Structural and evolutionary studies on sterol 14-demethylase P450 (CYP51), the most conserved P450 monooxygenase: II. Evolutionary analysis of protein and gene structures

Journal of Biochemistry

Volumn 122, Issue 6, 1997, Pages 1122-1128

  Yoshida, Yuzo ^a   Noshiro, Mitsuhide ^b   Aoyama, Yuri ^c   Kawamoto, Takeshi ^b   Horiuchi, Tadao ^c   Gotoh, Osamu ^d  

^a MUKOGAWA WOMEN'S UNIVERSITY   (Japan)

^b HIROSHIMA UNIVERSITY   (Japan)

^c SOKA UNIVERSITY   (Japan)

^d SAITAMA CANCER CENTER   (Japan)

Author keywords

Molecular evolution; P450; Phylogenetic tree; Processed pseudogene; Sterol 14 demethylase

Indexed keywords

CYTOCHROME P450; UNSPECIFIC MONOOXYGENASE;

AMINO ACID SEQUENCE; ARTICLE; DNA FLANKING REGION; ENZYME STRUCTURE; EVOLUTION; GENE INSERTION; GENE STRUCTURE; HUMAN; NONHUMAN; PHYLOGENY; PSEUDOGENE; RAT;

BACTERIA (MICROORGANISMS); FUNGI; MAMMALIA; PROKARYOTA;

EID: 0031446299     PISSN: 0021924X     EISSN: None     Source Type: Journal    
DOI: 10.1093/oxfordjournals.jbchem.a021870     Document Type: Article

References (38)

