Diversity of exophillic acid derivatives in strains of an endophytic Exophiala sp.

Phytochemistry

Volumn 118, Issue , 2015, Pages 83-93

  Cheikh Ali, Zakaria ^a   Glynou, Kyriaki ^a   Ali, Tahir ^b   Ploch, Sebastian ^b,d   Kaiser, Marcel ^c   Thines, Marco ^a,b   Bode, Helge B ^a   Maciá Vicente, Jose G ^a  

^a GOETHE UNIVERSITY   (Germany)

^b BIODIVERSITY AND CLIMATE RESEARCH CENTRE BIK F   (Germany)

^c SWISS TROPICAL AND PUBLIC HEALTH INSTITUTE   (Switzerland)

^d HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

Endophytes; Exophiala sp.; Exophillic acid; Fungi; Microthlaspi perfoliatum; Secondary metabolites

Indexed keywords

BENZOIC ACID DERIVATIVE; EXOPHILLIC ACID; GALACTOSIDE;

CHEMICAL STRUCTURE; CHEMISTRY; ENDOPHYTE; EXOPHIALA; FUNGUS; GENETICS; ISOLATION AND PURIFICATION; METABOLISM; NUCLEAR MAGNETIC RESONANCE; PLANT ROOT;

BENZOATES; ENDOPHYTES; EXOPHIALA; FUNGI; GALACTOSIDES; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLANT ROOTS;

EID: 84942980565     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2015.08.006     Document Type: Article

References (60)

