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

✍ Scribed by Valeria Costantino; Ernesto Fattorusso; Concetta Imperatore; Alfonso Mangoni; Roberta Teta

• Publisher: John Wiley and Sons
• Year: 2009
• Tongue: English
• Weight: 338 KB
• Volume: 2009
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200801230

✦ Synopsis

Abstract

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 Δ^6^‐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(1β→6)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)