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Tyrosinase inhibitory mechanism and anti-browning properties of novel kojic acid derivatives bearing aromatic aldehyde moiety.

ABSTRACT: Kojic acid-aromatic aldehydes 6a-6m were synthesized and screened for their anti-tyrosinase activities. These compounds showed potently anti-tyrosinase activity with IC₅₀ values in the range of 5.32 ± 0.23 to 77.89 ± 3.36 μM compared with kojic acid (IC₅₀ = 48.05 ± 3.28 μM). Thereinto, compound 6j with 3-fluorine and 4-aldehyde substitutions showed the most potent anti-tyrosinase activity (IC₅₀ = 5.32 ± 0.23 μM). Enzyme kinetic study revealed that 6j is a noncompetitive tyrosinase inhibitor (Ki = 2.73 μM). The action mechanism of 6j was evaluated by fluorescence spectrum quenching, molecular docking, ¹H NMR titration, etc. The anti-browning assay showed that 6j could delay the enzymatic browning of fresh-cut apples. Besides, the cell viability assay proved that 6j had a good safety profile as an anti-browning agent. Hence, these results identify a new class of anti-tyrosinase and anti-browning agents for further investigation in the food industry.

SUBMITTER: Peng Z

PROVIDER: S-EPMC9807860 | biostudies-literature | 2023

REPOSITORIES: biostudies-literature

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Tyrosinase inhibitory mechanism and anti-browning properties of novel kojic acid derivatives bearing aromatic aldehyde moiety.

Peng Zhiyun Z Wang Guangcheng G He Yan Y Wang Jing Jing JJ Zhao Yong Y

Current research in food science 20221222

Kojic acid-aromatic aldehydes 6a-6m were synthesized and screened for their anti-tyrosinase activities. These compounds showed potently anti-tyrosinase activity with IC50 values in the range of 5.32 ± 0.23 to 77.89 ± 3.36 μM compared with kojic acid (IC50 = 48.05 ± 3.28 μM). Thereinto, compound 6j with 3-fluorine and 4-aldehyde substitutions showed the most potent anti-tyrosinase activity (IC50 = 5.32 ± 0.23 μM). Enzyme kinetic study revealed ...[more]

PMID: 36605465

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Project description:Kojic acid, β-arbutin, α-arbutin, and deoxyarbutin have been reported as tyrosinase inhibitors in many articles, but some contradictions exist in their differing results. In order to provide some explanations for these contradictions and to find the most suitable compound as a positive control for screening potential tyrosinase inhibitors, the activity and inhibition type of the aforementioned compounds on monophenolase and diphenolase of mushroom tyrosinase (MTYR) were studied. Their effects on B16F10 cells melanin content, tyrosinase (BTYR) activity, and cell viability were also exposed. Results indicated that α-arbutin competitively inhibited monophenolase activity, whereas they uncompetitively activated diphenolase activity of MTYR. β-arbutin noncompetitively and competitively inhibited monophenolase activity at high molarity (4000 µM) and moderate molarity (250-1000 µM) respectively, whereas it activated the diphenolase activity of MTYR. Deoxyarbutin competitively inhibited diphenolase activity, but could not inhibit monophenolase activity and only extended the lag time. Kojic acid competitively inhibited monophenolase activity and competitive-noncompetitive mixed-type inhibited diphenolase activity of MTYR. In a cellular experiment, deoxyarbutin effectively inhibited BTYR activity and reduced melanin content, but it also potently decreased cell viability. α-arbutin and β-arbutin dose-dependently inhibited BTYR activity, reduced melanin content, and increased cell viability. Kojic acid did not affect cell viability at 43.8-700 µM, but inhibited BTYR activity and reduced melanin content in a dose-dependent manner. Therefore, kojic acid was considered as the most suitable positive control among these four compounds, because it could inhibit both monophenolase and diphenolase activity of MTYR and reduce intercellular melanin content by inhibiting BTYR activity without cytotoxicity. Some explanations for the contradictions in the reported articles were provided.

Dataset Information

Tyrosinase inhibitory mechanism and anti-browning properties of novel kojic acid derivatives bearing aromatic aldehyde moiety.

Publications

Tyrosinase inhibitory mechanism and anti-browning properties of novel kojic acid derivatives bearing aromatic aldehyde moiety.

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