Enhanced radical scavenging activity of a procyanidin B3 analogue comprised of a dimer of planar catechin
Enhanced radical scavenging activity of a procyanidin B3 analogue comprised of a dimer of planar catechin
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DOI：
10.1016/j.bmcl.2017.10.007
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发表时间：
2017-11-15
影响因子：
2.7
通讯作者：
Fukuhara, Kiyoshi
中科院分区：
文献类型：
--
作者：
Mizuno, Mirei;Nakanishi, Ikuo;Fukuhara, Kiyoshi
原花青素是儿茶素的低聚体，具有很强的抗氧化活性，能抑制氧化低密度脂蛋白与凝集素样氧化低密度脂蛋白受体(LOX-1)的结合，参与动脉硬化的发生和发展。前人试图开发具有更强的抗氧化活性和对LOX-1更强抑制作用的原花青素衍生物(1)，合成了一种新的原花青素衍生物(1)，其中原花青素B3中的一个儿茶素分子的几何构型被限制为平面取向。其清除自由基活性是原花青素B3的1.9倍。在这里，我们合成了另一个原花青素B3类似物(2)，其中两个儿茶素分子在二聚体中的几何构型都被限制在平面方向上。2的自由基清除活性是1的1.5倍，提示2可能是降低动脉硬化或相关脑血管疾病所致氧化应激的有效候选药物。(C)爱思唯尔有限公司发布的2017年。
Proanthocyanidins are oligomers of catechins that exhibit potent antioxidative activity and inhibit binding of oxidized low-density lipoprotein (OxLDL) to the lectin-like oxidized LDL receptor (LOX-1), which is involved in the onset and development of arteriosclerosis. Previous attempts aimed at developing proanthocyanidin derivatives with more potent antioxidative activity and stronger inhibition for LOX-1 demonstrated the synthesis of a novel proanthocyanidin derivative (1), in which the geometry of one catechin molecule in procyanidin B3 was constrained to a planar orientation. The radical scavenging activity of 1 was 1.9-fold higher than that of procyanidin B3. Herein, we synthesized another procyanidin B3 analogue (2), in which the geometries of both catechin molecules in the dimer were constrained to planar orientations. The radical scavenging activity of 2 was 1.5-fold higher than that of 1, suggesting that 2 may be a more effective candidate than 1 as a therapeutic agent to reduce oxidative stress induced in arteriosclerosis or related cerebrovascular disease. (C) 2017 Published by Elsevier Ltd.