Abstract
Three new ganglioside molecular species, termed PNG-1, PNG-2A, and PNG-2B were isolated from pyloric caeca of the starfish Protoreaster nodosus. Their structures were elucidated using a combination of spectroscopic and chemical methods, and characterized as 1-O-[8-O-methyl-N-acetyl-α-neuraminosyl-(2→3)-β-galactopyranosyl]-ceramide for PNG-1, 1-O-[β-galactofuranosyl-(1→3)-α-galactopyranosyl-(1→4)-8-O-methyl-N-acetyl-α-neuraminosyl-(2→3)-β-galactopyranosyl]-ceramide for PNG-2A, and 1-O-[β-galactofuranosyl-(1→3)-α-galactopyranosyl-(1→9)-N-acetyl-α-neuraminosyl-(2→3)-β-galactopyranosyl]-ceramide for PNG-2B. PNG-2A and PNG-2B represent the first GM4 elongation products in nature.
Highlights
Gangliosides, sialic acid-containing glycosphingolipids (GLSs), are expressed in the outer leaflet of the plasma membrane of all vertebrate cells
The negative FAB-MS spectrum of PNG-1 showed a series of pseudo-molecular ion peaks [M − H]−
These data indicated that PNG-1 contained a disaccharide (OMeNeuAc-Hexose-Ceramide)
Summary
Gangliosides, sialic acid-containing glycosphingolipids (GLSs), are expressed in the outer leaflet of the plasma membrane of all vertebrate cells. Ganglioside research is still far from being considered concluded, but there is a general agreement to consider gangliosides as functional molecules involved in the modulation of enzyme properties, cell signaling, cell adhesion and protein sorting [3,4]. In contrast to their ubiquity in vertebrates, gangliosides are currently believed to be only present in the phylum Echinodermata within invertebrates. In a continuing investigation into GLS constituents of this animal, we isolated three new ganglioside molecular species and describe their structures in the present article
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