Novel molecular combination deriving from natural aminoacids and polyphenols: Design, synthesis and free-radical scavenging activities

Following the recent output of scientific publications in the matter of synergic activity between different antioxidants, we have undertaken the present study with the aim to synthesize new molecules with radical-scavengers activity based on the conjugation of bioactive portions (i.e. phenols, cysteine, methionine or tyrosine), characterized by different structures and mechanisms of action, to promote the simultaneous quenching of different radical species in the site of the oxidative damage. In this context, derivatives of phenolic acid, aminoacids and dopamine have been also prepared. The newly synthesized compounds were evaluated in vitro applying specific and complementary antioxidant test such as DPPH assay and ORAC test. As emerged from the evaluation, prerequisites for the activity of the synthesized molecules were: i) the maintenance of at least two hydroxylic groups on the aromatic moiety of phenolic portion, ii) the presence of a spacer between the aromatic moiety and the carbonilic group.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Poliphenol-aminoacid or poliphenol-aminoacid-dopamine conjugates were synthesized. ► Evaluation of the antioxidant capacity by means of DPPH and ORAC assays. ► Some of the new derivatives showed good antioxidant activity.