Lee, Jieun and Park, Hye Soo and Jung, Hee Jin and Park, Yu Jung and Kang, Min Kyung and Kim, Hye Jin and Yoon, Dahye and Ullah, Sultan and Kang, Dongwan and Park, Yujin and Chun, Pusoon and Chung, Hae Young and Moon, Hyung Ryong (2023) Anti-Browning Effect of 2-Mercaptobenzo[d]imidazole Analogs with Antioxidant Activity on Freshly-Cut Apple Slices and Their Highly Potent Tyrosinase Inhibitory Activity. Antioxidants, 12 (10). p. 1814. ISSN 2076-3921
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Abstract
Ten 2-mercaptobenzimidazole (2-MBI) analogs were synthesized as potential tyrosinase inhibitors because mercapto-containing compounds can bind to copper ions at the active site of tyrosinase to inhibit enzyme activity. Nine 2-MBI analogs showed sub-micromolar IC50 values for mushroom tyrosinase monophenolase activity; analog 4 was 280-fold more potent than kojic acid, and in diphenolase activity, 6 was 970-fold more potent than kojic acid. The inhibition mode of the 2-MBI analogs was investigated using kinetic studies supported by docking simulations. Benzimidazoles without the 2-mercapto substituent of the 2-MBI analogs lost their tyrosinase inhibitory activity, implying that the 2-mercapto substituent plays an important role in tyrosinase inhibition. The 2-MBI analogs exerted potent antioxidant effects against 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS), 2,2-diphenyl-1-picrylhydrazyl (DPPH), and reactive oxygen species (ROS). The results obtained from apple slices and human embryonic kidney cells (HEK-293) suggest that most 2-MBI analogs are sufficiently safe candidates to delay the browning of apple slices effectively. Thus, these results support the potential use of 2-MBI analogs as anti-browning agents in foods such as mushrooms, vegetables, and fruits.
Item Type: | Article |
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Subjects: | Eurolib Press > Agricultural and Food Science |
Depositing User: | Managing Editor |
Date Deposited: | 08 Jan 2024 05:39 |
Last Modified: | 08 Jan 2024 05:39 |
URI: | http://info.submit4journal.com/id/eprint/3344 |