Additional Insights into the Obtusallene Family: Components of Laurencia marilzae

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 relevan...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2016-04, Vol.79 (4), p.1184-1188
Main Authors: Gutiérrez-Cepeda, Adrián, Fernández, José J, Norte, Manuel, López-Rodríguez, Matías, Brito, Iván, Muller, Christian D, Souto, María L
Format: Article
Language:English
Subjects:
Acetogenins - chemistry
Acetogenins - isolation & purification
Antineoplastic Agents - chemistry
Antineoplastic Agents - isolation & purification
Antineoplastic Agents - pharmacology
Apoptosis - drug effects
Cancer
Carcinoma, Hepatocellular - therapy
Crystallography, X-Ray
Ethers, Cyclic - chemistry
Human health and pathology
Humans
Hydrocarbons, Brominated - chemistry
Hydrocarbons, Brominated - isolation & purification
Hydrocarbons, Brominated - pharmacology
Hépatology and Gastroenterology
Laurencia - chemistry
Life Sciences
Molecular Conformation
Molecular Structure
Pharmaceutical sciences
Pharmacology
Spain
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Summary: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.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.5b01080