| Autor: |
Stiawan, Aris, Sholikhah, Eti Nurwening, Kurniawan, Yehezkiel Steven, Priastomo, Yoga, Jumina |
| Předmět: |
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| Zdroj: |
Journal of Chinese Pharmaceutical Sciences; Aug2021, Vol. 30 Issue 8, p634-644, 11p |
| Abstrakt: |
In this work, we studied the synthesis, cytotoxicity assay, and molecular docking of hydroxychalcone derivatives as tyrosinase inhibitors. Synthesis of chalcone derivatives was carried out through a Claisen-Schmidt condensation reaction between acetophenone and benzaldehyde derivatives under alkaline conditions for 48 h. The synthesized products were characterized by using Fourier transform infrared (FTIR), gas chromatography-mass spectrometry (GC-MS), proton and carbon nuclear magnetic resonance (1H and 13C NMR) spectrometer. The in vitro inhibitory activity was evaluated against tyrosinase enzyme by employing L-3,4-dihydroxyphenylalanine (L-DOPA) as the substrate. We successfully synthesized 4-hydroxychalcone (HC) and 4-hydroxy-3-methoxychalcone (HMC) with a yield of 60% and 76%, respectively. While the tyrosinase inhibitory test of HC and HMC gave the IC50 value of 64.35 and 21.56 µg/mL, respectively, demonstrating that their inhibitory activities against tyrosinase enzyme were better compared with kojic acid and hydroquinone as the positive controls. We also found that HC gave 2025 µg/mL as the IC50 value against Vero cells, confirming that it was not toxic to the normal cell line. The molecular docking study gave the root-mean-square deviation value of less than 2 Å. Furthermore, the binding energies of hydroxychalcone derivatives were found as -30.13 and -31.38 kJ/mol, showing that those compounds could be potentially used as the alternative tyrosinase inhibitors in medical application. [ABSTRACT FROM AUTHOR] |
| Databáze: |
Complementary Index |
| Externí odkaz: |
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