1. Nelson, D.R., Koymans, L., Kamataki, T., Stegeman, J.J., Feyereisen, R., Waxman, D.J., Waterman, M.R., Gotoh, O., Coon, M.J., Estabrook, R.W., Gunsalus, I.C., and Nebert, D.W. (1996) P450 Superfamily: Update on new sequences, gene mapping, accession numbers, and nomenclature. Pharmacogenetics 6, 1-42
2. Coon, M.J., Ding, X.X., Pernecky, S.J., and Vaz, A.D.N. (1992) Cytochrome P450: Progress and predictions. FASEB J. 6, 669-673
3. Yoshida, Y. and Aoyama, Y. (1994) The P450 superfamily: A group of versatile hemoproteins contributing to the oxidation of various small molecules in Regulation of Heme Protein Synthesis (Fujita, H., ed.) pp. 75-88, AlphaMed Press, Dayton
4. Coon, M.J., Vaz, A.D.N., and Bestervelt, L.L. (1996) Peroxidative reactions of diversozyme. FASEB J. 10, 428-434
5. Nelson, D.R., Kamataki, T., Waxman, D.J., Guengerich, P., Estabrook, R.W., Feyereisen, R., Gonzalez, F.J., Coon, M.J., Gunsalus, I.C., Gotoh, O., Okuda, K., and Nebert, D.W. (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
6. Gotoh, O. (1993) Evolution and differentiation of P-450 genes in Cytochrome P-450, 2nd ed. (Omura, T., Ishimura, Y., and Fujii-Kuriyama, Y., eds.) pp. 207-223, Kodansha, Tokyo and VCH, Weinheim
7. Yoshida, Y. (1993) Sterol biosynthesis in Cytochrome P-450, 2nd ed. (Omura, T., Ishimura, Y., and Fujii-Kuriyama, Y., eds.) pp. 93-101, Kodansha, Tokyo and VCH, Weinheim
8. 14DM) in the rat liver. Biochem. Biophys. Res. Commun. 201, 1320-1326
9. Aoyama, Y., Noshiro, M., Gotoh, O., Imaoka, S., Funae, Y., Kurosawa, N., Horiuchi, T., and Yoshida, Y. (1996) Sterol 14-demethylase P450 (P45014DM) is one of the most ancient and conserved P450 species. J. Biochem. 119, 926-933
10. Bak, S., Kahn, R.A., Olsen, C.-E., and Halkier, B.A. (1997) Cloning and expression in Escherichia coli of the obtusifoliol 14α-demethylase of Sorghum bicolor (L.) Monech, a cytochrome P450 orthologous to the sterol 14α-demethylase (CYP51) from fungi and mammals. Plant J. 11, 191-201
11. Cabello-Hurtado, F., Zimmerlin, A., Rahier, A., Taton, M., DeRose, R., Nedelkina, S., Batard, Y., Durst, F., Pallet, K.E., and Werck-Reichhart, D. (1997) Cloning and functional expression in yeast of a cDNA coding for an obtusifoliol 14α-demethylase (CYP51) in wheat. Biochem. Biophys. Res. Commun. 230, 381-385
12. Noshiro, M., Aoyama, Y., Kawamoto, T., Gotoh, O., Horiuchi, T., and Yoshida, Y. (1997) Structural and evolutionary studies on sterol 14-demethylase P450 (CYP51), the most conserved P450 monooxygenase: I. Structural analyses of the gene and multiple sizes of mRNA. J. Biochem. 122, 1114-1121
13. Rozman, D., Stromstedt, M., and Waterman, M.R. (1996) The three human cytochrome P450 lanosterol 14α-demethylase (CYP51) genes reside on chromosomes 3, 7, and 13: structure of the two retrotransposed pseudogenes, association with a line-1 element, and evolution of the human CYP51 family. Arch. Biochem. Biophys. 333, 466-474
14. Stromstedt, M., Rozman, D., and Waterman, M.R. (1996) The ubiquitously expressed human CYP51 encodes lanosterol 14α-demethylase, a cytochrome P450 whose expression is regulated by oxysterols. Arch. Biochem. Biophys. 329, 73-81
15. Rozman, D., Stromstedt, M., Tsui, L.-C., Scherer, S.W., and Waterman, M.R. (1996) Structure and mapping of the human lanosterol 14α-demethylase gene (CYP51) encoding the cytochrome P450 involved in cholesterol biosynthesis; comparison of exon/intron organization with other mammalian and fungal CYP genes. Genomics 38, 371-381
16. Gotoh, O. (1996) Significant improvement in accuracy of multiple protein sequence alignments by iterative refinement as assessed by reference to structural alignments. J. Mol. Biol. 264, 823-838
17. Saitou, N. and Nei, M. (1987) The neighbor-joining method: A new method for reconstructing phylogenetic trees. Mol. Biol. Evol. 4, 406-425
18. Kishino, H., Miyata, T., and Hasegawa, M. (1990) Maximum likelihood inference of protein phylogeny and the origin of chloroplasts. J. Mol. Evol. 31, 151-160
