Assembly of melleolide antibiotics involves a polyketide synthase with cross-coupling activity

Chemistry and Biology

Volumn 20, Issue 9, 2013, Pages 1101-1106

  Lackner, Gerald ^a   Bohnert, Markus ^a   Wick, Jonas ^a   Hoffmeister, Dirk ^a  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; MELLEOLIDE; POLYKETIDE SYNTHASE; THIOL ESTER HYDROLASE; UNCLASSIFIED DRUG;

ARTICLE; ASCOMYCETES; BASIDIOMYCETES; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; IN VITRO STUDY; NONHUMAN; PHYLOGENY; PRIORITY JOURNAL;

ARMILLARIA; ARMILLARIA MELLEA; ASCOMYCOTA; BASIDIOMYCOTA;

ANTI-BACTERIAL AGENTS; ARMILLARIA; ESTERIFICATION; EVOLUTION, MOLECULAR; POLYKETIDE SYNTHASES; RESORCINOLS; SESQUITERPENES;

EID: 84884534993     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2013.07.009     Document Type: Article

References (32)

1. A. Arnone, R. Cardillo, and G. Nasini Isolation and structure elucidation of melleolide-I and melleolide-J and armellides A and B, novel sesquiterpenoid aryl esters from Armillaria novae-zelandiae Gazz. Chim. Ital. 118 1988 523 527
2. K. Baumgartner, M.P.A. Coetzee, and D. Hoffmeister Secrets of the subterranean pathosystem of Armillaria Mol. Plant Pathol. 12 2011 515 534
3. M. Bohnert, S. Miethbauer, H.M. Dahse, J. Ziemen, M. Nett, and D. Hoffmeister In vitro cytotoxicity of melleolide antibiotics: structural and mechanistic aspects Bioorg. Med. Chem. Lett. 21 2011 2003 2006
4. T. Bretschneider, G. Zocher, M. Unger, K. Scherlach, T. Stehle, and C. Hertweck A ketosynthase homolog uses malonyl units to form esters in cervimycin biosynthesis Nat. Chem. Biol. 8 2012 154 161
5. R.J. Cox Polyketides, proteins and genes in fungi: programmed nano-machines begin to reveal their secrets Org. Biomol. Chem. 5 2007 2010 2026
6. D. Donnelly, S. Sanada, J. O'Reilly, J. Polonsky, T. Prangé, and C. Pascard Isolation and structure (X-ray analysis) of the orsellinate of armillol, a new antibacterial metabolite from Armillaria mellea J. Chem. Soc., Chem. Comm. 1982 135 137
7. B. Engels, U. Heinig, T. Grothe, M. Stadler, and S. Jennewein Cloning and characterization of an Armillaria gallica cDNA encoding protoilludene synthase, which catalyzes the first committed step in the synthesis of antimicrobial melleolides J. Biol. Chem. 286 2011 6871 6878
8. I. Fujii, Y. Mori, A. Watanabe, Y. Kubo, G. Tsuji, and Y. Ebizuka Enzymatic synthesis of 1,3,6,8-tetrahydroxynaphthalene solely from malonyl coenzyme A by a fungal iterative type I polyketide synthase PKS1 Biochemistry 39 2000 8853 8858
9. I. Fujii, A. Watanabe, U. Sankawa, and Y. Ebizuka Identification of Claisen cyclase domain in fungal polyketide synthase WA, a naphthopyrone synthase of Aspergillus nidulans Chem. Biol. 8 2001 189 197
10. C. Hertweck The biosynthetic logic of polyketide diversity Angew. Chem. Int. Ed. Engl. 48 2009 4688 4716
11. D.H. Huson SplitsTree: analyzing and visualizing evolutionary data Bioinformatics 14 1998 68 73
12. K. Ishiuchi, T. Nakazawa, T. Ookuma, S. Sugimoto, M. Sato, Y. Tsunematsu, N. Ishikawa, H. Noguchi, K. Hotta, H. Moriya, and K. Watanabe Establishing a new methodology for genome mining and biosynthesis of polyketides and peptides through yeast molecular genetics ChemBioChem 13 2012 846 854
13. J. Kennedy, K. Auclair, S.G. Kendrew, C. Park, J.C. Vederas, and C.R. Hutchinson Modulation of polyketide synthase activity by accessory proteins during lovastatin biosynthesis Science 284 1999 1368 1372
14. S. Kurasawa, H. Naganawa, T. Takeuchi, and H. Umezawa The structure of Ms-3: a glyoxalase I inhibitor produced by a mushroom Agric. Biol. Chem. 39 1975 2009 2014
