Research Information System
Journal of Molecular Structure, vol.1365, 2026 (SCI-Expanded, Scopus)
Rosmarinic acid (RA), a natural polyphenolic compound containing catechol moieties, was structurally modified through esterification to investigate its potential as a tyrosinase inhibitor and anti-browning agent. Five alkyl ester derivatives were synthesized and characterized using spectroscopic techniques. Their inhibitory activities against mushroom tyrosinase were evaluated through enzyme kinetics, copper-chelation assays, and molecular docking studies to elucidate the mechanism of action. Among the synthesized derivatives, RA-2 exhibited the most potent inhibitory activity, demonstrating enhanced interaction with the binuclear copper active site compared to the parent compound. Kinetic analysis revealed a mixed-type inhibition mechanism, while computational studies supported stable binding within the catalytic pocket. Furthermore, anti-browning experiments confirmed the practical effectiveness of the most active derivative in suppressing enzymatic browning. The results indicate that rational esterification of rosmarinic acid improves tyrosinase inhibitory activity by modulating lipophilicity without disrupting the catechol pharmacophore. This study provides a preliminary structure–activity insight and highlights rosmarinic acid ester derivatives as promising candidates for applications in food preservation and cosmetic formulations targeting hyperpigmentation.