Cytotoxic and antifungal activities of melleolide antibiotics follow dissimilar structure-activity relationships

Phytochemistry

Volumn 105, Issue , 2014, Pages 101-108

  Bohnert, Markus ^a   Nützmann, Hans Wilhelm ^b   Schroeckh, Volker ^b   Horn, Fabian ^b   Dahse, Hans Martin ^b   Brakhage, Axel A ^b   Hoffmeister, Dirk ^a  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^b HANS KNÖLL INSTITUTE   (Germany)

Author keywords

Armillaria mellea; Melleolide; Natural product characterization; Physalacriaceae; Sesquiterpene aryl ester; Structure activity relationship

Indexed keywords

ARMILLARIA; ARMILLARIA MELLEA; ASPERGILLUS FLAVUS; EMERICELLA NIDULANS; FUNGI; PENICILLIUM CHRYSOGENUM;

ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; ORSELLINIC ACID; RESORCINOL DERIVATIVE; SESQUITERPENE;

ARMILLARIA; ASPERGILLUS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; FUNGUS; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; ANTI-INFECTIVE AGENTS; ANTIFUNGAL AGENTS; ARMILLARIA; ASPERGILLUS; FUNGI; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; RESORCINOLS; SESQUITERPENES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84905496400     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2014.05.009     Document Type: Article

References (33)

