Synthesis, Characterization and Anticancer Activity of Oleanolic Acid and Ursolic Acid Derivatives

doi:10.6023/cjoc201509002

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (4): 795-802.DOI: 10.6023/cjoc201509002 Previous Articles Next Articles

REVIEW

齐墩果酸和熊果酸衍生物的合成、表征及抗癌活性的研究

陈艳华^a, 侯熙彦^c, 支德福^c, 李常^a, 田甜^a, 孙竞阳^a, 赵龙铉^a,b, 赵春晖^b

a. 辽宁师范大学化学化工学院大连 116029;
b. 辽宁师范大学生物技术与分子药物研发辽宁省重点实验室大连 116029;
c. 大连民族大学生命科学学院大连 116600

收稿日期:2015-09-01 修回日期:2015-10-30 发布日期:2015-12-15
通讯作者: 赵龙铉, 赵春晖 E-mail:lxzhao@lnnu.edu.cn;zch@lnnu.edu.cn
基金资助:
国家自然科学基金(No.21101067)资助项目.

Synthesis, Characterization and Anticancer Activity of Oleanolic Acid and Ursolic Acid Derivatives

Chen Yanhua^a, Hou Xiyan^c, Zhi Defu^c, Li Chang^a, Tian Tian^a, Sun Jingyang^a, Zhao Longxuan^a,b, Zhao Chunhui^b

a. School of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029;
b. Liaoning Provincial Key Laboratory of Biotechnology and Drug Discovery, Liaoning Normal University, Dalian 116029;
c. College of Life Science, Dalian Nationalities University, Dalian 116600

Received:2015-09-01 Revised:2015-10-30 Published:2015-12-15
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21101067).

1. Synthesis, Characterization and Anticancer Activity of Oleanolic Acid and Ursolic Acid Derivatives.PDF(2193KB)

Abstract

Based on the combination principle, twelve novel oleanolic acid and ursolic acid derivatives were designed and synthesized through introduction of piperazine, N-methyl piperazine and morpholine moiety in C-28 position. Structures of all target compounds were characterized by IR, ¹H NMR, ¹³C NMR and HRMS. Their in vitro anticancer activities towards MCF-7, Hela and A549 cell lines were evaluated by a 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl tetrazolium bromide (MTT) method. The results indicate that OA-4, OA-7, OA-8a, OA-8b, UA-4, UA-7, UA-8a and UA-8b against MCF-7, Hela and A549 cells are obviously better than OA and UA, OA-4, OA-7, UA-4 and UA-7 are equally as well the IC₅₀of positive control gefitinib.

