Concise synthesis of two natural triterpenoid saponins, oleanolic acid derivatives isolated from the roots of Pulsatilla chinensis

Carbohydrate Research

Volumn 344, Issue 11, 2009, Pages 1276-1281

  Liu, Qingchao ^a   Wang, Peng ^a   Zhang, Lei ^a   Guo, Tiantian ^a   Lv, Guokai ^a   Li, Yingxia ^a  

^a BEIJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

Author keywords

HL 60 cells; Mbp thioglycoside; One pot reaction; Trichloroacetimidates; Triterpenoid saponins

Indexed keywords

HL-60 CELLS; MBP THIOGLYCOSIDE; ONE-POT REACTION; TRICHLOROACETIMIDATES; TRITERPENOID SAPONINS;

CALCIUM ION SENSORS;

2 METHYL 5 TERT BUTYLPHENYL 1 THIO ALPHA LEVO RHAMNOPYRANOSIDE; 2 METHYL 5 TERT BUTYLPHENYL 2,3,4 TRI O ACETYL 1 THIO ALPHA LEVO RHAMNOPYRANOSIDE; 2 METHYL 5 TERT BUTYLPHENYL 2,4 DI O ACETYL 1 THIO ALPHA LEVO RHAMNOPYRANOSIDE; 3 O [BETA DEXTRO GLUCOPYRANOSYL (1-4) BETA DEXTRO GLUCOPYRANOSYL (1-3) ALPHA LEVO RHAMNOPYRANOSYL (1-2) (BETA DEXTRO GLUCOPYRANOSYL (1-4) ALPHA LEVO ARABINOPYRANOSYL]OLEANOLIC ACID; 3 O [BETA DEXTRO GLUCOPYRANOSYL (1-4) BETA DEXTRO GLUCOPYRANOSYL (1-3) ALPHA LEVO RHAMNOPYRANOSYL (1-2) ALPHA LEVO ARABINOPYRANOSYL]OLEANOLIC ACID; BENZYL 2 O [2,3,4,6 TETRA O BENZOYL BETA DEXTRO GLUCOPYRANOSYL (1-4) 2,3,6 TRI O BENZOYL BETA DEXTRO GLUCOPYRANOSYL (1-3) 2,4 DI O ACETYL ALPHA LEVO RHAMNOPYRANOSYL (1-2) 3,4 O ISOPROPYLIDENE ALPHA LEVO ARABINOPYRANOSYL]OLEANOLATE; BENZYL 3 O [2,3,4,6 TETRA O BENZOYL BETA DEXTRO GLUCOPYRANOSYL (1-4) 2,3,6 TRI O BENZOYL BETA DEXTRO GLUCOPYRANOSYL (1-3) 2,4 DI O ACETYL ALPHA LEVO RHAMNOPYRANOSYL (1-2) ALPHA LEVO ARABINOPYRANOSYL]OLEANOLATE; OLEANOLIC ACID DERIVATIVE; SAPONIN DERIVATIVE; THIOGLYCOSIDE; TRICHLOROACETIMIDIC ACID; TRITERPENOID; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL STRAIN HL 60; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; NONHUMAN; ONE POT SYNTHESIS; PLANT ROOT; PRIORITY JOURNAL; PULSATILLA;

BIOLOGICAL PRODUCTS; OLEANOLIC ACID; PLANT ROOTS; PULSATILLA; SAPONINS; THIOGLYCOSIDES; TRICHLOROACETIC ACID;

PULSATILLA CHINENSIS;

EID: 67649417998     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2009.05.011     Document Type: Article

References (51)

