Preparation of Sesquiterpenoids from Tussilago farfara L. by High-speed Counter-current Chromatography

Kun Cao; Yi Xu; Tian-Ming Zhao; Qing Zhang

doi:10.4103/0973-1296.192196

Preparation of Sesquiterpenoids from Tussilago farfara L. by High-speed Counter-current Chromatography

Pharmacogn Mag. 2016 Oct-Dec;12(48):282-287. doi: 10.4103/0973-1296.192196.

Authors

Kun Cao¹, Yi Xu², Tian-Ming Zhao³, Qing Zhang¹

Affiliations

¹ College of Chemistry and Chemical Engineering, Chongqing University, Chongqing, P.R. China; Defense Key Disciplines Lab of Novel Micro-nano Devices and System Techonlogy, Chongqing, P.R. China.
² College of Chemistry and Chemical Engineering, Chongqing University, Chongqing, P.R. China; Defense Key Disciplines Lab of Novel Micro-nano Devices and System Techonlogy, Chongqing, P.R. China; International R and D Center of Micro-nano Systems and New Materials Technology, Chongqing, P.R. China.
³ College of Chemistry and Chemical Engineering, Chongqing University, Chongqing, P.R. China.

Abstract

Background: Sesquiterpenoids, such as tussilagone, has effects of raising blood pressure, antiplatelet aggregation, and anti-inflammation activities, which is regarded as index compound for quality control of Tussilago farfara L.

Objective: This study was aimed to obtain an effective method for fast isolation of sesquiterpenoids from T. farfara L. by high-speed counter-current chromatography (HSCCC).

Materials and methods: A solvent optimization method for HSCCC was presented, i.e., the separation factors of compounds after the K values of solvent system should be investigated.

Results: A ternary solvent system of n-hexane:methanol:water (5:8:2, v/v/v) was selected and applied for the HSCCC, and 56 mg of tussilagone (2) was isolated from T. farfara L., along with two other sesquiterpenoids 5.6 mg of 2,2-dimethyl-6-acetylchromanone (1) and 22 mg of 14-acetoxy-7 β-(3'-ethyl cis-crotonoyloxy)-lα-(2'-methylbutyryloxy)-notonipetranone (3) by HSCCC with high purities. Their chemical structures were elucidated by liquid chromatography-mass spectrometry and nuclear magnetic resonance experiments.

Conclusion: These results offered an efficient strategy for preparation of potentially health-relevant phytochemicals from T. farfara L., which might be used for further chemical research and pharmacological studies by preparative HSCCC.

Summary: The real separation efficiency has been verified by analytical HSCCC.A solvent optimization method for HSCCC was presented and applied to separate and prepare active compounds.A method for rapid and effective separation of target compound Tussilagone with high yield and purity from the flower buds of Tussilago farfara.Two other compounds 2,2-Dimethyl-6-acetylchromanone and 14-acetoxy-7β-(3'-ethyl cis-crotonoyloxy) -lα- (2'-methylbutyryloxy). notonipetranone hasbeen obtained with high purities from flower buds of Tussilago farfara. Abbreviations used: HSCCC: High-Speed Counter-Current Chromatography; LC-MS: Liquid Chromatograph-Mass Spectrometer; NMR: Nuclear Magnetic Resonance; TCM: Traditional Chinese Medicine; HPLC: High Performance Liquid Chromatography; ESI-MS: Electrospray Ionization Mass Spectrometry; PE: petroleum ether.

Keywords: High-speed counter-current chromatography; Tussilago farfara L.; preparation; sesquiterpenoids; solvent selection.