Biosynthesis of hexahydroxyperylenequinone melanin via oxidative aryl coupling by cytochrome P-450 in Streptomyces griseus

Journal of Bacteriology

Volumn 187, Issue 23, 2005, Pages 8149-8155

  Funa, Nobutaka ^a   Funabashi, Masanori ^a   Ohnishi, Yasuo ^a   Horinouchi, Sueharu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450; DNA FRAGMENT; FERREDOXIN NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE REDUCTASE; HEXAHYDROXYPERYLENEQUINONE MELANIN; MELANIN; POLYKETIDE; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; ENZYME PURIFICATION; FUNGUS; GRAM POSITIVE BACTERIUM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; NUCLEOTIDE SEQUENCE; PLASMID; POLYMERASE CHAIN REACTION; PRIORITY JOURNAL; STREPTOMYCES GRISEUS; STREPTOMYCETACEAE; ULTRAVIOLET IRRADIATION;

ACYLTRANSFERASES; CYTOCHROME P-450 ENZYME SYSTEM; DIHYDROXYPHENYLALANINE; GENE DELETION; MELANINS; MOLECULAR SEQUENCE DATA; NAPHTHOLS; PERYLENE; SPORES, BACTERIAL; STREPTOMYCES GRISEUS; ULTRAVIOLET RAYS;

ANIMALIA; BACTERIA (MICROORGANISMS); EUKARYOTA; FUNGI; POSIBACTERIA; PROKARYOTA; SPINACIA OLERACEA; STREPTOMYCES; STREPTOMYCES GRISEUS; STREPTOMYCETACEAE; STREPTOMYCINEAE;

EID: 28044436696     PISSN: 00219193     EISSN: None     Source Type: Journal    
DOI: 10.1128/JB.187.23.8149-8155.2005     Document Type: Article

References (27)

