Skip to main content
SpringerLink
Log in

Antioxidant activity of 2H-chromen-2-one derivatives

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Moderate antiradical activity of 2H-chromen-2-one derivatives was established in a set of assays. The highest activity towards the superoxide radical anion (O •–2 ) generated in the model of enzymatic reduction of nitro blue tetrazolium was found for 4-[(1,2,3,4-tetra-hydro-1-oxonaphthalen-2-yl)(piperidin-1-yl)methyl]benzoic acid. In the non-enzymatic oxidation of epinephrine in an alkaline medium, like in other model systems, the highest activity was found for 4-(6-oxo-8,9-dihydro-6H,7H-benzo[h]-chromene[4,3-b]chromen-7-yl)benzoic acid. The absence of pronounced Fe2+-chelating activity and low reducing activity were revealed for 2H-chromen-2-one derivatives. In the model of long-lasting lipid peroxidation of tilapia liver, prolonged antioxidant effect was established for all of the test derivatives.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

References

  1. K. V. Sashidhara, A. Kumar, M. Kumar, J. Sarkar, S. Sinha, Bioorg. Med. Chem. Lett., 2010, 20, 7205; DOI: https://doi.org/10.1016/j.bmcl.2010.10.116.

    Article  CAS  PubMed  Google Scholar 

  2. E. V. Buravlev, I. V. Fedorova, O. G. Shevchenko, A. V. Kutchin, Russ. Chem. Bull., 2019, 68, 1558; DOI: https://doi.org/10.1007/s11172-019-2592-2.

    Article  CAS  Google Scholar 

  3. S. N. Mokale, A. Begum, N. S. Sakle, V. R. Shelke, S. A. Bhavale, Biomed. Pharmacother., 2017, 89, 966; DOI: https://doi.org/10.1016/j.biopha.2017.02.089.

    Article  CAS  PubMed  Google Scholar 

  4. Z. Sang, K. Wang, H. Wang, H. Wang, Q. Ma, X. Han, M. Ye, L. Yu, W. Liu, Bioorg. Med. Chem. Lett., 2017, 27, 5046; DOI: https://doi.org/10.1016/j.bmcl.2017.09.057.

    Article  CAS  PubMed  Google Scholar 

  5. D. Egan, R. O’Kennedy, E. Moran, D. Cox, E. Prosser, R. D. Thornes, Drug Metab. Rev., 1990, 22, 503; DOI: https://doi.org/10.3109/03602539008991449.

    Article  CAS  PubMed  Google Scholar 

  6. J. Zhang, W. Xue, P. Wang, T. Wang, Y. Liang, Z. Zhang, Tetrahedron, 2018, 74, 4712; DOI: https://doi.org/10.1016/j.tet.2018.07.018.

    Article  CAS  Google Scholar 

  7. M. R. Jadhav, D. B. Shinde, Chin. J. Chem., 2010, 28, 555; DOI: https://doi.org/10.1002/cjoc.201090111.

    Article  CAS  Google Scholar 

  8. G. B. Bubols, D. R. Vianna, A. Medina-Remón, G. Poser, R. M. Lamuela-Raventos, V. L. Eifler-Lima, S. C. Garcia, Mini-Rev. Med. Chem., 2013, 13, 318; DOI: https://doi.org/10.2174/138955713804999775.

    CAS  PubMed  Google Scholar 

  9. T. Kundu, A. Pramanik, Bioorg. Chem., 2020, 98, 103734; DOI: https://doi.org/10.1016/j.bioorg.2020.103734.

    Article  CAS  PubMed  Google Scholar 

  10. A. Yu. Potapov, B. V. Paponov, N. A. Podoplelova, M. A. Panteleev, V. A. Polikarchuk, I. V. Ledenyova, N. V. Stolpovskaya, D. V. Kryl’skii, Kh. S. Shikhaliev, Russ. Chem. Bull., 2021, 70, 492; DOI: https://doi.org/10.1007/s11172-021-3114-6.

    Article  CAS  Google Scholar 

  11. X. Li, T. Wang, J. Liu, Y. Liu, J. Zhang, J. Lin, Zh. Zhao, D. Chen, Arab. J. Chem., 2020, 13, 184; DOI: https://doi.org/10.1016/j.arabjc.2017.03.008.

    Article  CAS  Google Scholar 

  12. S.-H. Lim, T.-Y. Ha, J. Ahn, S. Kim, Phytomed. Int. J. Phytother. Phytopharmacol., 2011, 18, 425; DOI: https://doi.org/10.1016/j.phymed.2011.02.002.

    CAS  Google Scholar 

  13. Z. Liang, Y. Chen, Z. Wang, X. Wu, C. Deng, C. Wang, W. Yang, Y. Tian, S. Zhang, C. Lu, Y. Yang, J. Adv. Res., 2022, 40, 249; DOI: https://doi.org/10.1016/j.jare.2021.12.007.

