Acetophenone derivatives from a freshwater fungal isolate of recently described Lindgomyces madisonensis (G416)

Phytochemistry

Volumn 126, Issue , 2016, Pages 59-65

  Paguigan, Noemi D ^a   Raja, Huzefa A ^a   Day, Cynthia S ^b   Oberlies, Nicholas H ^a  

^a UNIVERSITY OF NORTH CAROLINA AT GREENSBORO   (United States)

^b WAKE FOREST UNIVERSITY   (United States)

Author keywords

Acetophenones; Freshwater ascomycetes; Lindgomyces madisonensis; Submerged wood

Indexed keywords

ACETOPHENONE; ACETOPHENONE DERIVATIVE; FRESH WATER;

ASCOMYCETES; ASPERGILLUS NIGER; CANDIDA ALBICANS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DRUG EFFECTS; ESCHERICHIA COLI; FUNGUS SPORE; ISOLATION AND PURIFICATION; MICROBIAL SENSITIVITY TEST; MICROBIOLOGY; MYCOBACTERIUM SMEGMATIS; NORTH CAROLINA; NUCLEAR MAGNETIC RESONANCE; PHYLOGENY; STAPHYLOCOCCUS AUREUS; WOOD; X RAY CRYSTALLOGRAPHY;

ACETOPHENONES; ASCOMYCOTA; ASPERGILLUS NIGER; CANDIDA ALBICANS; CRYSTALLOGRAPHY, X-RAY; ESCHERICHIA COLI; FRESH WATER; MICROBIAL SENSITIVITY TESTS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; MYCOBACTERIUM SMEGMATIS; NORTH CAROLINA; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PHYLOGENY; SPORES, FUNGAL; STAPHYLOCOCCUS AUREUS; WOOD;

EID: 84960532998     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2016.03.007     Document Type: Article

References (40)

