Synthesis, Characteristics and Bioactivities of Novel Isosteviol Derivatives

doi:10.6023/cjoc201905029

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (12): 3532-3541.DOI: 10.6023/cjoc201905029 Previous Articles Next Articles

新型异甜菊醇衍生物的合成、表征及生物活性研究

郭永泰^a, 侯熙彦^b, 郑昌吉^c, 赵春晖^d, 金宇婷^a, 高雪琴^a, 王倩^a, 孙蕾^a, 赵龙铉^a,d, 朴花^e

a 辽宁师范大学化学化工学院辽宁大连 116029;
b 大连民族大学生命科学学院辽宁大连 116600;
c 延边大学药学院吉林延吉 133002;
e 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辽宁大连 116029;
e 大连医科大学基础医学院辽宁大连 116044

收稿日期:2019-05-13 修回日期:2019-06-26 发布日期:2019-08-01
通讯作者: 赵龙铉, 朴花 E-mail:lxzhao@lnnu.edu.cn;piaohua88@163.com
基金资助:
国家自然科学基金（No.21101067）资助项目.

Synthesis, Characteristics and Bioactivities of Novel Isosteviol Derivatives

Guo Yongtai^a, Hou Xiyan^b, Zheng Changji^c, Zhao Chunhui^d, Jin Yuting^a, Gao Xueqin^a, Wang Qian^a, Sun Lei^a, Zhao Longxuan^a,d, Piao Hua^e

a School of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian, Liaoning 116029;
b College of Life Science, Dalian Nationalities University, Dalian, Liaoning 116600;
c College of Pharmacy, Yanbian University, Yanji, Jilin 133002;
d Liaoning Provincial Key Laboratory of Biotechnology and Drug Discovery, Liaoning Normal University, Dalian, Liaoning 116029;
e Department of Physiology, College of Basic Medical Sciences, Dalian Medical University, Dalian, Liaoning 116044

Received:2019-05-13 Revised:2019-06-26 Published:2019-08-01
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21101067).

1. .pdf(1974KB)

Abstract

Fifteen novel isosteviol derivatives were designed and synthesized by introducing morpholine and piperazine moieties into C-16 and C-19 position through connecting fragments, and the D-ring structure was modified. The inhibitory effects on Colo-16 and A549 were observed, the results showed that the inhibitory activities of 4 compounds on Colo-16 were significantly better than the positive control of 5-fluorouracil. The inhibitory effects on E. coli 1924, S. aureus 4220, S. mutans 3289, MRSA 3167 and QRSA 3505 were also observed, the results showed that the minimum inhibitory concentration (MIC) of 6 compounds on S. mutans 3289 was 8 μg/mL, which was comparable to the positive control chloramphenicol. The MIC of 16β-O-(5-oxo-5-(4-methyl-1-piperazinyl)-valeryl)]-19-beyeran acid ethyl ester (IS-12b) on MRSA 3167 was 8 μg/mL, which was comparable to the positive control chloramphenicol.

