Preparative Separation of Alkaloids from Picrasma quassioides (D. Don) Benn. by Conventional and pH-Zone-Refining Countercurrent Chromatography
Abstract
:1. Introduction
2. Results Discussion
2.1. Optimization of HPLC Conditions
2.2. Separation of the Crude Extract of Picrasma quassioides by Conventional HSCCC
Solvent System (Pet–EtOAc–MeOH–H2O) (v/v) | KDa | KDb | KDc | KDe | KDf | KDg |
---|---|---|---|---|---|---|
5:5:5:5 | 0.18 | 0.26 | 1.34 | 0.96 | 0.64 | 1.72 |
5:5:4.5:5.5 | 0.24 | 0.48 | 2.24 | 1.82 | 1.45 | 2.68 |
5:5:4:6 | 0.47 | 0.96 | 3.12 | 2.41 | 1.96 | 3.44 |
2.3. Separation of the Crude Extract of Picrasma quassioides by pH-Zone-Refining CCC
HSCCC | pH-Zone-Refining CCC | |||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|
a | b | c | e | f | g | a | b | c | d | e | f | |
Purity (%) | 93.4 | 95.7 | 96.1 | 95.4 | 97.7 | 97.1 | 98.1 | 98.2 | 98.4 | 98.7 | 99.1 | 98.1 |
Yield (mg) | 4 | 8 | 13 | 8 | 11 | 14 | 87 | 38 | 76 | 74 | 56 | 26 |
Recovery (%) | 76 | 82 | 92 | 78 | 72 | 94 | 94 | 92 | 94 | 96 | 95 | 91 |
sample size | 200 mg | 2 g |
3. Experimental
3.1. Reagents and Materials
3.2. Apparatus
3.3. Preparation of Crude Extract
3.4. Separation Procedure
3.5. HPLC Analysis and Identification of CCC Fractions
3.6. Identification of Isolated Compounds
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
- Chinese Material Medical Committee. Zhonghua Bencao, 2nd ed.; Shanghai Science and Technology Press: Shanghai, China, 1998; pp. 7–10. [Google Scholar]
- Pharmacopoeia Committee. Pharmacopoeia of the People’s Republic of China; China Medical Science and Technology Press: Beijing, China, 2010; Volume 1, pp. 186–188. [Google Scholar]
- Sung, Y.I.; Koike, K. Inhibitors of cyclic AMP phosphor-di-esterase in Picrasma quassiodes (D. Don) Benn. and inhibitory activity of related alkaloids. Chem. Pharm. Bull. 1984, 32, 1872–1877. [Google Scholar] [CrossRef]
- Jia, C.; Xiao, H.Y. Tabacco Mosaic Virus (TMV) Inhibitors from Picrasma quassioides Benn. Agric. Food Chem. 2009, 57, 6590–6595. [Google Scholar] [CrossRef]
- Ito, Y. Golden rules and pitfalls in selecting optimum conditions for high-speed counter-currentchromatography. J. Chromatogr. A 2005, 1065, 145–158. [Google Scholar] [CrossRef]
- Ito, Y. pH-zone-refining counter-current chromatography: Origin, mechanism, procedure and applications. J. Chromatogr. A 2013, 1271, 71–85. [Google Scholar] [CrossRef]
- Liu, Y.Q.; Guo, X.F.; Duan, W.J.; Wang, X.; Du, J.H. Accelerated solvent extraction of monacolin K from red yeast rice and purification by high-speed counter-current chromatography. J. Chromatogr. B 2010, 878, 2881–2885. [Google Scholar] [CrossRef]
- Wang, X.; Wang, Y.Q.; Yuan, J.P.; Sun, Q.L.; Liu, J.H.; Zheng, C.C. An efficient new method for extraction, separation and purification of psoralen and isopsoralen from Fructus Psoraleae by supercritical fluid extraction and high-speed counter-current chromatography. J. Chromatogr. A 2004, 1055, 135–140. [Google Scholar] [CrossRef]
