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

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M. E. Khlupova¹, O. V. Morozova¹, I. S. Vasil’eva¹, G. P. Shumakovich¹, N. V. Pashintseva¹, L. I. Kovalev¹, S. S. Shishkin¹, V. A. Chertkov^2,a, A. K. Shestakova^3,b, A. V. Kisin³, and A. I. Yaropolov^1,c*

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

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

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

^* To whom correspondence should be addressed.

Received January 19, 2018; Revision received March 20, 2018

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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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KEY WORDS: dihydroquercetin, p-aminobenzoic acid, laccase, biotransformation, ¹H and ¹³C NMR spectra, proteomics

DOI: 10.1134/S0006297918080102

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