Microbial production of a novel trihydroxy unsaturated fatty acid from linoleic acid.
A bacterium isolated from a dry soil sample collected from McCalla, AL, USA, converted linoleic acid to a novel compound, 12,13,17-trihydroxy-9 (Z)-octadecenoic acid (THOA). The organism is a Gram-positive, non-motile rod (0.5 microns x 2 microns). It was identified as a species of Clavibacter ALA2. The product was purified by high pressure liquid chromatography, and its structure was determined by 1H and 13C nuclear magnetic resonance and Fourier transform infrared spectroscopies, and by mass spectrometer. Maximum production of THOA with 25% conversion of the substrate was reached after 5-6 days of reaction. THOA was not further metabolized by strain ALA2. This is the first report of a 12,13,17-trihydroxy unsaturated fatty acid and its production by microbial transformation. Some dihydroxy intermediates were also detected. THOA has a structure similar to those of known plant self-defense substances.
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Oil Chemical Research, National Center for Agricultural Utilization Research, US Department of Agriculture, Peoria, Illinois 61604, USA.
Brown
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Labeda
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Abbott
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Weisleder
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D001419:Bacteria / Q000378:metabolism*; D005231:Fatty Acids, Unsaturated / Q000096:biosynthesis*; D006863:Hydrogen-Ion Concentration; D019787:Linoleic Acid; D008041:Linoleic Acids / Q000378:metabolism*; D012988:Soil Microbiology; D013696:Temperature
D005231:Fatty Acids, Unsaturated; D008041:Linoleic Acids; D019787:Linoleic Acid