Abstract
Four 15-oxygenated sterols with the "unnatural" cis-C-D ring juncture have recently been shown to be potent inhibitors of sterol synthesis in animal cells in culture (Schroepfer, G.J., Jr., Parish, E.J., Chen, H.W., and Kandutsch, A.A. (1977) J. Biol. Chem. 252, 8975-8980; Schroepfer, G.J., Jr., Pascal, R.A., Jr., and Kandutsch, A.A. (1979) Biochem. Pharmacol. 28, 249-252). In the present study we have prepared two of these sterols, [2,4-3H]5 alpha,14 beta-cholest-7-ene-3 beta,15 alpha-diol and [2,4-3H]5 alpha,14 beta-cholest-7-ene-3 beta,15 beta-diol, in labeled form, 5 alpha,14 beta-Cholest-7-ene-3 beta, 15 alpha-diol, but not its 15 beta-hydroxy epimer, was shown to be efficiently converted to cholesterol in 10,000 x g supernatant fractions of liver homogenate preparations from both male and female rats. After incubation of [2,4-3H]5 alpha,14 beta-cholest-7-ene-3 beta,15 alpha-diol with these enzyme preparations a number of labeled products, in addition to cholesterol, were isolated and characterized. These included 5 alpha-cholesta-8,14-dien-3 beta-ol, cholesta-5,7-dien-3 beta-ol, 5 alpha-cholest-8-en-3 beta-ol, and 5 alpha-cholest-7-en-3 beta-ol. A scheme to account for the enzymatic formation of cholesterol and the other sterol precursors of cholesterol is presented.
Highlights
Hydroxy epimer,was shown to be efficiently converted to cholesterol in 10,000 X g supernatant fractions of liverhomogenate preparationsfrombothmaleand female rats
Affiliate of T h e American Heart AssociationT. h e costs of publication of this article were defrayed in part by the paymenotf page charges
" T h e materialdescribing theexperimentalproceduresandthe results of the detailed analysis of the products of the incubations of the substrates is presented as a miniprint section along with Figs. 1 through 10 and TablesI through 111
Summary
STUDIES OF THE METABOLISM OF ~ c x , ~ ~ P - CHOLEST - ~ - E N E -A~NPD,~~C~I~,-~D~IPO-LCHOLEST-~-ENE-~P, DIOL* Hydroxy epimer,was shown to be efficiently converted to cholesterol in 10,000 X g supernatant fractions of liverhomogenate preparationsfrombothmaleand female rats. After incubationof [2,4-3H]5a,14/3-cholest7-ene-3&15a-diol withthese enzyme preparations a number of labeled products, in addition to cholesterol, wereisolated and characterized.These included 5acholesta-8,14-dien-3fl-o1, cholesta-5,7-dien-3/3-01, 5acholest-8-en-3/3-01,and 5a-cholest-7-en-3/3-01.A scheme to account for the enzymatic formation of cholesterol and the other sterol precursors of cholesterol is presented.
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