Constituents of Holothuroidea, 18. Isolation and Structure of Biologically Active Disialo- and Trisialo-Gangliosides from the Sea Cucumber Cucumaria echinata

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Three new disialo- and trisialo-gangliosides, CEG-6 (6), CEG-8 (8), and CEG-9 (9), were obtained, together with one known ganglioside, HLG-3 (7), from the lipid fraction of the chloroform/methanol extract of the sea cucumber Cucumaria echinata. The structures of the new gangliosides were determined on the basis of chemical and spectroscopic evidence to be 1-O-[α-L-fucopyranosyl-(1→11)-(N-glycolyl-α-D-neuraminosyl)-(2→4)-(N-acetyl-α-D-neuraminosyl)-(2→6)-β-D-glucopyranosyl]-ceramide (6) and 1-O-[(N-glycolyl-D-neuraminosyl)-(2→11)-(N-glycolyl-D-neuraminosyl)-(2→4)-(N-acetyl-D-neuraminosyl)-(2→6)-D-glucopyranosyl]-ceramide (8, 9). The ceramide moieties of each compound were composed of an homogeneous sphingosine or phytosphingosine base and heterogeneous 2-hydroxy or nonhydroxylated fatty acid units. These gangliosides showed neuritogenic activity toward the rat pheochromocytoma cell line PC-12 in the presence of nerve growth factor.
公益社団法人日本薬学会の論文
2006-09-01