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

被引：2

作者：

Liu, Xinyu ^{[1
]}

Gao, Xueqin ^{[1
]}

Jin, Xuejun ^{[2
]}

Zhao, Chunhui ^{[3
]}

Feng, Zhonghua ^{[1
]}

Sui, Yue ^{[1
]}

Zhao, Longxuan ^{[1
,3
]}

Yan, Xin ^{[4
]}

机构：

[1] Liaoning Normal Univ, Sch Chem & Chem Engn, Dalian 116029, Peoples R China

[2] Yanbian Univ, Coll Pharm, Yanji 133002, Peoples R China

[3] Liaoning Nonnal Univ, Liaoning Prov Key Lab Biotechnol & Drug Discovery, Dalian 116029, Peoples R China

[4] Dalian Med Univ, Sci & Educ Dept, Internal Med Oncol, Dalian Peoples Hosp 3, Dalian 116200, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 38卷 / 12期

基金：

中国国家自然科学基金;

关键词：

oleanolic acid; ursolic acid; cytotoxic activity; MECHANISM;

D O I：

10.6023/cjoc201805030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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-1 alpha (HCF-1 alpha) 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-1 alpha.

引用

页码：3227 / 3235

页数：9

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