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Enzymatic polymerization of dihydroquercetin using bilirubin oxidase

Authors
  • Khlupova, M. E.1
  • Vasil’eva, I. S.1
  • Shumakovich, G. P.1
  • Morozova, O. V.1
  • Chertkov, V. A.2
  • Shestakov, A. K.3
  • Kisin, A. V.3
  • Yaropolov, A. I.1
  • 1 Russian Academy of Sciences, A. N. Bach Institute of Biochemistry, Leninsky pr. 33, Moscow, 119071, Russia , Moscow (Russia)
  • 2 Lomonosov Moscow State University, Faculty of Chemistry, Moscow, 119991, Russia , Moscow (Russia)
  • 3 State Research Institute of Chemistry and Technology of Organoelement Compounds, Moscow, 105118, Russia , Moscow (Russia)
Type
Published Article
Journal
Biochemistry (Moscow)
Publisher
Pleiades Publishing
Publication Date
Feb 18, 2015
Volume
80
Issue
2
Pages
233–241
Identifiers
DOI: 10.1134/S0006297915020108
Source
Springer Nature
Keywords
License
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Abstract

Dihydroquercetin (or taxifolin) is one of the most famous flavonoids and is abundant in Siberian larch (Larix sibirica). The oxidative polymerization of dihydroquercetin (DHQ) using bilirubin oxidase as a biocatalyst was investigated and some physicochemical properties of the products were studied. DHQ oligomers (oligoDHQ) with molecular mass of 2800 and polydispersity of 8.6 were obtained by enzymatic reaction under optimal conditions. The oligomers appeared to be soluble in dimethylsulfoxide, dimethylformamide, and methanol. UV-visible spectra of oligoDHQ in dimethylsulfoxide indicated the presence of highly conjugated bonds. The synthesized oligoDHQ was also characterized by FTIR and 1H and 13C NMR spectroscopy. Comparison of NMR spectra of oligoDHQ with DHQ monomer and the parent flavonoids revealed irregular structure of a polymer formed via the enzymatic oxidation of DHQ followed by nonselective radical polymerization. As compared with the monomer, oligoDHQ demonstrated higher thermal stability and high antioxidant activity.

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