Biosynthesis of dothistromin

Mycopathologia

Volumn 162, Issue 3, 2006, Pages 201-213

  Bradshaw, Rosie E ^a   Zhang, Shuguang ^a  

^a MASSEY UNIVERSITY   (New Zealand)

Author keywords

Aflatoxin; Dothistroma needle blight; Epoxide hydrolase; Gene cluster; Mycotoxin; Sterigmatocystin

Indexed keywords

ANTHRAQUINONE DERIVATIVE; DOTHISTROMIN; MYCOTOXIN;

ASCOMYCETES; BIOSYNTHESIS; CHROMOSOME; FUNGAL GENE; GENE EXPRESSION PROFILING; GENETIC TRANSCRIPTION; GENETICS; GROWTH, DEVELOPMENT AND AGING; METABOLISM; MICROBIOLOGY; MULTIGENE FAMILY; PATHOGENICITY; PINE; PLANT DISEASE; REVIEW; SEQUENCE HOMOLOGY;

ANTHRAQUINONES; ASCOMYCOTA; CHROMOSOMES, FUNGAL; GENE EXPRESSION PROFILING; GENES, FUNGAL; MULTIGENE FAMILY; MYCOTOXINS; PINUS; PLANT DISEASES; SEQUENCE HOMOLOGY, NUCLEIC ACID; TRANSCRIPTION, GENETIC;

DOTHISTROMA; FUNGI; MYCOSPHAERELLA PINI;

EID: 33748362233     PISSN: 0301486X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11046-006-0054-5     Document Type: Review

References (62)

