Abstract
The antioxidant activity of 4-hydroxycoumarin synthetic derivatives and 4-methylumbelliferone were determined taking 4-hydroxycoumarin as the reference compound. Six 3-aryl-4-hydroxycoumarin derivatives were synthesized from 4-hydroxycoumarin as precursor in order to evaluate changes in their antioxidant properties due to C3-aryl substituent nature. Free radical scavenging capacities of these compounds against two different species DPPH(·) and ABTS(·+) and the protecting ability towards the β-carotene-linoleic acid co-oxidation enzymatically induced by lipoxygenase were measured. In addition, the relationship between the activities of these molecules against DPPH radical and the bond dissociation energy of O-H (BDE) calculated using methods of computational chemistry was evaluated.
Copyright © 2011 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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4-Hydroxycoumarins / chemical synthesis
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4-Hydroxycoumarins / chemistry*
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4-Hydroxycoumarins / pharmacology*
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Antioxidants / chemical synthesis
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Antioxidants / chemistry*
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Antioxidants / pharmacology*
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Benzothiazoles / metabolism
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Biphenyl Compounds / metabolism
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Enzyme Inhibitors / chemical synthesis
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Enzyme Inhibitors / chemistry
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Enzyme Inhibitors / pharmacology
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Free Radical Scavengers / chemical synthesis
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Free Radical Scavengers / chemistry
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Free Radical Scavengers / pharmacology
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Lipoxygenase / metabolism
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Oxidation-Reduction
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Picrates / metabolism
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Structure-Activity Relationship
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Sulfonic Acids / metabolism
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Thermodynamics
Substances
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4-Hydroxycoumarins
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Antioxidants
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Benzothiazoles
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Biphenyl Compounds
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Enzyme Inhibitors
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Free Radical Scavengers
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Picrates
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Sulfonic Acids
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2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid
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1,1-diphenyl-2-picrylhydrazyl
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Lipoxygenase