Oceanapiside, an Antifungal Bis-r,ö-amino Alcohol Glycoside from the Marine Sponge Oceanapia phillipensis

The structure of oceanapiside, an antifungal R,ö-bis-aminohydroxylipid glycoside from the temperate marine sponge Oceanapia sp., was elucidated by a combination of 2D NMR, chemical degradation/ correlation, and MALDI MS-MS spectrometry. Oceanapiside exhibits antifungal activity against Candida glabrata at 10 íg/mL (MIC). The structures of sphingolipids from marine inverte-brates share features of sphingolipids derived from plants and animals. In higher animals, the base is sphingosine (erythro-D-E-2-amino-4-octadecene-1,3-diol), while sphin-ganine (D-2-amino-octadecan-1,3-diol) is most common in plant sphingolipids.1 A significant departure from this motif is found in the structures of dimeric amino alcohol bases from certain calcareous sponges. Leucettamols A (1) and B, from Leucetta sp.;2 compound BRS1, from an unidentified sponge;3 rhizochalin (2), from Rhizochalina incrustata,4 and related compounds; coriacenins, from th