Skip to main content
SpringerLink
Log in

Macrocarpones, novel metabolites from stromata of Hypoxylon macrocarpum, and new evidence on the chemotaxonomy of Hypoxylon species

  • Published:
Mycological Progress Aims and scope Submit manuscript

Abstract

Several species of the genus Hypoxylon (Xylariaceae) were studied for morphological characters and HPLC-based secondary metabolite profiles. It was confirmed that Hypoxylon is divided into two groups of species, containing either Mitorubrin type azaphilones or binaphthyls, respectively, as main metabolites. In Hypoxylon species of the latter group, some metabolites that are known from the allied genus Daldinia (i.e., Daldinal A in H. fuscum and Daldinin C in H. fuscopurpureum), were encountered for the first time. Moreover, three novel aromatic polyketides, for which the trivial names Macrocarpones A, B and C are proposed, were isolated from ascostromata of Hypoxylon macrocarpum and identified by high resolution mass spectrometry and 2D-NMR spectroscopy. Orsellinic Acid was also identified from ascostromata of H. howeianum and detected by HPLC-MS and HPLC-UV/Vis fingerprinting methodology in H. fragiforme and H. rubiginosum, but not in other examined Hypoxylon species. Due to these studies, H. fuscopurpureum sensu Y.-M. Ju & J.D. Rogers 1996 was identified as a new record for Germany.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • Casser I (1983) Isolierung und Strukturaufklärung von Farbstoffen aus holzbewohnenden Pilzen. Doctoral thesis. Univ. Bonn, Germany. 133 pp

    Google Scholar 

  • Gill M, Steglich W (1987) Pigments of fungi (Macromycetes). In Herz W, Grisebach H, Kirby GW, Tamm C (eds) Progress in the chemistry of organic natural products. vol. 51. Springer Verlag Berlin, Heidelberg, New York

    Google Scholar 

  • Granmo A (1999) Morphotaxonomy and chorology of the genus Hypoxylon (Xylariaceae) in Norway. — Sommerfeltia 26: 1–81

    Google Scholar 

  • Hesse, M, Meier H, Zeeh B (1991) Spektroskopische Methoden in der organischen Chemie, p.186 (Benzylmethylketon)

  • Igarashi M, Tetsuka Y, Mimura Y, Takahashi A, Tamamura T, Sato K (1993) AB5046A and B, novel chlorosis-inducing substances from Nodulisporium sp. — Journal of Antibiotics 46: 1843–1848

    CAS  PubMed  Google Scholar 

  • Jayaprakasha, GK, Rao, LJ (2000) Phenolic constituents from the lichen Parmotrema stuppeum (Nyl.)Hale and their antioxidant activity. — Zeitschrift für Naturforschung C (Journal of Biosciences) 55: 1018–1022

    CAS  Google Scholar 

  • Ju YM, Rogers JD (1996) A revision of the genus Hypoxylon. Mycologia Memoir no. 20. APS Press, St. Paul, MN., USA 365 pp

    Google Scholar 

  • Krieglsteiner GJ, Enderle M (1989) Über Vorkommen, Verbreitung und Ökologie einiger Arten der Gattungen Biscogniauxia O. Kuntze 1891, Nemania S.F. Gray 1821 emend. Pouzar 1986 und Hypoxylon Bulliard 1791 s. str. in der Bundesrepublik Deutschland und einigen Nachbarländern. — Mitteilungsblatt der AG Pilzkunde Niederrhein 7: 46–89

    Google Scholar 

  • Martin P (1968) Studies in the Xylariaceae: IV. Hypoxylon, sections Papillata and Annulata. — South African Journal of Botany 34: 303–330

    Google Scholar 

  • Mazzaglia H, Anselmi N, Vicario S, Vannini A (2001) Sequence analysis of the 5.8S rDNA and ITS region in evaluating genetic relationships among some species of Hypoxylon and related genera. — Mycological Research 105: 670–675

    Article  CAS  Google Scholar 

  • Miller JH (1961) A monograph of the world species of Hypoxylon. Univ. Georgia Press, Athens, Georgia, USA

    Google Scholar 

  • Ogasawara N, Kawai K (1998) Hydrogenated azaphilones from Emericella falconensis and E. fruticulosa. — Phytochemistry 47: 1131–1135

    Article  CAS  Google Scholar 

  • Petrini, LE, Müller E (1986) Haupt-und Nebenfruchtformen europäischer Hypoxylon-Arten (Xylariaceae, Sphaeriales) und verwandter Pilze. — Mycologia Helvetica 1: 501–627

    Google Scholar 

  • Petrini LE, Petrini O, Sieber TN (1987) Host specificity of Hypoxylon fuscum: A statistical approach to the problem. — Sydowia 40: 227–234

