Biologically active glycosides from asteroidea, XXV. Glycosphingolipids from the starfish Asterina pectinifera, 2. Structure of three ganglioside molecular species and a homogeneous ganglioside, and biological activity of the ganglioside

Abstract

AbstractThree ganglioside molecular species and a homogeneous ganglioside [GP‐1a (1), GP‐1b (2), GP‐2 (3) and asterinaganglioside A (4)] were obtained from the water‐soluble lipid fraction of the chloroform/methanol extract of the starfish Asterina pectinifera. On the basis of chemical and spectral evidence, the structure of 1–4 were elucidated. GP‐2 (3) was a known ganglioside molecular species, but the other three compounds were new gangliosides. Partial hydrolysis of oligosaccharide moieties with hot water was useful for structure elucidation of the gangliosides. NOE Correlation Spectroscopy (NOESY) was also useful for characterization of the complex sugar moiety. For the isolation of homogeneous ganglioside from the complex molecular species, reversed‐phase HPLC with methanol/ammonia/water as solvent was effective. Moreover, the main ganglioside molecular species, GP‐2 (3), was found to support the survival of cultured cerebral cortex cells, most of which were neuronal cells, of rat fetuses.