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

Helena Gaspar, Margherita Gavagnin, Gonçalo Calado, Francesco Castelluccio, Ernesto Mollo, Guido Cimino

Research output: Contribution to journalArticlepeer-review

36 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)11032-11037
Number of pages6
JournalTetrahedron
Volume61
Issue number46
DOIs
Publication statusPublished - 14 Nov 2005

Keywords

  • Marine metabolites
  • Molluscs
  • Terpenes and terpenoids

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