Titre du document / Document title

Structure-activity relationship and classification of flavonoids as inhibitors of xanthine oxidase and superoxide scavengers

Auteur(s) / Author(s)

COS P. ⁽¹⁾ ; YING L. ⁽¹⁾ ; CALOMME M. ⁽¹⁾ ; HU J. P. ⁽¹⁾ ; CIMANGA K. ⁽¹⁾ ; VAN POEL B. ⁽¹⁾ ; PIETERS L. ⁽¹⁾ ; VLIETINCK A. J. ⁽¹⁾ ; BERGHE D. V. ⁽¹⁾ ;

Affiliation(s) du ou des auteurs / Author(s) Affiliation(s)

⁽¹⁾ Department of Pharmaceutical Sciences, University ofAntwerp, Universiteitsplein 1, 2610 Antwerp, BELGIQUE

Résumé / Abstract

The structure-activity relationship of flavonoids as inhibitors of xanthine oxidase and as scavengers of the superoxide radical, produced by the action of the enzyme xanthine oxidase, was investigated. The hydroxyl groups at C-5 and C-7 and the double bond between C-2 and C-3 were essential for a high inhibitory activity on xanthine oxidase. Flavones showed slightly higher inhibitory activity than flavonols. All flavonoid derivatives except isorhamnetin (30) were less active than the original compounds. For a high superoxide scavenging activity on the other hand, a hydroxyl group at C-3' in ring B and at C-3 were essential. According to their effect on xanthine oxidase and as superoxide scavengers, the flavonoids could be classified into six groups: superoxide scavengers without inhibitory activity on xanthine oxidase (category A), xanthine oxidase inhibitors without any additional superoxide scavenging activity (category B), xanthine oxidase inhibitors with an additional superoxide scavenging activity (category C), xanthine oxidase inhibitors with an additional pro-oxidant effect on the production of superoxide (category D), flavonoids with a marginal effect on xanthine oxidase but with a pro-oxidant effect on the production of superoxide (category E), and finally, flavonoids with no effect on xanthine oxidase or superoxide (category F).

Revue / Journal Title

Journal of natural products   ISSN 0163-3864   CODEN JNPRDF 

Source / Source

1998, vol. 61, n^o1, pp. 71-76 (14 ref.)

Langue / Language

Anglais

Editeur / Publisher

American Chemical Society, Washington, DC, ETATS-UNIS  (1979) (Revue)

Mots-clés anglais / English Keywords

Structure activity relation ; Flavonoid ; Phenols ; Polyphenol ; Enzyme inhibitor ; Xanthine oxidase ; In vitro ; Radical scavenger ; Hyperoxides ; Natural product ; Plant origin ; Pharmacognosy ; Synthetic product ; Oxidoreductases ; Enzyme ;

Mots-clés français / French Keywords

Relation structure activité ; Flavonoïde ; Phénols ; Polyphénol ; Inhibiteur enzyme ; Xanthine oxidase ; In vitro ; Intercepteur radical ; Hyperoxyde ; Produit naturel ; Origine végétale ; Pharmacognosie ; Produit synthétique ; 1-Benzopyrane dérivé ; Flavone dérivé ; Oxidoreductases ; Enzyme ;

Mots-clés espagnols / Spanish Keywords

Relación estructura actividad ; Flavonoide ; Fenoles ; Polifenol ; Inhibidor enzima ; Xanthine oxidase ; In vitro ; Interceptor radical ; Hiperóxido ; Producto natural ; Origen vegetal ; Farmacognosia ; Producto sintético ; Oxidoreductases ; Enzima ;

Localisation / Location

INIST-CNRS, Cote INIST : 4127, 35400007829840.0130