Synthesized depsides were modified based on the core structure of jaboticabin, to enhance its biological activities. Desired depsides were synthesized through an esterification with methyl 2-(2- hydroxyphenyl) acetate (NT0) and a carboxylic acid compound. DCC and DMAP were required to activate the carboxylic group and solvent used was DCM. 2-(2-Methoxy-2-oxoethyl)phenyl 3- nitrobenzoate (NT1) and 2-(2-methoxy-2-oxoethyl)phenyl (E)-3-(2,6-dichlorophenyl)acrylate (NT18) showed powerful anti ɑ-glucosidase activity with an IC50 value of 68.7 μM and 84.8 μM. The IC50 values obtained from assay were lower than that of Acarbose, the standard reference (IC50 = 93.6 μM). On the other hand, none of the compounds showed good potential towards antioxidant activities.