In this manuscript, we synthesized a series of bergenin analogues, analyzed their structural importance for two biologic activities (anitioxidant activity (ORAC) and mushroom tyrosinase inhibitory activity). Among them, compound 5 which contains catechol moiety exhibited the most antioxidant activity (3.75 ${mu}mol$ of Trolox equiv. per ${mu}mol$ of 5). Furthermore, compound 5 was found to be the most potent ($IC_{50}$ value = $17.5{pm}0.04{mu}M$) when compared with the standard tyrosinase inhibitors of arbutin ($IC_{50}$ value = $221.8{pm}1.9{mu}M$) and kojic acid ($IC_{50}$ value = $46.6{pm}3.8{mu}M$). The bergenin moiety, the ester linkage, and benzoic acid moiety of bergenin derivatives affected two biologic activities. Tyrosinase inhibitory activity was affected by substituents of benzoic acid moiety. This manuscript provides a good foundation for the design and development of new tyrosinase inhibitors.