Biologically active metabolites produced by the basidiomycete Quambalaria cyanescens

PLoS One. 2015 Feb 27;10(2):e0118913. doi: 10.1371/journal.pone.0118913. eCollection 2015.

Abstract

Four strains of the fungus Quambalaria cyanescens (Basidiomycota: Microstromatales), were used for the determination of secondary metabolites production and their antimicrobial and biological activities. A new naphthoquinone named quambalarine A, (S)-(+)-3-(5-ethyl-tetrahydrofuran-2-yliden)-5,7,8-trihydroxy-2-oxo-1,4-naphthoquinone (1), together with two known naphthoquinones, 3-hexanoyl-2,5,7,8-tetrahydroxy-1,4-naphthoquinone (named here as quambalarine B, 2) and mompain, 2,5,7,8-tetrahydroxy-1,4-naphthoquinone (3) were isolated. Their structures were determined by single-crystal X-ray diffraction crystallography, NMR and MS spectrometry. Quambalarine A (1) had a broad antifungal and antibacterial activity and is able inhibit growth of human pathogenic fungus Aspergillus fumigatus and fungi co-occurring with Q. cyanescens in bark beetle galleries including insect pathogenic species Beauveria bassiana. Quambalarine B (2) was active against several fungi and mompain mainly against bacteria. The biological activity against human-derived cell lines was selective towards mitochondria (2 and 3); after long-term incubation with 2, mitochondria were undetectable using a mitochondrial probe. A similar effect on mitochondria was observed also for environmental competitors of Q. cyanescens from the genus Geosmithia.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / isolation & purification
  • Anti-Infective Agents / metabolism
  • Anti-Infective Agents / pharmacology
  • Basidiomycota / metabolism*
  • Biological Products / chemistry
  • Biological Products / isolation & purification
  • Biological Products / metabolism*
  • Biological Products / pharmacology
  • Cell Line
  • Fermentation*
  • Humans
  • Microbial Sensitivity Tests

Substances

  • Anti-Infective Agents
  • Biological Products

Grant support

This study was supported by the Czech Science Foundation, project No. 13-16565S, www.gacr.cz/, JC MF ES MKo MC BP PN; European Regional Development Fund BIOCEV CZ.1.05/1.1.00/02.0109, www.biocev.eu, JC, MF, MKo, PN, PM; Operational Programme “Prague”—Competitiveness project CZ.2.16/3.1.00/24023, www.prahafondy.eu/cz/oppk.html, PM, PN, MKu. The funders had no role in study design, data collection and analysis, decision to publish, or preparation of the manuscript.