Abstract
Peroxy free radicals (R-0-0•) have been proposed as discrete intermediates in the conversion of fatty acids to prostaglandins as well as in the nonenzymatic autoxidation of lipids. The chemistry of unsaturated peroxy radicals has not, however, been explored in any detail in the past. We report here on simple chemical model studies of unsaturated peroxy free radicals. Peroxy radicals generated by hydrogen atom abstraction from hydroperoxides undergo cycli zation reactions to give monocyclic and bicyclic endoperoxides. These studies support the free radical mechanism of PG biosynthesis and suggest that monocyclic and bicyclic peroxides are formed in lipid peroxidation. These cyclic peroxides have important physiological activity, the bicyclic compounds being analogous to PGG and PGH. The monocyclic compounds have been shown to inhibit arachidonic acid induced aggregation of human platelets. Thus, not only bicyclic endoperoxides but also monocyclic peroxides may have physiological and pharmacological importance.
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