Enzyme reactions and genes in aflatoxin biosynthesis

Applied Microbiology and Biotechnology

Volumn 64, Issue 6, 2004, Pages 745-755

  Yabe, K ^a   Nakajima, H ^b  

^a NATIONAL FOOD RESEARCH INSTITUTE   (Japan)

^b TOTTORI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AFLATOXIN; AFLATOXIN B; HEXANOIC ACID; STERIGMATOCYSTIN; VERSICOLORIN A;

ENZYME ACTIVITY; FUNGUS;

ASPERGILLUS FLAVUS; ASPERGILLUS PARASITICUS; BIOSYNTHESIS; CARCINOGENIC ACTIVITY; CHEMICAL REACTION; ENZYME ACTIVITY; ENZYME STRUCTURE; GENE CLUSTER; GENE CONTROL; GENE ISOLATION; GENETIC CODE; GENOME; HUMAN; NONHUMAN; SHORT SURVEY;

ACETYL COENZYME A; AFLATOXINS; ANTHRAQUINONES; ASPERGILLUS; DNA-BINDING PROTEINS; FUNGAL PROTEINS; GENE EXPRESSION REGULATION, FUNGAL; GENES, FUNGAL; INTRAMOLECULAR OXIDOREDUCTASES; MOLECULAR STRUCTURE; MULTIGENE FAMILY; STERIGMATOCYSTIN; TRANSCRIPTION FACTORS;

ASPERGILLUS; ASPERGILLUS PARASITICUS; EMERICELLA NIDULANS;

EID: 3142682353     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-004-1566-x     Document Type: Short Survey

References (86)

