Production of 10,12-dihydroxy-8(E)-octadecenoic acid, an intermediate in the conversion of ricinoleic acid to 7,10,12-trihydroxy-8(E)-octadecenoic acid by Pseudomonas aeruginosa PR3 |
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Authors: | H Kim T M Kuo C T Hou |
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Institution: | (1) Oil Chemical Research, National Center for Agricultural Utilization Research, ARS, USDA, Peoria, IL 61604, USA, US |
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Abstract: | A bacterial isolate, Pseudomonas aeruginosa (PR3), has been reported to produce a new compound, 7,10,12-trihydroxy-8(E)-octadecenoic acid (TOD), from ricinoleic acid (Kuo TM, LK Manthey and CT Hou. 1998. J Am Oil Chem Soc 75: 875–879). The
reaction is unique in that it involves an introduction of two additional hydroxyl groups at carbon 7 and 10 and a rearrangement
of the double bond from carbon 9–10 (cis) to 8–9 (trans). In an effort to elucidate the metabolic pathway involved in the formation of TOD from ricinoleic acid by PR3, we have isolated
another compound from the reaction mixture using HPLC. The structure of the new compound was determined to be 10, 12-dihydroxy-8(E)-octadecenoic acid (DHOD) by GC/MS, FTIR, and NMR. The structural similarity between DHOD and TOD and the results from the
time course study of the above two compounds strongly suggested that DHOD was an intermediate in the bioconversion of ricinoleic
acid to TOD by PR3. The optimum pH and temperature for the production of DHOD from ricinoleic acid by PR3 was 6.5 and 25°C,
respectively. This is the first report on the production of 10,12-dihydroxy-8(E)-octadecenoic acid from ricinoleic acid by PR3. Journal of Industrial Microbiology & Biotechnology (2000) 24, 167–172.
Received 28 July 1999/ Accepted in revised form 18 November 1999 |
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Keywords: | : biotransformation dihydroxy octadecenoic acid trihydroxy octadecenoic acid Pseudomonas aeruginosa ricinoleic acid hydroxylation |
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