State Key Laboratory of Food Nutrition and Safety, Tianjin University of Science & Technology, Tianjin 300222, China.
Shaanxi Engineering Laboratory for Food Green Processing and Safety Control, and Shaanxi Key Laboratory for Hazard Factors Assessment in Processing and Storage of Agricultural Products, College of Food Engineering and Nutritional Science, Shaanxi Normal University, Xi'an 710119, China.
Biomolecules. 2019 Jul 9;9(7):268. doi: 10.3390/biom9070268.
Stilbenes, particularly resveratrol and resveratrol dimers, could effectively quench singlet oxygen (O). It was reported that both resorcinol and carbon-carbon double bond quenching O can participate in the mechanism. However, it is still not clear which structure plays a dominant role in quenching O. To investigate the characteristic structure in the mechanism of quenching O, the resveratrol, pterostilbene and piceatannol quenching O abilities were compared by UHPLC-QTOF-MS and UHPLC-QQQ-MS. Results showed that catechol, carbon-carbon double bond and resorcinol participated in the quenching of O. Catechol ring plays a leading role in the mechanism, and the contribution of the structures in quenching O activity are as follows: catechol ring > carbon-carbon double bond > resorcinol ring, which is supported by the calculation of energy. Our findings will contribute to the future screening of stilbenes with higher activity, and those stilbenes may have great therapeutic potential in O-mediated diseases.
芪类物质，特别是白藜芦醇和白藜芦醇二聚体，可以有效地猝灭单线态氧（1O2）。据报道，间苯二酚和碳碳双键都可以参与猝灭 1O2 的机制。然而，哪种结构在猝灭 1O2 中起主导作用仍不清楚。为了研究猝灭 1O2 机制中的特征结构，通过 UHPLC-QTOF-MS 和 UHPLC-QQQ-MS 比较了白藜芦醇、紫檀芪和紫檀芪醇猝灭 1O2 的能力。结果表明，间苯二酚、碳碳双键和间苯二酚参与了 1O2 的猝灭。儿茶酚环在机制中起主导作用，猝灭 1O2 活性的结构贡献如下：儿茶酚环＞碳碳双键＞间苯二酚环，这得到了能量计算的支持。我们的发现将有助于未来筛选具有更高活性的芪类物质，这些芪类物质在 1O2 介导的疾病中可能具有巨大的治疗潜力。
