Whole Cell-mediated Biocatalytic Synthesis of Helicid Cinnamylate and Its Biological Evaluation as a Novel Tyrosinase Inhibitor
Tyrosinase inhibitors are clinically effective for treating some dermatological disorders related to melanin hyperpigmentation. Accordingly, the discovery and development of tyrosinase inhibitors have great value in the pharmaceutical and cosmetic industry. Here, a novel tyrosinase inhibitor, 6′-O-cinnamoyl-helicid (helicid cinnamylate) was successfully synthesized by a simple and effective biocatalytic approach with Aspergillus oryzae cells. Investigation of the effects of several key variables on helicid cinnamylate synthesis found that the reaction conversion, reaction rate and regioselectivity reached 99%, 9.40 mM/h and > 99%, respectively, at the optimal conditions with anhydrous acetone as the solvent, whole-cell concentration of 40 mg/mL, and the molar ratio of vinyl cinnamate to helicid of 10 at 45°C. The whole-cells retained 68.87% of its initial activity after reusing for seven batches, indicating a potent application potential in non-aqueous biocatalytic systems. It was worth noting that helicid cinnamylate demonstrated a more potent tyrosinase inhibitory activity with an IC 50 value of 3.55 mM than helicid (IC 50 = 4.48 mM) and arbutin (IC 50 = 5.48 mM), which suggest that helicid cinnamylate could be developed as a more potential tyrosinase inhibitor. In conclusion, this study provides a novel whole-cell catalytic approach for the synthesis of helicid cinnamylate and insight into its application as a tyrosinase inhibitor.
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