Lachnuoic Acids A-F: Ambuic Acid Congeners from a Saprotrophic Lachnum Species

Chem Biodivers. 2024 Apr;21(4):e202400385. doi: 10.1002/cbdv.202400385. Epub 2024 Mar 15.

Abstract

Chemical prospection of an extract derived from a saprotrophic fungus Lachnum sp. IW157 resulted in the isolation and characterization of six unprecedentedly reported ambuic acid analogues named lachnuoic acids A-F (1-6). Chemical structures of 1-6 were determined based on comprehensive 1D and 2D NMR spectroscopic analyses together with HR-ESI-MS spectrometry. The relative configurations of 1-3 were defined by ROESY spectroscopic analyses while their absolute configurations were unambiguously determined by Mosher's esters method. All isolated compounds were subjected to cytotoxic, antimicrobial, antibiofilm and nematicidal activity assays where only lachnuoic acid A (1) revealed potent antimicrobial activity against Staphylococcus aureus and Bacillus subtilis at MIC values of 16.6 and 8.3 μg/mL, respectively.

Keywords: Lachnum; antimicrobial; biofilm inhibition; cytotoxicity.

MeSH terms

  • Anti-Infective Agents* / chemistry
  • Anti-Infective Agents* / pharmacology
  • Ascomycota* / chemistry
  • Cyclohexanones
  • Molecular Structure

Substances

  • ambuic acid
  • Anti-Infective Agents
  • Cyclohexanones