Facile synthesis of oleanolic acid monoglycosides and diglycosides

Molecules

Volumn 13, Issue 7, 2008, Pages 1472-1486

  Sha, Yu ^a   Yan, Mao Cai ^a   Liu, Jiao ^a   Liu, Yang ^a   Cheng, Mao Sheng ^a  

^a SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

Glycoside; Glycosylation; Oleanolic acid; Synthesis; Triterpenoid

Indexed keywords

DRUG DERIVATIVE; GLYCOSIDE; OLEANOLIC ACID; SAPONIN;

ARTICLE; CHEMISTRY; GLYCOSYLATION; SYNTHESIS;

GLYCOSIDES; GLYCOSYLATION; OLEANOLIC ACID; SAPONINS;

EID: 48849090364     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules13071472     Document Type: Article

References (29)

1. Dzubak, P.; Hajduch, M.; Vydra, D.; Hustova, A.; Kvasnica, M.; Biedermann, D.; Markova, L.; Urban, M.; Sarek, J. Pharmacological activities of natural triterpenoids and their therapeutic implications. Nat. Prod. Rep. 2006, 23, 394-411.
2. Liu, J. Pharmacology of oleanolic acid and ursolic acid. J. Ethnopharmacol. 1995, 49, 57-68.
3. Hsu, H. Y.; Yang, J. J.; Lin, C. C. Effects of oleanolic acid and ursolic acid on inhibiting tumor growth and enhancing the recovery of hematopoietic system postirradiation in mice. Cancer Lett. 1997, 111, 7-13.
4. Barthomeuf, C.; Debiton, E.; Mshvidadze, V.; Kemertelidze, E.; Balansard, G. In vitro activity of hederacolchisid A1 compared with other saponins from Hedera colchica against proliferation of human carcinoma and melanoma cells. Planta Med. 2002, 68, 672-675.
5. Jung, H. J.; Lee, C. O.; Lee, K. T.; Choi, J.; Park, H. J. Structure-activity relationship of oleanane disaccharides isolated from Akebia quinata versus cytotoxicity against cancer cells and NO inhibition. Biol. Pharm. Bull. 2004, 27, 744-747.
6. Li, Y.; Matsuda, H.; Yoshikawa, M. Effects of oleanolic acid glycosides on gastrointestinal transit and ileus in mice. Bioorg. Med. Chem. 1999, 7, 1201-1205.
7. Hardegger, E.; Leemann, H. J.; Robinet, F. G. Steroid and triterpene glycosides. III. Glucosides of esters of oleanic acid and glycosidal binding in beet-sugar saponins. Helv. Chim. Acta. 1952, 35, 824-829.
8. Kochetkov, N. K.; Khorlin, A. Ya.; Snyatkova, V. I. Triterpenoid saponins 13. Halolysis of glycosides of the triterpene series and the synthesis of glucosides of oleanolic acid. Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya. 1964, 2028-36;
9. English Translation: Russian Chemical Bulletin 1964, 13, 1925-1931.
10. Kochetkov, N. K.; Khorlin, A. Ya.; Bochkov, A. F.; Kretsu, L. G. Synthesis of glycosides of oleanolic acid. Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya. 1966, 2028-2029;
11. English Translation: Russian Chemical Bulletin 1966, 15, 1963-1965.
12. Juodvirsis, A.; Troshchenko, A. T. Synthesis of triterpene glycosides I. Synthesis of acyl glycosides of oleanolic and ursotic acids. Khimiya Prirodnykh Soedinenii. 1966, 2, 405-410;
13. English Translation: Chemistry of Natural Compounds 1966, 2, 331-334.
14. Janiszowska, W.; Wilkomirski, B.; Kasprzyk, Z. Synthesis of oleanolic acid 3-O-monoglucoside. Polish Journal of Chemistry. 1980, 54, 2147-2152.
15. Seebacher, W.; Haslinger, E.; Rauchensteiner, K.; Jurenitsch, J.; Presser, A.; Weis, R. Synthesis and Haemolytic Activity of Randianin Isomers. Monatshefte fuer Chemie. 1999, 130, 887-897.
16. Seebacher, W.; Weis, R.; Jurenitsch, J.; Rauchensteiner, K.; Haslinger, E. Synthesis and hemolytic properties of arvensoside B isomers. Monatshefte fuer Chemie. 2000, 131, 985-996.
17. Ohtani, K.; Mizutani, K.; Kasai, R.; Tanaka, O. Selective cleavage of ester type glycosidelinkages and its application to structure determination of natural oligoglycosides. Tetrahedron Lett. 1984, 25, 4537-4540.
18. Deng, S. J.; Yu, B.; Xie, J. M.; Hui, Y. Z. A highly efficient glycosylation of sapogenins. J. Org. Chem. 1999, 64, 7265-7266.
19. Schmidt, R. R.; Michel, J. Facile synthesis of α- and β-O-glycosyl imidates; Preparation of glycosides and disaccharides. Angew. Chem. Int. Ed. Engl. 1980, 19, 731-732.
20. Zang, J.; Li, Y. X.; Li, C. X.; Song, N.; Yue, C. L. Synthesis of Four Oleanolic Saponins. Periodical of Ocean University of China. 2005, 35, 635-640.
21. Sun, J.; Han, X.; Yu, B. Synthesis of a typical N-acetylglucosamine containing saponin, oleanolic acid 3-O-α- L-arabinopyranosyl-(1→2)-α-L-arabinopyranosyl- (1→6)-2-acetamido-2-deoxy-β-D-glucopyranoside. Carbohydr. Res. 2003, 338, 827-833.
22. Cheng, M. S.; Yan, M. C.; Liu, Y.; Zheng, L. G.; Liu, J. Synthesis of beta-hederin and Hederacolchiside A. 1: triterpenoid saponins bearing a unique cytotoxicity-inducing disaccharide moiety. Carbohydr. Res. 2006, 341, 60-67.
23. Li, C. X.; Zang, J.; Wang, P.; Zhang, X. L.; Guan, H. S.; Li, Y. X. Synthesis of two natural oleanolic acid saponins. Chinese J. Chem. 2006, 24, 509-517.
24. Yu, B.; Xie, J.; Deng, S.; Hui, Y. First Synthesis of a bidesmosidic triterpene saponin by a highly efficient procedure. J. Am. Chem. Soc. 1999, 121, 12196-12197.
25. Peng, W.; Sun, J.; Lin, F.; Han, X.; Yu, B. Facile Synthesis of Ginsenoside Ro. Synlett 2004, 259-262.
26. Yan, M. C.; Liu, Y.; Chen, H.; Ke, Y.; Xu, Q. C.; Cheng, M. S. Synthesis and antitumor activity of two natural N-acetylglucosamine-bearing triterpenoid saponins: Lotoidoside D and E. Bioorg. Med. Chem. Lett. 2006, 16, 4200-4204.
27. Winterstein, A.; Stein, G. Double bond between C-12 and C-13 of oleanolic acid is inert to catalytic hydrogenation. Z. Physiol. Chem. 1931, 202, 222-231.
28. Bliard, C.; Massiot, G.; Nazabadioko, S. Glycosylation of acids under phase transfer conditions. Partial synthesis of saponins. Tetrahedron Lett. 1994, 35, 6107-6108.
29. Schmidt, R. R.; Kinzy, W. Anomeric-oxygen activation for glycoside synthesis: The trichloroacetimidate method. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21-125.