Isolation and structure of a galactocerebroside from the sea cucumber Bohadschia argus.

Chem Pharm Bull (Tokyo)

Graduate School of Pharmaceutical Sciences, Kyushu University, higashi-ku, Fukuoka 812-8582, Japan.

Published: March 2009

AI Article Synopsis

  • A new galactocerebroside compound, BAC-4-4a, was isolated from the galactocerebroside BAC-4 using reversed-phase HPLC techniques.
  • The parent compound BAC-4 was extracted from the less polar lipid fraction of the sea cucumber Bohadschia argus along with known glucocerebrosides.
  • The structure of BAC-4-4a was identified through chemical and spectroscopic analysis, marking the first documented instance of a galactocerebroside being isolated and characterized from sea cucumber.

Article Abstract

A galactocerebroside (BAC-4-4a) was obtained from its parent galactocerebroside molecular species (BAC-4) by using two types of reversed-phase HPLC column. The parent cerebroside BAC-4 has been isolated from less polar lipid fraction of CHCl(3)/MeOH extract of sea cucumber Bohadschia argus, together with known typical types of glucocerebroside molecular species. The structure of BAC-4-4a was determined on the basis of chemical and spectroscopic evidences as 1-O-(beta-D-galactopyranosyl)-(2S,3R,4E)-2[(2'R,15'Z)-2-hydroxytetracosenoylamino]-4-heptadecene-1,3-diol. This is the first report of isolation and structure determination of galactocerebroside from sea cucumber.

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http://dx.doi.org/10.1248/cpb.57.315DOI Listing

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