Biotransformation of a dietary sesterterpenoid in the Mediterranean nudibranch Hypselodoris orsini

The metabolic relationship between the marine molluscHypselodoris orsini and the spongeCacospongia mollior has been reinvestigated. The predator-prey association has been confirmed even though the metabolic patterns of the two invertebrates are substantially different. Most probably the nudibranch converts the main sponge metabolite, the sesterterpenoid scalaradial (1), into a less oxygenated related metabolite, deoxoscalarin (4), followed by a second chemical transformation leading to a new sesterterpenoid, 6-keto-deoxoscalarin (5) which is selectively compartmentalized into some dorsal glands, mantle dermal formations (MDFs), strategically distributed near the gills. 6-keto-deoxoscalarin (5) has been characterized by 1D and 2D NMR methods. Finally, the unusual association of some Chromodorididae molluscs with sponges containing sesterterpenoids suggests a further analysis of their taxonomical collocation is required.