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Comparative Study of Dietary Flavonoids with Different Structures as α-Glucosidase Inhibitors and Insulin Sensitizers.

Yijia Jia,Yanli Ma,Guiguang Cheng,Yuanyue Zhang,Shengbao Cai

Published 2019 in Journal of Agricultural and Food Chemistry

ABSTRACT

This work was designed to comparatively investigate 27 dietary flavonoids that act as α-glucosidase inhibitors and insulin sensitizers. Based on the results of in vitro experiment of α-glucosidase inhibition, myricetin (IC50 = 11.63 ± 0.36 μM) possessed the strongest inhibitory effect, followed by apigenin-7-O-glucoside (IC50 = 22.80 ± 0.24 μM), and fisetin (IC50 = 46.39 ± 0.34 μM). A 3D-QSAR model of α-glucosidase inhibitors with good predictive capability (CoMFA, q2= 0.529, optimum number of components [ONC]= 10, R2= 0.996, F-value [F]= 250.843, standard error of estimation [SEE]= 0.064, two descriptors; and CoMSIA, q2= 0.515, ONC= 10, R2= 0.997, F= 348.301, SEE= 0.054, four descriptors) was established and indicated that meta-positions of ring B favored bulky and minor, electron-withdrawing, and hydrogen bond donor groups. The presence of electron-donating and hydrogen bond acceptor groups at position 4' of ring B could improve α-glucosidase activity. Position 3 of ring C favored minor, electron-donating, and hydrogen bond donor groups, whereas position 7 of ring A favored bulky and hydrogen bond acceptor groups. Molecular docking screened five flavonoids (baicalein, isorhamnetin-3-O-rutinoside, apigenin-7-O-glucoside, kaempferol-7-O-β-glucoside, and cyanidin-3-O-glucoside) that can act as insulin sensitizers and form strong combinations with four key protein targets involved in the insulin signaling pathway. Apigenin-7-O-glucoside (60 µM) can effectively improve insulin resistance, and glucose uptake increased by approximately 73.06% relative to the model group of insulin-resistant HepG2 cells. Therefore, apigenin-7-O-glucoside might serve as the most effective α-glucosidase inhibitor and insulin sensitizer. This work may guide diabetes patients to improve their condition through dietary therapy.

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