Lenormandins A—G, new azaphilones from Hypoxylon lenormandii and Hypoxylon jaklitschii sp. nov., recognised by chemotaxonomic data

Fungal Diversity

Volumn 71, Issue 1, 2015, Pages 165-184

  Kuhnert, Eric ^a   Surup, Frank ^a   Sir, Esteban B ^b,c   Lambert, Christopher ^a   Hyde, Kevin D ^d   Hladki, Adriana I ^b   Romero, Andrea I ^c,e   Stadler, Marc ^a  

^a HELMHOLTZ CENTRE FOR INFECTION RESEARCH   (Germany)

^b FUNDACIÓN MIGUEL LILLO   (Argentina)

^c Fundación Miguel Lillo Institute of Mycology ^*  (Argentina)

^d MAE FAH LUANG UNIVERSITY   (Thailand)

^e UNIVERSIDAD DE BUENOS AIRES   (Argentina)

Author keywords

Chemotaxonomy; Hypoxylon; Phylogeny; Secondary metabolites; Systematics; Xylariaceae

Indexed keywords

FUNGI; HYPOXYLON; HYPOXYLON LENORMANDII; XYLARIACEAE;

EID: 84926380713     PISSN: 15602745     EISSN: 18789129     Source Type: Journal    
DOI: 10.1007/s13225-014-0318-1     Document Type: Article

References (49)

