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Multicopper Oxidase-Catalyzed Biotransformation of Dihydroquercetin

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Moscow University Chemistry Bulletin Aims and scope

Abstract

Multicopper oxidases such as bilirubin oxidase (BOD) from Myrothecium verrucaria and laccase (LC) from the basidial fungus Trametes hirsuta have been used as catalysts in dihydroquercetin (DHQ) oxidative polymerization. The conditions selected enabled good yields of DHQ oligomers, which were then analyzed using UV-vis, FTIR, 1Н and 13С NMR spectroscopy. DHQ oligomers synthesized using both enzymes showed higher thermostability as compared with the monomer. Depending on the oxidase, the products of DHQ polymerization differed in physicochemical properties, and as shown by NMR studies, had different structures.

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References

  1. Baldrian, P., FEMS Microbiol. Rev., 2006, vol. 30, no. 2, p. 215.

    Article  CAS  PubMed  Google Scholar 

  2. Solomon, E.I., Sundaram, U.M., and Machonkin, T.E., Chem. Rev., 1996, vol. 96, no. 7, p. 2563.

    Article  CAS  Google Scholar 

  3. Witayakran, S. and Ragauskas, A.J., Adv. Synth. Catal., 2009, vol. 351, no. 9, p. 1187.

    Article  CAS  Google Scholar 

  4. Walde, P. and Guo, Z., Soft Matter, 2011, vol. 7, no. 2, p. 316.

    Article  CAS  Google Scholar 

  5. Hollmann, F. and Arends, I.W.C.E., Polymers, 2012, vol. 4, no. 1, p. 759.

    Article  CAS  Google Scholar 

  6. Mejias, L., Reihmann, M.H., Sepulveda-Boza, S., and Ritter, H., Macromol. Biosci., 2002, vol. 2, no. 1, p. 24.

    Article  CAS  Google Scholar 

  7. Kim, Y.-J., Uyama, H., and Kobayashi, Sh., Macromolecules, 2003, vol. 36, no. 14, p. 5058.

    Article  CAS  Google Scholar 

  8. Magharabi, M. and Faramazzi, M.A., Adv. Synth. Catal., 2014, vol. 356, no. 5, p. 897.

    Article  CAS  Google Scholar 

  9. Hagerman, A.E., Riedl, K.M., Jones, G.A., Sovik, K.N., Ritchard, N.T., Hartzfeld, P.W., and Riechel, T.L., J. Agric. Food Chem., 1998, vol. 46, no. 5, p. 1887.

    Article  CAS  PubMed  Google Scholar 

  10. Kurisawa, M., Chung, J.E., Uyama, H., and Kobayashi, S., Biomacromolecules, 2003, vol. 4, no. 5, p. 1394.

    Article  CAS  PubMed  Google Scholar 

  11. Kurisawa, M., Chung, J.E., Uyama, H., and Kobayashi, S., Macromol. Biosci., 2003, vol. 3, no. 12, p. 758.

    Article  CAS  Google Scholar 

  12. Zhao, J., Wang, J., Chen, Y., and Agarwa, R., Carcinogenes, vol. 20, no. 9, p. 1737.

  13. Makena, P.S., Pierce, S.C., Chung, K.-T., and Sinclair, S.E., Environ. Mol. Mutagen., 2009, vol. 50, no. 6, p. 451.

    Article  CAS  PubMed  Google Scholar 

  14. Weidmann, A.E., Eur. J. Pharmacol., 2012, vol. 684, nos. 1–3, p. 19.

    Article  CAS  PubMed  Google Scholar 

  15. Pantouris, G. and Mowat, Ch.G., Biochem. Biophys. Res. Commun., 2014, vol. 443, no. 1, p. 28.

    Article  CAS  PubMed  Google Scholar 

  16. Polyak, S.J., Morishima, Ch., Lohmann, V., Pal, S., Lee, D.Y.W., Liu, Y., and Graf, T.N., Proc. Natl. Acad. Sci. U. S. A., 2010, vol. 107, no. 13, p. 5995.

    Article  PubMed  PubMed Central  Google Scholar 

  17. Soto, M., Murakami, K., Uno, M., Ikubo, H., Nakagama, Yu., Katayama, S., Akagi, K., and Irie, K., Biosci. Biotechnol. Biochem., 2013, vol. 77, no. 5, p. 1100.

    Article  CAS  Google Scholar 

  18. Bordoni, A., Hrelia, S., Angeloni, C., Giordano, E., Guarnieri, C., Caldarera, C.M., and Bia, P.L., J. Nutr. Biochem., 2002, vol. 13, no. 2, p. 103.

    Article  CAS  PubMed  Google Scholar 

  19. Ferry, D.R., Smith, A., Malkhandi, J., Fyfe, D.W., Takats, P.G., Anderson, D., Baker, J., and Kerr, D.J., Clin. Cancer Res., 1996, vol. 2, no. 4, p. 659.

