Three Novel Monoterpenoid Glycosides From Fruits Of Eleutherococcus Henryi

Nat Prod Res. 2021 Apr;35(8):1299-1306. doi: 10.1080/14786419.2019.1645661. Epub 2019 Jul 30.

Abstract

The phytochemical investigation on the fruits of Eleutherococcus henryi (Araliaceae) resulted in the discovery of three novel monoterpene glycosides, eleuhenryiside A (1), eleuhenryiside B (2), and eleuhenryiside C (3), as well as a known lignan, (-)-kobusin (4). Their chemical structures were elucidated by mass, 1 D- and 2 D-NMR spectroscopy. The chemical structures of new compounds 1-3 were determined to be (2E,6R)-6-hydroxy-2,6-dimethyl-2,7-octadien-1-yl-(6'-O-acetyl)-O-β-glucopyranoside, (2Z,6R)-6-hydroxy-2,6-dimethyl-2,7-octadien-1-yl-(6'-O-acetyl)-O-β-glucopyranoside, and (-)-(4 R)-4,7-dihydroxy-1-menthene 7-O-β-glucopyranoside, respectively. The anti-neuroinflammatory and anti-inflammatory activities of these compounds were evaluated with LPS-stimulated BV2 microglia and RAW264.7 macrophage, respectively. The results showed that new compounds 1 and 3 have inhibitory effects of NO production with IC50 values of 32.50 ± 1.60 and 3.54 ± 0.20 μM in LPS-stimulated BV2 microglia. Also, (-)-kobusin (4) has abilities to inhibit NO production with the IC50 values of 14.25 ± 2.69 and 36.35 ± 6.27 μM in BV2 and RAW264.7 cells, respectively, which indicated that it may possess the potential anti-neuroinflammatory and anti-inflammatory activities.

Keywords: Araliaceae; Eleutherococcus henryi; eleuhenryiside A; eleuhenryiside B; eleuhenryiside C; monoterpenoid glycosides.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
  • Benzodioxoles / chemistry
  • Drug Evaluation, Preclinical
  • Eleutherococcus / chemistry*
  • Fruit / chemistry
  • Glycosides / chemistry
  • Glycosides / pharmacology
  • Lignans / chemistry
  • Lipopolysaccharides / toxicity
  • Magnetic Resonance Spectroscopy
  • Mice
  • Microglia / drug effects
  • Molecular Structure
  • Monoterpenes / chemistry*
  • Monoterpenes / pharmacology*
  • RAW 264.7 Cells

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Benzodioxoles
  • Glycosides
  • Lignans
  • Lipopolysaccharides
  • Monoterpenes
  • kobusin