Inhibitory mechanism of sinapinic acid against peroxynitrite‐mediated tyrosine nitration of protein in vitro

FEBS Letters

Osawa, Toshihiko³  Kato, Yoji²  Niwa, Toshio¹  Doi, Umeyuki¹ 

[1] Department of Research and Development, San-ei Sucrochemical Co., Ltd., Chita 478-8503, Japan;School of Humanities for Environmental Policy and Technology, Himeji Institute of Technology, Himeji 670-0092, Japan;Laboratory of Food and Biodynamics, Nagoya University Graduate School of Bioagricultural Sciences, Nagoya 464-8601, Japan

关键词: Peroxynitrite;    Sinapinic acid;    Adduct;    Nitrotyrosine;    Phenolic antioxidant;    NMR;    nuclear magnetic resonance;    LC-MS;    liquid chromatography-mass spectrometry;    ML;    mono-lactone type dimer;    DL;    di-lactone type dimer;   

DOI  :  10.1016/S0014-5793(99)01216-8

学科分类：生物化学/生物物理

来源: John Wiley & Sons Ltd.

【 摘 要 】

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.

【 授权许可】

Unknown