Skip to main content
SpringerLink
Log in

Desaturation of positional and geometric isomers of monoenoic fatty acids by microsomal preparations from rat liver

  • Published:
Lipids

Abstract

A range ofcis- andtrans-monoenoic fatty acids was tested as substrates for desaturation in microsomal preparations from rat liver.Trans-monoenoic acids were generally desaturated in the Δ9 position to the same extent as stearic acid. Acids with Δ7-trans- and Δ11-trans-olefinic unsaturation produced Δ7-trans,9-cis- and Δ9-cis,11-trans-conjugated dienoic acids, respectively, but the Δ8-trans- and Δ10-trans-monoenoic acids did not give Δ8,9- or Δ9,10-allenes. Of thecis-monoenoic acids examined, only those with double bonds at or beyond the Δ14 position gave any measurable Δ9 desaturation. When Δ9 desaturation of long chain saturated acids was inhibited by adding sterculic acid, these saturated acids were desaturated at the Δ5 and Δ6 positions. Many of the monoenoic acids tested were also desaturated at the Δ5 and/or Δ6 positions, although the percentage conversions were always low. Δ9-cis,11-trans-, Δ9-cis,12-trans- and Δ9-cis,13-trans-dienoic acids, produced in situ by Δ9 desaturation of the corresponding monoenoic acids, were extensively desaturated in the Δ6 position. These results are discussed in terms of: (a) the various models proposed to explain the substrate specificities of the desaturases, and (b) the metabolism of unnatural fatty acids ingested from dietary sources.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Strittmatter, P., L. Spatz, D. Corcoran, M.J. Rogers, B. Setlow, and R. Redline, Proc. Natl. Acad. Sci. USA 71:4565 (1974).

    Article  PubMed  CAS  Google Scholar 

  2. Enoch, H.G., A. Catala, and P. Strittmatter, J. Biol. Chem. 251:5095 (1976).

    PubMed  CAS  Google Scholar 

  3. Brett, D., D. Howling, L.J. Morris, and A.T. James, Arch. Biochem. Biophys. 143:535 (1971).

    Article  PubMed  CAS  Google Scholar 

  4. James, A.T., in “Function and Biosynthesis of Lipids,” Edited by N.G. Bazan, R.R. Brenner, and N.M. Glusto, Plenum Publishing Corp., New York, NY, 1977, p. 51.

