Isolation and Structure of a Monomethylated Ganglioside Possessing Neuritogenic Activity from the Ovary of the Sea Urchin Diadema setosum

Koji Yamada; Kaoru Tanabe; Tomofumi Miyamoto; Toshihide Kusumoto; Masanori Inagaki; Ryuichi Higuchi

doi:10.1248/cpb.56.734

Notes

Isolation and Structure of a Monomethylated Ganglioside Possessing Neuritogenic Activity from the Ovary of the Sea Urchin Diadema setosum

Koji Yamada, Kaoru Tanabe, Tomofumi Miyamoto, Toshihide Kusumoto, Masanori Inagaki, Ryuichi Higuchi

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Keywords: ganglioside, sea urchin, Diadema setosum, neuritogenic activity

JOURNAL FREE ACCESS

2008 Volume 56 Issue 5 Pages 734-737

DOI https://doi.org/10.1248/cpb.56.734

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Abstract

A new monomethylated ganglioside, DSG-A (3), was obtained, together with four known gangliosides, compounds (1, 2, 4, 5), from the lipid fraction of the chloroform/methanol extract of the ovary of the sea urchin Diadema setosum. The structures of the new ganglioside was determined on the basis of chemical and spectroscopic evidence to be 1-O-[9-O-methyl-(N-acetyl-α-D-neuraminosyl)-(2→6)-β-D-glucopyranosyl]-ceramide (3). The ceramide moiety of 3 was composed of C₁₈-phytosphingosine base, and 2-hydroxy and nonhydroxylated fatty acid units. These gangliosides showed neuritogenic activity toward the rat pheochromocytoma cell line PC-12 in the presence of nerve growth factor, in which compound 3 showed the most potent activity.

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