Lipid oxidation: Mechanisms, products and biological significance

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Abstract
This paper reviews our studies of fatty acid hydroperoxides, their secondary products and mechanisms for their formation in the context of some of their possible biological consequences. The uneven distribution of isomeric hydroperoxides in oxidized linolenate and photosensitized oxidized linoleate is related to the formation of hydroperoxy cyclic peroxides. Interest in the hydroperoxy mono‐and bi‐cycloendoperoxides from oxidized linolenate stems from their structural relationship to the prostaglandins. However, the biological activity of hydroperoxy cyclic peroxides formed by autoxidation has not yet been reported. Thermal decomposition studies of secondary lipid oxidation products show they are important precursors of volatile compounds. An acid‐acetalation decomposition procedure establishes that 5‐membered hydroperoxy cyclic peroxides and 1,3‐dihydroperoxides are important precursors of malonaldehyde. This approach provides a more specific test than the thiobarbituric acid (TBA) color reaction to evaluate lipid oxidation products as sources of malonaldehyde and its biological effects due to crosslinking. A better understanding is needed of the biological effects of a multitude of lipid oxidation decomposition products other than malonaldehyde.

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