Redirection of pigment biosynthesis to isocoumarins in Fusarium

Fungal Genetics and Biology

Volumn 49, Issue 8, 2012, Pages 613-618

  Sørensen, Jens Laurids ^a,b   Nielsen, Kristian Fog ^c   Sondergaard, Teis Esben ^a,b  

^a AARHUS UNIVERSITY   (Denmark)

^b AALBORG UNIVERSITY   (Denmark)

^c TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

Aurofusarin; Bikaverin; Bikisocoumarin; Citreoisocoumarin; Polyketide synthases; Secondary metabolites

Indexed keywords

AUROFUSARIN; BIKAVERIN; CITREOISOCOUMARIN; FUNGAL ENZYME; ISOCOUMARIN DERIVATIVE; POLYKETIDE SYNTHASE; PREBIKAVERIN; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; CONTROLLED STUDY; ENZYME ACTIVE SITE; ENZYME ANALYSIS; ENZYME STRUCTURE; ENZYME SYNTHESIS; FUNGAL STRAIN; FUNGUS GROWTH; FUSARIUM; FUSARIUM CULMORUM; FUSARIUM GRAMINEARUM; FUSARIUM OXYSPORUM; FUSARIUM PROLIFERATUM; FUSARIUM SPOROTRICHIOIDES; FUSARIUM VENENATUM; IONIZATION; MUTAGENESIS; NITROGEN AVAILABILITY; NITROGEN DYNAMICS; NONHUMAN; PH; PIGMENTATION; PRIORITY JOURNAL; PROTEIN DOMAIN;

FUSARIUM; HYDROGEN-ION CONCENTRATION; ISOCOUMARINS; NITROGEN; PIGMENTS, BIOLOGICAL; POLYKETIDE SYNTHASES;

FUNGI; FUSARIUM;

EID: 84864045240     PISSN: 10871845     EISSN: 10960937     Source Type: Journal    
DOI: 10.1016/j.fgb.2012.06.004     Document Type: Article

References (26)

