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Configuration at C-24 in steranes and sterols

Nature volume 286, pages 694–697 (1980)Cite this article

Abstract

Most marine and terrrestrial organisms and aquatic sediments contain sterols with an alkyl group at C-24. Assignment of the configuration at this position has important biosynthetic, taxonomic and geochemical implications1–3; for example, it is required to elucidate biosynthetic pathways responsible for alkylation1,2, and to reveal sources of sterols in species where there is no de novo synthesis4,5 and in recent sediments3,6. Similarly, routine separation of the C-24 isomers of steranes in sedimentary rocks (formed from sterols present at the time of deposition) should provide information on the nature of the contributing organisms and the isomerization reactions thought to occur in steranes with increasing depth of burial and the associated temperature rise7,8. Using an extension of gas Chromatographie (GC) methods applied previously to the separation of stereoisomers of acyclic isoprenoid acids9 and alkanes10, we report here (1) the complete separation of (24R)-24-methyl-5α-cholestane (I) from its C-24 isomer (II in Fig. 1), the partial separation of (24R)- and (24S)-24-ethyl-5α-cholestane (III and IV), (2) the application of these separations to a study of the C-24 configuration in the steranes of a sedimentary rock and a petroleum and in those from reduction of the sterols of a marine coccolithophorid, and (3) similar separations of the corresponding 3β -OH saturated C28 and C29 alcohols as acetates (stanol acetates).

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References

  1. Goad, L. J., Lenton, J. R., Knapp, F. F. & Goodwin, T. W. Lipids 9, 582–595 (1974).

    Article  CAS  Google Scholar 

  2. Patterson, G. W. Lipids 6, 120–127 (1971).

    Article  CAS  Google Scholar 

  3. Lee, C., Gagosian, R. B. & Farrington, J. W. Org. Geochem. 2, 103–113 (1980).

    Article  CAS  Google Scholar 

  4. Nes, W. R. Lipids 9, 596–612 (1974).

    Article  CAS  Google Scholar 

  5. Rubinstein, I. & Goad, L. J. Phytochemistry 13, 485–487 (1974).

    Article  CAS  Google Scholar 

  6. Wardroper, A. M. K., Maxwell, J. R. & Morris, R. J. Steroids 32, 203–221 (1978).

    Article  CAS  Google Scholar 

  7. Mulheirn, L. J. & Ryback, G. Nature 256, 301–302 (1975).

    Article  ADS  CAS  Google Scholar 

  8. Mackenzie, A. S., Patience, R. L., Maxwell, J. R., Vandenbroucke, M. & Durand, B. Geochim. cosmochim. Acta (in the press).

