Antibacterial Diphenyl Ether, Benzophenone and Xanthone Derivatives from Aspergillus flavipes

Chem Biodivers. 2020 Feb;17(2):e1900640. doi: 10.1002/cbdv.201900640. Epub 2020 Jan 14.

Abstract

The extract of the strain Aspergillus flavipes DL-11 exerted antibacterial activities against six Gram-positive bacteria. During the following bioassay-guided separation, ten diphenyl ethers (1-10), two benzophenones (11-12), together with two xanthones (13-14) were isolated. Among them, 4'-chloroasterric acid (1) was a new chlorinated diphenyl ether. Their structures were elucidated by extensive spectroscopic data analysis, including IR, HR-ESI-MS, NMR experiments, and by comparison with the literature data. All compounds showed moderate to strong antibacterial effects on different Gram-positive bacteria with MIC values that ranged from 3.13 to 50 μg/mL, but none of the compounds exhibited activity against Gram-negative bacteria Vibrio parahaemolyticus ATCC17802 (MIC>100 μg/mL). In particular, the MICs of some compounds are at the level of positive control.

Keywords: Aspergillus flavipes; antibacterial activity; benzophenone; biological activity; diphenyl ether; xanthone.

MeSH terms

  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology
  • Aspergillus / chemistry*
  • Aspergillus / metabolism
  • Benzophenones / chemistry*
  • Benzophenones / isolation & purification
  • Benzophenones / pharmacology
  • Gram-Negative Bacteria / drug effects
  • Gram-Positive Bacteria / drug effects
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Phenyl Ethers / chemistry*
  • Phenyl Ethers / isolation & purification
  • Phenyl Ethers / pharmacology
  • Xanthones / chemistry*
  • Xanthones / isolation & purification
  • Xanthones / pharmacology

Substances

  • Anti-Bacterial Agents
  • Benzophenones
  • Phenyl Ethers
  • Xanthones
  • phenyl ether
  • benzophenone