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Lichen-derived depsidones have been a successful source for alpha-glucosidase inhibitory agents with numerous advantages. In this article, derivatives of protocetraric acids were designed and synthesised. Diels-Alder reaction, esterification, and Friedel-Crafts alkylation of protocetraric acid with different reagents under Lewis acid were performed. Eleven products were prepared, including 10 new compounds and parmosidone A. Among them, compounds  2–4  and  6  had the novel skeletons. The newly synthetic products were evaluated for alpha-glucosidase inhibition. Among tested compounds,  9  showed the strongest activity, with an IC 50  value of 5.9 µM. The molecular docking model indicated the consistency between  in vitro  and  in silico  data of alpha-glucosidase inhibition.

α-Glucosidase inhibitory derivatives of protocetraric acid