Energetic and electronic computation of the two-hydrogen atom donation process in catecholic and non-catecholic anthocyanidins

被引:12
作者
Ali, Hussein M. [1 ]
Ali, Isra H. [2 ]
机构
[1] Ain Shams Univ, Agr Biochem Dept, Fac Agr, Cairo, Egypt
[2] Zewail City Sci & Technol, Nanomat Lab, CMS, Giza 12588, Egypt
关键词
Anthocyanidins; Bond dissociation energy; Radical stabilization; Diradical formation; Catechols; DFT calculations; RADICAL SCAVENGING ACTIVITY; ANTIOXIDANT ACTIVITY; PHENOLIC-COMPOUNDS; NAPHTHALENE DIOLS; AB-INITIO; CYANIDIN; QSAR; WINE; RICH;
D O I
10.1016/j.foodchem.2017.09.120
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Antioxidant activity of anthocyanidins is greatly affected by the 3-hydroxyl group and/or a catecholic moiety. The two-hydrogen atom donation process is frequently used to explain the high antioxidant activity of polyphenolic compounds leading to the formation of stable diketones e. g. 1,2-quinones. Thermodynamic parameters, HOMO and spin density were computed to identify the favoured path, either through the 3-hydroxyl group or through the catecholic moiety in a series of catecholic and non-catecholic 3-oxy-(and deoxy)-anthocyanidins. DFT calculations showed that the donation process in non-catecholic anthocyanidins depended on the substituents on ring B. Anthocyanidins with 3', 5'-diOMe groups showed donation through 3,4'-OH or, otherwise, through 3,5-OH groups. Catecholic 3-oxyanthocyanidins, on the other hand, showed donation through the 3,4'OH path rather than the catecholic path (4', 3'-path). The 3,4'-path was favoured by the formation of planar 3-radicals in the first step and the stabilization of 4'-radicals in the second step by H-bonding with the 3'-OH group.
引用
收藏
页码:145 / 150
页数:6
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