Amphiceramide A and B, Novel Glycosphingolipids from the Marine Sponge Amphimedon compressa

Glycolipid analysis of the Caribbean sponge Amphimedon compressa has shown it to contain two novel glycosphingolipids, amphiceramide A (1a) and B (2a), which possess an unusual Δ6-phytosphingosine. The saccharide chain of amphiceramide A is composed of a β-glucose residue glycosylated at the 6-position by an N-acetyl-β-glucosamine and has never been found before in a natural product. The saccharide chain of amphiceramide B consists of an allolactose [Gal(1β6)Glc] residue β-linked to the ceramide and is found here for the first time in a natural glycosphingolipid. In addition, the sponge contains a new molecular species, acetamidoglucosyl ceramide (3a), and the known glucosyl ceramide 4a (halicerebroside A) and melibiosyl ceramide 5a (amphimelibioside C). (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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