New polyhydroxylated flavon-3-ols and 3-hydroxy-2-styrylchromones: synthesis and ROS/RNS scavenging activities
authors Sousa, JLC; Proenca, C; Freitas, M; Fernandes, E; Silva, AMS
journal EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
author keywords Flavon-3-ols; 3-Hydroxy-2-styrylchromones; Reactive oxygen species; Reactive nitrogen species; Radical scavenging activity; Antioxidant activity
keywords ANTIOXIDANT ACTIVITY; HUMAN NEUTROPHILS; SINGLET OXYGEN; IN-VITRO; FLAVONOIDS; AGENTS; 3',4'-DIHYDROXYFLAVONOL; 2-STYRYLCHROMONES; ABILITY; INJURY
abstract New polyhydroxylated flavon-3-ols and 3-hydroxy-2-styrylchromones were prepared and assessed as reactive oxygen species (ROS) and reactive nitrogen species (RNS) scavengers. The synthetic strategy involved the preparation of 2'-hydroxychalcones and 2'-hydroxycinnamylidenoacetophenones from base-catalyzed aldol reaction of appropriate 2'-hydroxyacetophenones and benzaldehydes/cinnamaldehydes, followed by an Algar-Flynn-Oyamada (AFO) reaction to give the polyalkoxy(flavon-3-ols and 3-hydroxy-2-styrylchromones). The last step of this synthetic route consisted in the cleavage of the protecting groups affording the expected polyhydroxylated derivatives. The present work consisted in the study of the in vitro scavenging activities of the synthetized compounds against the most physiologically relevant ROS [superoxide radical (O-2(center dot-)), hydrogen peroxide (H2O2), hypochlorous acid (HOCl), singlet oxygen (O-1(2)) and peroxyl radical (ROO center dot)] and RNS [nitric oxide (center dot NO) and peroxynitrite anion (ONOO-)]. Generally, all the tested new polyhydroxylated flavon-3-ols and 3-hydroxy-2-styrylchromones exhibited scavenging effects dependent on the concentration, and with IC50 values found within the micromolar range. This work allowed the establishment of new structure activity relationships and brought the knowledge about the selective choice of a structure depending on the targeted reactive species. (C) 2016 Elsevier Masson SAS. All rights reserved.
publisher ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
issn 0223-5234
year published 2016
volume 119
beginning page 250
ending page 259
digital object identifier (doi) 10.1016/j.ejmech.2016.04.057
web of science category Chemistry, Medicinal
subject category Pharmacology & Pharmacy
unique article identifier WOS:000378433600017
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journal impact factor 4.816
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