Preparative-scale separation of anticancer triterpenes from Eucalyptus hybrid by centrifugal partition chromatography

Separation Science and Technology

Volumn 46, Issue 7, 2011, Pages 1189-1194

  Maurya, Anupam ^a   Srivastava, Santosh Kumar ^a  

^a CSIR CENTRAL INSTITUTE OF MEDICINAL AND AROMATIC PLANTS   (India)

Author keywords

Centrifugal partition chromatography; Eucalyptus hybrid; Preparative chromatography; Ursolic acid; Ursolic acid lactone

Indexed keywords

AMMONIA SOLUTION; AQUEOUS MOBILE PHASE; CENTRIFUGAL-PARTITION CHROMATOGRAPHY; EUCALYPTUS HYBRID; MYRTACEAE; PREPARATIVE CHROMATOGRAPHY; TOTAL YIELD; TRITERPENES; TWO-PHASE SOLVENT SYSTEM; URSOLIC ACID;

LIQUID CHROMATOGRAPHY;

CENTRIFUGATION;

EID: 79957910677     PISSN: 01496395     EISSN: 15205754     Source Type: Journal    
DOI: 10.1080/01496395.2010.545793     Document Type: Article

References (32)

1. Srivastava, S.K.; Khan, M.; Khanuja, S.P.S. (2005) Process for isolation of anticancer agent camptothecin from Nothapodytes foetida. U.S. Patent 68,936,698, 2005.
2. Tanachatchairatana, T.; Bremner, J.B.; Chokchaisiri, R.; Suksamrarn, A. (2008) Antimycobacterial activity of cinnamate-based esters of the triterpenes betulinic, oleanolic and ursolic acids. Chem. Pharm. Bull., 56: 194.
3. Sparg, S.G.; Light, M.E.; Vanstadan, J. (2004) Biological activities and distribution of plant saponins. J. Ethnopharmacol., 94: 219.
4. Fukuda, Y.; Sakai, K.; Matsunaga, S.; Tokuda, H.; Tanaka, R. (2006) Cancer chemopreventive effect of orally administrated lupane-type triterpenoid on ultraviolet light B induced photocarcinogenesis of hairless mouse. Cancer Lett., 240: 94.
5. Novotny, L.; Vachalkaova, A.; Biggs, D. (2001) Ursolic acid: an anti-tumorigenic and chemopreventive activity. Neoplasma, 48: 241.
6. Haridas, V.; Arntzen, C.; Gutterman, J.U. (2001) Avicins, a family of triterpenoid saponins from Acacia victoriae (Bentham), inhibit activation of nuclear factor-kappaB by inhibiting both its nuclear localization and ability to bind DNA. J. Proceed. Nat. Acad. Sci. U.S.A., 98: 11557.
7. Vasconcelos, M.A.; Royo, V.A.; Ferreira, D.S.; Crotti, A.E.; Andrade e Silva, M.L. (2006) I vivo analgesic and antiinflamatory activities of ursoloic acid and oleonilic acid from Miconia albicans. Zeitschriff fur Naturforschung, 61: 477.
8. Kasiwada, Y.; Nagao, T.; Hashimoto, A.; Ikeshiro, Y.; Okabe, H.; Cosentino, L.M.; Lee, K.H. (2006) Anti AIDS agents, Anti-HIV activity of 3-O-acyl ursolic acid derivatives. J. Nat. Prod., 63: 1619.
9. Morton, J.F. (1981) Atlas of Medicinal Plants of Middle America, Bahamas to Yucatan; C.C., Thomas: Springfield, IL.
10. Nadkarni, K.M. (1976) Indian Materia Medica; Popular Prakashan: Bombay.
11. Dayal, R. (1990) Two new compounds from ursolic acid lactone. Ind. J. Chem., 29B: 156.
12. Lee, K.; Lin, Y.; Wu, T.; Zhang, D.; Yamagishi, T. (1988) The cytotoxic principles of Prunella vulgaris, Psychotria serpens, and Hyptis capitata: Ursolic acid and related derivatives. Planta Med., 54: 308.
13. Chen, G.; Yao, Z.; Zheng, W.; Chen, L.; Duan, H.; Shen, Y. (2010) Combined antitumor effect of ursolic acid and 5-fluorouracil on human esophageal carcinoma cell Eca-109 in vitro. Chin. J. Cancer Res., 22: 62.
14. Yoshida, M.; Fuchigami, M.; Nagao, T.; Okabe, H.; Matsunaga, K. (2005) Antiproliferative constituents from Umbelliferae plants VII. Active triterpenes and rosmarinic acid from Centella asiatica. Biol. Pharm. Bull., 28: 173.
