Efficient synthesis of flaccidoside II, a bioactive component of Chinese folk medicine di Wu

Journal of Carbohydrate Chemistry

Volumn 28, Issue 9, 2009, Pages 506-519

  Liu, Qingchao ^a   Zhang, Lei ^a   Li, Xiangpeng ^a   Guo, Tiantian ^a   Wang, Peng ^a   Li, Yingxia ^b  

^a OCEAN UNIVERSITY OF CHINA   (China)

^b FUDAN UNIVERSITY   (China)

Author keywords

Bidesmosidic triterpene saponins; Di Wu; Flaccidoside II; Glycosyl trichloroacetimidates; One pot reaction

Indexed keywords

ANEMONE; ANEMONE FLACCIDA;

EID: 77649328407     PISSN: 07328303     EISSN: 15322327     Source Type: Journal    
DOI: 10.1080/07328300903260192     Document Type: Article

References (49)

1. Mahato, S.B.; Ganguly, A.N.; Sahu, N.P. Steroid saponins. Phytochemistry 1982, 21, 959-978.
2. Bersuker, I.B.; Dimaglo, A.S.; Choban, I.N.; Lazurewskii, G.V.; Kintya, P.K. Structure-antitumor activity relations in a series of steroidal glycosides. Khim.-Farm. Zh. 1983, 17, 1467-1471.
3. Hostettmann, K.;Marston, A. Saponins; Cambridge University Press: Cambridge, UK, 1995.
4. Takeda, T.; Nakamura, Y.; Takashima, S.; Yano, O.; Ogihara, Y. Studies on the constituents of Calliandra anomala (Kunth) Macbr. I. Structure elucidation of two acylated triterpenoidal saponins. Chem. Pharm. Bull. 1993, 41, 2132-2137.
5. Tani, C.; Ogihara, Y.; Mutuga, M.; Nakamura, T.; Tekeda, T. Studies on the constituents of Calliandra anomala (Kunth) Macbr. III. Structure elucidation of six acylated triterpenoidal saponins. Chem. Pharm. Bull. 1996, 44, 816-822.
6. Abdel, K.M.; Hoch, J.; Berger, J.M. Two Bioactive Saponins from Albizia subdimidiata from the Suriname Rainforest. J. Nat. Prod. 2001, 64, 536-539.
7. Seo, Y.; Hoch, J.; Abdel, K.M. Bioactive saponins from Acacia tenuifolia from the Suriname rainforest. J. Nat. Prod. 2002, 65, 170-174.
8. Krief, S.; Thoison, O.; Sevenet, T.; Wrangham, R.W.; Lavaud, C. Triterpenoid saponin anthranilates from Albizia grandibracteata leaves ingested by primates in Uganda. J. Nat. Prod. 2005, 68, 897-903.
9. Ohtsuki, T.; Miyagawa, T.; Koyano, T.; Kowithayakorn, T.; Kawahara, N.; Goda, Y.; Ishibashi, M. Acylated triterpenoid saponins from Schima noronhae and their cell growth inhibitory activity. J. Nat. Prod. 2008, 71, 918-921.
10. Ma, S.G.; Hu, Y.C.; Yu, S.S.; Zhang, Y.; Chen, X.G.; Liu, J.; Liu, Y.X. Cytotoxic triterpenoid saponins acylated with monoterpenic acid from Pithecellobium lucidum. J. Nat. Prod. 2008, 71, 41-46.
11. Cioffi, G.; Piaz, F.D.; Vassallo, A.; Venturella, F.; Caprariis, P.D.; Simone, F.D.; Tommasi, N.D. Antiproliferative oleanane saponins from Meryta denhamii. J. Nat. Prod. 2008, 71, 1000-1004.
12. 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.
13. Harvala, C.; Hylands, P. I. Saponins from Cyclamen hederifolium and C. graecum. Planta. Med. 1978, 33, 180.
14. Chandel, R.S.; Rastogi, R.P. Triterpenoid saponins and sapogenins: 1973-1978. Phytochemistry 1980, 19, 1889-1908.
