Beilstein Arch. 2025, 202543. https://doi.org/10.3762/bxiv.2025.43.v1
Published 03 Jul 2025
Esculin, a coumarin glucoside, was subjected to γ-irradiation in methanolic solution to afford two novel dihydrocoumarin derivatives, esculinosins A (2) and B (3), via regioselective hydroxymethylation at the cis-olefinic bond. The structures of the newly generated compounds 2 and 3 were identified using spectroscopic methods, including nuclear magnetic resonance and mass spectrometry. Compound 2, bearing two hydroxymethyl functionalities at the C-3 and C-4 positions, exhibited a significantly enhanced α-glucosidase inhibitory activity (IC50 = 36.0 ± 1.0 µM) compared to the parent esculin (IC50 = 147.8 ± 2.5 µM). Enzyme kinetic studies confirmed that both compounds function as competitive inhibitors, with esculinosin A (2) exhibiting the lowest Kᵢ value (32.1 ± 0.9 µM). These findings suggest that γ-irradiation-induced hydroxymethylation is an effective strategy for improving the biological activities of dihydrocoumarin derivatives, highlighting the potential for developing novel non-sugar-based hypoglycemic agents.
Keywords: esculin; dihydrocoumarin; hydroxymethylation; radiolysis; α-glucosidase inhibitor
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Jeong, G. H.; Lee, H.; Kim, S. A.; Chung, B. Y.; Kim, T. H.; Bai, H.-W. Beilstein Arch. 2025, 202543. doi:10.3762/bxiv.2025.43.v1
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