Key words: oleanolic acid, ursolic acid, piperazine, anticancer activity

Cite this article

Chen Yanhua, Hou Xiyan, Zhi Defu, Li Chang, Tian Tian, Sun Jingyang, Zhao Longxuan, Zhao Chunhui. Synthesis, Characterization and Anticancer Activity of Oleanolic Acid and Ursolic Acid Derivatives[J]. Chin. J. Org. Chem., 2016, 36(4): 795-802.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Zhang, D. F.; Huang, W.; Huang, J. Q.; Zhang, R. L.; Liao, Z. Q. Cancer Res. Prev. Treat. 2003, 30(3), 180 (in Chinese). (张东方, 黄炜, 黄济群, 张瑞玲, 廖兆全, 肿瘤防治研究, 2003, 30(3), 180.)
[2] Huang, D.; Ding, Y.; Li, Y.; Zhang, W.; Fang, W. M.; Chen, X. G. Cancer Lett. 2006, 233(2), 289.
[3] Ginerlarza, E. M.; Manez, S.; Recio, M. C.; Giner, R. M.; Prieto, J. M.; Cerdanicolas, M.; Rios, J. L. Eur. J. Pharmacol. 2001, 428(1), 137.
[4] Liu, J. J. Ethnopharmacol.2005, 100(1), 92.
[5] Liu, Z. B.; Wang, D.; Wang, S. Z.; Ha, S.; Li, P. W. Chin. Pharmacol. J. 1994, 29(12), 725 (in Chinese). (柳占彪, 王鼎, 王淑珍, 哈斯, 李浦维, 中国药学杂志, 1994, 29(12), 725.)
[6] Ali, M. S.; Jahangir, M.; Hussan, S. S.; Choudhary, M. I. Phytochemistry 2002, 60(3), 295.
[7] Tian, L. T.; Ma, L.; Du, N. S. China J. Chin. Mater. Med. 2002, 27(12), 884 (in Chinese). (田丽婷, 马龙, 堵年生, 中国中药杂志, 2002, 27(12), 884.)
[8] Zhang, P. X.; Li, H. M.; Chen, D.; Ge, T. D.; Whang, S. Q. Chin. J. Pathophysiol. 2008, 24(10), 1909 (in Chinese). (张鹏霞, 李鸿梅, 陈东, 葛堂栋, 王淑秋, 中国病理生理杂志, 2008, 24(10), 1909.)
[9] Huang, M. T.; Ho, C. T.; Wang, Z. Y.; Ferraro, T.; Lou, Y. R.; Stauber, K.; Ma, W.; Georgiadis, C.; Laskin, J. D.; Conney, A. H. Cancer Res. 1994, 54, 701.
[10] Rhew, T. H.; Park, S. M.; Park, K. Y.; Chung, H. Y.; Hah, J. C.; Lee, C. K. Yakhak Hoechi 1992, 36(6), 529.
[11] Huang, W.; Huang, J. Q.; Zhang, D. F.; Zhang, R. L.; Liao, Z. Q. Chin. J. Cancer Res. 2003, 6(4), 254 (in Chinese). (黄炜, 黄济群, 张东方, 张瑞玲, 廖兆全, 中国肺癌杂志, 2003, 6(4), 254.)
[12] Banno, N.; Akihisa, T.; Tokuda, H.; Yasukawa, K.; Higashihara, H.; Ukiya, M.; Watanabe, K.; Kimura, Y.; Hasegawa, Y.; Hasegawa, J, I.; Nishino, H. Biosci. Biotechnol. Biochem. 2004, 68(1), 85.
[13] Sohn, K. H.; Lee, H. Y.; Chung, H. Y.; Young, H. S.; Yi, S. Y.; Kim, K. W.Cancer Lett. 1995, 94(2), 213.
[14] Tan, J.; Shen, Z. X.; Geng, W. Chin. J. Oncol. 2006, 28(2), 99 (in Chinese). (谭洁, 沈志祥, 耿伟, 中华肿瘤杂志, 2006, 28(2), 99.)
[15] Wang, H.; Fang, J. H.; Li, H. J. J. Basic Clin. Oncol. 2010, 23(2), 93 (in Chinese). (王辉, 方全华, 李海军, 肿瘤基础与临床, 2010, 23(2), 93.)
[16] Li, J.; Guo, W. J.; Yang, Q. Y. World J. Gastroenterol. 2002, 8(3), 493.
[17] Ma, C. M.; Nakamura, N.; Miyashiro, H. Chem. Pharm. Bull. 1999, 47(2), 141.
[18] Buchdunger, E.; O'Reilly, T.; Wood, J. Eur. J. Cancer 2002, 38(Suppl. 5), 28.
[19] Johnson, F. M.; Saigal, B.; Talpaz, M.; Donato, N. J. Clin. Cancer Res. 2005, 11, 6924.
[20] Liu, D. Z.; Wang, D. F.; Song, L. L.; Zhao, D. Q.;Zhou, X. L.; Zhao, L. X. J. Dalian Univ. 2008, 29(6), 35 (in Chinese).

