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Synthesis and Evaluation of Coumarin-Chalcone Derivatives as α-Glucosidase Inhibitors

Chun‐Mei Hu, Yong-Xin Luo, Wenjing Wang, Jianping Li, Mengyue Li, Yufei Zhang, Di Xiao, Li Lu, Zhuang Xiong, Na Feng, Chen Li

2022Frontiers in Chemistry19 citationsDOIOpen Access PDF

Abstract

Coumarin and chalcone, two important kinds of natural product skeletons, both exhibit α-glucosidase inhibitory activity. In this work, coumarin-chalcone derivatives 3 ( a∼v ) were synthesized, and their α-glucosidase inhibitory activity was screened. The results showed that all synthetic derivatives (IC 50 : 24.09 ± 2.36 to 125.26 ± 1.18 μM) presented better α -glucosidase inhibitory activity than the parent compounds 3-acetylcoumarin (IC 50 : 1.5 × 10 5 μM) and the positive control acarbose (IC 50 : 259.90 ± 1.06 μM). Among them, compound 3t displayed the highest α -glucosidase inhibitory activity (IC 50 : 24.09 ± 2.36 μM), which was approximately 10 times stronger than that of acarbose. The kinetic assay of 3t ( K I = 18.82 μM, K IS = 59.99 μM) revealed that these compounds inhibited α-glucosidase in a mixed-type manner. Molecular docking was used to simulate the interaction between α-glucosidase and compound 3t .

Topics & Concepts

AcarboseChalconeCoumarinIC50ChemistryStereochemistryInhibitory postsynaptic potentialNatural productDocking (animal)EnzymeBiochemistryIn vitroOrganic chemistryBiologyNeuroscienceMedicineNursingNatural Antidiabetic Agents StudiesPsidium guajava Extracts and ApplicationsPhytochemicals and Antioxidant Activities