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The targeted identification of α-glucosidase inhibitors from the crude ethyl acetate of  Lycopodiella cernua  (L.) Pic. Serm ( L.cernua ) was guided by high-resolution inhibition profiling. The α-glucosidase inhibition profiling and HPLC-QTOF-MS showed tannins and serratenes were the corresponding antidiabetic constituents. Two new serratenes named 3β, 21β-dihydroxyserra-14-en-24-oic acid-3β-(4'-methoxy-5'-hydroxybenzoate) ( 4 ), 3β, 21α-dihydroxyserra-14-en-24-oic acid-3β-(4'-methoxy-5'-hydroxybenzoate) ( 7 ), together with two known compounds ( 5  and  6 ) were isolated. Their structures were elucidated by HR-ESI-MS and NMR. Compounds  5 – 7  inhibited the α-glucosidase activity in a non-competitive manner with Ki values ranging from 1.29 to 12.9 µM. The molecular docking result unveiled that  4 – 7  bound to the residues at the channel site, which enabled to block the substrate access. In addition, the molecular dynamics (MD) simulation of the most active compound  7  and α-glucosidase indicated the 4′-methoxy-5′-hydroxybenzoate group formed the stable hydrogen bonds and pi-pi T-shaped interactions with Arg312, Gln350 and Phe300 residues, while the rings D and E were stabilized by hydrophobic interaction.

natural product research

A high-resolution α-glucosidase inhibition profiling for targeted identification of natural antidiabetic products from  Lycopodiella cernua  (L.) Pic. Serm and their inhibitory mechanism study