Purity-activity relationships of natural products: The case of anti-TB active ursolic acid

Journal of Natural Products

Volumn 71, Issue 10, 2008, Pages 1742-1748

  Jaki, Birgit U ^a   Franzblau, Scott G ^a   Chadwick, Lucas R ^a,b   Lankin, David C ^a   Zhang, Fangqiu ^a,c   Wang, Yuehong ^a   Pauli, Guido F ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^b Cherry Instruments   (United States)

^c Sanofi Pasteur   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BETULIC ACID; NATURAL PRODUCT; OLEANOLIC ACID; TUBERCULOSTATIC AGENT; URSOLIC ACID;

ANIMAL CELL; ANTIBACTERIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACTIVITY; DRUG PURITY; DRUG RESEARCH; DRUG STRUCTURE; IC 50; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE STRUCTURE ACTIVITY RELATION; VERO CELL;

ANIMALS; ANTITUBERCULAR AGENTS; BIOLOGICAL PRODUCTS; CERCOPITHECUS AETHIOPS; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; MYCOBACTERIUM TUBERCULOSIS; STRUCTURE-ACTIVITY RELATIONSHIP; TRITERPENES; VERO CELLS;

MYCOBACTERIUM TUBERCULOSIS;

EID: 56049104447     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np800329j     Document Type: Article

References (53)