1. A. Aly, A. Debbab, and P. Proksch Fifty years of drug discovery from fungi Fungal Divers 50 2011 3 19
2. S. Ayers, B.M. Ehrmann, A.F. Adcock, D.J. Kroll, E.J. Carcache de Blanco, Q. Shen, S.M. Swanson, J.O. Falkinham 3rd, M.C. Wani, S.M. Mitchell, C.J. Pearce, and N.H. Oberlies Peptaibols from two unidentified fungi of the order Hypocreales with cytotoxic, antibiotic, and anthelmintic activities J. Pept. Sci. 18 2012 500 510
3. M. Blackwell The fungi: 1, 2, 3... 5.1 million species? Am. J. Bot. 98 2011 426 438
4. P.W. Crous, M.J. Wingfield, J.J. Le Roux, D.M. Richardson, D. Strasberg, R.G. Shivas, P. Alvarado, J. Edwards, G. Moreno, R. Sharma, M.S. Sonawane, Y.P. Tan, A. Altés, B. Barasubiye, C.W. Barnes, R.A. Blanchette, D. Boertmann, A. Bogo, J.R. Carlavilla, R. Cheewangkoon, R. Daniel, Z.W. de Beer, M. de Jesús Yáñez-Morales, T.A. Duong, J. Fernández-Vicente, A.D.W. Geering, D.I. Guest, B.W. Held, M. Heykoop, V. Hubka, A.M. Ismail, S. Kajale, W. Khemmuk, M. Kolařík, R. Kurli, R. Lebeuf, C.A. Lévesque, L. Lombard, D. Magista, J.L. Manjón, S. Marincowitz, J.M. Mohedano, A. Nováková, N.H. Oberlies, E.C. Otto, N.D. Paguigan, I.G. Pascoe, J.L. Pérez-Butrón, G. Perrone, P. Rahi, H.A. Raja, T. Rintoul, R.M.V. Sanhueza, K. Scarlett, Y.S. Shouche, L.A. Shuttleworth, P.W.J. Taylor, R.G. Thorn, L.L. Vawdrey, R.S. Vidal, A. Voitk, P.T.W. Wong, A.R. Wood, J.C. Zamora, and J.Z. Groenewald Fungal planet description sheets: 371-399 Persoonia 35 2015 264 327
5. L. Du, J.B. King, B.H. Morrow, J.K. Shen, A.N. Miller, and R.H. Cichewicz Diarylcyclopentendione metabolite obtained from a Preussia typharum isolate procured using an unconventional cultivation approach J. Nat. Prod. 75 2012 1819 1823
6. T. El-Elimat, H.A. Raja, C.S. Day, W.L. Chen, S.M. Swanson, and N.H. Oberlies Greensporones: resorcylic acid lactones from an aquatic Halenospora sp J. Nat. Prod. 77 2014 2088 2098
7. T. El-Elimat, H.A. Raja, M. Figueroa, J.O. Falkinham 3rd, and N.H. Oberlies Isochromenones, isobenzofuranone, and tetrahydronaphthalenes produced by Paraphoma radicina, a fungus isolated from a freshwater habitat Phytochemistry 104 2014 114 120
8. M. Figueroa, A.K. Jarmusch, H.A. Raja, T. El-Elimat, J.S. Kavanaugh, A.R. Horswill, R.G. Cooks, N.B. Cech, and N.H. Oberlies Polyhydroxyanthraquinones as quorum sensing inhibitors from the guttates of Penicillium restrictum and their analysis by desorption electrospray ionization mass spectrometry J. Nat. Prod. 77 2014 1351 1358
9. M. Gareis, and E.-M. Gareis Guttation droplets of Penicillium nordicum and Penicillium verrucosum contain high concentrations of the mycotoxins ochratoxin A and B Mycopathologia 163 2007 207 214
10. T.A. Geissman, and E. Hinreiner Chromones. II. The synthesis of visnaginone J. Am. Chem. Soc. 73 1951 782 786
11. B. Hernández-Carlos, and M.M. Gamboa-Angulo Metabolites from freshwater aquatic microalgae and fungi as potential natural pesticides Phytochem. Rev. 10 2011 261 286
12. K. Hirayama, K. Tanaka, H.A. Raja, A.N. Miller, and C.A. Shearer A molecular phylogenetic assessment of Massarina ingoldiana sensu lato Mycologia 102 2010 729 746
13. T. Hosoe, J.B. Gloer, D.T. Wicklow, H.A. Raja, and C.A. Shearer New nonadride analogues from a freshwater isolate of an undescribed fungus belonging to the order pleosporales Heterocycles 81 2010 2123 2130
14. P. Jiao, D.C. Swenson, J.B. Gloer, J. Campbell, and C.A. Shearer Decaspirones A-E, bioactive spirodioxynaphthalenes from the freshwater aquatic fungus Decaisnella thyridioides J. Nat. Prod. 69 2006 1667 1671
15. A. Kaur, H.A. Raja, B.A. Darveaux, W.L. Chen, S.M. Swanson, C.J. Pearce, and N.H. Oberlies New diketopiperazine dimer from a filamentous fungal isolate of Aspergillus sydowii Magn. Reson. Chem. 53 2015 616 619
16. C. Li, M.V. Nitka, J.B. Gloer, J. Campbell, and C.A. Shearer Annularins A-H: new polyketide metabolites from the freshwater aquatic fungus Annulatascus triseptatus J. Nat. Prod. 66 2003 1302 1306
17. S.V. Mudur, D.C. Swenson, J.B. Gloer, J. Campbell, and C.A. Shearer Heliconols A-C: antimicrobial hemiketals from the freshwater aquatic fungus Helicodendron giganteum Org. Lett. 8 2006 3191 3194
18. H. Oh, T.O. Kwon, J.B. Gloer, L. Marvanova, and C.A. Shearer Tenellic acids A-D: new bioactive diphenyl ether derivatives from the aquatic fungus Dendrospora tenella J. Nat. Prod. 62 1999 580 583
