Three Undescribed Protoilludane-Type Sesquiterpene Aryl Esters from Armillaria gallica

Chem Biodivers. 2024 Sep;21(9):e202401303. doi: 10.1002/cbdv.202401303. Epub 2024 Aug 19.

Abstract

Three previously undescribed protoilludane-type sesquiterpene aryl esters, armillanals A-C (1-3), along with seven known ones (4-10) were obtained from Armillaria gallica Marxm. & Romagn. Compounds 1 and 2 were a rare class of sesquiterpenes featuring the Δ2(3) and Δ12(13)-protoilludane skeleton. Their structures were established by extensive spectroscopic methods. Based on electronic circular dichroism (ECD) calculations, the absolute configurations of three new compounds (1-3) were determined. The anti-inflammatory activity of compounds 1-10 was screened and compound 3 could dose-dependently decrease the level of lactate dehydrogenase, showing IC50 value of 4.525 μM.

Keywords: Armillaria gallica; NLRP3 inflammasome inhibition activity; Protoilludane-type sesquiterpene aryl esters.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology
  • Armillaria* / chemistry
  • Dose-Response Relationship, Drug
  • Esters* / chemistry
  • Esters* / isolation & purification
  • Esters* / pharmacology
  • L-Lactate Dehydrogenase / antagonists & inhibitors
  • L-Lactate Dehydrogenase / metabolism
  • Lipopolysaccharides / antagonists & inhibitors
  • Lipopolysaccharides / pharmacology
  • Mice
  • Molecular Conformation
  • Molecular Structure
  • RAW 264.7 Cells
  • Sesquiterpenes* / chemistry
  • Sesquiterpenes* / isolation & purification
  • Sesquiterpenes* / pharmacology
  • Structure-Activity Relationship

Substances

  • Sesquiterpenes
  • Esters
  • L-Lactate Dehydrogenase
  • Lipopolysaccharides
  • Anti-Inflammatory Agents