Letter | Published:

Configuration at C-24 in steranes and sterols

Nature volume 286, pages 694697 (14 August 1980) | Download Citation

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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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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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https://doi.org/10.1038/286694a0

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