1. Bennett JW, Christensen SB (1983) New perspective of aflatoxin biosynthesis. Adv Appl Microbiol 29:53-92
2. Bennett JW, Deutsch E (1986) Genetics of mycotoxin biosynthesis. In: Steyn PS, Eleggaar R (eds) Mycotoxins and phycotoxins. Elsevier, Amsterdam, pp 51-64
3. Bennett JW, Lee LS, Cucullu AF (1976) Effect of dichlorvos on aflatoxin and versicolorin A production in Aspergillus parasiticus. Bot Gaz 137:318-324
4. Bergar-Deguee M, Bergar Y (1982) Structure of versicolorone isolated from Aspergillus versicolor. Phytochemistry 21:1449-1451
5. Bhatnagar D, Cleveland TE (1990) Purification and characterization of areductase from Aspergillus parsiticus SRRC 2043 involved in aflatoxin biosynthesis. FASEB J 4:A2164
6. 1 precursor in Aspergillus parasicitus. Appl Environ Microbiol 53:1028-1033
7. Bhatnagar D, Ehrlich KC, Cleveland TE (2003) Molecular genetic analysis and regulation of aflatoxin biosynthesis. Appl Microbiol Biotechnol 61:83-93
8. Brown DW, Adams TH, Keller NP (1996a) Aspergillus has distinct fatty acid synthases for primary and secondary metabolism. Proc Natl Acad Sci USA 93:14873-14877
9. Brown DW, Yu JH, Kelkar HS, Fernandes M, Nesbitt TC, Keller NP, Adams TH, Leonard TJ (1996b) Twenty-five coregulated transcripts define a sterigmatocystin gene cluster in Aspergillus nidulans. Proc Natl Acad Sci USA 93:1418-1422
10. Brown MP, Brouwn-Jenco CS, Payne GA (1999) Genetic and molecular analysis of aflatoxin biosynthesis. Fungal Genet Biol 26:81-98
11. Busby WF, Wogan GN (1985) Aflatoxins. P. 945-1136. In: Esarle CE (ed) Chemical carcinogens, 2nd edn, vol 2. American Chemical Society, Washington, D.C
12. Cary JW, Wright M, Bhatnagar D, Lee R, Chu FS (1996) Molecular characterization of an Aspergillus parasiticus dehydrogenase gene,nor4, located on the aflatoxin biosynthesis gene cluster. Appl Environ Microbiol 62:360-366
13. Cary JW, Barnaby N, Ehrlich KC, Bhatnagar D (1999) Isolation and characterization of experimentally induced aflatoxins biosynthetic pathway deletion mutants of Aspergillus parasiticus. Appl Microbiol Biotechnol 51:808-812
14. Cary JW, Bhatnagar D, Linz JE (2000) Aflatoxins: Biological significance and regulation of biosynthesis. In: Cary JW, Linz JE, Bhatnager D (eds), Microbial food-borne diseases: mechanisms of pathogenesis and toxin synthesis. Technomic, Lancester, Pennsylvania, pp 317-361
15. 1. Mol Gen Genet 248:270-277
16. Chang PK, Yu J, Bhatnagar D, Cleveland TE (1999) The carboxy-terminal portion of the aflatoxin pathway regulatory protein AFLR of Aspergillus parasiticus activates GAL1::LacZ gene expression in Saccharomyces cerevisiae. Appl Environ Microbiol 65:2508-2512
17. Chang PK, Yu J, Ehrlich KC, Boue SM, Montalbano BG, Bhatnagar D, Cleveland TE (2000) The aflatoxin biosynthesis gene adhA in Aspergillus parasiticus is involved in conversion of 5′-hydroxyaverantin to averufin. Appl Environ Microbiol 66:4715-4719
18. Feng GH, Leonard TJ (1995) Characterization of the polyketide synthase gene (pksL) required for aflatoxin biosynthesis in Aspergillus parasiticus. J Bacteriol 177:6246-5624
19. Fernandes M, Keller NP, Adams TH (1998) Sequence-specific binding by Aspergillus nidulans AflR, a C6 zinc cluster protein regulating mycotoxin biosynthesis. Mol Microbiol 28:1355-1365
20. Hamasaki T, Matsui K, Isono K, Hatsuda Y (1973) A new metabolite from Aspergillus versicolor. Agric Biol Chem 37:1769-1770
21. Hitchman TS, Schmidt EW, Trail F, Rarick MD, Linz JE, Townsend CA (2001) Bioorg Chem 29:293-307
22. Horie Y, Udagawa S, Nishimura K, Miyaji M (1988) Distribution of sterigmatocystin-producing Emericella in soil. In: Aibara K, Kumagai S, Ostubo K, Yoshizawa T (eds) Proceeding Jap Assoc/Mycotoxicology, Suppl. I, IUPAC, Mycotoxins and Phycotoxins. Jpn Soc Mycotoxicology, Tokyo, pp 41-42
