Chemistry of Natural Compounds

, Volume 53, Issue 2, pp 248–253 | Cite as

Synthesis and Antioxidant Properties of 5,6,7,8-Tetrahydroxyflavone

  • Linlin Jing
  • Huiping Ma
  • Pengcheng Fan
  • Zhengping Jia
Article
  • 62 Downloads

Flavones are a group of plant secondary metabolites with multiple biological properties. In the present study, 5,6,7,8-tetrahydroxyflavone (5,6,7,8-THF) was synthesized and characterized. In vitro antioxidant study, the effect of 5,6,7,8-THF on total antioxidant activity, reducing power, DPPH radical scavenging, ABTS radical scavenging, superoxide radical scavenging, hydroxyl radical scavenging, nitric oxide radical scavenging, and ferrous chelating activities was examined. According to the results, 5,6,7,8-THF showed excellent free radical scavenging effect and reducing power but weak the ferrous chelating activity. In conclusion, 5,6,7,8-THF can be regarded as an excellent source of antioxidants.

Keywords

flavonoid 5,6,7,8-tetrahydroxyflavone synthesis antioxidant activity chrysin 

Notes

Acknowledgment

Financial support from the National Natural Science Foundation of China (81202458), China Postdoctoral Science Foundation (2012M521926), and Scientific Research Foundation of Gansu Province (1308RJYA061) is gratefully acknowledged.

References

  1. 1.
    M. Singh, M. Kaur, and O. Silakari, Eur. J. Med. Chem., 84, 206 (2014).CrossRefPubMedGoogle Scholar
  2. 2.
    J. Greeff, J. Joubert, S. F. Malan, and S. van Dyk, Bioorg. Med. Chem., 20, 809 (2012).CrossRefPubMedGoogle Scholar
  3. 3.
    O. Firuzi, A. Lacanna, R. Petrucci, G. Marrosu, and L. Saso, Biochim. Biophys. Acta, 1721, 174 (2005).CrossRefPubMedGoogle Scholar
  4. 4.
    Y. H. Chen, Z. S. Yang, C. C. Wen, Y. S. Chang, B. C. Wang, C. A. Hsiao, and T. L. Shih, Food Chem, 134, 717 (2012).CrossRefPubMedGoogle Scholar
  5. 5.
    S. A. van Acker, D. J. van den Berg, M. N. Tromp, D. H. Griffioen, W. P. van Bennekom, W. J. van der Vijgh, and A. Bast, Free Radic. Biol. Med., 20, 331 (1996).CrossRefPubMedGoogle Scholar
  6. 6.
    N. Krafczyk, F. Woyand, and M. A. Glomb, Mol. Nutr. Food Res., 53, 635 (2009).CrossRefPubMedGoogle Scholar
  7. 7.
    A. I. Khlebnikov, I. A. Schepetkin, and M. T. Quinn, Bioorg. Med. Chem., 16, 2791 (2008).CrossRefPubMedPubMedCentralGoogle Scholar
  8. 8.
    A. T. Girgih, R. He, F. M. Hasan, C. C. Udenigwe, T. A. Gill, and R. E. Aluko, Food Chem., 173, 652 (2015).CrossRefPubMedGoogle Scholar
  9. 9.
    J. Taira, E. Tsuchida, M. C. Katoh, M. Uehara, and T. Ogi, Food Chem., 166, 531 (2015).CrossRefPubMedGoogle Scholar
  10. 10.
    A. M. Abbasi, M. H. Shah, T. Li, X. Fu, X. Guo, and R. H. Liu, J. Ethnopharmacol., 162, 333 (2015).CrossRefPubMedGoogle Scholar
  11. 11.
    P. Prieto, M. Pineda, and M. Aguilar, Anal. Biochem., 269, 337 (1999).CrossRefPubMedGoogle Scholar
  12. 12.
    H. Park, T. T. Dao, and H. P. Kim, Eur. J. Med. Chem., 40, 943 (2005).CrossRefPubMedGoogle Scholar
  13. 13.
    P. Bovicelli, V. D′Angelo, D. Collalto, A. Verzina, N. D′Antona, and D. Lambusta, J. Pharm. Pharmacol., 59, 1697 (2007).CrossRefPubMedGoogle Scholar
  14. 14.
    J. F. W. McOmie, M. L. Watts, and D. E. West, Tetrahedron, 24, 2289 (1968).CrossRefGoogle Scholar
  15. 15.
    J. A. Vaz, L. Barros, A. Martins, C. Santos-Buelga, M. H. Vasconcelos, and I. C. F. R. Ferreira, Food Chem., 126, 610 (2011).CrossRefGoogle Scholar
  16. 16.
    R. Re, N. Pellegrini, A. Proteggente, A. Pannala, M. Yang, and C. Rice-Evans, Free Radic. Biol. Med., 26, 1231 (1999).CrossRefPubMedGoogle Scholar
  17. 17.
    J. Liu, L. Jia, J. Kan, and C. H. Jin, Food Chem. Toxicol., 51, 310 (2013).CrossRefPubMedGoogle Scholar
  18. 18.
    R. A. Khan, M. R. Khan, S. Sahreen, and M. Ahmed, Chem. Cent. J., 6, 12 (2012).PubMedPubMedCentralGoogle Scholar
  19. 19.
    B. Sangameswaran, B. R. Balakrishnan, C. Deshraj, and B. Jayakar, Pak. J. Pharm. Sci., 22, 368 (2009).PubMedGoogle Scholar
  20. 20.
    J. He, B. Huang, X. Ban, J. Tian, L. Zhu, and Y. Wang, J. Ethnopharmacol., 141, 104 (2012).CrossRefPubMedGoogle Scholar
  21. 21.
    M. Oyaizu, Jpn. J. Nutr., 44, 307 (1986).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2017

Authors and Affiliations

  • Linlin Jing
    • 1
  • Huiping Ma
    • 1
  • Pengcheng Fan
    • 1
  • Zhengping Jia
    • 1
  1. 1.Department of Pharmacy, Lanzhou General HospitalLanzhou Command of CPLALanzhouP. R. China

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