12- Methyltetradecanoic acid

Human lung cancer cells and human prostate cancer cells were implanted into athymic nude mice, then harvested and implanted in the lung and prostate, respectively, of a MetaMouse orthotopic model. Feeding 13-MTDA for 40 days inhibited the growth of lung cancer implants by 65% and prostate cancer implants by 85% compared to control animals (Yang et al., 2000). 

Recently, Wongtangtintharn et al. (2004) showed that a series of iso- and animo-branched-chain fatty acids was cytotoxic to breast cancer cells. The highest activity was observed with iso-Ci o and the activity decreased as the chain-length increased or decreased from Ci6 o. Cytotoxicity of branched-chain fatty acids was comparable to that of RA and tram-10, a. v-12-C X 2. 

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Yang, Z., Liu, S., Chen, X., Chen, H., Huang, M., Zheng, J. 2000. Induction of apoptotic cell death and in vivo growth inhibition of human cancer cells by a saturated branched-chain fatty acid, 13-methyltetradecanoic acid. Can. Res. 60, 505-509. 

BCFAs make up the major proportion of fatty acids in the lipid extract from certain bacteria, such as bacilli [2]. Biosynthesis of BCFAs occurs with the branched-chain amino acids as primary precursors and malonyl-CoA (coenzyme A) as the chain extender (Figure 18.1). These BCFAs biosynthesized by bacteria and included in fermented food may contribute to the food s regulation of cell biology or metabolism [3-5]. A saturated BCFA, 13-methyltetradecanoic acid (13-MTD), was purified from a fermented soy product as an antitumor compound [6]. A BCFA was also found to induce apoptotic cell death in human cancer cells [6]. In this review, we describe the biological activities of BCFAs, with special reference to 13-MTD. 

In the course of screening for inhibitors of cyclic adenosine-3, 5 -monophosphate phosphodiesterase, a strain of B. subtilis was found to produce a series of such inhibitors. These compounds with a m.p. of 136-139 °C and an optical rotation of -h 37° to 38.5° (chloroform), — 33° to — 38° (methanol), were lipopeptides with the same peptide moiety as surfactin. Their fatty acid components were 3-hydroxy-ll-methyldodecanoic acid, 3-hydroxy-10-methyldodecanoic add, 3-hydroxytetradecanoic acid (the major component), 3-hydroxy-13-methyltetradecanoic acid (the same acid as that of surfactin) and 3-hydroxy-12-methyltetradecanoic acid (707, 702). The location of the lactone ring was established by the same method as that used for surfactin 96), Therefore these inhibitors had structures quite similar to, and for one of them identical with, that of surfactin (40). 

Carballeira, N.M., Cruz, H Orellano, E.A., and Gonzalez, F.A. (2003) The first total synthesis of the marine fatty acid ( )-2-methoxy-13-methyltetradecanoic acid a cytotoxic fatty acid to leukemia cells. Chem. Phys. Lipids, 126,149-153. 

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