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Antioxidant activity and inhibition of α-glucosidase by hydroxyl-functionalized 2-arylbenzo[b]furansHsieh, Jung-Feng; Lin, Wei-Jen; Huang, Kai-Fa; Liao, Jiahn-Haur; Don, Ming-Jaw; Shen, Chien-Chang; Shiao, Young-Ji; Li, Wen-Tai
European journal of medicinal chemistry, 03/2015, Volume: 93Journal Article
This study synthesized a series of hydroxyl-functionalized 2-arylbenzobfurans based on the structure of tournefolic acid A and evaluated them for antioxidant and α-glucosidase inhibitory activities. Compounds 5a, 5e, and 5n showed remarkable inhibition of α-glucosidase (IC50 values of 1.9–3.0 μM), and they appear to be even more potent than quercetin. A kinetic binding study indicated that compounds 5a and 5n used a mechanism of mixed-competition to inhibit α-glucosidase. This study also revealed that compounds 5a and 5n bind to either the α-glucosidase or α-glucosidase-4-NPGP complex. Using the crystal structure of the Saccharomyces cerevisiae α-glucosidase, the molecular docking study has predicted the binding of compounds 5a and 5n to the active site of α-glucosidase through both hydrophobic and hydrogen interactions. A DPPH radical scavenging assay further showed that most hydroxyl-functionalized 2-arylbenzobfurans possess antioxidant activity. The exception was compound 5p, which has only one hydroxyl group on the 2-phenyl ring of 2-arylbenzobfuran. Our results indicate that hydroxyl-functionalized 2-arylbenzobfurans possess both antidiabetic as well as antioxidant properties. Display omitted •A series of new hydroxyl-functionalized 2-arylbenzobfurans has synthesized.•Antioxidant and α-glucosidase inhibition activities.•Inhibition kinetics of new compounds were determined.•Molecular docking study predicted the binding of compounds to α-glucosidase.
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