title: Effect of different C3-aryl substituents on the antioxidant activity of 4-hydroxycoumarin derivatives.
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.
authors.affiliation: INFIQC (CONICET), Dpto. Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, Córdoba 5000, Argentina.
authors.forename: Sergio A
authors.initials: SA
authors.lastname: Rodríguez
authors.forename: Mónica A
authors.initials: MA
authors.lastname: Nazareno
authors.forename: Maria T
authors.initials: MT
authors.lastname: Baumgartner
mesh_terms: D015110:4-Hydroxycoumarins / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D052160:Benzothiazoles / Q000378:metabolism; D001713:Biphenyl Compounds / Q000378:metabolism; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D008084:Lipoxygenase / Q000378:metabolism; D010084:Oxidation-Reduction; D010851:Picrates / Q000378:metabolism; D013329:Structure-Activity Relationship; D013451:Sulfonic Acids / Q000378:metabolism; D013816:Thermodynamics
chemical_list: D015110:4-Hydroxycoumarins; D000975:Antioxidants; D052160:Benzothiazoles; D001713:Biphenyl Compounds; D004791:Enzyme Inhibitors; D016166:Free Radical Scavengers; D010851:Picrates; D013451:Sulfonic Acids; C002502:2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid; C004931:1,1-diphenyl-2-picrylhydrazyl; D008084:Lipoxygenase