1. Allport, D. C., and J. D. Bu'Lock. 1958. The pigmentation and cell-wall material of Daldinia sp. J. Chem. Soc. 1958:4090-4094.
2. Bell, A. A., and M. H. Wheeler. 1986. Biosynthesis and function of fungal melanins. Annu. Rev. Phytopathol. 24:411-451.
3. Challis, G. L., and D. A. Hopwood. 2003. Synergy and contingency as driving forces for the evolution of multiple secondary metabolite production by Streptomyces species. Proc. Natl. Acad. Sci. USA 100:14555-14561.
4. Cortés, J., J. Velasco, G. Foster, A. P. Blackaby, B. A. Rudd, and B. Wilkinson. 2002. Identification and cloning of a type III polyketide synthase required for diffusible pigment biosynthesis in Saccharopolyspora erythraea. Mol. Microbiol. 44:1213-1224.
5. Endo, K., K. Kamo, K. Hosono, T. Beppu, and K. Ueda. 2001. Characterization of mutants defective in melanogenesis and a gene for tyrosinase of Streptomyces griseus. J. Antibiot. 54:789-796.
6. Fujii, I., Y. Mon, A. Watanabe, Y. Kubo, G. Tsuji, and Y. Ebizuka. 2000. Enzymatic synthesis of 1,3,6,8-tetrahydroxynaphthalene solely from malonyl coenzyme A by a fungal iterative type I polyketide synthase PKS1. Biochemistry 39:8853-8858.
7. Funa, N, M. Funabashi, E. Yoshimura, and S. Horinouchi. 2005. A novel quinone-forming monooxygenase family involved in modification of aromatic polyketides. J. Biol. Chem. 280:14514-14523.
8. Funa, N., Y. Ohnishi, I. Fujii, M. Shibuya, Y. Ebizuka, and S. Horinouchi. 1999. A new pathway for polyketide synthesis in microorganisms. Nature 400:897-599.
9. Ichinose, K., Y. Ebizuka, and U. Sankawa. 2001. Mechanistic studies on the biomimetic reduction of tetrahydroxynaphthalene, a key intermediate in melanin biosynthesis. Chem. Pharm. Bull. 49:192-196.
10. Izumikawa, M., P. R. Shipley, J. N. Hopke, T. O'Hare, L. Xiang, J. P. Noel, and B. S. Moore. 2003. Expression and characterization of the type III polyketide synthase 1,3,6,8-tetrahydroxynaphthalene synthase from Streptomyces coelicolor A3(2). J. Ind. Microbiol. Biotechnol. 30:510-515.
11. Kieser, T., M. J. Bibb, M. J. Buttner, K. F. Chater, and D. A. Hopwood. 2000. Practical Streptomyces genetics. The John Innes Foundation, Norwich, United Kingdom.
12. Maniatis, T., E. F. Fritsch, and J. Sambrook. 1982. Molecular cloning: a laboratory manual. Cold Spring Harbor Laboratory, Cold Spring Harbor, N.Y.
13. Montellano, P. R., and J. J. De Voss. 2002. Oxidizing species in the mechanism of cytochrome P450. Nat. Prod. Rep. 19:477-493.
14. Munro, A. W., and J. G. Lindsay. 1996. Bacterial cytochromes P-450. Mol. Microbiol. 20:1115-1125.
15. Noasanchuk, J. D., and A. Casadevall. 2003. The contribution of melanin to microbial pathogenesis. Cell. Microbiol. 5:203-223.
16. Omura, T., and R. Sato. 1964. The carbon monoxide-binding pigment of liver microsomes. J. Biol. Chem. 239:2370-2385.
17. Pylypenko, O., F. Vitali, K. Zerbe, J. A. Robinson, and I. Schlichting. 2003. Crystal structure of OxyC, a cytochrome P450 implicated in an oxidative C-C coupling reaction during vancomycin biosynthesis. J. Biol. Chem. 278:46727-46733.
18. Romero-Martinez, R., M. Wheeler, A. Guerrero-Plata, G. Rico, and H. Torres-Guerrero. 2000. Biosynthesis and function of melanin in Sporothrix schenckii. Infect. Immun. 68:3696-3703.
19. Takano, E., J. White, C. J. Thompson, and M. J. Bibb. 1995. Construction of thiostrepton-inducible, high-copy-number expression vectors for use in Streptomyces spp. Gene 166:133-137.
20. Trower, M. K., S. F. Sariaslani, and D. P. O'Keefe. 1989. Purification and characterization of a soybean flour-induced cytochrome P-450 from Streptomyces griseus. J. Bacteriol. 171:1781-1787.
21. Ueda, K., K.-M. Kim, T. Beppu, and S. Horinouchi. 1995. Overexpression of a gene cluster encoding a chalcone synthase-like protein confers redbrown pigment production in Streptomyces griseus. J. Antibiot. 48:638-646.
22. Wang, H.-K., J.-X. Xie, J.-J. Chang, K.-M. Hwang, S.-Y. Liu, L.-M. Ballas, J. B. Jiang, and K.-H. Lee. 1992. Antitumor agents. 134. New Shiraiachrome-A- and Calphostin-C-related perylene derivatives as cytotoxic and antiviral agents and inhibitors of protein kinase C. J. Med. Chem. 35:2717-2721.
23. Wiess, U., L. Merlini, and G. Nasini. 1987. Naturally occurring perylenequinones. Prog. Chem. Org. Nat. Prod. 52:1-71.
24. Williams, S. T., M. Goodfellow, G. Alderson, E. M. Wellington, P. H. Sneath, and M. J. Sackin. 1983. Numerical classification of Streptomyces and related genera. J. Gen. Microbiol. 129:1743-1813.
25. Williams, S. T., M. Goodfellow, E. M. Wellington, J. C. Vickers, G. Alderson, P. H. Sneath, M. J. Sackin, and A. M. Mortimer. 1983. A probability matrix for identification of some streptomycetes. J. Gen. Microbiol. 129:1815-1830.
26. Zenk, M. H., R. Gerardy, and R. Stadler. 1989. Phenol oxidative coupling of benzylisoquinoline alkaloids catalysed by regio- and stereo-selective cytochrome P-450 linked plant enzymes: salutaridine and berbamunine. J. Chem. Soc. Chem. Commun. 1989:1725-1727.
27. Zhao, B., P. Guengerich, A. Bellamine, D. C. Lamb, M. Izumikawa, L. Lei, L. M. Podust, M. Sundaramoorthy, J. A. Kalaitzis, L. M. Reddy, S. L. Kelly, B. S. Moore, D. Stec, M. Voehler, J. R. Falck, T. Shimada, and M. R. Waterman. 2005. Binding of two flaviolin substrate molecules, oxidative coupling, and crystal structure of Streptomyces coelicolor A3(2) cytochrome P450 158A2. J. Biol. Chem. 280:11597-11607.