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Inhibitory Effects of Resveratrol Analogs on Mushroom Tyrosinase Activity
NIQUA, Federal University of Juiz de Fora, Juiz de Fora, Minas Gerais 36036-900, Brazil
Department of Chemistry, I.C.E., Federal University of Juiz de Fora, Campus Universitário, Juiz de Fora, Minas Gerais 36036-900, Brazil
* Authors to whom correspondence should be addressed.
Received: 26 July 2012; in revised form: 28 September 2012 / Accepted: 30 September 2012 / Published: 9 October 2012
Abstract: Skin pigmentation disorders typically involve an overproduction or uneven distribution of melanin, which results in skin spots. Resveratrol can inhibit tyrosinase, the active enzyme in the synthesis of melanin, but it does not inhibit the synthesis of melanin to an extent that enables its use alone as a skin whitening agent in pharmaceutical formulations, so its use as a coadjuvant in treatment of hyperpigmentation is suggested. Six resveratrol analogs were tested for tyrosinase inhibitory activity in vitro. Among the analogs tested, compound D was the most powerful tyrosinase inhibitor (IC50 = 28.66 µg/mL), two times more active than resveratrol (IC50 = 57.05 µg/mL), followed by the analogs A, E, B, F and C, respectively. This demonstrated that the hydroxylation at C4' on the phenolic ring was the molecular modification with most importance for the observed activity.
Keywords: chemical synthesis; mushroom tyrosinase activity; structure-activity; tyrosinase; activity in vitro
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Zimmermann Franco, D.C.; Gonçalves de Carvalho, G.S.; Rocha, P.R.; da Silva Teixeira, R.; da Silva, A.D.; Barbosa Raposo, N.R. Inhibitory Effects of Resveratrol Analogs on Mushroom Tyrosinase Activity. Molecules 2012, 17, 11816-11825.
Zimmermann Franco DC, Gonçalves de Carvalho GS, Rocha PR, da Silva Teixeira R, da Silva AD, Barbosa Raposo NR. Inhibitory Effects of Resveratrol Analogs on Mushroom Tyrosinase Activity. Molecules. 2012; 17(10):11816-11825.
Zimmermann Franco, Danielle Cristina; Gonçalves de Carvalho, Gustavo Senra; Rocha, Paula Rafaela; da Silva Teixeira, Raquel; da Silva, Adilson David; Barbosa Raposo, Nádia Rezende. 2012. "Inhibitory Effects of Resveratrol Analogs on Mushroom Tyrosinase Activity." Molecules 17, no. 10: 11816-11825.