The EtOAc fraction of Alpinia katsumadai seeds showed significant inhibition on glycogen phosphorylase a (GPa) with inhibitory ratios of 97.9% and 64.6% at concentrations of 200 and 100 μg/mL, respectively. Bioactivity-guided isolation afforded 15 new diarylheptanoid-flavanone hybrids, katsumadainols B₁—B₁₅ (1—15), together with eight known ones (16—23). Compounds 4—10 and 12—21 exhibited activity against GPa with IC₅₀ values of 10.1—95.4 μmol/L; compounds 4, 5, 16, and 17 displayed inhibitory effects on α-glucosidase with IC₅₀ values of 7.1, 12.4, 7.2, and 8.3 μmol/L, obviously higher than acarbose (IC₅₀, 209.1 μmol/L); compounds 4—6, 14, 16—20, 22, and 23 were PTP1B/TCPTP selective inhibitors with IC₅₀ values of 40.7—95.8 μmol/L; compounds 4, 5, 16, and 17 showed DPP4 inhibitory effects with inhibitory ratios of 50.0%—54.2% (200 μmol/L). Diarylheptanoid-flavanone hybrids (4, 5, 16, and 17) with a p-hydroxybenzyl at C-6 position represent a promising class of multiple-target antidiabetic agents inhibiting GPa, α-glucosidase, PTP1B, and DPP4.

中文翻译：

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二芳基庚烷-黄烷酮杂化物作为来自山姜的多靶点降糖药

在 200 和 100 μg/mL 的浓度下，山姜种子的 EtOAc 级分显示出对糖原磷酸化酶 a (GPa) 的显着抑制，抑制率分别为 97.9% 和 64.6%。生物活性引导的分离提供了 15 个新的二芳基庚烷-黄烷酮杂化物，即 katsumadinols B ₁ -B ₁₅ (1-15)，以及 8 个已知的 (16-23)。化合物4-10和12-21均表现出对GPa的活性，IC ₅₀值为10.1-95.4 μmol/L；化合物4、5、16、17对α-葡萄糖苷酶有抑制作用，IC _{50 分别}为7.1、12.4、7.2、8.3 μmol/L，明显高于阿卡波糖（IC ₅₀, 209.1 μmol/L)；化合物4-6、14、16-20、22和23为PTP1B/TCPTP选择性抑制剂，IC ₅₀值为40.7-95.8 μmol/L；化合物4、5、16、17对DPP4具有抑制作用，抑制率为50.0%～54.2%（200 μmol/L）。在 C-6 位具有对羟基苄基的二芳基庚烷-黄烷酮杂化物（4、5、16 和 17）代表了一类有前景的多靶点抗糖尿病药物，可抑制 GPa、α-葡萄糖苷酶、PTP1B 和 DPP4。