    Article  CAS  PubMed  Google Scholar 

  14. A. Khan, S. Khan, H. Ali, K. U. Shah, H. Ali, O. Shehzad, A. Onder, Y. S. Kim, Int. Immunopharmacol., 2019, 73, 451; DOI: https://doi.org/10.1016/j.intimp.2019.05.032.

    Article  CAS  PubMed  Google Scholar 

  15. S. Khan, R. J. Choi, J. Lee, Y. S. Kim, Eur. J. Pharmacol., 2016, 774, 95; DOI: https://doi.org/10.1016/j.ejphar.2016.02.008.

    Article  CAS  PubMed  Google Scholar 

  16. V. Pawar, L. A. Shastri, P. Gudimani, S. Joshi, V. M. Kumbar, V. Sunagar, J. Mol. Struct., 2022, 1254, 132300; DOI: https://doi.org/10.1016/j.molstruc.2021.132300.

    Article  CAS  Google Scholar 

  17. J. R. Mays, S. A. Hill, J. T. Moyers, B. S.J. Blagg, Bioorg. Med. Chem., 2010, 18, 249; DOI: https://doi.org/10.1016/j.bmc.2009.10.061.

    Article  CAS  PubMed  Google Scholar 

  18. K. V. Sashidhara, J. N. Rosaiah, M. Kumar, R. K. Gara, L. V. Nayak, K. Srivastava, H. K. Bid, R. Konwar, Bioorg. Med. Chem. Lett., 2010, 20, 7127; DOI: https://doi.org/10.1016/j.bmcl.2010.09.040.

    Article  CAS  PubMed  Google Scholar 

  19. R. Shylaja, C. Loganathan, S. Kabilan, T. Vijayakumar, C. Meganathan, J. Mol. Struct., 2021, 1224, 129289; DOI: https://doi.org/10.1016/j.molstruc.2020.129289.

    Article  CAS  Google Scholar 

  20. A. L. Ivanova, I. V. Kanevskaya, O. V. Fedotova, Russ. J. Org. Chem., 2019, 55, 1231; DOI: https://doi.org/10.1134/S1070428019080244.

    Article  CAS  Google Scholar 

  21. I. V. Kanevskaya, A. L. Ivanova, N. V. Pchelintseva, O. V. Fedotova, Izv. Sarat. un-ta. Nov. ser. Ser. Khimiya. Biologiya. Ekologiya [Bull. Sarat. Univ. New Series. Ser. Chemistry. Biology. Ecology], 2022, 22, 128; DOI: https://doi.org/10.18500/1816-9775-2022-22-2-128-132 (in Russian).

    Google Scholar 

  22. K. Sridhar, A. L. Charles, Food Chem., 2019, 275, 41; DOI: https://doi.org/10.1016/j.foodchem.2018.09.040.

    Article  CAS  PubMed  Google Scholar 

  23. R. Apak, K. Guclu, M. Ozyurek, S. E. Karademir, J. Agric. Food Chem., 2004, 52, 7970; DOI: https://doi.org/10.1021/jf048741x.

    Article  CAS  PubMed  Google Scholar 

  24. N. B. Sadeer, D. Montesano, S. Albrizio, G. Zengin, M. F. Mahomoodally, Antioxidants, 2020, 9, 709; DOI: https://doi.org/10.3390/antiox9080709.

    Article  CAS  Google Scholar 

  25. T. C. Dinis, V. M. Madeira, L. M. Almeida, Arch. Biochem. Biophys., 1994, 315, 161; DOI: https://doi.org/10.1006/abbi.1994.1485.

    Article  CAS  PubMed  Google Scholar 

  26. T. V. Sirota, Biochem. Moscow Suppl. Ser. B, 2014, 8, 323; DOI: https://doi.org/10.1134/S1990750814040088.

    Article  Google Scholar 

  27. E. N. Stroev, V. G. Makarova, Praktikum po Biologicheskoi Khimii [Laboratory Works in Biological Chemistry], Vysshaya shkola, Moscow, 1986, 279 pp. (in Russian).

    Google Scholar 

  28. A. Beillerot, J. C. Rodríguez Domínguez, G. Kirsch, D. Bagrel, Bioorg. Med. Chem. Lett., 2008, 18, 1102; DOI: https://doi.org/10.1016/j.bmcl.2007.12.004.

    Article  CAS  PubMed  Google Scholar 

  29. M. C. Foti, J. Agric. Food Chem., 2015, 63, 8765; DOI: https://doi.org/10.1021/acs.jafc.5b03839.

    Article  CAS  PubMed  Google Scholar 

  30. M. C. Foti, C. Daquino, I. D. Mackie, G. A. DiLabio, K. U. Ingold, J. Org. Chem., 2008, 73, 9270; DOI: https://doi.org/10.1021/jo8016555.

