Citation: 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]. Chinese Journal of Organic Chemistry, ;2018, 38(12): 3227-3235. doi: 10.6023/cjoc201805030 shu

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

Corresponding author: Zhao Longxuan, lxzhao@lnnu.edu.cn Yan Xin, xiaoguai_xiaoen@163.com
Received Date: 15 May 2018
Revised Date: 15 June 2018
Available Online: 23 December 2018
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21101067)the National Natural Science Foundation of China 21101067

Figures(6)

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.
- oleanolic acid,
- ursolic acid,
- cytotoxic activity
1. [1]
  Liu, J. J. Ethnopharmacol. 2005, 100, 92. doi: 10.1016/j.jep.2005.05.024
2. [2]
  Meng, Y. Q.; Liu, D.; Cai, L. L.; Chen, H.; Cao, B.; Wang, Y. Z. Bioorg. Med. Chem. 2009, 17, 848.
3. [3]
  Kashiwada, Y.; Nagao, T.; Hashimoto, A.; Ikeshiro, Y.; Okabe, H.; Cosentino, L. M.; Lee, K. H. J. Nat. Prod. 2000, 63, 1619. doi: 10.1021/np990633v
4. [4]
  Saraswat, B.; Visen, P. S.; Agarwal, D. P. Phytother. Res. 2000, 14, 163. doi: 10.1002/(ISSN)1099-1573
5. [5]
  Traorekeita, F.; Gasquet, M.; Di, G. C.; Ollivier, E.; Delmas, F.; Keita, A.; Doumbo, O.; Balansard, G.; Timondavid, P. Phytother. Res. 2000, 14, 45. doi: 10.1002/(ISSN)1099-1573
6. [6]
  Chattopadhyay, D.; Arunachalam, G.; Mandal, A. B.; Sur, T. K.; Mandal, S. C.; Bhattacharya, S. K. J. Ethnopharmacol. 2002, 82, 229. doi: 10.1016/S0378-8741(02)00165-4
7. [7]
  Liu, D.; Meng, Y. Q.; Zhao, J.; Chen, L. G. Chem. Res. Chin. Univ. 2008, 24, 42. doi: 10.1016/S1005-9040(08)60010-0
8. [8]
  Ma, C. M.; Cai, S. Q.; Cui, J. R.; Wang, R. Q.; Tu, P. F.; Hattori, M.; Daneshtalab, M. Eur. J. Med. Chem. 2005, 40, 582 doi: 10.1016/j.ejmech.2005.01.001
9. [9]
  Tian, Z.; Lin, G.; Zheng, R. X.; Huang, F.; Yang, M. S.; Xiao, P. G. World J. Gastroenterol. 2006, 12, 874. doi: 10.3748/wjg.v12.i6.874
10. [10]
  Shanmugam, M. K.; Dai, X.; Kumar, A. P.; Tan, B. K. H.; Sethi, G.; Bishayee, A. Cancer Lett. 2014, 346, 206. doi: 10.1016/j.canlet.2014.01.016
11. [11]
  Kim, K. A.; Lee, J. S.; Park, H. J.; Kim, J. W.; Kim, C. J.; Shim, I. S.; Kim, N. J.; Han, S. M.; Lim, S. Life Sci. 2004, 74, 2769. doi: 10.1016/j.lfs.2003.10.020
12. [12]
  Aparecida, R. F.; Ca, D. A. B.; Da, S. F. M.; Kato, F. H.; Cunha, W. R.; Tavares, D. C. Life Sci. 2006, 79, 1268. doi: 10.1016/j.lfs.2006.03.038
13. [13]
  Chen, Y. H.; Hou, X. Y.; Zhi, D. F.; Li, C.; Tian, T.; Sun, J. Y.; Zhao, L. X.; Zhao, C. H. Chin. J. Org. Chem. 2016, 36, 795(in Chinese).
14. [14]
  Tian, T.; Liu, X. Y.; Lee, E. S.; Sun, J. Y.; Feng, Z. H.; Zhao, L. X.; Zhao, C. H. Arch. Pharmacol. Res. 2017, 40, 458. doi: 10.1007/s12272-016-0868-8
15. [15]
  Liu, D. Z. M.S. Thesis, Liaoning Normal University, Dalian, 2009(in Chinese).
16. [16]
  Feng, J. H. Ph. D. Dissertation, Zhejiang University, Hangzhou, 2006(in Chinese).
1. [1]
  Gaofeng Zeng , Shuyu Liu , Manle Jiang , Yu Wang , Ping Xu , Lei Wang . Micro/Nanorobots for Pollution Detection and Toxic Removal. University Chemistry, 2024, 39(9): 229-234. doi: 10.12461/PKU.DXHX202311055
2. [2]
  Zhaoxin LI , Ruibo WEI , Min ZHANG , Zefeng WANG , Jing ZHENG , Jianbo LIU . Advancements in the construction of inorganic protocells and their cell mimic and bio-catalytical applications. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2286-2302. doi: 10.11862/CJIC.20240235
3. [3]
  Shuyu Liu , Xiaomin Sun , Bohan Song , Gaofeng Zeng , Bingbing Du , Chongshen Guo , Cong Wang , Lei Wang . Design and Fabrication of Phospholipid-Vesicle-based Artificial Cells towards Biomedical Applications. University Chemistry, 2024, 39(11): 182-188. doi: 10.12461/PKU.DXHX202404113
4. [4]
