New Benzaldehyde and Benzopyran Compounds from the Endophytic Fungus Paraphaeosphaeria sp. F03 and Their Antimicrobial and Cytotoxic Activities

Planta Med. 2019 Aug;85(11-12):957-964. doi: 10.1055/a-0853-7793. Epub 2019 Feb 19.

Abstract

Three new benzaldehyde derivatives, sporulosaldeins A - C (1: -3: ), and 3 new benzopyran derivatives, sporulosaldeins D - F (4: -6: ), were discovered from an endophytic fungus, Paraphaeosphaeria sp. F03, which was isolated from Paepalanthus planifolius leaves. Compounds 1: -6: were elucidated by 1- and 2-dimensional nuclear magnetic resonance experiments and high-resolution mass spectrometry analysis. The absolute configuration of compound 5: was determined through the comparison of experimental and calculated electronic circular dichroism data. Compounds 1: -6: were found to exhibit antifungal activity with minimum inhibitory concentration (MIC) values of 7.8 - 250 µg/mL and racemic mixture of compound 6: exhibited weak cytotoxicity against MCF-7 and LM3 with IC50 values of 34.4 and 39.2 µM, respectively.

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification
  • Antifungal Agents / pharmacology*
  • Ascomycota / chemistry*
  • Benzaldehydes / chemistry
  • Benzaldehydes / isolation & purification
  • Benzaldehydes / pharmacology*
  • Benzopyrans / chemistry
  • Benzopyrans / isolation & purification
  • Benzopyrans / pharmacology*
  • Cell Line, Tumor
  • Cytotoxins / chemistry
  • Cytotoxins / isolation & purification
  • Cytotoxins / pharmacology*
  • Endophytes
  • Humans
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Mice
  • Microbial Sensitivity Tests
  • Molecular Structure

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Benzaldehydes
  • Benzopyrans
  • Cytotoxins