23. Hutchinson CR (1999) Microbial polyketide synthases: more and more prolific. Proc Natl Acad Sci USA 96:3336-3338
24. Kelkar HS, Keller NP, Adams TH (1996) Aspergillus nidulans stcP encodes an O-methyltransferase that is required for sterigmatocystin biosynthesis. Appl Environ Microbiol 62:4296-4298
25. Kelkar HS, Hernant S, Skloss TW, Haw JF, Keller NP, Adams TH (1997) Aspergillus nidulans stcL encodes a putative cytochrome P-450 monooxygenase required for bisfuran desaturation during aflatoxin/sterigmatocystin biosynthesis. J Biol Chem 272:1589-1594
26. Keller NP, Hohn TM (1997) Metabolic pathway gene clusters in filamentous fungi. Fungal Genet Biol 21:17-29
27. Keller NP, Cleveland TE, Bhatnagar D, Cleveland TE, Ullah AHJ (1993) Purification of a 40-kilodalton methyltransferase active in the aflatoxin biosynthetic pathway. Appl Environ Microbiol 59:479-484
28. Keller NP, Segner S, Bhatnagar D, Adams TH (1995) stcS, a putative P-450 monooxygenase, is required for the conversion of versicolorin A to sterigmatocystin in Aspergillus nidulans. Appl Environ Microbiol 61:3628-3632
29. Keller NP, Watanabe CMH, Kelker HS, Adams TH, Townsend CA (2000) Requirement of monooxygenase-mediated steps for sterigmatocystin biosynthesis by Aspergillus nidulans. Appl Environ Microbiol 66:359-362
30. Kennedy J, Auclar A, Kendrew SG, Park C, Vederas JC, Hutchinson CR (1999) Modulation of polyketide synthase activity by accessory proteins during lovastatin biosynthesis. Science 284:1368-1372
31. Koreeda M, Hulin B, Yoshihara M, Townsend CA, Christensen SB (1985) Synthesis and absolute configuration of (+)-averufin. J Org Chem 50:5426-5428
32. Kusumoto KI, Hsieh DPH (1996) Purification and characterization of the esterases involved in aflatoxin biosynthesis in Aspergillus parasiticus. Can J Microbiol 42:804-810
33. Lee L-W, Chiou C-H, Linz JE (2002) Function of native OmtA in vivo and expression and distribution of this protein in colonies of Aspergillus parasiticus. Appl Environ Microbiol 68:5718-5727
34. Liang SH, Skory CD, Linz JE (1996) Characterization of the function of thever-1A and ver-1B genes involved in aflatoxin biosynthesis in Aspergillus parasiticus. Appl Environ Microbiol 62:4568-4575
35. Lin BK, Anderson JA (1992) Purification and properties of versiconal cyclase from Aspergillus parasiticus. Arch Biochem Biophys 293:67-70
36. Maggon KK, Gupta SK, Venkitasubramanian TA (1977) Biosynthesis of aflatoxins Bacteriol Rev 41:822-855
37. Mahanti N, Bhatnagar D, Cary JW, Joubran J, Linz JE (1996) Structure and function of fas-1A, a gene encoding a putative fatty acid synthase directly involved in aflatoxin biosynthesis in Aspergillus parasiticus. Appl Environ Microbiol 62:191-195
38. 1 carcinogenicity. Proc Soc Exp Bio Med 2003:2213-227
39. Matsushima K, Ando Y, Hamasaki T, Yabe K (1994) Purification and characterization of two versiconal hemiacetal acetate reductases involved in aflatoxin biosynthesis. Appl Environ Microbiol 60:2561-2567
40. 1 precursor between averantin and averufin in the biosynthetic pathway. Appl Environ Microbiol 53:14-16
41. McGuire SM, Silva JC, Casillas EG, Townsend CA (1996) Purification and characterization of versicolorin B synthase from Aspergillus parasiticus. Catalysis of the stereodifferentiating cyclization in aflatoxin biosynthesis essential to DNA interaction Biochem 35:11470-11486
42. Meyers DM, O'Brian G, Du WL, Bhatnagar E, Payne GA (1998) Characterization of aflJ, a gene required for conversion of pathway intermediates to aflatoxin. Appl Environ Microbiol 64:3713-3717
43. Minto RE, Townsend CA (1997) Enzymology and molecular biology of aflatoxin biosynthesis. Chem Rev 97:2537-2555
