Biotransformation of linoleic acid by Clavibacter sp. ALA2: heterocyclic and heterobicyclic fatty acids.
Clavibacter sp. ALA2 transformed linoleic acid into a variety of oxylipins. In previous work, three novel fatty acids were identified, (9Z)-12, 13, 17-trihydroxy-9-octadecenoic acid and two tetrahydrofuran-(di)hydroxy fatty acids. In this report, we confirm the structures of the tetrahydrofuran-(di)hydroxy fatty acids by nuclear magnetic resonance as (9Z)-12-hydroxy-13,16-epoxy-9-octadecenoic acid and (9Z)-7,12-dihydroxy-13,16-epoxy-9-octadecenoic acid. Three other products of the biotransformation were identified as novel heterobicyclic fatty acids, (9Z)-12,17;13, 17-diepoxy-9-octadecenoic acid, (9Z)-7-hydroxy-12,17;13,17-diepoxy-9-octadecenoic acid, and (9Z)-12,17;13,17-diepoxy-16-hydroxy-9-octadecenoic acid. Thus, Clavibacter ALA2 effectively oxidized linoleic acid at C-7, -12, -13, -16, and/or -17.
Gardner
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Bioactive Agents Research, National Center for Agricultural Utilization Research, ARS, USDA, Peoria, Illinois 61604, USA.
Hou
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Weisleder
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Brown
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D001711:Biotransformation; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D004852:Epoxy Compounds / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism*; D005227:Fatty Acids / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry; D007536:Isomerism; D019787:Linoleic Acid / Q000493:pharmacokinetics*; D009682:Magnetic Resonance Spectroscopy; D008837:Micrococcus / Q000378:metabolism*; D008956:Models, Chemical; D009829:Oleic Acids / Q000737:chemistry / Q000378:metabolism; D010100:Oxygen / Q000378:metabolism; D013997:Time Factors
C119104:12,13-epoxy-9-octadecenoic acid; D004852:Epoxy Compounds; D005227:Fatty Acids; D009829:Oleic Acids; D019787:Linoleic Acid; D010100:Oxygen