Preparative isolation and purification of epothilones from sorangium cellulosum fermentation broth by high-speed counter-current chromatography

Journal of Liquid Chromatography and Related Technologies

Volumn 38, Issue 1, 2015, Pages 123-127

  Yang, Huangjian ^a   Zhang, Zhulan ^a   Tang, Wenli ^a   Ren, Linying ^a   Wang, Desen ^a   Sun, Fei ^a   Zheng, Wei ^a  

^a FUJIAN INSTITUTE OF MICROBIOLOGY   (China)

Author keywords

1H NMR; epothilones; ESI MS; high speed counter current chromatography (HSCCC); identification; separation

Indexed keywords

SEPARATION;

EPOTHILONES; ESI-MS; FERMENTATION BROTHS; HIGH-SPEED COUNTER-CURRENT CHROMATOGRAPHY; PREPARATIVE ISOLATION; SORANGIUM CELLULOSUM;

IDENTIFICATION (CONTROL SYSTEMS);

ACETIC ACID ETHYL ESTER; EPOTHILONE A; EPOTHILONE B; EPOTHILONE DERIVATIVE; HEXANE; METHANOL; SOLVENT; WATER;

ARTICLE; BACTERIAL STRAIN; COUNTER CURRENT CHROMATOGRAPHY; ELECTROSPRAY MASS SPECTROMETRY; FERMENTATION; FLOW RATE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HIGH SPEED COUNTER CURRENT CHROMATOGRAPHY; ISOLATION AND PURIFICATION; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SORANGIUM CELLULOSUM; ULTRAVIOLET SPECTROSCOPY;

EID: 84907696664     PISSN: 10826076     EISSN: 1520572X     Source Type: Journal    
DOI: 10.1080/10826076.2014.883541     Document Type: Article

References (24)

