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Journal of Lipid Research, Vol. 15, 389-398, July 1974
Copyright © 1974 by Lipid Research, Inc.

Formation and metabolism in vitro of 5,6-epoxides of cholesterol and ßbeta;-sitosterol

Leif Aringer and Peter Eneroth

Department of Chemistry, Karolinska Institutet, and the Hormone Laboratory, Department of Obstetrics and Gynecology, Karolinska Sjukhuset, S-104 01 Stockholm 60, Sweden

The formation of 5,6- and 5ßbeta;,6ßbeta;-epoxides of cholesterol and ßbeta;-sitosterol in rat liver subcellular fractions has been studied. The results show that the epoxidation seems to occur only in connection with the nonspecific tissue oxidation of the sterols. The ßbeta;-epoxides were formed in three- to fourfold excess over the -epoxides. Both cholesterol epoxides were efficiently converted by a microsomal hydrolase into the 3ßbeta;,5,6ßbeta;-triol. The conversion was less extensive with ßbeta;-sitosterol epoxides, especially the ßbeta;-epoxide. The possible biological significance in the formation of the sterol epoxides and the triols was evaluated by their ability to inhibit the microsomal cholesterol 7-hydroxylase. Only the cholesterol epoxides and especially the ßbeta;-epoxide were active in this respect.

Supplementary key words lipid peroxidation • epoxide hydrolase • cholestane-3ßbeta;,5,6ßbeta;-triol • cholesterol-7-hydroxylase • inhibition by 5,6-epoxysterols and 3ßbeta;,5,6ßbeta;-trihydroxysterols • hydroxyalkylated Sephadex LH-20 • thin-layer chromatography • gas-liquid chromatography-mass spectrometry

Submitted on January 14, 1974
Accepted on April 2, 1974

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