Synthesis of argentatin A derivatives as growth inhibitors of human cancer cell lines in vitro

Bioorganic and Medicinal Chemistry Letters

Volumn 15, Issue 4, 2005, Pages 1005-1008

  Parra Delgado, Hortensia ^a   Ramírez Apan, Teresa ^a   Martínez Vázquez, Mariano ^a  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

Argentatin A; Cycloartane; Cytotoxicity

Indexed keywords

ARGENTATIN A; BROMINE; GROWTH INHIBITOR; ISOXAZOLE; KETONE DERIVATIVE; TRITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL CULTURE; CHEMICAL BOND; DRUG SYNTHESIS; GROWTH INHIBITION; HUMAN; HUMAN CELL; IN VITRO STUDY; SYNTHESIS; X RAY ANALYSIS;

EID: 16244413240     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.12.038     Document Type: Article

References (22)

1. J.D. Connolly, and R.A. Hill Nat. Prod. Rep. 12 1995 609
2. W. Tang, and G. Eisenbrand Chinese Drugs of Plant Origin: Chemistry, Pharmacology, and Use in Traditional and Modern Medicine 1992 Springer Berlin
3. M.T. Huang, C.T. Ho, Z.Y. Wang, T. Ferraro, Y.R. Lou, K. Stauber, W. Ma, C. Georgiadis, J.D. Laskin, and A.H. Conney Cancer Res. 51 1994 701
4. H.Y. Lee, H.Y. Chung, K.H. Kim, J.J. Lee, and K.W. Kim J. Cancer Res. Clin. Oncol. 120 1986 513
5. K.L. Sohn, H.Y. Lee, H.Y. Chung, H.S. Young, and K.W. Kim Cancer Lett. 94 1993 213
6. H.J. Cha, S.K. Bae, H.Y. Lee, O.H. Lee, H. Sato, M. Seiki, B.C. Park, and K.W. Kim Cancer Res. 56 1996 2281
7. S. Öksüz, H.-L. Shieh, J.M. Pezzuto, N. Özhatay, and G.A. Cordell Planta Med. 59 1993 472
8. I. Smith-Kielland, J.M. Dornish, K.E. Malterud, G. Hvistendahl, C. Romming, O.C. Bockman, P. Kolsaker, Y. Stenstrom, and A. Nordal Planta Med. 62 1996 322
9. A.H. Banskota, Y. Tezuka, P.H. Kim, T.K. Qui, H. Saiki, Y. Miwa, T. Taga, and S. Kadota Bioorg. Med. Chem. Lett. 8 1998 3519
10. E.L. Saxe, M. Shimizu, D. Xiao, P. Nuntanakorn, J.T.E. Lim, M. Suzui, C. Seter, T. Pertel, E.J. Kennelly, F. Kronenberg, and I.B. Weinstein Breast Cancer Res. Tr. 83 2004 221
11. C.L. Céspedes, M. Martínez-Vázquez, J.S. Calderón, J.R. Salazar, and A. Aranda Z. Naturforsch. 56c 2001 95
12. R.A. Komoroski, E.C. Gregg, J.P. Shockcor, and J.M. Geckle Magn. Reson. Chem. 24 1986 534
13. R. Martínez, M. Martínez-Vázquez, and O. Zamorano-Macías Org. Mass Spectrom. 25 1990 237
14. M. Martínez-Vazquez, R. Martínez, and P.G. Espinosa Fitoterapia LXV 4 1994 371
15. H. Parra-Delgado, T. Ramírez-Apan, and M. Martínez- Vázquez Rev. Latinoamer. Quím. Suppl. 29 2001 76
16. The resin, a by-product of the industrial process to obtain natural rubber from P. argentatum was donated by CONAZA Company (Coahuila, Mexico). The resin (157.39 g) was dissolved in a small volume of hexane and percolated over tonsil. The first fractions collected were reunited and chromatographed on Silica gel. This procedure resulted in the isolation of argentatin A (4.2 g), which was purified by conventional procedures.
17. 1, a = 27.458 (2), b = 7.9900 (10), c = 13.0030 (10). Crystallographic data for the structure have been deposited with the Cambridge Crystallographic Data Center, CCDC-254670. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: +44 (1223)336 033; e-mail for inquiry: fileserv@ccdc.cam.ac.uk).
18. M. Martínez-Vázquez, R. Martínez, and R.A. Toscano J. Chem. Crystallogr. 25 1995 331
19. J. Jakupovic, V.P. Pathak, F. Bohlmann, and X.A. Dominguez Phytochemistry 26 1987 761
20. G.T. Maatooq, and J.H. Hoffmann Z. Naturforsch. 57c 2002 489
21. A. Monks, D. Scudiero, P. Skehan, R. Shoemaker, K. Paull, D. Vistica, C. Hose, J. Langley, P. Cronise, A. VaigroWolff, M. Gray-Goodrich, H. Campbell, J. Mayo, and M. Boyd J. Natl. Cancer Inst. 83 1991 757
22. Doxorubicin was used at five different concentrations (0.01-5 μM) as a positive control