Facile synthesis of tetrahydroprotoberberine and protoberberine alkaloids from protopines and study on their antibacterial activities

Abstract

A series of isoquinoline alkaloids including tetrahydroprotoberberines, N-methyl tetrahydroprotoberberines and protoberberines were facile synthesised with protopines as the starting material. All compounds were evaluated for their antibacterial activities against four pathogenic bacteria Escherichia coli, Staphyloccocus aureus, Staphylococcus gallinarum and Salmonella choleraesuis. Experimental results indicated that protoberberines were the most active compounds to the target bacteria among the tested alkaloids. It was suggested that planar molecule with high aromatisation level (e.g. coptisine 5 and berberine 6) or a positive charge of the molecules (e.g. N-methyl tetrahydroprotoberberines 11 and 12) had a positive influence on the antibacterial effects.