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

M. E. Khlupova1, O. V. Morozova1, I. S. Vasil’eva1, G. P. Shumakovich1, N. V. Pashintseva1, L. I. Kovalev1, S. S. Shishkin1, V. A. Chertkov2,a, A. K. Shestakova3,b, A. V. Kisin3, and A. I. Yaropolov1,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
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.
KEY WORDS: dihydroquercetin, p-aminobenzoic acid, laccase, biotransformation, 1H and 13C NMR spectra, proteomics

DOI: 10.1134/S0006297918080102