Facile synthesis of several oleanane-type triterpenoid saponins

Journal of Carbohydrate Chemistry

Volumn 29, Issue 8-9, 2010, Pages 386-402

  Liu, Qingchao ^a   Fan, Zheng ^a   Li, Dong ^a   Li, Wenhong ^a   Guo, Tiantian ^b  

^a NORTHWEST UNIVERSITY   (China)

^b YAN'AN UNIVERSITY   (China)

Author keywords

Glucuronide residue; Oleanane type triterpenoid saponin; TEMPO mediated oxidation

Indexed keywords

PANAX GINSENG; PANAX JAPONICUS;

EID: 79955440243     PISSN: 07328303     EISSN: 15322327     Source Type: Journal    
DOI: 10.1080/07328303.2011.555898     Document Type: Article

References (18)

1. Magid, A. A.; Voutquenne, L.; Harakat, D., Pouny, I.; Caron, C. Triterpenoid saponins from the fruits of Caryocar villosum. J. Nat. Prod. 2006, 69, 919-926. (Pubitemid 44166266)
2. Ukiya, M.; Akihisa, T.; Yasukawa, K.; Tokuda, H.; Suzuki, T.; Kimura, Y. Antiinflammatory, anti-tumor-promoting, and cytotoxic activities of constituents of marigold (Calendula officinalis) flowers. J. Nat. Prod. 2006, 69, 1692-1696. (Pubitemid 46144960)
3. Cioffi, G.; Piaz, F. D.; Vassallo, A.; Venturella, F.; Caprariis, P. D.; Simone, F. D. Antiproliferative oleanane saponins from Meryta denhamii. J. Nat. Prod. 2008, 71, 1000-1004. (Pubitemid 352008895)
4. Yu, D. L.; Sakurai, Y.; Chen, C.; Chang, F. R.; Huang, L.; Kashiwada, Y.; Lee, K. H. Anti-AIDS agents 69. Moronic acid and other triterpene derivatives as novel potent anti-HIV agents. J. Med. Chem. 2006, 49, 5462-5469. (Pubitemid 44373178)
5. Hostettmann, K.; Marston, A. Saponins. Cambridge University Press: Cambridge, UK, 1995.
6. Yu, B.; Xie, J. M.; Deng, S. J.; Hui, Y. Z. First synthesis of a bidesmosidic triterpene saponin by a highly efficient procedure. J. Am. Chem. Soc. 1999, 121, 12196-12197. (Pubitemid 30027801)
7. Cheng, M. S.; Yan, M. C.; Liu, Y.; Zheng, L. G.; Liu, J. Synthesis of beta-hederin and Hederacolchiside A1: triterpenoid saponins bearing a unique cytotoxicity-inducing disaccharide moiety. Carbohydr. Res. 2006, 341, 60-67. (Pubitemid 41796977)
8. Zhu, S. L.; Li, Y. X.; Yu, B. Synthesis of Betavulgaroside III, a representative triterpene seco-glycoside. J. Org. Chem. 2008, 73, 4978-4985. (Pubitemid 351956561)
9. Huang, X.; Cheng, S. H.; Du, Y. G.; Bing, F. H. Synthesis of oleanolic acid saponins mimicking components of Chinese folk medicine Di Wu. Carbohydr. Res. 2009, 344, 1153-1158.
10. Guo, T. T.; Liu, Q. C.; Wang, P.; Zhang, L.; Zhang, W.; Li, Y. X. Facile synthesis of three bidesmosidic oleanolic acid saponins with strong inhibitory activity on pancreatic lipase. Carbohydr. Res. 2009, 344, 1167-1174.
11. Liu, Q. C.; Wang, P.; Zhang, L.; Guo, T. T.; Lv, G. K.; Li, Y. X. Concise synthesis of two natural triterpenoid saponins, oleanolic acid derivatives isolated from the roots of Pulsatilla chinensis. Carbohydr. Res. 2009, 344, 1276-1281.
12. Zhao, H.; Shi, L.; Cao, J. Q.; Li, W.; Wen, X.; Zhao, Y. Q. A new triterpene saponin from Panax japonicus C. A. Meyer var major (Burk.) C. Y. Wu et K. M. Feng. Chin. Chem. Lett. 2010, 21, 1216-1218.
13. Schmidt, R. R.; Kinzy, W. Anomeric-oxygen activation for glycoside synthesis: the trichloroacetimidate method. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21-123.
14. Kaname, K.; Yuta, I.; Kohsaka, O.; Kazuhiko, H.; Hiroaki, T.; Rikizo, A.; Kenichi, H. Synthesis of oligosaccharide with controlled sequence. Carbohydr. Lett. 2001, 4, 131-136.
15. Cheng, M. S.; Yan, M. C.; Liu, Y.; Zheng, L. G.; Liu, J. Synthesis of beta-hederin and Hederacolchiside A1: triterpenoid saponins bearing a unique cytotoxicity-inducing disaccharide moiety. Carbohydr. Res. 2006, 341, 60-67. (Pubitemid 41796977)
16. Rajput, V. K.; Mukhopadhyay, B. Concise synthesis of a pentasaccharide related to the anti-leishmanial triterpenoid saponin isolated from Maesa balansae. J. Org. Chem. 2008, 73, 6924-6927.
17. 2 under aqueous conditions. Carbohydr. Res. 2004, 339, 1219-1223. (Pubitemid 38519941)
18. Iranpoor, N.; Firouzabadi, H.; Aghapour, G.; Vaez zadeh, A. Triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone as a new, selective and neutral system for the facile conversion of alcohols, thiols and selenols to alkyl halides in the presence of halide ions. Tetrahedron 2002, 58, 8689-8693. (Pubitemid 35284562)