44. 21- ketosteroids fom Rhodococcus rhodochrous: the isolation and characterization. Biochim Biophys Acta 1251:115-124
45. Motomura M, Chihaya N, Shinozawa T, Hamasaki T, Yabe K (1999) Cloning and characterization of the O-methyltransferase I gene (dmtA) from Aspergillus parasiticus associated with the conversion of demethylsterigmatocystin to sterigmatocystin and dihydrodemethylsterigmatocystin to dihydrosterigatocystin in aflatoxin biosynthesis. Appl Environ Microbiol 65:4987-4994
46. Payne GA (1998) Aflatoxin in maize. Crit Rev Plant Sci 10:423-440
47. Payne GA, Brown MP (1998) Genetics and physiology of aflatoxin biosynthesis. Annu Rev Phytopathol 36:329-362
48. Payne GA, Nystrom GJ, Bhatnagar D, Cleveland TE, Woloshuk CP (1993) Cloning of the afl-2 gene involved in aflatoxin biosynthesis from Aspergillus flavus. Appl Environ Microbiol 59:156-162
49. Prieto R, Woloshuk CP (1997) ord1, an oxidoreductase gene responsible for conversion of O-methylsterigmatocystin to aflatoxin in Aspergillus flavus. Appl Environ Microbiol 63:1661-1666
50. Robens J (2001) The costs of mycotoxin management to the USA: management of aflatoxins in the United States. http://www. apsnet.org/online/feature/ mycotoxin/top.html
51. Sakuno E, Yabe K, Nakajima H (2003) Involvement of two cytosolic enzymes and a novel intermediate, 5′-oxoaverantin, in the pathway from 5′-hydroxyaverantin to averufin in aflatoxin biosynthesis. Appl Environ Microbiol 69:6418-6426
52. Schroeder HW, Cole RS, Grigsby RD, Hein HJ (1974) Inhibition of aflatoxin production and tentative identification of an aflatoxin intermediate "versiconol acetate" from treatment with dichlorvos. Appl Microbiol 27:394-399
53. Silva JC, Townsend CA (1996) Heterologous expression, isolation, and characterization of versicolorin B synthase from Aspergillus parasiticus. J Biol Chem 272:804-813
54. 1 biosynthetic cluster. J Biol Chem 271:13600-13608
55. Skory CD, Chang PK, Cary J, Linz JE (1992) Isolation and characterization of a gene from Aspergillus parasiticus associated with the conversion of versicolorin A to sterigmatocystin in aflatoxin biosynthesis. Appl Environ Microbiol 58:3527-3537
56. Townsend CA, Christensen SB, Trautwein K (1984) Hexanoate as a starter unit in polyketide synthesis. J Am Chem Soc 106:3868-3869
57. Townsend CA, Plavcan KA, Pal K, Brobst SW, Irish MS, Ely EW, Bennett JW (1988a) Hydroxyversicolorone: Isolation and characterization of a potential intermediate in aflatoxin biosynthesis. J Org Chem 53:2472-2477
58. Townsend CA, Whittamore PRO, Brobst SW (1988b) Hydroxyversicolorone: synthesis and incorporation of a new intermediate in aflatoxin biosynthesis. J Chem Soc Chem Commun 726-728
59. Trail F, Chang PK, Cary J, Linz J (1994) Structural and functional analysis of thenor-1 gene involved in the biosynthesis of aflatoxins by Aspergillus parasticus. Appl Environ Microbiol 60:4078-4085
60. Trail F, Mahanti N, Rarick M, Mehigh MR, Liang SH, Zhou R, Linz J (1995a) Physical and transcriptional map of an aflatoxin gene cluster in Aspergillus parasiticus and functional disruption of a gene involved early in the aflatoxin pathway. Appl Environ Microbiol 61:2665-2673
61. Trail F, Mahanti N, Linz J (1995b) Molecular biology of aflatoxin biosynthesis. Microbiol 141:755-765
62. Watanabe CMH, Townsend CA (2002) Initial characterization of a type I fatty acid synthase and polyketide synthase multienzyme complex NorS in the biosynthesis of aflatoxin B (1). Chem Biol 9:981-988
63. 1. Chem Biol 3:463-469
64. 1 biosynthetic genes. FEMS Microbiol Lett 160:169-176
65. Woloshuk CP, Foutz KR, Brewer JF, Bhatnagar D, Cleveland TE, Payne GA (1994) Molecular characterization of aflR, a regulatory locus for aflatoxin biosynthesis. Appl Environ Microbiol 60:2408-2414
