Enzymatic polymerization of dihydroquercetin using bilirubin oxidase
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...
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| Published in: | Biochemistry (Moscow) Vol. 80; no. 2; pp. 233 - 241 |
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| Main Authors: | , , , , , , , |
| Format: | Journal Article |
| Language: | English |
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Pleiades Publishing
01-02-2015
Springer Springer Nature B.V |
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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
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. |
|---|---|
| AbstractList | 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. 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 'H and [sup.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. 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 ^sup 1^H and ^sup 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. 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. 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 'H and [sup.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. DOI: 10.1134/S0006297915020108 Key words: dihydroquercetin, enzymatic polymerization, bilirubin oxidase, oligomers, *H and [sup.13]C NMR spectra |
| Audience | Academic |
| Author | Vasil’eva, I. S. Shestakov, A. K. Morozova, O. V. Khlupova, M. E. Shumakovich, G. P. Chertkov, V. A. Kisin, A. V. Yaropolov, A. I. |
| Author_xml | – sequence: 1 givenname: M. E. surname: Khlupova fullname: Khlupova, M. E. organization: A. N. Bach Institute of Biochemistry, Russian Academy of Sciences – sequence: 2 givenname: I. S. surname: Vasil’eva fullname: Vasil’eva, I. S. organization: A. N. Bach Institute of Biochemistry, Russian Academy of Sciences – sequence: 3 givenname: G. P. surname: Shumakovich fullname: Shumakovich, G. P. organization: A. N. Bach Institute of Biochemistry, Russian Academy of Sciences – sequence: 4 givenname: O. V. surname: Morozova fullname: Morozova, O. V. organization: A. N. Bach Institute of Biochemistry, Russian Academy of Sciences – sequence: 5 givenname: V. A. surname: Chertkov fullname: Chertkov, V. A. organization: Faculty of Chemistry, Lomonosov Moscow State University – sequence: 6 givenname: A. K. surname: Shestakov fullname: Shestakov, A. K. organization: State Research Institute of Chemistry and Technology of Organoelement Compounds – sequence: 7 givenname: A. V. surname: Kisin fullname: Kisin, A. V. organization: State Research Institute of Chemistry and Technology of Organoelement Compounds – sequence: 8 givenname: A. I. surname: Yaropolov fullname: Yaropolov, A. I. email: yaropolov@inbi.ras.ru organization: A. N. Bach Institute of Biochemistry, Russian Academy of Sciences |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/25756538$$D View this record in MEDLINE/PubMed |
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| CitedBy_id | crossref_primary_10_1016_j_indcrop_2020_112419 crossref_primary_10_3390_nu14051069 crossref_primary_10_1016_j_molcatb_2015_11_010 crossref_primary_10_1021_acsabm_0c00170 |
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| Keywords | C NMR spectra H and bilirubin oxidase enzymatic polymerization oligomers dihydroquercetin |
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| Snippet | Dihydroquercetin (or taxifolin) is one of the most famous flavonoids and is abundant in Siberian larch (
Larix sibirica
). The oxidative polymerization of... Dihydroquercetin (or taxifolin) is one of the most famous flavonoids and is abundant in Siberian larch (Larix sibirica). The oxidative polymerization of... |
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| SubjectTerms | 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 |
| Title | Enzymatic polymerization of dihydroquercetin using bilirubin oxidase |
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