1. RE Bradshaw 2004 Dothistroma (red-band) needle blight of pines and the dothistromin toxin: a review For Pathol 34 163 185
2. AJ Woods KD Coates A Hamann 2005 Is an unprecedented Dothistroma needle blight epidemic related to climate change? Bioscience 55 761 769
3. Bassett C, Buchanan M, Gallagher RT, Hodges R. A toxic difuroanthraquinone from Dothistroma pini. Chem Ind (London) 1970; 1659-1660
4. G Assante R Locci L Camarada L Merlini G. Nasini 1977 Screening of the genus Cercospora for secondary metabolites Phytochemistry 16 243 247
5. L Shain RA Franich 1981 Induction of Dothistroma blight symptoms with dothistromin Physiol. Plant Pathol. 19 49 55
6. RT Gallagher R Hodges 1972 The chemistry of dothistromin, a difuroanthraquinone from Dothistroma pini Aust J Chem 25 2399 2407
7. Bear CA, Waters JM, Waters TN. Crystal structure and absolute configuration of a derivative of dothistromin, a fungal toxin implicated in pine-needle blight. J Chem Soc Perkin Trans II 1972; 2375-2378
8. G Assante L Camarda L Merlini G. Nasini 1977 Dothistromin and 2-epidothistromin from Cercospora smilacis Phytochemistry 16 125 126
9. G Assante 1985 Isolation and characterization of new dothstromins from Mycosphaerella laricina hart Phytopathol Mediterr 24 271 273
10. PD Gadgil 1967 Infection of Pinus radiata needles by Dothistroma pini N Z J. Bot. 5 498 503
11. P Debnam R Narayan N Cranshaw WT Jones M Nicol PHS Reynolds 1994 Role of the fungal toxin dothistromin in resistance towards Dothistroma needle blight in Pinus radiata Proceedings of the American Society of Plant Physiologists Annual Meeting Portland, Oregon
12. RA Franich MJ Carson SD Carson 1986 Synthesis and accumulation of benzoic acid in Pinus radiata needles in response to tissue injury by dothistromin, and correlation with resistance of P. radiata families to Dothistroma pini Physiol Mol Plant Pathol 28 267 286
13. DW Edwards J Walker 1978 Dothistroma needle blight in Australia Aust For Res 8 125 137
14. WT Jones D Harvey SD Jones S Fielder P Debnam PHS Reynolds 1993 Competitive ELISA employing monoclonal antibodies specific for dothistromin Food Agric Immunol 5 187 197
15. RE Bradshaw RJ Ganley WT Jones PS Dyer 2000 High levels of dothistromin toxin produced by the forest pathogen Dothistroma pini Mycol Res 104 325 332
16. I Barnes PW Crous BD Wingfield MJ Wingfield 2004 Multigene phylogenies reveal that red band needle bight of Pinus is caused by two distinct species of Dothistroma, D. septosporum and D. pini Stud Mycol 50 551 565
17. Gallagher RT. The structure of dothistromin. (Dissertation). Massey University, Palmerston North, New Zealand, 1971
18. BW Horn JW Dorner 2001 Effect of competition and adverse culture conditions on aflatoxin production by Aspergillus flavus through successive generations Mycologia 94 741 751
19. AV Danks R Hodges 1974 Polyhydroxyanthraquinones from Dothistroma pini Aust J Chem 27 1603 1606
20. 13C NMR study of the biosynthesis of the anthraquinone dothistromin by Dothistroma pini Phytochemistry 17 1743 1745
21. RE Bradshaw D Bhatnagar RJ Ganley CJ Gillman BJ Monahan JM Seconi 2002 Dothistroma pini, a forest pathogen, contains homologs of aflatoxin biosynthetic pathway genes Appl Environ Microbiol 68 2885 2892
22. KM Henry CA Townsend 2005 Ordering the reductive and cytochrome P450 oxidative steps in demethylsterigmatocystin formation yields general insights into the biosynthesis of aflatoxin and related fungal metabolites J Am Chem Soc 127 3724 3733
23. 1 biosynthesis Mol Gen Genet 248 270 277
24. GH Feng TJ Leonard 1995 Characterization of the polyketide synthase gene (pksL1) required for aflatoxin biosynthesis in Aspergillus parasiticus J Bacteriol 177 6246 6254
25. J Yu P-K Chang KC Ehrlich JW Cary D Bhatnagar TE Cleveland GA Payne JE Linz CP Woloshuk JW Bennett 2004 Clustered pathway genes in aflatoxin biosynthesis Appl. Environ. Microbiol. 70 1253 1262
26. DW Brown J-H Yu HS Kelkar M Fernandes TC Nesbitt NP Keller TH Adams TJ Leonard 1996 Twenty-five coregulated transcripts define a sterigmatocystin gene cluster in Aspergillus nidulans Proc Natl Acad Sci USA 93 1418 1422
27. Zhang Y, Keller N, Tsitsigiannis D. Secondary metabolite gene clusters. In: An Z, ed. Handbook of Industrial Mycology, Marcel Dekker, New York, 2005: 355-385
28. P-K Chang J Yu J-H Yu 2004 aflT, a MFS transporter-encoding gene located in the aflatoxin gene cluster, does not have a significant role in aflatoxin secretion Fungal Genet. Biol. 41 911 920
29. JF Martin J Casqueiro P Liras 2005 Secretion systems for secondary metabolites: How producer cells send out messages of intercellular communication Curr Opin Microbiol 8 282 293
30. J Yu CP Woloshuk D Bhatnagar TE Cleveland 2000 Cloning and characterization of avfA and omtB genes involved in aflatoxin biosynthesis in three Aspergillus species Gene 248 157 167
31. K Yabe N Chihaya S Hamamatsu E Sakuno T Hamasaki H Nakajima JW Bennett 2003 Enzymatic conversion of averufin to hydroxyversicolorone and elucidation of a novel metabolic grid involved in aflatoxin biosynthesis Appl Environ Microbiol 69 66 73
32. Y Wen H Hatabayashi H Arai K Kitamoto K Yabe 2005 Function of the cypX and moxY genes in aflatoxin biosynthesis in Aspergillus parasiticus Appl Environ Microbiol 71 3192 3198