齐墩果酸和熊果酸衍生物的合成、表征及抗癌活性的研究

Synthesis, Characterization and Anticancer Activity of Oleanolic Acid and Ursolic Acid Derivatives

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Weishu Zhang, Lifei Nie, Khurshed Bozorov, Haji Akber Aisa, Jiangyu Zhao. Synthesis of Diethyl 2,5-Diaminothiophene-3,4-dicarboxylate Derivatives and Antitumor Activity Study [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2543-2552.
[2]	Jing Zhao, Zhe Jin, Run Wang, Xin'geng Zhang, Yingmei Han, Chun Hu, Xiaoping Liu, Chuanming Zhang, Liping Jin. Design, Synthesis and Anticancer Activity of 2-((Pyridin- 2-ylmethyl)thio)-1H-benzimidazole Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2172-2183.
[3]	Canbin Wang, Yu Lei, Xiaojian Liao, Shihai Xu, Bingxin Zhao. Two New 2,5-Dioxopiperazines from the Marine Sponge Haliclona baeri [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1839-1842.
[4]	Yan Zeng, Lifei Nie, Chao Niu, Aytilla Mamatjan, Khurshed Bozorov, Jiangyu Zhao, Haji Akber Aisa. Synthesis and Biological Activities of Dihydrooxazolo[5,4-d]-pyrrolo[1,2-a]pyrimidinones [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 543-556.
[5]	Xin Liu, Runmei Xu, Lin Wang, Yaxue Liu, Zhihao Chen, Wei Qin, Yushun Tian. Synthesis and Evaluation in vitro of Dihydrothiophenopyridine-Chalcone Derivatives as Anticancer Activity Agents [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3550-3559.
[6]	Shenghui Wang, Yongfeng Guan, Xiujuan Liu, Xinying Yuan, Guangxi Yu, Yinru Li, Yanbing Zhang, Jian Song, Wen Li, Saiyang Zhang. Design, Synthesis and Anticancer Activity Studies of Novel Quinoline-Indole Derivatives [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3617-3624.
[7]	Gaizhi Liu, Jinxin Li, Lijun Shi, Mengya Liu, Bangrong Cai. Advances in the Study of Structural Modification and Biological Activities of Ursolic Acid [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 2974-2989.
[8]	Liang Shao, Fan Yang, Weijia Li, Fei Yu. Design, Synthesis and Anti-influenza A Virus Evaluation of Oleanolic Acid C3-Glycoconjugates [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2454-2466.
[9]	Shuyun Zhang, Hang Liu, Lei Wang, Zhengming Li, Baolei Wang. Studies on the Synthesis, Structural Characterization and Biological Activities of Novel Caffeine Derivatives Containing Substituted-Piperazine Moiety [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 4075-4082.
[10]	Maihesuti Liwaliding, Yu Junjie, Wang Qi, Cao Jianguo, Huang Guozheng. Synthesis and Anticancer Evaluation of Amido-Derivative of Hydnocarpin D [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2764-2771.
[11]	Zhang Jingxing, Yao Tingting, Liu Jing, Li Huayue, Li Wenli. Recent Advances in Cyclodipeptide Synthases-Dependent Biosynthetic Pathway [J]. Chin. J. Org. Chem., 2019, 39(2): 328-338.
[12]	Mao Zewei, Liu Bei, Zhu Ping, Zhang Lijun, Zhu Jiahong, Wu Linze, Wan Chunping. Synthesis and Biological Evaluation of Piperazine Substituted 3-Aryl-5-furanyldihydropyrazole Amide Derivatives [J]. Chin. J. Org. Chem., 2018, 38(8): 2167-2173.
[13]	Huang Xinwei, Liu Jianli. Synthesis and Anticancer Activities of Novel Pyranocoumarin Fused Pyrimidine Based on Cyanoenamine [J]. Chin. J. Org. Chem., 2018, 38(5): 1233-1241.
[14]	Gao Hui, Zheng Xi, Zhu Ping, Wang Si, Wan Chunping, Rao Gaoxiong, Mao Zewei. Synthesis and Biological Evaluation of Novel Substituted Chalcone-piperazine Derivatives [J]. Chin. J. Org. Chem., 2018, 38(3): 684-691.
[15]	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.