Characterization of antioxidant, α-glucosidase and tyrosinase inhibitors from the rhizomes of Potentilla anserina L. and their structure–activity relationship

• Bioactive phytochemicals of the rhizomes of Potentilla anserina L. were conducted. • Five new flavonoids were isolated from the rhizomes of Potentilla anserina L.. • Compounds 4 and 14 had good antioxidant and α -glucosidase inhibitory effects. • Compounds 4 and 14 were potent competitive anti-browning inhibitors. • Hydrogen binding and π-alkyl binding in the two compounds were responsible for the anti-tyrosinase action. Five new flavonoids ( 1 – 5 ), along with 25 known compounds, were isolated from the rhizomes of Potentilla anserina L. and their structures were identified using spectroscopic and chemical evidence. The extract, all fractions, and all isolated compounds were evaluated for their antioxidant, α -glucosidase, and tyrosinase inhibitory activities, and their structure–activity relationship was interpreted. The biflavanols and quercetin-3- O - α - l -rhamnopyranoside-2″-gallate ( 14) exhibited significant antioxidant and α -glucosidase inhibition activities. In this study, anti-tyrosinase activity and its mechanism of active compounds (potenserin C ( 4) , potenserin D ( 5), and quercetin-3- O - α - l -rhamnopyranoside-2 ″ -gallate ( 14)) were explored by a combination of computational simulations and kinetic studies. Kinetic studies indicated that potenserin C ( 4) and quercetin-3- O - α - l -rhamnopyranoside-2 ″ -gallate ( 14) inhibited tyrosinase in a competitive manner, whereas potenserin D ( 5) acted in a reversible noncompetitive manner. The molecular docking result indicated that the substitution of the glucose moiety with galloyl and the presence of 3 ′ , 4 ′ , 5 ′ -OH in flavonoid aglycones played a crucial role for the tyrosinase inhibiting effect. Moreover, the presence of biflavanols increased the activity against tyrosinase because of strong hydrogen binding, π-alkyl binding, and electrostatic interaction. Thus, the presented experiments developed several new lead compounds that could act as antioxidants and α -glucosidase inhibitors. Furthermore, biflavanols and quercetin-3- O - α - l -rhamnopyranoside-2 ″ -gallate played important roles in the anti-browning activity during food processing.