Constituents of holothuroidea. 10. Isolation and structure of a biologically active ganglioside molecular species from the sea cucumber Holothuria leucospilota

Citation
K. Yamada et al., Constituents of holothuroidea. 10. Isolation and structure of a biologically active ganglioside molecular species from the sea cucumber Holothuria leucospilota, CHEM PHARM, 49(4), 2001, pp. 447-452
Citations number
12
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry & Analysis
Journal title
CHEMICAL & PHARMACEUTICAL BULLETIN
ISSN journal
0009-2363 → ACNP
Volume
49
Issue
4
Year of publication
2001
Pages
447 - 452
Database
ISI
SICI code
0009-2363(200104)49:4<447:COH1IA>2.0.ZU;2-D
Abstract
Three ganglioside molecular species, HLG-1 (1), HLG-2 (2), and HLG-3 (3) ha ve been obtained from the lipid fraction of the chloroform/methanol extract of the sea cucumber Holothuria leucospilota. The structures of these gangl iosides have been determined, on the basis of chemical and spectroscopic ev idence, as 1-O-[(N-gly- colyl-alpha -D-neuraminosyl)-(2 -->6)-beta -D-gluco pyranosyl] -ceramide (1), 1-O-[(N-glycolyl-alpha -D-neuraminosyl)-(2 -->4)- (N-acetyl-alpha -D-neuramino syl)-(2 -->6)-beta -D-glucopyranosyl]-ceramid e (2) and 1-O-[alpha -L-fucopyranosyl-(1 --> 11)-(N- glycolyl-alpha -D-neur aminosyl)-(2 -->4)-(N-acetyl-alpha -D-neuraminosyl)-(2 -->6)-beta -D-glucop yranosyl]-ceramide (3). The ceramide moieties were composed of heterogeneou s phytosphingosine, sphingosine and 2-hydroxy fatty acid units. Compounds 2 and 3 represent new ganglioside molecular species. These three ganglioside molecular species showed neuritogenic activity toward the rat pheochromocy toma cell line, PC-12 cell, in the presence of NGF (nerve growth factor).