Discovery of Novel Pentacyclic Triterpene Acid Amide Derivatives as Excellent Antimicrobial Agents Dependent on Generation of Reactive Oxygen Species

Int J Mol Sci. 2023 Jun 24;24(13):10566. doi: 10.3390/ijms241310566.

Abstract

Developing new agricultural bactericides is a feasible strategy for stopping the increase in the resistance of plant pathogenic bacteria. Some pentacyclic triterpene acid derivatives were elaborately designed and synthesized. In particular, compound A22 exhibited the best antimicrobial activity against Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas axonopodis pv. citri (Xac) with EC50 values of 3.34 and 3.30 mg L-1, respectively. The antimicrobial mechanism showed that the compound A22 induced excessive production and accumulation of reactive oxygen species (ROS) in Xoo cells, leading to a decrease in superoxide dismutase and catalase enzyme activities and an increase in malondialdehyde content. A22 also produced increases in Xoo cell membrane permeability and eventual cell death. In addition, in vivo experiments showed that A22 at 200 mg L-1 exhibited protective activity against rice bacterial blight (50.44%) and citrus canker disease (84.37%). Therefore, this study provides a paradigm for the agricultural application of pentacyclic triterpene acid.

Keywords: 18β-glycyrrhetinic acid; antibacterial activities; reactive oxygen species; ursolic acid.

MeSH terms

  • Amides / metabolism
  • Anti-Bacterial Agents / metabolism
  • Anti-Bacterial Agents / pharmacology
  • Microbial Sensitivity Tests
  • Oryza* / metabolism
  • Pentacyclic Triterpenes / metabolism
  • Pentacyclic Triterpenes / pharmacology
  • Plant Diseases / microbiology
  • Reactive Oxygen Species / metabolism
  • Triterpenes* / metabolism
  • Triterpenes* / pharmacology
  • Xanthomonas* / metabolism

Substances

  • Reactive Oxygen Species
  • Amides
  • Triterpenes
  • Anti-Bacterial Agents
  • Pentacyclic Triterpenes

Supplementary concepts

  • Xanthomonas oryzae
  • Xanthomonas citri