Discovery of pyrogallol thermal reaction products from a model process of roasting coffee beans as potent α-glucosidase inhibitors
Discovery of pyrogallol thermal reaction products from a model process of roasting coffee beans as potent α-glucosidase inhibitors
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DOI：
10.1016/j.fbio.2022.101583
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发表时间：
2022-02
期刊：
影响因子：
5.2
通讯作者：
Hui Wang;X. Kang;Shiwei Sun;Yichen Yin;Kun-Dao Jiang;Guodong Tang;Xinning Tang;Wei Wang-
中科院分区：
文献类型：
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作者：
Hui Wang;X. Kang;Shiwei Sun;Yichen Yin;Kun-Dao Jiang;Guodong Tang;Xinning Tang;Wei Wang-
焦性没食子酸是咖啡饮料中的一种多酚类化合物，其烘焙过程可显著提高其α-葡萄糖苷酶抑制活性。在本研究中，采用生物活性导向的方法分离了焦性没食子酸的热反应产物，并鉴定了两种有效的α-葡萄糖苷酶抑制剂：焦性没食子酸4-4′二聚体（4，4 ′-DP）和焦性没食子酸4-5′二聚体（4，5 ′-DP）。它们的α-葡萄糖苷酶抑制活性均高于邻苯三酚，IC_（50）值分别为206.2 ± 1.2μM（4，4 ′-DP），187.6 ± 2.6μM（4，5 ′-DP），2660 ± 60.1μM（邻苯三酚）。与阿卡波糖相比，焙烧产物是更有效的α-葡萄糖苷酶抑制剂（IC 50 = 695 ± 12.7μM）。酶动力学结果表明，4，4 ′-DP和4，5 ′-DP分别以非竞争性和非竞争性方式抑制α-葡萄糖苷酶。对接模拟表明，这两种化合物与α-葡萄糖苷酶之间的相互作用力主要为氢键和疏水作用。这些结果表明，简单的烘焙过程可能会增加含焦性没食子酚食品（如咖啡饮料）的α-葡萄糖苷酶抑制活性。
The roasting process of pyrogallol, a polyphenol compound distributed in coffee beverages, significantly enhanced itsα-glucosidase inhibitory activity. In this study, a bioassay-guided isolation of the thermal reaction products of pyrogallol led to the identification of two potentα-glucosidase inhibitors, 4-4′ dimer of pyrogallol (4,4′-DP) and 4-5′ dimer of pyrogallol (4,5′-DP). Theirα-glucosidase inhibitory activity was higher than that of pyrogallol, as evidenced by comparing the IC50values (206.2 ± 1.2μM for 4,4′-DP, 187.6 ± 2.6μM for 4,5′-DP, 2660 ± 60.1μM for pyrogallol). And the roasting products were more potentα-glucosidase inhibitors compared to acarbose (IC50= 695 ± 12.7μM). Enzyme kinetics demonstrated that 4,4′-DP and 4,5′-DP inhibitedα-glucosidase in an uncompetitive and a non-competitive manner, respectively. Docking simulations revealed that the main interaction forces between these two compounds andα-glucosidase were hydrogen bonding and hydrophobic effect. These results suggested that a simple roasting process might increase theα-glucosidase inhibitory activity of pyrogallol-containing foods such as coffee beverages.