Citation: Ma Jimei, Xie Lingyun, Wang Longwen, Chen Hangwei, Zeng Zhen, Chen Hao, Jiang Hong. Synthesis and α-Glycosidase Inhibitory Activity of Three Ascorbic Acid Glycosides[J]. Chinese Journal of Organic Chemistry, ;2017, 37(6): 1426-1432. doi: 10.6023/cjoc201612037 shu

Synthesis and α-Glycosidase Inhibitory Activity of Three Ascorbic Acid Glycosides

  • Corresponding author: Ma Jimei, majimei@mail.hzau.edu.cn Jiang Hong, jianghong@mail.hzau.edu.cn
  • Received Date: 11 December 2016
    Revised Date: 20 January 2017

    Fund Project: the National Natural Science Foundation of China 21402056the Fundamental Research Funds for the Central Universities 2014QC007

Figures(5)

  • 2-O-(β-D-Glucopyranosyl)-L-ascorbic acid, a natural β-glycoside with ascorbic acid moiety present in Lycium barbarum, and its two analogues were chemically synthesized. Their inhibitory effect on yeast α-glucosidase and α-amylase were investigated with commercially available acarbose as positive control. The biological assays demonstrated the distinct inhibitory effect of these compounds on α-glucosidase activity and weak inhibitory activity against pancreatic α-amylase. The kinetic study indicated that these compounds were competitive inhibitors. These results imply that these three β-glycosides have the potential to be developed as α-glucosidase inhibitors.
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    1. [1]

      (a) Zhu, J.; Liu, W.; Yu, J.; Zou, S.; Wang, J.; Yao, W.; Gao, X. Carbohydr. Polym. 2013, 98, 8.
      (b) Zhou, Z.; Yan, J.; Tang, X.; Zhang, W.; Zhang, Y.; Chen, X.; Su, X.; Yang, D. Chin. J. Org. Chem. 2010, 30, 582 (in Chinese).
      (周祖文, 晏菊芳, 唐雪梅, 张蔚瑜, 张映霞, 陈欣, 苏小燕, 杨大成, 有机化学, 2010, 30, 582.)

    2. [2]

      Ruan, C.-T.; Lam, S.-H.; Lee, S.-S.; Su, M.-J. Phytomedicine 2013, 20, 667.  doi: 10.1016/j.phymed.2013.02.009

    3. [3]

      (a) Aoki, K.; Muraoka, T.; Ito, Y.; Togashi, Y.; Terauchi, Y. Intern. Med. 2010, 49, 1085.
      (b) Derosa, G.; Maffioli, P. Clin. Ther. 2012, 34, 1221.
      (c) Hollander, P. Drugs 2012, 44, 47.

    4. [4]

      (a) Escandon-Rivera, S.; Gonzalez-Andrade, M.; Bye, R.; Linares, E.; Navarrete, A.; Mata, R. J. Nat. Prod. 2012, 75, 968.
      (b) Huang, Y.; Fu, W.; Li, Y.; Liu, Yu.; Li, Z.; Liu, Y.; Liu, S.; Sun, J.; Li, N.; Wang, B.; Gao, X.; Zhang, D. J. Evidence-Based Complementary Altern. 2014, 2014, 9.
      (c) Kim, Y.-M.; Wang, M.-H.; Rhee, H.-I. Carbohydr. Res. 2004, 339, 715.
      (d) Alarcon-Aguilara, F. J.; Roman-Ramos, R.; Perez-Gutierrez, S.; Aguilar-Contreras, A.; Contreras-Weber, C. C.; Flores-Saenz, J. L. J. Ethnopharmacol. 1998, 61, 101.

    5. [5]

      (a) Cheng, J.; Zhou, Z.-W.; Sheng, H.-P.; He, L.-J.; Fan, X.-W.; He, Z.-X.; Sun, T.; Zhang, X.; Zhao, R. J.; Gu, L.; Cao, C.; Zhou, S.-F. Drug Des., Dev. Ther. 2015, 9, 33.
      (b) Cai, H.; Liu, F.; Zuo, P.; Huang, G.; Song, Z.; Wang, T.; Lu, H.; Guo, F.; Han, C.; Sun, G. Med. Chem. 2015, 11, 383.

    6. [6]

      Toyoda-Ono, Y.; Maeda, M.; Nakao, M.; Yoshimura, M.; Sugiura-Tomimori, N.; Fukami, H. J. Agric. Food Chem. 2004, 52, 2092.  doi: 10.1021/jf035445w

    7. [7]

      (a) Takebayashi, J.; Yagi, Y.; Ishii, R.; Abe, S.; Yamada, K.; Tai, A. Biosci. Biotechnol. Biochem. 2008, 72, 1558.
      (b) Zhang, Z.; Liu, X.; Zhang, X.; Liu, J.; Hao, Y.; Yang, X.; Wang, Y. Arch. Pharm. Res. 2011, 34, 801.
      (c) Zhang, Z.; Zhang, L.; Hao, Y. J. Practic. Med. 2011, 27, 11 (in Chinese).
      (张自萍, 张立平, 郝艳芳, 实用医学杂志, 2011, 27, 11.)
      (d) Li, H.; Zhang, Z.; Liao, G. Chin. J. New Drug 2007, 16, 212 (in Chinese).
      (李弘武, 张自萍, 廖国玲, 中国新药杂志, 2007, 16, 212.)
      (e) Xie, R.; Zhang, Z.; Qiu, J. Bull. Sci. Technol. 2010, 26, 362 (in Chinese).
      (谢若男, 张正波, 裘娟萍, 科技通报, 2010, 26, 362.)

    8. [8]

      Zhang, Z.; Liu, X.; Wu, T.; Liu, J.; Zhang, X.; Yang, X.; Goodheart, M. J.; Engelhardt, J. F.; Wang, Y. Cell Biol. Toxicol. 2011, 27, 107.  doi: 10.1007/s10565-010-9174-2

    9. [9]

      (a) Olabisi, A. O.; Wimalasena, K. J. Org. Chem. 2004, 69, 7026.
      (b) Zheng, H. Pharmaceutical Chemistry, People's Medical Publishing House, Bejing, 2007, p. 426 (in Chinese).
      (郑虎, 药物化学, 人民卫生出版社, 北京, 2007, p. 426.)

    10. [10]

      Cho, B.-H.; Kim, J.-H.; Jeon, H.-B.; Kim, K.-W. Tetrahedron 2005, 61, 4341.  doi: 10.1016/j.tet.2005.03.001

    11. [11]

      Kim, G.-N.; Kwon, Y.-I.; Jang, H.-D. J. Med. Food 2011, 14, 712.  doi: 10.1089/jmf.2010.1368

    12. [12]

      (a) Balan, K.; Perumal, P.; Sundar abaalaji, N.; Palvannan, T. J. Mol. Struct. 2015, 1081, 62.
      (b) Sheng, Z.; Dai, H.; Pan, S.; Wang, H.; Hu, Y.; Ma, W. Molecules 2014, 19, 10563.

    13. [13]

      Brindis, F.; Rodríguez, R.; Bye, R.; Gonzalez-Andrade, M.; Mata, R. J. Nat. Prod. 2011, 74, 314.  doi: 10.1021/np100447a

    14. [14]

      Thongprajukaew, K.; Choodum, A.; Sa-E, B.; Hayee, U. Food Chem. 2014, 163, 87.  doi: 10.1016/j.foodchem.2014.04.080

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