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Daldinia sacchari (Hypoxylaceae) from India produces the new cytochalasins Saccalasins A and B and belongs to the D. eschscholtzii species complex

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Abstract

Stromata of a Daldinia species were collected from half-burnt sugarcane stalks in South India. Based on a combination of morphological and chemotaxonomic evidence, the species was identified as the first recent record of Daldinia sacchari. While it was impossible to obtain cultures from the ascospores, the stromata were subjected to DNA extraction and DNA sequencing and secondary metabolites were analyzed by high-performance liquid chromatography coupled with diode array and mass spectrometric detection (HPLC-DAD/MS). The fruiting body extract was subjected to preparative HPLC for the isolation of secondary metabolites. Two new cytochalasins, for which we propose the trivial names saccalasins A and B, were elucidated besides two known cytochalasins and binaphthalene tetrol (BNT) by NMR spectroscopy and mass spectrometry. Whereas sequencing of housekeeping genes from the stromatal DNA unfortunately failed, an ITS DNA sequence was obtained from this species for the first time and compared to those of related Hypoxylaceae in a phylogenetic tree. The results indicate a close relationship of D. sacchari to the D. eschscholtzii complex, from which cytochalasins are also known as predominant stromatal metabolites. Phylogenetic analyses based on the ITS-rDNA barcode (which can only discriminate the Hypoxylaceae and other Sordariomycetes into species groups, rather than serve as a means of genus or species discrimination) confirmed that D. sacchari belongs to the D. eschscholtzii species complex. However, as with the majority of tropical Hypoxylaceae species, the availability of cultures that can be used to generate DNA sequence data that are more conclusive than ITS will be imperative to further narrow down the phylogenetic affinities of these fungi.

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References

  • 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

    Article  CAS  PubMed  Google Scholar 

  • Buchanan MS, Hashimoto T, Asakawa Y (1996) Cytochalasins from a Daldinia sp. of fungus. Phytochemistry 41(3):821–828

    Article  CAS  Google Scholar 

  • Chepkirui C, Matasyoh JC, Decock C, Stadler M (2017) Two cytotoxic triterpenes from cultures of a Kenyan Laetiporus sp. (Basidiomycota). Phytochem Lett 20:106–110

    Article  CAS  Google Scholar 

  • Child M (1932) The genus Daldinia. Ann Mo Bot Gard 19:429–496

    Article  Google Scholar 

  • Daranagama DA, Hyde KD, Sir EB, Thambugala KM, Tian Q, Samarakoon MC, McKenzie EHC, Jayasiri SC, Tibpromma S, Bhat JD, Liu X, Stadler M (2018) Towards a natural classification and backbone tree for Graphostromataceae, Hypoxylaceae, Lopadostomataceae and Xylariaceae. Fungal Divers 88:1–165

    Article  Google Scholar 

  • Davey ML (2010) Annellosporium nemorosum gen. et sp. nov., an annellidic anamorph with phylogenetic affinities to the genus Daldinia (Xylariales). Karstenia 50:1–10

    Article  Google Scholar 

  • Helaly SE, Thongbai B, Stadler M (2018) Diversity of biologically active secondary metabolites from endophytic and saprotrophic fungi of the ascomycete order Xylariales. Nat Prod Rep, in press (https://doi.org/10.1039/c8np00010g)

  • Hsieh HM, Ju YM, Rogers JD (2005) Molecular phylogeny of Hypoxylon and closely related genera. Mycologia 97:844–865

    Article  CAS  PubMed  Google Scholar 

  • Johannesson H, Laessøe T, Stenlid J (2000) Molecular and morphological investigation of the genus Daldinia in Northern Europe. Mycol Res 104:275–280

    Article  CAS  Google Scholar 

  • Ju YM, Rogers JD, San Martín F (1997) A revision of the genus Daldinia. Mycotaxon 61:243–293

    Google Scholar 

  • Kuhnert E, Sir EB, Lambert C, Hyde KD, Hladki AI, Romero AI, Rohde M, Stadler M (2017) Phylogenetic and chemotaxonomic resolution of the genus Annulohypoxylon (Xylariaceae) including four new species. Fungal Divers 85(1):–43

  • Nylander, J.A.A (2004) MrModeltest v2. Program distributed by the author. Evolutionary Biology Centre, Uppsala University

  • 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

    Article  Google Scholar 

  • Rayner RW (1970) A mycological colour chart. Commonwealth Mycological Institute Kew and British Mycological Society

  • Richter C, Helaly SE, Thongbai B, Hyde KD, Stadler M (2016) Pyristriatins A and B: Pyridino-cyathane antibiotics from the basidiomycete Cyathus cf. striatus. J Nat Prod 79:1684–1688

