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

Research output: Contribution to journalArticle

19 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)734-738
Number of pages5
JournalChemical and Pharmaceutical Bulletin
Volume56
Issue number5
DOIs
Publication statusPublished - May 19 2008

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Sea Urchins
Gangliosides
Ovary
phytosphingosine
Ceramides
PC12 Cells
Nerve Growth Factor
Chloroform
Methanol
Rats
Fatty Acids
Cells
Lipids
ceramide 3

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Drug Discovery

Cite this

Isolation and structure of a monomethylated ganglioside possessing neuritogenic activity from the ovary of the sea urchin Diadema setosum. / Yamada, Koji; Tanabe, Kaoru; Miyamoto, Tomofumi; Kusumoto, Toshihide; Inagaki, Masanori; Higuchi, Ryuichi.

In: Chemical and Pharmaceutical Bulletin, Vol. 56, No. 5, 19.05.2008, p. 734-738.

Research output: Contribution to journalArticle

Yamada, Koji ; Tanabe, Kaoru ; Miyamoto, Tomofumi ; Kusumoto, Toshihide ; Inagaki, Masanori ; Higuchi, Ryuichi. / Isolation and structure of a monomethylated ganglioside possessing neuritogenic activity from the ovary of the sea urchin Diadema setosum. In: Chemical and Pharmaceutical Bulletin. 2008 ; Vol. 56, No. 5. pp. 734-738.
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