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

doi:10.6023/cjoc201805030

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

Articles

新型齐墩果酸和熊果酸衍生物的合成、表征及细胞毒活性研究

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

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 E-mail:lxzhao@lnnu.edu.cn;xiaoguai_xiaoen@163.com
基金资助:
国家自然科学基金（No.21101067）资助项目.

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

Liu Xinyu^a, Gao Xueqin^a, Jin Xuejun^b, Zhao Chunhui^c, Feng Zhonghua^a, Sui Yue^a, Zhao Longxuan^a,c, Yan Xin^d

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 E-mail:lxzhao@lnnu.edu.cn;xiaoguai_xiaoen@163.com
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21101067).

1. Synthesis, Characterization and Cytotoxic Activity of Novel Oleanolic Acid and Ursolic Acid Derivatives.PDF(2989KB)

Abstract

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

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Liu Xinyu, Gao Xueqin, Jin Xuejun, Zhao Chunhui, Feng Zhonghua, Sui Yue, Zhao Longxuan, Yan Xin. Synthesis, Characterization and Cytotoxic Activity of Novel Oleanolic Acid and Ursolic Acid Derivatives[J]. Chin. J. Org. Chem., 2018, 38(12): 3227-3235.

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新型齐墩果酸和熊果酸衍生物的合成、表征及细胞毒活性研究

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

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