Synthesis of the cytotoxic gitogenin 3β-O-[2-O-(α-L- rhamnopyranosyl)-β-D-galactopyranoside] and its congeners

Synthesis

Volumn , Issue 5, 2006, Pages 775-782

  Li, Yingxia ^a   Zhang, Yichun ^a   Guo, Tiantian ^a   Guan, Huashi ^a   Hao, Yan ^b   Yu, Biao ^b  

^a OCEAN UNIVERSITY OF CHINA   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Antitumor; Chacotrioside; Gitogenin 3 O 2 O ( L rhamnopyranosyl) D galactopyranoside ; Saponin; Synthesis

Indexed keywords

CELLS; SYNTHESIS (CHEMICAL); TOXIC MATERIALS; TUMORS;

ANTITUMOR; CHACOTRIOSIDE; GITOGENIN 3Β-O-[2-O-(Α-L-RHAMNOPYRANOSYL)-Β-D- GALACTOPYRANOSIDE];

ORGANIC COMPOUNDS;

ANTINEOPLASTIC AGENT; CYTOTOXIC AGENT; DIOSGENIN 3BETA O CHACOTRIOSIDE; GITOGENIN 3BETA O 2 O (ALPHA LEVO RHAMNOPYRANOSYL)BETA DEXTRO GALACTOPYRANOSIDE; GITOGENIN 3BETA O 2,4 DI O (ALPHA LEVO RHAMNOPYRANOSYL)BETA DEXTRO GALACTOPYRANOSIDE; GITOGENIN 3BETA O 2,4 DI O (ALPHA LEVO RHAMNOPYRANOSYL)BETA DEXTRO GLUCOPYRANOSIDE; SAPONIN DERIVATIVE; SPIROSTAN DERIVATIVE; TIGOGENIN 3BETA O 2,4 DI O (ALPHA LEVO RHAMNOPYRANOSYL)BETA DEXTRO GLUCOPYRANOSIDE; UNCLASSIFIED DRUG;

ARTICLE; CANCER INHIBITION; CONTROLLED STUDY; DRUG ISOLATION; DRUG MECHANISM; DRUG POTENCY; DRUG SYNTHESIS; HOSTA; HUMAN; HUMAN CELL; IC 50;

EID: 33644887133     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926316     Document Type: Article

References (26)

1. Mimaki, Y.; Kanmoto, T.; Kuroda, M.; Sashida, Y.; Satomi, Y.; Nishino, A. Phytochemistry 1996, 42, 1065.
2. Mimaki, Y.; Kuroda, M.; Kameyama, A.; Yokosuka, A.; Sashida, Y. Phytochemistry 1998, 48, 1361.
3. Yu, B.; Hui, Y. Chemical Synthesis of Bioactive Steroidal Saponins, In Glycochemistry: Principles, Synthesis, and Application; Wang, P. G.; Bertozzi, C. R., Eds.; Marcel Dekker Inc: New York, 2001, 163-174.
4. (a) Li, M.; Han, X.; Yu, B. Carbohydr. Res. 2003, 338, 117.
5. (b) Zhang, Y.; Li, Y.; Zhu, S.; Guan, H.; Lin, F.; Yu, B. Carbohydr. Res. 2004, 339, 1753.
6. (c) Zhang, Y.; Li, Y.; Guo, T.; Guan, H.; Shi, J.; Yu, Q.; Yu, B. Carbohydr. Res. 2005, 340, 1453.
7. (a) Nakamura, T.; Komori, C.; Lee, Y. Y.; Hashimoto, F.; Yahara, S.; Nohara, T.; Ejima, A. Biol. Pharm. Bull. 1996, 19, 564.
8. (b) Liu, M. J.; Wang, Z.; Ju, Y.; Zhou, J. B.; Wang, Y.; Wong, R. N. S. Biol. Pharm. Bull. 2004, 27, 1059.
9. Herran, J.; Rosenkranz, G.; Sondheimer, F. J. Am. Chem. Soc. 1954, 76, 5531.
10. Williams, J. R.; Gong, H.; Hoff, N.; Olubodun, O. I.; Carroll, P. J. Org. Lett. 2004, 6, 269.
11. (a) Schröder, M. Chem. Rev. 1980, 80, 187.
12. (b) Kametani, T.; Katoh, T.; Fujio, J.; Nogiwa, I.; Tsubuki, M.; Honda, T. J. Org. Chem. 1988, 53, 1982.
13. (c) Kametani, T.; Katoh, T.; Tsubuki, M.; Honda, T. J. Am. Chem. Soc. 1986, 108, 7055.
14. (d) Khripach, V. A.; Zhabinskii, V. N.; Antonchick, A. P.; Konstantinova, O. V.; Schneider, B. Steroids 2002, 67, 1101.
15. (a) David, S.; Hanessian, S. Tetrahedron 1985, 41, 643.
16. (b) Simas, A. B. C.; Pais, K. C.; Desilva, A. A. T. J. Org. Chem. 2003, 68, 5426.
17. (a) Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
18. (b) Boeckman, J. R. K.; Shao, P.; Mulins, J. J. Org. Synth. 1999, 77, 141.
19. Molander, G. A. Chem. Rev. 1992, 92, 29.
20. Deng, S.; Yu, B.; Xie, J.; Hui, Y. J. Org. Chem. 1999, 64, 7265.
21. (a) Lu, J.; Chan, T. H. J. Org. Chem. 1998, 63, 6035.
22. (b) Kim, S.; Chang, H.; Kim, W. J. J. Org. Chem. 1985, 50, 1751.
23. Du, Y.; Gu, G.; Wei, G.; Hua, Y.; Linhard, R. J. Org. Lett. 2003, 5, 3627.
24. Li, B.; Yu, B.; Hui, Y.; Li, M.; Han, X.; Fung, K. P. Carbohydr. Res. 2001, 331, 1.
25. Ikeda, T.; Tsumagari, H.; Okawa, M.; Nohara, T. Chem. Pharm. Bull. 2004, 52, 142.
26. Liu, X.; Cui, Y.; Yu, Q.; Yu, B. Phytochemistry 2005, 66, 1671.