1. H.D. Addy, M.M. Piercey, and R.S. Currah Microfungal endophytes in roots Can. J. Bot. 83 2005 1 13
2. S.F. Altschul, W. Gish, W. Miller, E.W. Myers, and D.J. Lipman Basic local alignment search tool J. Mol. Biol. 215 1990 403 410
3. S.T. Bates, G.S.N. Reddy, and F. Garcia-Pichel Exophiala crusticola anam. nov. (affinity Herpotrichiellaceae), a novel black yeast from biological soil crusts in the Western United States Int. J. Syst. Evol. Microbiol. 56 2006 2697 2702
4. H.B. Bode, M.W. Ring, G. Schwär, R.M. Kroppenstedt, D. Kaiser, and R. Müller 3-Hydroxy-3-methylglutaryl-coenzyme A (CoA) synthase is involved in biosynthesis of isovaleryl-CoA in the myxobacterium Myxococcus xanthus during fruiting body formation J. Bacteriol. 188 2006 6524 6528
5. A.A. Brakhage, and V. Schroeckh Fungal secondary metabolites - strategies to activate silent gene clusters Fungal Genet. Biol. 48 2011 15 22 (special issue: fungal secondary metabolism)
6. P. Bukovská, M. Jelínková, H. Hršelová, Z. Sýkorová, and M. Gryndler Terminal restriction fragment length measurement errors are affected mainly by fragment length, G + C nucleotide content and secondary structure melting point J. Microbiol. Methods 82 2010 223 228 10.1016/j.mimet.2010.06.007
7. J.W. Carmichael Cerebral mycetoma of trout due to a Phialophora-like fungus Sabouraudia 5 1966 120 123
8. J. Castresana Selection of conserved blocks from multiple alignments for their use in phylogenetic analysis Mol. Biol. Evol. 17 2000 540 552
9. Z. Cheikh-Ali, T. Okpekon, F. Roblot, C. Bories, M. Cardao, J.-C. Jullian, E. Poupon, and P. Champy Labdane diterpenoids from Aframomum sceptrum: NMR study and antiparasitic activities Phytochem. Lett. 4 2011 240 244
10. G.S. de Hoog, A.H.G.G. van den Ende, J.M.J. Uijthof, and W.A. Untereiner Nutritional physiology of type isolates of currently accepted species of Exophiala and Phaeococcomyces Antonie van Leeuwenhoek 68 1995 43 49
11. G.S. De Hoog, V.A. Vicente, M.J. Najafzadeh, M.J. Harrak, H. Badali, and S. Seyedmousavi Waterborne Exophiala species causing disease in cold-blooded animals PERSOONIA Mol. Phylogeny Evol. Fungi 27 2011 46 72
12. J. Doshida, H. Hasegawa, H. Onuki, and N. Shimidzu Exophilin A, a new antibiotic from a marine microorganism Exophiala pisciphila J. Antibiot. 49 1996 1105 1109
13. E.M. Fox, and B.J. Howlett Secondary metabolism: regulation and role in fungal biology Curr. Opin. Microbiol. 11 2008 481 487 (growth and development: eukaryotes/prokaryotes)
14. G.W. Francis, and K. Veland Alkylthiolation for the determination of double-bond positions in linear alkenes J. Chromatogr. A 219 1987 379 384
15. J.C. Frisvad, B. Andersen, and U. Thrane The use of secondary metabolite profiling in chemotaxonomy of filamentous fungi Mycol. Res. 112 2008 231 240
16. N. Funa, T. Awakawa, and S. Horinouchi Pentaketide resorcylic acid synthesis by type III polyketide synthase from Neurospora crassa J. Biol. Chem. 282 2007 14476 14481
17. F. Grundmann, M. Kaiser, M. Schiell, A. Batzer, M. Kurz, A. Thanwisai, N. Chantratita, and H.B. Bode Antiparasitic chaiyaphumines from entomopathogenic Xenorhabdus sp. PB61.4 J. Nat. Prod. 77 2014 779 783
18. G. Haase, L. Sonntag, B. Melzer-Krick, and G.S. De Hoog Phylogenetic inference by SSU gene analysis of members of the Herpotrichiellaceae, with special reference to human pathogenic species Stud. Mycol. 1999 80 97
19. K. Hamano, M. Kinoshita-Okami, K. Minagawa, H. Haruyama, T. Kinoshita, T. Hosoya, K. Furuya, K. Kinoshita, K. Tabata, A. Hemmi, and et al. Aquastatin A, an inhibitor of mammalian adenosine triphosphatases from Fusarium aquaeductuum. Taxonomy, fermentation, isolation, structure determination and biological properties J. Antibiot. 46 1993 1648 1657
20. S.J. Higginbotham, A.E. Arnold, A. Ibañez, C. Spadafora, P.D. Coley, and T.A. Kursar Bioactivity of fungal endophytes as a function of endophyte taxonomy and the taxonomy and distribution of their host plants PLoS One 8 2013 e73192
