Molecular and functional diversity of fungal cytochrome P450s

Biological and Pharmaceutical Bulletin

Volumn 35, Issue 6, 2012, Pages 833-837

  Ichinose, Hirofumi ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

Functional screening; Fungal P450; Molecular diversity

Indexed keywords

CYTOCHROME P450;

AMINO ACID SEQUENCE; BIOTECHNOLOGY; CATALYSIS; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME STRUCTURE; ENZYME SUBSTRATE COMPLEX; FUNGAL METABOLISM; GENETIC VARIABILITY; GENOME ANALYSIS; MULTIGENE FAMILY; NONHUMAN; REVIEW; SCREENING; SEQUENCE HOMOLOGY; STRUCTURE ACTIVITY RELATION;

EID: 84861888342     PISSN: 09186158     EISSN: 13475215     Source Type: Journal    
DOI: 10.1248/bpb.35.833     Document Type: Review

References (36)

1. Nelson DR, Kamataki T, Waxman DJ, Guengerich FP, Estabrook RW, Feyereisen R, Gonzalez FJ, Coon MJ, Gunsalus IC, Gotoh O, Okuda K, Nebert DW. The P450 superfamily: update on new sequences, gene mapping, accession numbers, early trivial names of enzymes, and nomenclature. DNA Cell Biol., 12, 1-51 (1993).
2. Lewis DFL, Watson E, Lake BG. Evolution of the cytochrome P450 superfamily: sequence alignments and pharmacogenetics. Mutat. Res., 410, 245-270 (1998).
3. Nelson DR. Progress in tracing the evolutionary paths of cytochrome P450. Biochim. Biophys. Acta, 1814, 14-18 (2011).
4. Deng J, Carbone I, Dean RA. The evolutionary history of cytochrome P450 genes in four filamentous ascomycetes. BMC Evol. Biol., 7, 30 (2007).
5. Kelly DE, Kraševec N, Mullins J, Nelson DR. The CYPome (Cytochrome P450 complement) of Aspergillus nidulans. Fungal Genet. Biol., 46 (Suppl. 1), S53-S61 (2009).
6. Park J, Lee S, Choi J, Ahn K, Park B, Park J, Kang S, Lee YH. Fungal cytochrome P450 database. BMC Genomics, 9, 402 (2008).
7. Hawksworth DL. The magnitude of fungal diversity: the 1.5 million species estimate revisited. Mycol. Res., 105, 1422-1432 (2001).
8. Matsuzaki F, Wariishi H. Functional diversity of cytochrome P450s of the white-rot fungus Phanerochaete chrysosporium. Biochem. Biophys. Res. Commun., 324, 387-393 (2004).
9. Ichinose H, Wariishi H, Tanaka H. Bioconversion of recalcitrant 4-methyldibenzothiophene to water-extractable products using lignin-degrading basidiomycete Coriolus versicolor. Biotechnol. Prog., 15, 706-714 (1999).
10. Ferrer-Sevillano F, Fernández-Cañón JM. Novel phacB-encoded cytochrome P450 monooxygenase from Aspergillus nidulans with 3-hydroxyphenylacetate 6-hydroxylase and 3,4-dihydroxyphenyl-acetate 6-hydroxylase activities. Eukaryot. Cell, 6, 514-520 (2007).
11. Prieto R, Woloshuk CP. ord1, an oxidoreductase gene responsible for conversion of O-methylsterigmatocystin to aflatoxin in Aspergillus flavus. Appl. Environ. Microbiol., 63, 1661-1666 (1997).
12. Tudzynski B, Rojas MC, Gaskin P, Hedden P. The gibberellin 20-oxidase of Gibberella fujikuroi is a multifunctional monooxygenase. J. Biol. Chem., 277, 21246-21253 (2002).
13. Kimura M, Tokai T, Takahashi-Ando N, Ohsato S, Fujimura M. Molecular and genetic studies of fusarium trichothecene biosynthesis: pathways, genes, and evolution. Biosci. Biotechnol. Biochem., 71, 2105-2123 (2007).
14. Hirosue S, Tazaki M, Hiratsuka N, Yanai S, Kabumoto H, Shinkyo R, Arisawa A, Sakaki T, Tsunekawa H, Johdo O, Ichinose H, Wariishi H. Insight into functional diversity of cytochrome P450 in the white-rot basidiomycete Phanerochaete chrysosporium: involvement of versatile monooxygenase. Biochem. Biophys. Res. Commun., 407, 118-123 (2011).
15. Nazir KHMNH, Ichinose H, Wariishi H. Construction and application of a functional library of cytochrome P450 monooxygenases from the filamentous fungus Aspergillus oryzae. Appl. Environ. Microbiol., 77, 3147-3150 (2011).
16. Ide M, Ichinose H, Wariishi H. Molecular identification and functional characterization of cytochrome P450 monooxygenases from the brown-rot basidiomycete Postia placenta. Arch. Microbiol., 194, 243-253 (2012).
17. Syed K, Doddapaneni H, Subramanian V, Lam YW, Yadav JS. Genome-to-function characterization of novel fungal P450 monooxygenases oxidizing polycyclic aromatic hydrocarbons (PAHs). Biochem. Biophys. Res. Commun., 399, 492-497 (2010).
