Citation: Pan Guojun, Xiao Na, Shen Di, Chen Minglang, Li Yi, Lu Kui, Yang Yang, Meng Xin, Yu Peng. Synthesis and Hypoglycemic Activity of Novel Quercetin Conjugates[J]. Chinese Journal of Organic Chemistry, ;2017, 37(1): 133-140. doi: 10.6023/cjoc201608002 shu

Synthesis and Hypoglycemic Activity of Novel Quercetin Conjugates

Pan Guojun ^a ,
Xiao Na ^b ,
Shen Di ^a ,
Chen Minglang ^a ,
Li Yi ^b ,
Lu Kui ^a ,
Yang Yang ^a ,
Meng Xin ^a,*,, ,
Yu Peng ^a,*,,

a.
College of Technology, Tianjin University of Science and Technology, Tianjin 300457
b.
College of Traditional Chinese Medicine, China Pharmaceutical University, Nanjing 210000

Corresponding author: Meng Xin, mengxin@tust.edu.cn Yu Peng, yupeng@tust.edu.cn
Received Date: 2 August 2016
Revised Date: 5 September 2016

Fund Project: the National Natural Science Foundation of China 21402140the Science and Technology Commissioner Foundation of Tianjin 15JCTPJC56200the National Natural Science Foundation of China 21502139

Figures(3)

