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Gallotannins are phenolic natural products containing galloyl moieties connected to polyhydric alcohol cores, e.g., D-glucose. Some gallotannins are reported to have antidiabetic properties, such as α-glucosidase inhibitory activity. In this study, fourteen unnatural gallotannin derivatives with 1,5-anhydroalditol and inositol as the cyclic polyol cores were synthesized to investigate how their structures affected antioxidative and α-glucosidase inhibitory activities. Tannic acid demonstrated the most potent antioxidative activity (EC50 = 2.84 μM), with potency increasing proportionally to the number of galloyl moieties. Synthetic inositol derivatives outperformed 1,5-anhydroalditol derivatives in rat α-glucosidase inhibitory activity. Pentagalloyl glucose, a natural compound, demonstrated the highest activity (IC50 = 0.336 μM).


Shota Machida, Maho Sugaya, Hiroaki Saito, Taketo Uchiyama. Synthesis and Evaluation of Gallotannin Derivatives as Antioxidants and α-Glucosidase Inhibitors. Chemical & pharmaceutical bulletin. 2021;69(12):1209-1212

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PMID: 34853289

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