Novel Mannich Bases of α‐Mangostin Bearing Methoxyphenyl Moieties with Antioxidant and Membrane‐protective activity

Abstract

AbstractA series of novel Mannich bases containing (monomethoxy‐, dimethoxy‐ or trimethoxy)phenyl substituent and morpholine fragment have been synthesizedviaC‐4‐monoaminomethylation of α‐mangostin, a natural hydroxyxanthone. This modification has led to a considerable reduction in erythrotoxicity of natural xanthone while preserving its high antioxidant activity. All synthesized derivatives have demonstrated higher radical scavenging activity and total antioxidant activity compared to those of α‐mangostin, several compounds have also shown higher efficacy in the test system with red blood cells. In the model of oxidative hemolysis of red blood cells induced by hydrogen peroxide and 2,2’‐azobis(2‐amidinopropane) dihydrochloride, a Mannich base containing 3,4,5‐trimethoxyphenyl substituent has been shown to have the highest membrane‐protective and antioxidant activity.