Identification of (e)‐11‐hydroxy‐9‐octadecenoic acid and (E)‐9‐hydroxy‐10‐octadecenoic acid by biotransformation of oleic acid by Pseudomonas sp. 32T3

Abstract

Pseudomonas sp. 32T3, a newly identified strain originally isolated from a vegetable oil-contaminated soil, produces three monohydroxy acids-(E)-11-hydroxy-9-octadecenoic acid, (E)-10-hydroxy-8-octadecenoic acid, and (E)-9-hydroxy-10-octadecenoic acid-as bioconversion products of oleic acid. The bacterial cells were grown in a mineral medium containing oleic acid as the main carbon substrate. The compounds were identified as the corresponding methyl esters on the basis of their chromatographic and spectroscopic ( 1 H and 13 C nuclear magnetic resonance and gas chromatography-mass spectrometry) features.Paper no. J9784 in JAOCS 78, 593-597 (June 2001).

Anti-inflammatory Constituents of the Red Alga Gracilaria verrucosa and Their Synthetic Analogues

“…Compounds 7 and 12 – 14 , identified as saturated keto fatty acids, were previously prepared from biotransformation or isolated from a few higher plants. – From the CID spectra of [M − H + 2Na] + ions of these compounds, the β ion of 7 , 12 , 13 , and 14 was observed at m / z 187, 187, 201, and 215, respectively, whereas the γ′ ion of 7 , 12 , 13 , and 14 was found at m / z 257, 257, 271, and 285, respectively. These diagnostic ions led to the identification of the position of the keto group at C-10 for 7 and 12 , C-11 for 13 , and C-12 for 14 .…”

“…Scheme 2 outlines the synthetic path of the brominated and phenyl-substituted derivatives. The brominated analogues (29)(30)(31)(32)(33)(34)(35)(36) were formed by the bromination of the enone fatty acids (15-19, 9, 10, and 20) using Br 2 in CCl 4 followed by base-catalyzed elimination. Subsequent Suzuki coupling of some brominated compounds (29, 31, 35, and 36) with phenylboronic acid mediated by tetrakis(triphenylphosphine)palladinium(0) afforded the corresponding phenyl-substituted analogues (37)(38)(39)(40).…”

Identification of oxylipins with antifungal activity by LC–MS/MS from the supernatant of Pseudomonas 42A2

“…Plants are the main suppliers of hydroxy fatty acids, with castor oil the most common; due to the variety of possible industrial applications of ricinoleic acid, research has been done to find the best method to produce engineered castor oil (Naughton, 1974;Kinney, 2002). In microorganisms hydroxy fatty acids are produced from the biotransformation of unsaturated fatty acids (Culleré et al, 2001;Rodríguez et al, 2001;Kuo et al, 2002). Such compounds belong to a class of oxylipins with antifungal activity which have been found in Oryza sativa plants resistant to rice blast disease, and isolated from timothy plants infected by the fungus Epichloe typhina ( Kato et al, 1988).…”

Production of (E) 10-Hydroxy-8-octadecenoic Acid with Lyophilized Microbial Cells

“…As an example, three different unsaturated monohydroxy derivatives of oleic acid (11-hydroxy-9-octadecenoic, 10-hydroxy-8-octadecenoic and 9-hydroxy-10-octadecenoic acids) are produced when Pseudomonas sp. 32T3 grows in a mineral medium with oleic acid as the main carbon substrate [4]. It has been reported that the microbial oxidation of oleic acid with Pseudomonas sp.…”