Constituents of Crinoidea. 3. Isolation and Structure of a Glycosyl Inositolphosphoceramide-Type Ganglioside with Neuritogenic Activity from the Feather Star Comanthus japonica

Abstract

A glycosyl inositolphosphoceramide-type ganglioside, CJP4, was obtained from the polar lipid fraction of the chloroform/methanol extract of the feather star Comanthus japonica. The structure of this ganglioside has been determined on the basis of chemical and spectroscopic evidence to be 9-O-methyl-(N-glycolyl-α-D-neuraminosyl)-(2→11)-9-O-methyl-(N-glycolyl-α-D-neuraminosyl)-(2→11)-9-O-methyl-(N-glycolyl-α-D-neuraminosyl)-(2→3)-inositolphosphoceramide, which contains C₁₆-sphingosine and C_22:0-, C_24:0-fatty acid. This is the first report on the isolation and structural elucidation of a trisialo-glycosyl inositolphosphoceramide-type ganglioside. Moreover, CJP4 exhibited neuritogenic activity toward the rat pheochromocytoma PC12 cells in the presence of nerve growth factor.