Phenylpropanoid ester from Zingiber officinale and their inhibitory effects on the production of nitric oxide

Arch Pharm Res. 2012 Feb;35(2):315-20. doi: 10.1007/s12272-012-0211-y. Epub 2012 Feb 28.

Abstract

A new phenylpropanoid ester mixture, (E)-geranylferulic acid (1a) and (Z)-geranylferulic acid (1b), along with 13 known compounds, [6]-gingerol (2), [8]-gingerol (3), [10]-gingerdione (4), 1-dehydro-[6]-gingerdione (5), 1-dehydro-[8]-gingerdione (6), [6]-paradol (7), [8]-paradol (8), [6]-gingeroldiacetate (9), 6-hydroxy-[6]-shogaol (10), galanolactone (11), trans-®-sesquiphellandrol (12), trans-sesquipiperitol (13), and 4α,5β-dihydroxybisabola-2,10-diene (14) were isolated from ethanol extract of Zingiber officinale. Their structures were determined based on the spectroscopic (1D, 2D-NMR and MS) and chemical evidence. All of the isolates were evaluated for their potential to inhibit LPS-induced production of nitric oxide in murine macrophage RAW264.7 cells. Compounds 1-12 were found to inhibit nitric oxide production with IC(50) values ranging from 5.5 to 28.5 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Survival / drug effects
  • Cells, Cultured
  • Coumaric Acids / chemistry
  • Coumaric Acids / isolation & purification*
  • Coumaric Acids / pharmacology*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification*
  • Enzyme Inhibitors / pharmacology*
  • Esters / chemistry
  • Esters / isolation & purification
  • Esters / pharmacology
  • Macrophages / drug effects
  • Mice
  • Nitric Oxide / biosynthesis
  • Nitric Oxide Synthase Type II / antagonists & inhibitors*
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology
  • Structure-Activity Relationship
  • Zingiber officinale / chemistry*

Substances

  • (E)-geranylferulic acid
  • Coumaric Acids
  • Enzyme Inhibitors
  • Esters
  • Plant Extracts
  • Nitric Oxide
  • Nitric Oxide Synthase Type II