    Google Scholar 

  • Pouzar Z (1978) Hypoxylon macrocarpum Pouz. spec. nov., a new fragrant Pyrenomycete. — Ceská Mykologia 32: 19–21

    Google Scholar 

  • Rogers JD, Ju YM (1996) Entoleuca mammata comb. nov. for Hypoxylon mammatum and the genus Entoleuca. — Mycotaxon 59: 441–448

    Google Scholar 

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

    Google Scholar 

  • Rogers JD, Ju YM (1998) The genus Kretzschmaria. — Mycotaxon 68: 345–393

    Google Scholar 

  • Salvatore MJ, Hensens OD, Zink DL, Liesch J, Dufresne C, Ondeyka J, Jürgens TM, Borris RP, Raghoobar S, McCauley E, Kong L, Gartner SE, Koch G, Pelaéz F, Diez MT, Cascales C, Martin I, Polishook JD, Balick MJ, Beck HT, King SR, Hsu A, Lingham RB (1994) L-741,494, a fungal metabolite that is an inhibitor of interleukin-1β converting enzyme. — Journal of Natural Products 57: 755–760

    Article  CAS  PubMed  Google Scholar 

  • Sánchez-Ballesteros J, González V, Salazar O, Acero J, Portal MA, Julián, M, Rubio V, Bills GF, Polishook JD, Platas G, Mochales S, Peláez F (2000) Phylogenetic study of Hypoxylon and related genera based on ribosomal ITS sequences. — Mycologia 92: 964–977

    Google Scholar 

  • Schulz H, Albroscheit G (1989) Characterization of oakmoss products used in perfumery by high-performance liquid chromatography. — Journal of Chromatography 466: 301–306

    CAS  Google Scholar 

  • Stadler M, Baumgartner M, Wollweber H. (2001) Three new Daldinia species with yellow stromatal pigments. — Mycotaxon 80: 179–196

    Google Scholar 

  • 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

    Article  CAS  PubMed  Google Scholar 

  • Stadler M, Wollweber H, Baumgartner M, Ju YM and Rogers JD (2001b) Daldinia decipiens sp. nov. and notes on further Daldinia spp. inhabiting Betulaceae in Europe. — Mycotaxon 80: 167–176

    Google Scholar 

  • Stadler M, Wollweber H, Mühlbauer A, Asakawa Y, Hashimoto T, Rogers JD, Ju YM, Wetzstein HG, Tichy HV (2001c) Molecular chemotaxonomy of Daldinia and other Xylariaceae. — Mycological Research 109: 1191–1205

    Google Scholar 

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

    Google Scholar 

  • Suzuki S, Hosoe T, Nozawa K, Yaguchi T, Udagawa S, Kawai K (1999) Mitorubrin derivatives on ascomata of some Talaromyces species of ascomyceteous fungi. — Journal of Natural Products 62: 1329–1329

    Article  Google Scholar 

  • Turner, R. (1971) Fungal metabolites. Chapter 5. Polyketides. Academic Press London, New York

    Google Scholar 

  • Whalley AJS, Edwards RL (1995) Secondary metabolites and systematic arrangement within the Xylariaceae. — Canadian Journal of Botany 73Suppl. 1: S802–S810

    CAS  Google Scholar 

  • Wollweber H, Stadler M (2001) Zur Kenntnis der Gattung Daldinia in Deutschland und Europa. — Zeitschrift für Mykologie 67: 3–53

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Bayer AG, Pharma Research Europe, Life Science Center Natural Products, P.O.B. 101709, D-42096, Wuppertal, Germany

    Andrea Mühlbauer, Stephan Seip & Marc Stadler

  2. Department of Mycology, Botanische Staatsammlung München, Menzinger Str. 67, D-80638, München, Germany

    Dagmar Triebel

  3. Lehrstuhl für Pflanzensystematik, Universität Bayreuth, Universitätsstraße 30 — NW I, D-95440, Bayreuth

    Derek Persoh

  4. Naturwissenschaftlicher Verein Wuppertal, In den Birken 73, D-42113, Wuppertal

    Hartmund Wollweber & Marc Stadler

Authors
  1. Andrea Mühlbauer
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Dagmar Triebel
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Derek Persoh
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Hartmund Wollweber
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Stephan Seip
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Marc Stadler
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Marc Stadler.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Mühlbauer, A., Triebel, D., Persoh, D. et al. Macrocarpones, novel metabolites from stromata of Hypoxylon macrocarpum, and new evidence on the chemotaxonomy of Hypoxylon species. Mycol Progress 1, 235–248 (2002). https://doi.org/10.1007/s11557-006-0021-z

Download citation

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11557-006-0021-z

Keywords

Search

Navigation