Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 70, Issue 31, Pages -Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jafc.2c02359
Keywords
monophenolase activity; diphenolase activity; selone; thione; tyrosinase
Funding
- SNU
- SERB [CRG/2018/004591]
- DBT, Government of India [BT/RLS/Re-entry/10/2017]
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Hydrogen peroxide plays a crucial role in melanogenesis, and this article reports highly efficient selone-based mushroom tyrosinase inhibitors with remarkable GPx-like activity. The presence of benzimidazole moiety enhances the inhibition efficiency, and the selenium center and -NH group are crucial for activity.
Hydrogen peroxide plays a crucial role in the melanogenesis process by regulating the activity of the key melanin forming enzyme tyrosinase, responsible for the browning of fruits, vegetables, and seafood. Therefore, a molecule with dual activities, both efficient tyrosinase inhibition and strong hydrogen peroxide degrading ability, may act as a promising antibrowning agent. Herein, we report highly efficient selone-based mushroom tyrosinase inhibitors 2 and 3 with remarkable glutathione peroxidase (GPx) enzyme-like activity. The presence of benzimidazole moiety enhances the tyrosinase inhibition efficiency of selone 2 (IC50 = 0.4 mu M) by almost 600 times higher than imidazole-based selone 1 (IC50 = 238 mu M). Interestingly, the addition of another aromatic ring to the benzimidazole moiety has led to the development of an efficient lipid-soluble tyrosinase inhibitor 3 (IC50 = 2.4 mu M). The selenium center and the -NH group of 2 and 3 are extremely crucial to exhibit high GPx-like activity and tyrosinase inhibition potency. The hydrophobic moiety of the inhibitors (2 and 3) further assists them in tightly binding at the active site of the enzyme and facilitates the C=Se group to strongly coordinate with the copper ions. Inhibitor 2 exhibited excellent antibrowning and polyphenol oxidase inhibition properties in banana and apple juice extracts.
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