
Bioorganic and Medicinal Chemistry p. 5355 - 5364 (2017)
Update date:2022-08-03
Topics:
Zhen, Jing
Dai, Yujie
Villani, Tom
Giurleo, Daniel
Simon, James E.
Wu, Qingli
A series of novel flavonoid alkaloids were synthesized with different flavonoids and attached nitrogen-containing moieties. These new compounds were screened for inhibitory activity of α-glucosidase, among which compound 23 was found to show the lowest IC50 of 4.13 μM. Kinetic analysis indicates that the synthesized compounds 15 and 23 inhibit the enzyme in a non-competitive model with Ki value of 37.8 ± 0.8 μM and 13.2 ± 0.6 μM. Further docking studies suggest that the preferred binding pocket is close to the catalytic center, correlating to the experimental results. Structure activity relationship studies (SAR) indicate that 4′-hyroxyl group and the 4-position carbonyl group in the flavonoid structure are important for this biological activity. Addition of extra hydrogen bonding and hydrophobic groups on ring A would increase the inhibitory activity.
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