Skip to main content

Thank you for visiting nature.com. You are using a browser version with limited support for CSS. To obtain the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Internet Explorer). In the meantime, to ensure continued support, we are displaying the site without styles and JavaScript.

  • Article
  • Published:

Correlation of Stereoisomerism in Present Day and Geologically Ancient Isoprenoid Fatty Acids

Nature volume 218, pages 1019–1024 (1968)Cite this article

Abstract

High resolution gas chromatography of the methyl esters of individual isoprenoid fatty acids isolated from a geological source of the Eocene period has shown a diastereoisomer composition compatible with a chlorophyll derivation for the acids. The L-menthyl esters give enhanced separation of isoprenoid acid diastereoisomers on an optically inactive GC substrate and could be employed on samples with more complex stereochemistry.

This is a preview of subscription content, access via your institution

Access options

Buy this article

  • Purchase on Springer Link
  • Instant access to full article PDF
Buy now

Prices may be subject to local taxes which are calculated during checkout

Similar content being viewed by others

References

  1. Odham, G., Fette Seifen Anstrichmittel, 69, 164 (1967).

    Article  CAS  Google Scholar 

  2. Ackman, R. G., and Hansen, R. P., Lipids, 2, 357 (1967).

    Article  CAS  Google Scholar 

  3. Sen Gupta, A. K., and Peters, H., Fette Seifen Anstrichmittel, 68, 349 (1966).

    Article  CAS  Google Scholar 

  4. Ackman, R. G., and Sipos, J. C., Comp. Biochem. Physiol., 15, 445 (1965).

    Article  CAS  Google Scholar 

  5. Ackman, R. G., Sipos, J. C., and Tocher, C. S., J. Fish. Res. Board Canada, 24, 635 (1967).

    Article  CAS  Google Scholar 

  6. Ackman, R. G., and Hooper, S., Comp. Biochem. Physiol., 24, 549 (1968).

    Article  CAS  Google Scholar 

  7. Sonneveld, W., Haverkamp Begemann, P., van Beers, G. J., Keuning, R., and Schogt, J. C. M., J. Lipid Res., 3, 351 (1962).

