Citation: LI Guozhu, MENG Qingyan, LUO Bi, GE Zhenhong, LIU Wenjie. Isolation of chemical constituents from Ziziphora clinopodioides Lam. with recycling preparative high performance liquid chromatography[J]. Chinese Journal of Chromatography, ;2015, 33(1): 84-89. doi: 10.3724/SP.J.1123.2014.09033 shu

Isolation of chemical constituents from Ziziphora clinopodioides Lam. with recycling preparative high performance liquid chromatography

1.
College of Life Science, Tarim University, Key Laboratory of Protection & Utilization of Biological Resources in Tarim Basin of Xinjiang Production and Construction Corps, Alar 843300, China

Corresponding author: LIU Wenjie,
Received Date: 22 September 2014
Available Online: 26 November 2014
Fund Project: 国家自然科学基金项目(21365018) (21365018)新疆生产建设兵团科技攻关项目(2011AB030) (2011AB030)新疆生产建设兵团塔里木盆地生物资源保护利用重点实验室开放课题(BRYB1404). (BRYB1404)

The combination of alternate recycling and direct recycling preparative liquid chromatography method was developed for the isolation of chemical constituents from Ziziphora clinopodioides Lam. The crude extract was obtained from Ziziphora clinopodioides Lam. by solvent extraction, column chromatography and reversed-phase (RP) flash chromatography. All the separations were performed with methanol and water as mobile phases and the developed recycling preparative method was used with twin RP columns switched by a two-position ten-way valve for the separation. The mobile phase was recycled in close loop with a two-position six-way valve. The fraction Ⅰ and fraction Ⅱ from reversed-phase flash chromatography were selected for the demonstration of separation power of the proposed protocol, and five compounds were obtained from Ziziphora clinopodioides Lam. The isolated five compounds were identified as pinocembrin-7-O-rutinoside, pinocembrin-7-O-rutinoside, acacetin-7-O-rutinoside, picein and protocatechuic acid with nuclear magnetic resonance (NMR). The experimental results showed that the developed preparation method exhibited higher separation efficiency with less mobile phase used than the reported methods, and could be expected as an effective method for the separation of complex natural products, especially the compounds with similar structures.
- alternate recycling,
- direct recycling,
- preparative liquid chromatography,
- chemical constituents,
- Ziziphora clinopodioides Lam.
1. [1]
  [1] Sharopov F S, Setzer W N. Nat Prod Commun, 2011, 6(5): 695
2. [2]
  [2] Ozturk S, Ercisli S. Food Control, 2007, 18(5): 535
3. [3]
  [3] Zhou X Y, Shi Y, Ma X M, et al. Research and Practice of Chinese Medicines (周晓英, 施洋, 马秀敏, 等. 现代中药研究与实践), 2011, 25(2): 44
4. [4]
  [4] Li N, Yang X J, Meng D L, et al. Journal of Shenyang Pharmaceutical University (李宁, 杨小菊, 孟大利, 等. 沈阳药科大学学报), 2009, 26(9): 691
5. [5]
  [5] Zhang P H, Ai Li S, Ji Q L, et al. Journal of Chinese Mass Spectrometry Society (张丕鸿, 艾力· 沙吾尔, 计巧灵, 等. 质谱学报), 2008, 29(3): 162
6. [6]
  [6] Nagai T, Mizobe H, Otake I, et al. J Chromatogr A, 2011, 1218(20): 2880
7. [7]
  [7] Qian K, Nakagawa-Goto K, Yu D, et al. Bioorg Med Chem Lett, 2007, 17(23): 6553
8. [8]
  [8] Watanabe K, Suzuki K, Kitamura S. Phytochemistry, 2006, 67(4): 338
9. [9]
  [9] Smith L R, Kubo I. J Nat Prod, 1995, 58(10): 1608
10. [10]
  [10] Ito J, Gobaru K, Shimamura T, et al. Tetrahedron, 1998, 54(24): 6651
