SpringerLink
Log in

Is curcumin an active suicidal antioxidant only in the aqueous environments?

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

Curcumin is a natural polyphenol with various bioactivities, including anti-tumor, antioxidant, and anti-inflammatory. Despite curcumin’s therapeutic benefits, limited water solubility and rapid hydrolytic degradation are important challenges in using of curcumin for clinical applications. Therefore, this report aimed to examine the stability and antioxidant activity of curcumin in different environments and to find out the mechanism of action through which curcumin shows its radical scavenging activity. Results of this study not only indicated that degradation of curcumin is water-dependent but also suggested its degradation mechanism is distinct from general acid/base catalysis and nucleophilic attack of water hydroxyl ion (OH−) had apparently negligible role in rapid hydrolytic degradation of curcumin. We confirmed that curcumin is solely responsible for its antioxidant activity in aqueous media and its degradation is a spontaneous autoxidation. More importantly, curcumin exhibited rapid decomposition in the presence of excessive O2 or free radicals induced by oxidizing agents (TBHP and H2O2) due to its protective potential against oxidative stress. The possible attack site of free radicals in curcumin is in the first step of curcumin degradation, where phenoxyl radical is produced. On the other hand, curcumin degradation and scavenging activity reduced when it entered into the hydrophobic cavity of BSA or casein molecule. Surprisingly, in soybean oil, curcumin showed the weak antioxidant activity compared to TBHQ (as a potent synthetic antioxidant for frying oils), implying that curcumin did not have significant antioxidant potential in oily/hydrophobic environments. Overall, our findings confirmed that curcumin in aqueous buffer is quickly degrades while at the same time scavenging of free radicals. The presented results are novel and might be interesting as the analysis of physicochemistry of curcumin has been gaining importance in view of biological significance.

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13

Similar content being viewed by others

References

  1. M.M. Nadi, M.R. Ashrafi Kooshk, K. Mansouri, S.A. Ghadami, M. Amani, S. Ghobadi, R. Khodarahmi, Int. J. Food Prop. 18, 638–659 (2015)

    Article  CAS  Google Scholar 

  2. C.-H. Hsu, A.-L. Cheng, The Molecular Targets and Therapeutic Uses of Curcumin in Health and Disease (Springer, Berlin, 2007), pp. 471–480

    Book  Google Scholar 

  3. M. Mehrabi, S. Esmaeili, M. Ezati, M. Abassi, H. Rasouli, D. Nazari, H. Adibi, R. Khodarahmi, Bioorg. Chem. 110, 104720 (2021)

    Article  CAS  Google Scholar 

  4. R. Sharma, A. Gescher, W. Steward, Eur. J. Cancer. 41, 1955–1968 (2005)

    Article  CAS  Google Scholar 

  5. C.F. Chignell, P. Bilskj, K.J. Reszka, A.G. Motten, R.H. Sik, T.A. Dahl, Photochem. Photobiol. 59, 295–302 (1994)

    Article  CAS  Google Scholar 

  6. T. Ak, İ Gülçin, Chem. Biol. Interact. 174, 27–37 (2008)

    Article  CAS  Google Scholar 

  7. O.N. Gordon, P.B. Luis, H.O. Sintim, C. Schneider, J. Biol. Chem. 290, 4817–4828 (2015)

    Article  CAS  Google Scholar 

  8. M. Griesser, V. Pistis, T. Suzuki, N. Tejera, D.A. Pratt, C. Schneider, J. Biol. Chem. 286, 1114–1124 (2011)

    Article  CAS  Google Scholar 

  9. A. Kumar, A. Ahuja, J. Ali, S. Baboota, Crit. Rev. Ther. Drug Carrier Syst. 27, 279–312 (2010)

  10. Y.-J. Wang, M.-H. Pan, A.-L. Cheng, L.-I. Lin, Y.-S. Ho, C.-Y. Hsieh, J.-K. Lin, J. Pharm. Biomed. Anal. 15, 1867–1876 (1997)

    Article  CAS  Google Scholar 

  11. C. Schneider, O.N. Gordon, R.L. Edwards, P.B. Luis, J. Agric. Food Chem. 63, 7606–7614 (2015)

    Article  CAS  Google Scholar 

  12. O.N. Gordon, C. Schneider, Trends Mol. Med. 18, 361–363 (2012)

    Article  CAS  Google Scholar 

  13. J. Zhu, K.Z. Sanidad, E. Sukamtoh, G. Zhang, Food Funct. 8, 907–914 (2017)

    Article  CAS  Google Scholar 

  14. L. Shen, C.-C. Liu, C.-Y. An, H.-F. Ji, Sci. Rep. 6, 1–10 (2016)

    Article  CAS  Google Scholar 

  15. J. Jankun, M. Wyganowska-Świątkowska, K. Dettlaff, A. Jelińska, A. Surdacka, D. Wątróbska-Świetlikowska, E. Skrzypczak-Jankun, Int. J. Mol. Med. 37, 1151–1158 (2016)

