Enzymatic polymerization of dihydroquercetin using bilirubin oxidase

• Published in: Biochemistry (Moscow) Vol. 80; no. 2; pp. 233 - 241
• Main Authors: Khlupova, M. E., Vasil’eva, I. S., Shumakovich, G. P., Morozova, O. V., Chertkov, V. A., Shestakov, A. K., Kisin, A. V., Yaropolov, A. I.
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01-02-2015; Springer; Springer Nature B.V
• Subjects: Antioxidants - chemistry; Antioxidants - metabolism; Bilirubin; Biochemistry; Biomedical and Life Sciences; Biomedicine; Bioorganic Chemistry; Catalysts; Enzymes; Flavonoids; Health aspects; Life Sciences; Microbiology; Oxidases; Oxidation-Reduction; Oxidative stress; Oxidoreductases Acting on CH-CH Group Donors - metabolism; Physicochemical properties; Polymerization; Polymers; Polymers - chemistry; Quercetin; Quercetin - analogs & derivatives; Quercetin - chemistry; Quercetin - metabolism; C NMR spectra; H and; bilirubin oxidase; enzymatic polymerization; oligomers; dihydroquercetin
• ISSN: 0006-2979; 1608-3040
• DOI: 10.1134/S0006297915020108

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
1
H and
13
C 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.