A New Furanose-Rich Pentaglycosylated GSL from the Sponge Terpios sp.

Marine organisms represent a prolific source of compounds with pharmacological properties. Among these our attention is paid to glycolipids from sponges. Many studies on glycolipids demonstrated their activity on the immune system1 and their influence on angiogenesis and tumor cells proliferation, and therefore they are potentially useful in the therapy against several diseases.Recent investigation of the glycosphingolipid (GSL) composition of the marine sponge Terpios sp. revealed the presence of terpioside A, the first diglycosylceramide having a L-fucofuranose unit in the sugar chain of the molecule. A further investigation of GSL composition of Terpios sp. showed the presence of Terpioside B, a new furanose-rich pentaglycosylated glycosphingolipid, characterized by the presence of two terminal α-L-fucofuranose units. The structure of terpioside B was elucidated using extensive 2D NMR and mass spectrometry studies. In addition, microscale chemical degradation was performed in order to establish the absolute configuration of the whole molecule as well as the length and the nature of the alkyl chains of the ceramide portion