Key words: isosteviol, cytotoxic activity, antibacterial activity

Cite this article

Guo Yongtai, Hou Xiyan, Zheng Changji, Zhao Chunhui, Jin Yuting, Gao Xueqin, Wang Qian, Sun Lei, Zhao Longxuan, Piao Hua. Synthesis, Characteristics and Bioactivities of Novel Isosteviol Derivatives[J]. Chinese Journal of Organic Chemistry, 2019, 39(12): 3532-3541.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Lin, J.; Guo, Y.; Gao, Y.; Wang, S.; Wang, X.; Xie, Z.; Niu, H.; Chang, W.; Liu, L.; Yuan, H.; Lou, H. J. Med. Chem. 2015, 58, 3944.
[2] Liu, C. J.; Yu, S. L.; Liu, Y. P.; Dai, X. J.; Wu, Y.; Li, R. J.; Tao, J. C. Eur. J. Med. Chem. 2016, 115, 26.
[3] Wang, M.; Li, H.; Xu, F.; Gao, X.; Li, J.; Xu, S.; Zhang, D.; Wu, X.; Xu, J.; Hua, H.; Li, D. Eur. J. Med. Chem. 2018, 156, 885.
[4] Luan, T.; Cao, L. H.; Deng, H.; Shen, Q. K.; Tian, Y. S.; Quan, Z. S. Molecules 2019, 24, 121.
[5] Wu, Y.; Liu, C. J.; Liu, X.; Dai, G. F.; Du, J. Y.; Tao, J. C. Helv. Chim. Acta 2010, 93, 2052.
[6] Hsieh, M. H.; Chan, P.; Sue, Y. M.; Liu, J. C.; Liang, T. H.; Huang, T. Y.; Tomlinson, B.; Chow, M.; Kao, P. F.; Chen, Y. J. Clin Ther. 2003, 25, 2797.
[7] Ma, J.; Ma, Z.; Wang, J.; Milne, R. W.; Xu, D.; Davey, A. K.; Evans, A. M. Diabetes, Obes. Metab. 2007, 9, 597.
[8] Samadder A.; Das, J.; Das, S.; Khuda, A. R. Environ. Toxicol. Pharmacol. 2012, 34, 743.
[9] Jin H.; Gerber J. P.; Wang J.; Ji, M.; Davey, A. K. J. Pharm. Biomed. Anal. 2008, 48, 986.
[10] Wong, K. L.; Lin, J. W.; Liu, J. C.; Yang, H. Y.; Kao, P. F.; Chen, C. H.; Loh, S. H.; Chiu, W. T.; Cheng, T. H.; Lin, J. G.; Hong, H. J. Pharmacology 2006, 76, 163.
[11] Hutt, O. E.; Doan, T. L.; Georg, G. I. Org. Lett. 2013, 15, 1602.
[12] Zhu, S. L.; Wu, Y.; Liu, C. J.; Wei, C. Y.; Tao, J. C.; Liu, H. M. Eur. J. Med. Chem. 2013, 65, 70.
[13] Tian, T.; Liu, X.; Lee, E. S.; Sun, J.; Feng, Z.; Zhao, L.; Zhao, C. Arch. Pharmacal Res. 2017, 40, 458.
[14] 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](陈艳华, 侯熙彦, 支德福, 李常, 田甜, 孙竞阳, 赵龙铉, 赵春晖, 有机化学, 2016, 36, 795.)
[15] Liu, X. Y.; Gao, X. H. Q.; Jin, X. J.; Zhao, C. H.; Feng, Z. H.; Sui, Y.; Zhao, L. X.; Yan, X. Chin. J. Org. Chem. 2018, 38, 3227(in Chinese). (刘新宇, 高雪琴, 金学军, 赵春晖, 冯中华, 隋悦, 赵龙铉, 阎欣, 有机化学, 2018, 38, 3227.)
[16] Lohoelter, C.; Weckbecker, M.; Waldvogel, S. R. Eur. J. Org. Chem. 2013, 2013, 5539.
[17] Zhang, T.; Lu, L. H.; Liu, H.; Wang, J. W.; Wang, R. X.; Zhang, Y. X.; Tao, J. C. Bioorg. Med. Chem. Lett. 2012, 22, 5827.
[18] Liu, C. J.; Liu, Y. P.; Yu, S. L.; Dai, X. J.; Zhang, T.; Tao, J. C. Bioorg. Med. Chem. Lett. 2016, 26, 5455.
[19] Murillo, J. A.; Gil, J. F.; Upegui, Y. A.; Restrepo, A. M.; Robledo, S. M.; Quiñones, W.; Echeverri, F.; Martin, A. S.; Olivo, H. F.; Escobar, G. Bioorg. Med. Chem. 2019, 27, 153.
[20] Xing, X. L.; Liu, T. T.; Song, M. X.; Li, Y. R.; Zhang, Y.; Li, Y.; Li, H. S.; Zheng, C. J.; Piao, H. R. Chin. J. Med. 2013, 23, 1(in Chinese). (邢肖兰, 刘婷婷, 宋明霞, 李亚茹, 张雨, 李燕, 李花淑, 郑昌吉, 朴虎日, 中国药物化学杂志, 2013, 23, 1.)

