An efficient high‐speed counter‐current chromatography method for the preparative separation of sesquiterpenoids from the rhizomes of Cyperus rotundus L. combined with evaluation of the anti‐inflammation activity in vitro and molecular docking

Author:

Pan Shaobin1,Zhang Zhe1,Feng Qixiang1,Zhao Jin2,Aziz Shahid3,Dou Liwen1,Li Jing1,Huang Luyao1,Yan Huijiao3,Wang Xiao14,Li Jia1,Wang Daijie15ORCID

Affiliation:

1. College of Pharmacy Shandong University of Traditional Chinese Medicine Jinan P. R. China

2. Shandong Bluetown Analysis and Test Ltd. Jinan P. R. China

3. Department of Chemistry Mirpur University of Science and Technology Mirpur Pakistan

4. Shandong Analysis and Test Center Qilu University of Technology (Shandong Academy of Sciences) Jinan P. R. China

5. Biological Engineering Technology Innovation Center of Shandong Province Qilu University of Technology (Shandong Academy of Sciences) Heze P. R. China

Abstract

Cyperus rotundus L. has been extensively used in ancient medication for the treatment of different disorders worldwide, in which sesquiterpenes are the most representative components. In this study, sesquiterpenes were effectively purified by two‐dimensional counter‐current chromatography in combination with continuous injection and inner‐recycling mode with a solvent system of n‐hexane/ethyl acetate/methanol/water (1:0.2:1:0.2, v/v/v/v). For one‐dimension separation, continuous injection mode was used with three times injection and the inner‐recycling mode was adopted for the separation of two mixtures for two‐dimensional separation. Finally, four sesquiterpenoids, including scariodione (1), cyperenoic acid (2), scariodione (3), and α‐cyperone (4), were obtained with purities over 98%. Mass spectrometry and nuclear magnetic resonance were applied to identify their structures. The results from the anti‐inflammation effect with zebrafish demonstrated that cyperenoic acid exhibited stronger anti‐inflammation activity. Molecular docking results suggested that cyperenoic acid possessed lower binding energies –9.4545 kcal/mol with 1CX2 to form formed hydrogen bond interaction with ARG120. In general, all the obtained findings proved that the strong anti‐inflammation capacity of cyperenoic acid can have the potential of being adopted for treating diseases resulting from inflammation.

Funder

National Natural Science Foundation of China

Natural Science Foundation of Shandong Province

Publisher

Wiley

Subject

Filtration and Separation,Analytical Chemistry

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