Characterization of a new phosphonocerebroside, N-methyl-2-aminoethylphosphonylglucosylceramide, from the antarctic krill, Euphausia superba

Biochim Biophys Acta. 1991 Feb 5;1081(3):321-7. doi: 10.1016/0005-2760(91)90289-t.

Abstract

A novel phosphonglycosphingolipid was purified from the whole tissue of the antarctic krill, Euphausia superba by successive column chromatography on DEAE- and QAE-Sephadex and silicic acid (Iatrobeads). The structure was elucidated by means of IR, FAB-MS, 1H-NMR, GC and GC-MS analyses of the water-soluble products after complete and partial acid hydrolysis, and methylation analysis of a product of hydrogen fluoride degradation; it was identified to be a phosphonocerebroside, 6'-O-(N-methyl-2-aminoethylphosphonyl)Glcp beta 1----1ceramide. The ceramide moiety was composed of tetradecasphingenine and octadecasphingatriene as the main sphingoids, and monounsaturated C22- and C24-acids and their 2-hydroxy homologues as the major fatty acids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cerebrosides / chemistry*
  • Cerebrosides / isolation & purification
  • Chromatography, Gas
  • Chromatography, Liquid
  • Chromatography, Thin Layer
  • Crustacea / metabolism*
  • Gas Chromatography-Mass Spectrometry
  • Glucosylceramides / chemistry*
  • Hydrolysis
  • Magnetic Resonance Spectroscopy
  • Phosphorylation
  • Spectrophotometry, Infrared

Substances

  • Cerebrosides
  • Glucosylceramides
  • N-methyl-2-aminoethylphosphonylglucosylceramide