New aspects on lanosterol 14α-demethylase and cytochrome P450 evolution: Lanosterol/cycloartenol diversification and lateral transfer

Journal of Molecular Evolution

Volumn 59, Issue 1, 2004, Pages 51-58

  Režen, Tadeja ^a   Debeljak, Nataša ^a   Kordiš, Dusan ^b   Rozman, Damjana ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

^b JO EF STEFAN INSTITUTE   (Slovenia)

Author keywords

Bacteria; CYP51; Cytochrome P450; Lanosterol 14 demethylase; Mycobacterium tuberculosis; Sterol biosynthesis

Indexed keywords

CYCLOARTENOL; CYTOCHROME P450; ENZYME; LANOSTEROL; STEROL 14ALPHA DEMETHYLASE; UNCLASSIFIED DRUG;

ARCHAEBACTERIUM; ARTICLE; BACTERIUM; CONTROLLED STUDY; EUKARYOTE; FUNGUS; GENE TRANSFER; METHYLOCOCCUS; MOLECULAR EVOLUTION; MYCOBACTERIUM; NONHUMAN; PLANT; PROKARYOTE;

ANIMALIA; ARCHAEA; BACTERIA (MICROORGANISMS); EUKARYOTA; FUNGI; METHYLOCOCCUS; MYCOBACTERIUM; MYCOBACTERIUM TUBERCULOSIS; PROKARYOTA; STREPTOMYCES;

EID: 18844473326     PISSN: 00222844     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00239-004-2603-1     Document Type: Article

References (39)