15. 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)
16. Konoshima, T.; Yaduda, I.; Kashiwada, Y.; Cosentino, L.M.; Lee, K.H. Anti-AIDS agents, 21. Triterpenoid saponins as anti-HIV principles from fruits of Gleditsia japonica and Gymnocladus chinensis, and a structure-activity correlation. J. Nat. Prod. 1995, 58, 1372-1377.
17. 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.
18. Dat, N.T.; Bae, K.; Wamiru, A.; Mcmahon, G.B.; Grice, S.; Bona, M.; Beutler, J.A.; Kim, Y.H. A dimeric lactone from Ardisia japonica with inhibitory activity for HIV-1 and HIV-2 ribonuclease H. J. Nat. Prod. 2007, 70, 839-841.
19. Peng, W.J.; Sun, J.S.; Lin, F.; Han, X.W.; Yu, B. Facile synthesis of ginsenoside Ro. Synlett 2004, 2, 0259-0262.
20. Peng, W.J.; Han, X.W.; Yu, B. Synthesis of a typical glucuronide- containing saponin, 28-O- beta -D-glucopyranosyl oleanate 3-O-beta-D- galactopyranosyl-(1 beta 2)- [beta -D-glucopyranosyl-(1 beta 3)]- beta -D-glucuronopyranoside. Synthesis 2004, 10, 1641-1647.
21. 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.
22. Wang, P.; Li, C.X.; Zang, J.; Song, N.; Zhang, X.L.; Li, Y.X. Synthesis of two bidesmosidic ursolic acid saponins bearing a 2,3-branched trisaccharide residue. Carbohydr. Res. 2005, 340, 2086-2096.
23. Wang, P.F.; Kim, Y.J.;Mauricio, N.V.; Rohde, B.D.; Gin, D.Y. Synthesis of the potent immunostimulatory adjuvant QS-21A. J. Am. Chem. Soc. 2005, 127, 3256-3257.
24. Kim, Y.J.; Wang, P.F.; Mauricio, N.V.; Rohde, B.D.; Derryberry, J.; Gin, D.Y. Synthetic studies of complex immunostimulants from Quillaja saponaria: synthesis of the potent clinical immunoadjuvant QS-21Aapi. J. Am. Chem. Soc. 2006, 128, 11906-11915.
25. Zhu, S.L.; Li, Y.X.; Yu, B. Synthesis of Betavulgaroside III, a representative triterpene seco-glycoside. J. Org. Chem. 2008, 73, 4978-4985.
26. Zhu, C.S.; Tang, P.P.; Yu, B. Total synthesis of Lobatoside E, a potent antitumor cyclic triterpene saponin. J. Am. Chem. Soc. 2008, 130, 5872-5873.
27. 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.
28. Yan, M.C.; Liu, Y.; Lu, W.X.; Wang, H.; Sha, Y.; Cheng, M.S. Facile synthesis and cytotoxicity of triterpenoid saponins bearing a unique disaccharide moiety: hederacolchiside A1 and its analogs. Carbohydr. Res. 2008, 343, 780-784.
29. Bing, F.H.; Zhang, G.B. Five categories of new traditional Chinese medicine- Diwufengshian capsule. Hubei J. Tradit. Chin. Med. 2005, 27, 48-49 (in chinese).
30. Bing, F.H.; Yi, Y.D.; Zhang, G.B. Pharmacokinetics of effective component of Anemone flaccida Fr.Schmidt in mice following single intra-gastric dosing. J. Chin. Pharm. Univ. 2005, 36, 338-341.
31. Zhao, L.; Chen, W.M.; Fang, Q.C. Two new oleanane saponins from Anemone flaccida. Planta Med. 1991, 57, 572-574.
32. Cheng, S.H.; Du, Y.G.; Bing, F.H.; Zhang, G.B. Synthesis of flaccidoside II, a bidesmosidic triterpene saponin isolated from Chinese folk medicine DiWu. Carbohydr. Res. 2008, 343, 462-469.
