The role of cytochrome P450 in the regulation of cholesterol biosynthesis

Lipids

Volumn 37, Issue 12, 2003, Pages 1163-1170

  Gibbons, Geoffrey F ^a,b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b RADCLIFFE INFIRMARY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BIOSYNTHESIS; CELLS; ESTERS; METABOLISM; PROTEINS;

BIOSYNTHETIC INTERMEDIATES;

CHOLESTEROL;

CHOLESTEROL; CYTOCHROME P450; ESTER DERIVATIVE; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE; LANOSTEROL DERIVATIVE; OXYSTEROL; STEROL REGULATORY ELEMENT BINDING PROTEIN; TRANSCRIPTION FACTOR;

ANIMAL CELL; CHOLESTEROL METABOLISM; CHOLESTEROL SYNTHESIS; CONFERENCE PAPER; DEMETHYLATION; ENZYME INACTIVATION; ENZYME INHIBITION; ENZYME REPRESSION; GENETIC TRANSCRIPTION; MAMMAL CELL; NONHUMAN; PROTEIN EXPRESSION; RAT;

ANIMALS; CELL LINE; CHOLESTEROL; CRICETINAE; CYTOCHROME P-450 ENZYME SYSTEM; HYDROXYMETHYLGLUTARYL COA REDUCTASES; HYDROXYMETHYLGLUTARYL-COA REDUCTASE INHIBITORS; OXIDATION-REDUCTION; RATS;

ANIMALIA; MAMMALIA;

EID: 0037413191     PISSN: 00244201     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11745-002-1016-x     Document Type: Conference Paper

References (48)