    Article  CAS  Google Scholar 

  16. A. Hunyadi, Med. Res. Rev. 39, 2505–2533 (2019)

    Article  CAS  Google Scholar 

  17. C. Evans, G. List, H.A. Moser, J.J. Cowan, J. Am. Oil Chem. Soc. 50, 218–222 (1973)

    Article  CAS  Google Scholar 

  18. L. Brühl, Wiley Online Library (AOCS Press, Champaign, 1997)

    Google Scholar 

  19. M.S. Blois, Nature 181, 1199–1200 (1958)

    Article  CAS  Google Scholar 

  20. M. Burits, F. Bucar, Phytother. Res. 14, 323–328 (2000)

    Article  CAS  Google Scholar 

  21. I. Gülçin, Amino Acids 32, 431–438 (2007)

    Article  Google Scholar 

  22. J. Ancerewicz, E. Migliavacca, P.-A. Carrupt, B. Testa, F. Brée, R. Zini, J.-P. Tillement, S. Labidalle, D. Guyot, A.-M. Chauvet-Monges, Free Radic. Biol. Med. 25, 113–120 (1998)

    Article  CAS  Google Scholar 

  23. Y. Nimiya, W. Wang, Z. Du, E. Sukamtoh, J. Zhu, E. Decker, G. Zhang, Mol. Nutr. Food Res. 60, 487–494 (2016)

    Article  CAS  Google Scholar 

  24. D. Voet, J.G. Voet, Biochemistry (Wiley, New York, 1995), pp. 506–516

  25. H. Sies, C. Berndt, D.P. Jones, Annu. Rev. Biochem. 86, 715–748 (2017)

    Article  CAS  Google Scholar 

  26. T. Kar, P. Basak, S. Sen, R.K. Ghosh, M. Bhattacharyya, Front. Biol. 12, 199–209 (2017)

    Article  CAS  Google Scholar 

  27. F. Zsila, Z. Bikádi, M.J.B. Simonyi, Biochem. Biophys. Res. Commun. 301, 776–782 (2003)

    Article  CAS  Google Scholar 

  28. B. Pastrello, G.C. dos Santos, L.C. da Silva-Filho, A.R. de Souza, N.H. Morgon, V.F. **menes, Dyes Pigm. 173, 107874 (2020)

    Article  CAS  Google Scholar 

  29. O.A. Kucherak, L. Richert, Y. Mély, A.S. Klymchenko, Phys. Chem. Chem. Phys. 14, 2292–2300 (2012)

    Article  CAS  Google Scholar 

  30. S. Ercelen, A.S. Klymchenko, A.P. Demchenko, FEBS Lett. 538, 25–28 (2003)

    Article  CAS  Google Scholar 

  31. M. Yang, Y. Wu, J. Li, H. Zhou, X.J. Wang, Agric. Food Chem. 61, 7150–7155 (2013)

    Article  CAS  Google Scholar 

  32. F. Mirzaee, L. Hosseinzadeh, M.R. Ashrafi-Kooshk, S. Esmaeili, S. Ghobadi, M.H. Farzaei, M.R. Zad-Bari, R. Khodarahmi, Protein Pept. Lett. 26, 132–147 (2019)

    Article  CAS  Google Scholar 

  33. M.A.D. Guillén, N. Cabo, Food Chem. 77, 503–510 (2002)

    Article  Google Scholar 

  34. A.H. Sneharani, S.A. Singh, A.J. Appu Rao, J. Agric. Food Chem. 57, 10386–10391 (2009)

    Article  CAS  Google Scholar 

  35. P. Bharmoria, M. Bisht, M.C. Gomes, M. Martins, M.C. Neves, J.F. Mano, I. Bdikin, J.A. Coutinho, S.P. Ventura, Sci. Rep. 11, 1–12 (2021)

    Article  Google Scholar 

  36. S. Rege, M. Arya, S. Momin, Ukr. J. Food Sci. 7, 27–32 (2019)

  37. S.A. Rege, M.A. Varshneya, S.A.J.C. Momin, J. Food Sci. Technol. 13, 128–132 (2021)

    Google Scholar 

Download references

Acknowledgements

The authors gratefully acknowledge the Student Research committee, Kermanshah University of Medical sciences (KUMS), Kermanshah, Iran, for the financial supports (Grant no. 50001082).

Author information

Authors and Affiliations

  1. Medical Biology Research Center, Health Technology Institute, Kermanshah University of Medical Sciences (KUMS), Kermanshah, Iran

    Masomeh Mehrabi, Farahnaz Karami, Maryam Siah, Sajjad Esmaeili & Reza Khodarahmi

  2. Student Research Committee, Kermanshah University of Medical Sciences (KUMS), Kermanshah, Iran

    Maryam Siah

  3. Department of Pharmacognosy and Biotechnology, Faculty of Pharmacy, Kermanshah University of Medical Sciences (KUMS), Kermanshah, Iran

    Reza Khodarahmi

Authors
  1. Masomeh Mehrabi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Farahnaz Karami
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Maryam Siah
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Sajjad Esmaeili
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Reza Khodarahmi
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

RK designed the study. MS, FK and SE performed experiments/assays under supervision of RK and MM All authors, especially, MM and RK contributed to the writing and editing of the manuscript.

Corresponding authors

Correspondence to Farahnaz Karami or Reza Khodarahmi.

Ethics declarations

Conflict of interest

The authors declare that they have no financial interests or personal relationships that could have appeared to influence the work reported in the present study.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mehrabi, M., Karami, F., Siah, M. et al. Is curcumin an active suicidal antioxidant only in the aqueous environments?. J IRAN CHEM SOC 19, 3441–3450 (2022). https://doi.org/10.1007/s13738-022-02538-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-022-02538-3

Keywords

Search

Navigation