New eudesmane sesquiterpenes from Alpinia oxyphylla and determination of their inhibitory effects on microglia

Bioorg Med Chem Lett. 2013 Jul 1;23(13):3879-83. doi: 10.1016/j.bmcl.2013.04.072. Epub 2013 May 7.

Abstract

The fruits of Alpinia oxyphylla are used as healthcare products for the protection on neurons and prevention of dementia. Two new noreudesmane sesquiterpenoids, (5R,7S,10S)-5-hydroxy-13-noreudesma-3-en-2,11-dione (1) and (10R)-13-noreudesma-4,6-dien-3,11-dione (2), and a new eudesmane sesquiterpenoid, (5S,8R,10R)-2-oxoeudesma-3,7(11)-dien-12,8-olide (3), as well as 12 known sesquiterpenoids, were isolated from the fruits of A. oxyphylla. The structures of the new compounds (1-3) were elucidated on the basis of spectroscopic data and circular dichroism experiments. All isolates were evaluated their neuroprotective potential by inhibitory assay on nitric oxide (NO) and tumor necrosis factor-α (TNF-α) production in lipopolysaccharide (LPS)-induced mouse microglia BV-2 cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alpinia / chemistry*
  • Animals
  • Dose-Response Relationship, Drug
  • Fruit / chemistry
  • Lipopolysaccharides / antagonists & inhibitors
  • Lipopolysaccharides / pharmacology
  • Mice
  • Microglia / drug effects*
  • Microglia / metabolism
  • Molecular Conformation
  • Nitric Oxide / antagonists & inhibitors*
  • Nitric Oxide / biosynthesis
  • Sesquiterpenes, Eudesmane / chemistry
  • Sesquiterpenes, Eudesmane / isolation & purification
  • Sesquiterpenes, Eudesmane / pharmacology*
  • Structure-Activity Relationship
  • Tumor Necrosis Factor-alpha / antagonists & inhibitors*
  • Tumor Necrosis Factor-alpha / biosynthesis

Substances

  • Lipopolysaccharides
  • Sesquiterpenes, Eudesmane
  • Tumor Necrosis Factor-alpha
  • Nitric Oxide