1. Gibbons, G.F., Goad, L.J. and Goodwin, T.W. (1968) The Stereochemistry of Hydrogen Elimination from C-15 During Cholesterol Biosynthesis, J. Chem. Soc. Chem. Commun., 1458-1460.
2. Akhtar, M., Freeman, C.W., Wilton, D.C., Boar, R.B., and Copsey, D.B. (1977) Oxidative Metabolism of Lanosterol in the Biosynthesis of Cholesterol, Bioorg. Chem. 6, 473-481.
3. Gibbons, G.F., Mitropoulos, K.A., and Myant, N.B. (1982), Biochemistry of Cholesterol, pp. 131-188, Elsevier Biomedical Press, Amsterdam.
4. Gibbons, G.F., and Mitropoulos, K.A. (1973) The Role of Cytochrome P-450 in Cholesterol Biosynthesis, Eur. J. Biochem. 40, 267-273.
5. Alexander, K.T.W., Mitropoulos, K.A., and Gibbons, G.F. (1974) A Possible Role for Cytochrome P450 During the Biosynthesis of Zymosterol from Lanosterol by Saccharomyces cerevisiae, Biochem. Biophys. Res. Commun. 60, 460-467.
6. Stromstedt, M., Rozman, D., and Waterman, M.R. (1996) The Ubiquitously Expressed Human CYP51 Encodes Lanosterol 14 α-Demethylase, a Cytochrome P450 Whose Expression Is Regulated by Oxysterols, Arch. Biochem. Biophys. 329, 73-81.
7. Debeljak, N., Horvat, S., Vouk, K., Lee, M., and Rozman, D. (2000) Characterization of the Mouse Lanosterol 14α-Demethylase (CYP51), a New Member of the Evolutionarily Most Conserved Cytochrome P450 Family, Arch. Biochem. Biophys. 379, 37-45.
8. Nelson, D.R., Kamataki, T., Waxman, D.J., Guengerich, F.P., Estabrook, R.W., Feyereisen, R., Gonzalez, F.J., Coon, M.J., Gunsalus, I.C., Gotoh, O., et. al. (1993) The P450 Superfamily: Update on New Sequences, Gene Mapping, Accession Numbers, Early Trivial Names of Enzymes, and Nomenclature, DNA Cell Biol. 12, 1-51.
9. Gibbons, G.F., Mitropoulos, K.A., and Pullinger, C.R. (1976) Lanosterol 14α-Demethylase. The Metabolism of Some Potential Intermediates by Cell-free Systems from Rat Liver, Biochem. Biophys. Res. Commun. 69, 781-789.
10. Akhtar, M., Alexander, K., Boar, R.B., McGhie, J.F., and Barton, D.H. (1978) Chemical and Enzymic Studies on the Characterization of Intermediates During the Removal of the 14α-Methyl Group in Cholesterol Biosynthesis. The Use of 32-Functionalized Lanostane Derivatives, Biochem. J. 169, 449-463.
11. Trzaskos, J.M. (1995) Oxylanosterols as Modifiers of Cholesterol Biosynthesis, Prog. Lipid Res. 34, 99-116.
12. Kandutsch, A.A., and Chen, H.W. (1973) Inhibition of Sterol Synthesis in Cultured Mouse Cells by 7α-Hydroxycholesterol, 7β-Hydroxycholesterol and 7-Ketocholesterol, J. Biol. Chem. 248, 8408-8417.
13. Kandutsch, A.A., Chen, H.W., and Heiniger, H.J. (1978) Biological Activity of Some Oxygenated Sterols, Science 201, 498-501.
14. Schroepfer, G.J., Jr. (2000) Oxysterols: Modulators of Cholesterol Metabolism and Other Processes, Physiol. Rev. 80, 361-554.
15. Horton, J.D., Goldstein, J.L., and Brown, M.S. (2002) SREBPs: Activators of the Complete Program of Cholesterol and Fatty Acid Synthesis in the Liver, J. Clin. Invest. 109, 1125-1131.
16. Brown, M.S., and Goldstein, J.L. (1999) A Proteolytic Pathway That Controls the Cholesterol Content of Membranes, Cells, and Blood, Proc. Natl. Acad. Sci. USA 96, 11041-11048.
17. Janowski, B.A., Willy, P.J., Devi, T.R., Falck, J.R., and Mangelsdorf, D.J. (1996) An Oxysterol Signalling Pathway Mediated by the Nuclear Receptor LXRα, Nature 383, 728-731.
18. Peet, D.J., Turley, S.D., Ma, W., Janowski, B.A., Lobaccaro, J.M., Hammer, R.E., and Mangelsdorf, D.J. (1998) Cholesterol and Bile Acid Metabolism Are Impaired in Mice Lacking the Nuclear Oxysterol Receptor LXRα, Cell 93, 693-704.
19. Lehmann, J.M., Kliewer, S.A., Moore, L.B., Smith-Oliver, T.A., Oliver, B.B., Su, J.L., Sundseth, S.S., Winegar, D.A., Blanchard, D.E., Spencer, T.A., and Willson, T.M. (1997) Activation of the Nuclear Receptor LXR by Oxysterols Defines a New Hormone Response Pathway, J. Biol. Chem. 272, 3137-3140.
20. Forman, B.M., Ruan, B., Chen, J., Schroepfer, G.J., Jr., and Evans, R.M. (1997) The Orphan Nuclear Receptor LXRα is Positively and Negatively Regulated by Distinct Products of Mevalonate Metabolism, Proc. Natl. Acad. Sci. USA 94, 10588-10593.
21. Schultz, J.R., Tu, H., Luk, A., Repa, J.J., Medina, J.C., Li, L., Schwendner, S., Wang, S., Thoolen, M., Mangelsdorf, D.J., et al. (2000) Role of LXRs in Control of Lipogenesis, Genes Dev. 14, 2831-2838.
22. Repa, J.J., Turley, S.D., Lobaccaro, J.A., Medina, J., Li, L., Lustig, K., Shan, B., Heyman, R.A., Dietschy, J.M., and Mangelsdorf, D.J. (2000) Regulation of Absorption and ABC1- Mediated Efflux of Cholesterol by RXR Heterodimers, Science 289, 1524-1529.
23. Gibbons, G.F., Pullinger, C.R., Chen, H.W., Cavenee, W.K., and Kandutsch, A.A. (1980) Regulation of Cholesterol Synthesis in Cultured Cells by Probable Natural Precursor Sterols. J. Biol. Chem. 255, 375-400.
