Citation: Liao Shili, Zhang Guogai, Cao Han, Chen Biying, Li Weimin, Wu Xia, Feng Yifan. Synthesis and Anti-tumor Activities against HepG2 Cell in vitro of the Conjugates of Honokiol, Quercetin and Berberine[J]. Chinese Journal of Organic Chemistry, ;2018, 38(6): 1549-1555. doi: 10.6023/cjoc201801023 shu

Synthesis and Anti-tumor Activities against HepG2 Cell in vitro of the Conjugates of Honokiol, Quercetin and Berberine

Liao Shili ^a ,
Zhang Guogai ^a ,
Cao Han ^a ,
Chen Biying ^a ,
Li Weimin ^b,, ,
Wu Xia ^a,, ,
Feng Yifan ^a,,

a.
Central Laboratory, Guangdong Pharmaceutical University, Guangzhou 510000
b.
College of Chinese Materia Medica, Guangzhou University of Chinese Medicine, Guangzhou 510000

Corresponding author: Li Weimin, 13925023915@139.com Wu Xia, wxiaxia@163.com Feng Yifan, yffeng@139.com
Received Date: 26 January 2018
Revised Date: 27 February 2018
Available Online: 8 June 2018
Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 21275036, 81202429)the National Natural Science Foundation of China 81202429the National Natural Science Foundation of China 21275036

Figures(4)

