Skip to main content
Log in

Hydrocarbon chain distribution of ether phospholipids of the ascidianHalocynthia roretzi and the sea urchinStrongylocentrotus intermedius

  • Article
  • Published:
Lipids

Abstract

The contents and compositions of the 1-O-alk-1′-enyl-2-acyl, 1-O-alkyl-2-acyl, and 1,2-diacyl glycerophospholipids in the muscle and viscera of the ascidianHalocynthia roretzi, and of the gonad of the sea urchinStrongylocentrotus intermedius, which are eaten to some extent in Alaska and in Asia, were analyzed by gas-liquid chromatography. 1-O-Alk-1′-enyl-2-acyl glycerophospholipids were found in all of the samples, accounting for 64.4–69.0% of the ethanolamine glycerophospholipid (EPL). By contrast, the levels of the 1-O-Alk-1′-enyl-2-acyl choline glycerophospholipids (CPL) were low (3.1–5.7%). CPL was rich in the 1-O-alkyl-2-acyl subclass amounting to 12.5–23.9% in the ascidian sample. The level of CPL in the sea urchin gonad was extremely high, amounting to 46.1%. The most prominent alkyl chains in thesn-1 position of CPL from the ascidian muscle were 16∶0 (44.6%), 18∶1 (26.5%), and 18∶0 (10.7%), and of CPL from the sea urchin gonad were 18∶0 (36.2%), 16∶0 (33.0%), and 18∶1 (17.8%). Unusually high levels of odd-numbered alkyl chains, e.g., 19∶0 andanteiso 17∶0, were detected in the CPL of all samples. The prominent alkenyl chains of EPL were 18∶0 (69.4%), 16∶0 (10.0%), and 18∶1 (8.54%) (not counting the vinyl double bond) for the sea urchin gonad. Relatively high levels of 20∶1 alkenyl chains were also present. The glycerolsn-2 positions contained high proportions of polyunsaturated fatty acids. Thus, 20∶5n-3 (43.6%) and 22∶6n-3 (20.1%) were most abundant in the alkylacyl CPL from the ascidian muscle and 20∶5n-3 (54.9%) and 20∶4n-6 (30.1%) in alkylacyl CPL from the sea urchin gonad. Despite a possible interconversion of the alkyl and alkenyl chains of each class of the ether phospholipids, they showed few features in common.

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

CPL:

choline glycerophospholipids

EPL:

ethanolamine glycerophospholipids

GLC:

gas-liquid chromatography

NL:

nonpolar lipids

PL:

polar lipids

TL:

total lipids

TLC:

thin-layer chromatography

TMS:

trimethylsilyl

References

  1. Sargent, J.R. (1989) Ether-Linked Glycerides in Marine Animals, inMarine Biogenic Lipids, Fats, and Oils (Ackman, R.G., ed.) pp. 175–197. CRC Press, Boca Raton.

    Google Scholar 

  2. Dembitskii, V.M. (1979) Plasmalogens in Phospholipids of Marine Invertebrates,Biol. Morya 5, 86–90.

    Google Scholar 

  3. Dembitskii, V.M., and Vas’kovsky, V.E. (1976) Distribution of Plasmalogens in Different Phospholipid Classes in Marine Invertebrates,Mar. Biol. 5, 68–72.

    Google Scholar 

  4. Weber, N. (1985) Metabolism of Orally Administeredrac-1-O-[1′-14C] Dodecylglycerol and Nutritional Effects of Dietaryrac-1-O-Dodecylglycerol in Mice,J. Lipid Res. 26, 1412–1420.

    PubMed  CAS  Google Scholar 

  5. Blank, M.L., Cress, E.A., Smith, Z.L., and Snyder, F. (1991) Dietary Supplementation with Ether-Linked Lipids and tissue Lipid Composition,Lipids 26, 166–169.

    PubMed  CAS  Google Scholar 

  6. Das, A.K., Holmes, R.D., Wilson, G.N., and Hajra, K. (1992) Dietary Ether Lipid Incorporation into Tissue Plasmalogens of Human and Rodents,Lipids 27, 401–405.

    PubMed  CAS  Google Scholar 

  7. Joh, Y.G., and Hata, MK. (1979) Studies on the Lipids of Abalone. I. The Aldehyde Composition of Plasmalogen from Abalone and Some Marine Molluscs,Bull. Korean Fish. Soc. 12, 181–189.

