Biologically Active Glycosides from Asteroidea, 42. Isolation and Structure of a New Biologically Active Ganglioside Molecular Species from the Starfish Asterina pectinifera

• Published in: Chemical & pharmaceutical bulletin Vol. 54; no. 3; pp. 287 - 291
• Main Authors: Higuchi, Ryuichi, Inoue, Shinichi, Inagaki, Kouji, Sakai, Maki, Miyamoto, Tomofumi, Komori, Tetsuya, Inagaki, Masanori, Isobe, Ryuichi
• Format: Journal Article
• Language: English
• Published: Japan The Pharmaceutical Society of Japan 01.03.2006; Japan Science and Technology Agency
• Subjects: Acetates - chemistry; Animals; Asterina pectinifera; Carbohydrate Sequence; Chromatography, Thin Layer; ganglioside; Gangliosides - chemistry; Gangliosides - isolation & purification; Gas Chromatography-Mass Spectrometry; Glycoside Hydrolases - chemistry; Glycosides - chemistry; Glycosides - isolation & purification; glycosphingolipid; Hydrolysis; Magnetic Resonance Spectroscopy; Methylation; Molecular Sequence Data; Nerve Growth Factor - pharmacology; Neurites - drug effects; neuritogenic activity; PC12 Cells; Rats; Spectrophotometry, Infrared; starfish; Starfish - physiology; Sugar Alcohols - chemistry
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.54.287

A ganglioside molecular species GP-3 (1) has been obtained from the water-soluble lipid fraction of the chloroform/methanol extract of the starfish Asterina pectinifera. The structure of the ganglioside has been determined on the basis of chemical and spectroscopic evidence. Compound 1 represents new ganglioside molecular species possessing two moles of sialic acids at the inner part of the sugar moiety. Partial hydrolysis by hot water and an enzymatic hydrolysis by means of endoglycoceramidase (EGCase) have proved useful for structure elucidation of the complex oligosaccharide moiety. Moreover, 1 exhibits neuritogenic activity toward the rat pheochromocytoma cell line, PC-12 cells, in the presence of nerve growth factor (NGF).