np5b01080_si_002.cif (21.75 kB)
Additional Insights into the Obtusallene Family: Components of Laurencia marilzae
dataset
posted on 2016-03-11, 12:49 authored by Adrián Gutiérrez-Cepeda, José J. Fernández, Manuel Norte, Matías López-Rodríguez, Iván Brito, Christian
D. Muller, María L. SoutoThe 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.