21. D.A. Hogan Talking to themselves: autoregulation and quorum sensing in fungi Eukaryot. Cell 5 2006 613 619
22. P.R. Hsueh, L.J. Teng, J.H. Hsu, Y.S. Liaw, Y.C. Chen, Y.S. Pan, H.J. Pan, P.C. Yang, S.W. Ho, and K.T. Luh Nosocomial Exophiala jeanselmei pseudoinfection after sonography-guided aspiration of thoracic lesions J. Formos. Med. Assoc. 100 2001 613 619
23. T. Julou, B. Burghardt, G. Gebauer, D. Berveiller, C. Damesin, and M.-A. Selosse Mixotrophy in orchids: insights from a comparative study of green individuals and nonphotosynthetic individuals of Cephalanthera damasonium New Phytol. 166 2005 639 653 10.1111/j.1469-8137.2005.01364.x
24. K. Katoh, and D.M. Standley MAFFT multiple sequence alignment software version 7: improvements in performance and usability Mol. Biol. Evol. 30 2013 772 780
25. J. Keim, B. Mishra, R. Sharma, S. Ploch, and M. Thines Root-associated fungi of Arabidopsis thaliana and Microthlaspi perfoliatum Fungal Divers. 66 2014 99 111
26. A.L. Khan, M. Hamayun, M. Waqas, S.-M. Kang, Y.-H. Kim, D.-H. Kim, and I.-J. Lee Exophiala sp. LHL08 association gives heat stress tolerance by avoiding oxidative damage to cucumber plants Biol. Fertil. Soils 48 2011 519 529
27. B.L.J. Kindler, H.-J. Krämer, S. Nies, P. Gradicsky, G. Haase, P. Mayser, M. Spiteller, and P. Spiteller Generation of indole alkaloids in the human-pathogenic fungus Exophiala dermatitidis Eur. J. Org. Chem. 2010 2010 2084 2090
28. S. Kusari, C. Hertweck, and M. Spiteller Chemical ecology of endophytic fungi: origins of secondary metabolites Chem. Biol. 19 2012 792 798
29. Y.-J. Kwon, Y. Fang, G.-H. Xu, and W.-G. Kim Aquastatin A, a new inhibitor of enoyl-acyl carrier protein reductase from Sporothrix sp. FN611 Biol. Pharm. Bull. 32 2009 2061 2064
30. F. Li, K. Li, X. Li, and B. Wang Chemical constituents of marine algal-derived endophytic fungus Exophiala oligosperma EN-21 Chin. J. Oceanol. Limnol. 29 2011 63 67
31. T. Li, M.J. Liu, X.T. Zhang, H.B. Zhang, T. Sha, and Z.W. Zhao Improved tolerance of maize (Zea mays L.) to heavy metals by colonization of a dark septate endophyte (DSE) Exophiala pisciphila Sci. Total Environ. 409 2011 1069 1074
32. J.G. Maciá-Vicente, V. Ferraro, S. Burruano, and L.V. Lopez-Llorca Fungal assemblages associated with roots of halophytic and non-halophytic plant species vary differentially along a salinity gradient Microb. Ecol. 64 2012 668 679
33. M.R. McGinnis, and L. Ajello A new species of Exophiala isolated from channel catfish Mycologia 66 1974 518 520
34. E. Müller, O. Petrini, P.J. Fisher, G.J. Samuels, and A.Y. Rossman Taxonomy and anamorphs of the Herpotrichiellaceae with notes on generic synonymy Trans. Br. Mycol. Soc. 88 1987 63 74
35. S. Nakanishi, K. Ando, I. Kawamoto, and H. Kase KS-501 and KS-502, new inhibitors of Ca2+ and calmodulin-dependent cyclic-nucleotide phosphodiesterase from Sporothrix sp J. Antibiot. 42 1989 1049 1055
36. Y. Ogura-Tsujita, and T. Yukawa Epipactis helleborine shows strong mycorrhizal preference towards ectomycorrhizal fungi with contrasting geographic distributions in Japan Mycorrhiza 18 2008 331 338
37. J.G. Ondeyka, D.L. Zink, A.W. Dombrowski, J.D. Polishook, P.J. Felock, D.J. Hazuda, and S.B. Singh Isolation, structure and HIV-1 integrase inhibitory activity of exophillic acid, a novel fungal metabolite from Exophiala pisciphila J. Antibiot. 56 2003 1018 1023
38. E. Paradis, J. Claude, and K. Strimmer APE: analyses of phylogenetics and evolution in R language Bioinformatics 20 2004 289 290
39. P.A. Paranagama, E.K. Wijeratne, and A.L. Gunatilaka Uncovering biosynthetic potential of plant-associated fungi: effect of culture conditions on metabolite production by Paraphaeosphaeria quadriseptata and Chaetomium chiversii J. Nat. Prod. 70 2007 1939 1945
