Pelseneeriol-1 and -2: new furanosesquiterpene alcohols from porostome nudibranch Doriopsilla pelseneeri

Abstract

The paper reports the first chemical study of the porostome nudibranch Doriopsilla pelseneeri collected off the Portuguese coast (Atlantic Ocean). Two new furanosesquiterpene alcohols, pelseneeriol-1 ( 1 ) and pelseneeriol-2 ( 2 ), have been isolated together with known compounds, 15-acetoxy- ent-pallescensin-A ( 5 ), and dendocarbin-A ( 6 ), from the mantle of the nudibranch, whereas euryfuran ( 3 ) and drimane ester mixture 4 were identified in the extract of the internal glands. The structures of 1 and 2 have been determined by extensive spectroscopic studies as well as by comparison with literature model compounds. In order to assess the relative stereochemistry of 1 and 2 , full NMR assignment of related sponge metabolite microcionin-2 ( 8 ) and of co-occurring sesquiterpenes 9– 11 , that have been re-isolated from the Mediterranean sponge Fasciospongia cavernosa, has been also conducted. In particular, the relative stereochemistry of tricyclic sesquiterpene microcionin-1 ( 9 ) has now been rigorously assigned by detailed analysis of NOE difference experiments.