基于分子网络从唐古特瑞香中靶向分离细胞毒性二萜酯和原酸酯
Target isolation of cytotoxic diterpenoid esters and orthoesters from Daphne tangutica maxim based on molecular networking.
作者信息
Guo Rui, Li Qian, Mi Si-Hui, Jia Shu-He, Yao Guo-Dong, Lin Bin, Huang Xiao-Xiao, Liu Yu-Yang, Song Shao-Jiang
机构信息
Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province; Engineering Research Center of Natural Medicine Active Molecule Research & Development, Liaoning Province; Key Laboratory of Natural Bioactive Compounds Discovery & Modification, Shenyang; School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, 110016, China.
School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang, 110016, China.
出版信息
Phytochemistry. 2022 Nov;203:113358. doi: 10.1016/j.phytochem.2022.113358. Epub 2022 Aug 14.
Guiding by LC-MS/MS analysis and the GNPS Molecular Networking, five undescribed daphnane diterpenoids, tanguticanines A-E, and eleven known analogues were discovered from the whole plants of Daphne tangutica Maxim. Their structures and absolute configurations were determined via extensive NMR spectroscopic analysis, ECD calculations, and X-ray diffraction crystallography. Tanguticanine E (5) exhibited promising cytotoxicity against the HepG2 cell line with an IC value of 9.93 ± 0.10 μM. Further flow cytometry experiment was performed to detect cell apoptosis, and the results indicated that cytotoxic diterpenoids (tanguticanines B, D and E, altadaphnan C, gniditrin, hirsein A and simplexin) exert their effects through induction of apoptosis.
在液相色谱-串联质谱（LC-MS/MS）分析和全球天然产物分子网络（GNPS Molecular Networking）的指导下，从唐古特瑞香（Daphne tangutica Maxim）全株中发现了5个未描述的瑞香烷二萜类化合物——唐古特瑞香碱A-E，以及11个已知类似物。通过广泛的核磁共振光谱分析、电子圆二色光谱（ECD）计算和X射线衍射晶体学确定了它们的结构和绝对构型。唐古特瑞香碱E（5）对肝癌细胞系HepG2显示出有前景的细胞毒性，IC50值为9.93±0.10 μM。进一步进行了流式细胞术实验以检测细胞凋亡，结果表明具有细胞毒性的二萜类化合物（唐古特瑞香碱B、D和E、阿尔塔达芬南C、瑞香毒素、希尔辛A和单辛素）通过诱导凋亡发挥作用。
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