Synthesis, cytotoxicity, and haemolytic activity of chacotrioside lupane-type neosaponins and their germanicane-type rearrangement products

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 8, 2009, Pages 2310-2314

  Gauthier, Charles ^a   Legault, Jean ^a   Piochon, Marianne ^a   Lavoie, Serge ^a   Tremblay, Samuel ^a   Pichette, André ^a  

^a UNIVERSITÉ DU QUÉBEC À CHICOUTIMI   (Canada)

Author keywords

Chacotrioside; Cytotoxicity; Germanicane; Haemolytic activity; Lupane; Saponin

Indexed keywords

28 OXOALLOBETULIN 3BETA O CHACOTRIOSIDE; ALLOBETULIN; BETULIC ACID; BETULIN; BETULINIC ACID O GLYCOSIDE; CHACOTRIOSIDE DERIVATIVE; GERMANICANE; LUPANE; LUPEOL; SAPONIN DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST ADENOCARCINOMA; DRUG CYTOTOXICITY; DRUG SYNTHESIS; HEMOLYSIS; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; PROSTATE ADENOCARCINOMA; PROTEIN GLYCOSYLATION;

ANIMALS; CELL LINE, TUMOR; CYTOTOXINS; ERYTHROCYTES; HEMOLYTIC AGENTS; HUMANS; SAPONINS; SHEEP; TRITERPENES; TROPANES;

EID: 63549116461     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.02.076     Document Type: Article

References (36)

1. Cichewicz R.H., and Kouzi S.A. Med. Res. Rev. 24 (2004) 90
2. Patočka J. J. Appl. Biomed. 1 (2003) 7
3. Yogeeswari P., and Sriram D. Curr. Med. Chem. 12 (2005) 657
4. Dzubak P., Hajduch M., Vydra D., Hustova A., Kvasnica M., Biedermann D., Markova L., Urban M., and Sarek J. Nat. Prod. Rep. 23 (2006) 394
5. Sami A., Taru M., Salme K., and Jari Y.-K. Eur. J. Pharm. Sci. 29 (2006) 1
6. Chaturvedi P.K., Bhui K., and Shukla Y. Cancer Lett. 263 (2008) 1
7. Eiznhamer D.A., and Xu Z.-Q. IDrugs 7 (2004) 359
8. Mukherjee R., Kumar V., Srivastava S.K., Agarwal S.K., and Burman A.C. Curr. Med. Chem. Anti-Cancer Agents 6 (2006) 271
9. Baglin I., Mitaine-Offer A.-C., Nour M., Tan K., Cavé C., and Lacaille-Dubois M.-A. Mini-Rev. Med. Chem. 3 (2003) 159
10. Krasutsky P.A. Nat. Prod. Rep. 23 (2006) 919
11. Tolstikova T.G., Sorokina I.V., Tolstikov G.A., Tolstikov A.G., and Flekhter O.B. Russ. J. Bioorg. Chem. 32 (2006) 261
12. Gauthier C., Legault J., Lebrun M., Dufour P., and Pichette A. Bioorg. Med. Chem. 14 (2006) 6713
13. Thibeault D., Gauthier C., Legault J., Bouchard J., Dufour P., and Pichette A. Bioorg. Med. Chem. 15 (2007) 6144
14. Gauthier C., Legault J., Lavoie S., Rondeau S., Tremblay S., and Pichette A. Tetrahedron 64 (2008) 7386
15. Gauthier C., Legault J., Lavoie S., Rondeau S., Tremblay S., and Pichette A. J. Nat. Prod. 72 (2009) 72
16. Francis G., Kerem Z., Makkar H.P.S., and Becker K. Br. J. Nutr. 88 (2002) 587
17. Sparg S.G., Light M.E., and van Staden J. J. Ethnopharmacol. 94 (2004) 219
18. Gauthier C., Legault J., Girard-Lalancette K., Mshvildadze V., and Pichette A. Bioorg. Med. Chem. 17 (2009) 2002
19. Liu M.-J., Wang Z., Ju Y., Zhou J.-B., Wang Y., and Wong R.N.-S. Biol. Pharm. Bull. 27 (2004) 1059
20. Wang Y., Cheung Y.H., Yang Z., Chiu J.-F., Che C.-M., and He Q.-Y. Proteomics 6 (2006) 2422
21. Hu K., Dong A., Yao X., Kobayashi H., and Iwasaki S. Planta Med. 62 (1996) 573
22. Nakamura T., Komori C., Lee Y.-Y., Hashimoto F., Yahara S., Nohara T., and Ejima A. Biol. Pharm. Bull. 19 (1996) 564
23. Ikeda T., Tsumagari H., Honbu T., and Nohara T. Biol. Pharm. Bull. 26 (2003) 1198
24. Cham B.E., and Daunter B. Cancer Lett. 55 (1990) 221
25. Chang L.-C., Tsai T.-R., Wang J.-J., Lin C.-N., and Kuo K.-W. Biochem. Biophys. Res. Commun. 242 (1998) 21
26. Yu B., Zhang Y., and Tang P. Eur. J. Org. Chem. 31 (2007) 5145
27. Jiang L., and Chang T.-H. J. Org. Chem. 63 (1998) 6035
28. Schmidt R.R., and Toepfer A. Tetrahedron Lett. 32 (1991) 3353
29. Zhang Y., Li Y., Guo T., Guan H., Shi J., Yu Q., and Yu B. Carbohydr. Res. 340 (2005) 1453
30. Li T.-S., Wang J.-X., and Zheng X.-J. J. Chem. Soc., Perkin Trans. 1 (1998) 3957
31. Lavoie S., Pichette A., Garneau F.-X.G., Girard M., and Gaudet D. Synth. Commun. 31 (2001) 1565
32. García-Granados A., López P.E., Melguizo E., Parra A., and Simeó Y. Tetrahedron 60 (2004) 1491
33. 3OD, 400 MHz): δ 5.36 (1H, d, J = 1.1 Hz, H-1′′), 4.84 (1H, d, J = 1.2 Hz, H-1′′′), 4.70 (1H, m, H-29), 4.59 (1H, m, H-29), 4.42 (1H, d, J = 7.7 Hz, H-1′), 3.97 (1H, m, H-5′′), 3.96 (1H, dd, J = 3.2, 1.4 Hz, H-2′′), 3.90 (1H, dd, J = 9.5, 6.2 Hz, H-5′′′), 3.83 (1H, dd, J = 3.0, 1.8 Hz, H-2′′′), 3.79 (1H, dd, J = 12.0, 1.4 Hz, H-6′)
34. O'Brien J., Wilson I., Orton T., and Pognan F. Eur. J. Biochem. 267 (2000) 5421
35. Kessler J.H., Mullauer F.B., de Roo G.M., and Medema J.P. Cancer Lett. 25 (2007) 132
36. Wang Y., Zhang Y., Zhu Z., Zhu S., Li Y., Li M., and Yu B. Bioorg. Med. Chem. 15 (2007) 2528