40. F. Peláez, J. Collado, F. Arenal, A. Basilio, A. Cabello, M.T. Díez Matas, J.B. García, A. González, V. González, J. Gorrochategui, P. Hernández, I. Martín, G. Platas, and F. Vicente Endophytic fungi from plants living on gypsum soils as a source of secondary metabolites with antimicrobial activity Mycol. Res. 102 1998 755 761
41. V. Queloz, T.N. Sieber, O. Holdenrieder, B.A. McDonald, and C.R. Grünig No biogeographical pattern for a root-associated fungal species complex Glob. Ecol. Biogeogr. 20 2011 160 169
42. R Core Team R: A Language and Environment for Statistical Computing 2013 R Foundation for Statistical Computing Vienna, Austria
43. E.R. Rene, P. Bernat, J. Dlugonski, M.C. Veiga, and C. Kennes Use of styrene as sole carbon source by the fungus Exophiala oligosperma: optimization and modeling of biodegradation, pathway elucidation, and cell membrane composition Appl. Biochem. Biotechnol. 168 2012 1351 1357
44. 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. 106 2009 14558 14563
45. B. Schulz, C. Boyle, S. Draeger, A.-K. Römmert, and K. Krohn Endophytic fungi: a source of novel biologically active secondary metabolites Mycol. Res. 106 2002 996 1004
46. M. Stadler, and V. Hellwig Chemotaxonomy of the Xylariaceae and remarkable bioactive compounds from Xylariales and their associated asexual stages S.G. Pandalai, Recent Research and Developments in Phytochemistry 2005 Research Signpost Trivandrum 41 93
47. M. Stadler, H.-V. Tichy, E. Katsiou, and V. Hellwig Chemotaxonomy of Pochonia and other conidial fungi with Verticillium-like anamorphs Mycol. Prog. 2 2003 95 122
48. A. Stamatakis RAxML-VI-HPC: maximum likelihood-based phylogenetic analyses with thousands of taxa and mixed models Bioinformatics 22 2006 2688 2690
49. K. Sterflinger Black yeasts and meristematic fungi: ecology, diversity and identification D.G. Péter, P.C. Rosa, Biodiversity and Ecophysiology of Yeasts, the Yeast Handbook 2006 Springer Berlin Heidelberg 501 514
50. T. Těšitelová, J. Jersáková, M. Roy, B. Kubátová, J. Těšitel, T. Urfus, P. Trávníček, and J. Suda Ploidy-specific symbiotic interactions: divergence of mycorrhizal fungi between cytotypes of the Gymnadenia conopsea group (Orchidaceae) New Phytol. 199 2013 1022 1033
51. W.A. Untereiner Fruiting studies in species of Capronia (Herpotrichiellaceae) Antonie van Leeuwenhoek 68 1995 3 17
52. W.A. Untereiner, and F.A. Naveau Molecular systematics of the Herpotrichiellaceae with an assessment of the phylogenetic positions of Exophiala dermatitidis and Phialophora americana Mycologia 91 1999 67 83
53. M. Waki, H. Abe, and M. Inouye Translation of mutarotation into induced circular dichroism signals through helix inversion of host polymers Angew. Chem. 119 2007 3119 3121
54. C.-C. Wang, H.-Z. Liu, M. Liu, Y.-Y. Zhang, T.-T. Li, and X.-K. Lin Cytotoxic metabolites from the soil-derived fungus Exophiala pisciphila Molecules 16 2011 2796 2801
55. S. Wang, S. Zhang, T. Zhou, and J. Zhan Three new resorcylic acid derivatives from Sporotrichum laxum Bioorg. Med. Chem. Lett. 23 2013 5806 5809
56. T. Yasuzawa, Y. Saitoh, and H. Sano Structures of KS-501 and KS-502, the new inhibitors of Ca2+ and calmodulin-dependent cyclic nucleotide phosphodiesterase J. Antibiot. 43 1990 336 343
57. J.S. Zeng, and G.S. de Hoog Exophiala spinifera and its allies: diagnostics from morphology to DNA barcoding Med. Mycol. 46 2008 193 208
58. D. Zhang, X. Yang, J.S. Kang, H.D. Choi, and B.W. Son Chlorohydroaspyrones A and B, antibacterial aspyrone derivatives from the marine-derived fungus Exophiala sp. J. Nat. Prod. 71 2008 1458 1460
59. 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. 105 2008 6249 6254
60. K. Zhou, X. Zhang, F. Zhang, and Z. Li Phylogenetically diverse cultivable fungal community and polyketide synthase (PKS), non-ribosomal peptide synthase (NRPS) genes associated with the South China Sea sponges Microb. Ecol. 62 2011 644 654