1. Hofle, G.; Bedorf, N.; Gerth, K.; Reichenbach, H. Epothilones, Process for Preparing the Same and Their Use as Medicaments and as Plant Protecting Agents. German Patent D.E.4,138,042, 1993.
2. Gerth, K.; Bedorf, N.; Hofle, G.; Irschik, H.; Reichenbach, H. Epothilons A and B: Antifungal and Cytotoxic Compounds from Sorangium cellulosum (Myxobacteria). Production, Physico-Chemical and Biological Properties. J. Antibiot. 1996, 49, 560-563.
3. Hofle, G.; Bedorf, N.; Steinmetz, I. H.; Schomburg, D.; Gerth, K.; Reichenbach, H. Epothilone A and B-Novel 16-Membered Macrolides with Cytotoxic Activity: Isolation, Crystal Structures, and Conformation in Solution. Angew. Chem. Int. Ed. Engl. 1996, 35, 1567-1569.
4. Hardt, I. H.; Steinmetz, H.; Gerth, K.; Sasse, F.; Reichenbach, H.; Höfle, G. New Natural Epothilones from Sorangium cellulosum, Strains So ce90=B2 and So ce90=D13: Isolation, Structure Elucidation, and SAR Studies. J. Nat. Prod. 2001, 64, 847-856.
5. Arslanian, R. L.; Tang, L.; Blough, S.; Ma, W.; Qiu, R.-G.; Katz, L.; Carney, J. R. A New Cytotoxic Epothilone from Modified Polyketide Synthases Heterologously Expressed in Myxococcus xanthus. J. Nat. Prod. 2002, 65, 1061-1064.
6. Starks, C. M.; Zhou, Y.; Liu, F.; Licari, P. J. Isolation and Characterization of New Epothilone Analogues from Recombinant Myxococcus xanthus Fermentations. J. Nat. Prod. 2003, 66, 1313-1317.
7. Wang, J.-D.; Zhang, H.; Ying, L.-P.; Wang, C.-X.; Jiang, N.; Zhou, Y.; Wang, H.-B.; Bai, H. Five New Epothilone Metabolites from Sorangium cellulosum Strain So0157-2. J. Antibiot. 2009, 62, 483-487.
8. Hofle, G.; Steinmetz, H. Epothilones C, D, E and F, Preparation and Compositions. US. Patent 7,067,544, B2, 2006.
9. Nicolaou, K. C.; He, Y.; Ninkovic, S.; Pastor, J.; Roschangar, F.; Sarabia, F.; Vallerg, H.; Vourloumis, D.; Winssinger, N.; Yang, Z.; King, N. P.; Finlay, M. Y. Epothilone Analogs. US. Patent 7,173,137, B2, 2007.
10. Lee, J. J.; Swain, S. M. The epothilones: Translating from the laboratory to the clinic. Clin. Cancer Res. 2008, 14, 1618-1624.
11. Argyriou, A. A.; Marmiroli, P.; Cavaletti, G.; Kalofonos, H. P. Epothilone-Induced Peripheral Neuropathy: A Review of Current Knowledge. J. Pain Symp. Manag. 2011, 42 (6), 931-940.
12. Rogalska, A.; Szula, E.; Gajek, A.; Marczak, A.; Jóźwiak, Z. Activation of Apoptotic Pathway in Normal, Cancer Ovarian Cells by Epothilone B. Environ. Toxicol. Pharmacol. 2013, 36, 600-610.
13. Benigni, D.; Stankavage, R.; Chiang, S.-J.; Hou, H.; Eagan, B.; Gu, D.; Hou, D.; Mintzmyer, L.; Tully, T P.; Davis, B. L.; Hargro, I.; Mascari, M.; Galvin, G.; Stein, G.; McConlogue, C. W.; Comezoglu, F. T. Methods for the Preparation, Isolation and Purification of Epothilone B, and X-Ray Crystal Structures of Epothilone B. US. Patent 0122891,A1, 2007.
14. Ito, Y. Efficient Preparative Counter-Current Chromatography with a Coil Planet Centrifuge. J. Chromatogr. 1981, 214, 122-125.
15. Zheng, W. Separation of Cyclosporins and Other Antibiotics by HSCCC. J. Chromatogr. Sci. 2009, 47, 354.
16. Fu, Y.; Li, Z.-Y.; Si, J. Y.; Chang, Q.; Li, Z.; Pan, R. Separation and Purification of Myricitrin from Bayberry Tree Bark by High Speed Counter-Current Chromatography. J. Liq. Chromatogr. Rel. Technol. 2013, 36 (11), 1503-1512.
17. Tan,X.; Tan,D.-M.; Brown, L.;Yang,D.-P.; Zhu, L.-P.; Chen, Y.-L; Chang, D. H.; Wang, D.-M. Isolation and Purification of Four Bioactive Constituents from Alpinia officinarum Hance Utilizing High-Speed Counter-Current Chromatography. J. Liq. Chromatogr. Rel. Technol. 2013, 36 (10), 1355-1365.
18. Yang, Y.; Bakri, M.; Gu, D.-Y.; Aisa, H. A. Separation of (s)-Dehydrovomifoliol from Leaves of nitrrla sibirica pall. by High-Speed Counter-Current Chromatography. J. Liq. Chromatogr. Rel. Technol. 2013, 36 (5), 573-582.
19. Li, X.; Sun, A.-L.; Liu, R.-M.; Zhang, Y.-Q. Preparative Separation and Purification of Biondnoid I and Magnolin from the Chinese Medicinal Plant flos magnoliae. by High-Speed Counter-Current Chromatography. J. Liq. Chromatogr. Rel. Technol. 2012, 35 (16), 2304-2312.
20. Li, A.-F.; Sun, A.-L.; Liu, R.-M. Preparative Isolation and Purification of Three Flavonoids from the Chinese Medicinal Plant Alpinia Katsumadai hayata by High-Speed Counter-Current Chromatography. J. Liq. Chromatogr. Rel. Technol. 2012, 35 (20), 2900-2909.
21. Wang, J.-D.; Jiang, N.; Zhang, H.; Ying, L.-P.; Wang, C.-X.; Xiang, W.-S.; Wu, B.; Wang, H.-B.; Bai, H. New Epothilone Congeners from Sorangium cellulosum Strain So0157-2. J. Nat. Prod. 2011, 25, 1707-1712.
22. Cao, X. L. Isolation Technology and Application of High-speed Counter-Current Chromatography, Chemical Industry Press: Beijing, 2004.
23. Ito, Y. Golden Rules and Pitfalls in Selecting Optimum Conditions for High-Speed Counter-Current Chromatography. J. Chromatogr A. 2005, 1065, 145-168.
24. Chen, L. J.; Games, D. E.; Jones, J. Isolation and Identification of Four Flavonoid Constituents from the Seeds of Oroxylum indicum by High-Speed Counter-Current Chromatography. J. Chromatogr. A 2003, 988, 595.