Synthesis and Evaluation of in vitro Antibacterial Properties of Secoisolariciresinol Diglucoside

Abstract

In the present study, Secoisolariciresinol diglucoside (SDG) was synthesized from commercially available 3,4-dimethoxytoluene, butanediol and penta acetyl glucose. This includes bromination, alkylation, glycosylation, deacetylation and demethylation reactions to yield the interested title compound (SDG), further the assignment of the chemical structure of the synthetic SDG was performed with IR, MS-TOF, 1H and 13C NMR. The antibacterial property of the synthetic SDG was investigated against seven different Gram positive and Gram negative bacteria. The results of the present study proved that SDG can be obtained with good yield (56.2%) under this scheme. Moreover, it exerts an exceptional antibacterial activity where it showed maximum zone of inhibition with 30 and 27.3 mm against E. coli and minimum 7 and 6.1 mm against S. pyogens and S. typhimurium in agar well and disk diffusion respectively. It also showed maximum activity (18 mm at MIC 200 ppm) against S. typhimurium, while minimum inhibitory activity was 4 mm with MIC at 300 ppm against S. pyogens. The scheme of synthesis was found to be an efficient method and the synthetic SDG was also proved to possess a broad spectrum of activity against a panel of bacteria responsible for causing most common diseases.