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Journal of Lipid Research, Vol. 14, 618-624, November 1973
Copyright © 1973 by Lipid Research, Inc.

Metabolism of cholesteryl palmitate by rat brain in vitro; formation of cholesterol epoxides and cholestane-3ßbeta;,5,6ßbeta;-triol

Charles M. Martin and Harold J. Nicholas

Institute of Medical Education and Research and Department of Biochemistry, St. Louis University School of Medicine, St. Louis, Missouri 63104

Incubation of [4-¹⁴C]cholesteryl palmitate with the 12,000 g supernatant fraction of adult rat brain fortified with an NADPH-generating system and ßbeta;-mercaptoethylamine resulted in formation (2-5%) of more polar metabolites characterized as a mixture of cholesterol-5,6-epoxides. Under extended incubation conditions, cholestane-3ßbeta;-5-6ßbeta;-triol was isolated as the major end product of the incubations. Free [4-¹⁴C]cholesterol incubated under similar conditions was not oxidized, whereas oxidation of [4-¹⁴C]cholesteryl palmitate appeared to be dependent upon hydrolysis of the ester by the rat brain microsomal subcellular fraction. Elimination of the NADPH-generating system or the addition of EDTA to the incubation mixture inhibited epoxide formation, suggesting that the products are derived from an NADPH-dependent enzymatic lipoperoxidation mechanism. The in vitro conversion of [4-¹⁴C]cholesterol-5,6-epoxide to cholestane-3ßbeta;,5,6ßbeta;-triol was also demonstrated in rat brain subcellular fractions in the absence of added cofactors.

Supplementary key words brain cholesterol • cholesterol oxidation

Submitted on October 25, 1972
Revised on May 25, 1973
Accepted on June 28, 1973

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