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Inhibitors of sterol synthesis. Chemical synthesis and spectral properties of (25R)-5α-cholest-8(14)-ene-3β,15β,26-triol, a potential metabolite of 3β-hydroxy-5α-cholest-8(14)-en-15-one and its effects on 3-hydroxy-3-methylglutaryl-coenzyme A reductase in CHO-K1 cells

✍ Scribed by Shankar Swaminathan; Frederick D. Pinkerton; William K. Wilson; George J. Schroepfer Jr.

Publisher
Elsevier Science
Year
1992
Tongue
English
Weight
570 KB
Volume
61
Category
Article
ISSN
0009-3084

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✦ Synopsis

(25R)-5 alpha-Cholest-8(14)-ene-3 beta,15 beta,26-triol (III) was prepared by reduction of (25R)-3 beta,26-diacetoxy-5 alpha-cholest-8(14)-en-15-one with sodium borohydride followed by treatment of the crude product with lithium aluminium hydride. The trihydroxysterol III, a potential metabolite of 3 beta-hydroxy-5 alpha-cholest-8(14)-en-15-one, was characterized by the results of mass spectral studies and by nuclear magnetic resonance (NMR) spectroscopy. Full 1H and 13C NMR assignments for III and 5 alpha-cholest-8(14)-ene-3 beta,15 beta-diol are given and used to establish the structure of III. The triol was found to be very potent in lowering the levels of 3-hydroxy-3-methylglutaryl coenzyme A reductase activity in Chinese hamster ovary cells.

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