Glycolipids from sponges, 14. Vesparioside from the marine sponge Spheciospongia vesparia, the first diglycosylceramide with a pentose sugar residue

The marine sponge Spheciospongia vesparia produces vesparioside (1a), a diglycosylated glycosphingolipid which is the first example of a natural diglycosylceramide with a pentose sugar residue. The structure of vesparioside was mostly determined by extensive spectroscopic analysis but determination of the nature of the alkyl chains and elucidation of the absolute stereochemistry of the sugars and of theceramide required chemical degradation. In this respect, an improved and simplified procedure for the microscale chemical degradation of glycosphingolipids was employed here for the first time.