Eight novel quercetin conjugates 20~27 were successfully synthesized through a concise procedure with 15%~46% overall yields by using Rutin as the starting material. After O-benzylation, glycoside hydrolysis and O-propargylation, rutin was converted to the key intermediate 5, 7, 3', 4'-tetrabenzyloxy-3-O-propargylquercetin, which subsequently 'clicked' with azido containing glycosides, poly (ethylene glycol) (PEG) or oligo (ethylene glycol) (OEG) to provide the fully protected quercetin conjugates 12~19. After global deprotection, the resulting quercetin conjugates were evaluated on hypoglycemic activities at 3T3-L1 adipocyte level. The results showed that conjugates 24, 26 and 27 exhibited good hypoglycemic effects.
- quercetin conjugate,
- click reaction,
- synthesis,
- hypoglycemic activity,
- adipocyte
1. [1]
  Seo, M. J.; Lee, Y. J.; Hwang, J. H.; Kim, K. J.; Lee, B. Y. J. Nutr. Biochem. 2015, 11, 1308.
2. [2]
  Kim, C. S.; Kwon, Y.; Choe, S. Y.; Hong, S. M.; Yoo, H.; Goto, T.; Kawada, T.; Choi, H. S.; Joe, Y.; Chung, H. T.; Yu, R. Nutr. Metab. (Lond) 2015, 12, 33. doi: 10.1186/s12986-015-0030-5
3. [3]
  Mahmoud, M. F.; Hassan, N. A.; El Bassossy, H. M.; Fahmy, A. PLoS One 2013, 8, e63784. doi: 10.1371/journal.pone.0063784
4. [4]
  Hertog, M. G.; Bueno-de-Mesquita, H. B.; Fehily, A. M.; Sweetnam, P. M.; Elwood, P. C. Cancer Epidemiol. Biomarkers Prev. 1996, 5, 673.
5. [5]
  Shoskes, D. A.; Nickel, J. C. Urologic Clinics North Am. 2011, 38, 279. doi: 10.1016/j.ucl.2011.05.003
6. [6]
  Liu, K.; Mei, F.; Wang, Y. P.; Xiao, N.; Yang, L. L.; Wang, Y. L.; Li, J.; Huang, F.; Kou, J. P.; Liu, B. L; Qi, L. W. Mol. Nutr. Food Res. 2016, 60, 551. doi: 10.1002/mnfr.201500509
7. [7]
  Bhadada, S. V.; Vyas, V. K.; Goyal, R. K. Biomed. Pharmacother. 2016, 83, 221. doi: 10.1016/j.biopha.2016.05.018
8. [8]
  Casado-Díaz, A.; Anter, J.; Dorado, G.; Quesada-Gómez, J. M. J. Nutr. Biochem. 2016, 32, 151. doi: 10.1016/j.jnutbio.2016.03.005
9. [9]
  Stefek, M.; Karasu, C. Rejuvenation Res. 2011, 14, 525. doi: 10.1089/rej.2011.1170
10. [10]
  Mei, Q. G.; Yuan, W. C.; Wang, C. Chin. J. Org. Chem. 2015, 35, 70 (in Chinese). doi: 10.6023/cjoc201408038
11. [11]
  Wang, Q. A.; Wu, Z.; Liu, L.; Zou, L. H.; Luo, M. Chin. J. Org. Chem. 2010, 30, 1682 (in Chinese).
12. [12]
  Yan, X.; Liu, H. Q.; Zou, Y. Q.; Ren, Z. H. Chin. J. Org. Chem. 2008, 28, 1534 (in Chinese).
13. [13]
  Teng, Y. O.; Zhao, H. Y.; Wang, J.; Liu, H.; Gao, M. L.; Zhou, Y.; Han, K. L.; Fan, Z. C.; Zhang, Y. M.; Sun, H.; Yu, P. Eur. J. Med. Chem. 2016, 112, 145. doi: 10.1016/j.ejmech.2015.12.050
14. [14]
  Sun, H.; Li, Y. S.; Zhang, X. T.; Lei, Y. N.; Ding, W. N.; Zhao, X.; Wang, H. M.; Song, X. T.; Yao, Q. W.; Zhang, Y. M.; Ma, Y.; Wang, R.; Zhu, T.; Yu, P. Bioorg. Med. Chem. Lett. 2015, 25, 4567. doi: 10.1016/j.bmcl.2015.08.059
15. [15]
  Lou, D. H.; Wang, G. Q.; Xia, L.; Chen, L.; Wang, Q. A. Chin. J. Org. Chem. 2013, 33, 535 (in Chinese). doi: 10.6023/cjoc201210035
16. [16]
  Zhao, Z. G.; Wang, X. H.; Shi, Z. C.; Cheng, Y. Y. Chin. J. Org. Chem. 2014, 34, 1110 (in Chinese). doi: 10.6023/cjoc201401042
17. [17]
  Xiao, N.; Mei, F.; Sun, Y.; Pan, G. J.; Liu, B. L.; Liu, K. Planta Med. 2014, 80, 993. doi: 10.1055/s-00000058
18. [18]
  Pan, G. J.; Zhao, L. B.; Xiao, N.; Yang, K.; Ma, Y. T.; Zhao, X.; Fan, Z. C.; Zhang, Y. M.; Yao, Q. W.; Lu, K.; Yu, P. Eur. J. Med. Chem. 2016, 122, 674. doi: 10.1016/j.ejmech.2016.07.015
19. [19]
  Weïwer, M.; Chen, C. C.; Kemp, M. M.; Linhardt, R. J. Eur. J. Org. Chem. 2009, 10.1002/ejoc.200900117.
20. [20]
  Hanessian, S.; Saavedra, O. M.; Mascitti, V.; Marterer, W.; Dehriein; R.; Mak, C. P. Tetrahedron 2001, 57, 3267. doi: 10.1016/S0040-4020(01)00196-X
21. [21]
  Tso, K. K.; Leung, K. K.; Liu, H. W.; Lo, K. K. Chem. Commun. 2016, 52, 4557. doi: 10.1039/C6CC00918B
22. [22]
  Michalina, P.; Florence, C. D.; Alain, M.; Stanisław, P. Carbohydr. Res. 2015, 414, 51. doi: 10.1016/j.carres.2015.07.007
23. [23]
  Zhang, S.; Moussodia, R. O.; Sun, H. J.; Leowanawat, P.; Muncan, A.; Nusbaum, C. D.; Chelling, K. M.; Heiney, P. A.; Klein, M. L.; André, S.; Roy, R.; Gabius, H. J.; Percec, V. Angew. Chem., Int. Ed. Engl. 2014, 53, 10899. doi: 10.1002/anie.201403186
1. [1]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
2. [2]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
3. [3]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
4. [4]
  Rong Tian , Yadi Yang , Naihao Lu . Comprehensive Experimental Design of Undergraduate Students Based on Interdisciplinarity: Study on the Effect of Quercetin on Chlorination Activity of Myeloperoxidase. University Chemistry, 2024, 39(8): 247-254. doi: 10.3866/PKU.DXHX202312064
5. [5]
  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
6. [6]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
7. [7]
  Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416
8. [8]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
9. [9]
  Huijuan Liao , Yulin Xiao , Dong Xue , Mingyu Yang , Jianyang Dong . Synthesis of 1-Benzyl Isoquinoline via the Minisci Reaction. University Chemistry, 2025, 40(7): 294-299. doi: 10.12461/PKU.DXHX202409092
10. [10]
  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
11. [11]
  Feiya Cao , Qixin Wang , Pu Li , Zhirong Xing , Ziyu Song , Heng Zhang , Zhibin Zhou , Wenfang Feng . Magnesium-Ion Conducting Electrolyte Based on Grignard Reaction: Synthesis and Properties. University Chemistry, 2024, 39(3): 359-368. doi: 10.3866/PKU.DXHX202308094
12. [12]
  Qilu DU , Li ZHAO , Peng NIE , Bo XU . Synthesis and characterization of osmium-germyl complexes stabilized by triphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1088-1094. doi: 10.11862/CJIC.20240006
13. [13]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
14. [14]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
15. [15]
  Yuxin CHEN , Yanni LING , Yuqing YAO , Keyi WANG , Linna LI , Xin ZHANG , Qin WANG , Hongdao LI , Wenmin WANG . Construction, structures, and interaction with DNA of two Sm^Ⅲ₄ complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1141-1150. doi: 10.11862/CJIC.20240258
16. [16]
  Zhenhua Wang , Haoyang Feng , Xiaoyang Shao , Wenru Fan . Vitamins in Solid Propellants: Controlled Synthesis of Neutral Macromolecular Bonding Agents. University Chemistry, 2025, 40(4): 1-9. doi: 10.3866/PKU.DXHX202401007
17. [17]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
18. [18]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
19. [19]
  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
20. [20]
  Liang TANG , Jingfei NI , Kang XIAO , Xiangmei LIU . Synthesis and X-ray imaging application of lanthanide-organic complex-based scintillators. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1892-1902. doi: 10.11862/CJIC.20240139

Get Citation

PDF

XML

Metrics

PDF Downloads(11)
Abstract views(869)
HTML views(162)

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