New polyhydroxylated flavon-3-ols and 3-hydroxy-2-styrylchromones: synthesis and ROS/RNS scavenging activities

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.