Separation and Preparation of Five Cyclopamine Analogs from Rhizomes of Veratrum oxysepalum Turcz. by Two-Step High-Speed Counter-Current Chromatography

Separation Science and Technology (Philadelphia)

Volumn 49, Issue 17, 2014, Pages 2748-2755

  Yu, Yue ^a   Li, Huijun ^a   Jiang, Yan ^b  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

^b NANJING FORESTRY UNIVERSITY   (China)

Author keywords

cyclopamine analogs; high speed counter current chromatography; steroidal alkaloids; Veratrum oxysepalum

Indexed keywords

ALKALOIDS; DICHLOROMETHANE; HEXANE; MASS SPECTROMETRY; METABOLITES; METHANOL; NITROGEN COMPOUNDS; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

CYCLOPAMINE ANALOGS; ETHYL ACETATES; HIGH-SPEED COUNTER CURRENT CHROMATOGRAPHY; METHANOL-WATER; NUCLEAR MAGNETIC RESONANCE(NMR); TANDEM MASS SPECTROMETRY; TIME OF FLIGHT; VERATRUM OXYSEPALUM;

LIQUID CHROMATOGRAPHY;

EID: 84909987379     PISSN: 01496395     EISSN: 15205754     Source Type: Journal    
DOI: 10.1080/01496395.2014.942744     Document Type: Article

References (26)

