Skip to main content
Log in

Identification of novel nonmethylene-interrupted fatty acids, 7E,13E-20∶2, 7E,13E,17Z-20∶3, 9E,15E,19Z-22∶3, and 4Z,9E,15E,19Z-22∶4, in ophiuroidea (Brittle star) lipids

  • Articles
  • Published:
Lipids

Abstract

Fatty acids of Ophiuroidea (brittle star) Ophiura sarsi have been investigated by gas-liquid chromatography (GLC). About 2–13% of four unidentified fatty acids were found in total fatty acids from a sample caught at a depth of 1,100 m. Structural analyses were undertaken after partial hydrogenation of their concentrates with hydrazine hydrate and subsequent isolation of the monoenoate products by argentation thin-layer chromatography. The structures of the unidentified fatty acids were determined as 7E,13E-eicosadienoic (20∶2), 7E,13E,17Z-eicosatrienoic (20∶3), 9E,15E,19Z-docosatrienoic (22∶3), and 4Z,9E,15E,19Z-docosatetraenoic (22∶4) acids by gas chromatography-mass spectrometry of dimethyl disulfide adducts and GLC of the monoenoates on a polar column. These fatty acids belong to a family of nonmethylene-interrupted (NMI) polyunsaturated fatty acids frequently observed in marine invertebrates and conifer seeds. As far as the authors know, however, these NMI fatty acid types with mixed geometry of ethylenic bonds have not been reported previously.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

Abbreviations

DMDS:

dimethyl disulfide

ECL:

equivalent chain length

GC-MS:

gas chromatography-mass spectrometry

GLC:

gas-liquid chromatography

NMI fatty acids:

nonmethylene-interrupted fatty acids

TLC:

thin-layer chromatography

References

  1. Takagi, T., Kaneniwa, M., and Itabashi, Y. (1986) Fatty Acids in Crinoidea and Ophiuroidea: Occurrence of All-cis-6,9,12,15,18,21-Tetracosahexaenoic Acid, Lipids 21, 430–433.

    CAS  Google Scholar 

  2. Kawasaki, K., Nabeshima, Y.I., Ishihara, K., Kaneniwa, M., and Ooizumi, T. (2000) High Level of 6,9,12,15,18,21-Tetracosahexaenoic Acid Found in Lipids of Ophiuroidea Ophiura sarsi Lütken, Fish. Sci. 66, 614–615.

    Article  CAS  Google Scholar 

  3. McKenzie, J.D., Black, K.D., Kelly, M.S., Newton, L.C., Handley, L.L., Scrimgeour, C.M., Raven, J.A., and Henderson, R.J. (2000) Comparisons of Fatty Acid and Stable Isotope Ratios in Symbiotic and Non-symbiotic Brittlestars from Oban Bay, Scotland, J. Mar. Biol. Ass. U.K. 80, 311–320.

    Article  CAS  Google Scholar 

  4. Ishihara, K., Murata, M., Kaneniwa M., Saito, H., Shinohara, K., Yamamoto, M.M., Kawasaki, K., and Ooizumi, T. (1998) Effect of Tetracosahexaenoic Acid on the Content and Release of Histamine, and Eicosanoid Production in MC/9 Mouse Mast Cell, Lipids 33, 1107–1114.

    PubMed  CAS  Google Scholar 

  5. Bligh, E.G., and Dyer, W.J. (1959) A Rapid Method of Total Lipid Extraction and Purification, Can. J. Biochem. Physiol. 37, 911–917.

    PubMed  CAS  Google Scholar 

  6. Hara, A., and Taketomi, T. (1988) Chemical Study of the Mechanism for Conversion of Dimethylacetal Obtained by Methanolysis of Plasmalogen to Alkenylmethylether, J. Biochem. 104, 1011–1015.

    PubMed  CAS  Google Scholar 

  7. Ando, Y., Ota, T., and Takagi, T. (1989) Japanese Sardine Oil as a Source of 16∶3(n−4) and 16∶4(n−1) Fatty Acids, J. Am. Oil Chem. Soc. 66, 1323–1325.

