Structurally diverse triterpenoids with antibacterial activities from Euphorbia humifusa

Bioorg Chem. 2024 Dec:153:107915. doi: 10.1016/j.bioorg.2024.107915. Epub 2024 Oct 26.

Abstract

An exploration of antibacterial components from the whole plant of Euphorbia humifusa led to the isolation of 14 new triterpenoids, euphohumifusoids A-N (1-7 and 9-15), as well as four known analogues (8 and 16-18). Their structures were elucidated by extensively analysis of the spectroscopic data and X-ray crystallography using Cu Kα radiation. Among them, euphohumifusoid A (1) bears an unique 6(7 → 8)abeo scaffold originated from a D:C-friedo-oleanane skeleton for the first time, euphohumifusoids H and I (9 and 10) possess a rare α,β-unsaturated-γ-lactone chain originated from 25,26,27-trinordammaranes, and euphohumifusoid L (13) is a highly modified 3,4-seco-25,26,27-trinorcycloartane. Notably, in antibacterial bioassay, compound 1 displayed excellent antibacterial activities against Bacillus cereus, Staphylococcus aureus, and S.epidermidis with MIC of 12.5, 25, and 25 μg/mL, comparable to the positive controls. Upon exposure to 1 and 2 MIC of 1, B.cereus underwent drastic morphological changes, resulting in complete disruption of the cells. Meanwhile, compound 1 also exhibited remarkable antibiofilm activity against B.cereus at 1 MIC and 2 MIC.

Keywords: Antibacterial activity; Antibiofilm activity; Euphorbia humifusa; Euphorbiaceae; Triterpenoid.

MeSH terms

  • Anti-Bacterial Agents* / chemistry
  • Anti-Bacterial Agents* / isolation & purification
  • Anti-Bacterial Agents* / pharmacology
  • Bacillus cereus / drug effects
  • Crystallography, X-Ray
  • Dose-Response Relationship, Drug
  • Euphorbia* / chemistry
  • Microbial Sensitivity Tests*
  • Molecular Structure
  • Staphylococcus aureus / drug effects
  • Staphylococcus epidermidis / drug effects
  • Structure-Activity Relationship
  • Triterpenes* / chemistry
  • Triterpenes* / isolation & purification
  • Triterpenes* / pharmacology

Substances

  • Anti-Bacterial Agents
  • Triterpenes