TY - JOUR
T1 - Structure of a new neuritogenic-active ganglioside from the sea cucumber Stichopus japonicus
AU - Kaneko, Masafumi
AU - Kisa, Fumiaki
AU - Yamada, Koji
AU - Miyamoto, Tomofumi
AU - Higuchi, Ryuichi
PY - 2003/3
Y1 - 2003/3
N2 - 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. (
AB - 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. (
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U2 - 10.1002/ejoc.200390141
DO - 10.1002/ejoc.200390141
M3 - Article
AN - SCOPUS:0037353426
SN - 1434-193X
SP - 1004
EP - 1008
JO - Justus Liebigs Annalen der Chemie
JF - Justus Liebigs Annalen der Chemie
IS - 6
ER -