新型异甜菊醇衍生物的合成、表征及生物活性研究

Synthesis, Characteristics and Bioactivities of Novel Isosteviol Derivatives

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Haibo Huo, Guixia Li, Shijun Wang, Chun Han, Baojun Shi, Jian Li. Novel γ-Carboline Derivatives as Antibacterial Agents: Synthesis and Antibacterial Evaluation [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 204-215.
[2]	Weizhong Ding, Bingwen Zhang, Yanqing Xue, Yuqi Lin, Zhijun Tang, Jing Wang, Wenchao Yang, Xiaofeng Wang, Wen Liu. A New Polyketide from Fusarium graminearum [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3319-3322.
[3]	Yifang Chen, Xin Luo, Yu Wang, Zhifu Xing, Ju Peng, Jixiang Chen. Design, Synthesis and Antibacterial Activity of 1,3,4-Oxadiazole Sufones Containing Sulfonamide Structure [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 274-284.
[4]	Dan Huang, Xuhua Nong, Jianni Yang, Chen Li, Changri Han, Guangying Chen, Xiaoping Song, Zhenfan Sun, Yang Hui, Wenhao Chen. Study on the Secondary Metabolites of the Endophytic Fungus Aspergillus terreus HQ100X-1 in Scutellaria formosana [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2961-2966.
[5]	Huanhuan Wang, Pu Yang, Hongjin Zhai, Shuo Zhang, Yaquan Cao, Yingxue Yang, Chunli Wu. Design, Synthesis and Activity Evaluation of New Tylosin Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 557-572.
[6]	Ali Dai, Renfeng Zhang, Chuanhui Li, Lijiao Yu, Ya Wang, Jian Wu. Synthesis and Biological Activity of N-Cyano Sulfonimide Derivatives Bearing Trifluoromethyl Pyridinamide [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3633-3642.
[7]	Feng He, Shengxin Guo, Ali Dai, Renfeng Zhang, Jian Wu. Synthesis, Characterization, and Biological Activity of Novel Amide Derivatives Containing Trifluoromethylpyridine Moieties [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3303-3311.
[8]	Shao Lihui, Gan Yiyuan, Hou Mi, Tao Shilin, Zhang Liqiong, Wang Zhenchao, Ouyang Guiping. Design, Synthesis and Biological Activity of Quinazolinone Derivatives Containing Hydrazone Structural Units [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 1975-1982.
[9]	Ji Yu, Yao Hui, Liu Yi, Huang Nianyu, Liu Mingguo. Synthesis and Cytotoxic Activity of C-Vinyl-rhamnopyranoside Derivatives [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2051-2061.
[10]	Liu Zhengfen, Zi Yujin, Zhang Linlin, Fang Yongsheng, Shen Yanzhen, Li Yan, Yang Xiaodong, Zhang Hongbin. Synthesis and Cytotoxic Activity of Novel Hybrid Compounds between Piperonyl and Imidazolium Salts [J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 669-678.
[11]	Li Yongkun, Tang Yanling, Li Minxin, Yang Xiaobi, Gao Hui, Mao Zewei. Synthesis and Antibacterial Activity of Thienyl Chalcone Derivatives Bearing Piperazine Moiety [J]. Chinese Journal of Organic Chemistry, 2020, 40(1): 108-114.
[12]	Fu Lin, Sun Bingxia, Zhai Jiadai, Li Yuanyuan, Liu Xinqiang, Song Ru, Shi Guanqun, Li Jiaona, Song Yuanxia, Sang Feng. Synthesis and Antibacterial Activity Study of Natural 5'-Hydroxyisoprenyl Chalcones [J]. Chinese Journal of Organic Chemistry, 2020, 40(1): 201-208.
[13]	He Wenjing, Liu Denyue, Gan Xiuhai, Zhang Jian, Liu Zhengjun, Yi Chongfen, Song Bao'an. Synthesis and Biological Activity of Novel 1,3,4-Thiadiazolo[3,2-a]pyrimidinone Mesoionic Derivatives [J]. Chin. J. Org. Chem., 2019, 39(8): 2287-2294.
[14]	Ding Chengrong, Pan Yayun, Yin Xu, Tan Chengxia. Synthesis and Biological Activity of Thiazolidine Piperidine Nicotinamide Compounds [J]. Chin. J. Org. Chem., 2019, 39(7): 2099-2105.
[15]	Mei Rongqing, Huang Guolei, Wang Bin, Bai Meng, Luo Youping, Chen Guangying, Zheng Caijuan. Two New Isocoumarins Isolated from a Mangrove-Derived Fungus Penicillium citrinum HL-5126 [J]. Chin. J. Org. Chem., 2019, 39(5): 1479-1482.