Development of Methods for Synthesis of Stereo-Selective Lipid Peroxides

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The Autoxidation of linolenic acid gave its 9- and 13-hydroperoxy derivatives. The autoxidation of fatty acids which have more than 3 double bonds gave cyclic peroxides as a by-product. But the addition of hydrogen donor in this system increased the selectivity for the formation of hydroperoxides. Four different hydroperoxides were formed from linolenic acid and six hydroperoxides from arachidonic acid. These hydroperoxides mentioned above were separated and purified by High Performance Liquid Chromatography. The autoxidation of phospholipids, triglycerides, and cholesteryl esters also gave their hydroperoxides, but the separation of their isomers were not easy.About 3 nM of cholesteryl ester hydroperoidde was detected in human blood plasma. According to the retention times of the compounds, they were ascribed to be hydroperoxides of cholesteryl linolate and cholesteryl arachidonate. On the other hand, phospholipid hydroperoidde was not detected.A methods for the detection of picomole level of fatty acid oxidation products was developed using monodansyl cadaverin as a fluorescent derivatizing reagent 1% method will be useful for the quantitation and qualification of lipid peroxides derived from biological samples.It is very important know whether lipid peroxides are formed by non-enzymatic pathway or not. The methods developed in this project will be useful to answer this question.