15. Banno, N.; Akihisa, T.; Tokuda, H.; Yasukawa, K.; Taguchi, Y. (2005) Anti-inflammatory and antitumor-promoting effects of the triterpene acids from the leaves of Eriobotrya japonica. Biol. Pharm. Bull., 28: 1995.
16. Pelletier, S.W.; Venkov, A.P.J.F.M.; Mody, N.V. (1980) An alumina catalyzed addition of secondary amines to exocyclic a,b-unsaturated ketones. Tet. Lett., 21: 809.
17. Desai, H.K.; Joshi, B.S.; Ross, S.A.; Pelletier, S.W. (1989) Methanolysis of the C-8 acetoxyl group in aconitine-type alkaloids: A partial synthesis of hokbusine A. J. Nat. Prod., 52: 720.
18. Pelletier, S.W.; Desai, H.K.; Jiang, Q.; Ross, S.A. (1990) An unusual epimerization of the a-OH-1 group of the norditerpenoid alkaloid delphisine. Phytochemistry, 29: 3649.
19. Srivastava, S.K.; Desai, H.K.; Vobalaboina, V., Pelletier, S.W. (1999) Separation of diterpenoid alkaloids by high performance centrifugal partition chromatography. J. Liq. Chrom. Rel. Technol., 22: 1687.
20. Ito, Y.; Mandava, N.B.; Ito, Y. (Eds.) (1988) Countercurrent Chromatography: Theory and Practice; Marcel Dekker: New York, 79-442.
21. Conway, W.D.; Petroski, R.J. (Eds.) (1995) Modern Countercurrent Chromatography (ACS Symposium Series no. 593); American Chemical Society: Washington, DC.
22. Hostettmann, K.; Marston, A.; Hostettmann M. (1998) Preparative chromatography Techniques: Application in Natural Product Isolation, 2nd Ed.; Springer-Verlag: Berlin.
23. Berthod, A. (Ed.) (2003) Countercurrent Chromatography; Elsevier: Amsterdam.
24. Maurya, A.; Srivastava, S.K. (2009) Large-scale separation of clavinet alkaloids from Ipomoea muricata by pH-zone-refining centrifugal partition chromatography. J. Chromatogr. B, 877: 1732.
25. Maurya, A.; Gupta, S.; Negi, S.; Srivastava, S.K. (2009) pH-Zonerefining centrifugal partition chromatography for preparative isolation and purification of steroidal glycoalkaloids from Solanum xanthocarpum. J. Sep. Sci., 32: 3126.
26. Frighetto, N.; Welendorf, R.M.; Pereira da Silva, A.M.; Nakamura, M.J.; Siani, A.C. (2005) Purification of betulinic acid from Eugenia florida (Myrtaceae) by high-speed counter-current chromatography. Phytochem. Anal., 16: 411.
27. Frighetto, R.T.S.; Welendorf, R.M.; Nigro, E.N.; Frighetto, N.; Siani, A.C. (2008) Isolation of ursolic acid from apple peels by high speed counter-current chromatography. Food Chem., 106: 767.
28. Wu, S.; Sun, C; Wang, K.; Pan, Y. (2004) Preparative isolation and purification of celastrol from Celastrus orbiculatus Thunb. by a new counter-current chromatography method with an upright coil planet centrifuge. J Chromatogr. A, 1028: 171.
29. Rodrigo, R.O.; Gilda, G.L.; Michelle, C.C.M.; Maria, K.; Auxiliadora, C.; Daise, L.; Jorge, P.P.J. (2005) Gradient elution for triterpene separation from Cecropia lyratiloba Miquel by HSCCC. J. Liq. Chrom. Rel. Technol., 28: 1985.
30. Ito, Y. (2005) Golden rules and pitfalls in selecting optimum conditions for high-speed counter-current chromatography. J. Chromatogr. A, 1065: 145.
31. Seebacher, W.; Simic, N.; Weis, R.; Saf, R.; Kunert, O. (2003) Complete assignments of 1H and 13C NMR resonances of oleanolic acid, 18α-oleanolic acid, ursolic acid and their 11-oxo derivatives. Magn. Reson. Chem., 41: 636.
32. Hongcheng, W.; Yasuo, F. (1993) Triterpene esters from Eucalyptus tereticornis. Phytochemistry, 33: 151-153.