1. W.R. Abraham Bioactive sesquiterpenes produced by fungi: are they useful for humans as well? Curr. Med. Chem. 8 2001 583 606
2. A. Arnone, R. Cardillo, and G. Nasini Secondary mold metabolites. 14. Structures of melleolides B-D, 3 antibacterial sesquiterpenoids from Armillaria mellea Phytochemistry 25 1986 471 474
3. A. Arnone, R. Cardillo, V. Di Modugno, and G. Nasini Secondary mold metabolites. 22. Isolation and structure elucidation of melledonals D and E and melleolides E-H, novel sesquiterpenoid aryl esters from Clitocybe elegans and Armillaria mellea Gazz. Chim. Ital. 118 1988 517 521
4. A. Arnone, R. Cardillo, and G. Nasini Secondary mold metabolites. 23. Isolation and structure elucidation of melleolides I and J and armellides A and B, novel sesquiterpenoid aryl esters from Armillaria novae-zelandiae Gazz. Chim. Ital. 118 1988 523 527
5. R.W. Barratt, G.B. Johnson, and W.N. Ogata Wild-type and mutant stocks of Aspergillus nidulans Genetics 52 1965 233 246
6. K. Baumgartner, M.P.A. Coetzee, and D. Hoffmeister Secrets of the subterranean pathosystem of Armillaria Mol. Plant Pathol. 12 2011 515 534
7. 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
8. J.W. Bok, D. Hoffmeister, L.A. Maggio-Hall, R. Murillo, J.D. Glasner, and N.P. Keller Genomic mining for Aspergillus natural products Chem. Biol. 13 2006 31 37 (Pubitemid 43099922)
9. S. Bouhired, M. Weber, A. Kempf-Sontag, N.P. Keller, and D. Hoffmeister Accurate prediction of the Aspergillus nidulans terrequinone gene cluster boundaries using the transcriptional regulator LaeA Fungal Genet. Biol. 44 2007 1134 1145 (Pubitemid 47532762)
10. P. Cremin, D.M.X. Donnelly, J.-L. Wolfender, and K. Hostettmann Liquid chromatographic-thermospray mass spectrometric analysis of sesquiterpenes of Armillaria (Eumycota: Basidiomycotina) species J. Chromatogr. A 710 1995 273 285
11. 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. Commun. 1982 135 137
12. D.M. Donnelly, F. Abe, D. Coveney, N. Fukuda, J. O'Reilly, J. Polonsky, and T. Prangé Antibacterial sesquiterpene aryl esters from Armillaria mellea J. Nat. Prod. 48 1985 10 16 (Pubitemid 15053336)
13. 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
14. R.D. Firn, and C.G. Jones Natural products - a simple model to explain chemical diversity Nat. Prod. Rep. 20 2003 382 391 (Pubitemid 37007962)
15. R.D. Firn, and C.G. Jones A Darwinian view of metabolism: molecular properties determine fitness J. Exp. Bot. 60 2009 719 726
16. J. Gerke, Ö. Bayram, K. Feussner, M. Landesfeind, E. Shelest, I. Feussner, and G.H. Braus Breaking the silence: protein stabilization uncovers silenced biosynthetic gene clusters in the fungus Aspergillus nidulans Appl. Environ. Microbiol. 78 2012 8234 8244
17. M. Isaka, N. Rugseree, P. Maithip, P. Kongsaeree, S. Prabpai, and Y. Thebtaranonth Hirsutellones A-E, antimycobacterial alkaloids from the insect pathogenic fungus Hirsutella nivea BCC 2594 Tetrahedron 61 2005 5577 5583 (Pubitemid 40712280)
18. G. Lackner, M. Bohnert, J. Wick, and D. Hoffmeister Assembly of melleolide antibiotics involves a polyketide synthase with cross-coupling activity Chem. Biol. 20 2013 1101 1106
19. S.L. Midland, R.R. Izac, R.M. Wing, A.I. Zaki, D.E. Munnecke, and J.J. Sims Melleolide, a new antibiotic from Armillaria mellea Tetrahedron Lett. 23 1982 2515 2518 (Pubitemid 12014735)
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. I. Momose, R. Sekizawa, N. Hosokawa, H. Iinuma, S. Matsui, H. Nakamura, H. Naganawa, M. Hamada, and T. Takeuchi Melleolides K, L and M, new melleolides from Armillariella mellea J. Antibiot. 53 2000 137 143 (Pubitemid 30135870)
23. National Committee for Clinical Laboratory Standards Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically, Approved Standard M7-A 1991 NCCLS Villanova, PA, USA
24. H.W. Nützmann, Y. Reyes-Dominguez, K. Scherlach, V. Schroeckh, F. Horn, A. Gacek, J. Schümann, C. Hertweck, J. Strauss, and A.A. Brakhage Bacteria-induced natural product formation in the fungus Aspergillus nidulans requires Saga/Ada-mediated histone acetylation Proc. Natl. Acad. Sci. U.S.A. 108 2011 14282 14287
25. T. Obuchi, H. Kondoh, N. Watanabe, M. Tamai, S. Omura, J.S. Yang, and X.T. Liang Armillaric acid, a new antibiotic produced by Armillaria mellea Planta Med. 56 1990 198 201 (Pubitemid 20168055)
26. 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
27. G. Pontecorvo, J.A. Roper, L.M. Hemmons, K.D. MacDonald, and A.W.J. Bufton The genetics of Aspergillus nidulans Adv. Genet. 5 1953 141 238
28. D. Ramón, L. Carramolino, C. Patiño, F. Sánchez, and M.A. Peñalva Cloning and characterization of the isopenicillin N synthetase gene mediating the formation of the beta-lactam ring in Aspergillus nidulans Gene 57 1987 171 181 (Pubitemid 18007105)
29. 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. U.S.A. 106 2009 14558 14563
30. B. Shen Polyketide biosynthesis beyond the type I, II and III polyketide synthase paradigms Curr. Opin. Chem. Biol. 7 2003 285 295 (Pubitemid 36514961)
31. K. Waisser, E. Petrlíková, M. Perina, V. Klimesová, J. Kunes, K. Palát Jr., J. Kaustová, H.M. Dahse, and U. Möllmann A note to the biological activity of benzoxazine derivatives containing the thioxo group Eur. J. Med. Chem. 45 2010 2719 2725
32. P. Wiemann, C.J. Guo, J.M. Palmer, R. Sekonyela, C.C. Wang, and N.P. Keller Prototype of an intertwined secondary-metabolite supercluster Proc. Natl. Acad. Sci. U.S.A. 110 2013 17065 17070
33. J.S. Yang, Y.W. Chen, X.Z. Feng, D.Q. Yu, and X.T. Liang Chemical constituents of Armillaria mellea mycelium. I. Isolation and characterization of armillarin and armillaridin Planta Med. 50 1984 288 290