    CAS  Google Scholar 

  8. Koizumi, C., Jeong, KB.Y., and Ohshima, T. (1990) Fatty Chain Composition of Ether and Ester Glycerophospholipids in the Japanese OysterCrassostrea gigas (Thunberg),Lipids 25, 363–370.

    CAS  Google Scholar 

  9. Jeong, B.Y., Ohshima, T., and Kouzumi, C. (1990) Molecular Species of 1-O-Alk-1′-Enyl-2-Acyl-, 1-O-Alkyl-2-Acyl- and 1,2-Diacyl Glycerophospholipids in Japanese OysterCrassostrea gigas (Thunberg),Lipids 25, 624–632.

    CAS  Google Scholar 

  10. Jeong, B.Y., Ohshima, T., and Koizumi, C. (1991) Changes in Fatty Chain Composition of Ether and Ester Glycerophospholipids of Japanese OysterCrassostrea gigas During Frozen Storage,Nippon Suisan Gakkaishi 57, 561–570.

    CAS  Google Scholar 

  11. Jeong, B.Y., Ohshima, T., and Koizumi, C. (1991) Changes in Molecular Species Compositions of Glycerophospholipids in Japanese OysterCrassostrea gigas (Thunberg) During Frozen Storage,Comp. Biochem. Physiol. 100B, 99–105.

    CAS  Google Scholar 

  12. Vysotskii, M.V., Ota, T., and Takagi, T. (1992) n-3 Polyunsaturated Fatty Acids in Lipids of AscidianHalocynthia roretzi, Nippon Suisan Gakkaishi 58, 953–958.

    CAS  Google Scholar 

  13. 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 

  14. Hanahan, D.J., Dittmer, J.C., and Warashina, E. (1957) A Column Chromatographic Separation of Classes of Phospholipids,J. Biol. Chem. 228, 685–700.

    PubMed  CAS  Google Scholar 

  15. Bartlett, G.R. (1959) Phosphorus Assay in Column Chromatography,J. Biol. Chem. 234, 466–468.

    PubMed  CAS  Google Scholar 

  16. Renkonen, O. (1966) Individual Molecular Species of Phospholipids. III. Molecular Species of Ox-Brain Lecithin,Biochim. Biophys. Acta 125, 288–309.

    CAS  Google Scholar 

  17. Mueller, H.W., O’Flaherty, J.T., Green, D.G., Samuel, M.P., and Wykle, R.L. (1984) 1-O-Alkyl-Linked Glycerophospholipids of Human Neutrophils: Distribution of Arachidonate and Other Acyl Residues in the Ether-Linked and Diacyl Species,J. Lipid Res. 25, 383–388.

    PubMed  CAS  Google Scholar 

  18. Ohshima, T., Wada, S., and Koizumi, C. (1989) Selected Ion Monitoring Gas Chromatography/Mass Spectrometry of 1,2-Diacyl Glyceroltert-Butyldimethylsilyl Ethers Derived from glycerophospholipids,Lipids 24, 363–370.

    CAS  Google Scholar 

  19. Rapport, M.M., and Alonzo, N. (1960) Structure of Plasmalogens. V. Lipids ofMarine Invertebrates,J. Biol. Chem. 235, 1953–1956.

    PubMed  CAS  Google Scholar 

  20. Roots, B.I., and Johnston, P.V. (1968) Plasmalogens of the Nervous System and Environmental Temperature,Comp. Biochem. Physiol. 26, 553–560.

    Article  PubMed  CAS  Google Scholar 

  21. Chacko, G.K., Goldman, D.E., and Pennock, B.E. (1972) Composition and Characterization of the Lipids of Garfish (Lepisosteus osseus) Olfactory Nerve, a Tissue Rich in Axsonal Membrane,Biochim. Biophys. Acta 280, 1–16.

    PubMed  CAS  Google Scholar 

  22. Snyder, F., Malone, B., and Blank, M.L. (1969) Biosynthesis of Alkyl Glyceryl Ethers by Microsomal Enzymes of Digestive Glands and Gonads of the Starfish,Asterias forbesi, Biochim. Biophys. Acta 187, 302–306.

    PubMed  CAS  Google Scholar 

  23. Thompson, G.A. Jr., and Lee, P. (1965) The α-Glyceryl Ether Lipids Occurring in Molluscan Tissues,Biochim. Biophys. Acta 98, 151–159.

