Enzyme reactions and genes in aflatoxin biosynthesis (original) (raw)
Bennett JW, Christensen SB (1983) New perspective of aflatoxin biosynthesis. Adv Appl Microbiol 29:53–92 CASPubMed Google Scholar
Bennett JW, Deutsch E (1986) Genetics of mycotoxin biosynthesis. In: Steyn PS,Eleggaar R (eds) Mycotoxins and phycotoxins. Elsevier, Amsterdam, pp 51–64
Bennett JW, Lee LS, Cucullu AF (1976) Effect of dichlorvos on aflatoxin and versicolorin A production in Aspergillus parasiticus. Bot Gaz 137:318–324 ArticleCAS Google Scholar
Bergar-Deguee M, Bergar Y (1982) Structure of versicolorone isolated from Aspergillus versicolor. Phytochemistry 21:1449–1451 Article Google Scholar
Bhatnagar D, Cleveland TE (1990) Purification and characterization of a reductase from Aspergillus parsiticus SRRC 2043 involved in aflatoxin biosynthesis. FASEB J 4:A2164 Google Scholar
Bhatnagar D, McCormick SP, Lee LS, Hill RA (1987) Identification of_O_-methylsterigmatocystin as an aflatoxin B1/G1 precursor in Aspergillus parasicitus. Appl Environ Microbiol 53:1028–1033 CASPubMed Google Scholar
Bhatnagar D, Ehrlich KC, Cleveland TE (2003) Molecular genetic analysis and regulation of aflatoxin biosynthesis. Appl Microbiol Biotechnol 61:83–93 CASPubMed Google Scholar
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 ArticleCASPubMed Google Scholar
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 ArticleCASPubMed Google Scholar
Brown MP, Brouwn-Jenco CS, Payne GA (1999) Genetic and molecular analysis of aflatoxin biosynthesis. Fungal Genet Biol 26:81–98 ArticleCASPubMed Google Scholar
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
Cary JW, Wright M, Bhatnagar D, Lee R, Chu FS (1996) Molecular characterization of an Aspergillus parasiticus dehydrogenase gene,norA, located on the aflatoxin biosynthesis gene cluster. Appl Environ Microbiol 62:360–366 Google Scholar
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 ArticleCASPubMed Google Scholar
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
Chang PK, Cary JW, Yu J, Bhatnagar D, Cleveland TE (1995) Aspergillus parasiticus polyketide synthetase gene, pksA, a homolog of Aspergillus nidulans wA, required for aflatoxin B1. Mol Gen Genet 248:270–277 CASPubMed Google Scholar
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 CASPubMed Google Scholar
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 Google Scholar
Feng GH, Leonard TJ (1995) Characterization of the polyketide synthase gene (pksL) required for aflatoxin biosynthesis in Aspergillus parasiticus. J Bacteriol 177:6246–5624 CAS Google Scholar
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 CASPubMed Google Scholar
Hamasaki T, Matsui K, Isono K, Hatsuda Y (1973) A new metabolite from Aspergillus versicolor. Agric Biol Chem 37:1769–1770 CAS Google Scholar
Hitchman TS, Schmidt EW, Trail F, Rarick MD, Linz JE, Townsend CA (2001) Bioorg Chem 29:293–307 ArticleCAS Google Scholar
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
Hutchinson CR (1999) Microbial polyketide synthases: more and more prolific. Proc Natl Acad Sci USA 96:3336–3338 CASPubMed Google Scholar
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 CASPubMed Google Scholar
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 ArticleCASPubMed Google Scholar
Keller NP, Hohn TM (1997) Metabolic pathway gene clusters in filamentous fungi. Fungal Genet Biol 21:17–29 ArticleCASPubMed Google Scholar
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 CASPubMed Google Scholar
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 CASPubMed Google Scholar
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 Google Scholar
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 ArticleCASPubMed Google Scholar
Koreeda M, Hulin B, Yoshihara M, Townsend CA, Christensen SB (1985) Synthesis and absolute configuration of (+)-averufin. J Org Chem 50:5426–5428 CAS Google Scholar
Kusumoto KI, Hsieh DPH (1996) Purification and characterization of the esterases involved in aflatoxin biosynthesis in Aspergillus parasiticus. Can J Microbiol 42:804–810 Google Scholar
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 CASPubMed Google Scholar
Liang SH, Skory CD, Linz JE (1996) Characterization of the function of the_ver-1A_ and ver-1B genes involved in aflatoxin biosynthesis in Aspergillus parasiticus. Appl Environ Microbiol 62:4568–4575 CASPubMed Google Scholar
Lin BK, Anderson JA (1992) Purification and properties of versiconal cyclase from Aspergillus parasiticus. Arch Biochem Biophys 293:67–70 CASPubMed Google Scholar
Maggon KK, Gupta SK, Venkitasubramanian TA (1977) Biosynthesis of aflatoxins Bacteriol Rev 41:822–855 CAS Google Scholar
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 CASPubMed Google Scholar
Massey TE, Stewart RK, Daniels JM, Liu L (1995) Biochemical and molecular aspects of mammalian susceptibility to aflatoxin B1 carcinogenicity. Proc Soc Exp Bio Med 2003:2213–227 Google Scholar
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 CAS Google Scholar
McCormick SP, Bhatnagar D, Lee LS (1987) Averufanin is an aflatoxin B1 precursor between averantin and averufin in the biosynthetic pathway. Appl Environ Microbiol 53:14–16 CASPubMed Google Scholar
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 ArticleCAS Google Scholar
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 CASPubMed Google Scholar