- Wang, X.; Geng, Y.L.; Li, F.W.; Shi, X.G.; Liu, J.H. Large-scale separation of alkaloids from Corydalis decumbens by pH-zone-refining counter-current chromatography. J. Chromatogr. A 2006, 1115, 267–270. [Google Scholar] [CrossRef]
- Zhu, Y.; Liu, Y.; Zhang, Y.; Liu, L.; Xu, Y.X.; Xu, Y.H.; Liu, T.H. Preparative isolation and purification of five flavonoid glycosides and one benzophenone galloyl glycoside from Psidium guajava by high-speed counter-current chromatography (HSCCC). Molecules 2013, 18, 15648–15661. [Google Scholar] [CrossRef]
- Wang, X.; Dong, H.J.; Shu, X.K.; Zheng, Z.J.; Yang, B.; Huang, L.Q. Large-scale separation of alkaloids from Corydalis bungeana turcz. by pH-zone-refining counter-current chromatography. Molecules 2012, 17, 14968–14974. [Google Scholar] [CrossRef]
- Zhao, W.N.; He, J.; Zhang, Y.M.; Ito, Y.; Su, Q.; Sun, W.J. Preparative isolation and purification of alkaloids from Picrasma quassiodes (D. Don) Benn. by high-speed countercurrent chromatography. J. Liq. Chromatogr. Relat. Technol. 2012, 35, 1597–1606. [Google Scholar]
- Taichi, O.; Kazuo, K. Studies on the constituents of Picrasma quassioides (D. Dom) Benn. II. On the alkaloidal constituents. Chem. Pharm. Bull. 1983, 31, 3198–3204. [Google Scholar] [CrossRef]
- Yan, L.L.; Li, S. Chemical constituents of Taraxacum formosanum. Chem. Pharm. Bull. 2003, 51, 599–601. [Google Scholar] [CrossRef]
- Taichi, O.; Kazuo, K. Studies on the constituents of Picrasma quassioides (D. Dom) Benn. I. On the alkaloidal constituents. Chem. Pharm. Bull. 1982, 30, 1204–1209. [Google Scholar] [CrossRef]
- Taichi, O.; Kazuo, K. Studies on the constituents of Picrasma quassioides (D. Dom) Benn. III. On the alkaloidal constituents. Chem. Pharm. Bull. 1984, 32, 3579–3583. [Google Scholar] [CrossRef]
- Yang, J.S.; Luo, S.R.; Shen, X.L.; Li, Y.X. The study of alkaloids from Picrasma quassioides (D. Dom) Benn. Acta Pharm. Sin. 1979, 3, 167–177. [Google Scholar]
- Sample Availability: Samples of the compounds are available from the authors.
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Zhang, Q.; Shu, X.; Jing, F.; Wang, X.; Lin, C.; Luo, A. Preparative Separation of Alkaloids from Picrasma quassioides (D. Don) Benn. by Conventional and pH-Zone-Refining Countercurrent Chromatography. Molecules 2014, 19, 8752-8761. https://doi.org/10.3390/molecules19078752
Zhang Q, Shu X, Jing F, Wang X, Lin C, Luo A. Preparative Separation of Alkaloids from Picrasma quassioides (D. Don) Benn. by Conventional and pH-Zone-Refining Countercurrent Chromatography. Molecules. 2014; 19(7):8752-8761. https://doi.org/10.3390/molecules19078752
Chicago/Turabian StyleZhang, Qinghai, Xikai Shu, Feng Jing, Xiao Wang, Changhu Lin, and Aiqin Luo. 2014. "Preparative Separation of Alkaloids from Picrasma quassioides (D. Don) Benn. by Conventional and pH-Zone-Refining Countercurrent Chromatography" Molecules 19, no. 7: 8752-8761. https://doi.org/10.3390/molecules19078752