Glycolipids from sponges. 19. Terpioside from the marine sponge Terpios sp., the first glycosphingolipid having an L-fucofuranose unit

The new diglycosylceramide terpioside has been isolated from the marine sponge Terpios sp. Terpioside is a diglycosylated glycosphingolipid which is the first example of a natural glycosphingolipid having an L-fucofuranose unit. The structure of terpioside was elucidated by extensive spectroscopic analysis, whereas chemical degradation was used to establish the nature of the alkyl chains and the absolute configuration of the sugars and of the ceramide stereogenic centers.