Berberine, honokiol, quercetin are the lead compounds with outstanding anti-tumor activities. Three novel products were synthesized from honokiol, quercetin and berberine. The structures of the products were firstly confirmed by ¹H NMR, ¹³C NMR, 2D NMR, HRMS, IR and UV. All products were evaluated for their anti-tumor activities against HepG2 cell in vitro and the results showed that the inhibitory effects of two compounds on HepG2 cell were far superior to honokiol and berberine hydrochloride, and the anti-tumor activities were similar to the reference drug cisplatin. It means that compounds 1 and 2 are expected to be the potential anti-tumor drugs.
- berberine,
- honokiol,
- quercetin,
- anti-tumor activity
1. [1]
  Zhang, S. L.; Chang, J. J.; Damu, G.; Fang, B.; Zhou, X. D.; Geng, R. X.; Zhou, C. H. Bioorg.Med.Chem.Lett. 2013, 23, 1008. doi: 10.1016/j.bmcl.2012.12.036
2. [2]
  Lin, C. F.; Hung, C. F.; Aljuffali, I. A.; Huang, Y. L.; Liao, W. C.; Fang, J. Y. Pharm.Res. 2016, 33, 2152. doi: 10.1007/s11095-016-1953-x
3. [3]
  Hu, Y.; Davies, G. E. Fitoterapia 2010, 81, 358. doi: 10.1016/j.fitote.2009.10.010
4. [4]
  Wang, X. H.; Duan, X. M.; Yang, G. L.; Zhang, X. Y.; Deng, L. Y.; Zheng, H.; Deng, C. Y.; Wen, J. L.; Wang, N. Peng, C.; Zhao, X.; Wei, Y. Q.; Chen, L. J. Plos One 2011, 6, e18490. doi: 10.1371/journal.pone.0018490
5. [5]
  Chiang, J.; Shen, Y. C.; Wang, Y. H.; Hou, Y. C.; Chen, C. C.; Liso, J. F.; Y, M. C.; Juan, C. W.; Liou, K. T. Eur.J.Pharmacol. 2009, 610, 119. doi: 10.1016/j.ejphar.2009.03.035
6. [6]
  Mendoza, E. E.; Burd, R. Mini-Rev. Med. Chem. 2011, 11, 1216.
7. [7]
  Patil, J. B.; Kim, J.; Jayaprakasha, G. K. Eur.J.Pharmacol. 2010, 645, 70. doi: 10.1016/j.ejphar.2010.07.037
8. [8]
  Zhou, B.; Li, H. Y.; Xing, C. Y.; Ye, H. G.; Feng, J. H.; Wu, J. B.; Lu, Z. Q.; Fang, J.; Gao, S. M. Biochem.Pharmacol. 2017, 128, 12. doi: 10.1016/j.bcp.2016.12.022
9. [9]
  Fang, J. Y.; Huang, T. H.; Hung, C. F.; Huang, Y. L.; Aljuffali, I. A.; Liao, W. C.; Lin, C. F. Eur.J.Pharm.Sci. 2018, 114, 189. doi: 10.1016/j.ejps.2017.12.007
10. [10]
  Garelnabi, M.; Mahini, H.; Wilson, T. J.Int.Soc.Sport.Nutr. 2014, 11, 22. doi: 10.1186/1550-2783-11-22
11. [11]
  Enkhtaivan, G.; Muthuraman, P.; Kim D. H.; Mistry, B. Bioorg.Med.Chem. 2017, 25, 5185. doi: 10.1016/j.bmc.2017.07.006
12. [12]
  Mistry, B.; Patel, R. V.; Keum, Y. S.; Kim D. H. J.Saudi Chem. Soc. 2017, 21, 210. doi: 10.1016/j.jscs.2015.11.002
13. [13]
  Ma, L.; Chen, J. Y.; Wang, X. W.; Liang, X. L. J.Med.Chem. 2011, 54, 6469. doi: 10.1021/jm200830u
14. [14]
  Lin, C. F. Int.J.Pharm. 2013, 445, 153. doi: 10.1016/j.ijpharm.2013.01.049
15. [15]
  Mattarei, A.; Biasutto, L.; Rastrelli, F.; Garbisa, S.; Marotta, E. Molecules 2010, 15, 4722. doi: 10.3390/molecules15074722
16. [16]
  Zhou, Z. H.; Fang, Z.; Jin, H.; Chen, Y. Synthesis 2010, 23, 3980.
17. [17]
  Cao, H; Liao, S. L; Zhong, W. J.; Xiao, X. R.; Zhu, J. C. Molecules 2017, 22, 1752. doi: 10.3390/molecules22101752
18. [18]
  Cao, Y. B. ; Sun, Q. ; Jin, J. ; Li, X. M. CN 104119330, 2014[Abstr. Chem. 2014, 161, 698825].
19. [19]
  Nechepurenko, I. V.; Komarova, N. I.; Vasil'ev, V. G.; Salakhutdinov, N. F. Chem.Nat.Compd. 2013, 48, 1047. doi: 10.1007/s10600-013-0461-z
20. [20]
  Zhang, L. M. S. Thesis, Guangzhou University of Chinese Medicine, Guangzhou, 2015(in Chinese).
1. [1]
  Fei-Yan Gao , Yan Wu , Ling Yang , Zhong-Yi Ma , Yi Chen , Xiao-Man Mao , Xu-Fei Bian , Pei Tang , Chong Li . Orally delivered berberine derivatives for dual therapy in diabetic complications with MRSA infections. Chinese Chemical Letters, 2025, 36(4): 109917-. doi: 10.1016/j.cclet.2024.109917
2. [2]
  Qianyun Ye , Yuanyuan Liang , Yuhe Yuan , Xiaohuan Sun , Liqi Zhu , Xuan Wu , Jie Han , Rong Guo . pH-responsive chiral supramolecular cysteine-Zn²⁺-indocyanine green assemblies for triple-level chirality-specific anti-tumor efficacy. Chinese Chemical Letters, 2025, 36(5): 110432-. doi: 10.1016/j.cclet.2024.110432
3. [3]
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4. [4]
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5. [5]
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6. [6]
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7. [7]
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8. [8]
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9. [9]
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10. [10]
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11. [11]
  Ting Wang , Xin Yu , Yaqiang Xie . Unlocking stability: Preserving activity of biomimetic catalysts with covalent organic framework cladding. Chinese Chemical Letters, 2024, 35(6): 109320-. doi: 10.1016/j.cclet.2023.109320
12. [12]
  Fangping Yang , Jin Shi , Yuansong Wei , Qing Gao , Jingrui Shen , Lichen Yin , Haoyu Tang . Mixed-charge glycopolypeptides as antibacterial coatings with long-term activity. Chinese Chemical Letters, 2025, 36(2): 109746-. doi: 10.1016/j.cclet.2024.109746
13. [13]
  Chong Liu , Ling Li , Jiahui Gao , Yanwei Li , Nazhen Zhang , Jing Zang , Cong Liu , Zhaopei Guo , Yanhui Li , Huayu Tian . The study of antibacterial activity of cationic poly(β-amino ester) regulating by amphiphilic balance. Chinese Chemical Letters, 2025, 36(2): 110118-. doi: 10.1016/j.cclet.2024.110118
14. [14]
  Di ZHANG , Tianxiang XIE , Xu HE , Wanyu WEI , Qi FAN , Jie QIAO , Gang JIN , Ningbo LI . Construction and antitumor activity of pH/GSH dual-responsive magnetic nanodrug. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 786-796. doi: 10.11862/CJIC.20240329
15. [15]
  Kun Zhang , Ni Dan , Dan-Dan Ren , Ruo-Yu Zhang , Xiaoyan Lu , Ya-Pan Wu , Li-Lei Zhang , Hong-Ru Fu , Dong-Sheng Li . A small D-A molecule with highly heat-resisting room temperature phosphorescence for white emission and anti-counterfeiting. Chinese Journal of Structural Chemistry, 2024, 43(3): 100244-100244. doi: 10.1016/j.cjsc.2024.100244
16. [16]
  Qiang Li , Jiangbo Fan , Hongkai Mu , Lin Chen , Yongzhen Yang , Shiping Yu . Nucleus-targeting orange-emissive carbon dots delivery adriamycin for enhanced anti-liver cancer therapy. Chinese Chemical Letters, 2024, 35(6): 108947-. doi: 10.1016/j.cclet.2023.108947
17. [17]
  Ji Zhang , Tong Zhang , Qiao An , Peng Zhang , Cai-Yan Tian , Chun-Mao Yuan , Ping Yi , Zhan-Xing Hu , Xiao-Jiang Hao . Five quinolizidine alkaloids with anti-tobacco mosaic virus activities from two species of Sophora. Chinese Chemical Letters, 2024, 35(6): 108927-. doi: 10.1016/j.cclet.2023.108927
18. [18]
  Xiaoning Li , Quanyu Shi , Meng Li , Ningxin Song , Yumeng Xiao , Huining Xiao , Tony D. James , Lei Feng . Functionalization of cellulose carbon dots with different elements (N, B and S) for mercury ion detection and anti-counterfeit applications. Chinese Chemical Letters, 2024, 35(7): 109021-. doi: 10.1016/j.cclet.2023.109021
19. [19]
  Changle Liu , Mingyuzhi Sun , Haoran Zhang , Xiqian Cao , Yuqing Li , Yingtang Zhou . All in one doubly pillared MXene membrane for excellent oil/water separation, pollutant removal, and anti-fouling performance. Chinese Journal of Structural Chemistry, 2024, 43(8): 100355-100355. doi: 10.1016/j.cjsc.2024.100355
20. [20]
  Jiayin Zhou , Depeng Liu , Longqiang Li , Min Qi , Guangqiang Yin , Tao Chen . Responsive organic room-temperature phosphorescence materials for spatial-time-resolved anti-counterfeiting. Chinese Chemical Letters, 2024, 35(11): 109929-. doi: 10.1016/j.cclet.2024.109929

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