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

Add time:09/07/2019    Source:sciencedirect.com

(25R)-5α-Cholest-8(14)-ene-3β,15β,26-triol (III) was prepared by reduction of (25R)-3β,26-diacetoxy-5α-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 3β-hydroxy-5α-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 5α-cholest-8(14)-ene-3β,15β-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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