<?xml version="1.0" encoding="UTF-8"?>
<!DOCTYPE article PUBLIC "-//NLM//DTD JATS (Z39.96) Journal Publishing DTD v1.3 20210610//EN" "JATS-journalpublishing1-3.dtd">
<article article-type="research-article" dtd-version="1.3" xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xml:lang="ru"><front><journal-meta><journal-id journal-id-type="publisher-id">nbsprot</journal-id><journal-title-group><journal-title xml:lang="ru">Вестник войск РХБ защиты</journal-title><trans-title-group xml:lang="en"><trans-title>Journal of NBC Protection Corps</trans-title></trans-title-group></journal-title-group><issn pub-type="ppub">2587-5728</issn><issn pub-type="epub">3034-2791</issn><publisher><publisher-name>27 Научный центр</publisher-name></publisher></journal-meta><article-meta><article-id pub-id-type="doi">10.35825/2587-5728-2023-7-3-237-247</article-id><article-id custom-type="edn" pub-id-type="custom">wdghbh</article-id><article-id custom-type="elpub" pub-id-type="custom">nbsprot-319</article-id><article-categories><subj-group subj-group-type="heading"><subject>Research Article</subject></subj-group><subj-group subj-group-type="section-heading" xml:lang="ru"><subject>РАДИАЦИОННАЯ БЕЗОПАСНОСТЬ И ЗАЩИТА ОТ ЯДЕРНОГО ОРУЖИЯ</subject></subj-group><subj-group subj-group-type="section-heading" xml:lang="en"><subject>RADIATION SAFETY AND NUCLEAR WEAPONS DEFENSE</subject></subj-group></article-categories><title-group><article-title>Реакционные пути окислительной трансформации радиопротектора кверцетина</article-title><trans-title-group xml:lang="en"><trans-title>Reaction Pathways of Oxidative Transformation of the Radioprotector Quercetin</trans-title></trans-title-group></title-group><contrib-group><contrib contrib-type="author" corresp="yes"><contrib-id contrib-id-type="orcid">https://orcid.org/0009-0004-6866-218X</contrib-id><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Оличева</surname><given-names>В. В.</given-names></name><name name-style="western" xml:lang="en"><surname>Olicheva</surname><given-names>V. V.</given-names></name></name-alternatives><bio xml:lang="ru"><p>Оличева Вера Владимировна, студентка Института Фармации им. А.П. Нелюбина</p><p>119048, г. Москва, ул. Трубецкая, д. 8, стр. 2</p></bio><bio xml:lang="en"><p>Vera V. Olicheva, student. Institute of Pharmacy named after A.P. Nelyubin, Sechenov University</p><p>Trubetskaya Str., 8-2, Moscow 119991</p></bio><email xlink:type="simple">vera.olicheva@inbox.ru</email><xref ref-type="aff" rid="aff-1"/></contrib><contrib contrib-type="author" corresp="yes"><contrib-id contrib-id-type="orcid">https://orcid.org/0009-0003-3252-6322</contrib-id><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Титова</surname><given-names>А. Д.</given-names></name><name name-style="western" xml:lang="en"><surname>Titova</surname><given-names>A. D.</given-names></name></name-alternatives><bio xml:lang="ru"><p>Титова Александра Дмитриевна, аспирантка</p><p>119991, г. Москва, Ленинский проспект, д. 47</p></bio><bio xml:lang="en"><p>Alexandra D. Titova, postgrauate</p><p>Leninsky Avenue, 47, Moscow 119991</p></bio><email xlink:type="simple">secretary@ioc.ac.ru</email><xref ref-type="aff" rid="aff-2"/></contrib><contrib contrib-type="author" corresp="yes"><contrib-id contrib-id-type="orcid">https://orcid.org/0000-0001-9822-3322</contrib-id><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Ильясов</surname><given-names>И. Р.</given-names></name><name name-style="western" xml:lang="en"><surname>Ilyasov</surname><given-names>I. R.</given-names></name></name-alternatives><bio xml:lang="ru"><p>Ильясов Игорь Равилевич, доцент кафедры химии Института Фармации им. А.П. Нелюбина, канд. фарм. наук, доцент</p><p>119048, г. Москва, ул. Трубецкая, д. 8, стр. 2</p></bio><bio xml:lang="en"><p>Igor R. Iyasov, Associate Professor. Department of Chemistry. Institute of Pharmacy named after A.P. Nelyubin, Sechenov University. Cand. Sci. (Pharm.), Associate Professor</p><p>Trubetskaya Str., 8-2, Moscow 119991</p></bio><email xlink:type="simple">rectorat@staff.sechenov.ru</email><xref ref-type="aff" rid="aff-1"/></contrib><contrib contrib-type="author" corresp="yes"><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Фатеенков</surname><given-names>В. Н.