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  3. Rapid purification of diastereoisomers from Piper kadsura using supercritical fluid chromatography with chiral stationary phases

Rapid purification of diastereoisomers from Piper kadsura using supercritical fluid chromatography with chiral stationary phases

  • J Chromatogr A. 2017 Aug 4;1509:141-146. doi: 10.1016/j.chroma.2017.06.020.
Huaxia Xin 1,  Zhuoshun Dai 1,  Jianfeng Cai 1,  Yanxiong Ke 1,  Hui Shi 1,  Qing Fu 2,  Yu Jin 3,  Xinmiao Liang 4
Affiliations

Affiliations

  • 1 Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, PR China.
  • 2 Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, PR China. Electronic address: [email protected].
  • 3 Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, PR China. Electronic address: [email protected].
  • 4 Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, PR China; Key Lab of Separation Science for Analytical Chemistry, Key Lab of Natural Medicine, Liaoning Province, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, PR China.
PMID: 28641835 DOI: 10.1016/j.chroma.2017.06.020
Abstract

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%.

Keywords

Achiral separation; Chiral supercritical fluid chromatography; Diastereoisomers; Piper kadsura; Purification.

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