[Lipophilic derivatives of caffeic acid as lipoxygenase inhibitors with antioxidant properties].
We have prepared two lipophilic derivatives of caffeic acid at the carboxylic function--caffeic acid phenethyl ester, an active component of propolis, and N,N'-dicyclohexyl-O-(3,4-dihydroxycinnamoyl)-isourea. Both substances inhibit barley 5-lipoxygenase and soybean 15-lipoxygenase at micromolar concentrations. The inhibition is uncompetitive, dose-dependent and reversible. The caffeic acid derivatives also exhibit antioxidant properties and at a concentration 5-10 microM completely block the production of the reactive oxygen species in human neutrophils and in the cell-free xanthine/xanthine oxidase system.
Mirzoeva
O K
OK
Sud'ina
G F
GF
Pushkareva
M A
MA
Korshunova
G A
GA
Sumbatian
N V
NV
Varfolomeev
S D
SD
D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology*; D002109:Caffeic Acids / Q000737:chemistry / Q000494:pharmacology*; D002474:Cell-Free System; D001467:Hordeum / Q000201:enzymology; D006801:Humans; D008055:Lipids / Q000737:chemistry*; D016859:Lipoxygenase Inhibitors / Q000737:chemistry / Q000494:pharmacology*; D010626:Phenylethyl Alcohol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D017382:Reactive Oxygen Species; D013025:Glycine max / Q000201:enzymology; D014508:Urea / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology
D000975:Antioxidants; D002109:Caffeic Acids; D008055:Lipids; D016859:Lipoxygenase Inhibitors; C093481:N,N'-dicyclohexyl-O-(3,4-dihydroxycinnamoyl)isourea; D017382:Reactive Oxygen Species; D014508:Urea; C055494:caffeic acid phenethyl ester; D010626:Phenylethyl Alcohol