33. J Yu P-K Chang D Bhatnagar TE Cleveland 2000 Genes encoding cytochrome P450 and monooxygenase enzymes define one end of the aflatoxin pathway gene cluster in Aspergillus paraciticus Appl Microbiol Biotechnol 53 583 590
34. E Sakuno Y Wen H Hatabayashi H Arai C Aoki K Yabe H Nakajima 2005 Aspergillus parasiticus cyclase catalyzes two dehydration steps in aflatoxin biosynthesis Appl Environ Microbiol 71 2999 3006
35. M Arand H Hemmer H Durk J Baratti A Archelas R Furtoss F Oesch 1999 Cloning and molecular characterization of a soluble epoxide hydrolase from Aspergillus niger that is related to mammalian microsomal epoxide hydrolase Biochem J 344 273 280
36. 1 detoxification Toxicol Sci 65 35 42
37. CM Coyle DG Panaccione 2005 An ergot alkaloid biosynthesis gene and clustered hypothetical genes from Aspergillus fumigatus Appl Environ Microbiol 71 3112 3118
38. SF Covert 1998 Supernumerary chromosomes in filamentous fungi Curr. Genet. 33 311 319
39. R Hatta K Ito Y Hosaki T Tanaka A Tanaka M Yamamoto K Akimitsu T Tsuge 2002 A conditionally dispensable chromosome controls host-specific pathogenicity in the fungal plant pathogen Alternaria alternata Genetics 161 59 70
40. CD Skory P Chang JE Linz 1993 Regulated expression of the nor-1 and ver-1 genes associated with aflatoxin biosynthesis Appl Environ Microbiol 59 1642 1646
41. GH Feng TJ Leonard 1998 Culture conditions control expression of the genes for aflatoxin and sterigmatocystin biosynthesis in Aspergillus parasiticus and Aspergillus nidulans Appl Environ Microbiol 64 2275 2277
42. PJ Cotty 1988 Aflatoxin and sclerotial production by Aspergillus flavus: Influence of pH Phytopathology 78 1250 1253
43. J Morrice DA [tmp] MacKenzie AJ Parr DB Archer 1998 Isolation and characterization of the acetyl-CoA carboxylase gene from Aspergillus nidulans Curr Genet 34 379 385
44. NP Keller C Nesbitt B Sarr TD Phillips GB Burow 1997 pH regulation of sterigmatocystin and aflatoxin biosynthesis in Aspergillus spp Phytopathology 87 643 648
45. MH Ivory 1967 Spore germination and growth in culture of Dothistroma pini var keniensis Trans Br Mycol Soc 50 563 572
46. KC Ehrlich BG Montalbano PJ Cotty 2003 Sequence comparison of aflR from different Aspergillus species provides evidence for variability in regulation of aflatoxin production Fungal Genet Biol 38 63 74
47. AM Calvo RA Wilson JW Bok NP Keller 2002 Relationship between secondary metabolism and fungal development Microbiol Mol Biol Rev 66 447 459
48. KC Ehrlich BG Montalbano JW Cary PJ Cotty 2002 Promoter elements in the aflatoxin pathway polyketide synthase gene Biochim. Biophys Acta 1576 171 175
49. KC Ehrlich PJ Cotty 2002 Variability in nitrogen regulation of aflatoxin production by Aspergillus flavus strains Appl Microbiol Biotechnol 60 174 178
50. JK Hicks J-H Yu NP Keller TH Adams 1997 Aspergillus sporulation and mycotoxin production both require inactivation of the FadA Gα protein-dependent signaling pathway EMBO J. 16 4916 4923
51. I Weiergang KV Wood LD Dunkle RL Nicholson 2004 In vivo growth and pathotoxin production by the maize pathogen Cochliobolus carbonum Physiol Mol Plant Pathol 64 273 279
52. S Nishimura RP Scheffer 1965 Interactions between Helminthosporium victoriae spores and oat tissue Phytopathology 55 629 634
53. JC Comstock CA Martinson 1975 Involvement of Helminthosporium maydis race T toxin during colonization of maize leaves Phytopathology 65 616 619
54. A Tag J Hicks G Garifullina CJ Ake TD Phillips M Beremand N Keller 2000 G-protein signalling mediates differential production of toxic secondary metabolites Mol Microbiol 38 658 665
55. G Shaner EL Stromberg GH Lacy KR Barker TP Pirone 1992 Nomenclature and concepts of pathogenicity and virulence Annu Rev Phytopathol 30 47 66
56. Youngman RJ, Elstner EF Photodynamic and reductive mechanisms of oxygen activation by the fungal phytotoxins, cercosporin and dothistromin. In: Bors W, Saran M, Tait D, eds. Oxygen Radicals in Chemistry and Biology, Walter de Gruyter and Co., Berlin, 1984: 501-508
57. AM Harvey RD Batt GG Pritchard 1976 Inhibition of RNA synthesis in Chlorella pyrenoidosa and Bacillus megaterium by the pine-blight toxin, dothistromin J Gen Microbiol 96 268 276
58. PJ Cotty 1994 Influence of field application of an atoxigenic strain of Aspergillus flavus on the populations of A. flavus infecting cotton bolls and on the aflatoxin content of cottonseed Phytopathology 84 1270 1277
59. JW Dorner RJ Cole DT Wicklow 1999 Aflatoxin reduction in corn through field application of competitive fungi J Food Prot 62 650 656
60. HH Wilkinson A Ramaswamy SC Sim NP Keller 2004 Increased conidiation associated with progression along the sterigmatocystin biosynthetic pathway Mycologia 96 1190 1198
61. S Malz MN Grell C Thrane FJ Maier P Rosager A Felk KS Albertsen S Salomon L Bohn W Schafer H Giese 2005 Identification of a gene cluster responsible for the biosynthesis of aurofusarin in the Fusarium graminearum species complex Fungal Genet Biol 42 420 433
62. Bradshaw RE, Jin H-P, Morgan BS, Schwelm A, Teddy OR, Young CA, Zhang SG. A polyketide synthase gene required for biosynthesis of the aflatoxin-like toxin, dothistromin. Mycopathologia 2006; 161: 283-294