24. Cavenee, W.K., Gibbons, G.F., Chen, H.W., and Kandutsch, A.A. (1979) Effects of Various Oxygenated Sterols on Cellular Sterol Biosynthesis in Chinese Hamster Lung Cells Resistant to 25-Hydroxycholesterol, Biochim. Biophys. Acta 575, 255-265.
25. Gibbons, G.F., Pullinger, C.R., Baillie, T.A., and Clare, R.A. (1980) Metabolism of Hydroxysterols by Rat Liver, Biochim. Biophys. Acta 619, 98-106.
26. Gibbons, G.F. (1983) The Role of Oxysterols in the Regulation of HMG-CoA Reductase, Biochem. Soc. Trans. 11, 649-651.
27. Marco de la Calle, C., Hwang, W., Pullinger, C.R., and Gibbons, G.F. (1988) A Relationship Between the Activities of Hepatic Lanosterol 14α-Demethylase and 3-Hydroxy-3-methylglutaryl CoA Reductase, Biochem. J. 250, 33-39.
28. Iglesias, J., and Gibbons, G.F. (1989) Regulation of Hepatic Cholesterol Biosynthesis. Effects of a Cytochrome P-450 Inhibitor on the Formation and Metabolism of Oxygenated Products of Lanosterol, Biochem. J. 264, 495-502.
29. Gibbons, G.F., and Ramananda, K. (1975) Synthesis and Configuration at C-15 of the Epimeric 5α-Lanost-8-en-3β,15-diols, J. Chem. Soc. Chem. Commun., 213.
30. Gibbons, G.F., Mitropoulos, K.A., and Pullinger, C.R. (1976) Lanosterol 14α-Demethylase. The Metabolism of Some Potential Intermediates by Cell-free Systems from Rat Liver, Biochem. Biophys. Res. Commun. 69, 781.
31. Brown, M.S., Goldstein, J.L., and Dietschy, J.M. (1979) Active and Inactive Forms of 3-Hydroxy-3-methylglutaryl Coenzyme A Reductase in the Liver of the Rat. Comparison with the Rate of Cholesterol Synthesis in Different Physiological States, J. Biol. Chem. 254, 5144-5149.
32. Iglesias, J. and Gibbons, G.F. (1989) Oxidative Metabolism of Cholesterol Precursors. Sensitivity to Ketoconazole, an Inhibitor of Cytochrome P-450, Steroids 53, 311-328.
33. 3H] Water, J. Lipid Res. 24, 1321-1328.
34. Bellamine, A., Mangla, A.T., Nes, W.D., and Waterman, M.R. (1999) Characterization and Catalytic Properties of the Sterol 14α-Demethylase from Mycobacterium tuberculosis, Proc. Natl. Acad. Sci. USA 96, 8937-8942.
35. Podust, L.M., Poulos, T.L. and Waterman, M.R. (2001) Crystal Structure of Cytochrome P450 14α-Sterol Demethylase (CYP51) from Mycobacterium tuberculosis in Complex with Azole Inhibitors, Proc. Natl. Acad. Sci. USA 98, 3068-3073.
36. Byskov, A.G., Andersen, C.Y., Nordholm, L., Thogersen, H., Xia, G., Wassmann, O., Andersen, J.V., Guddal, E., and Roed, T. (1995) Chemical Structure of Sterols That Activate Oocyte Meiosis, Nature 374, 559-562.
37. Rozman, D., and Waterman, M.R. (1998) Lanosterol 14α- Demethylase (CYP51) and Spermatogenesis, Drug Metab. Dispos. 26, 1199-1201.
38. Shimano, H. (2001) Sterol Regulatory Element-Binding Proteins (SREBPs): Transcriptional Regulators of Lipid Synthetic Genes, Prog. Lipid Res. 40:439-452.
39. Brown, A.J., Sun, L., Feramisco, J.D., Brown, M.S., and Goldstein, J.L. (2002) Cholesterol Addition to ER Membranes Alters Conformation of SCAP, the SREBP Escort Protein That Regulates Cholesterol Metabolism, Mol. Cell. 10, 237-245.
40. Saucier, S.E., Kandutsch, A.A., Phirwa, S., and Spencer, T.A. (1987) Accumulation of Regulatory Oxysterols, 32-Oxolanosterol and 32-Hydroxylanosterol in Mevalonate-Treated Cell Cultures. J. Biol. Chem. 262, 14056-14062.
41. Tabacik, C., Aliau, S., Astruc, M., and Crastes de Paulet, A. (1981) Post-HMG-CoA Reductase Regulation of Cholesterol Biosynthesis in Normal Human Lymphocytes and Lanosten-3β- ol-32-al, a Natural Inhibitor, Biochem. Biophys. Res. Commun. 101, 1087-1095.
42. Gibbons, G.F., Pullinger, C.R., and Mitropoulos, K.A. (1979) Studies on the Mechanism of Lanosterol 14α-Demethylase. A Requirement for Two Distinct Types of Mixed Function Oxidase, Biochem. J. 183, 309-315.
43. Janowski, B.A., Grogan, M.J., Jones, S.A., Wisely, G.B., Kliewer, S.A., Corey, E.J., and Mangelsdorf, D.J. (1999) Structural Requirements of Ligands for the Oxysterol Liver X Receptors LXRα and LXRβ, Proc. Natl. Acad. Sci. U.S.A. 96, 266-271.
44. Kandutsch, A.A., and Chen, H.W. (1974) Inhibition of Sterol Synthesis in Cultured Mouse Cells by Cholesterol Derivatives Oxygenated in the Side Chain, J. Biol. Chem. 249, 6057-6061.
45. Kandutsch, A.A., and Chen, H.W. (1978) Inhibition of Cholesterol Synthesis by Oxygenated Sterols, Lipids 13, 704-707.
46. Martin, K.O., Reiss, A.B., Lathe, R., and Javitt, N.B. (1997) 7α-Hydroxylation of 27-Hydroxycholesterol: Biologic Role in the Regulation of Cholesterol Synthesis, J. Lipid Res. 38, 1053-1058.
47. Kuipers, F., Havinga, R., Huijsmans, C.M., Vonk, R.J., and Princen, H.M. (1989) Inhibition and Induction of Bile Acid Synthesis by Ketoconazole. Effects on Bile Formation in the Rat, Lipids 24, 759-764.
48. Kempen, H.J., van Son, K., Cohen, L.H., Griffioen, M., Verboom, H., and Havekes, L. (1987) Effect of Ketoconazole on Cholesterol Synthesis and on HMG-CoA Reductase and LDL-Receptor Activities in Hep G2 cells, Biochem. Pharmacol. 36, 1245-1249.