Synthesis and antitumor activity evaluation of ursolic acid derivatives

Abstract Eighteen uronic acid derivatives were designed and synthesized, and the cytotoxicities in vitro of two cancer cell lines (BEL7402 and SGC7901) were evaluated by MTT assay. The results showed that the inhibitory rate of the compounds on both cell lines was significantly higher than the parent compound. The IC50 of compounds II4, II6, III4, and III6 are comparable or stronger than the positive control drug, the interactions between compounds II4, II6, III4, III6, and NF-κB were also studied by docking simulations. Graphical Abstract

[1]  Z. Liao,et al.  Discovery of antitumor ursolic acid long-chain diamine derivatives as potent inhibitors of NF-κB. , 2018, Bioorganic chemistry.

[2]  R. Azimi,et al.  Efficient synthesis of 9,10-dihydropyrano[2,3-h]chromene-2,8-dione derivatives in ionic liquid and the study of their antioxidant activity , 2017, Natural product research.

[3]  Qiuwan Zhang,et al.  Ursolic acid inhibits the proliferation of human ovarian cancer stem-like cells through epithelial-mesenchymal transition. , 2015, Oncology reports.

[4]  H. Stuppner,et al.  Ursolic acid from Trailliaedoxa gracilis induces apoptosis in medullary thyroid carcinoma cells , 2015, Molecular medicine reports.

[5]  A. Moon,et al.  Ursolic acid inhibits the invasive phenotype of SNU-484 human gastric cancer cells , 2014, Oncology letters.

[6]  Jie Song,et al.  Ursolic Acid Inhibits Cigarette Smoke Extract-Induced Human Bronchial Epithelial Cell Injury and Prevents Development of Lung Cancer , 2012, Molecules.

[7]  Yong-ri Jin,et al.  Ursolic acid enhances mouse liver regeneration after partial hepatectomy , 2012, Pharmaceutical biology.

[8]  O. Kazakova,et al.  Betulin and ursolic acid synthetic derivatives as inhibitors of Papilloma virus. , 2010, Bioorganic & medicinal chemistry letters.

[9]  G. Kuttan,et al.  Antiangiogenic Activity of Ursolic Acid , 2010, Integrative cancer therapies.

[10]  Chun-Yin Huang,et al.  Oleanolic acid and ursolic acid induce apoptosis in four human liver cancer cell lines. , 2010, Toxicology in vitro : an international journal published in association with BIBRA.

[11]  R. Villalobos-Molina,et al.  alpha-Glucosidase inhibitory activity of the methanolic extract from Tournefortia hartwegiana: an anti-hyperglycemic agent. , 2007, Journal of ethnopharmacology.

[12]  J. C. Carvalho,et al.  In vivo Analgesic and Anti-Inflammatory Activities of Ursolic Acid and Oleanoic Acid from Miconia albicans (Melastomataceae) , 2006, Zeitschrift fur Naturforschung. C, Journal of biosciences.

[13]  P. Tu,et al.  The cytotoxic activity of ursolic acid derivatives. , 2005, European journal of medicinal chemistry.