15. H.J. Kwon, W.C. Smith, A.J. Scharon, S.H. Hwang, M.J. Kurth, and B. Shen C-O bond formation by polyketide synthases Science 297 2002 1327 1330
16. G. Lackner, M. Misiek, J. Braesel, and D. Hoffmeister Genome mining reveals the evolutionary origin and biosynthetic potential of basidiomycete polyketide synthases Fungal Genet. Biol. 49 2012 996 1003
17. G.H. Li, L. Li, M. Duan, and K.Q. Zhang The chemical constituents of the fungus Stereum sp Chem. Biodivers. 3 2006 210 216
18. H.C. Lin, Y.H. Chooi, S. Dhingra, W. Xu, A.M. Calvo, and Y. Tang The fumagillin biosynthetic gene cluster in Aspergillus fumigatus encodes a cryptic terpene cyclase involved in the formation of β-trans-bergamotene J. Am. Chem. Soc. 135 2013 4616 4619
19. S.M. Ma, J. Zhan, K. Watanabe, X. Xie, W. Zhang, C.C. Wang, and Y. Tang Enzymatic synthesis of aromatic polyketides using PKS4 from Gibberella fujikuroi J. Am. Chem. Soc. 129 2007 10642 10643
20. M. Misiek, and D. Hoffmeister Sesquiterpene aryl ester natural products in North American Armillaria species Mycol. Prog. 11 2012 7 15
21. M. Misiek, J. Williams, K. Schmich, W. Hüttel, I. Merfort, C.E. Salomon, C.C. Aldrich, and D. Hoffmeister Structure and cytotoxicity of arnamial and related fungal sesquiterpene aryl esters J. Nat. Prod. 72 2009 1888 1891
22. H. Peipp, and J. Sonnenbichler Secondary fungal metabolites and their biological activities, II. Occurrence of antibiotic compounds in cultures of Armillaria ostoyae growing in the presence of an antagonistic fungus or host plant cells Biol. Chem. Hoppe Seyler 373 1992 675 683
23. J.F. Sanchez, Y.M. Chiang, E. Szewczyk, A.D. Davidson, M. Ahuja, C. Elizabeth Oakley, J. Woo Bok, N. Keller, B.R. Oakley, and C.C.C. Wang Molecular genetic analysis of the orsellinic acid/F9775 gene cluster of Aspergillus nidulans Mol. Biosyst. 6 2010 587 593
24. I. Schmitt, S. Kautz, and H.T. Lumbsch 6-MSAS-like polyketide synthase genes occur in lichenized ascomycetes Mycol. Res. 112 2008 289 296
25. V. Schroeckh, K. Scherlach, H.W. Nützmann, E. Shelest, W. Schmidt-Heck, J. Schuemann, K. Martin, C. Hertweck, and A.A. Brakhage Intimate bacterial-fungal interaction triggers biosynthesis of archetypal polyketides in Aspergillus nidulans Proc. Natl. Acad. Sci. USA 106 2009 14558 14563
26. J. Staunton, and K.J. Weissman Polyketide biosynthesis: a millennium review Nat. Prod. Rep. 18 2001 380 416
27. E. Stocker-Wörgötter Metabolic diversity of lichen-forming ascomycetous fungi: culturing, polyketide and shikimate metabolite production, and PKS genes Nat. Prod. Rep. 25 2008 188 200
28. K. Tamura, D. Peterson, N. Peterson, G. Stecher, M. Nei, and S. Kumar MEGA5: molecular evolutionary genetics analysis using maximum likelihood, evolutionary distance, and maximum parsimony methods Mol. Biol. Evol. 28 2011 2731 2739
29. A.L. Vagstad, E.A. Hill, J.W. Labonte, and C.A. Townsend Characterization of a fungal thioesterase having Claisen cyclase and deacetylase activities in melanin biosynthesis Chem. Biol. 19 2012 1525 1534
30. M. Wang, H. Zhou, M. Wirz, Y. Tang, and C.N. Boddy A thioesterase from an iterative fungal polyketide synthase shows macrocyclization and cross coupling activity and may play a role in controlling iterative cycling through product offloading Biochemistry 48 2009 6288 6290
31. H. Zhou, J. Zhan, K. Watanabe, X. Xie, and Y. Tang A polyketide macrolactone synthase from the filamentous fungus Gibberella zeae Proc. Natl. Acad. Sci. USA 105 2008 6249 6254
32. H. Zhou, K. Qiao, Z. Gao, J.C. Vederas, and Y. Tang Insights into radicicol biosynthesis via heterologous synthesis of intermediates and analogs J. Biol. Chem. 285 2010 41412 41421