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  • Title: A mechanism for epoxidation of cholesterol by hepatic microsomal lipid hydroperoxides.
    Author: Watabe T, Tsubaki A, Isobe M, Ozawa N, Hiratsuka A.
    Journal: Biochim Biophys Acta; 1984 Aug 15; 795(1):60-6. PubMed ID: 6466699.
    Abstract:
    Evidence was obtained, using cis-stilbene as a model substrate, for the participation of peroxy and/or oxy radicals in epoxidation of cholesterol by rat liver microsomal phospholipid hydroperoxides and a ferrous ion-ADP complex. Under the conditions used, cholesterol was epoxidised to the alpha- and beta-epoxides in the ratio 1:2-4, and cis-stilbene to trans-stilbene oxide without concomitant formation of the cis-oxide. Microsomal phospholipid hydroperoxides could be replaced with methyllinoleate monohydroperoxide for the epoxidation of both substrates. The hydroperoxide-mediated epoxidations were completely inhibited by alpha-tocopherol and t-butylhydroxyanisole. A GLC study suggested that highly polyunsaturated fatty acyl constituents of the microsomal phospholipids might play an important role in epoxidation of the olefinic substrates.
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