  Siyi ZHONG , Xiaowen LIN , Jiaxin LIU , Ruyi WANG , Tao LIANG , Zhengfeng DENG , Ao ZHONG , Cuiping HAN . Targeting imaging and detection of ovarian cancer cells based on fluorescent magnetic carbon dots. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1483-1490. doi: 10.11862/CJIC.20240093
5. [5]
  Shipeng WANG , Shangyu XIE , Luxian LIANG , Xuehong WANG , Jie WEI , Deqiang WANG . Piezoelectric effect of Mn, Bi co-doped sodium niobate for promoting cell proliferation and bacteriostasis. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1919-1931. doi: 10.11862/CJIC.20240094
6. [6]
  Peng GENG , Guangcan XIANG , Wen ZHANG , Haichuang LAN , Shuzhang XIAO . Hollow copper sulfide loaded protoporphyrin for photothermal-sonodynamic therapy of cancer cells. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1903-1910. doi: 10.11862/CJIC.20240155
7. [7]
  Jiahao Zeng , Hui Chao . 诱导程序性细胞死亡的金属抗肿瘤药物研究. University Chemistry, 2025, 40(6): 145-159. doi: 10.12461/PKU.DXHX202406019
8. [8]
  Quanliang Chen , Zhaohui Zhou . Research on the Active Site of Nitrogenase over Fifty Years. University Chemistry, 2024, 39(7): 287-293. doi: 10.3866/PKU.DXHX202310133
9. [9]
  Di WU , Ruimeng SHI , Zhaoyang WANG , Yuehua SHI , Fan YANG , Leyong ZENG . Construction of pH/photothermal dual-responsive delivery nanosystem for combination therapy of drug-resistant bladder cancer cell. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1679-1688. doi: 10.11862/CJIC.20240135
10. [10]
  Xinyu ZENG , Guhua TANG , Jianming OUYANG . Inhibitory effect of Desmodium styracifolium polysaccharides with different content of carboxyl groups on the growth, aggregation and cell adhesion of calcium oxalate crystals. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1563-1576. doi: 10.11862/CJIC.20230374
11. [11]
  Yanxi LIU , Mengjia XU , Haonan CHEN , Quan LIU , Yuming ZHANG . A fluorescent-colorimetric probe for peroxynitrite-anion-imaging in living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1112-1122. doi: 10.11862/CJIC.20240423
12. [12]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
13. [13]
  Yukai Jiang , Yihan Wang , Yunkai Zhang , Yunping Wei , Ying Ma , Na Du . Characterization and Phase Diagram of Surfactant Lyotropic Liquid Crystal. University Chemistry, 2024, 39(4): 114-118. doi: 10.3866/PKU.DXHX202309033
14. [14]
  Jiayu Gu , Siqi Wang , Jun Ling . Kinetics of Living Copolymerization: A Brief Discussion. University Chemistry, 2025, 40(4): 100-107. doi: 10.12461/PKU.DXHX202406012
15. [15]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
16. [16]
  Chunmei GUO , Weihan YIN , Jingyi SHI , Jianhang ZHAO , Ying CHEN , Quli FAN . Facile construction and peroxidase-like activity of single-atom platinum nanozyme. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1633-1639. doi: 10.11862/CJIC.20240162
17. [17]
  Congying Lu , Fei Zhong , Zhenyu Yuan , Shuaibing Li , Jiayao Li , Jiewen Liu , Xianyang Hu , Liqun Sun , Rui Li , Meijuan Hu . Experimental Improvement of Surfactant Interface Chemistry: An Integrated Design for the Fusion of Experiment and Simulation. University Chemistry, 2024, 39(3): 283-293. doi: 10.3866/PKU.DXHX202308097
18. [18]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
19. [19]
  Qiqi Li , Su Zhang , Yuting Jiang , Linna Zhu , Nannan Guo , Jing Zhang , Yutong Li , Tong Wei , Zhuangjun Fan . 前驱体机械压实制备高密度活性炭及其致密电容储能性能. Acta Physico-Chimica Sinica, 2025, 41(3): 2406009-. doi: 10.3866/PKU.WHXB202406009
20. [20]
  Changqing MIAO , Fengjiao CHEN , Wenyu LI , Shujie WEI , Yuqing YAO , Keyi WANG , Ni WANG , Xiaoyan XIN , Ming FANG . Crystal structures, DNA action, and antibacterial activities of three tetranuclear lanthanide-based complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2455-2465. doi: 10.11862/CJIC.20240192

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(1770)
HTML views(353)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142