(+/-)-Alashanoid N, Two Enantiomeric Sesquiterpenes from Syringa pinnatifolia

Chem Biodivers. 2021 Mar;18(3):e2001065. doi: 10.1002/cbdv.202001065. Epub 2021 Feb 12.

Abstract

Two enantiomeric humulane sesquiterpenes, namely (+)-alashanoid N (1a) and (-)-alashanoid N (1b), along with two known analogs ((2R,3R,5R)-2,3-epoxy-6,9-humuladien-5-ol-8-one (2) and (2R,3S,5R)-2,3-epoxy-6,9-humuladien-5-ol-8-one (3)), were described from the peeled stems of a folk Mongolian herbal medicine Syringa pinnatifolia. Their structures were characterized based on UV, IR, NMR, and HR-ESI-MS data analyses, and the absolute configurations were determined by data analysis of X-ray diffraction and quantum chemical calculations. (+/-)-Alashanoid N showed inhibition against NO production in RAW 264.7 macrophage cells with IC50 values of 90.1 μM and 71.7 μM, and protective effect against oxygen-glucose deprivation injury to H9c2 cells at a concentration of 20 μM and 5 μM, respectively.

Keywords: ECD calculation; Syringa pinnatifolia; alashanoid N; enantiomer; sesquiterpene.

MeSH terms

  • Animals
  • Cell Survival / drug effects
  • Dose-Response Relationship, Drug
  • Glucose / antagonists & inhibitors
  • Glucose / metabolism
  • Lipopolysaccharides / antagonists & inhibitors
  • Lipopolysaccharides / pharmacology
  • Mice
  • Molecular Conformation
  • Nitric Oxide / antagonists & inhibitors
  • Nitric Oxide / biosynthesis
  • Oxygen / metabolism
  • Protective Agents / chemistry
  • Protective Agents / isolation & purification
  • Protective Agents / pharmacology*
  • RAW 264.7 Cells
  • Rats
  • Stereoisomerism
  • Structure-Activity Relationship
  • Syringa / chemistry*

Substances

  • Lipopolysaccharides
  • Protective Agents
  • Nitric Oxide
  • Glucose
  • Oxygen