A simple method for the preparation of pure 9-D-hydroperoxide of linoleic acid and methyl linoleate based on the positional specificity of lipoxygenase in tomato fruit.
Incubation of linoleic acid with crude homogenate of tomato fruit gave a high yield (69%) of linoleic acid hydroperoxides with a ratio of 9- to 13-hydroperoxide isomers of 96:4. After chromatography of the products, as free acids or methyl esters, hydroperoxides with 9- to 13-isomeric ratios of greater than 99:1 were obtained. The major product was characterized as 9-D-hydroperoxy-octadeca-trans-10,cis-12-dienoic acid. The results demonstrate the positional specificity of lipoxygenase from tomato fruit.
D008041:Linoleic Acids / Q000138:chemical synthesis*; D008054:Lipid Peroxides; D008084:Lipoxygenase / Q000378:metabolism*; D010545:Peroxides / Q000138:chemical synthesis*; D010944:Plants / Q000201:enzymology; D013329:Structure-Activity Relationship
D008041:Linoleic Acids; D008054:Lipid Peroxides; D010545:Peroxides; C008285:linoleic acid hydroperoxide; D008084:Lipoxygenase