School of Traditional Chinese Materia Medica, Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China.
School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, People's Republic of China.
Fitoterapia. 2018 Jun;127:301-307. doi: 10.1016/j.fitote.2018.03.003. Epub 2018 Mar 11.
Eight new phenylpropanoids (1a/1b, 2-4, 5a/5b and 6) including two pairs of enantiomers (1a/1b and 5a/5b), along with a known analogue (7) were isolated from the fruit of Crataegus pinnatifida. Their structures were elucidated using comprehensive spectroscopic methods. Compounds 1a/1b and 5a/5b were separated successfully by chiral chromatographic column. The absolute configurations of enantiomers were determined by comparison between the experimental and calculated electronic circular dichroism (ECD) spectra. The in vitro antitumor activities of the isolates were evaluated against two human hepatocellular carcinoma HepG2 and Hep3B cells. Five compounds (1a/1b, 2-4) exhibited more potent cytotoxicity and their structure-activity relationships were also discussed. Annexin V-FITC/PI staining using flow cytometry was carried out to examine cell apoptosis, and the results showed that compounds 3-4 with the presence of two methoxy groups substituted at C-3' significantly induced apoptosis in HepG2 cells.
从山楂果实中分离得到了 8 个新的苯丙素类化合物（1a/1b、2-4、5a/5b 和 6），包括两对对映异构体（1a/1b 和 5a/5b），以及一个已知的类似物（7）。采用综合光谱方法阐明了它们的结构。通过手性色谱柱成功分离出化合物 1a/1b 和 5a/5b。通过比较实验和计算的电子圆二色性（ECD）光谱确定了对映异构体的绝对构型。对分离得到的化合物进行了体外抗肿瘤活性评价，针对两种人肝癌 HepG2 和 Hep3B 细胞进行了测试。其中 5 个化合物（1a/1b、2-4）表现出更强的细胞毒性，还讨论了它们的构效关系。通过流式细胞术用 Annexin V-FITC/PI 染色检测细胞凋亡，结果表明，在 C-3' 位带有两个甲氧基取代的化合物 3-4 可显著诱导 HepG2 细胞凋亡。
