Novel Mannich bases of α- and γ-mangostins: Synthesis and evaluation of antioxidant and membrane-protective activity

• Published in: European journal of medicinal chemistry 2018-05, Vol.152, p.10-20
• Main Authors: Buravlev, Evgeny V., Shevchenko, Oksana G., Anisimov, Aleksei A., Suponitsky, Kyrill Yu
• Format: Article
• Language: English
• Subjects: Mannich bases; Membrane-protective activity; Oxidative hemolysis; α-Mangostin; γ-Mangostin
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2018.04.022

A series of new C-4- and C-4/C-5-aminomethyl derivatives were synthesized on the basis of α- and γ-mangostins. A comparative evaluation of their chelating ability, radical scavenging activity and hemolytic activity, as well as antioxidant and membrane-protective properties, was carried out on the model of H2O2-induced hemolysis of mammalian red blood cells. It was shown that γ-mangostin and its C-4/C-5-derivatives were superior to α-mangostin and its derivatives in all the investigated parameters characterizing the antioxidant activity in the test systems used. Most of the synthesized Mannich bases at low concentrations were superior to the original α- and γ-mangostins in the ability to protect mammalian red blood cells under H2O2-induced oxidative stress conditions. [Display omitted] •A series of novel Mannich bases of α- and γ-mangostins were synthesized.•Evaluation of synthesized products as oxidative process inhibitors was carried out.•The membrane-protective activity of products on red blood cells was determined.•Superiority of γ-mangostin relative to α-mangostin derivatives was established.