Xin Huaxia, Dai Zhuoshun, Cai Jianfeng, Ke Yanxiong, Shi Hui, Fu Qing, Jin Yu, Liang Xinmiao
Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, PR China.
Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, PR China.
J Chromatogr A. 2017 Aug 4;1509:141-146. doi: 10.1016/j.chroma.2017.06.020. Epub 2017 Jun 12.
Supercritical fluid chromatography (SFC) with chiral stationary phases (CSPs) is an advanced solution for the separation of achiral compounds in Piper kadsura. Analogues and stereoisomers are abundant in natural products, but there are obstacles in separation using conventional method. In this paper, four lignan diastereoisomers, (-)-Galbelgin, (-)-Ganschisandrin, Galgravin and (-)-Veraguensin, from Piper kadsura were separated and purified by chiral SFC. Purification strategy was designed, considering of the compound enrichment, sample purity and purification throughput. Two-step achiral purification method on chiral preparative columns with stacked automated injections was developed. Unconventional mobile phase modifier dichloromethane (DCM) was applied to improve the sample solubility. Four diastereoisomers was prepared at the respective weight of 103.1mg, 10.0mg, 152.3mg and 178.6mg from 710mg extract with the purity of greater than 98%.
采用手性固定相的超临界流体色谱法(SFC)是分离海风藤中非手性化合物的一种先进方法。天然产物中类似物和立体异构体丰富,但用传统方法分离存在障碍。本文通过手性SFC分离并纯化了海风藤中的四种木脂素非对映异构体,即(-)-加贝因、(-)-甘西桑德林、加格拉文和(-)-维拉古辛。设计了纯化策略,综合考虑了化合物富集、样品纯度和纯化通量。开发了一种在手性制备柱上采用堆叠自动进样的两步非手性纯化方法。应用非常规流动相改性剂二氯甲烷(DCM)来提高样品溶解度。从710mg提取物中分别制备了四种非对映异构体,重量分别为103.1mg、10.0mg、152.3mg和178.6mg,纯度大于98%。