Mechanism of inhibition of peroxynitrite-induced oxidation and nitration by [6]-gingerol.
[6]-Gingerol potently inhibits peroxynitrite-induced oxidation and nitration reactions, but its mechanism of action is unclear. In order to discover the mechanism of inhibition, [6]-gingerol was reacted with peroxynitrite and the reaction mixture was analyzed using HPLC. The HPLC chromatogram showed one novel peak, indicative of the formation of a reaction product between [6]-gingerol and peroxynitrite. This compound was purified and identified as a symmetrical dimer of [6]-gingerol covalently linked at the aromatic ring. It has been assumed that this dimer is generated from a phenoxyl radical intermediate produced from [6]-gingerol via one-electron oxidation by peroxynitrite-derived radicals. We propose a mechanism in which [6]-gingerol scavenges peroxynitrite-derived radicals and consequently inhibits peroxynitrite-induced oxidation and nitration reactions.
Ippoushi
Katsunari
K
National Institute of Vegetable and Tea Science, National Agriculture and Bio-oriented Research Organization, Mie, Japan. ippoushi@affrc.go.jp
Ito
Hidekazu
H
Horie
Hideki
H
Azuma
Keiko
K
D002396:Catechols; D005233:Fatty Alcohols / Q000737:chemistry*; D016166:Free Radical Scavengers / Q000737:chemistry*; D020939:Zingiber officinale; D006801:Humans; D015538:Nitrosation; D010084:Oxidation-Reduction; D030421:Peroxynitrous Acid / Q000737:chemistry; D008517:Phytotherapy; D027343:Rhizome
D002396:Catechols; D005233:Fatty Alcohols; D016166:Free Radical Scavengers; D030421:Peroxynitrous Acid; C007845:gingerol