Euphzycopias A-I, macrocyclic diterpenes with NLRP3 inflammasome inhibitory activity from Euphorbia helioscopia L

Fitoterapia. 2022 Mar:157:105139. doi: 10.1016/j.fitote.2022.105139. Epub 2022 Jan 31.

Abstract

A phytochemical investigation was conducted on Euphorbia helioscopia, resulting in the isolation of thirteen compounds, including nine undescribed diterpenoids, Euphzycopias A - I (1-9), of which the skeletons of compounds 1-4 were found in E. helioscopia L. Compounds 1-3 had 5/7/6 cyclic systems, while compound 4 had a 4/11 polycyclic system with a 4,7-cyclic ether between C-4 and C-7. The anti-inflammasome test using the isolated compounds (1-6, 8-13) showed that the diterpenes from E. helioscopia L. had a strong inhibitory effect on NLRP3 inflammasomes with IC50 values of 3.34-14.92 μM.

Keywords: Diterpenoids; Euphorbia helioscopia L.; Euphorbiaceae; NLRP3 inflammasome.

MeSH terms

  • Diterpenes / chemistry
  • Diterpenes / isolation & purification
  • Diterpenes / pharmacology*
  • Euphorbia / chemistry*
  • Humans
  • Inflammasomes / chemistry
  • Inflammasomes / isolation & purification
  • Inflammasomes / pharmacology*
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • NLR Family, Pyrin Domain-Containing 3 Protein / antagonists & inhibitors
  • Optical Rotation
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology
  • Spectrophotometry, Infrared

Substances

  • Diterpenes
  • Inflammasomes
  • NLR Family, Pyrin Domain-Containing 3 Protein
  • Plant Extracts