Structure of a new neuritogenic-active ganglioside from the sea cucumber Stichopus japonicus

Masafumi Kaneko, Fumiaki Kisa, Koji Yamada, Tomofumi Miyamoto, Ryuichi Higuchi

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32 Citations (Scopus)

Abstract

A new ganglioside molecular species SJG-2 has been obtained from the n-hexane-soluble lipid fraction of the chloroform/methanol extract of the sea cucumber Stichopus japonicus. On the basis of chemical and spectroscopic evidence, the structure of SJG-2 has been determined, as NeuAcα2→4(NeuAcα2→3)Ga1β1→ 8NeuAcα2→3Ga1NAcβ1→ 3Ga1β1→G1cβ1γ1Cer. The new ganglioside SJG-2, possessing a unique carbohydrate moiety, is the first ganglioside containing either a branched sugar chain moiety or an N-acetylgalactosamine residue to be isolated from a sea cucumber. Partial hydrolysis with hot water and dilute acetic acid has proved useful for the structure elucidation of the complex oligosaccharide moieties. Moreover, the ganglioside SJG-2 exhibits neuritogenic activity toward the rat pheochromocytoma cell line PC12 cells in the presence of NGF. (

Original languageEnglish
Pages (from-to)1004-1008
Number of pages5
JournalEuropean Journal of Organic Chemistry
Issue number6
DOIs
Publication statusPublished - Jan 1 2003

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All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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