Advertisement

Chemistry of Natural Compounds

, Volume 40, Issue 3, pp 222–226 | Cite as

Synthesis of Fatty-Acid Ethanolamides from Linum catharticum Oils and Cololabis saira Fats

  • A. E. Karaulov
  • V. G. Rybin
  • D. V. Kuklev
  • V. N. Akulin
Article

Abstract

Ethanolamides of polyunsaturated fatty acids (9Z,12Z,15Z-octadecatrienoic; 5Z,8Z,11Z,14Z,17Z-eicosapentaenoic; and 4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoic) and mixtures of ethanolamides of fatty acids from natural fats (oils) were synthesized. It was found that the polyunsaturated fatty acids did not isomerize under the proposed conditions for aminolysis of the ester bond. Conditions for analyzing the complicated mixtures of ethanolamides of fatty acids by HPLC-MS were determined.

fatty-acid ethanolamides polyunsaturated fatty acids 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

REFERENCES

  1. 1.
    V. V. Bezuglov, M. Y. Bobrov, and A. V. Archakov, Biokhimiya (Moscow), 63, No. 1, 27 (1998).Google Scholar
  2. 2.
    F. A. Kuehl, Jr., T. A. Jacob, O. H. Ganley, R. E. Ormond, and M. A. P. Meisinger, J. Am. Chem. Soc., 79, 5577 (1957).Google Scholar
  3. 3.
    W. A. Devane, L. Hanus, A. Breuer, R. G. Pertwee, L. A. Stevenson, G. Griffin, D. Gibson, A. Mandelbaum, A. Etinger, and R. Mechoulam, Science, 258, 699 (1992).Google Scholar
  4. 4.
    B. F. Cravatt, O. Prospero-Garcia, G. Siuzdak, N. B. Gilula, J. Henriksen, D. L. Boger, and R. A. Lerner, Science, 268, 1506 (1995).Google Scholar
  5. 5.
    L. Hanus, A. Gopher, S. Almog, and R. Mechoulam, J. Med. Chem., 36, No. 20, 3032 (1993).Google Scholar
  6. 6.
    R. Pertwee, G. Griffin, L. Hanus, and R. Mechoulam, Eur. J. Pharmacol., 259, No. 2, 115 (1994).CrossRefGoogle Scholar
  7. 7.
    E. Fride, J. Barg, R. Levy, D. Saya, E. Heldman, R. Mahoulam, and Z. Vogel, J. Pharmacol. Exp. Ther., 272, No. 2, 699 (1995).Google Scholar
  8. 8.
    J. Priller, E. M. Briley, J. Mansouri, W. A. Devane, K. Mackie, and C. C. Felder, Mol. Pharmacol., 48, No. 2, 288 (1995).Google Scholar
  9. 9.
    E. Gross and J. Meienhofer, eds., The Peptides: Analysis, Synthesis, Biology, Vol. 1: Major Methods of Peptide Bond Formation, Academic Press, New York (1979).Google Scholar
  10. 10.
    A. Guiffridia and D. Piomelli, FEBS Lett., 422, 373 (1998).CrossRefGoogle Scholar
  11. 11.
    D. V. Kuklev, A. E. Karaulov, V. G. Rybin, and V. I. Vysotskii, Izv. TINRO, 129, 34 (2001).Google Scholar
  12. 12.
    W. W. Christie, J. Chromatogr. A, 447, No. 2, 305 (1988).Google Scholar
  13. 13.
    E. G. Bligh and W. J. Dyer, Can. J. Biochem. Physiol., 37, No. 8, 911 (1959).Google Scholar

Copyright information

© Plenum Publishing Corporation 2004

Authors and Affiliations

  • A. E. Karaulov
    • 1
  • V. G. Rybin
    • 1
  • D. V. Kuklev
    • 2
  • V. N. Akulin
    • 1
  1. 1.Pacific Scientific-Research Fisheries CenterVladivostokper. Shevchenko, 4
  2. 2.Biological Chemistry DivisionUniversity of Michigan Medical SchoolAnn-ArborUSA, Katerina Roud

Personalised recommendations