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]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  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-. doi: 10.3866/PKU.WHXB202408015
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  Jingming Li , Bowen Ding , Nan Li , Nurgul . Application of Comparative Teaching Method in Experimental Project Design of Instrumental Analysis Course: A Case Study in Chromatography Experiment Teaching. University Chemistry, 2024, 39(8): 263-269. doi: 10.3866/PKU.DXHX202312078
13. [13]
  Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095
14. [14]
  Lan Ma , Cailu He , Ziqi Liu , Yaohan Yang , Qingxia Ming , Xue Luo , Tianfeng He , Liyun Zhang . Magical Surface Chemistry: Fabrication and Application of Oil-Water Separation Membranes. University Chemistry, 2024, 39(5): 218-227. doi: 10.3866/PKU.DXHX202311046
15. [15]
  Haoxiang Zhang , Zhihan Zhao , Yongchen Jin , Zhiqiang Niu , Jinlei Tian . Synthesis of an Efficient Absorbent Gel: A Recommended Comprehensive Chemistry Experiment. University Chemistry, 2024, 39(11): 251-258. doi: 10.12461/PKU.DXHX202401084
16. [16]
  Ling Bai , Limin Lu , Xiaoqiang Wang , Dongping Wu , Yansha Gao . Exploration and Practice of Teaching Reforms in “Quantitative Analytical Chemistry” under the Perspective of New Agricultural Science. University Chemistry, 2024, 39(3): 158-166. doi: 10.3866/PKU.DXHX202308101
17. [17]
  Yujia LI , Tianyu WANG , Fuxue WANG , Chongchen WANG . Direct Z-scheme MIL-100(Fe)/BiOBr heterojunctions: Construction and photo-Fenton degradation for sulfamethoxazole. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 481-495. doi: 10.11862/CJIC.20230314
18. [18]
  Yanhui Zhong , Ran Wang , Zian Lin . Analysis of Halogenated Quinone Compounds in Environmental Water by Dispersive Solid-Phase Extraction with Liquid Chromatography-Triple Quadrupole Mass Spectrometry. University Chemistry, 2024, 39(11): 296-303. doi: 10.12461/PKU.DXHX202402017
19. [19]
  Jiahong ZHENG , Jiajun SHEN , Xin BAI . Preparation and electrochemical properties of nickel foam loaded NiMoO₄/NiMoS₄ composites. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 581-590. doi: 10.11862/CJIC.20230253
20. [20]
  Zunyuan Xie , Lijin Yang , Zixiao Wan , Xiaoyu Liu , Yushan He . Exploration of the Preparation and Characterization of Nano Barium Titanate and Its Application in Inorganic Chemistry Laboratory Teaching. University Chemistry, 2024, 39(4): 62-69. doi: 10.3866/PKU.DXHX202310137

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(399)
HTML views(53)

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