    CAS  Google Scholar 

  8. Lough, A. K., Biochem. J., 86, 14 (1963).

    Google Scholar 

  9. Lough, A. K., Biochem. J., 91, 584 (1964).

    Article  CAS  Google Scholar 

  10. Hansen, R. P., and Shorland, F. B., Biochem. J., 50, 358 (1951).

    Article  Google Scholar 

  11. Hansen, R. P., and Morrison, J. D., Biochem. J., 93, 225 (1964).

    Article  CAS  Google Scholar 

  12. Hansen, R. P., Chem. and Ind., 303 (1965).

  13. Hansen, R. P., New Zealand J. Sci., 8, 158 (1965).

    CAS  Google Scholar 

  14. Hansen, R. P., Chem. and Ind., 1258 (1965).

  15. Hansen, R. P., Shorland, F. B., and Morrison, J. D., J. Dairy Res., 32, 21 (1965).

    Article  CAS  Google Scholar 

  16. Hansen, R. P., Biochim. Biophys. Acta, 106, 304 (1965).

    Article  CAS  Google Scholar 

  17. Hansen, R. P., J. Dairy Res., 33, 333 (1966).

    Article  CAS  Google Scholar 

  18. Avigan, J., Biochim. Biophys. Acta, 125, 607 (1966).

    Article  CAS  Google Scholar 

  19. Cason, J., and Graham, D. W., Tetrahedron, 21, 471 (1965).

    Article  CAS  Google Scholar 

  20. Blumer, M., and Cooper, W. J., Science (in the press).

  21. Eglinton, G., Douglas, A. G., Maxwell, J. R., Ramsay, J. N., and Ställberg-Stenhagen, S., Science, 153, 1133 (1966).

    Article  ADS  CAS  Google Scholar 

  22. Haug, P., Schnoes, H. K., and Burlingame, A. L., Science, 158, 772 (1967).

    Article  ADS  CAS  Google Scholar 

  23. McCarthy, R. D., and Duthie, A. H., J. Lipid Res., 3, 117 (1962).

    CAS  Google Scholar 

  24. Nicolaides, N., and Ray, T., J. Amer. Oil Chem. Soc., 42, 702 (1965).

    Article  CAS  Google Scholar 

  25. Ackman, R. G., J. Chromatog. (in the press).

  26. Crabbé, P., Djerassi, C., Eisenbraun, E. J., and Shuyen-Liu, Proc. Chem. Soc., 264 (1959).

  27. Burrell, J. W. K., Garwood, R. F., Jackman, L. M., Oskay, E., and Weedon, B. C. L., J. Chem. Soc., 2144 (1966).

  28. Kates, M., Yengoyan, L. S., and Sastry, P. S., Biochim. Biophys. Acta, 98, 252 (1965).

    Article  CAS  Google Scholar 

  29. Kates, M., Joo, C. N., Palameta, B., and Shier, T., Biochemistry, 6, 3329 (1967).

    Article  CAS  Google Scholar 

  30. Sato, K., Mizuno, S., and Hirayama, M., J. Org. Chem., 32, 177 (1967).

    Article  CAS  Google Scholar 

  31. Abrahamsson, S., Ställberg-Stenhagen, S., and Stenhagen, E., Progress in the Chemistry of Fats and Other Lipids, Vol. VII, Part 1, pp. 98, 99 (Pergamon Press, Oxford, 1963).

    Google Scholar 

  32. Hansen, R. P., Biochim. Biophys. Acta (in the press).

  33. Avigan, J., Steinberg, D., Gutman, A., Mize, C. E., and Milne, G. W. A., Biochem. Biophys. Res. Commun., 24, 838 (1966).

    Article  CAS  Google Scholar 

  34. Blumer, M., Science, 140, 974 (1963).

    Article  ADS  CAS  Google Scholar 

  35. Avigan, J., and Blumer, M., J. Lipid Res. (in the press).

  36. Ackman, R. G., and Eaton, C. A., Canad. J. Biochem. (in the press).

  37. Christophe, J., and Popják, G., J. Lipid Res., 2, 244 (1961).

    Google Scholar 

  38. Blumer, M., and Thomas, D. W., Science, 147, 1148 (1965).

    Article  ADS  CAS  Google Scholar 

  39. Ackman, R. G., J. Chromatog., 28, 225 (1967).

    Article  CAS  Google Scholar 

  40. Murray, K. E., Austral. J. Chem., 12, 657 (1959).

    Article  CAS  Google Scholar 

Download references

Author information

Author notes

  1. GEOFFREY EGLINTON

    Present address: Organic Geochemistry Unit, School of Chemistry, University of Bristol,

  2. K. DOURAGHI-ZADEH

    Present address: Department of Chemistry, Tehran University, Iran

Authors and Affiliations

  1. Department of Chemistry, University of Glasgow,

    IAIN MACLEAN, GEOFFREY EGLINTON & K. DOURAGHI-ZADEH

  2. Fisheries Research Board of Canada, Halifax Laboratory, Halifax, Nova Scotia

    R. G. ACKMAN & S. N. HOOPER

Authors
  1. IAIN MACLEAN
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. GEOFFREY EGLINTON
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. K. DOURAGHI-ZADEH
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. R. G. ACKMAN
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. S. N. HOOPER
    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

MACLEAN, I., EGLINTON, G., DOURAGHI-ZADEH, K. et al. Correlation of Stereoisomerism in Present Day and Geologically Ancient Isoprenoid Fatty Acids. Nature 218, 1019–1024 (1968). https://doi.org/10.1038/2181019a0

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1038/2181019a0

This article is cited by

Comments

By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.

Search

Advanced search

Quick links

Nature Briefing

Sign up for the Nature Briefing newsletter — what matters in science, free to your inbox daily.

Get the most important science stories of the day, free in your inbox. Sign up for Nature Briefing