Synthesis and evaluation of berberine derivatives and analogs as potential antiacetylcholinesterase and antioxidant agents

Publication date: December 2016 Source:Phytochemistry Letters, Volume 18 Author(s): Mariagrazia Roselli, Maria Maddalena Cavalluzzi, Claudio Bruno, Angelo Lovece, Alessia Carocci, Carlo Franchini, Solomon Habtemariam, Giovanni Lentini Two known berberine derivatives and novel N-benzyl phenethylamines as open models of berberine were synthesized and evaluated as acetylcholinesterase (AChE) inhibitors and antioxidant agents. While being less potent than the parent compound (IC50 =0.70±0.04μM), both berberine derivatives performed as good AChE inhibitors (IC50 =2.30±0.29μM and 7.8±0.8μM, respectively) and were at least 36 and four times more potent than berberine as radical scavengers. Among the synthesized compounds, demethyleneberberine bromide (2) was the most interesting because it showed both anticholinesterase and radical scavenging activities with the lowest IC50 values. As expected, catechol rings appeared as fundamental for antioxidant properties. Indeed, the most active scavenging compound in the simplified analog series was the one bearing two catechol moieties, which displayed higher potency than gallic acid. Graphical abstract

Source: Phytochemistry Letters - October 14, 2016 Category: Chemistry Source Type: research