Journal
FOOD CHEMISTRY
Volume 221, Issue -, Pages 1530-1538Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.foodchem.2016.10.140
Keywords
Thiophene-2-carbaldehyde thiosemicarbazone (TCT) derivatives; Tyrosinase inhibitors; Fluorescence spectrum; 1H and 13C NMR titration
Funding
- National Natural Sciences Foundation of China [20962014]
- free searching foundation of State Key Laboratory of Food Science and Technology (Nanchang University) in China [SKLF-TS-200914]
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We synthesized a series of 4- or 5-functionalized TCT derivatives (1-12) and investigated their inhibitory activities and mechanisms on tyrosinase by using Spectrofluorimetry, 1H and 13C NMR titration and IR spectra. The results of the fluorescence spectra and NMR titrations showed that the thiosemicarbazone moiety formed complexes with copper ions in the active center of the enzyme and played an important role in inhibiting the activities of the target compounds. The 5-functionalization decreased the inhibitory activity, but the 4-functionalization with a methoxyacetyl group enhanced the inhibitory activity, in which a strong auxiliary vicinity synergistic effect from the methoxyacetyl group strengthens and promotes the formation of complexes between the sulfur atoms of the inhibitor and the dicopper nucleus of tyrosinase. We concluded that the appropriate 4-functionalization improved the inhibitory activity of the modifier, and that 4-methoxyacetyl -TCT is promising for the inhibition of tyrosinase. (C) 2016 Elsevier Ltd. All rights reserved.
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