Constituents of holothuroidea. 10. Isolation and structure of a biologically active ganglioside molecular species from the sea cucumber Holothuria leucospilota.
Three ganglioside molecular species, HLG-1 (1), HLG-2 (2), and HLG-3 (3) have been obtained from the lipid fraction of the chloroform/methanol extract of the sea cucumber Holothuria leucospilota. The structures of these gangliosides have been determined, on the basis of chemical and spectroscopic evidence, as 1-O-[(N-glycolyl-alpha-D-neuraminosyl)-(2-->6)-beta-D-glucopyranosyl]-ceramide (1), 1-O-[(N-glycolyl-alpha-D-neuraminosyl)-(2-->4)-(N-acetyl-alpha-D-neuraminosyl)-(2-->6)-beta-D-glucopyranosyl]-ceramide (2) and 1-O-[alpha-L-fucopyranosyl-(1-->11)-(N-glycolyl-alpha-D-neuraminosyl)-neuraminosyl)-(2-->4)-(N-aetyl-alpha-D-neuraminosyl)-(2-->6)-beta-D-glucopyranosyl]-ceramide (3). The ceramide moieties were composed of heterogeneous 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 pheochromocytoma cell line, PC-12 cell, in the presence of NGF (nerve growth factor).
Yamada
K
K
Faculty of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan.
Matsubara
R
R
Kaneko
M
M
Miyamoto
T
T
Higuchi
R
R
D000818:Animals; D002240:Carbohydrate Sequence; D002855:Chromatography, Thin Layer; D004187:Disaccharides / Q000737:chemistry; D004447:Echinodermata / Q000737:chemistry*; D005732:Gangliosides / Q000302:isolation & purification / Q000494:pharmacology*; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008968:Molecular Conformation; D008969:Molecular Sequence Data; D009416:Nerve Regeneration / Q000187:drug effects*; D016501:Neurites / Q000187:drug effects; D016716:PC12 Cells; D051381:Rats; D016339:Spectrometry, Mass, Fast Atom Bombardment
C432904:1-O-((N-glycolylneuraminosyl)-(2-4)-(N-acetylneuraminosyl)-(2-6)glucopyranosyl)ceramide; C432885:1-O-((N-glycolylneuraminosyl)-(2-6)-glucopyranosyl)ceramide; C432905:1-O-((fucopyranosyl-(1-11)-(N-glycolylneuraminosyl)neuraminosyl)-(2-4)-(N-aetylneuraminosyl)-(2-6)-glucopyranosyl)ceramide; D004187:Disaccharides; D005732:Gangliosides