11. [11]
  [11] Ren Q L, Dong X Y, Bao Z B. Chinese Journal of Chromatography (任其龙, 董新艳, 鲍宗必. 色谱), 2014, 32(5): 445
12. [12]
  [12] Bombaugh K J, Levangie R F. J Chromatogr Sci, 1970, 8(11): 657
13. [13]
  [13] Lan K, Jorgenson J W. Anal Chem, 1998, 70(14): 2773
14. [14]
  [14] Alley W R Jr, Mann B F, Hruska V, et al. Anal Chem, 2013, 85(21): 10408
15. [15]
  [15] Sidana J, Joshi L K. Chromatogr Res Int, 2013, 2013. DOI: 10.1155/2013/509812
16. [16]
  [16] Sidana J, Singh S, Arora K, et al. Fitoterapia, 2011, 82(7): 1118
17. [17]
  [17] Nakatsu T, Johns T, Kubo I, et al. J Nat Prod, 1990, 53(6): 1508
18. [18]
  [18] Xu X, Xie H, Hao J, et al. J Agric Food Chem, 2011, 59(4): 1205
19. [19]
  [19] Xie X Y, Su Y F, Chai X, et al. China Journal of Chinese Materia Medica (解笑瑜, 苏艳芳, 柴欣, 等. 中国中药杂志), 2009, 40(11): 1715
20. [20]
  [20] Qu G L, Zhang H M, Deng Z W, et al. Chinese Pharmaceutical Journal (曲功霖, 张海鸣, 邓志威, 等. 中国药学杂志), 2011, 46(2): 93
21. [21]
  [21] Ramadan M A, Ahmad A S, Nafady A M, et al. Nat Prod Res, 2009, 23(13): 1218
1. [1]
  Weiliang Wang , Zijing Yu , Jingyuan Li , Hong Shang . The Debate between Traditional Chinese Medicine and Western Medicine. University Chemistry, 2024, 39(9): 109-114. doi: 10.12461/PKU.DXHX202402001
2. [2]
  Yuan Zhuang , Wenhui Li , Jie Li . Curriculum Reform of “Chemical Composition Analysis of Materials” under Background of First-Class Discipline Construction. University Chemistry, 2025, 40(5): 283-290. doi: 10.12461/PKU.DXHX202407070
3. [3]
  Zhicheng JU , Wenxuan FU , Baoyan WANG , Ao LUO , Jiangmin JIANG , Yueli SHI , Yongli CUI . MOF-derived nickel-cobalt bimetallic sulfide microspheres coated by carbon: Preparation and long cycling performance for sodium storage. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 661-674. doi: 10.11862/CJIC.20240363
4. [4]
  Shanying Chen , Kangning Huo , Ke Qi , Jingyi Li , Shuxin Li , Yunchao Li . A Novel Colloid Electrophoresis Experiment with the Characteristics of Resource Recycling and Inquiry-Driven Experimental Design. University Chemistry, 2024, 39(5): 274-286. doi: 10.3866/PKU.DXHX202311067
5. [5]
  Ying Yang , Yonghan Wu , Zixuan Li , Lu Zhang , Rongqin Lin , Yefan Zhang , Jiquan Liu , Xiaohui Ning , Yan Li , Bin Cui . Visualization Simulation Experiment of Cyclic Voltammetry (CV) Based on Python. University Chemistry, 2025, 40(10): 233-242. doi: 10.12461/PKU.DXHX202412024
6. [6]
  Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
7. [7]
  Jie WU , Zhihong LUO , Xiaoli CHEN , Fangfang XIONG , Li CHEN , Biao ZHANG , Bin SHI , Quansheng OUYANG , Jiaojing SHAO . Critical roles of AlPO₄ coating in enhancing cycling stability and rate capability of high voltage LiNi_0.5Mn_1.5O₄ cathode materials. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 948-958. doi: 10.11862/CJIC.20240400
8. [8]
  Lijun Dong , Pengcheng Du , Guangnong Lu , Wei Wang . Exploration and Practice of Independent Design Experiments in Inorganic and Analytical Chemistry: A Case Study of “Preparation and Composition Analysis of Tetraammine Copper(II) Sulfate”. University Chemistry, 2024, 39(4): 361-366. doi: 10.3866/PKU.DXHX202310041
9. [9]
