3-nitrotyrosine and sinapinic-acid

Peroxynitrite (ONOO(-)), formed from a reaction of superoxide and nitric oxide, is one of the most potent cytotoxic species that are known to oxidize cellular constituents including essential proteins, lipids, and DNA. In this study, the ability of sinapic acid (3,5-dimethoxy-4-hydroxycinnamic acid), isolated from Brassica juncea, to scavenge ONOO(-) was investigated. The data obtained show that sinapic acid can efficiently scavenge native ONOO(-) as well as ONOO(-) derived from the peroxynitrite donor 3-morpholinosydnonimine hydrochloride (SIN-1). Spectrophotometric analyses revealed that sinapic acid suppressed the formation of ONOO(-)-mediated tyrosine nitration through an electron donation mechanism. In further studies, sinapic acid also showed a significant ability of inhibiting nitration of bovine serum albumin and low-density lipoprotein (LDL) in a dose-dependent manner. Sinapic acid decreased the LDL peroxidation induced by SIN-1-derived ONOO(-). The present study suggests that sinapic acid has an efficient ONOO(-) scavenging ability, which may well be a potent ONOO(-) oxidant scavenger for the protection of the cellular defense activity against the ONOO(-)-involved diseases.

Topics: Brassica; Coumaric Acids; Free Radical Scavengers; Lipid Peroxidation; Lipoproteins, LDL; Molsidomine; Nitrates; Nitric Oxide; Oxidation-Reduction; Peroxynitrous Acid; Serum Albumin, Bovine; Superoxides; Tyrosine

The peroxynitrite-scavenging ability of some phenolic antioxidants, p-coumaric acid, caffeic acid and sinapinic acid, was examined and compared with ascorbic acid and tocopherol using 3-nitrotyrosine formation as a marker. Among these, caffeic acid and sinapinic acid strongly inhibited the formation of 3-nitrotyrosine in protein. The treatment of protein with peroxynitrite in the presence of sinapinic acid, but not caffeic acid, produced a novel product determined by reversed-phase high performance liquid chromatography (HPLC). The product formed was purified and then identified as a mono-lactone type dimer (ML) of sinapinic acid by nuclear magnetic resonance (NMR) and liquid chromatography-mass spectrometry (LC-MS). This ML was converted from a di-lactone type dimer, obtained from sinapinic acid with peroxidase/hydrogen peroxide, in neutral buffer. In this report, we have proposed that the ML of sinapinic acid is generated via one-electron oxidation by peroxynitrite treatment.

Topics: Chromatography, High Pressure Liquid; Coumaric Acids; Dimerization; Magnetic Resonance Spectroscopy; Mass Spectrometry; Nitrates; Oxidation-Reduction; Proteins; Tyrosine