Citation: Yu Tingting, Li Lei, Cui Huabo, Meng Yanqiu. Syntheses and Antitumor Activities of Ursolic Acid C-3, C-28 Derivatives[J]. Chemistry, ;2017, 80(11): 1055-1060. shu

Syntheses and Antitumor Activities of Ursolic Acid C-3, C-28 Derivatives

Department of Pharmaceutical Engineering, Shenyang University of Chemical Technology, Shenyang 110142

Corresponding author: Meng Yanqiu, myq6581@163.com
Received Date: 17 April 2017
Accepted Date: 30 August 2017

Figures(1)

Eleven unreported ursolic acid derivatives were designed and synthesized by the oxidation, acylation and esterification of natural product ursolic acid, meantime their structures were characterized by MS, ¹H NMR and elemental analysis. A549 and SGC-7901 cells were used to screen the anti-tumor activity in vitro through the MTT assay. The results indicated that the inhibitory rates of the target compounds on A549 and SGC-7901 cells were significantly higher than that of ursolic acid, especially the inhibitory activities of the compounds 4b and 5a are higher than that of 5-Fu and Gefitinib, which are worthy of further research endeavours.
- Ursolic acid,
- Synthesis,
- Anti-tumor activity
1. [1]
2. [2]
  W Liu. Molecules, 2012, 17(8):9104~9115.
3. [3]
  Y R Jin, J L Jin, C H Li et al. Pharm. Biol., 2012, 50(4):523~528.
4. [4]
  S Fontanay, M Grare, J Mayer et al. J. Ethnopharmacol., 2008, 120(2):272~276.
5. [5]
  O B Kazakova, E Y Giniyatullina G V Yamansarov et al. Bioorg. Med. Chem., 2010, 20(4):4088~4090.
6. [6]
7. [7]
  R R Ortizandrade, S Garcíajiménez, P Castilloespaña et al. J. Ethnopharmacol., 2007, 109(1):48~53.
8. [8]
9. [9]
10. [10]
  M H Shyu, T C Kao, G C Yen. J. Agric. Food. Chem., 2010, 58(10):6110~6118.
11. [11]
  Y X Zhang, C Z Kong, L H Wang et al. J. Cell. Biochem., 2010, 109(4):764~773.
12. [12]
  Y Zhang, C Kong, Y Zeng et al. Mol. Carcinogen., 2010, 49(4):374~385.
13. [13]
  P O Harmand, R Duval, B Liagre et al. Int. J. Oncol., 2003, 23(1):105~112.
14. [14]
  I Bonaccorsi, F Altieri, I Sciamanna et al. Cancer Lett., 2008, 263(1):130~139.
15. [15]
  S J Tsai, M C Yin. J. Food Sci., 2008, 73(7):H174~H178.
16. [16]
  M Kanjoormana, G Kuttan. Integr. Cancer Ther., 2010, 9(2):224~235.
17. [17]
  S L Yan, C Y Huang, S T Wu et al. Toxicol. In Vitro, 2010, 24(3):842~848.
18. [18]
  H J You, C Y Choi, J Y Kim et al. Febs Lett., 2001, 509(2):156~160.
19. [19]
  Y Q Meng, D Liu, L L Cai et al. Bioorg. Med. Chem., 2009, 17(2):848~854.
1. [1]
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2. [2]
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沈阳化工大学材料科学与工程学院沈阳 110142