    PubMed  CAS  Google Scholar 

  24. Todd, D., and Rizzi, G.P. (1964) Biochemistry of the α-Glyceryl Ethers. I. Distribution in Mammalian Tissues and in Starfish,Proc. Soc. Exptl. Biol. Med. 115, 218–222.

    CAS  Google Scholar 

  25. Lewis, R.W. (1966) Marine Lipids-Fatty Acid Composition of Some Marine Animals from Various Depths-Glyceryl Ethers of Some Marine Animals,Comp. Biochem. Physiol. 19, 363–377.

    Article  CAS  Google Scholar 

  26. Wykle, R.L., Blank, M.L., Malone, B., and Snyder, F. (1972) Evidence for a Mixed Function Oxidase in the Biosynthesis of Ethanolamine Plasmalogens from 1-Alkyl-2-Acyl-sn-3-Phosphorylethanolamine,J. Biol. Chem. 247, 5442–5447.

    PubMed  CAS  Google Scholar 

  27. Horrocks, L.A., and Radominska-Pyrek, A. (1972) Enzymic Synthesis of Ethanolamine Plasmalogens from 1-alkyl-2-Acyl-sn-Glycero-3-(32P)-Phosphorylethanolamines by Microsomes from Rat Brain,FEBS Lett. 22, 190–192.

    Article  PubMed  CAS  Google Scholar 

  28. Paltauf, F., Prough, R.A., Masters, B.S.S., and Johnston, J.M. (1974) Evidence for the Participation of Chytochrome b5 in Plasmalogen Biosynthesis,J. Biol. Chem. 249, 2661–2662.

    CAS  Google Scholar 

  29. Thompson, G.A. Jr. (1968) The Biosynthesis of Ether-Containing Phospholipids in the Slag, Arionater. III. Origin of the Vinylic Ether Bond of Plasmalogens,Biochim. Biophys. Acta 152, 409–411.

    PubMed  CAS  Google Scholar 

  30. Wood, R., and Healy, K. (1970) Tumor Lipids. Biosynthesis of Plasmalogens,J. Biol. Chem. 245, 2640–2648.

    PubMed  CAS  Google Scholar 

  31. Stoffel, W., and Le Kim, D. (1971) Biosynthesis of Plasmalogens. Precursors in the Biosynthesis of Plasmalogens. Stereospecificity of the Biochemical Dehydrogenation of the 1-O-Alkylglyceryl to the 1-O-Alk-1′-Enylglyceryl Ether Bond,Z. Physiol. Chem. 352, 501–511.

    CAS  Google Scholar 

  32. Poulos, A., and Thompson, G.A. Jr. (1971) Ether-Containing Lipids of the Slime Mold,Physarum polycephalum. II. Rates of Biosynthesis,Lipids 6, 470–474.

    CAS  Google Scholar 

  33. Warner, H.R., and Lands, W.E.M. (1961) Metabolism of Plasmalogen: Enzymic Hydrolysis of the Vinyl Ether,J. Biol. Chem. 236, 2404–2409.

    PubMed  CAS  Google Scholar 

  34. Bishop, J.E., and Hajra, A.K. (1981) Mechanism and Specificity of Formation of Long-Chain Alcohols by Developing Rat Brain,J. Biol. Chem. 256, 9542–9550.

    PubMed  CAS  Google Scholar 

  35. Paltauf, F. (f1983) Biosynthesis of 1-O-(1′-Alkenyl)Glycerolipids (plasmalogens), inEther Lipids: Biochemical and Biomedical Aspects (Mangold, H.K., and Paltauf, F., eds.) pp. 107–128, Academic Press, New York.

    Google Scholar 

  36. Heymans, H.S.A., Schutgens, R.H.H., Tan, R., Van den Bosch, H., and Borst, P. (1983) Severe Plasmalogen Defficiency in Tissues of Infants Without Peroxisomes (Zellweger syndrome),Nature 306, 69–70.

    Article  PubMed  CAS  Google Scholar 

  37. Das, A.K., and Hajra, A.K. (1988) High Incorporation of Dietary 1-O-Heptadecyl Glycerol into Tissue Plasmalogens of Young Rats,FEBS Lett. 227, 187–190.

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

About this article

Cite this article

Jeong, B.Y., Ohshima, T. & Koizumi, C. Hydrocarbon chain distribution of ether phospholipids of the ascidianHalocynthia roretzi and the sea urchinStrongylocentrotus intermedius . Lipids 31, 9–18 (1996). https://doi.org/10.1007/BF02522404

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02522404

Keywords

Navigation