Synthesis and antioxidant activity of a procyanidin B3 analogue

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• 作者：Mirei Mizuno^a ; Ikuo Nakanishi^b ; Satoko Matsubayashi^a ; Kohei Imai^a ; Takuya Arai^a ; ^c ; Ken-ichiro Matsumoto^b ; Kiyoshi Fukuhara^a ; ^{fukuhara@pharm.showa-u.ac.jp}
• 关键词：Proanthocyanidin ; Catechin ; Arteriosclerosis LOX-1 ; Radical scavenging activity
• 刊名：Bioorganic & Medicinal Chemistry Letters
• 出版年：2017
• 出版时间：15 February 2017
• 年：2017
• 卷：27
• 期：4
• 页码：1041-1044
• 全文大小：702 K
• 卷排序：27

文摘

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.