J. Lipid Res. Neurobiology of Lipids (ISSN1683-5506)
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Journal of Lipid Research, Vol 16, 426-433, Copyright © 1975 by Lipid Research, Inc.

ARTICLES

Conversion of 7alpha-hydroxycholesterol and 7alpha-hydroxy-beta- sitosterol to 3alpha, 7alpha-dihydroxy- and 3alpha, 7alpha, 12alpha- trihydroxy-5beta-steroids in vitro

L Aringer

The metabolism of 7alpha-hydroxycholesterol and 7alpha-hydroxy-beta- sitosterol (24alpha-ethyl-5-cholestene-3beta,7alpha-diol) has been compared in rat liver subcellular fractions. 7alpha-Hydroxy-beta- sitosterol was shown to be metabolized in the same manner as 7alpha- hydroxycholesterol. Thus, the following C29 metabolites have been identified: 24alpha-ethyl-7alpha-hydroxy-4-cholesten-3-one, 24alpha- ethyl-7alpha,12alpha-dihydroxy-4-cholesten-3-one, 24alpha-ethyl-7alpha- hydroxy-5beta-cholestan-3-one, 24alpha-ethyl-5beta-cholestane- 3alpha,7alpha-diol, 24alpha-ethyl-7alpha,12alpha-dihydrozy-5beta- cholestan-3-one, and 24alpha-ethyl-5beta-cholestane- 3alha,7alpha,12alpha-triol. The C29 compounds were generally less efficient substrates. The most pronounced difference was noted for the delta4-3-oxosteroid 5beta-reductase. Thus, 7alpha-hydroxy-4-cholesten-3- one was three to four times as efficiently reduced as the C29 analog. The oxidation of the 3beta,7alpha-dihydroxy-delta5-steroid to the 7alpha-hydroxy-delta4-3-oxosteroid, the 12alpha-hydroxylation of the 7alpha-hydroxy-delta4-3-oxosteroid, and the reduction of the 7alpha- hydroxy-5beta-3-oxosteroid to the 3alpha,7alpha-dihydroxy-5beta-steroid occurred in up to two times better yields for the C27 steroids.
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Copyright © 1975 by the American Society for Biochemistry and Molecular Biology.