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1,5-Anhydro-d-glucitol derivative and galloylated flavonoids isolated from the leaves of Acer ginnala Maxim. as dual inhibitors of PTP1B and α-glucosidase enzymes: In vitro and in silico studies
Phytochemistry ( IF 3.2 ) Pub Date : 2023-06-19 , DOI: 10.1016/j.phytochem.2023.113769
Thi Thanh Le 1 , Manh Tuan Ha 1 , Thao Quyen Cao 2 , Jeong Ah Kim 3 , Jae Sue Choi 4 , Byung Sun Min 1
Affiliation  

Four undescribed compounds (two 1,5-anhydro-d-glucitol derivatives and two galloyl derivatives) and fourteen known compounds were isolated and structurally identified from leaves of Acer ginnala Maxim. (Amur maple). Structures and absolute configurations of the four undescribed compounds were determined using extensive analysis of NMR spectroscopic, HRESI-MS, modified Mosher ester method, and comparison with spectroscopic data of known compounds. Bioactivity evaluation revealed that the isolated 1,5-anhydro-d-glucitol derivative, galloylated flavonol rhamnosides, and galloylated flavanols had inhibitory effects on both protein tyrosine phosphatase-1B (PTP1B, IC50 values ranging of 3.46–12.65 μM) and α-glucosidase (IC50 values ranging of 0.88–6.06 μM) in comparison with a positive control for PTP1B (ursolic acid, IC50 = 5.10 μM) or α-glucosidase (acarbose, IC50 = 141.62 μM). A combination of enzyme kinetic analysis and molecular docking provided additional evidence in favor of their inhibitory activities and mechanism. These data demonstrate that A. ginnala Maxim. together with its constituents are promising sources of potent candidates for developing novel anti-diabetic medications.



中文翻译:

从 Acer ginnala Maxim 叶子中分离出的 1,5-脱水-d-葡萄糖醇衍生物和没食子酰化黄酮类化合物。作为 PTP1B 和 α-葡萄糖苷酶的双重抑制剂:体外和计算机研究

从红枫叶中分离并鉴定了四种未描述的化合物(两种 1,5-脱水-d-葡萄糖醇衍生物和两种没食酰衍生物)和十四种已知化合物。(阿穆尔枫)。通过对NMR光谱、HRESI-MS、改进的 Mosher 酯法的广泛分析,并与已知化合物的光谱数据进行比较,确定了四种未描述的化合物的结构和绝对构型。生物活性评估表明,分离的1,5-脱水-d-葡萄糖醇衍生物、没食子酰化黄酮醇鼠李糖苷和没食子酰化黄烷醇对蛋白酪氨酸磷酸酶-1B(PTP1B,IC 50值范围为3.46–12.65 μM)和α -葡萄糖苷酶(IC 50值范围为 0.88–6.06 μM)与 PTP1B(熊果酸,IC 50  = 5.10 μM)或α-葡萄糖苷酶(阿卡波糖,IC 50  = 141.62 μM)的阳性对照相比。酶动力学分析和分子对接的结合提供了有利于其抑制活性和机制的额外证据。这些数据表明A. gennala Maxim。及其成分是开发新型抗糖尿病药物的有效候选药物的有前途的来源。

更新日期:2023-06-19
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