1. Keller, R. F. (1978) Cyclopamine and related steroidal alkaloid teratogens: their occurrence, structural relationship, and biologic effects. Lipids, 13 (10): 708.
2. Bee, W. T.; Xie, W.; Truong, M.; Will, M.; Turunen, B.; Zuercher, W. J.; McMillan, L.; Li, H.; Hornberger, K. R.; Davenport, E. A.; Ames, R. S.; Kallal, L. A. (2012) The development of a high-content screening binding assay for the smoothened receptor. J. Biomol. Screen., 17 (7): 900.
3. Gould, A.; Missailidis, S. (2011) Targeting the Hedgehog Pathway: The development of cyclopamine and the development of anti-cancer drugs targeting the hedgehog pathway. Mini. Rev. Med. Chem., 11 (3): 200.
4. Sanchez, P.; Hernández, A. M.; Stecca, B.; Kahler, A. J.; DeGueme, A. M.; Barrett, A.; Beyna, M.; Datta, M. W.; Datta, S.; Ruizi Altaba, A. (2004) Inhibition of prostate cancer proliferation by interference with SONIC HEDGEHOG-GLI1 signaling. Proc. Natl. Acad. Sci. USA, 101 (34):12561.
5. Bar, E. E.; Stearns, D. (2008) New developments in medulloblastoma treatment: the potential of a cyclopamine–lovastatin combination. Expert. Opin. Investig. Drugs, 17 (2): 185.
6. Wu, X. Y.; Che, J.; Sun, K. K.; Shen, X. J.; Yang, D.; Zhong, N.; Zhao, H. (2013) Cyclopamine increases the radiosensitivity of human pancreatic cancer cells by regulating the DNA repair signal pathway through an epidermal growth factor receptor-dependent pathway. Mol. Med. Rep., 8 (4): 979.
7. ClinicalTrials.gov (Internet). (2013) Identifier NCT01255800. Pilot study of cetuximab and the hedgehog inhibitor IPI-926 in recurrent head and neck cancer. National Library of Medicine (US), Bethesda, Maryland. 2011 April–2014 April. URL [http://clinicaltrials.gov/show/NCT01255800], Accessed April 25, 2013.
8. Giannis, A.; Heretsch, P.; Sarli, V.; Stüßel, A. (2009) Synthesis of cyclopamine using a biomimetic and diastereoselective approach. Angew. Chem. Int. Ed., 48 (42): 7911.
9. Heretsch, P.; Rabe, S.; Giannis, A. (2009) Synthesis of all diastereomers of the piperidine alkaloid substructure of cyclopamine. Org. Lett., 11 (23): 5410.
10. Heretsch, P.; Tzagkaroulaki, L.; Giannis, A. (2010) Cyclopamine and hedgehog signaling: chemistry, biology, medical perspectives. Angew. Chem. Int. Ed., 49 (20): 3418.
11. Oatis Jr, J. E.; Brunsfeld, P.; Rushing, J. W.; Moeller, P. D.; Bearden, D. W.; Gallien, T. N.; Cooper IV, G. (2008) Isolation, purification, and full NMR assignments of cyclopamine from Veratrum californicum. Chem. Cent. J., 2: 12.
12. Jayatilake, G.S.; Richheimer, S.L.; Mann. D.A. Isolation of cyclopamine. U. S. Patent 20100003728, January 7, 2010.
13. Zhang, W. D.; Li, H. L.; Tang, J.; Zhang, C.; Su, J.; Shen, Y. H.; Liu, R. H. (2007) A conversion of jervine into cyclopamine. Chinese Patent 101016329, August 15, 2007.
14. Li, H. J.; Jiang, Y.; Li, P. (2006) Chemistry, bioactivity and geographical diversity of steroidal alkaloids from the Liliaceae family. Nat. Prod. Rep., 23: 735.
15. Wang, B.; Zhang, W. D.; Shen, Y. H.; Tang, J.; Zhang, C.; Liu, R. H.; Lin, M.; Li, H. L. (2008) Two new steroidal alkaloids from Veratrum nigrum L. Helv. Chim. Acta., 91 (2): 244.
16. Sun, Y.; Chen, J. X.; Zhou, L.; Su, J.; Li, Y.; Qiu, M. H. (2012) Three new pregnane alkaloids from Veratrum taliense. Helv. Chim. Acta., 95 (7): 1114.
17. Tang, J.; Li, H. L.; Huang, H. Q.; Zhang, W. D. (2006) Progress in the research on chemical constituents of Veratrum plants. Progr. Pharm. Sci., 30 (5): 206.
18. Editorial Committee of Chinese Bencao of the State Administration of Traditional Chinese Medicine. (1999) Selected Works of Chinese Bencao, Vol. 2, Shanghai Science and Technology Press, Shanghai, China; p. 183.
19. Hostettmann, K.; Marston, A. (2001) Countercurrent chromatography in the preparative separation of plant-derived natural products. J. Liq. Chromatogr. R. T., 24 (11–12): 1711.
20. Marston, A.; Hostettmann, K. (2006) Developments in the application of counter-current chromatography to plant analysis. J. Chromatogr. A, 1112 (1–2): 181.
21. Sutherland, I. A.; Fisher, D. (2009) Role of counter-current chromatography in the modernization of Chinese herbal medicines. J. Chromatogr. A, 1216 (4): 740.
22. Ito, Y. (2005) Golden rules and pitfalls in selecting optimum conditions for high-speed counter-current chromatography. J. Chromatogr. A, 1065 (2): 145.
23. das Neves Costa, F.; Guimaraes Leitao, G. (2010) Strategies of solvent system selection for the isolation of flliavonoids by countercurrent chromatography. J. Sep. Sci., 33 (3): 336.
24. Fang, L.; Liu, Y.Q.; Yang, B.; Wang, X.; Huang, L. Q. (2011) Separation of alkaloids from herbs using high-speed counter-current chromatography. J. Sep. Sci., 34 (19): 2545.
25. Chandler, C. M.; Habig, J. W.; Fisher, A. A.; Ambrose, K. V.; Jiménez, S. T.; McDougal, O. M. (2013) Improved extraction and complete mass spectral characterization of steroidal alkaloids from Veratrum californicum, Nat. Prod. Commun., 8 (0): 1.
26. Cong, Y.; Wang, J. H.; Wang, R.; Zeng, Y. M.; Liu, C. D.; Li, X. (2008) A study on the chemical constituents of Veratrum nigrum L. processed by rice vinegar, J. Asian Nat. Prod. Res., 10 (7): 616.