Inhibition of free radical-induced peroxidation of rat liver microsomes by resveratrol and its analogues.
Resveratrol (3,5,4'-trans-trihydroxystilbene) is a natural phytoalexin present in grapes and red wine, which possesses a variety of biological activities including antioxidative activity. To find more efficient antioxidants by structural modification, resveratrol analogues, that is, 3,4-dihydroxy-trans-stilbene (3,4-DHS), 4,4'-dihydroxy-trans-stilbene (4,4'-DHS), 4-hydroxy-trans-stilbene (4-HS) and 3,5-dihydroxy-trans-stilbene (3,5-DHS), were synthesized and their antioxidant activity studied for the free radical-induced peroxidation of rat liver microsomes in vitro. The peroxidation was initiated by either a water-soluble azo compound 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH) or Fe(2+)/ascorbate, and monitored by oxygen uptake and formation of thiobarbituric acid reactive substances (TBARS). It was found that all of these trans-stilbene derivatives are effective antioxidants against both AAPH- and iron-induced peroxidation of rat liver microsomes with an activity sequence of 3,4-DHS>4,4'-DHS>resveratrol>4-HS>3,5-DHS. The remarkably higher antioxidant activity of 3,4-DHS is discussed.
Cai
Yu Jun
YJ
National Laboratory of Applied Organic Chemistry, Lanzhou University, Gansu 730000, Lanzhou, China.
Fang
Jian Guo
JG
Ma
Lan Ping
LP
Yang
Li
L
Liu
Zhong Li
ZL
D000578:Amidines / Q000037:antagonists & inhibitors; D000818:Animals; D000975:Antioxidants / Q000494:pharmacology*; D001205:Ascorbic Acid / Q000037:antagonists & inhibitors; D015195:Drug Design; D005609:Free Radicals / Q000037:antagonists & inhibitors; D007700:Kinetics; D015227:Lipid Peroxidation / Q000187:drug effects*; D008862:Microsomes, Liver / Q000187:drug effects*; D015394:Molecular Structure; D010101:Oxygen Consumption; D051381:Rats; D000077185:Resveratrol; D013267:Stilbenes / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D017392:Thiobarbituric Acid Reactive Substances / Q000032:analysis
D000578:Amidines; D000975:Antioxidants; D005609:Free Radicals; D013267:Stilbenes; D017392:Thiobarbituric Acid Reactive Substances; C046728:2,2'-azobis(2-amidinopropane); D001205:Ascorbic Acid; D000077185:Resveratrol