    Article  CAS  Google Scholar 

  8. Ratnayake, W.M.N., Grossert, J.S., and Ackman, R.G. (1990) Studies on the Mechanism of the Hydrazine Reduction Reaction: Applications to Selected Monoethylenic, Diethylenic and Triethylenic Fatty Acids of cis Configurations, J. Am. Oil Chem. Soc. 67, 940–946.

    CAS  Google Scholar 

  9. Shibahara, A., Yamamoto, K., Nakayama, T., and Kajimoto, G. (1986) Cis-Vaccenic Acid in Mango Pulp Lipids, Lipids 21, 388–394.

    CAS  Google Scholar 

  10. Shibahara, A., Yamamoto, K., Nakayama, T., and Kajimoto, G. (1985) Rapid Determination of Double Bond Positions in Monounsaturated Fatty Acids by GC-MS and Its Application to Fatty Acid Analysis, J. Jpn. Oil Chem. Soc. 34, 618–625.

    CAS  Google Scholar 

  11. Shibahara, A., Yamamoto, K., Nakayama, T., and Kajimoto, G. (1985) cis-Vaccenic Acid in Plant Lipids. II. Determination of cis-Vaccenic Acid Content in Plant Lipids by Mass Chromatography, J. Jpn. Oil Chem. Soc. 34, 696–702.

    CAS  Google Scholar 

  12. Yamamoto, K., Shibahara, A., Nakayama, T., and Kajimoto, G. (1991) Double-Bond Localization in Heneicosapentaenoic Acid by a Gas Chromatography/Mass Spectrometry (GC/MS) Method, Lipids 26, 948–950.

    CAS  Google Scholar 

  13. Wolff, R.L. (1995) Recent Applications of Capillary Gas-Liquid Chromatography to Some Difficult Separations of Positional or Geometrical Isomers of Unsaturated Fatty Acids, in New Trends in Lipid and Lipoprotein Analyses (Sébédio, J.-L., and Perkins, E.G., eds.), pp. 147–180, AOCS Press, Champaign.

    Google Scholar 

  14. Wolff, R.L., and Bayard, C.C. (1995) Improvement in the Resolution of Individual trans-18∶1 Isomers by Capillary Gas-Liquid Chromatography: Use of a 100-m CP-Sil 88 Column, J. Am. Oil Chem. Soc. 72, 1197–1201.

    CAS  Google Scholar 

  15. Precht, D., and Molkentin, J. (2000) Identification and Quantitation of cis/trans C16∶1 and C17∶1 Fatty Acid Positional Isomers in German Human Milk Lipids by Thin-Layer Chromatography and Gas Chromatography/Mass Spectrometry, Eur. J. Lipid Sci. Technol. 102, 102–113.

    Article  CAS  Google Scholar 

  16. Ota, T., Ando, Y., Nakajima, H., and Shibahara, A. (1995) C20−C24 Monounsaturated Fatty Acid Isomers in the Lipids of Flathead Flounder, Hippoglossoides dubius, Comp. Biochem. Physiol. 111B, 195–200.

    CAS  Google Scholar 

  17. Chang, S.-P., and Miwa, T.K. (1972) Brassidic Acid: Preparation from Erucic Acid and Mechanism of Elaidinization, J. Am. Oil Chem. Soc. 49, 422–425.

    CAS  Google Scholar 

  18. Grandgirard, A., Julliard, F., Prevost J., and Sébédio, J.-L. (1987) Preparation of Geometrical Isomers of Linolenic Acid, J. Am. Oil Chem. Soc. 64, 1434–1440.

    CAS  Google Scholar 

  19. Joseph, J.D. (1989) Distribution and Composition of Lipids in Marine Invertebrates, in Marine Biogenic Lipids, Fats, and Oils (Ackman, R.G., ed.), Vol. 2, pp. 49–143, CRC Press, Boca Raton.

