Abstract
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.
MeSH terms
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Antioxidants / chemistry
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Antioxidants / pharmacology*
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Caffeic Acids / chemistry
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Caffeic Acids / pharmacology*
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Cell-Free System
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Glycine max / enzymology
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Hordeum / enzymology
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Humans
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Lipids / chemistry*
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Lipoxygenase Inhibitors / chemistry
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Lipoxygenase Inhibitors / pharmacology*
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Phenylethyl Alcohol / analogs & derivatives*
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Phenylethyl Alcohol / chemistry
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Phenylethyl Alcohol / pharmacology
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Reactive Oxygen Species
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Urea / analogs & derivatives*
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Urea / chemistry
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Urea / pharmacology
Substances
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Antioxidants
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Caffeic Acids
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Lipids
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Lipoxygenase Inhibitors
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N,N'-dicyclohexyl-O-(3,4-dihydroxycinnamoyl)isourea
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Reactive Oxygen Species
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Urea
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caffeic acid phenethyl ester
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Phenylethyl Alcohol