2. Academic Validation
  3. Synthesis and antioxidant activity of a procyanidin B3 analogue

Synthesis and antioxidant activity of a procyanidin B3 analogue

  • Bioorg Med Chem Lett. 2017 Feb 15;27(4):1041-1044. doi: 10.1016/j.bmcl.2016.12.067.
Mirei Mizuno 1,  Ikuo Nakanishi 2,  Satoko Matsubayashi 1,  Kohei Imai 1,  Takuya Arai 3,  Ken-Ichiro Matsumoto 2,  Kiyoshi Fukuhara 4
Affiliations

Affiliations

  • 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.
  • 3 School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan; Graduate School of Pharmaceutical Sciences, Nagoya City University, 3-1 Tanabe-dori, Mizuho-ku, Nagoya, Aichi 467-8603, Japan.
  • 4 School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan. Electronic address: fukuhara@pharm.showa-u.ac.jp.
PMID: 28082039 DOI: 10.1016/j.bmcl.2016.12.067
Abstract

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.

Keywords

Arteriosclerosis LOX-1; Catechin; Proanthocyanidin; Radical scavenging activity.

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