    Google Scholar 

  20. Joseph, J.D. (1982) Lipid Composition of Marine and Estuarine Invertebrates. Part II. Mollusca, Prog. Lipid Res. 21, 109–153.

    Article  PubMed  CAS  Google Scholar 

  21. Johns, R.B., Nichols, P.D., and Perry, G.J. (1980) Fatty Acid Components of Nine Species of Molluscs of the Littoral Zone from Australian Waters, Comp. Biochem. Physiol. 65B, 207–214.

    CAS  Google Scholar 

  22. Paradis, M., and Ackman, R.G. (1977) Potential for Employing the Distribution of Anomalous Non-Methylene-Interrupted Dienoic Fatty Acids in Several Marine Invertebrates as Part of FOod Web Studies, Lipids 12, 170–176.

    PubMed  CAS  Google Scholar 

  23. Ackman, R.G., and Hooper, S.N. (1973) Non-Methylene-Interrupted Fatty Acids in Lipids of Shallow-Water Marine Invertebrates: a Comparison of Two Molluscs (Littorina littorea and Lunatia triseriata) with the Sand Shrimp (Crangon septemspinosus), Comp. Biochem. Physiol. 46B, 153–165.

    Google Scholar 

  24. Paradis, M., and Ackman, R.G. (1975) Occurrence and Chemical Structure of Nonmethylene-Interrupted Dienoic Fatty Acids in American Oyster Crassostrea virginica, Lipids 10, 12–16.

    PubMed  CAS  Google Scholar 

  25. Ackman, R.G., Epstein, S., and Kelleher, M. (1974) A Comparison of Lipids and Fatty Acids of the Ocean Quahaug, Arctica islandica, from Nova Scotia and New Brunswick, J. Fish. Res. Board Can. 31, 1803–1811.

    CAS  Google Scholar 

  26. Takagi, T., Kaneniwa, M., Itabashi, Y., and Ackman, R.G. (1986) Fatty Acids in Echinoidea: Unusual cis-5-Olefinic Acids as Distinctive Lipid Components in Sea Urchins, Lipids 21, 558–565.

    CAS  Google Scholar 

  27. Joseph, J.D., and Fender, D.S. (1977) Non-methylene Interrupted Dienes in Decapod Crustaceans of the Southeast Atlantic Ocean, J. Am. Oil Chem. Soc. 54, 145A-146A.

    Google Scholar 

  28. Ackman, R.G. (1989) Fatty Acids, in Marine Biogenic Lipids, Fats, and Oils (Ackman, R.G., ed.), Vol. 1, pp. 103–137, CRC Press, Boca Raton.

    Google Scholar 

  29. Gunstone, F.D. (1994) Fatty Acid Structure, in The Lipid Handbook, Second Edition (Gunstone, F.D., Harwood, J.L., and Padley, F.B., eds.), pp. 1–20, Chapman & Hall, London.

    Google Scholar 

  30. Robert, E.P., and Lewis, W.S. (1977) Non-methylene Interrupted and ω4 Dienoic Fatty Acids of the White Shrimp Penaeus setiferus, Lipids 12, 544–549.

    Google Scholar 

  31. Sprecher, H. (2000) Metabolism of Highly Unsaturated n−3 and n−6 Fatty Acids, Biochim. Biophys. Acta 1486, 219–231.

    PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Yasuhiro Ando.

About this article

Cite this article

Sato, D., Ando, Y., Tsujimoto, R. et al. Identification of novel nonmethylene-interrupted fatty acids, 7E,13E-20∶2, 7E,13E,17Z-20∶3, 9E,15E,19Z-22∶3, and 4Z,9E,15E,19Z-22∶4, in ophiuroidea (Brittle star) lipids. Lipids 36, 1371–1375 (2001). https://doi.org/10.1007/s11745-001-0854-x

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11745-001-0854-x

Keywords

Navigation