Key Laboratory of Forest Plant Ecology, Ministry of Education, Northeast Forestry University, Harbin, Heilongjiang 150040, China.
Key Laboratory of Forest Plant Ecology, Ministry of Education, Northeast Forestry University, Harbin, Heilongjiang 150040, China.
Food Chem. 2019 Mar 1;275:339-345. doi: 10.1016/j.foodchem.2018.09.108. Epub 2018 Sep 19.
Five novel compounds (Gen-NO, Gen-2NO, Gen-NH, Gen-2NH and Gen-6NH) have been designed via introducing an electron-withdrawing group -NO and an electron-donating group -NH into the structure of genistein. The effects of -NO and -NH groups on the antioxidant ability of genistein were investigated via quantum chemistry method in gas and methanol phases. The crucial parameters related to three antioxidant mechanisms were calculated. Moreover, the frontier molecular orbital, natural bond orbital and global descriptive parameters were calculated to evaluate the reactivity of genistein and its derivatives. Calculated results indicate the antioxidant process of genistein and its derivatives inclines to the hydrogen atom transfer (HAT) and sequential proton loss electron transfer (SPLET) mechanisms in gas and methanol phases, respectively. Moreover, introducing -NH group into genistein can improve its antioxidant activity owing to the outstanding activities of amino-substituents of genistein, which will provide valuable guidance for the synthesis of new antioxidants experimentally.
设计了 5 种新型化合物（Gen-NO、Gen-2NO、Gen-NH、Gen-2NH 和 Gen-6NH），通过在染料木黄酮的结构中引入吸电子基团-NO 和供电子基团-NH。通过量子化学方法在气相和甲醇相中研究了-NO 和-NH 基团对染料木黄酮抗氧化能力的影响。计算了与三种抗氧化机制相关的关键参数。此外，还计算了前线分子轨道、自然键轨道和全局描述参数，以评估染料木黄酮及其衍生物的反应性。计算结果表明，染料木黄酮及其衍生物的抗氧化过程在气相和甲醇相中分别倾向于氢原子转移（HAT）和连续质子损失电子转移（SPLET）机制。此外，在染料木黄酮中引入-NH 基团可以提高其抗氧化活性，这是由于染料木黄酮氨基取代基的出色活性，这将为实验合成新型抗氧化剂提供有价值的指导。
