Additional Insights into the Obtusallene Family: Components of Laurencia marilzae

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• 作者：Adrián Gutiérrez-Cepeda ; José J. Fernández ; Manuel Norte ; Matías López-Rodríguez ; Iván Brito ; Christian D. Muller ; María L. Souto
• 刊名：Journal of Natural Products
• 出版年：2016
• 出版时间：April 22, 2016
• 年：2016
• 卷：79
• 期：4
• 页码：1184-1188
• 全文大小：295K
• 年卷期：0
• ISSN：1520-6025

文摘

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.