Antiradical and reductant activities of anthocyanidins and anthocyanins, structure-activity relationship and synthesis
Antiradical and reductant activities of anthocyanidins and anthocyanins, structure-activity relationship and synthesis
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DOI：
10.1016/j.foodchem.2015.09.003
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发表时间：
2016-03-01
期刊：
影响因子：
8.8
通讯作者：
Al-Rashidi, Mona N.
中科院分区：
文献类型：
--
作者：
Ali, Hussein M.;Almagribi, Wafaa;Al-Rashidi, Mona N.
在FRAP实验中考察了8种花青素、7种花青素和2种合成的4′-羟基黄酮作为DPPH、ABTS和羟基自由基的给氢体和电子给体。大多数化合物的活性优于邻苯三酚和邻苯三酚。构效关系（SAR）研究表明，在没有3-OH的情况下，4,5或7-OH的自由基只能通过pyryum氧共振来稳定，而3-OH则通过花青素类半醌类共振来稳定，从而改善了氢原子的给能。3-OH基团也增强了电子给能。花青素和各自的花青素表现出相似的趋势和相近的活性。不同类型的糖单元与3-OH基团或反离子结合对活性的影响较小。儿茶酚的结构改善了氢和电子的给能。缺乏儿茶酚结构的化合物的h原子和电子给能顺序依次下降（Mv > Pn > Pg > Ap > 4'- oh - flavyum），与羟基和/或甲氧基数量的减少相一致。(C) 2015 Elsevier Ltd.版权所有。
Eight anthocyanidins, seven anthocyanins and two synthesized 4'-hydroxy flavyliums were examined as hydrogen donors to DPPH, ABTS and hydroxyl radicals, and as electron donors in the FRAP assay. Most compounds gave better activities than trolox and catechol. A structure-activity relationship (SAR) study showed that, in the absence of the 3-OH group, radicals of the 4, 5 or 7-OH groups can only be stabilized by resonance through pyrylium oxygen, while 3-OH group improved hydrogen atom donation because of the stabilization by anthocyanidin semiquinone-like resonance. Electron donation was also enhanced by the 3-OH group. Both anthocyanidins and their respective anthocyanins showed similar trends and close activities. Different types of sugar unit bonded to the 3-OH group or counter ion had minor effect on activities. The catechol structure improved both hydrogen and electron donation. Compounds lacking the catechol structure had a decreasing order of H-atom and electron donation (Mv > Pn > Pg > Ap > 4'-OH-flavylium) consistent with the decreasing number of their hydroxyl and/or methoxy groups. (C) 2015 Elsevier Ltd. All rights reserved.