1. Bitzer J, Köpcke B, Stadler M, Hellwig V, Ju YM, Seip S, Henkel T (2007) Accelerated dereplication of natural products, supported by reference libraries. Chimia 51:332–338
2. Bitzer J, Læssøe T, Fournier J, Kummer V, Decock C, Tichy HV, Piepenbring M, Peršoh D, Stadler M (2008) Affinities of Phylacia and the daldinoid Xylariaceae, inferred from chemotypes of cultures and ribosomal DNA sequences. Mycol Res 112:251–270
3. Clark RC, Lee SY, Boger DL (2008) Total synthesis of chlorofusin, its seven chromophore diastereomers, and key partial structures. J Am Chem Soc 130:12355–12369
4. 13C NMR spectroscopy. Chem Phys Lipids 97:155–165
5. Dennis RWG (1963) Hypoxyloideae of Congo. Bull Jardin Bot Brux 33:317–343
6. Fournier J, Köpcke B, Stadler M (2010) New species of Hypoxylon from Western Europe and Ethiopia. Mycotaxon 113:209–235
7. Gao JM, Yang SX, Qin JC (2013) Azaphilones: chemistry and biology. Chem Rev 113:4755–4811
8. Halecker S, Surup F, Kuhnert E, Mohr KI, Brock NL, Dickschat JS, Junker C, Schulz B, Stadler M (2014) Hymenosetin, a 3-decalinoyltetramic acid antibiotic from cultures of the ash dieback pathogen, Hymenoscyphus pseudoalbidus. Phytochemistry, 100:86–91
9. Hashimoto T, Tahara S, Takaoka S, Tori M, Asakawa Y (1994) Structures of daldinins A~C, three novel azaphilone derivatives from ascomyceteous fungus Daldinia concentrica. Chem Pharm Bull 42:2397–2399
10. Hellwig V, Ju YM, Rogers JD, Fournier J, Stadler M (2005) Hypomiltin, a novel azaphilone from Hypoxylon hypomiltum, and chemotypes in Hypoxylon sect. Hypoxylon as inferred from analytical HPLC profiling. Mycol Progr 4:39–54
11. Hladki AI, Romero IA (2009) Taxonomic and nomenclatural aspects of Hypoxylon taxa from southern South America proposed by Spegazzini. Mycologia 101:733–744
12. Hsieh HM, Ju YM, Rogers JD (2005) Molecular phylogeny of Hypoxylon and closely related genera. Mycologia 97:844–865
13. Hsieh HM, Lin CR, Fang MJ, Rogers JD, Fournier J, Lechat C, Ju YM. (2010) Phylogenetic status of Xylaria subgenus Pseudoxylaria among taxa of the subfamily Xylarioideae (Xylariaceae) and phylogeny of the taxa involved in the subfamily. Mol Phylogenet Evol 54:957–969
14. Ju YM, Rogers JD (1996) A revision of the genus Hypoxylon. Mycologia Memoir no. 20. APS Press, St. Paul, 365 pp
15. Kuhnert E, Fournier J, Peršoh D, Luangsa-ard JJ, Stadler M (2014a) New Hypoxylon species from Martinique and new evidence on the molecular phylogeny of Hypoxylon based on ITS rDNA and β-tubulin data. Fungal Divers 64:181–203
16. Kuhnert E, Heitkämper S, Fournier J, Surup F, Stadler M (2014b) Hypoxyvermelhotins A–C, new pigments from Hypoxylon lechatii sp. nov. Fungal Biol 118:242–252
17. Læssøe T, Srikitikulchai P, Luangsa-ard JJD, Stadler M (2013) Theissenia reconsidered, including molecular phylogeny of the type species T. pyrenocrata and a new genus Durotheca (Xylariaceae, Ascomycota). IMA Fungus 4:57–69
18. Læssøe T, Srikitikulchai P, Fournier J, Köpcke B, Stadler M (2010) Lepraric acid derivatives as chemotaxonomic markers in Hypoxylon aeruginosum, Chlorostroma subcubisporum and C. cyaninum, sp. nov. Fungal Biol 114:481–489
19. Martin P (1969) Studies in the Xylariaceae. Part V. Euhypoxylon. J South Afr Bot 35:149–206
20. Mühlbauer A, Triebel D, Peršoh D, Wollweber H, Seip S, Stadler M (2002) Macrocarpones, novel metabolites from stromata of Hypoxylon macrocarpum and new evidence on the chemotaxonomy of Hypoxylon. Mycol Prog 1:235–248
21. Okanya PW, Mohr KI, Gerth K, Jansen R, Müller R (2011) Marinoquinolines A - F, pyrroloquinolines from Ohtaekwangia kribbensis (Bacteroidetes). J Nat Prod 74:603–608
22. Pažoutová S, Follert S, Bitzer J, Keck M, Surup F, Šrůtka P, Holuša J, Stadler M (2013) A new endophytic insect-associated Daldinia species, recognised from a comparison of secondary metabolite profiles and molecular phylogeny. Fungal Divers 60:107–123
23. Quang DN, Hashimoto T, Tanaka M, Baumgartner M, Stadler M, Asakawa Y (2002) Chemical constituents of the ascomycete Daldinia concentrica. J Nat Prod 65:1869–1874
24. Quang DN, Hashimoto T, Stadler M, Asakawa Y (2004a) New azaphilones from the inedible mushroom Hypoxylon rubiginosum. J Nat Prod 67:1152–1155
25. Quang DN, Hashimoto T, Tanaka M, Stadler M, Asakawa Y (2004b) Cyclic azaphilones daldinins E and F from the ascomycete fungus Hypoxylon fuscum (Xylariaceae). Phytochemistry 65:469–473
