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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-&amp;#945;-neuraminosyl-(2&amp;#8594;3)-&amp;#946;-galactopyranosyl]-ceramide for PNG-1, 1-O-[&amp;#946;-galactofuranosyl-(1&amp;#8594;3)-&amp;#945;-galactopyranosyl-(1&amp;#8594;4)-8-O-methyl-N-acetyl-&amp;#945;-neuraminosyl-(2&amp;#8594;3)-&amp;#946;-galactopyranosyl]-ceramide for PNG-2A, and 1-O-[&amp;#946;-galacto furanosyl-(1&amp;#8594;3)-&amp;#945;-galactopyranosyl-(1&amp;#8594;9)-N-acetyl-&amp;#945;-neuraminosyl-(2&amp;#8594;3)-&amp;#946;-galactopyr anosyl]-ceramide for PNG-2B. PNG-2A and PNG-2B represent the first GM4 elongation products in nature.

Isolation and Structure Elucidation of GM4-Type Gangliosides from the Okinawan Starfish Protoreaster nodosus