1. Newman, D. J.; Cragg, G. M.; Snader, K. M. Nat. Prod. Rep. 2000, 17, 215-234.
2. Newman, D. J.; Cragg, G. M.; Snader, K. M. J. Nat. Prod. 2003, 66, 1022-1037.
3. Newman, D. J.; Cragg, G. M. J. Nat. Prod. 2007, 70, 461-477.
4. Lill, M. A. Drug Discovery Today 2007, 12, 1013-1017.
5. U.S. Food and Drug Administration. Guidance for Industry. Q3A Impurities in New Drug Substances. http://www.fda.gov/cber/gdlns/ichq3a.htm#v (accessed May 31, 2008).
6. Farnsworth, N. R. The NAPRALERT database. Available on-line through the Scientific and Technical Network (STN) of Chemical Abstracts Service, Columbus, OH, 2007.
7. Braghiroli, L.; Mazzanti, G.; Manganaro, M.; Mascellino, M. T.; Vespertilli, T. Phytother. Res. 1996, 10, S86-S88.
8. Mathuram, V.; Bhahmadhayalaselvam, A.; Jaffar Hussain, A.; Bhima Rao, R.; Patra, A. J. Ind. Chem. Soc. 1998, 75, 262-264.
9. Richards, R. M.; Durham, D. G.; Liu, X. Planta Med. 1994, 60, 471-473.
10. Takechi, M.; Tanaka, Y. Phytochemistry 1993, 34, 675-677.
11. Panizzi, L.; Catalano, S.; Miarelli, C.; Pioni, P. I.; Campeol, E. Phytother. Res 2000, 14, 561-563.
12. Kuroyanagi, M.; Ebihara, T.; Tsukamoto, K.; Fukushima, S.; Ishizeki, C.; Satake, M. Screening of antibacterial constituents of crude drugs and plants; 5th Symposium on development and application of naturally occuring drug materials; Japan, 1984.
13. Haraguchi, H.; Kataoka, S.; Okamoto, S.; Hanafi, M.; Shibata, K. Phytother. Res. 1999, 12, 151-156.
14. Osawa, K.; Yasuda, H.; Morita, H.; Takeya, K.; Itokawa, H. Nat. Med. 1997, 51, 365-367.
15. Gonzales, B.; Suarez Roca, H.; Bravo, A.; Salas Auvert, R.; Avila, D. Pharm. Biol. 2000, 38, 287-290.
16. Miura, N.; Matsumoto, Y.; Miyairi, S.; Nishiyama, S.; Naganuma, A. Mol. Pharmacol. 1999, 56, 1324-1328.
17. Ahn, K. S.; Hahm, M. S.; Park, E. J.; Lee, H. K.; Kim, E. H. Planta Med. 1998, 64, 468-470.
18. Manez, S.; Recio, M. C.; Giner, R. M.; Rios, J. L. Eur. J. Pharmacol. 1997, 334, 103-105.
19. Huang, M. T.; Ho, C. T.; Wang, Z. Y.; Ferraro, T.; Lou, Y. R.; Stauber, K.; Ma, W.; Georgiadis, C.; Laskin, J. D.; Conney, A. H. Cancer Res. 1994, 54, 701-708.
20. Huguet, A. I.; Del Carmen Recio, M.; Manez, S.; Giner, R. M.; Rios, J. L. Eur. J. Pharmacol. 2000, 410, 69-81.
21. Yasukawa, K.; Takido, M.; Takeuchi, M.; Nakagawa, S. Chem. Pharm. Bull. 1989, 37, 1071-1073.
22. Umehara, K.; Takagi, R.; Kuroyanagi, M.; Ueno, A.; Taki, T.; Chen, Y. J. Chem. Pharm. Bull. 1992, 40, 401-405.
23. Liu, J. J. Ethnopharmacol. 1995, 49, 57-68.
24. Ali, R. M.; Houghton, P. J. Planta Med. 1999, 65, 455-457.
25. Simon, A.; Najid, A.; Chulia, A. J.; Delage, C.; Rigaud, M. Biochim. Biophys. Acta 1992, 1125, 68-72.
26. Ma, X. H.; Zhao, Y. C.; Yin, L.; Xu, R. L.; Han, D. W.; Wang, M. S. Yao Hsueh Hsue Pao 1986, 21, 332-335.
27. Okuyama, E.; Yamazaki, M.; Ishii, Y. Shoyakugaku Zasshi 1983, 37, 52-55.
28. Kim, D. W.; Bang, K. H.; Rhee, Y. H.; Lee, K. T.; Park, H. J. Arch. Pharm. Res. 1998, 21, 688-691.
29. Lee, K. H.; Lin, Y. M.; Wu, T. S.; Zhang, D. C.; Yamagishi, T.; Hayashi, T.; Hall, I. H.; Chang, J. j.; Wu, R. Y.; Yang, T. H. Planta Med 1988, 54, 308-311.
30. Han, G. Q.; Che, C. T.; Fong, H. H. S.; Farnsworth, N. R.; Phoebe, C. H. J. Fitoterapia 1988, 59, 242-244.
31. Numata, A.; Takahashi, C.; Miyamoto, T.; Yoneda, M.; Yang, P. Chem. Pharm. Bull. 1990, 38, 942-944.
32. Pauli, G. F.; Jaki, B. U.; Lankin, D. C.; Walter, J. A.; Burton, I. W. Quantitative NMR (qNMR) of Bioactive Natural Products in Bioactive Natural Products: Detection, Isolation and Structural Determination, 2nd ed.; Colegate, S. M., Molyneux, R. J., Eds.; Taylor & Francis: New York, 2008.
33. Pauli, G. F.; Jaki, B.; Lankin, D. J. Nat. Prod. 2007, 70, 589-595.
34. Schühly, W.; Heilmann, J.; Calis, I.; Sticher, O. Planta Med. 1999, 65, 740-743.
35. Isobe, T.; Noda, Y.; Ohsaki, A.; Sakanaka, S.; Kim, M.; Taniguchi, M. Yakugaku Zasshi 1989, 109, 175-178.
36. Cantrell, C. L.; Franzblau, S. G.; Fischer, N. H. Planta Med. 2001, 67, 685-694.
37. Copp, B. R.; Pearce, A. N. Nat. Prod. Rep. 2007, 24, 278-297.
38. Newton, S. M.; Lau, C.; Wright, C. W. Phytother. Res. 2000, 14, 303-322.
39. Weiss, R.; Seebacher, W. Magn. Reson. Chem. 2002, 40, 455-457.
40. Pauli, G. F. Phytochem. Anal. 2001, 12, 28-42.
41. Pauli, G. F.; Jaki, B.; Lankin, D. J. Nat. Prod 2005, 68, 133-149.
42. Berthod, A.; Friesen, J. B.; Inui, T.; Pauli, G. F. Anal. Chem. 2007, 79, 3371-3382.
43. Ito, Y. J. Chromatogr. A 2005, 1065, 145-168.
44. Berthod, A. Countercurrent Chromatography: The Support-free Liquid Stationary Phase, 1st ed.; Elsevier: Amsterdam, 2002; Vol. 38.
45. Friesen, J. B.; Pauli, G. F. J. Agric. Food Chem. 2008, 56, 19-28.
46. Friesen, J. B.; Pauli, G. F. J. Liq. Chromatogr. Relat. Technol. 2005, 28, 2877-2808.
47. Friesen, J. B.; Pauli, G. F. J. Chromatogr. A 2007, 1151, 51-59.
48. Inui, T.; Wang, Y.; Deng, S.; Smith, D.; Franzblau, S.; Pauli, G. F. J. Chromatogr. A 2007, 1151, 211-215.
49. Tanrisever, N. Plant Germination and Growth Inhibitors from Ceratiola ericoides and Calamintha ashei; Louisiana State University: Baton Rouge, 1986.
50. Raduner, S.; Bisson, W.; Abagyan, R.; Altmann, K. H.; Gertsch, J. J. Nat. Prod. 2007, 70, 1010-1015.
51. Tanachatchairatana, T.; Bremner, J. B.; Chokchaisiri, R.; Suksamrarn, A. Chem. Pharm. Bull. 2008, 56, 194-198.
52. Changsen, C.; Franzblau, S. G.; Palittapongampim, P. Antimicrob. Agents Chemother. 2003, 47, 3682-3687.
53. Collins, L.; Franzblau, S. Antimicrob. Agents Chemother. 1997, 41, 1004-1009.