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

• Published in: Chemical & Pharmaceutical Bulletin Vol. 56; no. 5; pp. 734 - 737
• Main Authors: Yamada, Koji, Tanabe, Kaoru, Miyamoto, Tomofumi, Kusumoto, Toshihide, Inagaki, Masanori, Higuchi, Ryuichi
• Format: Journal Article
• Language: English; Japanese
• Published: TOKYO The Pharmaceutical Society of Japan 01.05.2008; Pharmaceutical Society of Japan; Pharmaceutical Soc Japan; Japan Science and Technology Agency
• Subjects: Animals; Carbohydrate Conformation; Carbohydrate Sequence; Cell Proliferation - drug effects; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; Diadema setosum; Echinoidea; Female; ganglioside; Gangliosides - chemistry; Gangliosides - pharmacology; Gas Chromatography-Mass Spectrometry; Life Sciences & Biomedicine; Methanol - chemistry; Methylation; Molecular Sequence Data; Neurites - drug effects; neuritogenic activity; Ovary - chemistry; PC12 Cells; Pharmacology & Pharmacy; Physical Sciences; Rats; Science & Technology; sea urchin; Sea Urchins; Solvents; Spectrometry, Mass, Fast Atom Bombardment; Spectrophotometry, Infrared; Spectroscopy, Fourier Transform Infrared; GLYCOSIDES; GLYCOSPHINGOLIPIDS; Diadema setosum; neuritogenic activity; BIOLOGICAL-ACTIVITY; ASTEROIDEA; ANTHOCIDARIS-CRASSISPINA; sea urchin; ganglioside; EMBRYOS; EGGS; CONSTITUENTS
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.56.734

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.