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Molecules 2015, 20(2), 3290-3308;

Study of Coumarin-Resveratrol Hybrids as Potent Antioxidant Compounds

CIQUP/Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, 4169-007 Porto, Portugal
Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain
Departamento de Química Inorgánica y Analítica, Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Casilla 233 Santiago, Chile
These authors contributed equally to this work.
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 13 January 2015 / Revised: 11 February 2015 / Accepted: 12 February 2015 / Published: 16 February 2015
(This article belongs to the Section Medicinal Chemistry)
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In the present work we synthesized a selected series of hydroxylated 3-phenylcoumarins 58, with the aim of evaluating in detail their antioxidant properties. From an in depth study of the antioxidant capacity data (ORAC-FL, ESR, CV and ROS inhibition) it was concluded that these derivatives are very good antioxidants, with very interesting profiles in all the performed assays. The study of the effect of the number and position of the hydroxyl groups on the antioxidant activity was the principal aim of this study. In particular, 7-hydroxy-3-(3'-hydroxy)phenylcoumarin (8) proved to be the most active and effective antioxidant of the selected series in four of the performed assays (ORAC-FL = 11.8, capacity of scavenging hydroxyl radicals = 54%, Trolox index = 2.33 and AI30 index = 0.18). However, the presence of two hydroxyl groups on this molecule did not increase greatly the activity profile. Theoretical evaluation of ADME properties of all the derivatives was also carried out. All the compounds can act as potential candidates for preventing or minimizing the free radical overproduction in oxidative-stress related diseases. These preliminary findings encourage us to perform a future structural optimization of this family of compounds. View Full-Text
Keywords: hydroxylated 3-phenylcoumarins; antioxidant assays; electrochemical study; inhibition of ROS; ESR; ADME properties hydroxylated 3-phenylcoumarins; antioxidant assays; electrochemical study; inhibition of ROS; ESR; ADME properties

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Matos, M.J.; Mura, F.; Vazquez-Rodriguez, S.; Borges, F.; Santana, L.; Uriarte, E.; Olea-Azar, C. Study of Coumarin-Resveratrol Hybrids as Potent Antioxidant Compounds. Molecules 2015, 20, 3290-3308.

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