Isolation and structure of a GD3-Type ganglioside molecular species possessing neuritogenic activity from the starfish Luidia maculata.
A GD3-type ganglioside molecular species, LMG-4 (1), has been obtained from the polar lipid fraction of the chloroform/methanol extract of the starfish Luidia maculata. The structure of this ganglioside has been determined on the basis of chemical and spectroscopic evidence to be 1-O-[(N-acetyl-alpha-D-neuraminosyl)-(2-->8)-(N-acetyl-alpha-D-neuraminosyl)-(2-->3)-beta-D-galactopyranosyl-(1-->4)-beta-D-glucopyranosyl]-ceramide. The ceramide moiety was composed of heterogeneous 2-hydroxy fatty acid and phytosphingosine units. This is the first report on the isolation and structure elucidation of GD3-type ganglioside from echinoderms. Moreover, 1 exhibited neuritogenic activity toward the rat pheochromocytoma PC12 cells in the presence of nerve growth factor.
Faculty of Pharmaceutical Sciences, Kyushu University, Fukouka, Japan.
Satoshi
S
Kawatake
Masanori
M
Inagaki
Ryuichi
R
Isobe
Tomofumi
T
Miyamoto
Ryuichi
R
Higuchi
D000818:Animals; D002240:Carbohydrate Sequence; D002725:Chloroform / Q000737:chemistry; D005732:Gangliosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008055:Lipids / Q000737:chemistry; D000432:Methanol / Q000737:chemistry; D008969:Molecular Sequence Data; D016501:Neurites / Q000187:drug effects* / Q000378:metabolism; D016716:PC12 Cells; D051381:Rats; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013215:Starfish / Q000737:chemistry*
D005732:Gangliosides; D008055:Lipids; C026226:ganglioside, GD3; D002725:Chloroform; D000432:Methanol