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. 2011 Feb;164(2):113-7.
doi: 10.1016/j.chemphyslip.2010.11.006. Epub 2010 Dec 1.

First total synthesis and antileishmanial activity of (Z)-16-methyl-11-heptadecenoic acid, a new marine fatty acid from the sponge Dragmaxia undata

Néstor M Carballeira  1 , Nashbly Montano, Gabriel A Cintrón, Carmary Márquez, Celia Fernández Rubio, Christopher Fernández Prada, Rafael Balaña-Fouce
Affiliations

First total synthesis and antileishmanial activity of (Z)-16-methyl-11-heptadecenoic acid, a new marine fatty acid from the sponge Dragmaxia undata

Néstor M Carballeira et al. Chem Phys Lipids. 2011 Feb.

Abstract

The first total synthesis for the (Z)-16-methyl-11-heptadecenoic acid, a novel fatty acid from the sponge Dragmaxia undata, was accomplished in seven steps and in a 44% overall yield. The use of (trimethylsilyl)acetylene was key in the synthesis. Based on a previous developed strategy in our laboratory the best synthetic route towards the title compound was first acetylide coupling of (trimethylsilyl)acetylene to the long-chain protected 10-bromo-1-decanol followed by a second acetylide coupling to the short-chain 1-bromo-4-methylpentane, which resulted in higher yields. Complete spectral data is also presented for the first time for this recently discovered fatty acid and the cis double bond stereochemistry of the natural acid was established. The title compound displayed antiprotozoal activity against Leishmania donovani (IC(50) = 165.5 ± 23.4 μM) and inhibited the leishmania DNA topoisomerase IB enzyme (LdTopIB) with an IC(50) = 62.3 ± 0.7 μM.

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Figures

Fig. 1
Fig. 1
Mass spectrum (70 eV) of methyl (Z)-16-methyl-11-heptadecenoate.
Fig. 2
Fig. 2
Plots of percent (%) of living L. donovani promastigotes (A) and living percent of murine macrophages (B) versus concentrations (µM) of the fatty acid 1. The calculated therapeutic index (IC50/IC50) for fatty acid 1 is 3.7.
Scheme 1
Scheme 1
Synthesis of (Z)-16-methyl-11-heptadecenoic acid (1).
See this image and copyright information in PMC

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