CAS Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Sciences (CAS), Lanzhou, 730000, PR China; University of Chinese Academy of Sciences, Chinese Academy of Sciences, Beijing, 100049, PR China.
Korea Bioactive Natural Material Bank, College of Pharmacy and Research Institute of Pharmaceutical Sciences, Seoul National University, Seoul, 08826, Republic of Korea.
Phytochemistry. 2018 Nov;155:171-181. doi: 10.1016/j.phytochem.2018.08.008. Epub 2018 Aug 18.
To search for bioactive gypenosides and their analogues, a saponin enriched fraction and its hydrolyzate from Gynostemma pentaphyllum were phytochemically investigated. Fractionation by diverse chromatographic methods, including HPLC, Sephadex LH-20, silica gel, and C18 reverse phase silica gel, led to the isolation and purification of twelve triterpenes, including five undescribed and seven known. The chemical structures of all compounds were determined as analyzed by nuclear magnetic resonance (NMR), high resolution mass spectrometry (HR-MS), infrared spectrum (IR), optical rotation, and chemical transformations. Among all isolates, nine compounds possessed a rare dammarane triterpenoid framework with A-ring modified. The relative configurations of three compounds were determined by 2D NMR for the first time. The absolute configurations of four compounds were determined by the modified Mosher's method. Two of all isolated compounds significantly enhanced 2-deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-D-glucose (2-NBDG) uptake and Glucose Transporter 4 (GLUT4) translocation via activating the AMP-activated protein kinase (AMPK) and acetyl-CoA carboxylase (ACC) signaling pathway. This study provided the potential candidates for the development of antidiabetic agents.
为了寻找具有生物活性的绞股蓝皂苷及其类似物，对绞股蓝中一种皂苷富集部分及其水解产物进行了植物化学研究。通过多种色谱方法（包括 HPLC、Sephadex LH-20、硅胶和 C18 反相硅胶）进行分离和纯化，分离并纯化了 12 种三萜类化合物，其中 5 种为未知化合物，7 种为已知化合物。通过核磁共振（NMR）、高分辨率质谱（HR-MS）、红外光谱（IR）、旋光和化学转化等分析，确定了所有化合物的化学结构。在所有分离出的化合物中，有 9 种化合物具有罕见的达玛烷三萜骨架，A 环被修饰。其中 3 种化合物的相对构型首次通过 2D NMR 确定。通过改良的 Mosher 法确定了 4 种化合物的绝对构型。所有分离出的化合物中有两种能显著增强 2-脱氧-2-[(7-硝基-2,1,3-苯并恶二唑-4-基)氨基]-D-葡萄糖（2-NBDG）摄取和葡萄糖转运蛋白 4（GLUT4）易位，通过激活 AMP 激活蛋白激酶（AMPK）和乙酰辅酶 A 羧化酶（ACC）信号通路。本研究为开发抗糖尿病药物提供了潜在的候选物。
