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Products of the Intermediate Oxidation of Flavonoids in Aqueous Solutions and the Determination of Their Composition by High-Performance Liquid Chromatography–Mass Spectrometry

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Abstract

Using high-performance liquid chromatography in combination with electrospray ionization mass spectrometry [HPLC–MS-ESI(NEG)], quercetin [Q] and luteolin [L] intermediate oxidation products were investigated. It was found that, in aqueous solutions at pH 8.0 under aerobic conditions, quercetin forms double and triple donor-acceptor complexes of the composition {[Q][Q–H2]} and {[Q][Q–H2]2}, which can be separated by HPLC, but are rapidly converted to deeper oxidation products. In the presence of another flavonoid, luteolin (L), the oxidized form of quercetin also forms mixed complexes of {[L][Q–H2]} and {[L][Q–H2]2} types. Luteolin in the oxidation does not form donor-acceptor {[L][L–H2]} complexes. Quercetin in complexes with luteolin is always present in an oxidized form. It can be assumed that these complexes form as a result of the recombination of two radicals of flavonoids, which formed initially as a result of manifestation of the antioxidant properties (one-electron transfer). These transformations of flavonoids are possible if strict anaerobic conditions in their quantitative determination are not implemented.

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REFERENCES

  1. Willcox, J.K., Ash, S.L., and Catignani, G.L., Crit. Rev. Food Sci. Nutr., 2004, vol. 44, no. 4, p. 275.

    Article  CAS  PubMed  Google Scholar 

  2. Jacobs, H., Moalin, M., Bast, A., Van der Vijgh, W., and Haenen, G., PLoS One, 2010, vol. 5, no. 11, p. 437.

    Article  CAS  Google Scholar 

  3. Vukics, V., Hevesi, B., Ringer, T., Ludanyi, K., Kery, A., Bonn, G.K., and Guttman, A., J. Chromatogr. Sci., 2008, vol. 46, no. 2, p. 97.

    Article  CAS  PubMed  Google Scholar 

  4. Pourcel, L., Routaboul, J.M., Cheynier, V., Lepiniec, L., and Debeaujon, I., Trends Plant Sci., 2007, vol. 12, no. 1, p. 29.

    Article  CAS  PubMed  Google Scholar 

  5. Galati, G., Moridani, M.Y., Chan, T.S., and O’Brien, P.J., Free Radical Biol. Med., 2001, vol. 30, no. 4, p. 370.

    Article  CAS  Google Scholar 

  6. Boersma, M.G., Vervoort, J., Szymusiak, H., Lemanska, K., Tyrakowska, B., Cenas, N., Segura-Aguilar, J., and Rietjens, I.M., Chem. Res. Toxicol., 2000, vol. 13, no. 3, p. 185.

    Article  CAS  PubMed  Google Scholar 

  7. Awad, H.M., Boersma, M.G., Boeren, S., van Bladeren, P.J., Vervoort, J., and Rietjens, I.M., Chem. Res. Toxicol., 2001, vol. 14, no. 4, p. 398.

    Article  CAS  PubMed  Google Scholar 

  8. Awad, H.M., Boersma, M.G., Boeren, S., Van der Woude, H., Van Zanden, J., Van Bladeren, P.J., Vervoort, J., and Rietjens, I.M., FEBS Lett., 2002, vol. 520, nos 1–3, p. 30.

  9. Vervoort, J. and Rietjens, I.M., Chem. Res. Toxicol., 2002, vol. 15, no. 3, p. 343.

    Article  CAS  PubMed  Google Scholar 

  10. Awad, H.M., Boersma, M.G., Boeren, S., Van Bladeren, P.J., Vervoort, J., and Rietjens, I.M., Chem. Res. Toxicol., 2003, vol. 16, no. 7, p. 822.