    Article  CAS  PubMed  Google Scholar 

  • Ronquist F, Huelsenbeck JP (2003) MrBayes 3: Bayesian phylogenetic inference under mixed models. Bioinformatics 19:1572–1574

    Article  CAS  Google Scholar 

  • Sandargo B, Thongbai B, Stadler M, Surup F (2018) Cysteine-derived pleurotin congeners from the nematode-trapping basidiomycete Hohenbuehelia grisea. J Nat Prod 81:286–291

    Article  CAS  PubMed  Google Scholar 

  • Skellam E (2017) The biosynthesis of cytochalasans. Nat Prod Rep 34(11):1252–1263

    Article  CAS  PubMed  Google Scholar 

  • Sir EB, Lambert C, Wendt L, Hladki A, Romero A, Stadler M (2017) A new species of Daldinia (Xylariaceae) from the argentine subtropical montane forest. Mycosphere 7(9):1378–1388

    Article  Google Scholar 

  • Sir EB, Kuhnert E, Lambert C, Hladki AI, Romero AI, Stadler M (2016) New species and reports of Hypoxylon from Argentina recognized by a polyphasic approach. Mycol Prog 15:42

    Article  Google Scholar 

  • Stadler M, Wollweber H, Mühlbauer A, Henkel T, Asakawa Y, Hashimoto T, Rogers JD, Ju YM, Wetzstein HG, Tichy HV (2001) Secondary metabolite profiles, genetic fingerprints and taxonomy of Daldinia and allies. Mycotaxon 77:379–429

    Google Scholar 

  • Stadler M, Hellwig V (2005) Chemotaxonomy of the Xylariaceae and remarkable bioactive compounds from Xylariales and their associated asexual stages. Recent Res Dev Phytochem 9:1–53

    Google Scholar 

  • Stadler M, Quang DN, Tomita A, Hashimoto T, Asakawa Y (2006) Production of bioactive metabolites during stromatal ontogeny of Hypoxylon fragiforme. Mycol Res 110:811–820

    Article  CAS  PubMed  Google Scholar 

  • Stadler M, Fournier J, Læssøe T, Lechat C, Tichy HV, Piepenbring M (2008) Recognition of hypoxyloid and xylarioid Entonaema species from a comparison of holomorphic morphology, HPLC profiles, and ribosomal DNA sequences. Mycol Prog 7:53–73

    Article  Google Scholar 

  • 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

    Article  PubMed  PubMed Central  Google Scholar 

  • 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

    Article  Google Scholar 

  • Vasilyeva L, Stadler M (2008) Pyrenomycetes of the Russian Far East 3. Three new Daldinia species (Xylariaceae). Mycotaxon 104:284–296

    Google Scholar 

  • Van der Gucht K (1994) The Xylariaceae of Papua New Guinea. Ph.D. dissertation. Univ. Gent

  • Wang J, Wang Z, Ju Z, Wan J, Liao S, Lin X, Liu Y (2015) Cytotoxic cytochalasins from marine-derived fungus Arthrinium arundinis. Planta Med 81:160–166

    Article  CAS  PubMed  Google Scholar 

  • Wendt L, Sir EB, Kuhnert E, Heitkämper S, Lambert C, Hladki AI, Romero AI, Luangsa-ard JJ, Srikitikulchai P, Peršoh D, Stadler M (2018) Resurrection and emendation of the Hypoxylaceae, recognised from a multi-gene genealogy of the Xylariales. Mycol Prog 17:115–154

    Article  Google Scholar 

  • White TJ, Bruns T, Lee S, Taylor JW (1990) Amplification and direct sequencing of fungal ribosomal RNA genes for phylogenetics. In: Innis MA, Gelfand DH, Sninsky JJ, White TJ (eds) PCR protocols: A guide to methods and applications. Academic Press, Inc, New York, pp 315–322

    Google Scholar 

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Acknowledgements

Expert technical assistance by Cäcilia Bergmann is gratefully acknowledged. The Ministry of Science, Research and Technology (MSRT) of Iran is also gratefully acknowledged for the financial support. Furthermore, we are grateful to various colleagues at the HZI: Kathrin I. Mohr and Wera Collisi for conducting the bioassays and Christel Kakoschke for recording NMR spectra.

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Correspondence to Marc Stadler.

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Section Editor: Hans-Josef Schroers and Marc Stadler

This article is part of the Special Issue in honor of Prof. Walter Gams

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Narmani, A., Pichai, S., Palani, P. et al. Daldinia sacchari (Hypoxylaceae) from India produces the new cytochalasins Saccalasins A and B and belongs to the D. eschscholtzii species complex. Mycol Progress 18, 175–185 (2019). https://doi.org/10.1007/s11557-018-1413-6

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