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Effect of different C3-aryl substituents on the antioxidant activity of 4-hydroxycoumarin derivatives.

Bioorganic & medicinal chemistry (2011-10-04)
Sergio A Rodríguez, Mónica A Nazareno, Maria T Baumgartner
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
4-Methylumbelliferone, ≥98%
Sigma-Aldrich
4-Hydroxycoumarin, 98%

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