Synthesis and pancreatic lipase inhibition activity evaluation of aurone derivatives with substituents on benzylidene ring

Abstract

Pancreatic lipase is an essential enzyme for the digestion and absorption of dietary fat. Inhibiting this enzyme is one of the strategies in tackling obesity. To date, orlistat is the only Food and Drug Administration (FDA)-approved drug for obesity treatment via this mechanism. Therefore, there has been a growing interest in exploring novel compounds with natural structural frameworks that can give similar activity with fewer side effects. In this study, we describe the synthesis and pancreatic lipase inhibitory activity evaluation of 10 aurone derivatives with different substituents on the benzylidene ring. Aurone derivatives were synthesised through aldol condensation of benzofuranone and corresponding benzaldehyde derivatives with medium to good yields (45-73%). Pancreatic lipase inhibitory activities of synthesized compounds were determined by UV-Vis spectroscopy with quercetin and orlistat as references. Three aurones were found to have higher I% than quercetin at the same concentration (50 μg/ml). Compound 5c (2-(5’bromo-2’-hydroxybenzylidene)benzofuran-3(2H)-one) exhibited the greatest activity (I%=60.95%), better than quercetin (I%=27.20%) at the concentration of 50 μg/ml.