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Laccase-Catalyzed Heterocoupling of Dihydroquercetin and p-Aminobenzoic Acid: Effect of the Reaction Product on Cultured Cells

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Abstract

Derivatization of the natural flavonoid dihydroquercetin with p-aminobenzoic acid was carried out in an ethyl acetate/citric buffer biphasic system using laccase from the fungus Trametes hirsuta. The main reaction product yield was ~68 mol %. The product was characterized by 1H NMR, 13C NMR, and liquid chromatography-mass spectroscopy, and its structure was elucidated. The reaction product affected viability of cultured human rhabdomyosarcoma cells (RD cell line) in a dose-dependent manner and, therefore, can be of interest to pharmaceutical industry.

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Abbreviations

ABA:

p-aminobenzoic acid

ABTS:

2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)

COSY:

proton-proton correlation spectroscopy

DHQ:

dihydroquercetin

FBS:

fetal bovine serum

HMBC:

heteronuclear multiple-bond correlation spectroscopy

HSQC:

heteronuclear single quantum correlation spectroscopy

J :

spin-spin coupling constant

oligoDHQ:

dihydroquercetin oligomer

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Authors and Affiliations

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

    M. E. Khlupova, O. V. Morozova, I. S. Vasil’eva, G. P. Shumakovich, N. V. Pashintseva, L. I. Kovalev, S. S. Shishkin & A. I. Yaropolov

  2. Lomonosov Moscow State University, Faculty of Chemistry, 119899, Moscow, Russia

    V. A. Chertkov

  3. State Research Institute of Chemistry and Technology of Organoelement Compounds, 105118, Moscow, Russia

    A. K. Shestakova & A. V. Kisin

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

Correspondence to A. I. Yaropolov.

Additional information

Original Russian Text © M. E. Khlupova, O. V. Morozova, I. S. Vasil’eva, G. P. Shumakovich, N. V. Pashintseva, L. I. Kovalev, S. S. Shishkin, V. A. Chertkov, A. K. Shestakova, A. V. Kisin, A. I. Yaropolov, 2018, published in Biokhimiya, 2018, Vol. 83, No. 8, pp. 1247–1258.

Originally published in Biochemistry (Moscow) On-Line Papers in Press, as Manuscript BM18-018, July 9, 2018.

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Khlupova, M.E., Morozova, O.V., Vasil’eva, I.S. et al. Laccase-Catalyzed Heterocoupling of Dihydroquercetin and p-Aminobenzoic Acid: Effect of the Reaction Product on Cultured Cells. Biochemistry Moscow 83, 992–1001 (2018). https://doi.org/10.1134/S0006297918080102

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  • DOI: https://doi.org/10.1134/S0006297918080102

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