Identification of CYP3A4 as the major enzyme responsible for 25-hydroxylation of 5beta-cholestane-3alpha,7alpha,12alpha-triol in human liver microsomes

Biochim Biophys Acta. 1999 Jan 29;1437(1):46-52. doi: 10.1016/s0005-2760(98)00175-1.

Abstract

Human liver microsomes catalyze an efficient 25-hydroxylation of 5beta-cholestane-3alpha,7alpha,12alpha-triol. The hydroxylation is involved in a minor, alternative pathway for side-chain degradation in the biosynthesis of cholic acid. The enzyme responsible for the microsomal 25-hydroxylation has been unidentified. In the present study, recombinant expressed human P-450 enzymes have been used to screen for 25-hydroxylase activity towards 5beta-cholestane-3alpha, 7alpha,12alpha-triol. High activity was found with CYP3A4, but also with CYP3A5 and to a minor extent with CYP2C19 and CYP2B6. Small amounts of 23- and 24-hydroxylated products were also formed by CYP3A4. The Vmax for 25-hydroxylation by CYP3A4 and CYP3A5 was 16 and 4.5 nmol/(nmolxmin), respectively. The Km was 6 microM for CYP3A4 and 32 microM for CYP3A5. Cytochrome b5 increased the hydroxylase activities. Human liver microsomes from ten different donors, in which different P-450 marker activities had been determined, were incubated with 5beta-cholestane-3alpha,7alpha, 12alpha-triol. A strong correlation was observed between formation of 25-hydroxylated 5beta-cholestane-3alpha,7alpha,12alpha-triol and CYP3A levels (r2=0.96). No correlation was observed with the levels of CYP2C19. Troleandomycin, a specific inhibitor of CYP3A4 and 3A5, inhibited the 25-hydroxylase activity of pooled human liver microsomes by more than 90% at 50 microM. Tranylcypromine, an inhibitor of CYP2C19, had very little effect on the conversion. From these results, it can be concluded that CYP3A4 is the predominant enzyme responsible for 25-hydroxylation of 5beta-cholestane-3alpha, 7alpha,12alpha-triol in human liver microsomes.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aryl Hydrocarbon Hydroxylases*
  • Bile Acids and Salts / biosynthesis*
  • Cholestanetriol 26-Monooxygenase
  • Cholestanols / metabolism*
  • Cholesterol / metabolism
  • Cytochrome P-450 CYP2C19
  • Cytochrome P-450 CYP3A
  • Cytochrome P-450 Enzyme Inhibitors
  • Cytochrome P-450 Enzyme System / metabolism*
  • Enzyme Inhibitors / pharmacology
  • Gas Chromatography-Mass Spectrometry
  • Humans
  • Kinetics
  • Microsomes, Liver / enzymology*
  • Mixed Function Oxygenases / antagonists & inhibitors
  • Mixed Function Oxygenases / metabolism*
  • Steroid Hydroxylases / antagonists & inhibitors
  • Steroid Hydroxylases / metabolism*
  • Troleandomycin / pharmacology

Substances

  • Bile Acids and Salts
  • Cholestanols
  • Cytochrome P-450 Enzyme Inhibitors
  • Enzyme Inhibitors
  • 3,7,12-trihydroxycoprostane
  • Cytochrome P-450 Enzyme System
  • Cholesterol
  • Troleandomycin
  • Mixed Function Oxygenases
  • Steroid Hydroxylases
  • Aryl Hydrocarbon Hydroxylases
  • CYP2C19 protein, human
  • CYP3A protein, human
  • CYP3A5 protein, human
  • Cytochrome P-450 CYP2C19
  • Cytochrome P-450 CYP3A
  • CYP3A4 protein, human
  • CYP27A1 protein, human
  • Cholestanetriol 26-Monooxygenase