3-Hydroxy Fatty Acids and Methyl Esters

3-Hydroxy fatty acid monomers are the components of polyhydroxyalkenoates, polyesters produced by bacteria fermentation that are used for carbon and energy storage and are of interest in studies regarding bacterial synthesis, properties, and mechanisms. It has been suggested that the methyl ester of 3-hydroxy acid is an intercellular signal that auto-regulates virulence gene expression¹ and that it modulates production of PhcA-regulated virulence factors in Ralstonia (Pseudomonas) solanacearum. 3-Hydroxy fatty acids have been found to be converted to the omega-fatty acid by the enzyme CYP4F11 and then into dicarboxylic acids in vivo.² They are used as biomarkers for fatty acid oxidative disorders of both the long- and short-chain 3-hydroxy-acyl-CoA dehydrogenases.^3,4

References:

1. A. Flavier et al. “Identification of 3-hydroxypalmitic acid methyl ester as a novel autoregulator controlling virulence in Ralstonia solanacearum” Mol Microbiol, vol. 26 pp. 251-259, 1997
2. M. Dhar et al. “Omega oxidation of 3-hydroxy fatty acids by the human CYP4F gene subfamily enzyme CYP4F11” Journal of Lipid Research, vol. 49, pp. 612-624, 2008
3. P. Jones et al. “Improved Stable Isotope Dilution-Gas Chromatography-Mass Spectrometry Method for Serum or Plasma Free 3-Hydroxy-Fatty Acids and Its Utility for the Study of Disorders of Mitochondrial Fatty Acid beta-Oxidation” Clinical Chemistry, vol. 46, pp. 149-155, 2000
4. P. Jones et al. “Accumulation of free 3-hydroxy fatty acids in the culture media of fibroblasts from patients deficient in long-chain l-3-hydroxyacyl-CoA dehydrogenase: a useful diagnostic aid” Clinical Chemistry, vol. 47(7) pp. 1190-1194, 2001