Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (12): 3227-3235.DOI: 10.6023/cjoc201805030 Previous Articles     Next Articles



刘新宇a, 高雪琴a, 金学军b, 赵春晖c, 冯中华a, 隋悦a, 赵龙铉a,c, 阎欣d   

  1. a 辽宁师范大学化学化工学院 大连 116029;
    b 延边大学药学院 延吉 133002;
    c 辽宁师范大学 生物技术与药物分子研发辽宁省重点实验室 大连 116029;
    d 大连医科大学附属第三人民医院内科-肿瘤科学与教育系 大连 116200
  • 收稿日期:2018-05-15 修回日期:2018-06-15 发布日期:2018-08-23
  • 通讯作者: 赵龙铉, 阎欣;
  • 基金资助:


Synthesis, Characterization and Cytotoxic Activity of Novel Oleanolic Acid and Ursolic Acid Derivatives

Liu Xinyua, Gao Xueqina, Jin Xuejunb, Zhao Chunhuic, Feng Zhonghuaa, Sui Yuea, Zhao Longxuana,c, Yan Xind   

  1. a School of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029;
    b College of Pharmacy, Yanbian University, Yanji 133002;
    c Liaoning Provincial Key Laboratory of Biotechnology and Drug Discovery, Liaoning Normal University, Dalian 116029;
    d Science and Education Department, Internal Medicine-Oncology, Dalian Third People's Hospital Affiliated to Dalian Medical University, Dalian 116200
  • Received:2018-05-15 Revised:2018-06-15 Published:2018-08-23
  • Contact: 10.6023/cjoc201805030;
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21101067).

Twenty oleanolic acid and ursolic acid derivatives were prepared by a modification at C-28 position via introduction with 1,5-pentanedioic acid and glycolic acid followed by amidation with amines, such as morpholine, N-methyl piperazine and N-Boc-ethylenediamine. Their in vitro anticancer activities towards A549, MCF-7 and HepG2 cell lines were evaluated by 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl tetrazolium bromide (MTT) method. The results indicated that the anticancer activities of olean-2,12-diene-28-oic acid[1-(2-amino-ethylamino)-1-oxo]ethyl ester (OA-9d), urs-2,12-diene-28-oic acid[1-(2-amino-ethylamino)-1-oxo]ethyl ester (UA-9d) against A549, MCF-7 and HepG2 cells are obviously better than those of lead compounds. The ability of UA-9d to inhibit the expression of hypoxia inducible factor-1α (HIF-1α) in hepatocellular carcinoma Hep3B cells was determined by hypoxia response element (HRE)-dependent molecular assay. The results showed that UA-9d could effectively inhibit the expression of HIF-1α.

Key words: oleanolic acid, ursolic acid, cytotoxic activity