Hymenosetin, a 3-decalinoyltetramic acid antibiotic from cultures of the ash dieback pathogen, Hymenoscyphus pseudoalbidus

Phytochemistry

Volumn 100, Issue , 2014, Pages 86-91

  Halecker, Sandra ^a   Surup, Frank ^a   Kuhnert, Eric ^a   Mohr, Kathrin I ^a   Brock, Nelson L ^b   Dickschat, Jeroen S ^b   Junker, Corina ^b,c   Schulz, Barbara ^b   Stadler, Marc ^a  

^a HELMHOLTZ CENTRE FOR INFECTION RESEARCH   (Germany)

^b TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

^c INSTITUTE FOR EPIDEMIOLOGY AND PATHOGEN DIAGNOSTICS   (Germany)

Author keywords

Ash dieback; Hymenoscyphus pseudoalbidus; MRSA; Natural products; Secondary metabolite; Structure elucidation; Tetramic acid

Indexed keywords

CHALARA; FRAXINUS; FRAXINUS EXCELSIOR; FUNGI; HYMENOSCYPHUS; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS;

2 PYRROLIDONE DERIVATIVE; ANTIINFECTIVE AGENT; HYMENOSETIN; TETRAMIC ACID;

ARTICLE; ASCOMYCETES; ASH DIEBACK; CHEMISTRY; CULTURE TECHNIQUE; GROWTH, DEVELOPMENT AND AGING; HYMENOSCYPHUS PSEUDOALBIDUS; ISOLATION AND PURIFICATION; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MICROBIAL SENSITIVITY TEST; NATURAL PRODUCTS; SECONDARY METABOLITE; STRUCTURE ELUCIDATION;

ASH DIEBACK; HYMENOSCYPHUS PSEUDOALBIDUS; MRSA; NATURAL PRODUCTS; SECONDARY METABOLITE; STRUCTURE ELUCIDATION; TETRAMIC ACID;

ANTI-BACTERIAL AGENTS; ASCOMYCOTA; CULTURE TECHNIQUES; MICROBIAL SENSITIVITY TESTS; PYRROLIDINONES;

EID: 84897656495     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2014.01.018     Document Type: Article

References (27)

