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<p>Esculin, a coumarin glucoside, was subjected to γ-irradiation in methanolic solution to afford two novel γ-lactone derivatives, compounds <b>2</b> and <b>3</b>. The structures of the newly generated compounds <b>2</b> and <b>3</b> were identified using spectroscopic methods, including nuclear magnetic resonance and mass spectrometry. Compound <b>2</b>, featuring an additional hydroxymethyl substituent on the γ-butyrolactone scaffold, exhibited significantly enhanced α-glucosidase inhibitory activity (IC<sub>50</sub> = 36.0 ± 1.0 µM) compared with the parent esculin (IC<sub>50</sub> = 147.8 ± 2.5 µM). Enzyme kinetic studies confirmed that both compounds function as competitive inhibitors, with <b>2</b> exhibiting the lowest <i>Ki</i> value (32.1 ± 0.9 µM). These findings demonstrate that γ-irradiation is an effective one-step strategy for generating biologically active γ-lactone derivatives from natural coumarin glycosides and highlight its potential for the development of novel non-sugar-based hypoglycemic agents.</p>

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New phenyl γ-butyrolactone glucosides derived from γ-irradiation of esculin in methanol exhibit significant α-glucosidase inhibitory activity

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2026年7月9日

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  • Gyeong Han Jeong,
  • Hanui Lee,
  • Byung Yeoup Chung,
  • Tae Hoon Kim,
  • Hyoung-Woo Bai

摘要

Esculin, a coumarin glucoside, was subjected to γ-irradiation in methanolic solution to afford two novel γ-lactone derivatives, compounds 2 and 3. The structures of the newly generated compounds 2 and 3 were identified using spectroscopic methods, including nuclear magnetic resonance and mass spectrometry. Compound 2, featuring an additional hydroxymethyl substituent on the γ-butyrolactone scaffold, exhibited significantly enhanced α-glucosidase inhibitory activity (IC50 = 36.0 ± 1.0 µM) compared with the parent esculin (IC50 = 147.8 ± 2.5 µM). Enzyme kinetic studies confirmed that both compounds function as competitive inhibitors, with 2 exhibiting the lowest Ki value (32.1 ± 0.9 µM). These findings demonstrate that γ-irradiation is an effective one-step strategy for generating biologically active γ-lactone derivatives from natural coumarin glycosides and highlight its potential for the development of novel non-sugar-based hypoglycemic agents.