Structural requirements of flavonoids for inhibition of protein glycation and radical scavenging activities.
To clarify the structural requirements of flavonoids for formation of advanced glycation end-products (AGEs), various flavonoids were examined. The results suggested the following structural requirements of flavonoids for the inhibition of AGEs formation: (1). as the hydroxyl groups at the 3'-, 4'-, 5-, and 7-positions increased in number, the inhibitory activities became stronger; (2). the activities of flavones were stronger than those of corresponding flavonols, flavanones, and isoflavones; (3). methylation or glucosylation of the 4'-hydroxyl group of flavones, flavonols, and flavanones reduced activity; (4). methylation or glycosylation of the 3-hydroxyl group of flavonols tended to increase activity; (5). glycosylation of the 7-hydroxyl group of flavones and isoflavones reduced activity. In addition, various flavonoids with strong AGEs formation inhibitory activity tended to exhibit strong scavenging activity for 1,1-diphenyl-2-picrylhydrazyl and superoxide anion radicals, with several exceptions.
Matsuda
Hisashi
H
Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, 2Kyoto 607-8412, Japan.
Wang
Tao
T
Managi
Hiromi
H
Yoshikawa
Masayuki
M
D001713:Biphenyl Compounds; D005419:Flavonoids / Q000737:chemistry* / Q000494:pharmacology; D016166:Free Radical Scavengers; D005609:Free Radicals / Q000737:chemistry; D017127:Glycation End Products, Advanced / Q000037:antagonists & inhibitors*; D006031:Glycosylation; D008745:Methylation; D015394:Molecular Structure; D010851:Picrates / Q000737:chemistry; D013481:Superoxides / Q000737:chemistry
D001713:Biphenyl Compounds; D005419:Flavonoids; D016166:Free Radical Scavengers; D005609:Free Radicals; D017127:Glycation End Products, Advanced; D010851:Picrates; D013481:Superoxides; C004931:1,1-diphenyl-2-picrylhydrazyl