title: Synthesis and antioxidant activity of a procyanidin B3 analogue.
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.
authors.affiliation: School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan.
authors.forename: Mirei
authors.initials: M
authors.lastname: Mizuno
authors.affiliation: 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.
authors.forename: Ikuo
authors.initials: I
authors.lastname: Nakanishi
authors.affiliation: School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan.
authors.forename: Satoko
authors.initials: S
authors.lastname: Matsubayashi
authors.affiliation: School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan.
authors.forename: Kohei
authors.initials: K
authors.lastname: Imai
authors.affiliation: 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.
authors.forename: Takuya
authors.initials: T
authors.lastname: Arai
authors.affiliation: 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.
authors.forename: Ken-Ichiro
authors.initials: KI
authors.lastname: Matsumoto
authors.affiliation: School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan. Electronic address: fukuhara@pharm.showa-u.ac.jp.
authors.forename: Kiyoshi
authors.initials: K
authors.lastname: Fukuhara
mesh_terms: D000818:Animals; D000975:Antioxidants / Q000494:pharmacology*; D044946:Biflavonoids / Q000737:chemistry* / Q000494:pharmacology*; D002392:Catechin / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D044945:Proanthocyanidins / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D000975:Antioxidants; D044946:Biflavonoids; D044945:Proanthocyanidins; C479581:procyanidin B3; D002392:Catechin
keywords: Arteriosclerosis LOX-1; Catechin; Proanthocyanidin; Radical scavenging activity