19. Felsenstein, J. (1992) PHYLIP (Phylogeny Inference Package) Version 3.5c, University of Washington, Seattle
20. Adachi, J. and Hasegawa, M. (1996) MOLPHY Version 2.3. Programs for molecular phylogenetics based on maximum likelihood in Computer Science Monographs Vol. 28, The Institute of Statistical Mathematics, Tokyo
21. Miyata, T. and Yasunaga, T. (1980) Molecular evolution of mRNA: A method for estimating evolutionary rates of synonymous and amino acid substitutions from homologous nucleotide sequences and its application. J. Mol. Evol. 16, 23-36
22. Nei, M. and Gojobori, T. (1986) Simple methods for estimating the numbers of synonymous and nonsynonymous nucleotide substitutions. Mol. Biol. Evol. 3, 418-426
23. Jukes, T.H. and Cantor, C.R. (1969) Evolution of protein molecules in Mammalian Protein Metabolism (Munro, H.N., ed.) Vol. 3, pp. 21-132, Academic Press, New York
24. Altschul, S.F., Gish, W., Miller, W., Myers, E.W., and Lipman, D.J. (1990) Basic local alignment search tool. J. Mol. Biol. 215, 403-410
25. Baldauf, S.L. and Palmer, J.D. (1993) Animals and fungi are each other's closest relatives: congruent evidence from multiple proteins. Proc. Natl. Acad. Sci. USA 90, 11558-11562
26. Doolittle, R.F., Feng, D.-F., Tsang, S., Cho, G., and Little, E. (1996) Determining divergence times of the major kingdoms of living organisms with a protein clock. Science 271, 470-477
27. 14DM) of Saccharomyces cerevisiae and rat liver for 24-methylene-24,25-dihydrolanosterol and 24,25-dihydrolanosterol. Biochem. Biophys. Res. Commun. 178, 1064-1071
28. 14DM) of yeast: Difference between the substrate recognition by yeast and plant sterol 14α-demethylase. Biochem. Biophys. Res. Commun. 183, 1266-1272
29. Ishida, N., Aoyama, Y., Hatanaka, R., Oyama, Y., Imajo, S., Ishiguro, M., Oshima, T., Nakazato, H., Noguchi, T., Maitra, U.S., Mohan, V.P., Sprinson, D.B., and Yoshida, Y. (1988) A single amino acid substitution converts cytochrome P450(14DM) to an inactive form, cytochrome P450SG1: complete primary structures deduced from cloned cDNAs. Biochem. Biophys. Res. Commun. 155, 317-323
30. van Nistelrooy, J.G., van den Brink, J.M., van Kan, J.A., van Gorcom, R.F., and de Waard, M.A. (1996) Isolation and molecular characterization of the gene encoding eburicol 14α-demethylase (CYP51) from Penicillium italicum. Mol. Gen. Genet. 250, 725-733
31. Nishimoto, M., Gotoh, O., Okuda, K., and Noshiro, M. (1991) Structural analysis of the gene encoding rat cholesterol 7α-hydroxylase, the key enzyme for bile acid biosynthesis. J. Biol. Chem. 266, 6467-6471
32. Fujii, T., Nakamura, K., Shibuya, K., Tanae, S., Gotoh, O., Ogawa, T., and Fukuda, H. (1997) Characterization of the structures of the gene and cDNA of the cytochrome P450rm from Rhodotorula minuta which catalyzes formation of isobutene and 4-hydroxylation of benzoate. Mol. Gen. Genet. 256, 115-120
33. Tang, Y.M., Wo, Y.-Y.P., Stewart, J., Hawkins, A.L., Griffin, C.A., Sutter, T.R., and Greenlee, W.F. (1996) Isolation and characterization of the human cytochrome P450 CYP1B1 gene. J. Biol. Chem. 271, 28324-28330
34. Turi, T.G. and Loper, J.C. (1992) Multiple regulatory elements control expression of the gene encoding the Saccharomyces cerevisiae cytochrome P450, lanosterol 14α-demethylase (ERG-11). J. Biol. Chem. 267, 2046-2056
35. Hedges, S.B., Parker, P.H., Sibley, C.G., and Kumar, S. (1996) Continental breakup and the ordinal diversification of birds and mammals. Nature 381, 226-229
36. Hsu, L.C. and Chang, W.C. (1991) Cloning and characterization of a new functional human aldehyde dehydrogenase gene. J. Biol. Chem. 266, 12257-12265
37. Persson, K., Holm, I., and Heby, O. (1995) Cloning and sequencing of an intronless S-adenosylmethionine decarboxylase gene coding for a functional enzyme strongly expressed in the liver. J. Biol. Chem. 270, 5642-5648
38. Eggertsen, G., Olin, M., Andersson, U., Ishida, H., Kubota, S., Hellman, U., Okuda, K.-I., and Bjorkhem, I. (1996) Molecular cloning and expression of rabbit sterol 12α-hydroxylase. J. Biol. Chem. 271, 32269-32275