Enzymatic formation of 9,16-dihydro(pero)xyoctadecatrienoic acid isomers from alpha-linolenic acid.
Incubation of alpha-linolenic acid with soybean lipoxygenase at pH 6.5 led to formation of conjugated triene oxidation products exhibiting maximum uv absorption at 267 nm, which were converted into four 9,16-dihydroxyoctadecatrienoic acid isomers. In the precursor-substrate study, it seems that 9,16-dihydroxy acid isomers are derived from the doubly oxygenated products and the epoxide intermediate, which are both produced from hydrogen removal at C-14 of 9(S)-hydroperoxyoctadecatrienoic acid. Optimum pH and Km values for soybean lipoxygenase-1-catalyzed conversion of 9(S)-hydroperoxyoctadecatrienoic acid into the conjugated triene products were 8.5 and 80 microM, respectively.
Sok
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DE
Division of Biomedicine, Daejeon Machine Depot, Korea.
Kim
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MR
D002851:Chromatography, High Pressure Liquid; D006863:Hydrogen-Ion Concentration; D007536:Isomerism; D007700:Kinetics; D008042:Linolenic Acids / Q000096:biosynthesis / Q000378:metabolism*; D008084:Lipoxygenase / Q000378:metabolism*; D013058:Mass Spectrometry; D010545:Peroxides; D013025:Glycine max / Q000201:enzymology; D013056:Spectrophotometry, Ultraviolet
D008042:Linolenic Acids; D010545:Peroxides; D008084:Lipoxygenase