    Article  CAS  PubMed  Google Scholar 

  11. Krishnamachari, W., Levine, L.H., and Pare, P.W., J. Agric. Food Chem., 2002, vol. 50, no. 15, p. 4357.

    Article  CAS  PubMed  Google Scholar 

  12. Slabbert, N.P., Tetrahedron, 1977, vol. 33, no. 7, p. 821.

    Article  CAS  Google Scholar 

  13. Lin, L.M., Li, W.S., Chen, W.L., and Yeh, A., J. Chin. Chem. Soc., 2010, vol. 57, no. 4B, p. 883.

    Article  CAS  Google Scholar 

  14. Dall’Acqua, S., Miolo, G., Innocenti, G., and Caffieri, S., Molecules, 2012, vol. 17, no. 8, p. 8898.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  15. Zenkevich, I.G., Eshchenko, A.Yu., Makarova, S.V., Vitenberg, A.G., Dobryakov, Yu.G., and Utsal, V.A., Molecules, 2007, vol. 12, no. 3, p. 654.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. Sokolova, R., Ramesova, S., Degano, I., Hromadova, M., Gal, J., and Zabka, J., Chem. Commun., 2012, vol. 48, no. 28, p. 3433.

    Article  CAS  Google Scholar 

  17. Boots, A.W., Kubben, N., Haenen, G.R., and Bast, A., Biochem. Biophys. Res. Commun., 2003, vol. 308, no. 3, p. 560.

    Article  CAS  PubMed  Google Scholar 

  18. Tsimogiannis, D., Samiotaki, M., Panayotou, G., and Oreopoulou, V., Molecules, 2007, vol. 12, no. 3, p. 593.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  19. Plazonic, A., Bucar, F., Males, Z., Mornar, A., Nigovic, B., and Kujundzic, N., Molecules, 2009, vol. 14, no. 7, p. 2466.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  20. Lee, J.S., Kim, D.H., Liu, K.-H., Oh, T.K., and Lee, C.H., Rapid Commun. Mass Spectrom., 2005, vol. 19, no. 23, p. 3539.

    Article  CAS  PubMed  Google Scholar 

  21. Okwu, D.E. and Ukanwa, N., Chem. Sin., 2010, vol. 1, no. 2, p. 21.

    CAS  Google Scholar 

  22. Harbaum, B., Hubbermann, E.M., Wolff, C., Herges, R., Zhu, Z., and Schwarz, K., J. Agric. Food Chem., 2007, vol. 5, no. 20, p. 8251.

    Article  CAS  Google Scholar 

  23. Prasain, J.K., Wang, C.C., and Barnes, S., Free Radical Biol. Med., 2007, vol. 37, no. 9, p. 1324.

    Article  CAS  Google Scholar 

  24. Rijke, E., Zappey, H., Ariese, F., Gooijer, C., and Brinkman, U.A., Anal Bioanal. Chem., 2004, vol. 378, no. 4, p. 995.

    Article  CAS  PubMed  Google Scholar 

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Authors and Affiliations

  1. Tomsk State University, 634050, Tomsk, Russia

    V. V. Khasanov, K. A. Dychko, S. S. Kravtsova & T. T. Kuryaeva

  2. Tomsk Regional Narkodispanser, 634000, Tomsk, Russia

    A. V. Labutin

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  1. V. V. Khasanov
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  2. K. A. Dychko
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  3. A. V. Labutin
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  4. S. S. Kravtsova
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  5. T. T. Kuryaeva
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Correspondence to V. V. Khasanov.

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Translated by V. Kudrinskaya

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Khasanov, V.V., Dychko, K.A., Labutin, A.V. et al. Products of the Intermediate Oxidation of Flavonoids in Aqueous Solutions and the Determination of Their Composition by High-Performance Liquid Chromatography–Mass Spectrometry. J Anal Chem 73, 1248–1252 (2018). https://doi.org/10.1134/S1061934818130051

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  • DOI: https://doi.org/10.1134/S1061934818130051

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