33. 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.
34. Raghavan, S.; Kahne, D. A one step synthesis of the ciclamycin trisaccharide. J. Am. Chem. Soc. 1993, 115, 1580-1581.
35. Chenault, H.K.; Castro, A. Glycosyl transfer by isopropenyl glycosides: trisaccharide synthesis in one pot by selective coupling of isopropenyl and n-pentenyl glycopyranosides. Tetrahedron Lett, 1994, 35, 9145-9148.
36. Ley, S.V.; Priepke, H.W.M. Cyclohexane 1,2-diacetals in synthesis. 2. One-pot synthesis of a trisaccharide unit of the common polysaccharide antigen of group-B streptococci using cyclohexane 1,2-diacetal (CDA)-protected rhamnosides. Angew. Chem. Int. Ed. Engl. 1994, 33, 2292-2294.
37. Yamada, H.; Harada, T.; Takahashi, T. Synthesis of an elicitor-active hexaglucoside analog by a one-pot, two-step glycosidation procedure. J. Am. Chem. Soc. 1994, 116, 7919-7920.
38. Yamada, H.; Harada, T.; Miyazaki, H.; Takahashi, T. One-pot sequential glycosylation: a new method for the synthesis of oligosaccharides. Tetrahedron Lett. 1994, 35, 3979-3982.
39. Lu, S.F.; O'yang, Q.Q.; Guo, Z.W.; Yu, B.; Hui, Y.Z. The first total synthesis of tricolorin A. Angew. Chem. Int. Ed. Engl. 1997, 36, 2344-2346.
40. Yoshida, M.; Kiyoi, T.; Tsukida, T.; Kondo, H. One-pot synthesis of Lewis X oligosaccharide derivatives using "armed-disarmed" coupling method. J. Carbohydr. Chem. 1998, 17, 673-681. (Pubitemid 128429637)
41. Yamada, H.; Tetsuya, K.; Takahashi, T. One-pot sequential glycosylation: a new method for the synthesis of branched oligosaccharides. Tetrahedron Lett. 1999, 40, 4581-4584.
42. Zhang, Z.; Ollmann, I.R.; Ye, X.S.; wischnat, R.; Baasov, T.; Wong, C.H. Programmable one-pot oligosaccharide synthesis. J. Am. Chem. Soc. 1999, 121, 734-753.
43. Yu, B.; Yang, Z.Y.; Cao, H.Z. One-pot glycosylation (OPG) for the chemical synthesis of oligosaccharides. Cur. Org. Chem. 2005, 9, 179-194.
44. Yu, H.; Yu, B.; Wu, X.Y.; Hui, Y.Z.; Han, X.W. Synthesis of a group of diosgenyl saponins with combined use of glycosyl trichloroacetimidate and thioglycoside donors. J. Chem. Soc., Perkin trans. 1, 2000, 1445-1453.
45. Yu, B.; Yu, H.; Hui, Y.Z.; Han, X.W. Synthesis of a group of diosgenyl saponins by a one-pot sequential glycosylation. Tetrahedr. Lett. 1999, 40, 8591-8594.
46. 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.
47. Schmidt, R.R.; Kinzy, W. Anomeric-oxygen activation for glycoside synthesis: the trichloroacetimidate method. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21-123.
48. Zhang, M.M.; Du, Y.G.; Kong, F.Z. Practical synthesis of a tetrasaccharide derivative corresponding to ristomycin A and ristocetin A. Carbohydr. Res. 2001, 330, 319-324.
49. Deng, S.J.; Yu, B.; Xie, J.M.; Hui, Y.Z. Highly efficient glycosylation of sapogenins. J. Org. Chem. 1999, 64, 7265-7266.