26. Quang DN, Hashimoto T, Fournier J, Stadler M, Radulović N, Asakawa Y (2005a) Sassafrins A–D, new antimicrobial azaphilones from the fungus Creosphaeria sassafras. Tetrahedron 61:1743–1748
27. Quang DN, Hashimoto T, Nomura Y, Wollweber H, Hellwig V, Fournier J, Stadler M, Asakawa Y (2005b) Cohaerins A and B, azaphilones from the fungus Hypoxylon cohaerens, and comparison of HPLC-based metabolite profiles in Hypoxylon sect. Annulata. Phytochemistry 66:797–809
28. Quang DN, Stadler M, Fournier J, Asakawa Y (2006a) Carneic acids A and B, two chemotaxonomically significant antimicrobial agents from the xylariaceous ascomycete, Hypoxylon carneum. J Nat Prod 69:1198–1202
29. Quang DN, Stadler M, Fournier J, Tomita A, Hashimoto T (2006b) Cohaerins C–F, four azaphilones from the xylariaceous fungus Annulohypoxylon cohaerens. Tetrahedron 62:6349–6354
30. Rayner RW (1970) A mycological colour chart. Commonwealth Mycological Institute, Kew and British Mycological Society
31. San Martin F, Rogers JD, Lavin P, Perez-Silva E, Esqueda M (1999) Two new species of Hypoxylon from Mexico. Mycotaxon 72:159–162
32. Sánchez-Ballesteros J, González V, Salazar O, Acero J, Portal MA, Julián M, Rubio V (2000) Phylogenetic study of Hypoxylon and related genera based on ribosomal ITS sequences. Mycologia 92:964–977
33. Stadler M, Fournier J (2006) Pigment chemistry, taxonomy and phylogeny of the Hypoxyloideae (Xylariaceae). Rev Iberoam Micol 23:160–170
34. Stadler M, Hellwig V (2005) Chemotaxonomy of the Xylariaceae and remarkable bioactive compounds from Xylariales and their associated asexual stages. Recent Res Dev Phytochem 9:41–93
35. Stadler M, Fournier J, Gardt S, Peršoh D (2010) The phylogenetic position of Rhopalostroma as inferred from a polythetic approach. Persoonia 25:11–21
36. Stadler M, Baumgartner M, Grothe T, Mühlbauer A, Seip S, Wollweber H (2001a) Concentricol, a taxonomically significant triterpenoid from Daldinia concentrica. Phytochemistry 56:787–793
37. Stadler M, Wollweber H, Mühlbauer A, Henkel T, Asakawa Y, Hashimoto T, Rogers JD, Ju YM, Wetzstein HG, Tichy HV (2001b) Secondary metabolite profiles, genetic fingerprints and taxonomy of Daldinia and allies. Mycotaxon 77:379–429
38. Stadler M, Fournier J, Quang DN, Akulov AY (2007) Metabolomic studies on the chemical ecology of the Xylariaceae (Ascomycota). Nat Prod Commun 2:287–304
39. Stadler M, Kuhnert E, Peršoh D, Fournier J (2013) The Xylariaceae as model example for a unified nomenclature following the “One Fungus-One Name” (1F1N) Concept. Mycol Int J Fungal Biol 4:5–21
40. Stadler M, Læssøe T, Fournier J, Decock C, Schmieschek B, Tichy HV, Peršoh D (2014) A polyphasic taxonomy of Daldinia (Xylariaceae). Stud Mycol 77:1–143
41. Stamatakis A (2006) RAxML-VI-HPC: maximum likelihood-based phylogenetic analyses with thousands of taxa and mixed models. Bioinformatics 22:2688–2690
42. Steglich W, Klaar M, Furtner W (1974) Mitorubrin derivatives from Hypoxylon fragiforme. Phytochemistry 13:2874–2875
43. Steyn PS, Vleggaar R (1976) The structure of dihydrodeoxy-8-epi-austdiol and the absolute configuration of the azaphilones. J Chem Soc Perkin Trans, pp 204–206
44. Surup F, Mohr KI, Jansen R, Stadler M (2013) Cohaerins G-K, azaphilone pigments from Annulohypoxylon cohaerens and absolute stereochemistry of cohaerins C–K. Phytochemistry 95:252–258
45. Suwannasai N, Rodtong, S,Thienhirun S, Whalley AJS (2006) New species and phylogenetic relationships of Hypoxylon species found in Thailand inferred from the internal transcribed spacer regions of ribosomal DNA sequences. Mycotaxon 94:303–324
46. Triebel D, Peršoh D, Wollweber H, Stadler M (2005) Phylogenetic relationships among Daldinia, Entonaema and Hypoxylon as inferred from ITS nrDNA sequences. Nova Hedw 80:25–43
47. Van der Gucht K (1995) Illustrations and descriptions of xylariaceous fungi collected in Papua New Guinea. Bull Jard Bot Brux 64:219–403
48. Whalley WB, Ferguson G, Marsh WC, Restivo RJ (1976) The chemistry of fungi. Part LXVIII. The absolute configuration of (+)-sclerotiorin and of the azaphilones. Journal of the Chemical Society. Perkin Trans, pp 1366–1369
49. Yamakoshi S, Hayashi N, Suzuki T, Nakada M (2009) Asymmetric total synthesis of (+)-carneic acid A and structure revision of its natural form. Tetrahedron Lett 50:5372–5375