The Agminosides: Naturally Acetylated Glycolipids from the New Zealand Marine Sponge Raspailia agminata

Examination of the New Zealand sponge Raspailia agminata resulted in the isolation of five members of a novel family of glycolipids, agminosides A-E (1-5). These large and complex molecules contain up to six partially acetylated glucose residues. The chromatographic separation of these compounds was a challenge due to the similarity of the congeners and their lack of a chromophore. MS-guided isolation followed by extensive NMR analysis and chemical derivatization eventually led to the purification and identification of 1-5.