Polyphenols as superoxide dismutase modulators and ligands for estrogen receptors

Vincent Farines (1) , Marie-Carmen Monje (1) , Joao Paulo Telo (2) , Edouard Hnawia (3) , Michel Sauvain (1) , Françoise Nepveu (1)

1 PHARMA-DEV - Pharmacochimie et Biologie pour le Développement
2 IST - Instituto Superior Técnico, Universidade Técnica de Lisboa
3 UNC - Université de la Nouvelle-Calédonie

The capacity of estrogen and stilbene derivatives to modulate the activity of superoxide dismutases in relation with their estrogenic properties has been studied. The properties of trans-resveratrol (3,5,4′-trihydroxystilbene) and its analogues, 4-hydroxystilbene, 4,4′-dihydroxystilbene, 3,5-dihydroxystilbene, 3,5,4′-trimethoxystilbene and 4,4′-dihydroxy-3,5,3′,5′-tetramethylstilbene were compared to 17β-estradiol and its analogues (2-methoxyestradiol, estrone, 2-hydroxyestradiol and 2-methoxyestrone). Measurement of estrogen receptor-β (ER-β) binding capacity was carried out by a receptor competitor assay associated with fluorescence polarisation detection. The superoxide dismutase (SOD) modulation activity was followed with a spectrophotometric assay using the sequence xanthine/xanthine oxidase-2,3-bis[2-methoxy-4-nitro-sulfo-phenyl]-2H-tetrazolium-5-carboxanilide (X/XO-XTT). The structure–activity relationship was different for the two series tested. In the estrogenic series, a compound which does not inhibit SOD, is recognized by the ER-β. In contrast for the stilbenic series both properties are parallel each other.

Mots clés: Estrogen; Stilbenic derivatives; Resveratrol; Superoxide dismutase inhibitors; Estrogen receptor β; Polyphenols

Domaines: Génie chimique; Génie des procédés

Vincent Farines, Marie-Carmen Monje, Joao Paulo Telo, Edouard Hnawia, Michel Sauvain, et al.. Polyphenols as superoxide dismutase modulators and ligands for estrogen receptors. Analytica Chimica Acta, 2004, 513 (1), pp.103-111. ⟨10.1016/j.aca.2003.08.065⟩. ⟨hal-02134662⟩