  Zunxiang Zeng , Yuling Hu , Yufei Hu , Hua Xiao . Analysis of Plant Essential Oils by Supercritical CO₂Extraction with Gas Chromatography-Mass Spectrometry: An Instrumental Analysis Comprehensive Experiment Teaching Reform. University Chemistry, 2024, 39(3): 274-282. doi: 10.3866/PKU.DXHX202309069
10. [10]
  Shunü Peng , Huamin Li , Zhaobin Chen , Yiru Wang . Simultaneous Application of Multiple Quantitative Analysis Methods in Gas Chromatography for the Determination of Active Ingredients in Traditional Chinese Medicine Preparations. University Chemistry, 2025, 40(10): 243-249. doi: 10.12461/PKU.DXHX202412043
11. [11]
  Houjin Li , Lin Wu , Xingwen Sun , Yuan Zheng , Zhanxiang Liu , Shuanglian Cai , Ying Xiong , Guangao Yu , Qingwen Liu , Jie Han , Xin Du , Chengshan Yuan , Qihan Zhang , Jianrong Zhang , Shuyong Zhang . Basic Operations and Specification Suggestions for Organic Chemical Chromatography Experiments. University Chemistry, 2025, 40(5): 93-105. doi: 10.12461/PKU.DXHX202408100
12. [12]
  Fan Wu , Wenchang Tian , Jin Liu , Qiuting Zhang , YanHui Zhong , Zian Lin . Core-Shell Structured Covalent Organic Framework-Coated Silica Microspheres as Mixed-Mode Stationary Phase for High Performance Liquid Chromatography. University Chemistry, 2024, 39(11): 319-326. doi: 10.12461/PKU.DXHX202403031
13. [13]
  Caixia Lin , Ting Liu , Zhaojiang Shi , Hong Yan , Keyin Ye , Yaofeng Yuan . Innovative Experiment of Electrochemical Dearomative Spirocyclization of N-Acyl Sulfonamides. University Chemistry, 2025, 40(4): 359-366. doi: 10.12461/PKU.DXHX202406107
14. [14]
  Qiuting Zhang , Fan Wu , Jin Liu , Zian Lin . Chromatographic Stationary Phase and Chiral Separation Using Frame Materials. University Chemistry, 2025, 40(4): 291-298. doi: 10.12461/PKU.DXHX202405174
15. [15]
  Linbao Zhang , Weisi Guo , Shuwen Wang , Ran Song , Ming Li . Electrochemical Oxidation of Sulfides to Sulfoxides. University Chemistry, 2024, 39(11): 204-209. doi: 10.3866/PKU.DXHX202401009
16. [16]
  Zhuoyan Lv , Yangming Ding , Leilei Kang , Lin Li , Xiao Yan Liu , Aiqin Wang , Tao Zhang . Light-Enhanced Direct Epoxidation of Propylene by Molecular Oxygen over CuO_x/TiO₂ Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 100038-0. doi: 10.3866/PKU.WHXB202408015
17. [17]
  Jinxin Guo , Shuyong Zhang , Rongxiu Zhu , Zhenghu Xu . Exploration and Practice of University Chemistry Laboratory Course Reform in the Context of Emerging Medical Education. University Chemistry, 2024, 39(8): 16-22. doi: 10.3866/PKU.DXHX202311062
18. [18]
  Yuanhong Zhang , Lin Jiang , Yanfang Wang , Chengxia Miao , Lili Zhang , Yijing Li , Junling Duan , Juying Hou , Qin Hou , Fuxian Wan . Exploration and Practice of Teaching Reform in Inorganic Chemistry within the New Agricultural Sciences Framework. University Chemistry, 2024, 39(8): 72-77. doi: 10.3866/PKU.DXHX202312060
19. [19]
  Xianyong Lu , Tao Hu . Developing an Innovative Inorganic Chemistry Teaching Model Based on Aerospace Specialty Characteristics. University Chemistry, 2025, 40(7): 127-131. doi: 10.12461/PKU.DXHX202409037
20. [20]
  Runjie Li , Hang Liu , Xisheng Wang , Wanqun Zhang , Wanqun Hu , Kaiping Yang , Qiang Zhou , Si Liu , Pingping Zhu , Wei Shao . 氨基酸的衍生及手性气相色谱分离创新实验. University Chemistry, 2025, 40(6): 286-295. doi: 10.12461/PKU.DXHX202407059

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(596)
HTML views(64)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142