Department of Chemistry, Indian Institute of Technology Tirupati, Tirupati, Andhra Pradesh 517506, India.
Department of Chemistry, School of Natural Sciences, Shiv Nadar University, Gautam Buddha Nagar, Uttar Pradesh 201314, India.
J Agric Food Chem. 2022 Aug 10;70(31):9730-9747. doi: 10.1021/acs.jafc.2c02359. Epub 2022 Jul 21.
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 and with remarkable glutathione peroxidase (GPx) enzyme-like activity. The presence of benzimidazole moiety enhances the tyrosinase inhibition efficiency of selone (IC = 0.4 μM) by almost 600 times higher than imidazole-based selone (IC = 238 μM). Interestingly, the addition of another aromatic ring to the benzimidazole moiety has led to the development of an efficient lipid-soluble tyrosinase inhibitor (IC = 2.4 μM). The selenium center and the -NH group of and are extremely crucial to exhibit high GPx-like activity and tyrosinase inhibition potency. The hydrophobic moiety of the inhibitors ( and ) 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 exhibited excellent antibrowning and polyphenol oxidase inhibition properties in banana and apple juice extracts.
过氧化氢在黑色素生成过程中起着至关重要的作用，它可以调节关键的黑色素形成酶酪氨酸酶的活性，而酪氨酸酶负责水果、蔬菜和海鲜的褐变。因此，一种具有双重活性的分子，既能有效抑制酪氨酸酶，又能强烈降解过氧化氢，可能是一种很有前途的防褐变剂。在此，我们报道了高效的基于硒酮的蘑菇酪氨酸酶抑制剂 和 ，它们具有显著的谷胱甘肽过氧化物酶（GPx）样酶活性。苯并咪唑部分的存在使硒酮 的酪氨酸酶抑制效率（IC = 0.4 μM）提高了近 600 倍，而基于咪唑的硒酮 （IC = 238 μM）则提高了 600 倍。有趣的是，在苯并咪唑部分再添加一个芳环，就得到了一种高效的脂溶性酪氨酸酶抑制剂 （IC = 2.4 μM）。抑制剂 和 中的硒中心和 -NH 基团对表现出高 GPx 样酶活性和酪氨酸酶抑制能力至关重要。抑制剂的疏水性部分（ 和 ）进一步帮助它们紧密结合在酶的活性部位，并促进 C═Se 基团与铜离子强烈配位。抑制剂 在香蕉和苹果汁提取物中表现出优异的防褐变和多酚氧化酶抑制性能。
