Comparative study of antioxidant and antimicrobial activity of berberine-derived Schiff bases, nitro-berberine and amino-berberine

In recent years, the scientific community has focused on traditional natural products and their potential therapeutic benefits. Berberine is a plant-derived isoquinoline alkaloid with a variety of biological properties and identified as a promising pharmacophore for discovering new therapeutic agents against various diseases. However, unfavorable pharmacokinetic properties of berberine have limited its clinical application so much that researchers pursue its structure modification to overcome this problem. This study focuses on the synthesis of new berberine derivatives to improve its antioxidant and antimicrobial potentials, which were characterized using CHNO and NMR instruments. Berberine extracted from barberry root was nitrated, reduced to amine and condensed with benzaldehyde derivatives to produce berberine-based Schiff bases. The H atom donating ability of all compounds was measured against DPPH free radicals, with IC(50) values ranging from 18.28 to 108.20 μg ml(−1). All berberine-based Schiff bases exhibited stronger antioxidant activity than nitro-berberine and amino-berberine. Only Schiff base derived from 4-hydroxybenzaldehyde showed slightly better antioxidant effects than original berberine. The inhibitory effects of the synthesized compounds were evaluated against important pathogenic fungal and bacterial strains using disk diffusion assays, with inhibition zone diameters ranging from 8.36 to 25.48 μg ml(−1). Berberine itself only affected Candida albicans fungus. Nitrated berberine was effective against all microorganisms except Gram-negative Acinetobacter baumannii. The results suggest that structural modifications and functionalization can enhance the antimicrobial and antioxidant properties of berberine.