1. P.F. Andersson, S.B.K. Johansson, J. Stenlid, and A. Broberg Isolation, identification and necrotic activity of viridiol from Chalara fraxinea, the fungus responsible for dieback of ash Forest Pathol. 40 2010 43 46
2. C. Bassarello, G. Bifulco, A. Evidente, R. Riccio, and L. Gomez-Paloma Stereochemical studies on ascaulitoxin: a J-based NMR configurational analysis of a nitrogen substituted system Tetrahedron Lett. 42 2001 8611 8613
3. J. Bitzer, T. Læssøe, J. Fournier, V. Kummer, C. Decock, H.-V. Tichy, M. Piepenbring, D. Peršoh, and M. Stadler Affinities of Phylacia and the daldinoid Xylariaceae, inferred from chemotypes of cultures and ribosomal DNA sequences Mycol. Res. 112 2008 251 270
4. C. Boros, A. Dix, B. Katz, Y. Vasina, and C. Pearce Isolation and identification of cissetin-a setin-like antibiotic with a novel cis-octalin ring fusion J. Antibiot. 56 2003 862 865
5. D. Boettger, and C. Hertweck Molecular diversity sculpted by fungal PKS-NRPS hybrids ChemBiochem 14 2013 28 42
6. H.R. Burmeister, G.A. Bennet, R.F. Vesonder, and C.W. Hesseltine Antibiotic produced by Fusarium equiseti NRRL 5537 Antimicrob. Agents Chemother. 5 1974 634 639
7. V. Hellwig, T. Grothe, A. Mayer-Bartschmid, R. Endermann, F.R. Geschke, T. Henkel, and M. Stadler Altersetin, a new antibiotic from cultures of endophytic Alternaria spp J. Antibiot. 55 2002 881 892
8. J. Inokoshi, N. Shigeta, T. Fukuda, R. Uchida, K. Nonaka, R. Masuma, and H. Tomoda Epi-trichosetin, a new undecaprenyl pyrophosphate synthase inhibitor, produced by Fusarium oxysporum FKI-4553 J. Antibiot. 66 2013 549 554
9. C. Junker, F. Mandey, A. Pais, R. Ebel, and B. Schulz Hymenoscyphus pseudoalbidus and Hymenoscyphus albidus: viridiol concentration and virulence do not correlate Forest Pathol. 44 2014 39 44
10. G. Lang, J.W. Blunt, N.J. Cummings, A.L.J. Cole, and M.H.G. Munro Paecilosetin, a new bioactive fungal metabolite from a New Zealand isolate of Paecilomyces farinosus J. Nat. Prod. 68 2005 810 811
11. E.C. Marfori, S. Kajiyama, E. Fukusaki, and A. Kobayashi Trichosetin, a novel tetramic acid antibiotic produced in dual culture of Trichoderma harzianum and Catharanthus roseus callus Z. Naturforsch. 57c 2002 465 470
12. E.C. Marfori, S. Kajiyama, E. Fukusaki, and A. Kobayashi Phytotoxicity of the tetramic acid metabolite trichosetin Phytochemistry 62 2003 715 721
13. N. Matsumori, D. Kaneno, M. Murata, H. Nakamura, and K. Tachibana Stereochemical determination of acyclic structures based on carbon-proton spin-coupling constants. A method of configuration analysis for natural products J. Org. Chem. 64 1999 866 876
14. J.S. Moffatt, J.D. Bu'Lock, and T.H. Yuen Viridiol, a steroid-like product from Trichoderma viride J. Chem. Soc. Chem. Commun. 1969 839
15. P.W. Okanya, K.I. Mohr, K. Gerth, R. Jansen, and R. Müller Marinoquinolines A-F, pyrroloquinolines from Ohtaekwangia kribbensis (Bacteroidetes) J. Nat. Prod. 74 2011 603 608
16. V. Queloz, C.R. Grünig, R. Berndt, T. Kowalski, T.N. Sieber, and O. Holdenrieder Cryptic speciation in Hymenoscyphus albidus Forest Pathol. 41 2011 133 142
17. B.J.L. Royles Naturally occurring tetramic acids: Structure, isolation, and synthesis Chem. Rev. 95 1995 1981 2001
18. R. Schobert, and A. Schlenk Tetramic and tetronic acids: an update on new derivatives and biological aspects Bioorg. Med. Chem. 16 2008 4203 4221
19. B. Schulz, S. Draeger, T.E. Dela Cruz, J. Rheinheimer, K. Siems, S. Loesgen, J. Bitzer, O. Schlörke, A. Zeeck, I. Kock, H. Hussain, J. Dai, and K. Krohn Screening strategies for obtaining novel, biologically active, fungal secondary metabolites from marine habitats Bot. Mar. 51 2008 219 234
20. M.P. Segeth, A. Bonnefoy, M. Brönstrup, M. Knauf, D. Schummer, L. Toti, L. Vértesy, M.-C. Wetzel-Raynal, J. Wink, and G. Seibert Coniosetin, a novel tetramic acid antibiotic from Coniochaeta ellipsoidea DSM 13856 J. Antibiot. 56 2003 114 122
21. M. Stadler, H.-V. Tichy, E. Katsiou, and V. Hellwig Chemotaxonomy of Pochonia and other conidial fungi with Verticillium-like anamorphs Mycol. Progr. 2 2003 95 122
22. S.B. Singh, D.L. Zink, M.A. Goetz, A.W. Dombrowski, J.D. Polishook, and D.J. Hazuda Equisetin and a novel opposite stereochemical homolog phomasetin, two fungal metabolites as inhibitors of HIV integrase Tetrahedron Lett. 39 1998 2243 2246
23. Y. Sugie, K.A. Dekker, T. Inagaki, Y.J. Kim, T. Sakakibara, S. Sakemi, A. Sugiura, L. Brennan, J. Duignan, J.A. Sutcliffe, and Y. Kojima A novel antibiotic CJ-17,572 from a fungus, Pezicula sp J. Antibiot. 55 2002 19 24
24. F. Surup, K.I. Mohr, R. Jansen, and M. Stadler Cohaerins G-K, azaphilone pigments from Annulohypoxylon cohaerens and absolute stereochemistry of cohaerins C-K Phytochemistry 95 2013 252 258
25. M.H. Wheeler, R.D. Stipanovic, and L.S. Puckhaber Phytotoxicity of equisetin and epi-equisetin isolated from Fusarium equiseti and F. pallidoroseum Mycol. Res. 103 1999 967 973
26. R.T. Williamson, I.P. Singh, and W.H. Gerwick Taveuniamides: new chlorinated toxins from a mixed assemblage of marine cyanobacteria Tetrahedron 60 2004 7025 7033
27. Y.J. Zhao, T. Hosoya, H.O. Baral, K. Hosaka, and M. Kakishima Hymenoscyphus pseudoalbidus, the correct name for Lambertella albida reported from Japan Mycotaxon 122 2012 25 41