Synthesis and Tyrosinase Inhibitory Activity of Monoterpenoid Esters
Tyrosinase Inhibitory Activity of Monoterpenoid Esters
Keywords:
Tyrosinase inhibitory activity, Monoterpenoid esters, trans-Cinnamic acid, Monoterpenoids, EsterificationAbstract
Monoterpenoids are recognized as potent tyrosinase inhibitors to reduce the production of melanin. The structural modification of monoterpenoids into monoterpenoid esters is a potential approach for developing novel tyrosinase inhibitors that enhance the activity more effectively. This study aimed at assessing the potential tyrosinase inhibitory activity of monoterpenoid esters compared to kojic acid as a positive control using the dopachrome method. Ten monoterpenoid esters were synthesized by esterification of trans-cinnamic acid with monoterpenoids using triphenylphosphine and carbontetrabromide as reagents. The desired products were obtained in 5−64% yields. All synthesized monoterpenoid esters were further examined for their tyrosinase inhibitory activity. The results found that hinokitiol cinnamate was the most potent inhibitor of tyrosinase, with an IC50 value of 1.58±0.09 μM. These results indicated that hinokitiol cinnamate could represent tyrosinase inhibitor 9-fold more efficiently than kojic acid. Notably, this compound has the potential for the development of a new skin whitening agent for use in cosmetic ingredients.
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