Zhao Wen-Yu, Chen Jing-Jie, Zou Chun-Xin, Zhou Wei-Yu, Yao Guo-Dong, Wang Xiao-Bo, Lin Bin, Huang Xiao-Xiao, Song Shao-Jiang
School of Traditional Chinese Materia Medica, Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province, Shenyang Pharmaceutical University, Shenyang, People's Republic of China.
Chinese People's Liberation Army 210 Hospital, Dalian, People's Republic of China.
Planta Med. 2019 May;85(8):648-656. doi: 10.1055/a-0879-4721. Epub 2019 Apr 11.
Four pairs of -carboline enantiomers (1A: /1B: -4A: /4B: ), 2 -carboline derivatives (5: - 6: ) with a single enantiomeric configuration, together with 2 known achiral congeners (7: - 8: ) were isolated from the stems of Their structures were elucidated on the basis of extensive spectroscopic analyses and quantum mechanical calculations. Compound 5: possesses a 4,5-seco -carboline framework and represents the first example of this type of -carboline alkaloids from nature. A possible biosynthetic pathway is proposed to generate the racemate 4: and the enantiomerically pure compounds 5: and 6: . All isolates were screened for their cytotoxicity against hepatocellular carcinoma Hep3B and HepG2 cells, which revealed that enantiomeric compounds 4A: and 4B: had distinctive effects in HepG2 cells. Further investigation showed that 4B: could induce apoptosis in HepG2 cells.
从[植物名称]茎中分离出四对对映体咔啉（1A:/1B: - 4A:/4B:）、具有单一对映体构型的2种咔啉衍生物（5: - 6:）以及2种已知的非手性类似物（7: - 8:）。通过广泛的光谱分析和量子力学计算阐明了它们的结构。化合物5:具有4,5-开环咔啉骨架，是该类咔啉生物碱的首个天然实例。提出了一条可能的生物合成途径来生成外消旋体4:以及对映体纯的化合物5:和6:。对所有分离物进行了针对肝癌Hep3B和HepG2细胞的细胞毒性筛选，结果表明对映体化合物4A:和4B:在HepG2细胞中有显著不同的作用。进一步研究表明4B:可诱导HepG2细胞凋亡。
