Synthesis and antioxidant activity of a procyanidin B3 analogue
Synthesis and antioxidant activity of a procyanidin B3 analogue
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DOI：
10.1016/j.bmcl.2016.12.067
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发表时间：
2017-02-15
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一种低聚体，是一种天然的抗氧化剂，是凝集素样氧化型低密度脂蛋白受体-1的有效抑制剂，参与了动脉硬化的发病机制。我们合成了原花青素类似物1，其中(+)-儿茶素的二聚体原花青素B3中的一个儿茶素分子的几何构型被约束为平面。结果表明，原花青素的清除能力是(+)-儿茶素的3.8倍，原花青素类似物1的清除能力是原花青素B3的1.9倍。新设计的原花青素类似物1有望成为治疗动脉硬化和相关脑血管疾病的先导化合物。(C)2016爱思唯尔有限公司。保留所有权利。
Proanthocyanidin, an oligomer of catechin, is a natural antioxidant and a potent inhibitor of lectin-like oxidized LDL receptor-1, which is involved in the pathogenesis of arteriosclerosis. We synthesized proanthocyanidin analogue 1, in which the geometry of one catechin molecule in procyanidin B3, a dimer of (+)-catechin, is constrained to be planar. The antioxidant activities of the compounds were evaluated in terms of their capacities to scavenge galvinoxyl radicals, and results demonstrate that while procyanidin was 3.8 times more potent than (+)-catechin, the radical scavenging activity of proanthocyanidin analogue 1 was further increased to 1.9 times that of procyanidin B3. This newly designed proanthocyanidin analogue 1 may be a promising lead compound for the treatment of arteriosclerosis and related cerebrovascular diseases. (C) 2016 Elsevier Ltd. All rights reserved.