</given-names></name><name name-style="western" xml:lang="en"><surname>Fateenkov</surname><given-names>V. N.</given-names></name></name-alternatives><bio xml:lang="ru"><p>Фатеенков Владимир Николаевич, начальник отдела, канд. воен. наук, доцент, профессор АВН</p><p>111024, г. Москва, проезд Энтузиастов, д. 19</p></bio><bio xml:lang="en"><p>Vladimir N. Fateenkov, head of Department. Cand. Sci. (Military), Associate Professor, Professor at the AMS</p><p>Entuziastov Passage, 19, Moscow 111024</p></bio><email xlink:type="simple">27nc_1@mil.ru</email><xref ref-type="aff" rid="aff-3"/></contrib><contrib contrib-type="author" corresp="yes"><name-alternatives><name name-style="eastern" xml:lang="ru"><surname>Браун</surname><given-names>А. В.</given-names></name><name name-style="western" xml:lang="en"><surname>Braun</surname><given-names>A. V.</given-names></name></name-alternatives><bio xml:lang="ru"><p>Браун Аркадий Владимирович, старший научный сотрудник, канд. хим. наук</p><p>111024, г. Москва, проезд Энтузиастов, д. 19</p></bio><bio xml:lang="en"><p>Arkadii V. Braun, research associate. Cand. Sci. (Chem.)</p><p>Entuziastov Passage, 19, Moscow 111024</p></bio><email xlink:type="simple">27nc_1@mil.ru</email><xref ref-type="aff" rid="aff-3"/></contrib></contrib-group><aff-alternatives id="aff-1"><aff xml:lang="ru"><institution>Федеральное государственное автономное образовательное учреждение высшего образования «Первый Московский государственный медицинский университет имени И.М. Сеченова» Министерства здравоохранения Российской Федерации (Сеченовский Университет)</institution><country>Россия</country></aff><aff xml:lang="en"><institution>Federal State Autonomous Educational Institution of Higher Education «I.M. Sechenov First Moscow State Medical University» of the Ministry of Health of the Russian Federation (Sechenov University)</institution><country>Russian Federation</country></aff></aff-alternatives><aff-alternatives id="aff-2"><aff xml:lang="ru"><institution>Федеральное государственное бюджетное учреждение науки «Институт органической химии им. Н.Д. Зелинского Российской академии наук»</institution><country>Россия</country></aff><aff xml:lang="en"><institution>Federal State Budgetary Establishment «N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences»</institution><country>Russian Federation</country></aff></aff-alternatives><aff-alternatives id="aff-3"><aff xml:lang="ru"><institution>Федеральное государственное бюджетное учреждение «27 Научный центр» Министерства обороны Российской Федерации</institution><country>Россия</country></aff><aff xml:lang="en"><institution>Federal State Budgetary Establishment «27 Scientific Centre» of the Ministry of Defence of the Russian Federation</institution><country>Russian Federation</country></aff></aff-alternatives><pub-date pub-type="collection"><year>2023</year></pub-date><pub-date pub-type="epub"><day>08</day><month>01</month><year>2024</year></pub-date><volume>7</volume><issue>3</issue><fpage>237</fpage><lpage>247</lpage><permissions><copyright-statement>Copyright &amp;#x00A9; Оличева В.В., Титова А.Д., Ильясов И.Р., Фатеенков В.Н., Браун А.В., 2024</copyright-statement><copyright-year>2024</copyright-year><copyright-holder xml:lang="ru">Оличева В.В., Титова А.Д., Ильясов И.Р., Фатеенков В.Н., Браун А.В.</copyright-holder><copyright-holder xml:lang="en">Olicheva V.V., Titova A.D., Ilyasov I.R., Fateenkov V.N., Braun A.V.</copyright-holder><license xml:lang="ru" license-type="creative-commons-attribution" xlink:href="https://creativecommons.org/licenses/by/4.0/" xlink:type="simple"><license-p>Данная работа распространяется под лицензией Creative Commons Attribution 4.0.</license-p></license><license xml:lang="en" license-type="creative-commons-attribution" xlink:href="https://creativecommons.org/licenses/by/4.0/" xlink:type="simple"><license-p>This work is licensed under a Creative Commons Attribution 4.0 License.