Efficient synthesis of trisaccharide saponins and their tumor cell killing effects through oncotic necrosis

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 2, 2011, Pages 622-627

  Gao, Jian ^a   Li, Xia ^b   Gu, Guofeng ^a   Sun, Bin ^a   Cui, Min ^b   Ji, Mei ^a   Lou, Hong Xiang ^a  

^a SHANDONG UNIVERSITY   (China)

^b SHANDONG UNIVERSITY   (China)

Author keywords

Cytotoxicity; Indioside E; Oncosis; Saponin; Trisaccharide analogues

Indexed keywords

AGLYCONE; ANTINEOPLASTIC AGENT; INDIOSIDE E; LACTATE DEHYDROGENASE; NEOSAPONIN; PLANT EXTRACT; SOLAMARGINE; SOLASONINE; TRISACCHARIDE SAPONIN DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL DEATH; CELL MEMBRANE; CELL STRUCTURE; CYTOSKELETON; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME RELEASE; GLYCOSYLATION; HUMAN; HUMAN CELL; IMMUNOCYTOCHEMISTRY; MICROSCOPY; NECROSIS; SOLANUM; SOLANUM INDICUM; STAINING; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL SURVIVAL; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MODELS, MOLECULAR; NEOPLASMS; PLANTS, MEDICINAL; SAPONINS; SOLANUM; TRISACCHARIDES;

HUMAN ECHOVIRUS 1; SOLANUM LASIOCARPUM;

EID: 78651239843     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.12.046     Document Type: Article

References (22)

1. S.G. Sparg, M.E. Light, and J. van Staden J. Ethnopharmacol. 94 2004 219
2. W.J. Kwak, C.K. Han, H.W. Chang, H.P. Kim, S.S. Kang, and K.H. Son Chem. Pharm. Bull. 51 2003 333
3. M. Iorizzi, V. Lanzotti, G. Ranalli, S. De Marino, and F. Zollo J. Agric. Food Chem. 50 2002 4310
4. A.J. De Lucca, J.M. Bland, C.B. Vigo, M. Cushion, C.P. Selitrennikoff, J. Peter, and T. Walsh J. Med. Mycol. 40 2002 131
5. Q.L. Tran, Y. Tezuka, A.H. Banskota, Q.K. Tran, I. Saiki, and S. Kadota J. Nat. Prod. 64 2001 1127
6. Y. Wang, Y. Zhang, Z. Zhu, S. Zhu, Y. Li, M. Li, and B. Yu Bioorg. Med. Chem. 15 2007 2528
7. S. Man, W. Gao, Y. Zhang, L. Huang, and C. Liu Fitoterapia 81 2010 703
8. C.H. Liang, L.F. Liu, L.Y. Shiu, Y.S. Huang, L.C. Chang, and K.W. Kuo Biochem. Biophys. Res. Commun. 322 2004 751
9. L.C. Chang, T.R. Tsai, J.J. Wang, C.N. Lin, and K.W. Kuo Biochem. Biophys. Res. Commun. 242 1998 21
10. W. Peng, P. Tang, X. Hu, J.O. Liu, and B. Yu Bioorg. Med. Chem. Lett. 17 2007 5506
11. D. Zheng, L. Zhou, Y. Guan, X. Chen, W. Zhou, X. Chen, and P. Lei Bioorg. Med. Chem. Lett. 20 2010 5439
12. S. Yahara, T. Nakamura, Y. Someya, T. Matsumoto, T. Yamashita, and T. Nohara Phytochemistry 43 1996 1319
13. G. Gu, Y. Du, and R.J. Linhardt J. Org. Chem. 69 2004 5497
14. F. Roussel, L. Knerr, M. Grathwohl, and R.R. Schmidt Org. Lett. 2 2000 3043
15. S. Dasgupta, B. Roy, and B. Mukhopadhyay Carbohydr. Res. 341 2006 2708
16. Y. Du, G. Wei, S. Cheng, Y. Hua, and R.J. Linhardt Tetrahedron Lett. 47 2006 307
17. 2) with a 5:1 solution of petroleum ether-EtOAc to afford the protected glycosides 15-20 in the form of β isomer with the yield ranging from 81% to 87%.
18. +): 879.4713; found 879.4719.
19. K.R. Wang, J.X. Yan, B.Z. Zhang, J.J. Song, P.F. Jia, and R. Wang Cancer Lett. 278 2009 65
20. A.L. Neisch, O. Speck, B. Stronach, and R.G. Fehon J. Cell Biol. 189 2010 311
21. W. Malorni, F. Iosi, F. Mirabelli, and G. Bellomo Chem. Biol. Interact. 80 1991 217
22. Superimposition was calculated by Molecular Modeling System SYBYL-X-1.1; Tripos Associates, Inc.