    Article  CAS  PubMed  Google Scholar 

  31. M. Salamone, R. Martella, M. Bietti, J. Org. Chem., 2012, 77, 8556; DOI: https://doi.org/10.1021/jo3015352.

    Article  CAS  PubMed  Google Scholar 

  32. J. Xie, K. M. Schaich, J. Agric. Food Chem., 2014, 62, 4251; DOI: https://doi.org/10.1021/jf500180u.

    Article  CAS  PubMed  Google Scholar 

  33. V. P. Osipova, M. A. Polovinkina, M. N. Kolyada, A. D. Osipova, N. T. Berberova, A. V. Velikorodov, Dokl. Chem., 2021, 500, 188; DOI: https://doi.org/10.1134/S0012500821090020.

    Article  CAS  Google Scholar 

  34. P. Pathak, J. Novak, V. Naumovich, M. Grishina, A. Balkrishna, N. Sharma, V. Sharma, V. Potemkin, A. Verma, Biocatal. Agric. Biotechnol., 2020, 29, 101804; DOI: https://doi.org/10.1016/j.bcab.2020.101804.

    Article  Google Scholar 

  35. P. Mladěnka, K. Macáková, L. Zatloukalová, Z. Řeháková, B. K. Singh, A. K. Prasad, V. S. Parmar, L. Jahodář, R. Hrdina, L. Saso, Biochimie, 2010, 92, 1108; DOI: https://doi.org/10.1016/j.biochi.2010.03.025.

    Article  PubMed  Google Scholar 

  36. M. A. Polovinkina, A. D. Osipova, V. P. Osipova, N. T. Berberova, D. B. Shpakovsky, Yu. A. Gracheva, E. R. Milaeva, Russ. Chem. Bull., 2022, 71, 2218.

    Article  CAS  Google Scholar 

  37. I. V. Tikhonov, L. I. Borodin, V. D. Sen, E. M. Pliss, Russ. Chem. Bull., 2020, 69, 2097; DOI: https://doi.org/10.1007/s11172-020-3005-2.

    Article  CAS  Google Scholar 

  38. N. B. Melnikova, O. N. Solovyeva, V. M. Muzykina, V. P. Gubskaya, G. M. Fazleeva, A. I. Poddelsky, Russ. Chem. Bull., 2019, 68, 149; DOI: https://doi.org/10.1007/s11172-019-2430-6.

    Article  CAS  Google Scholar 

  39. M. N. Kolyada, V. P. Osipova, M. A. Polovinkina, L. T. Telekova, A. D. Osipova, A. V. Velikorodov, N. T. Berberova, Yu. T. Pimenov, AIP Conference Proceedings, 2022, 2390, 020035–1; DOI: https://doi.org/10.1063/5.0069224.

    Article  CAS  Google Scholar 

  40. M. B. Yim, P. B. Chock, E. R. Stadtman, Proc. Natl. Acad. Sci. USA, 1990, 87, 5006; DOI: https://doi.org/10.1073/pnas.87.13.5006.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  41. V. P. Osipova, M. A. Polovinkina, L. R. Telekova, A. V. Velikorodov, N. N. Stepkina, N. T. Berberova, Russ. Chem. Bull., 2020, 69, 504; DOI: https://doi.org/10.1007/s11172-020-2790-y.

    Article  CAS  Google Scholar 

  42. I. M. Chernushkina, N. A. Antonova, N. O. Movchan, V. P. Osipova, M. N. Kolyada, Yu. T. Pimenov, Izv. Samar.

Download references

Author information

Authors and Affiliations

  1. Federal Research Center, Southern Scientific Center of the Russian Academy of Sciences, 41 prosp. Chekhova, 344006, Rostov-on-Don, Russian Federation

    M. A. Polovinkina & V. P. Osipova

  2. Astrakhan State Technical University, 16 ul. Tatishcheva, 414056, Astrakhan, Russian Federation

    A. D. Osipova & N. T. Berberova

  3. N. G. Chernyshevsky National Research Saratov State University, 83 ul. Astrakhanskaya, 410012, Saratov, Russian Federation

    I. V. Kanevskaya, A. L. Ivanova & N. V. Pchelintseva

Authors
  1. M. A. Polovinkina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. P. Osipova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. D. Osipova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. I. V. Kanevskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. L. Ivanova
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. N. V. Pchelintseva
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. N. T. Berberova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. P. Osipova.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2645–2653, December, 2022.

This study was financially supported by the Russian Foundation for Basic Research (Project No. 20-03-00446) and within the framework of the state assignment (registration No. 122020100328-1, in vitro experiments with tilapia liver).

No human or animal subjects were used in this research.

The authors declare no competing interests.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Polovinkina, M.A., Osipova, V.P., Osipova, A.D. et al. Antioxidant activity of 2H-chromen-2-one derivatives. Russ Chem Bull 71, 2645–2653 (2022). https://doi.org/10.1007/s11172-022-3694-9

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-022-3694-9

Key words

Search

Navigation