    CAS  PubMed  Google Scholar 

  20. Ono, K., Nakane, H., Fukushima, M., Chermann, J.-C., and Barre-Sinoussi, F., Eur. J. Biochem., 1990, vol. 190, no. 3, p. 469.

    Article  CAS  PubMed  Google Scholar 

  21. Zhang, Zh.R., Zaharna, M.A., Wong, M.M.-K., Chin, S.-K., and Cheng, H.-Y., PLoS One, 2013, vol. 8, no. 1.

    Google Scholar 

  22. Hollman, P.C. and Katan, M.B., Biomed. Pharmacother., 1997, vol. 51, no. 8, p. 305.

    Article  CAS  PubMed  Google Scholar 

  23. Gorshina, E.S., Rusinova, T.V., Biryukov, V.V., Morozova, O.V., Shleev, S.V., and Yaropolov, A.I., Appl. Biochem. Microbiol., 2006, vol. 42, no. 6, p. 558.

    Article  CAS  Google Scholar 

  24. Brand-Williams, W., Cuvelier, M.E., and Berset, C., LWT—Food Sci. Technol., 1995, vol. 28, no. 1, p. 25.

    Article  CAS  Google Scholar 

  25. Bruno, F.F., Trotta, A., Fossey, S., Nagarajan, S., Nagarajan, R., Samuelson, L.A., and Kumar, J., J. Macromol. Sci., Part A: Pure Appl.Chem., 2010, vol. 47, no. 12, p. 1191.

    CAS  Google Scholar 

  26. Park, S.Y., Kim, YH., Won, K., and Song, B.K., J. Mol. Catal. B: Enzym., 2009, vol. 57, no. 1.

    Google Scholar 

  27. Won, K., Kim, Y.H., An, E.S., Lee, Y.S., and Song, B.K., Biomacromolecules, 2004, vol. 5, no. 1, p. 1.

    Article  CAS  PubMed  Google Scholar 

  28. Kiehlmann, E. and Slade, P.W., J. Nat. Prod., 2003, vol. 66, no. 12, p. 1562.

    Article  CAS  PubMed  Google Scholar 

  29. Kolesnik, Y.A., Titova, E.V., Chertkov, V.A., Tashlitskiy, V.N., Tichonov, V.P., and Shmatkov, D.A., Planta Med., 2011, vol. 77, no. 12, p. 1266.

    Article  Google Scholar 

  30. Sinha, R., Joshi, A., Joshi, U.J., Srivastava, S., and Govil, G., Eur. J. Med. Chem., 2014, vol. 80, p. 285.

    Article  CAS  PubMed  Google Scholar 

  31. Cotterill, P.J., Scheinmann, F., and Stenhouse, I.A., J. Chem. Soc., Perkin Trans. 1, 1978, no. 6, p. 532.

    Article  Google Scholar 

Download references

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Authors and Affiliations

  1. Bach Institute of Biochemistry, Research Center of Biotechnology, Russian Academy of Sciences, Moscow, 119071, Russia

    M. E. Khlupova, I. S. Vasil’eva, G. P. Shumakovich, O. V. Morozova & A. I. Yaropolov

  2. Department of Enzymology, Faculty of Chemistry, Moscow State University, Moscow, 119991, Russia

    E. A. Zaitseva

  3. Department of Organic Chemistry, Faculty of Chemistry, Moscow State University, Moscow, 119991, Russia

    V. A. Chertkov

  4. State Research Institute of Chemistry and Technology of Organoelement Compounds, Moscow, 119334, Russia

    A. K. Shestakova & A. V. Kisin

Authors
  1. M. E. Khlupova
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  2. I. S. Vasil’eva
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  3. G. P. Shumakovich
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  4. O. V. Morozova
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  5. E. A. Zaitseva
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  6. V. A. Chertkov
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  7. A. K. Shestakova
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  8. A. V. Kisin
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  9. A. I. Yaropolov
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Corresponding author

Correspondence to A. I. Yaropolov.

Additional information

Original Russian Text © M.E. Khlupova, I.S. Vasil’eva, G.P. Shumakovich, O.V. Morozova, E.A. Zaitseva, V.A. Chertkov, A.K. Shestakova, A.V. Kisin, A.I. Yaropolov, 2018, published in Vestnik Moskovskogo Universiteta, Seriya 2: Khimiya, 2018, No. 5, pp. 361–368.

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Khlupova, M.E., Vasil’eva, I.S., Shumakovich, G.P. et al. Multicopper Oxidase-Catalyzed Biotransformation of Dihydroquercetin. Moscow Univ. Chem. Bull. 73, 237–243 (2018). https://doi.org/10.3103/S002713141805005X

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  • DOI: https://doi.org/10.3103/S002713141805005X

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