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Pintoxolanes A–C, Highly Functionalized 3,14‐Oxa‐bridged Cembranoids from the Caribbean Gorgonian Coral Eunicea pinta
Author(s) -
Figueroa Janet,
Vera Brunilda,
Rodríguez Abimael D.
Publication year - 2014
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201300282
Subject(s) - gorgonian , moiety , chemistry , coral , stereochemistry , biogenesis , terpene , biochemistry , gene , art , visual arts
Three new cembrane‐based diterpenes possessing the rare 3,14‐oxa‐bridged moiety were isolated from the hexane extract of a southwestern Caribbean gorgonian octocoral, Eunicea pinta , together with seven known cembranoid diterpenes. The structures of pintoxolanes A–C ( 1 – 3 , resp.), including their relative configurations, were deduced from spectroscopic data and chemical‐correlation experiments. Experimental evidence hinting to a plausible biogenesis of the 3,14‐oxalane moiety is provided. Preliminary cytotoxicity data for compounds 1 – 3 toward human cancer cell lines are also provided.