1. Anandatheerthavarada HK, Amuthan G, Biswas G, Robin MA, Murali R, Waterman MR, Avadhani NG (2001) Evolutionarily divergent electron donor proteins interact with P450MT2 through the same helical domain but different contact points. EMBO J 20:2394-2403
2. Aoyama Y, Noshiro M, Gotoh O, Imaoka S, Funae Y, Kurosawa N, Horiuchi T, Yoshida Y (1996) Sterol 14-demethylase P450 (P45014DM*) is one of the most ancient and conserved P450 species. J Biochem (Tokyo) 119:926-933
3. Aoyama Y, Horiuchi T, Gotoh O, Noshiro M, Yoshida Y (1998) CYP51-like gene of Mycobacterium tuberculosis actually encodes a P450 similar to eukaryotic CYP51. J Biochem (Tokyo) 124:694-696
4. Bellamine A, Mangla AT, Nes WD, Waterman MR (1999) Characterization and catalytic properties of the sterol 14alpha-demethylase from Mycobacterium tuberculosis. Proc Natl Acad Sci USA 96:8937-8942
5. Bellamine A, Mangla AT, Dennis AL, Nes WD, Waterman MR (2001) Structural requirements for substrate recognition of Mycobacterium tuberculosis 14 alpha-demethylase: Implications for sterol biosynthesis. J Lipid Res 42:128-136
6. Bloch KE (1979) Speculations on the evolution of sterol structure and function. CRC Crit Rev Biochem 7:1-5
7. Bode HB, Zeggel B, Silakowski B, Wenzel SC, Reichenbach H, Muller R (2003) Steroid biosynthesis in prokaryotes: identification of myxobacterial steroids and cloning of the first bacterial 2,3(S)-oxidosqualene cyclase from the myxobacterium Stigmatella aurantiaca. Mol Microbiol 47:471-481
8. Boucher Y, Doolittle WF (2000) The role of lateral gene transfer in the evolution of isoprenoid biosynthesis pathways. Mol Microbiol 37:703-716
9. Cavalier-Smith T (2002) The neomuran origin of archaebacteria, the negibacterial root of the universal tree and bacterial mega-classification. Int J Syst Evol Microbiol 52:7-76
10. Cole ST, Brosch R, Parkhill J, Garnier T, Churcher C, Harris D, Gordon SV, Eiglmeier K, Gas S, Barry CE, 3rd, Tekaia F, Badcock K, Basham D, Brown D, Chillingworth T, Connor R, Davies R, Devlin K, Feltwell T, Gentles S, Hamlin N, Holroyd S, Hornsby T, Jagels K, Barrell BG et al. (1998) Deciphering the biology of Mycobacterium tuberculosis from the complete genome sequence. Nature 393:537-544
11. Debeljak N, Fink M, Rozman D (2003) Many facets of mammalian lanosterol 14alpha-demethylase from the evolutionarily conserved cytochrome P450 family CYP51. Arch Biochem Biophys 409:159-171
12. Degtyarenko KN, Archakov AI (1993) Molecular evolution of P450 superfamily and P450-containing monooxygenase systems. FEBS Lett 332:1-8
13. Gamieldien J, Ptitsyn A, Hide W (2002) Eukaryotic genes in Mycobacterium tuberculosis could have a role in pathogenesis and immunomodulation. Trends Genet 18:5-8
14. Gatfield J, Pieters J (2000) Essential role for cholesterol in entry of mycobacteria into macrophages. Science 288:1647-1650
15. Gogarten JP, Doolittle WF, Lawrence JG (2002) Prokaryotic evolution in light of gene transfer. Mol Biol Evol 19:2226-2238
16. Jackson CJ, Lamb DC, Marczylo TH, Warrilow AG, Manning NJ, Lowe DJ, Kelly DE, Kelly SL (2002) A novel sterol 14alpha-demethylase/ferredoxin fusion protein (MCCYP51FX) from Methylococcus capsulatus represents a new class of the cytochrome P450 superfamily. J Biol Chem 277:46959-46965
17. Jackson CJ, Lamb DC, Marczylo TH, Parker JE, Manning NL, Kelly DE, Kelly SL (2003) Conservation and cloning of CYP51: A sterol 14alpha-demethylase from Mycobacterium smegmatis. Biochem Biophys Res Commun 301:558-563
18. Jahnke LL (1992) The effects of growth temperature on the methyl sterol and phospholipid fatty acid composition of Methylococcus capsulatus (Bath). FEMS Microbiol Lett 93: 209-212
19. Joubert BM, Nguyen LN, Matsuda SP, Buckner FS (2001) Cloning and functional characterization of a Trypanosoma brucei lanosterol 14alpha-demethylase gene. Mol Biochem Parasitol 117:115-117
20. Karlin S (2001) Detecting anomalous gene clusters and pathogenicity islands in diverse bacterial genomes. Trends Microbiol 9:335-343
21. Lamb DC, Kelly DE, Kelly SL (1998) Molecular diversity of sterol 14alpha-demethylase substrates in plants, fungi and humans. FEBS Lett 425:263-265
22. Lamb DC, Fowler K, Kieser T, Manning N, Podust LM, Waterman MR, Kelly DE, Kelly SL (2002a) Sterol 14alpha-demethylase activity in Streptomyces coelicolor A3(2) is associated with an unusual member of the CYP51 gene family. Biochem J 364:555-562
23. Lamb DC, Skaug T, Song HL, Jackson CJ, Podust LM, Waterman MR, Kell DB, Kelly DE, Kelly SL (2002b) The cytochrome P450 complement (CYPome) of Streptomyces coelicolor A3(2). J Biol Chem 277:24000-24005
24. Lamb DC, Ikeda H, Nelson DR, Ishikawa J, Skaug T, Jackson C, Omura S, Waterman MR, Kelly SL (2003) Cytochrome P450 complement of avermectin-producer Streptomyces avermitilis and comparison to that of Streptomyces coelicolor A3(2). Biochem Biophys Res Commun 307:610-619
25. Lepesheva GI, Podust LM, Bellamine A, Waterman MR (2001) Folding requirements are different between sterol 14alpha-demethylase (CYP51) from Mycobacterium tuberculosis and human or fungal orthologs. J Biol Chem 276:28413-28420
26. Liendo A, Visbal G, Piras MM, Piras R, Urbina JA (1999) Sterol composition and biosynthesis in Trypanosoma cruzi amastigotes. Mol Biochem Parasitol 104:81-91
27. McLean KJ, Scrutton NS, Munro AW (2003) Kinetic, spectroscopic and thermodynamic characterization of the Mycobacterium tuberculosis adrenodoxn reductase homologue FprA. Biochem J 372:317-327
28. Nelson DR (1998) Metazoan cytochrome P450 evolution. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol 121:15-22
29. Nelson DR (1999) Cytochrome P450 and the individuality of species. Arch Biochem Biophys 369:1-10
30. Nes WD, Norton RA, Crumley FG, Madigan SJ, Katz ER (1990) Sterol phylogenesis and algal evolution. Proc Natl Acad Sci USA 87:7565-7569
31. Ochman H, Lawrence JG, Groisman EA (2000) Lateral gene transfer and the nature of bacterial innovation. Nature 405:299-304
32. Thompson JD, Higgins DG, Gibson TJ (1994) CLUSTAL W: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice. Nucleic Acids Res 22:4673-4680
33. Tizard M, Bull T, Millar D, Doran T, Martin H, Sumar N, Ford J, Hermon-Taylor J (1998) A low G + C content genetic island in Mycobacterium avium subsp. paratuberculosis and M. avium subsp. silvaticum with homologous genes in Mycobacterium tuberculosis. Microbiology 144:3413-3423
34. Van de Peer Y, De Wachter R (1997) Construction of evolutionary distance trees with TREECON for Windows: Accounting for variation in nucleotide substitution rate among sites. Comput Appl Biosci 13:227-230
35. Volkman K (2003) Sterols in microorganisms. Appl Microbiol Biotechnol 60:495-506
36. Wilding EI, Brown JR, Bryant AP, Chalker AF, Holmes DJ, Ingraham KA, Iordanescu S, So CY, Rosenberg M, Gwynn MN (2000) Identification, evolution, and essentiality of the mevalonate pathway for isopentenyl diphosphate biosynthesis in gram-positive cocci. J Bacteriol 182:4319-4327
37. Wolf YI, Kondrashov AS, Koonin EV (2000) Interkingdom gene fusions. Genome Biol 1:1-13
38. Yoshida Y, Noshiro M, Aoyama Y, Kawamoto T, Horiuchi T, Gotoh O (1997) Structural and evolutionary studies on sterol 14-demethylase P450 (CYP51), the most conserved P450 monooxygenase: II. Evolutionary analysis of protein and gene structures. J Biochem (Tokyo) 122:1122-1128
39. Yoshida Y, Aoyama Y, Noshiro M, Gotoh O (2000) Sterol 14-demethylase P450 (CYP51) provides a breakthrough for the discussion on the evolution of cytochrome P450 gene superfamily. Biochem Biophys Res Commun 273:799-804