Three new α-pyrone derivatives from the plant endophytic fungus Penicillium ochrochloronthe and their antibacterial, antifungal, and cytotoxic activities

J Asian Nat Prod Res. 2019 Sep;21(9):851-858. doi: 10.1080/10286020.2018.1495197. Epub 2018 Aug 21.

Abstract

Three new 3,4,6-trisubstituted α-pyrone derivatives, namely 6-(2'R-hydroxy-3'E,5'E-diene-1'-heptyl)-4-hydroxy-3-methyl-2H-pyran-2-one (1), 6-(2'S-hydroxy-5'E-ene-1'-heptyl)-4-hydroxy-3-methyl-2H-pyran-2-one (2), and 6-(2'S-hydroxy-1'-heptyl)-4 -hydroxy-3-methyl-2H-pyran-2-one (3), together with one known compound trichodermic acid (4), were isolated from the solid-substrate fermentation culture of Penicillium ochrochloronthe associated the roots of Taxus media. Compounds 1-4 displayed the antimicrobial activity selectively against tested fungal and bacterial strains with minimum inhibitory concentration (MIC) values ranging from 12.5 to 100 μg/ml. Furthermore, we found that only compound 4 exhibited moderate cytotoxicity against five human cancer cells (A549, LN229, MGC, LOVO, and MDA231) with IC50 values of 51.45, 23.43, 39.16, 46.97, and 42.85 μg/ml, respectively.

Keywords: Plant endophytic fungi; antimicrobial activity; cytotoxic activity; α-pyrone.

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Bacteria / drug effects
  • Cell Line, Tumor
  • Cell Survival
  • Fungi / drug effects
  • Humans
  • Molecular Structure
  • Penicillium / chemistry*
  • Pyrones / chemistry*

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Antineoplastic Agents
  • Pyrones