Antifungal Activity and Action Mechanism Study of Coumarins from Cnidium monnieri Fruit and Structurally Related Compounds

Chem Biodivers. 2021 Dec;18(12):e2100633. doi: 10.1002/cbdv.202100633. Epub 2021 Oct 27.

Abstract

The increasing resistance of plant diseases caused by phytopathogenic fungi highlights the need for highly effective and environmentally benign agents. The antifungal activities of Cnidium monnieri fruit extracts and five isolated compounds as well as structurally related coumarins against five plant pathogenic fungi were evaluated. The acetone extract, which contained the highest amount of five coumarins, showed strongest antifungal activity. Among the coumarin compounds, we found that 4-methoxycoumarin exhibited stronger and broader antifungal activity against five phytopathogenic fungi, and was more potent than osthol. Especially, it could significantly inhibit the growth of Rhizoctonia solani mycelium with an EC50 value of 21 μg mL-1 . Further studies showed that 4-methoxycoumarin affected the structure and function of peroxisomes, inhibited the β-oxidation of fatty acids, decreased the production of ATP and acetyl coenzyme A, and then accumulated ROS by damaging MMP and the mitochondrial function to cause the cell death of R. solani mycelia. 4-Methoxycoumarin presented antifungal efficacy in a concentration- dependent manner in vivo and could be used to prevent the potato black scurf. This study laid the foundation for the future development of 4-methoxycournamin as an alternative and friendly biofungicide.

Keywords: 4-methoxycoumarin; Cnidium monnieri; antifungal activity; coumarins.

MeSH terms

  • Acetyl Coenzyme A / antagonists & inhibitors
  • Acetyl Coenzyme A / biosynthesis
  • Adenosine Triphosphate / antagonists & inhibitors
  • Adenosine Triphosphate / biosynthesis
  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification
  • Antifungal Agents / pharmacology*
  • Cnidium / chemistry*
  • Coumarins / chemistry
  • Coumarins / isolation & purification
  • Coumarins / pharmacology*
  • Fatty Acids / antagonists & inhibitors
  • Fatty Acids / metabolism
  • Fruit / chemistry*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Rhizoctonia / drug effects*
  • Rhizoctonia / growth & development

Substances

  • Antifungal Agents
  • Coumarins
  • Fatty Acids
  • Acetyl Coenzyme A
  • Adenosine Triphosphate

Supplementary concepts

  • Rhizoctonia solani