. Smetanina, É. Nait, T. A. Kuznetsova, and G. B. Elyakov, Khim. Prir. Soedin., 585 (1981).Google Scholar
  17. 17.
    K.-A. Karlsson, in: Structure of Biological Membranes [ed. S. Abrahamsson and I. Pascher), Plenum Press, New York (1977), p. 245.CrossRefGoogle Scholar
  18. 18.
    G. C. Hansson, K.-A. Karlsson, and B. E. Samuelsson, J. Biochem. (Tokyo),83, 813 (1978).CrossRefGoogle Scholar
  19. 19.
    G. C. Hansson, K.-A. Karlsson, and B. E. Samuelsson, J. Lipid. Res.,20, 509 (1979).PubMedGoogle Scholar
  20. 20.
    K.-E. Falk, K.-A. Karlsson, and B. E. Samuelsson, Chem. Phys. Lipids,27, 9 (1980).CrossRefGoogle Scholar
  21. 21.
    G. Eisenman, Biophys. J.,2, 259 (1962).CrossRefGoogle Scholar
  22. 22.
    H. K. Kimelberg and D. Papahajopoulos, Biochim. Biophys. Acta,282, 277 (1972).CrossRefGoogle Scholar
  23. 23.
    M. Kates, Prog. Chem. Fats Lipids,15, 301 (1978).CrossRefGoogle Scholar
  24. 24.
    R. Anderson, M. Kates, and B. E. Volcani, Biochim. Biophys. Acta,528, 89 (1978).CrossRefGoogle Scholar
  25. 25.
    G. L. Mayers and T. H. Haines, Biochemistry, 6, 1665 (1967).CrossRefGoogle Scholar
  26. 26.
    T. H. Haines, Prog. Chem. Fats Lipids,11, 297 (1971).CrossRefGoogle Scholar
  27. 27.
    S. G. Batrakov, V. B. Muratov, O. G. Sakandelidze, A. V. Sulima, and B. V. Rozynov, Bioorg. Khim.,9, 539 (1983).Google Scholar
  28. 28.
    G. Rouser, G. Kritchevsky, D. Heller, and E. Lieber, J. Am. Oil Chem., Soc.,40, 425 (1963).CrossRefGoogle Scholar
  29. 29.
    V. I. Svetashev and V. E. Vaskovsky, J. Chromatogr.,67, 376 (1972).CrossRefGoogle Scholar
  30. 30.
    P. Ghosh, S. Thakur, J. Chromatogr.,240, 515 (1982).CrossRefGoogle Scholar
  31. 31.
    Yu. Kirkhner, Thin-Layer Chromatography [in Russian], Moscow (1981), p. 257.Google Scholar
  32. 32.
    L. D. Bergel'son, E. V. Dyatlovitskaya, Yu. G. Molotkovskii, S. G. Batrakov, L. I. Barsukov, and N. V. Prokazova, Preparative Biochemistry of Lipids [in Russian], Moscow (1981), p. 27.Google Scholar

Copyright information

© Plenum Publishing Corporation 1985

Authors and Affiliations

  • S. G. Batrakov
  • V. B. Muratov
  • O. G. Sakandelidze
  • O. S. Reshetova
  • B. V. Rozynov

There are no affiliations available

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