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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| Veröffentlicht in: | Biochemistry (Moscow) 2015-02, Vol.80 (2), p.233-241 |
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| creator | 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. |
| description | 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. |
| doi_str_mv | 10.1134/S0006297915020108 |
| format | Article |
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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.</description><identifier>ISSN: 0006-2979</identifier><identifier>EISSN: 1608-3040</identifier><identifier>DOI: 10.1134/S0006297915020108</identifier><identifier>PMID: 25756538</identifier><language>eng</language><publisher>Moscow: Pleiades Publishing</publisher><subject>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</subject><ispartof>Biochemistry (Moscow), 2015-02, Vol.80 (2), p.233-241</ispartof><rights>Pleiades Publishing, Ltd. 2015</rights><rights>COPYRIGHT 2015 Springer</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c439t-9b1434a4c5ff877335823e0b911ae20a5f1b5b4cd0d25a42c93297e1addbf9943</citedby><cites>FETCH-LOGICAL-c439t-9b1434a4c5ff877335823e0b911ae20a5f1b5b4cd0d25a42c93297e1addbf9943</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1134/S0006297915020108$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1134/S0006297915020108$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,41464,42533,51294</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25756538$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Khlupova, M. E.</creatorcontrib><creatorcontrib>Vasil’eva, I. S.</creatorcontrib><creatorcontrib>Shumakovich, G. P.</creatorcontrib><creatorcontrib>Morozova, O. V.</creatorcontrib><creatorcontrib>Chertkov, V. A.</creatorcontrib><creatorcontrib>Shestakov, A. K.</creatorcontrib><creatorcontrib>Kisin, A. V.</creatorcontrib><creatorcontrib>Yaropolov, A. I.</creatorcontrib><title>Enzymatic polymerization of dihydroquercetin using bilirubin oxidase</title><title>Biochemistry (Moscow)</title><addtitle>Biochemistry Moscow</addtitle><addtitle>Biochemistry (Mosc)</addtitle><description>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.</description><subject>Antioxidants - chemistry</subject><subject>Antioxidants - metabolism</subject><subject>Bilirubin</subject><subject>Biochemistry</subject><subject>Biomedical and Life Sciences</subject><subject>Biomedicine</subject><subject>Bioorganic Chemistry</subject><subject>Catalysts</subject><subject>Enzymes</subject><subject>Flavonoids</subject><subject>Health aspects</subject><subject>Life Sciences</subject><subject>Microbiology</subject><subject>Oxidases</subject><subject>Oxidation-Reduction</subject><subject>Oxidative stress</subject><subject>Oxidoreductases Acting on CH-CH Group Donors - metabolism</subject><subject>Physicochemical properties</subject><subject>Polymerization</subject><subject>Polymers</subject><subject>Polymers - chemistry</subject><subject>Quercetin</subject><subject>Quercetin - analogs & derivatives</subject><subject>Quercetin - chemistry</subject><subject>Quercetin - metabolism</subject><issn>0006-2979</issn><issn>1608-3040</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>BENPR</sourceid><recordid>eNp1kUtP3DAUha2qVZlO-wO6qSKxYRN6_Uy8RBQoElIXhXXk-DE1SuypnUgMv74ehkcpVF5Y997vHB37IvQZwyHGlH39CQCCyEZiDgQwtG_QAgtoawoM3qLFdlxv53voQ87XpSQg6Xu0R3jDBaftAn07CbebUU1eV-s4bEab_G2pYqiiq4z_tTEp_p5t0nbyoZqzD6uq94NPc1_qeOONyvYjeufUkO2n-3uJrk5PLo-_1xc_zs6Pjy5qzaicatljRplimjvXNg2lvCXUQi8xVpaA4g73vGfagCFcMaIlLeEtVsb0TkpGl-hg57u-C5WnbvRZ22FQwcY5d1gIImhLoCno_j_odZxTKOkKxbloBAb8RK3UYDsfXJyS0lvT7ohBI4TE5cOW6PAVqhxjR69jsM6X_jMB3gl0ijkn67p18qNKmw5Dt91c92JzRfPlPvDcj9Y8Kh5WVQCyA3IZhZVNf73ov65_AHp0oEo</recordid><startdate>20150201</startdate><enddate>20150201</enddate><creator>Khlupova, M. 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E.</au><au>Vasil’eva, I. S.</au><au>Shumakovich, G. P.</au><au>Morozova, O. V.</au><au>Chertkov, V. A.</au><au>Shestakov, A. K.</au><au>Kisin, A. V.</au><au>Yaropolov, A. I.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enzymatic polymerization of dihydroquercetin using bilirubin oxidase</atitle><jtitle>Biochemistry (Moscow)</jtitle><stitle>Biochemistry Moscow</stitle><addtitle>Biochemistry (Mosc)</addtitle><date>2015-02-01</date><risdate>2015</risdate><volume>80</volume><issue>2</issue><spage>233</spage><epage>241</epage><pages>233-241</pages><issn>0006-2979</issn><eissn>1608-3040</eissn><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.</abstract><cop>Moscow</cop><pub>Pleiades Publishing</pub><pmid>25756538</pmid><doi>10.1134/S0006297915020108</doi><tpages>9</tpages></addata></record> |
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| ispartof | Biochemistry (Moscow), 2015-02, Vol.80 (2), p.233-241 |
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| 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 |
| title | Enzymatic polymerization of dihydroquercetin using bilirubin oxidase |
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