Studies on the Glycosphingolipids of the Starfish, Asterina pectinifera

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Abstract
Three gangliosides, provisionally named Gangliosides 1, 2, and 3, were obtained from the lipid extract of the starfish, Asterina pectinifera by silicic acid, DEAE-Sephadex, and Iatrobeads column chromatography. The most abundant, Ganglioside 3 (37.7 μg/g wet weight of starfish) was isolated in the pure state and its chemical structure was studied. The sugar composition of Ganglioside 3 consisted of arabinose, glucose, galactose, and sialic acid (as N-glycolylneuraminic acid) in a molar ratio of 1: 1: 3: 1. Three sialic acid-containing oligosaccharide fragments were isolated from partial acid hydrolysates of the ganglioside by Dowex 1 × 8 (acetate form) column chromatography and preparative paper chromatography, and identified as Gal→NeuGc, Gal(1→4)[Gal(1→8)]NeuGc and Ara-(1→6)Gal(1→4)[Gal(1→8)] NeuGc. The structure of Ganglioside 3 was postulated to be: Araf, p(1→6)Galp, β(1→4)[Galpβ(l→8)]NeuGc(2→3)Galpβ(1→4)Glcpβ(1→1)-ceramide. This is a unique structure with the sialic acid residue internally located in the sugar chain. The ganglioside contained saturated 2-hydroxy fatty acids ranging in length from C16 to C21, among which C22, C23 and C24 acids were predominant. The long-chain bases consisted exclusively of C16, C17 and C18 phytosphingosines of iso and anteiso types.