1. Hostettmann K., and Marston A. Saponins (1995), Cambridge University Press, New York
2. Waller G.R., and Yamasachi K. Saponins Used in Traditional and Modern Medicine (1996), Plenum Press, New York
3. Mahato S.B., Ganguly A.N., and Sahu N.P. Phytochemistry 21 (1982) 959-978
4. Bersuker I.B., Dimaglo A.S., Choban I.N., Lazurewskii G.V., and Kintya P.K. Khim.-Farm. Zh. 17 (1983) 1467-1471
5. Tekeda T., Nakamura Y., Takashima S., Yano O., and Ogihara Y. Chem. Pharm. Bull. 41 (1993) 2132-2137
6. Tani C., Ogihara Y., Mutuga M., Nakamura T., and Tekeda T. Chem. Pharm. Bull. 44 (1996) 816-822
7. Abdel K.M., Hoch J., and Berger J.M. J. Nat. Prod. 64 (2001) 536-539
8. Seo Y., Hoch J., and Abdel K.M. J. Nat. Prod. 65 (2002) 170-174
9. Krief S., Thoison O., Sevenet T., Wrangham R.W., and Lavaud C. J. Nat. Prod. 68 (2005) 897-903
10. Ohtsuki T., Miyagawa T., Koyano T., Kowithayakorn T., Kawahara N., Goda Y., and Ishibashi M. J. Nat. Prod. 71 (2008) 918-921
11. Ma S.G., Hu Y.C., Yu S.S., Zhang Y., Chen X.G., Liu J., and Liu Y.X. J. Nat. Prod. 71 (2008) 41-46
12. Cioffi G., Piaz F.D., Vassallo A., Venturella F., Caprariis P.D., Simone F.D., and Tommasi N.D. J. Nat. Prod. 71 (2008) 1000-1004
13. Ukiya M., Akihisa T., Yasukawa K., Tokuda H., Suzuki T., and Kimura Y. J. Nat. Prod. 69 (2006) 1692-1696
14. Havala C., and hylands P.I. Planta Med. 33 (1978) 180
15. Chande R.S., and Rastogi R.P. Phytochemistry 19 (1980) 1889-1908
16. Magid A.A., Voutquenne L., Harakat D., Pouny I., and Caron C. J. Nat. Prod. 69 (2006) 919-926
17. Konoshima T., Yaduda I., Kashiwada Y., Cosentino L.M., and Lee K.H. J. Nat. Prod. 58 (1995) 1372-1377
18. Yu D.L., Sakurai Y., Chen C., Chang F.R., Huang L., Kashiwada Y., and Lee K.H. J. Med. Chem. 49 (2006) 5462-5469
19. Dat N.T., Bae K., Wamiru A., Mcmahon G.B., Grice S., Bona M., Beutler J.A., and Kim Y.H. J. Nat. Prod. 70 (2007) 839-841
20. Peng W.J., Sun J.S., Lin F., Han X.W., and Yu B. Synlett (2004) 0259-0262
21. Peng W.J., Han X.W., and Yu B. Synthesis 10 (2004) 1641-1647
22. Zhang Y.C., Li Y.X., Guo T.T., Guan H.S., Shi J.W., Yu Q., and Yu B. Carbohydr. Res. 340 (2005) 1453-1459
23. Wang P., Li C.X., Zang J., Song N., Zhang X.L., and Li Y.X. Carbohydr. Res. 340 (2005) 2086-2096
24. Wang P.F., Kim Y.J., Mauricio N.V., Rohde B.D., and Gin D.Y. J. Am. Chem. Soc. 127 (2005) 3256-3257
25. Kim Y.J., Wang P.F., Mauricio N.V., Rohde B.D., Derryberry J., and Gin D.Y. J. Am. Chem. Soc. 128 (2006) 11906-11915
26. Cheng S.H., Du Y.G., Bing F.H., and Zhang G.B. Carbohydr. Res. 343 (2008) 462-469
27. Zhu S.L., Li Y.X., and Yu B. J. Org. Chem. 73 (2008) 4978-4985
28. Zhu C.S., Tang P.P., and Yu B. J. Am. Chem. Soc. 130 (2008) 5872-5873
29. Cheng M.S., Yan M.C., Liu Y., Zheng L.G., and Liu J. Carbohydr. Res. 341 (2006) 60-67
30. Yan M.C., Liu Y., Lu W.X., Wang H., Sha Y., and Cheng M.S. Carbohydr. Res. 343 (2008) 780-784
31. Mimaki Y., Kuroda M., Asano T., and Sashida Y. J. Nat. Prod. 62 (1999) 1279-1283
32. Ravhavan S., and Kahne D. J. Am. Chem. Soc. 115 (1993) 1580-1581
33. Chenault H.K., and Castro A. Tetrahedron Lett. 35 (1994) 9145-9148
34. Ley S.V., and Priepke H.W.M. Angew. Chem., Int. Ed. Engl. 33 (1994) 2292-2294
35. Yamada H., Harada T., and Takahashi T. J. Am. Chem. Soc. 116 (1994) 7919-7920
36. Yamada H., Harada T., Miyazaki H., and Takahashi T. Tetrahedron Lett. 35 (1994) 3979-3982
37. Lu S.F., O'yang Q.Q., Guo Z.W., Yu B., and Hui Y.Z. Angew. Chem., Int. Ed. 36 (1997) 2344-2346
38. Yoshida M., Kiyoi T., Tsukida T., and Kondo H. J. Carbohydr. Chem. 17 (1998) 673-681
39. Yamada H., Tetsuya K., and Takahashi T. Tetrahedron Lett. 40 (1999) 4581-4584
40. Zhang Z., Ollmann I.R., Ye X.S., wischnat R., Baasov T., and Wong C.H. J. Am. Chem. Soc. 121 (1999) 734-753
41. Yu B., Yang Z.Y., and Cao H.Z. Curr. Org. Chem. 9 (2005) 179-194
42. Yu H., Yu B., Wu X.Y., Hui Y.Z., and Han X.W. J. Chem. Soc., Perkin Trans. 1 (2000) 1445-1453
43. Yu B., Yu H., Hui Y.Z., and Han X.W. Tetrahedron Lett. 40 (1999) 8591-8594
44. Yu B., Xie J.M., Deng S.J., and Hui Y.Z. J. Am. Chem. Soc. 121 (1999) 12196-12197
45. Collot M., Savreux J., and Mallet J.M. Tetrahedron 64 (2008) 1523-1535
46. Schmidt R.R., and Kinzy W. Adv. Carbohydr. Chem. Biochem. 50 (1994) 21-125
47. Qu F., Li Y.X., Zhang Y., and Zang J. Chin. J. Org. Chem. 23 (2003) 249-252 in Chinese
48. Chwalek M., Ple K., and Vountquenne N.L. Chem. Pharm. Bull. 52 (2004) 965-971
49. Yu C.S., Wang H.Y., Chiang L.W., and Pei K. Synthesis 9 (2007) 1412-1420
50. Mukhopadhyay B., and Field R.A. Carbohydr. Res. 338 (2003) 2149-2152
51. Zhang Z.H., Wang P., Ding N., Song G.P., and Li Y.X. Carbohydr. Res. 342 (2007) 1159-1168