Skip to main content
SpringerLink
Log in

The composition of furan fatty acids in the crayfish

  • Published:
Lipids

An Erratum to this article was published on 01 August 1988

Abstract

Capillary gas chromatography-mass spectrometry (GC-MS) analysis of the sterol ester fatty acid methyl esters of the crayfish hepatopancreas revealed the presence of at least 30 kinds of unusual furan fatty acids (F acids), which accounted for 28.49% of the total sterol ester fatty acids. On the other hand, only small amounts were found in triacylglycerols (0.5%) and phospholipids (0.7%). Among the F acids, 17 acids were the hitherto unknown ones, the major component being 12,15-epoxy-13,14-dimethyleicosa-12,14-dienoic acid (F6) (41.83% of the total F acids). These novel acids possessed chain lengths of C12 to C22, with the largest concentration at C20 (45.38%), C18 (41.97%) and C16 (10.35%). Odd-numbered F acids also were found, though in a very small amount (0.4%). In the living things other than the crayfish, the longest chain F acid (C24) was detected in the sterol ester of the carp hepatopancreas. The bullfrog, an amphibian, and the turtle, a reptilian, were found to have F acids as well in their livers.

Olefinic furan fatty acids, which were detected by GC-MS, were found to have resulted during the analytical process from cyclodehydration of the diketo-ene formed by autoxidation of the F acids.

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

Abbreviations

GC:

gas chromatography

GC-MS:

gas chromatography-mass

HPLC:

high performance liquid chromatography

TLC:

thin layer chromatography

References

  1. Morris, L.J., Marshall, M.O., and Kelly, W. (1966)Tetrahedron Lett., 4249–4253.

  2. Glass, R.L., Krick, T.P., and Eckhardt, A.E. (1974)Lipids 9, 1004–1008.

    Article  PubMed  CAS  Google Scholar 

  3. Glass, R.L., Krick, T.P., Sand, D.M., Rahn, C.H., and Schlenk, H. (1975)Lipids 10, 695–702.

    Article  PubMed  CAS  Google Scholar 

  4. Glass, R.L., Krick, T.P., Olson, D.L., and Thorpson, R.L. (1977)Lipids 12, 828–836.

    Article  PubMed  CAS  Google Scholar 

  5. Gunstone, F.D., Wijesundera, R.C., Love, R.M., and Ross, D. (1976)J. Chem. Soc. Chem. Commun. 630–631.

  6. Gunstone, F.D., Wijesundera, R.C., and Scringeour, C.M. (1978)J. Sci. Food Agric. 29, 539–550.

    Article  CAS  Google Scholar 

  7. Scrimgeous, C.M. (1977)J. Am. Oil Chem. Soc. 54, 210–211.

    Google Scholar 

  8. Hasma, H., and Subramaniam, A. (1978)Lipids 13, 905–907.

    Article  CAS  Google Scholar 

  9. Groweiss, A., and Kashman, Y. (1978)Experientia 34, 299.

    Article  CAS  Google Scholar 

  10. Spiteller, M., Spiteller, G., and Hoyer, G.A. (1980)Chem. Ber. 113, 699–709.

    CAS  Google Scholar 

  11. Pfordt, J., Thoma, H., and Spiteller, G. (1981)Liebigs Ann. Chem., 2298–2308.

  12. Sand, D.M., Schlenk, H., Thoma, H., and Spiteller, G. (1983)Biochim. Biophys. Acta 751, 455–461.

    PubMed  CAS  Google Scholar 

  13. Thoma, H., Reiner, J., and Spiteller, G. (1984)J. Chromatogr. 309, 17–32.

    PubMed  CAS  Google Scholar 

  14. Bauer, S., and Spiteller, G. (1985)Liebigs Ann. Chem., 813–821.

  15. Rau, O., Spiteller, G., and Bocker, R. (1984)Liebigs Ann. Chem., 1513–1518.

  16. Rau, O., Kern, W., and Spiteller, G. (1984)Liebigs Ann. Chem., 1504–1512.

  17. Bauer, S., and Spiteller, G. (1985)Helv. Chim. Acta 68, 1635–1638.

    Article  CAS  Google Scholar 

  18. Spitteller, G. (1985)Iyo Masu Kenkyukai Koenshu 10, 3–15.

    Google Scholar 

  19. Okajima, H., Ishii, K., and Watanabe, H. (1984)Chem. Pharm. Bul. 32, 3281–3286.

    CAS  Google Scholar 

  20. Folch, J., Lees, M., and Sloane-Stanley, G.H. (1957)J. Biol. Chem. 226, 497–509.

    PubMed  CAS  Google Scholar 

  21. Lindlar, H., and Dubuis, R. (1973)Organic Synthesis, Coll. Vol. 5 (Baumgarten, H.E., ed.) pp. 880–883, John Wiley and Sons, Inc., New York.

    Google Scholar 

  22. Schödel, R., and Spiteller, G. (1985)Helv. Chim. Acta 68, 1624–1634.

    Article  Google Scholar 

  23. Hashimoto, N., Aoyama, T., and Shioiri, T. (1981)Chem. Pharm. Bull. 29, 1475–1478.

    CAS  Google Scholar 

  24. Lie Ken Jie, M.S.F., and Sinha, S. (1981)Chem. Phys. Lipids 28, 99–109.

    Article  CAS  Google Scholar 

  25. Lie Ken Jie, M.S.F., and Ahmad, F. (1983)J. Am. Oil Chem. Soc. 60, 1783–1785.

    Google Scholar 

  26. Christie, W.W. (1982)Lipid Analysis, 2nd edn., p. 90, Pergamon Press, Oxford.

    Google Scholar 

  27. Rahn, C.H., Sand, D.M., Krick, T.P., Glass, R.L., and Schlenk, H. (1981)Lipids 16, 360–364.

    CAS  Google Scholar 

  28. Lie Ken Jie, M.S.F., and Lam, C.M. (1977)J. Chromatogr. 138, 446–448.

    Article  CAS  Google Scholar 

  29. Sand, D.M., Glass, R.L., Olson, D.L., Pike, H.M., and Schlenk, H. (1984)Biochim. Biophys. Acta 793, 429–434.

    PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. School of Health Sciences, Kyorin University, Miyashita-cho, 192, Hachioji, Japan

    Kazuo Ishii, Haruo Okajima, Tsuyoshi Koyamatsu, Youji Okada & Hiroshi Watanabe

Authors
  1. Kazuo Ishii
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Haruo Okajima
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Tsuyoshi Koyamatsu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Youji Okada
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Hiroshi Watanabe
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

An erratum to this article is available at http://dx.doi.org/10.1007/BF02536228.

About this article

Cite this article

Ishii, K., Okajima, H., Koyamatsu, T. et al. The composition of furan fatty acids in the crayfish. Lipids 23, 694–700 (1988). https://doi.org/10.1007/BF02535671

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02535671

Keywords

Search

Navigation