18. Subramanian V, Yadav JS. Regulation and heterologous expression of P450 enzyme system components of the white rot fungus Phanerochaete chrysosoporium. Enzyme Microb. Technol., 43, 205-213 (2008).
19. Guengerich FP. Cytochrome P450 enzymes in the generation of commercial products. Nat. Rev. Drug Discov., 1, 359-366 (2002).
20. Chang MCY, Eachus RA, Trieu W, Ro D-K, Keasling JD. Engineering Escherichia coli for production of functionalized terpenoids using plant P450s. Nat. Chem. Biol., 3, 274-277 (2007).
21. Gillam EMJ. Engineering cytochrome p450 enzymes. Chem. Res. Toxicol., 21, 220-231 (2008).
22. Urlacher VB, Eiben S. Cytochrome P450 monooxygenases: perspectives for synthetic application. Trends Biotechnol., 24, 324-330 (2006).
23. Aoyama Y, Yoshida Y, Sato R. Yeast cytochrome P-450 catalyzing lanosterol 14 alpha-demethylation. II. Lanosterol metabolism by purified P-450(14)DM and by intact microsomes. J. Biol. Chem., 259, 1661-1666 (1984).
24. Kelly SL, Lamb DC, Corran AJ, Baldwin BC, Parks LW, Kelly DE. Purification and reconstitution of activity of Saccharomyces cerevisiae P450 61, a sterol delta 22-desaturase. FEBS Lett., 377, 217-220 (1995).
25. Crešnar B, Petrič S. Cytochrome P450 enzymes in the fungal kingdom. Biochim. Biophys. Acta, 1814, 29-35 (2011).
26. Amborabe B-E, Fleurat-Lessard P, Chollet J-F, Roblin G. Anti-fungal effects of salicylic acid and other benzoic acid derivatives towards Eutypa lata: structure-activity relationship. Plant Physiol. Biochem., 40, 1051-1060 (2002).
27. Harwood CS, Parales RE. The beta-ketoadipate pathway and the biology of self-identity. Annu. Rev. Microbiol., 50, 553-590 (1996).
28. Kitazume T, Takaya N, Nakayama N, Shoun H. Fusarium oxysporum fatty-acid subterminal hydroxylase (CYP505) is a membrane-bound eukaryotic counterpart of Bacillus megaterium cytochrome P450BM3. J. Biol. Chem., 275, 39734-39740 (2000).
29. Yadav JS, Doddapaneni H, Subramanian V. P450ome of the white rot fungus Phanerochaete chrysosporium: structure, evolution and regulation of expression of genomic P450 clusters. Biochem. Soc. Trans., 34, 1165-1169 (2006).
30. Nazmul Hussain Nazir KH, Ichinose H, Wariishi H. Molecular characterization and isolation of cytochrome P450 genes from the filamentous fungus Aspergillus oryzae. Arch. Microbiol., 192, 395-408 (2010).
31. Machida M, Asai K, Sano M, Tanaka T, Kumagai T, Terai G, Kusumoto K, Arima T, Akita O, Kashiwagi Y, Abe K, Gomi K, Horiuchi H, Kitamoto K, Kobayashi T, Takeuchi M, Denning DW, Galagan JE, Nierman WC, Yu J, Archer DB, Bennett JW, Bhatnagar D, Cleveland TE, Fedorova ND, Gotoh O, Horikawa H, Hosoyama A, Ichinomiya M, Igarashi R, Iwashita K, Juvvadi PR, Kato M, Kato Y, Kin T, Kokubun A, Maeda H, Maeyama N, Maruyama J, Nagasaki H, Nakajima T, Oda K, Okada K, Paulsen I, Sakamoto K, Sawano T, Takahashi M, Takase K, Terabayashi Y, Wortman JR, Yamada O, Yamagata Y, Anazawa H, Hata Y, Koide Y, Komori T, Koyama Y, Minetoki T, Suharnan S, Tanaka A, Isono K, Kuhara S, Ogasawara N, Kikuchi H. Genome sequencing and analysis of Aspergillus oryzae. Nature, 438, 1157-1161 (2005).
32. Chigu NL, Hirosue S, Nakamura C, Teramoto H, Ichinose H, Wariishi H. Cytochrome P450 monooxygenases involved in anthracene metabolism by the white-rot basidiomycete Phanerochaete chrysosporium. Appl. Microbiol. Biotechnol., 87, 1907-1916 (2010).
33. Kasai N, Ikushiro S, Shinkyo R, Yasuda K, Hirosue S, Arisawa A, Ichinose H, Wariishi H, Sakaki T. Metabolism of mono- and dichloro-dibenzo-p-dioxins by Phanerochaete chrysosporium cytochromes P450. Appl. Microbiol. Biotechnol., 86, 773-780 (2010).
34. Dixon RA, Ferreira D. Genistein. Phytochemistry., 60, 205-211 (2002).
35. Esaki H, Onozaki H, Morinitsu Y, Kawakishi S, Osawa T. Potent antioxidant isoflavones isolated from soybeans fermented with Aspergillus saitoi. Biosci. Biotechnol. Biochem., 62, 740-746 (1998).
36. Isonishi S, Saitou M, Saitou M, Yasuda M, Tanaka T. Differential regulation of the cytotoxicity activity of paclitaxel by orobol and platelet derived growth factor in human ovarian carcinoma cells. Oncol. Rep., 18, 195-201 (2007).