Enhanced radical scavenging activity of a procyanidin B3 analogue comprised of a dimer of planar catechin |
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Authors: | Mirei Mizuno Ikuo Nakanishi Ken-ichiro Matsumoto Kiyoshi Fukuhara |
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Institution: | 1. School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan;2. Quantitative RedOx Sensing Team (QRST), Department of Basic Medical Sciences for Radiation Damages, National Institute of Radiological Sciences (NIRS), Inage-ku, Chiba 263-8555, Japan |
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Abstract: | 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. |
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Keywords: | OxLDL oxidized low-density lipoprotein LOX-1 lectin-like oxidized low-density lipoprotein receptor LDL low-density lipoprotein ROS reactive oxygen species NF-κB nuclear factor-kappa B DDQ galvinoxyl radical MeCN acetonerile Proanthocyanidin Catechin Arteriosclerosis LOX-1 Radical scavenging activity |
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