Synthesis and Evaluation of Benzophenone O‐Glycosides as α‐Glucosidase Inhibitors

The first total synthesis of benzophenone O‐glycosides (iriflophenone 2‐O‐α‐L‐rhamnopyranoside: 1 and aquilarisinin: 2) isolated from the leaves of Aquilaria sinensis and related new derivatives (3–12) was accomplished through suitable protecting group manipulations and glycosylation starting from commercially available L‐rhamnose, D‐glucose, D‐galactose, D‐mannose, D‐xylose, and 1,3,5‐trihydroxybenzene. All synthesized benzophenone O‐glycosides were evaluated for their inhibitory activities against α‐glucosidase. Of these, benzophenone O‐glycosides 4 and 10 exhibited the most potent inhibitory activity in vitro against α‐glucosidase with IC50 values of 168.7 ± 13.9 and 210.1 ± 23.9 µM, respectively, when compared with that of the positive control acarbose with an IC50 value of 569.3 ± 49.7 µM.

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