1. Dao H.P., Mathieu F., Lebrihi A. Two primer pairs to detect OTA producers by PCR method. Int. J. Food Microbiol. 2005, 104:61-67.
2. Ellestad G.A., Lovell F.M., Perkinson N.A., Hargreaves R.T., Mcgahren W.J. New zearalenone related macrolides and isocoumarins from an unidentified fungus. J. Org. Chem. 1978, 43:2339-2343.
3. Frandsen R.J.N., Nielsen N.J., Maolanon N., Sørensen J.C., Olsson S., Nielsen J., Giese H. The biosynthetic pathway for aurofusarin in Fusarium graminearum reveals a close link between the naphthoquinones and naphthopyrones. Mol. Microbiol. 2006, 61:1069-1080.
4. Frandsen R.J.N., Schutt C., Lund B.W., Staerk D., Nielsen J., Olsson S., Giese H. Two novel classes of enzymes are required for the biosynthesis of aurofusarin in Fusarium graminearum. J. Biol. Chem. 2011, 286:10419-10428.
5. Fujii I., Watanabe A., Sankawa U., Ebizuka Y. Identification of Claisen cyclase domain in fungal polyketide synthase WA, a naphthopyrone synthase of Aspergillus nidulans. Chem. Biol. 2001, 8:189-197.
6. Gardiner D.M., Kazan K., Manners J.M. Nutrient profiling reveals potent inducers of trichothecene biosynthesis in Fusarium graminearum. Fungal Genet. Biol. 2009, 46:604-613.
7. Hansen F.T., Sørensen J.L., Sondergaard T.E., Giese H., Frandsen R.J.N. Quick guide to secondary metabolite genes in Fusarium. Int. J. Food Microbiol. 2012, 155:128-136.
8. Kim J.E., Han K.H., Jin H.M., Kim H., Kim J.C., Yun S.H., Lee Y.W. Putative polyketide synthase and laccase genes for biosynthesis of aurofusarin in Gibberella zeae. Appl. Environ. Microbiol. 2005, 71:1701-1708.
9. Lai S., Shizuri Y., Yamamura S., Kawai K., Furukawa H. 3 New phenolic metabolites from Penicillium species. Heterocycles 1991, 32:297-305.
10. Larsen T.O., Breinholt J. Dichlorodiaportin, diaportinol, and diaportinic acid: Three novel isocoumarins from Penicillium nalgiovense. J. Nat. Prod. 1999, 62:1182-1184.
11. Linnemannstöns P., Schulte J., Prado M.D., Proctor R.H., Avalos J., Tudzynski B. The polyketide synthase gene pks4 from Gibberella fujikuroi encodes a key enzyme in the blosynthesis of the red pigment bikaverin. Fungal Genet. Biol. 2002, 37:134-148.
12. Ma S.M., Zhan J.X., Xie X.K., Watanabe K.J., Tang Y., Zhang W.J. Redirecting the cyclization steps of fungal polyketide synthase. J. Am. Chem. Soc. 2008, 130:38-39.
13. Malmstrom J., Christophersen C., Frisvad J.C. Secondary metabolites characteristic of Penicillium citrinum, Penicillium steckii and related species. Phytochemistry 2000, 54:301-309.
14. Malz S., Grell M.N., Thrane C., Maier F.J., Rosager P., Felk A., et al. Identification of a gene cluster responsible for the biosynthesis of aurofusarin in the Fusarium graminearum species complex. Fungal Genet. Biol. 2005, 42:420-433.
15. Mayorga M.E., Timberlake W.E. The developmentally regulated Aspergillus nidulans wA gene encodes a polypeptide homologous to polyketide and fatty-acid synthases. Mol. Gen. Genet. 1992, 235:205-212.
16. Nielsen K.F., Sumarah M.W., Frisvad J.C., Miller J.D. Production of metabolites from the Penicillium roqueforti complex. J. Agric. Food Chem. 2006, 54:3756-3763.
17. Nielsen K.F., Mansson M., Rank C., Frisvad J.C., Larsen T.O. Dereplication of microbial natural products by LC-DAD-TOFMS. J. Nat. Prod. 2011, 74:2338-2348.
18. O'Callaghan J., Caddick M.X., Dobson A.D.W. A polyketide synthase gene required for ochratoxin A biosynthesis in Aspergillus ochraceus. Microbiology 2003, 149:3485-3491.
19. Smedsgaard J. Micro-scale extraction procedure for standardized screening of fungal metabolite production in cultures. J. Chromatogr. A 1997, 760:264-270.
20. Sørensen J.L., Phipps R.K., Nielsen K.F., Frank J., Schroers H.J., Thrane U. Analysis of Fusarium avenaceum metabolites produced during wet apple core rot. J. Agric. Food Chem. 2009, 57:1632-1639.
21. Sørensen J.L., Aveskamp M.M., Hansen M.E., Thrane U., Andersen B. Chemical characterization of Phoma pomorum isolated from Danish maize. Int. J. Food Microbiol. 2010, 136:310-317.
22. Sørensen J.L., Hansen F.T., Sondergaard T.E., Staerk D., Lee T.V., Wimmer R., et al. Production of novel fusarielins by ectopic activation of the polyketide synthase 9 cluster in Fusarium graminearum. Environ. Microbiol. 2012, 14:1159-1170.
23. Watanabe A., Ono Y., Fujii I., Sankawa U., Mayorga M.E., Timberlake W.E., Ebizuka Y. Product identification of polyketide synthase coded by Aspergillus nidulans wA gene. Tetrahedron Lett. 1998, 39:7733-7736.
24. Watanabe A., Fujii I., Sankawa U., Mayorga M.E., Timberlake W.E., Ebizuka Y. Re-identification of Aspergillus nidulans wA gene to code for a polyketide synthase of naphthopyrone. Tetrahedron Lett. 1999, 40:91-94.
25. Wiemann P., Willmann A., Straeten M., Kleigrewe K., Beyer M., Humpf H.U., Tudzynski B. Biosynthesis of the red pigment bikaverin in Fusarium fujikuroi: genes, their function and regulation. Mol. Microbiol. 2009, 72:931-946.
26. Yang S.X., Gao J.M., Zhang Q.A., Laatsch H. Toxic polyketides produced by Fusarium sp., an endophytic fungus isolated from Melia azedarach. Bioorg. Med. Chem. Lett. 2011, 21:1887-1889.