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  • Title: Inhibitors of sterol synthesis. Chemical synthesis and spectral properties of (25R)-5 alpha-cholest-8(14)-ene-3 beta,15 beta,26-triol, a potential metabolite of 3 beta-hydroxy-5 alpha-cholest-8(14)-en-15-one and its effects on 3-hydroxy-3-methylglutaryl-coenzyme A reductase in CHO-K1 cells.
    Author: Swaminathan S, Pinkerton FD, Wilson WK, Schroepfer GJ.
    Journal: Chem Phys Lipids; 1992 May; 61(3):235-42. PubMed ID: 1525963.
    Abstract:
    (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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