Substituent Inductive Effects on the Electrochemical Oxidation of Flavonoids Studied by Square Wave Voltammetry and Ab Initio Calculations.
Substituent Inductive Effects on the Electrochemical Oxidation of Flavonoids Studied by Square Wave Voltammetry and Ab Initio Calculations.
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DOI：
10.3390/molecules21111422
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发表时间：
2016-10-27
期刊：
影响因子：
--
通讯作者：
Videa M
中科院分区：
文献类型：
--
作者：
Arroyo-Currás N;Rosas-García VM;Videa M
类黄酮是人类饮食中常见的天然产物，具有抗氧化、抗炎和抗肝毒性的活性。这些营养性质可能与类黄酮的电化学活性有关。为了进一步了解结构-电化学活性关系以及羟基取代基对黄酮类化合物氧化还原电位的诱导作用，我们对黄酮类化合物进行了方波伏安实验和从头计算，根据黄酮类化合物骨架上羟基取代基的数量和位置的系统变化选择了8种黄酮类化合物：3种黄酮醇、3种花青素、1种花青素和黄酮类化合物骨架黄酮。我们比较了黄烷B环中-OH基团的数量对所考虑的黄酮氧化电位的影响，发现黄酮醇和花青素之间存在线性相关性（）。我们通过从头算量子化学计算分析了-OH取代基的位置和数目对电子密度分布的影响。我们提出了结构特征和氧化电位之间的直接相关性，从而对这些分子的氧化还原化学有了更深入的了解。
Flavonoids are natural products commonly found in the human diet that show antioxidant, anti-inflammatory and anti-hepatotoxic activities. These nutraceutical properties may relate to the electrochemical activity of flavonoids. To increase the understanding of structure–electrochemical activity relations and the inductive effects that OH substituents have on the redox potential of flavonoids, we carried out square-wave voltammetry experiments and ab initio calculations of eight flavonoids selected following a systematic variation in the number of hydroxyl substituents and their location on the flavan backbone: three flavonols, three anthocyanidins, one anthocyanin and the flavonoid backbone flavone. We compared the effect that the number of –OH groups in the ring B of flavan has on the oxidation potential of the flavonoids considered, finding linear correlations for both flavonols and anthocyanidins (). We analyzed the effects that position and number of –OH substituents have on electron density distributions via ab initio quantum chemical calculations. We present direct correlations between structural features and oxidation potentials that provide a deeper insight into the redox chemistry of these molecules.
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影响因子：
5.6
作者：
Aparicio, Santiago
通讯作者：
Aparicio, Santiago
影响因子：
5
作者：
Masek, Anna
通讯作者：
Masek, Anna
影响因子：
8.8
作者：
Gulaboski, Rubin;Mirceski, Valentin;Mitrev, Sasa
通讯作者：
Mitrev, Sasa
DOI：
10.1007/bf01092246
发表时间：
1973-01-01
期刊：
QUALITAS PLANTARUM-PLANT FOODS FOR HUMAN NUTRITION
影响因子：
--
作者：
KUHNAU, J
通讯作者：
KUHNAU, J
影响因子：
8.6
作者：
Hanwell MD;Curtis DE;Lonie DC;Vandermeersch T;Zurek E;Hutchison GR
通讯作者：
Hutchison GR