School of Traditional Chinese Materia Medica, Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China.
School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, People's Republic of China.
Fitoterapia. 2019 Sep;137:104287. doi: 10.1016/j.fitote.2019.104287. Epub 2019 Aug 3.
Phytochemical investigation of the fruit of Crataegus pinnatifida led to the isolation of four pairs of dihydrobenzofuran neolignan enantiomers (1a/1b-4a/4b) including six new compounds (1a/1b, 2a/2b, 3a and 4a). The enantioseparations of the racemates were achieved successfully by chiral chromatographic column. Their structures were established by comprehensive spectroscopic analyses and the absolute configurations were determined by quantum mechanical calculation of electronic circular dichroism (ECD) spectra. All compounds were evaluated in vitro for their cytotoxicity using human hepatocellular carcinoma Hep3B and HepG2 cells. Among them, it was found that 2a had a selective cytotoxicity against Hep3B cells with IC value of 25.47 μM, while the IC value of its enantiomer 2b on Hep3B cells was 59.37 μM. These results implied that the absolute configurations of 2a and 2b possessed remarkable influences on their cytotoxicity. Further flow cytometry analysis indicated that 2a performed more significant effect on cell apoptosis compared with its enantiomer 2b.
从山楂的果实中进行植物化学研究，分离得到了四对二氢苯并呋喃新木脂素对映体（1a/1b-4a/4b），其中包括 6 个新化合物（1a/1b、2a/2b、3a 和 4a）。通过手性色谱柱成功实现了外消旋体的对映体分离。通过综合光谱分析确定了它们的结构，并通过量子力学计算电子圆二色性（ECD）光谱确定了绝对构型。所有化合物均在体外用人肝癌 Hep3B 和 HepG2 细胞进行了细胞毒性评估。其中，发现 2a 对 Hep3B 细胞具有选择性细胞毒性，IC 值为 25.47 μM，而其对映体 2b 对 Hep3B 细胞的 IC 值为 59.37 μM。这些结果表明，2a 和 2b 的绝对构型对其细胞毒性有显著影响。进一步的流式细胞术分析表明，2a 对细胞凋亡的作用比其对映体 2b 更显著。
