Constituents of Holothuroidea.10.^<1)>Isolation and Structure of a Biologically Active Ganglioside Molecular Species from the Sea Cucumber Holothuria leucospilota

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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-α-_D-neuraminosyl)-(2→6)-β-_D-glucopyranosyl]-ceramide(1), 1-O-[(N-glycolyl-α-_D-neuraminosyl)-(2→4)-(N-acetyl-1-α-_D-neuraminosyl)-(2→6)-β-_D-glucopyranosyl]-ceramide(2)and 1-O-[α-_L-fucopyranosyl-(1→11)-(N-glycolyl-α-_D-neuraminosyl)-(2→4)-(N-acetyl-1-α-_D-neuraminosyl)-(2→6)-β-_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).
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2001-04-01