66. Yabe K (2002) Pathway and genes of aflatoxin biosynthesis. In: Fierro F, Francisco J (eds) Microbial secondary metabolites: biosynthesis, genetics and regulation, Research Signpost. India, pp 227-251
67. Yabe K, Hamasaki T (1993) Stereochemistry during aflatoxin biosynthesis: cyclase reaction in the conversion of versiconal to versicolorin B and racemization of versiconal hemiacetal acetate. Appl Environ Microbiol 59:2493-2500
68. 2. Appl Environ Microbiol 54:2101-2106
69. Yabe K, Ando Y, Hashimoto J, Hamasaki T (1989) Two distinct O-metyltransferases in aflatoxin biosynthesis. Appl Environ Microbiol 55:2172-2177
70. Yabe K, Ando Y, Hamasaki T (1991a) A metabolic grid among versiconal hemiacetal acetate, versiconol acetate, versiconol and versiconal during aflatoxin biosynthesis. J Gen Microbiol 137:2469-2475
71. 2, Agric Biol Chem 55:1907-1911
72. Yabe K, Nakamura Y, Nakajima H, Ando Y, Hamasaki T (1991c) Enzymatic conversion of norsolorinic acid to averufin in aflatoxin biosynthesis. Appl Environ Microbiol 57:1340-1345
73. Yabe K, Matsuyama Y, Ando Y, Nakajima H, Hamasaki T (1993) Stereochemistry during aflatoxin biosynthesis: conversion of norsolorinic acid to averufin. Appl Environ Microbiol 59:2486-2492
74. Yabe K, Matsushima KI, Koyama T, Hamasaki T (1998) Purification and characterization of O-metyltransferase I involved in conversion of demethylsterigmatocystin to sterigmatocystin and dihydrodemethylsterigamtocsytin to dihydroserimgmatocystin during aflatoxin biosynthesis Appl Environ Microbiol 64:166-171
75. Yabe K, Nakamura M, Hamasaki T (1999) Enzymatic formation of G-group aflatoxins and biosynthetic relationship between G-and B-group aflatoxins. Appl Environ Microbiol 65:3867-3872
76. Yabe K, Chihaya N, Hamamatsu S, Sakuno E, Hamasaki T, Nakajima H, Bennett JW (2003) Enzymatic conversion of averufin to hydroxyversicolorone and elucidation of a novel metabolic grid involved in aflatoxin biosynthesis. Appl Environ Microbiol 69:66-73
77. Yao RC, Hsieh DPH (1974) Step of dichlorvos inhibition in the pathway of aflatoxin biosynthesis. Appl Microbiol 28:52-57
78. Yu JH, Leonard TJ (1995) Sterigmatocystin biosynthesis in Aspergillus nidulans required a novel type I polyketide synthetase. J Bacteriol 177:4792-4800
79. Yu J, Cary JW, Bhatnagar D, Cleveland TE, Keller NP, Chu FS (1993) Cloning and characterization of a cDNA from Aspergillus parasiticus encoding an O-methyltransferase involved in aflatoxin biosynthesis. Appl Environ Microbiol 59:3564-3571
80. Yu JH, Butchko RAE, Fernandes M, Keller NP, Leonard TJ, Adams TH (1996) Conservation of structure and function of the aflatoxin regulatory gene aflR from Aspergillus nidulans and A. flavus. Curr Gent 29:549-555
81. Yu J, Chang PK, Cary JW, Bhatnagar D, Cleveland TE (1997) avnA, a gene encoding a cytochrome P-450 monooxygenase is involved in the conversion of averantin to averufin in aflatoxin biosynthesis in Aspergillus parasiticus. Appl Microbiol Biotechnol 63:1349-1356
82. 2 biosynthesis Appl Environ Microbiol 64:4834-4841
83. Yu J, Woloshuk CP, Bhatnagar D, Cleveland TE (2000a) Cloning and characterization of avfA and omtB genes involved in aflatoxin biosynthesis in three Aspergillus species. Gene 248:157-167
84. Yu J, Chang PK, Bhatnagar D, Cleveland TE (2000b) Genes encoding cytochrome P450 and monooxygenase enzymes define one end of the aflatoxin pathway gene cluster in Aspergillus parasiticus Appl Microbiol Biotechnol 53:583-590
85. Yu J, Chang PK, Bhatnagar D, Cleveland TE (2003) Cloning and functional expression of an esterase gene in Aspergillus parasiticus. Mycopathologia 156:227-234
86. Zhou R, Linz JE (1999) Enzymatic function of the Nor-1 protein in aflatoxin biosynthesis in Aspergillus parasiticus. Appl Environ Microbiol 65:5639-5641