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 journalArticlepeer-review

22 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

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Drug Discovery

Fingerprint Dive into the research topics of 'Isolation and structure of a monomethylated ganglioside possessing neuritogenic activity from the ovary of the sea urchin Diadema setosum'. Together they form a unique fingerprint.

Cite this