Constituents of Crinoidea. 2. Isolation and Structure of the Novel Type Gangliosides from the Feather Star Comanthus japonica

Abstract

Two novel type gangliosides CJP2 and CJP3 have been obtained from the feather star Comanthus japonica. On the basis of methylation linkage analysis combined with ammonolysis and other chemical and spectroscopic evidence, the chemical structures of CJP2 and CJP3 were determined to be α-9-O-Me-NeuGc-(2→3)-inositolphosphoceramide and α-9-O-Me-NeuGc-(2→11)-α-9-O-Me-NeuGc-(2→3)-inositolphosphoceramide, respectively. These gangliosides are unique in that they are inositolphosphoceramide derivatives possessing sialic acid; such gangliosides have not previously been identified. The presence of 9-O-methyl-N-glycolyl-neuraminosyl residues is also unique in naturally occurring gangliosides.