  9. Ackman, R. G., Cox, R. E., Eglinton, G., Hooper, S. N. & Maxwell, J. R. J. chromatogr. Sci. 10, 392–401 (1972).

    Article  CAS  Google Scholar 

  10. Patience, R. L., Rowland, S. J. & Maxwell, J. R. Geochim. cosmochim. Acta 42, 1871–1875 (1978).

    Article  ADS  CAS  Google Scholar 

  11. Gershengorn, M. C. et al. Biochemistry 7, 1698–1706 (1968).

    Article  CAS  Google Scholar 

  12. Bernstein, S. & Wallis, E. S. J. org. Chem. 2, 341–345 (1938).

    Article  Google Scholar 

  13. Lenfant, M., Lecompte, M. F. & Farrugia, G. Phytochemistry 9, 2529–2535 (1970).

    Article  CAS  Google Scholar 

  14. Rubinstein, I., Goad, L. J., Clague, A. D. H. & Mulheirn, L. J. Phytochemistry 15, 195–200 (1976).

    Article  CAS  Google Scholar 

  15. Anderson, R. A., Brooks, C. J. W. & Knights, B. A. J. Chromatogr. 75, 247–259 (1973).

    Article  CAS  Google Scholar 

  16. Brooks, C. J. W., Henderson, W. & Steel, G. Biochim. biophys. Acta 296, 431–445 (1973).

    Article  CAS  Google Scholar 

  17. Seifert, W. K. & Moldowan, J. M. Geochim. cosmochim. Acta 43, 77–96 (1979).

    Article  Google Scholar 

  18. Ryback, G. J. Chromatogr. 116, 207–210 (1976).

    Article  CAS  Google Scholar 

  19. Grob, K., Grob, G. & Grob, K. Jr Chromatographia 10, 181–187 (1977).

    Article  CAS  Google Scholar 

  20. Bouche, J. & Verzele, M. J. Gas Chromatogr. 6, 501–505 (1968).

    Article  CAS  Google Scholar 

  21. Murphy, M. T. J., McCormick, A. & Eglinton, G. Science 157, 1040–1042 (1967).

    Article  ADS  CAS  Google Scholar 

  22. Mulheirn, L. J. & Ryback, G. in Advances in Organic Geochemistry 1975 (eds Campos, R. and Goni, J.) 173–192 (ENADIMSA, 1977).

    Google Scholar 

  23. Mulheirn, L. J. Tetrahedron Lett. 3175–3178 (1973).

  24. Nes, W. R. et al. Lipids 12, 511–527 (1977).

    Article  CAS  Google Scholar 

  25. Thompson, M. J., Dutky, S. R., Patterson, G. W. & Gooden, E. L. Phytochemistry 11, 1781–1790 (1972).

    Article  CAS  Google Scholar 

  26. Parke, M. & Dixon, P. S. J. mar. Biol. Ass. U.K. 56, 527–594 (1976).

    Article  Google Scholar 

  27. Mclntyre, A. & Bé, A. W. H. Deep Sea Res. 14, 561–597 (1967).

    Google Scholar 

  28. Okada, H. & Honjo, S. Deep Sea Res. 20, 355–374 (1973).

    Google Scholar 

  29. Bukry, D. in The Black Sea—Geology, Chemistry and Biology (eds Degens, E. T. & Ross, D. A.) 353–363 (AAPG Memoir 20, 1974).

    Google Scholar 

  30. Arpin, N., Svec, W. A. & Liaaen-Jensen, S. Phytochemistry 15, 529–532 (1976).

    Article  CAS  Google Scholar 

  31. Volkman, J. K., Eglinton, G., Corner, E. D. S. & Sargent, J. R. in Advances in Organic Geochemistry 1979 (eds Douglas, A. G. & Maxwell, J. R.) (Pergamon, Oxford, in the press).

  32. De Leeuw, J. W., v.d. Meer, F. W. & Rijpstra, W. I. C. in Advances in Organic Geochemistry 1979 (eds Douglas, A. G. & Maxwell, J. R.) (Pergamon, Oxford, in the press).

  33. Orcutt, D. M. & Patterson, G. W. Comp. Biochem. Physiol. 50 B, 579–583 (1975).

    CAS  Google Scholar 

  34. Chuecas, L. & Riley, J. P. J. mar. Biol. Ass. U.K. 49, 97–116 (1969).

    Article  CAS  Google Scholar 

  35. Morris, L. J. J. Lipid Res. 7, 717–732 (1966).

    CAS  PubMed  Google Scholar 

  36. Ling, N. C., Hale, R. L. & Djerassi, C. J. Am. Chem. Soc. 92, 5281–5282 (1970).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Organic Geochemistry Unit, University of Bristol, School of Chemistry, Cantock's Close, Bristol, BS8 1TS, UK

    J. R. Maxwell, A. S. Mackenzie & J. K. Volkman

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  1. J. R. Maxwell
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  2. A. S. Mackenzie
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  3. J. K. Volkman
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Maxwell, J., Mackenzie, A. & Volkman, J. Configuration at C-24 in steranes and sterols. Nature 286, 694–697 (1980). https://doi.org/10.1038/286694a0

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