Additional Insights into the Obtusallene Family: Components of Laurencia marilzae.
Fiche publication
Date publication
avril 2016
Journal
Journal of natural products
Auteurs
Membres identifiés du Cancéropôle Est :
Dr MULLER Christian
Tous les auteurs :
Gutiérrez-Cepeda A, Fernández JJ, Norte M, López-Rodríguez M, Brito I, Muller CD, Souto ML
Lien Pubmed
Résumé
The obtusallenes are a significant subset of C15-halogenated acetogenins that incorporate 12-membered cyclic ethers. We have recently reported the isolation from Laurencia marilzae of 12-epoxyobtusallene IV (1) and its related α,β-unsaturated carboxylate ester (2), both of special biogenetic relevance. Here we describe the final step of our study, the isolation of three new analogues (3-5), among these, the first bromopropargylic derivative (3) of this class of macrocyclic C15-acetogenins. The structures were elucidated by analysis of NMR and X-ray data. 12-Epoxyobtusallene IV (1), its new isomer 4, and known obtusallene IV (6) were evaluated for their apoptosis-inducing activities in a human hepatocarcinoma cell line.
Mots clés
Acetogenins, chemistry, Antineoplastic Agents, chemistry, Apoptosis, drug effects, Carcinoma, Hepatocellular, therapy, Crystallography, X-Ray, Ethers, Cyclic, chemistry, Humans, Hydrocarbons, Brominated, chemistry, Laurencia, chemistry, Molecular Conformation, Molecular Structure, Spain
Référence
J. Nat. Prod.. 2016 Apr 22;79(4):1184-8