Skip to main content
SpringerLink
Log in

Positional distribution of octadecadienoic acids in sponge phosphatidylethanolamines

  • Communication
  • Published:
Lipids

Abstract

The distribution of C14–C22 fatty acids in the phosphatidylethanolamines isolated from the spongesAgelas sp. andSpongia tampa was investigated. Selective changes with phospholipase A2 (fromAgkistrodon halys blomhoffii) followed by thin-layer chromatographic separation of the resulting lysophosphatidylethanolamines and free fatty acids and subsequent methylation with HCl/MeOH and diazomethane, respectively, revealed that the 5,9-octadecadienoic acid and the 9,12-octadecadienoic acid present showed no preference for either positionsn-1 orsn-2 in these phosphatidylethanolamines. The other saturated and unsaturated fatty acids with chains between 14 and 22 carbons long were also found to be equally distributed between positionssn-1 andsn-2 in the phosphatidylethanolamines in these sponges. The results contrast with what is known about the distribution in most mammalian phospholipids, such as the phosphatidylcholines from human erythrocytes, where octadecadienoic acid typically occupies thesn-2 position.

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

FA:

fatty acid(s)

GC/MS:

gas chromatography/mass spectrometry

PC:

phosphatidylcholine(s)

PE:

phosphatidylethanolamine(s)

TLC:

thin-layer chromatography

tris:

tris(hydroxymethyl)aminomethane

References

  1. Menzel, D.B., and Olcott, H.S. (1964)Biochim. Biophys. Acta 84, 133–139.

    CAS  PubMed  Google Scholar 

  2. Brockerhoff, A., Ackman, R.G., and Hoyle, R.J. (1963)Arch. Biochem. Biophys. 100, 9–12.

    Article  CAS  PubMed  Google Scholar 

  3. Djerassi, C., and Lam, W.-K. (1991)Acc. Chem. Res. 24, 69–75.

    Article  CAS  Google Scholar 

  4. Dasgupta, A., Ayanoglu, E., Wegmann-Szente, A., Tomer, K.B., and Dierassi, C. (1986)Chem. Phys. Lipids 41, 335–337.

    Article  CAS  PubMed  Google Scholar 

  5. Dasgupta, A., Ayanoglu, E., Tomer, K.B., and Djerassi, C. (1986)Chem. Phys. Lipids 43, 101–111.

    Article  Google Scholar 

  6. Vance, D.E., and Vance, J.E. (1985) inBiochemistry of Lipids and Membranes, pp. 28–30, Benjamin/Cummings, Menlo Park.

    Google Scholar 

  7. Gurr, M.I., and James, A.T. (1980) inLipid Biochemistry: An Introduction, p. 142, Chapman and Hall, London.

    Book  Google Scholar 

  8. Privett, O.S., Dougherty, K.A., Erdahl, W.L., and Stolyhwo, A. (1973)J. Am. Oil Chem. Soc. 50, 516–520.

    Article  CAS  PubMed  Google Scholar 

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

    CAS  PubMed  Google Scholar 

  10. Kawauchi, S., Samejima, Y., Iwanaga, S., and Suzuki, T. (1971)J. Biochem. (Japan) 69, 433–437.

    Article  CAS  Google Scholar 

  11. Martin, J.K., Luthra, M.G., Wells, M.A., Watts, R.P., and Hanahan, D.J. (1975)Biochemistry 14, 5400–5408.

    Article  CAS  PubMed  Google Scholar 

  12. Hanahan, D.J., Joseph, M., and Morales, R. (1980)Biochim. Biophys. Acta 619, 640–649.

    Article  CAS  PubMed  Google Scholar 

  13. Carreau, J.P., and Dubacq, J.P. (1978)J. Chromatogr. 151, 384–390.

    Article  CAS  Google Scholar 

  14. Francis, G.W., and Veland, K. (1981)J. Chromatogr. 219, 379–384.

    Article  CAS  Google Scholar 

  15. Carballeira, N., and Emiliano, A. (1993)Lipids 28, 763–766.

    Article  CAS  PubMed  Google Scholar 

  16. Walker, R.H., Barakat, H., and Hung, J.G.C. (1970)Lipids 5, 684.

    Article  CAS  PubMed  Google Scholar 

  17. Okuyama, H., Okajima, N., Sasaki, S., Higashi, S., and Murata, N. (1991)Biochim. Biophys. Acta 1084, 13–20.

    Article  CAS  PubMed  Google Scholar 

  18. Gillan, F.T., Stoilov, I.L., Thompson, J.E., Hogg, R.W., Wilkinson, C.R., and Djerassi, C. (1988)Lipids 23, 1139–1145.

    Article  CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Puerto Rico, P.O. Box 23346, 00931-3346, San Juan, Puerto Rico

    Néstor M. Carballeira, Anastacio Emiliano & Reginald Morales

Authors
  1. Néstor M. Carballeira
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Anastacio Emiliano
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Reginald Morales
    View author publications

    You can also search for this author in PubMed Google Scholar

About this article

Cite this article

Carballeira, N.M., Emiliano, A. & Morales, R. Positional distribution of octadecadienoic acids in sponge phosphatidylethanolamines. Lipids 29, 523–525 (1994). https://doi.org/10.1007/BF02578251

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02578251

Keywords

Search

Navigation