Minto RE, Townsend CA (1997) Enzymology and molecular biology of aflatoxin biosynthesis. Chem Rev 97:2537–2555 ArticleCAS Google Scholar
Miyamoto M, Matsumoto J, Iwaya T, Itagaki E (1995) Bacterial steroid monooxygenase catalyzing the Baeyer-Villiger oxidation of C21-ketosteroids from_Rhodococcus rhodochrous_: the isolation and characterization. Biochim Biophys Acta 1251:115–124 ArticleCASPubMed Google Scholar
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 CASPubMed Google Scholar
Payne GA (1998) Aflatoxin in maize. Crit Rev Plant Sci 10:423–440 Google Scholar
Payne GA, Brown MP (1998) Genetics and physiology of aflatoxin biosynthesis. Annu Rev Phytopathol 36:329–362 ArticleCAS Google Scholar
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 CASPubMed Google Scholar
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 Google Scholar
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 ArticleCASPubMed Google Scholar
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 CASPubMed Google Scholar
Silva JC, Townsend CA (1996) Heterologous expression, isolation, and characterization of versicolorin B synthase from Aspergillus parasiticus. J Biol Chem 272:804–813 Article Google Scholar
Silva JC, Minto RE, Barry III CE, Holland KA, Townsend CA (1996) Isolation and characterization of the versicolorin B synthase gene from Aspergillus parasiticus: expression of the aflatoxin B1 biosynthetic cluster. J Biol Chem 271:13600–13608 ArticleCASPubMed Google Scholar
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 Google Scholar
Townsend CA, Christensen SB, Trautwein K (1984) Hexanoate as a starter unit in polyketide synthesis. J Am Chem Soc 106:3868–3869 CAS Google Scholar
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 CAS Google Scholar
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
Trail F, Chang PK, Cary J, Linz J (1994) Structural and functional analysis of the_nor-1_ gene involved in the biosynthesis of aflatoxins by Aspergillus parasticus. Appl Environ Microbiol 60:4078–4085 CASPubMed Google Scholar
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 CASPubMed Google Scholar
Trail F, Mahanti N, Linz J (1995b) Molecular biology of aflatoxin biosynthesis. Microbiol 141:755–765 CASPubMed Google Scholar
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 ArticleCASPubMed Google Scholar
Watanabe CMH, Wilson D, Linz JE, Townsend CA (1996) Demonstration of the catalytic roles and evidence for the physical association of type I fatty acid syntheses and a polyketide synthase in the biosynthesis of aflatoxin B1. Chem Biol 3:463–469 CASPubMed Google Scholar
Woloshuk CP, Prieto R (1998) Genetic organization and function of the aflatoxin B1biosynthetic genes. FEMS Microbiol Lett 160:169–176 ArticleCASPubMed Google Scholar
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 CASPubMed Google Scholar
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
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 CASPubMed Google Scholar
Yabe K, Ando Y, Hamasaki T (1988) Biosynthetic relationship among aflatoxins B1, B2, G1, and G2. Appl Environ Microbiol 54:2101–2106 CASPubMed Google Scholar
Yabe K, Ando Y, Hashimoto J, Hamasaki T (1989) Two distinct _O_-metyltransferases in aflatoxin biosynthesis. Appl Environ Microbiol 55:2172–2177 CASPubMed Google Scholar
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 CASPubMed Google Scholar
Yabe K, Ando Y, Hamasaki T (1991b) Desaturase activity in the branching step between aflatoxins B1 and G1 and aflatoxins B2 and G2, Agric Biol Chem 55:1907–1911 Google Scholar
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 CASPubMed Google Scholar
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 CASPubMed Google Scholar
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 Google Scholar
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 CASPubMed Google Scholar
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 ArticleCASPubMed Google Scholar
Yao RC, Hsieh DPH (1974) Step of dichlorvos inhibition in the pathway of aflatoxin biosynthesis. Appl Microbiol 28:52–57 CASPubMed Google Scholar
Yu JH, Leonard TJ (1995) Sterigmatocystin biosynthesis in _Aspergillus nidulans_required a novel type I polyketide synthetase. J Bacteriol 177:4792–4800 CASPubMed Google Scholar
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 CASPubMed Google Scholar
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 ArticleCAS Google Scholar
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 CAS Google Scholar
Yu J, Chang PK, Ehrlich KC, Cary JW, Montalbano B, Dyer JM, Bhatnagar D, Cleveland TE (1998) Characterization of the critical amino acids of an Aspergillus parasiticus_cytochrome P450 monooxygenase encoded by_ordA involved in aflatoxin B1, G1, B2, and G2 biosynthesis Appl Environ Microbiol 64:4834–4841 Google Scholar
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 ArticleCASPubMed Google Scholar
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 Google Scholar
Yu J, Chang PK, Bhatnagar D, Cleveland TE (2003) Cloning and functional expression of an esterase gene in Aspergillus parasiticus. Mycopathologia 156:227–234 ArticleCAS Google Scholar
Zhou R, Linz JE (1999) Enzymatic function of the Nor-1 protein in aflatoxin biosynthesis in Aspergillus parasiticus. Appl Environ Microbiol 65:5639–5641 Google Scholar