α-Glucosidase Inhibitors from the Leaves of : Structure-Activity Relationship, Kinetic Investigation, and Molecular Docking.

L. is a valuable agricultural crop, extensively utilized in various fields and comprising diverse chemical constituents. In preliminary experiments for rat intestinal α-glucosidase inhibition, the methanolic extract of demonstrated potential for inhibiting maltase and sucrase. Bioassay-guided isolation led to 30 metabolites, including five new cannabinoids (, , , , ) and four new spiroindans (, , , ). Their structures were elucidated using spectroscopic techniques such as NMR, and absolute configurations were determined by Mosher's method. Cannabinoids were the main contributors to inhibitory potency (IC: 0.09-0.8 mM), while spiroindans and simple phenolics showed lower activity (IC: 1.0-2.2 mM). 8-Hydroxycannabinol () was the most potent inhibitor retarding the enzymes through a noncompetitive mechanism. Molecular dynamics simulations of compounds and showed that hydrogen bonding between phenolic hydroxyl groups and specific amino acid residues at the allosteric site was essential for strong α-glucosidase binding.