19. H.A. Raja, T. El-Elimat, N.H. Oberlies, C.A. Shearer, K. Tanaka, A. Hoshimoto, and J. Fournier Minutisphaerales (Dothideomycetes, Ascomycota): a new order of freshwater ascomycetes including a new family, Minutisphaeraceae, and two new species from North Carolina, USA Mycologia 107 2015 845 862
20. H.A. Raja, N.H. Oberlies, T. El-Elimat, A.N. Miller, S.E. Zelski, and C.A. Shearer Lindgomyces angustiascus, (Lindgomycetaceae, Pleosporales, Dothideomycetes), a new lignicolous species from freshwater habitats in the USA Mycoscience 54 2013 353 361
21. H.A. Raja, N.H. Oberlies, M. Figueroa, K. Tanaka, K. Hirayama, A. Hashimoto, A.N. Miller, S.E. Zelski, and C.A. Shearer Freshwater ascomycetes: Minutisphaera (Dothideomycetes) revisited, including one new species from Japan Mycologia 105 2013 959 976
22. H.A. Raja, K. Tanaka, K. Hirayama, A.N. Miller, and C.A. Shearer Freshwater ascomycetes: two new species of Lindgomyces (Lindgomycetaceae, Pleosporales, Dothideomycetes) from Japan and USA Mycologia 103 2011 1421 1432
23. R.F. Reategui, J.B. Gloer, J. Campbell, and C.A. Shearer Ophiocerins A-D and ophioceric acid: tetrahydropyran derivatives and an africane sesquiterpenoid from the freshwater aquatic fungus Ophioceras venezuelense J. Nat. Prod. 68 2005 701 705
24. S.A. Rehner, and G.J. Samuels Molecular systematics of the Hypocreales: a teleomorph gene phylogeny and the status of their anamorphs Can. J. Bot. 73 1995 816 823
25. C.L. Schoch, K.A. Seifert, S. Huhndorf, V. Robert, J.L. Spouge, C.A. Levesque, and W. Chen Nuclear ribosomal internal transcribed spacer (ITS) region as a universal DNA barcode marker for fungi Proc. Natl. Acad. Sci. U.S.A. 109 2012 6241 6246
26. C.A. Shearer The freshwater Ascomycetes Nova Hedwigia 56 1993 1 33
27. C.A. Shearer The Distribution of Freshwater Filamentous Ascomycetes 2001 Science Publishers Plymouth, UK 225 292
28. C.A. Shearer Fungal biodiversity in aquatic habitats Biodivers. Conserv. 16 2007 49 67
29. C.A. Shearer, D.M. Langsam, and J.E. Longcore Fungi in freshwater habitats G.M. Mueller, G.F. Bills, M.S. Foster, Measuring and Monitoring Biological Diversity: Standard Methods for Fungi 2004 Smithsonian Institution Press Washington, D.C. 513 531
30. C.A. Shearer, and H.A. Raja Freshwater Ascomycetes Database 2015 < http://fungi.life.illinois.edu/ > (Accessed on April 4, 2015)
31. V.P. Sica, H.A. Raja, T. El-Elimat, V. Kertesz, G.J. Van Berkel, C.J. Pearce, and N.H. Oberlies Dereplicating and spatial mapping of secondary metabolites from fungal cultures in situ J. Nat. Prod. 78 2015 1926 1936
32. V.P. Sica, H.A. Raja, T. El-Elimat, and N.H. Oberlies Mass spectrometry imaging of secondary metabolites directly on fungal cultures RSC Adv. 4 2014 63221 63227
33. K.M. Vandermolen, H.A. Raja, T. El-Elimat, and N.H. Oberlies Evaluation of culture media for the production of secondary metabolites in a natural products screening program AMB Exp. 3 2013 71
34. R. Vilgalys, and M. Hester Rapid genetic identification and mapping of enzymatically amplified ribosomal DNA from several Cryptococcus species J. Bacteriol. 172 1990 4238 4246
35. X. Wang, J.G. Sena Filho, A.R. Hoover, J.B. King, T.K. Ellis, D.R. Powell, and R.H. Cichewicz Chemical epigenetics alters the secondary metabolite composition of guttate excreted by an atlantic-forest-soil-derived Penicillium citreonigrum J. Nat. Prod. 73 2010 942 948
36. T.J. White, T. Bruns, S. Lee, and J. Taylor Amplification and direct sequencing of fungal ribosomal RNA genes for phylogenetics M. Innis, D. Gelfand, J. Shinsky, T. White, PCR Protocols: A Guide to Methods and Applications 1990 Academic Press 315 322
37. A.A. Williams, E.W. Sugandhi, R.V. Macri, J.O. Falkinham 3rd, and R.D. Gandour Antimicrobial activity of long-chain, water-soluble, dendritic tricarboxylato amphiphiles J. Antimicrob. Chemother. 59 2007 451 458
38. R.C.R. Wootton Synthetic Approaches to Polyoxygenated Chromone and Chromanone Natural Products (Doctoral dissertation) 2000 School of Computing, Science and Engineering. University of Salford UK p. 222
39. B. Wu, J. Wiese, A. Labes, A. Kramer, R. Schmaljohann, and J.F. Imhoff Lindgomycin, an unusual antibiotic polyketide from a marine fungus of the Lindgomycetaceae Mar. Drugs 13 2015 4617 4632
40. Y. Zhang, X. Zhang, J. Fournier, J. Chen, and K.D. Hyde Lindgomyces griseosporus, a new aquatic ascomycete from Europe including new records Mycoscience 55 2014 43 48