title: Bipinnatins K-Q, minor cembrane-type diterpenes from the West Indian Gorgonian Pseudopterogorgia kallos: isolation, structure assignment, and evaluation of biological activities.
abstract: An extensive chemical study of the secondary metabolites found in the crude organic extract of the gorgonian octocoral Pseudopterogorgia kallos has led to the isolation of seven new cembranolides, bipinnatins K-Q ( 2- 8), and one known compound, bipinnatin E ( 9). The molecular structures of compounds 2- 8, many of which contain unusual structural features, were assigned mainly by 2D NMR spectroscopic methods and X-ray crystallographic analysis. The discovery of compounds 2- 8 may lend support to previously proposed mechanisms for the biosynthesis of recently isolated bioactive natural products from the same gorgonian specimen. The in vitro cytotoxicity of bipinnatins 4, 6, and 7 against the NCI tumor cells MCF breast cancer, NCI-H460 non-small cell lung cancer, and SF-268 CNS cancer was evaluated. However, only bipinnatin Q ( 6) displayed significant cytotoxic activity. Some of the compounds isolated proved to be inhibitors of acetylcholine receptors.
authors.forename: Jeffrey
authors.initials: J
authors.lastname: Marrero
authors.forename: Jaime
authors.initials: J
authors.lastname: Benítez
authors.forename: Abimael D
authors.initials: AD
authors.lastname: Rodríguez
authors.forename: Hong
authors.initials: H
authors.lastname: Zhao
authors.forename: Raphael G
authors.initials: RG
authors.lastname: Raptis
mesh_terms: D000818:Animals; D037421:Anthozoa / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D017691:Caribbean Region; D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D005260:Female; D006801:Humans; D008968:Molecular Conformation; D015394:Molecular Structure; D009466:Neuromuscular Blocking Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D004224:Diterpenes; D009466:Neuromuscular Blocking Agents; C528882:bipinnatin Q