Inhibitory activity of flavonoids from Prunus davidiana and other flavonoids on total ROS and hydroxyl radical generation.
Since reactive oxygen species (ROS) and hydroxyl radicals (*OH) play an important role in the pathogenesis of many human degenerative diseases, much attention has focused on the development of safe and effective antioxidants. Preliminary experiments have revealed that the methanol (MeOH) extract of the stem of Prunus davidiana exerts inhibitory/scavenging activities on 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals, total ROS and peroxynitrites (ONOO-). In the present study, the antioxidant activities of this MeOH extract and the organic solvent-soluble fractions, dichloromethane (CH2Cl2), ethyl acetate (EtOAc), and n-butanol (n-BuOH), and the water layer of P. davidiana stem were evaluated for the potential to inhibit *OH and total ROS generation in kidney homogenates using 2',7'-dichlorodihydrofluorescein diacetate (DCHF-DA), and for the potential to scavenge authentic ONOO-. We also evaluated the inhibitory activity of seven flavonoids isolated from P. davidiana stem, kaempferol, kaempferol 7-O-beta-D-glucoside, (+)-catechin, dihydrokaempferol, hesperetin 5-O-beta-D-glucoside, naringenin and its 7-O-beta-D-glucoside, on the total ROS, *OH and ONOO- systems. For the further elucidation of the structure-inhibitory activity relationship of flavonoids on total ROS and *OH generation, we measured the antioxidant activity of sixteen flavonoids available, including three active flavonoids isolated from P. davidiana, on the total ROS and *OH systems. We found that the inhibitory activity on total ROS generation increases in strength with more numerous hydroxyl groups on their structures. Also, the presence of an ortho-hydroxyl group, whether on the A-ring or B-ring, and a 3-hydroxyl group on the C-ring increased the inhibitory activity on both total ROS and *OH generation.
Jung
Hyun Ah
HA
Faculty of Food Science and Biotechnology, Pukyong National University, Busan 608-737, Korea.
Jung
Mee Jung
MJ
Kim
Ji Young
JY
Chung
Hae Young
HY
Choi
Jae Sue
JS
D020001:1-Butanol / Q000737:chemistry / Q000494:pharmacology; D000085:Acetates / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D001205:Ascorbic Acid / Q000494:pharmacology; D001713:Biphenyl Compounds / Q000037:antagonists & inhibitors / Q000378:metabolism; D002392:Catechin / Q000494:pharmacology; D002839:Chromans / Q000494:pharmacology; D004353:Drug Evaluation, Preclinical; D005419:Flavonoids / Q000037:antagonists & inhibitors* / Q000737:chemistry / Q000302:isolation & purification; D016166:Free Radical Scavengers / Q000737:chemistry / Q000494:pharmacology; D006569:Hesperidin / Q000031:analogs & derivatives* / Q000494:pharmacology; D006834:Hydrazines / Q000037:antagonists & inhibitors / Q000378:metabolism; D017665:Hydroxyl Radical / Q000037:antagonists & inhibitors / Q000378:metabolism*; D044949:Kaempferols / Q000494:pharmacology; D007668:Kidney / Q000166:cytology / Q000187:drug effects / Q000378:metabolism; D008297:Male; D000432:Methanol / Q000737:chemistry / Q000494:pharmacology; D008752:Methylene Chloride / Q000737:chemistry / Q000494:pharmacology; D010396:Penicillamine / Q000494:pharmacology; D030421:Peroxynitrous Acid / Q000037:antagonists & inhibitors / Q000378:metabolism; D010851:Picrates; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology; D018547:Plant Stems; D027861:Prunus / Q000737:chemistry; D051381:Rats; D017208:Rats, Wistar; D017382:Reactive Oxygen Species / Q000037:antagonists & inhibitors / Q000378:metabolism*; D013329:Structure-Activity Relationship; D014867:Water / Q000737:chemistry / Q000494:pharmacology
D000085:Acetates; D000975:Antioxidants; D001713:Biphenyl Compounds; D002839:Chromans; D005419:Flavonoids; D016166:Free Radical Scavengers; D006834:Hydrazines; D044949:Kaempferols; D010851:Picrates; D010936:Plant Extracts; D017382:Reactive Oxygen Species; D014867:Water; D030421:Peroxynitrous Acid; D017665:Hydroxyl Radical; D008752:Methylene Chloride; C069231:hesperetin 5-O-glucoside; C007650:ethyl acetate; D020001:1-Butanol; D002392:Catechin; C004931:1,1-diphenyl-2-picrylhydrazyl; D006569:Hesperidin; D010396:Penicillamine; D001205:Ascorbic Acid; C010643:6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid; D000432:Methanol