Azaphilone pigments and macrodiolides from the coprophilous fungus Coniella fragariae

Fitoterapia. 2019 Sep:137:104249. doi: 10.1016/j.fitote.2019.104249. Epub 2019 Jun 25.

Abstract

Two azaphilone pigments (1 and 2), two dihydrobenzofurans (3 and 4), two macrodiolides (5 and 6), and a dimeric alkyl aromatic constituent (7) were isolated from the goose dung-derived fungus Coniella fragariae. Compounds 1-3 proved to be new natural products. Coniellins H and I (1 and 2) feature a tetracyclic core and an aldehyde group at C-5, which is unusual for azaphilone derivatives. The X-ray structure of pyrenophorin (5) is reported for the first time. Pyrenophorin (5) showed strong cytotoxicity against several cancer cell lines with IC50 values ranging from 0.07 to 7.8 μM.

Keywords: Azaphilones; Coniella fragariae; Cytotoxicity; Pyrenophorin.

MeSH terms

  • Animals
  • Ascomycota / chemistry*
  • Benzofurans / isolation & purification
  • Benzopyrans / isolation & purification
  • Benzopyrans / pharmacology*
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Feces / microbiology
  • Geese / microbiology
  • Germany
  • Humans
  • Molecular Structure
  • North Sea
  • Pigments, Biological / isolation & purification
  • Pigments, Biological / pharmacology*

Substances

  • Benzofurans
  • Benzopyrans
  • Pigments, Biological
  • azaphilone