Comparison of the Antioxidant Effects of Quercitrin and Isoquercitrin: Understanding the Role of the 6″-OH Group.
Comparison of the Antioxidant Effects of Quercitrin and Isoquercitrin: Understanding the Role of the 6″-OH Group.
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槲皮苷和异槲皮苷的抗氧化作用比较：了解 6-OH 基团的作用
DOI：
10.3390/molecules21091246
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发表时间：
2016-09-19
期刊：
影响因子：
--
通讯作者：
Chen D
中科院分区：
文献类型：
--
作者：
Li X;Jiang Q;Wang T;Liu J;Chen D
6″-OH （ω-OH）基团在黄酮类苷抗氧化活性中的作用在很大程度上被忽视。本文选择槲皮素（槲皮素-3- o -鼠李糖苷）和异槲皮素（槲皮素-3- o -葡萄糖苷）作为模型化合物，研究6″-OH基团在几种抗氧化途径中的作用，包括Fe2+结合、给氢（h -给氢）和电子转移（ET）。结果表明，槲皮苷和异槲皮苷均表现出剂量依赖性的抗氧化活性。然而，异槲皮素在Fe2+结合、et基铁离子还原抗氧化能力和多途径超氧阴离子清除试验中显示出比槲皮素更高的活性水平。相比之下，槲皮苷在以h -供体为基础的1,1-二苯基-2-苦基肼基自由基清除实验中表现出比异槲皮苷更大的活性。最后，在基于氧化损伤间充质干细胞（MSC）模型的3-（4,5-二甲基噻唑-2-基）-2,5-二苯基实验中，异槲皮苷比槲皮苷更有效地发挥细胞保护作用。基于这些结果，我们得出结论：(1)槲皮苷和异槲皮苷可以间接（即螯合或结合）或直接参与活性氧（ROS）的清除，从而保护MSCs免受ROS诱导的氧化损伤；(2)与槲皮素相比，异槲皮素中的6″-OH基团增强了其ET和Fe2+螯合能力，通过位阻或氢键作用降低了其给h能力；(3)异槲皮素比槲皮素具有更高的活性氧清除活性，使其能够更好地保护MSCs免受活性氧诱导的氧化损伤。
The role of the 6″-OH (ω-OH) group in the antioxidant activity of flavonoid glycosides has been largely overlooked. Herein, we selected quercitrin (quercetin-3-O-rhamnoside) and isoquercitrin (quercetin-3-O-glucoside) as model compounds to investigate the role of the 6″-OH group in several antioxidant pathways, including Fe2+-binding, hydrogen-donating (H-donating), and electron-transfer (ET). The results revealed that quercitrin and isoquercitrin both exhibited dose-dependent antioxidant activities. However, isoquercitrin showed higher levels of activity than quercitrin in the Fe2+-binding, ET-based ferric ion reducing antioxidant power, and multi-pathways-based superoxide anion-scavenging assays. In contrast, quercitrin exhibited greater activity than isoquercitrin in an H-donating-based 1,1-diphenyl-2-picrylhydrazyl radical-scavenging assay. Finally, in a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl assay based on an oxidatively damaged mesenchymal stem cell (MSC) model, isoquercitrin performed more effectively as a cytoprotector than quercitrin. Based on these results, we concluded that (1) quercitrin and isoquercitrin can both indirectly (i.e., Fe2+-chelating or Fe2+-binding) and directly participate in the scavenging of reactive oxygen species (ROS) to protect MSCs against ROS-induced oxidative damage; (2) the 6″-OH group in isoquercitrin enhanced its ET and Fe2+-chelating abilities and lowered its H-donating abilities via steric hindrance or H-bonding compared with quercitrin; and (3) isoquercitrin exhibited higher ROS scavenging activity than quercitrin, allowing it to improve protect MSCs against ROS-induced oxidative damage.
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DOI：
10.3390/molecules21030356
发表时间：
2016-03-21
期刊：
Molecules (Basel, Switzerland)
影响因子：
--
作者：
Zhu M;Li J;Wang K;Hao X;Ge R;Li Q
通讯作者：
Li Q
影响因子：
11
作者：
Saeed H;Ahsan M;Saleem Z;Iqtedar M;Islam M;Danish Z;Khan AM
通讯作者：
Khan AM
二氢杨梅素对 OH 诱导的间充质干细胞损伤的保护作用及机制化学
影响因子：
4.6
作者：
Li, Xican;Liu, Jingjing;Chen, Dongfeng
通讯作者：
Chen, Dongfeng
影响因子：
2.2
作者：
Holtomo, Olivier;Nsangou, Mama;Motapon, Ousmanou
通讯作者：
Motapon, Ousmanou
影响因子：
2.9
作者：
Benzie, IFF;Strain, JJ
通讯作者：
Strain, JJ