Highly efficient synthesis of bioactive oleanane-type saponins

Carbohydrate Research

Volumn 452, Issue , 2017, Pages 43-46

  Sui, Jing Jing ^a   Zhou, Wen Hui ^b   Liu, De Yong ^a   Li, Ming Qing ^b   Sun, Jian Song ^a  

^a JIANGXI NORMAL UNIVERSITY   (China)

^b FUDAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOTOXICITY;

CYTOTOXIC ACTIVITIES; EFFICIENT SYNTHESIS; SCHMIDT GLYCOSYLATION; STRUCTURE ACTIVITY RELATIONSHIPS; SYNTHETIC EFFICIENCY; TETRASACCHARIDES; TRITERPENE SAPONINS; TRITERPENOID SAPONINS;

METABOLITES;

DISACCHARIDE; ELATOSIDE E; ELATOSIDE F; GUAIANIN N; MONOSACCHARIDE; OLEANOLIC ACID; SAPONIN DERIVATIVE; TRISACCHARIDE; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; OLEANANE; SAPONIN; TRITERPENE;

ARTICLE; BIOLOGICAL ACTIVITY; CANCER CELL LINE; CARBOHYDRATE SYNTHESIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; GLYCOSYLATION; HUMAN; HUMAN CELL; HYDROGENOLYSIS; IC50; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; SYNTHESIS; ANALOGS AND DERIVATIVES; CELL SURVIVAL; CHEMISTRY; DRUG EFFECT; HELA CELL LINE; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL SURVIVAL; HELA CELLS; HUMANS; OLEANOLIC ACID; SAPONINS; STRUCTURE-ACTIVITY RELATIONSHIP; TRITERPENES;

EID: 85032030599     PISSN: 00086215     EISSN: 1873426X     Source Type: Journal    
DOI: 10.1016/j.carres.2017.08.010     Document Type: Article

References (33)

1. For reviews, see.
2. Yu, B., Sun, J., Chem. Asian J. 4 (2009), 642–654.
3. Dinda, B., Debnath, S., Mohanta, B.C., Harigaya, Y., Chem. Biodivers. 7 (2010), 2327–2580.
4. Sheng, H., Sun, H., Nat. Prod. Rep. 28 (2011), 543–593.
5. Yang, Y., Laval, S., Yu, B., Adv. Carbohydr. Chem. Biochem. 71 (2014), 137–226.
6. Kim, N.-C., Desjardins, A.E., Wu, C.D., Kinghorn, A.D., J. Nat. Prod. 62 (1999), 1379–1384.
7. Du, Z., Zhu, N., Ze-Ren-Wang-Mu, N., Shen, Y., Planta Med. 69 (2003), 547–551.
8. Zheng, Q., Koike, K., Han, L.-K., Okuda, H., Nikaido, T., J. Nat. Prod. 67 (2004), 604–613.
9. Seo, Y., Hoch, J., Abdel-Kader, M., Malone, S., Derveld, I., Adams, H., Werkhoven, M.C.M., Wisse, J.H., Mamber, S.W., Dalton, J.M., Kingston, D.G.I., J. Nat. Prod. 65 (2002), 170–174.
10. Jayatilake, G.S., Freeberg, D.R., Liu, Z., Richheimer, S.L., Blake, M.E., Bailey, D.T., Haridas, V., Gutterman, J.U., J. Nat. Prod. 66 (2003), 779–783.
11. Cao, S., Norris, A., Miller, J.S., Ratovoson, F., Razafitsalama, J., Andriantsiferana, R., Rasamison, V.E., TenDyke, K., Suh, T., Kingston, D.G.I., J. Nat. Prod. 70 (2007), 361–366.
12. Yoshikawa, M., Murakami, T., Komatsu, H., Matsuda, H., Chem. Pharm. Bull. 46 (1998), 812–816.
13. Komatsu, H., Murakami, T., Matsuda, H., Yoshikawa, M., Heterocycles 48 (1998), 703–710.
14. For selected examples, see.
15. Wang, P., Kim, Y.-J., Navarro-Villalobos, M., Rohde, B.D., Gin, D.-Y., J. Am. Chem. Soc. 127 (2005), 3256–3257.
16. Kim, Y.-J., Wang, P., Navarro-Villalobos, M., Rohde, B.D., Berry, D., Gin, D.-Y., J. Am. Chem. Soc. 128 (2006), 11906–11915.
17. Zhu, C., Tang, P., Yu, B., J. Am. Chem. Soc. 130 (2008), 5872–5873.
18. Yoshikawa, M., Matsuda, H., Harada, E., Murakami, T., Wariishi, N., Yamahara, J., Murakami, N., Chem. Pharm. Bull. 42 (1994), 1354–1356.
19. An, R.-B., Na, M., Min, B.-S., Lee, H.-K., Bae, K., Nat. Prod. Sci. 14 (2008), 249–253.
20. Jung, H.-J., Lee, C.O., Lee, K.-T., Choi, J., Park, H.-J., Biol. Pharm. Bull. 27 (2004), 744–747.
21. Schmidt, R.R., Angew. Chem. Int. Ed. Engl. 25 (1986), 212–235.
22. Zhu, X., Schmidt, R.R., Angew. Chem. Int. Ed. 48 (2009), 1900–1943.
23. Chen, D., Zhang, P., Sun, Y., Wang, P., Zhang, C., Kong, L., Zhang, J., Sun, H., Wen, X., Org. Biomol. Chem. 14 (2016), 11154–11161.
24. Ple, K., Chwalek, M., Voutquenne-Nazabadioko, L., Eur. J. Org. Chem., 2004, 1588–1603.
25. Cheng, M.-S., Yan, M.-C., Liu, Y., Zheng, L.-G., Liu, J., Carbohydr. Res. 341 (2006), 60–67.
26. Mbadugha, B.N.A., Menger, F.M., Org. Lett. 5 (2003), 4041–4044.
27. Pilgrim, W., Murphy, P.V., J. Org. Chem. 75 (2010), 6747–6755.
28. Chen, L., Kong, F., Carbohydr. Res. 337 (2002), 2335–2341.
29. Sun, J., Han, X., Yu, B., Org. Lett. 7 (2005), 1935–1938.
30. Peng, W., Han, X., Yu, B., Synthesis, 2004, 1641–1647.
31. Gu, G., Du, Y., Linhardt, R.J., J. Org. Chem. 69 (2004), 5497–5500.
32. Sha, Y., Yan, M.-C., Liu, J., Liu, Y., Cheng, M.-S., Molecules 13 (2008), 1472–1486.
33. See supporting information.