Euphopias A-C: Three Rearranged Jatrophane Diterpenoids with Tricyclo[8.3.0.02,7]tridecane and Tetracyclo[11.3.0.02,10.03,7]hexadecane Cores from Euphorbia helioscopia

Org Lett. 2020 Oct 16;22(20):7820-7824. doi: 10.1021/acs.orglett.0c02676. Epub 2020 Sep 29.

Abstract

Euphopias A-C (1-3), three rearranged jatrophane-type diterpenoids with tricyclo[8.3.0.02,7]tridecane (1 and 2) and tetracyclo[11.3.0.02,10.03,7]hexadecane (3) cores, were isolated from Euphorbia helioscopia. Comprehensive spectroscopic analyses, quantum-chemical calculations, and X-ray diffractions were used to identify their structures. Compounds 1-3 could significantly inhibit NLRP3 inflammasome activation and block NLRP3 inflammasome-induced pyroptosis. Additionally, a mechanistic study revealed that 2 could ameliorate mitochondria damage, thereby interrupting NLRP3 inflammasome activation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkanes / chemistry
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification
  • Diterpenes / pharmacology*
  • Euphorbia / chemistry*
  • Molecular Structure
  • NLR Family, Pyrin Domain-Containing 3 Protein / antagonists & inhibitors*
  • NLR Family, Pyrin Domain-Containing 3 Protein / chemistry

Substances

  • Alkanes
  • Diterpenes
  • NLR Family, Pyrin Domain-Containing 3 Protein
  • jatrophane
  • n-hexadecane