    Google Scholar 

  5. Morris, L.J., R.V. Morris, W. Kelly, and A.T. James, Biochem. J. 109:673 (1968).

    PubMed  CAS  Google Scholar 

  6. Johnson, A.R., and M.I. Gurr, Lipids 6:78 (1971).

    Article  CAS  Google Scholar 

  7. Paulsrud, J.R., S.E. Stewart, G. Graff, and R.T. Holman, Lipids 5:611 (1970).

    Article  PubMed  CAS  Google Scholar 

  8. Gurr, M.I., M.P. Robinson, A.T. James, L.J. Morris, and D. Howling, Biochim. Biophys. Acta 280:419 (1972).

    Google Scholar 

  9. Fulco, A.J., and J.F. Mead, J. Biol. Chem. 235:3379 (1960).

    PubMed  CAS  Google Scholar 

  10. Brenner, R.R., Lipids 6:567 (1971).

    Article  PubMed  CAS  Google Scholar 

  11. Houtsmuller, U.M.T., Fette Seifen Anstrichm. 80:162 (1978).

    Article  CAS  Google Scholar 

  12. Gunstone, F.D., C.M. Scrimgeour, and H.S. Vedanayagam, J. Chem. Soc. (Commun.) 916 (1974).

  13. Crossland, R.K., and K.L. Servis, J. Org. Chem. 35:3195 (1970).

    CAS  Google Scholar 

  14. Barve, J.A., and F.D. Gunstone, Chem. Phys. Lipids 7:311 (1971).

    Article  CAS  Google Scholar 

  15. Lindlar, H., Helv. Chim. Acta 35:340 (1952).

    Article  Google Scholar 

  16. Gunstone, F.D., and M. Lie Ken Jie, Chem. Phys. Lipids 4:1 (1970).

    Article  CAS  Google Scholar 

  17. Stoffel, W., Justus Liebigs Ann. Chemie 673:26 (1964).

    CAS  Google Scholar 

  18. Von Rudloff, E., J. Am. Oil Chem. Soc. 33:126 (1956).

    Google Scholar 

  19. James, A.T., P. Harris, and J. Bezard, Eur. J. Biochem. 3:318 (1968).

    Article  PubMed  CAS  Google Scholar 

  20. Brindley, D.N., and G. Hubscher, Biochim. Biophys. Acta 106:495 (1965).

    PubMed  CAS  Google Scholar 

  21. James, A.T., and E.A. Piper, Anal. Chem. 35:515 (1963).

    Article  CAS  Google Scholar 

  22. Gurr, M.I., and M.P. Robinson, Anal. Biochem. 47:146 (1972).

    Article  PubMed  CAS  Google Scholar 

  23. Brenner, R.R., Mol. Cell. Biochem. 3:41 (1974).

    Article  PubMed  CAS  Google Scholar 

  24. Inkpen, C.A., R.A. Harris, and F.W. Quackenbush, J. Lipid Res. 10:277 (1969).

    PubMed  CAS  Google Scholar 

  25. Bernert, J.T., and H. Sprecher, Biochim. Biophys. Acta 398:354 (1975).

    PubMed  Google Scholar 

  26. Pollard, M.R., The Synthesis,13C Nuclear Magnetic Resonance Spectroscopy, and Enzymic Desaturation of Some Unsaturated Fatty Acids, Ph.D. Thesis, University of St. Andrews, Scotland (1977).

    Google Scholar 

  27. Jamieson, F.R., in “Topics in Lipid Chemistry,” Vol. 1, Ch. 3, Edited by F.D. Gunstone, Logos Press, (1969).

  28. Lie Ken Jie, M.S.F., Synthesis and Properties of some Unsaturated Acids and their Derivatives, Ph.D. Thesis, University of St. Andrews, Scotland, (1968).

    Google Scholar 

  29. Lemarchal, P., and M. Bornens, Bull. Soc. Chim. Biol. 50:195 (1968).

    PubMed  CAS  Google Scholar 

  30. Jeffcoat, R., and M.R. Pollard, Lipids 12:480 (1977).

    PubMed  CAS  Google Scholar 

  31. Lippel, K., F.D. Gunstone, and J.A. Barve, Lipids 8:119 (1973).

    Article  PubMed  CAS  Google Scholar 

  32. Lippel, K., D. Carpenter, F.D. Gunstone, and I.A. Ismail, Lipids 8:124 (1973).

    Article  PubMed  CAS  Google Scholar 

  33. Cook, H.W., and M.W. Spence, Biochim. Biophys. Acta 369:129 (1974).

    PubMed  CAS  Google Scholar 

  34. Quint, J.F., and A.J. Fulco, J. Biol. Chem. 248:6885 (1973).

    PubMed  CAS  Google Scholar 

  35. Scholfield, C.R., V.L. Davison, and H.J. Dutton, J. Am. Oil Chem. Soc. 44:648 (1967).

    PubMed  CAS  Google Scholar 

  36. Carpenter, D.L., and H.T. Slover, J. Am. Oil Chem. Soc. 50:372 (1973).

    PubMed  CAS  Google Scholar 

  37. Wood, R., F. Chumbler, and R. Wiegand, J. Biol. Chem. 252:1965 (1977).

    PubMed  CAS  Google Scholar 

  38. Morrison, W.R., in “Topics in Lipid Chemistry,” Vol. 1, Ch. 2, Edited by F.D. Gunstone, Logos Press (1969).

  39. Viviani, R., Adv. Lipid Res. 8:268 (1970).

    Google Scholar 

  40. Guo, L.S.S., and J.C. Alexander, Biochim. Biophys. Acta 369:411 (1974).

    CAS  Google Scholar 

  41. Anderson, R.L., C.S. Fullmer, and E.J. Hollenbach, J. Nutr. 105:393 (1975).

    PubMed  CAS  Google Scholar 

  42. Privett, O.S., E.M. Stearns, and E.C. Nickell, J. Nutr. 92:303 (1967).

    PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Biochemistry, Medical Sciences Institute, The University Dundee, DDI 4HN, Scotland, U.K.

    Michael R. Pollard

  2. Department of Chemistry, The University, KY16 9ST, St. Andrews, Fife, Scotland

    Frank D. Gunstone

  3. Unilever Research, Colworth House, MK44 1LQ, Sharnbrook, Bedford, England

    Anthony T. James & Lindsay J. Morris

Authors
  1. Michael R. Pollard
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Frank D. Gunstone
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Anthony T. James
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Lindsay J. Morris
    View author publications

    You can also search for this author in PubMed Google Scholar

About this article

Cite this article

Pollard, M.R., Gunstone, F.D., James, A.T. et al. Desaturation of positional and geometric isomers of monoenoic fatty acids by microsomal preparations from rat liver. Lipids 15, 306–314 (1980). https://doi.org/10.1007/BF02533545

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02533545

Keywords

Search

Navigation