</license-p></license></permissions><self-uri xlink:href="https://www.nbsprot.ru/jour/article/view/319">https://www.nbsprot.ru/jour/article/view/319</self-uri><abstract><p>Кверцетин является одним из наиболее перспективных природных полифенольных радиопротекторных соединений. Это свойство основано на его радикал-улавливающей активности и высокой антиоксидантной емкости, в проявлении которой значительную роль играют продукты окислительной деградации кверцетина. Образование специфических метаболитов в процессе окисления кверцетина может обуславливать не только его радиопротекторные свойства, но и токсические проявления. Цель работы – обобщение полученных ранее данных в отношении реакционных путей окислительной трансформации кверцетина. Материалы и методы. Использовали общедоступные научные публикации, посвященные изучению процессов трансформации кверцетина. Метод анализа – описательный. Обсуждение результатов. Представлен обзор научных работ, посвященных кислородному окислению, радикал-инициируемого окисления, электрохимического и ферментативного окислений, приведены возможные продукты трансформации кверцетина и механизмы их образования. Наиболее характерные пути окисления кверцетина обусловлены химической структурой колец, проявляющей специфическую реакционную способность. Выявлено влияние состава растворителей на продукты окисления при автоокислении кверцетина, в то время как радикальная и электрохимическая модели окисления отличаются наличием полимерных аддуктов. Попадая в живой организм, кверцетин может связывать свободные радикалы, предотвращая тем самым пагубное влияние радиации, то есть обладает свойствами радиопротектора. Выводы. Кверцетин можно рассматривать как потенциальный радиопротектор за счет способности связывать свободные радикалы, образующиеся в биологических жидкостях живых организмов, подвергшихся воздействию радиации.</p></abstract><trans-abstract xml:lang="en"><p>Quercetin is one of the most promising natural polyphenolic radioprotective compounds. This property is based on its radical-scavenging activity and high antioxidant capacity, in the manifestation of which the products of oxidative degradation of quercetin play a significant role. The formation of specific metabolites during the oxidation of quercetin can determine not only its radioprotective properties, but also toxic manifestations. The purpose of this article is to summarize previously obtained data regarding the reaction pathways of oxidative transformation of quercetin. Materials and methods. We used publicly available scientific publications dedicated to the study of quercetin transformation processes. The method of analysis is descriptive. The discussion of the results. A review of scientific works dedicated to oxygen oxidation, radical-initiated oxidation, electrochemical and enzymatic oxidation is presented, possible transformation products of quercetin and the mechanisms of their formation are given. The most characteristic oxidation pathways of quercetin are determined by the chemical structure of the rings, which exhibit specific reactivity. The influence of the solvent composition on the oxidation products during the autoxidation of quercetin was revealed, while the radical and electrochemical models of oxidation differ in the presence of polymer adducts. Once in a living organism, quercetin can bind free radicals, thereby preventing the harmful effects of radiation, that is, it has the properties of a radioprotector. Conclusions. Quercetin can be considered as a potential radioprotector due to its ability to bind free radicals formed in the biological fluids of living organisms exposed to radiation.</p></trans-abstract><kwd-group xml:lang="ru"><kwd>антиоксидант</kwd><kwd>кверцетин</kwd><kwd>полифенольное соединение</kwd><kwd>радиация</kwd><kwd>радиопротектор</kwd><kwd>трансформация</kwd></kwd-group><kwd-group xml:lang="en"><kwd>antioxidant</kwd><kwd>polyphenolic compound</kwd><kwd>quercetin</kwd><kwd>radiation</kwd><kwd>radioprotector</kwd><kwd>transformation</kwd></kwd-group></article-meta></front><back><ref-list><title>References</title><ref id="cit1"><label>1</label><citation-alternatives><mixed-citation xml:lang="ru">Anand David AV, Arulmoli R, Parasuraman S. Overviews of Biological Importance of Quercetin: A Bioactive Flavonoid. Pharmacogn Rev. 2016;10(20):84–9. https://doi.org/10.4103/0973-7847.194044</mixed-citation><mixed-citation xml:lang="en">Anand David AV, Arulmoli R, Parasuraman S. Overviews of Biological Importance of Quercetin: A Bioactive Flavonoid. Pharmacogn Rev. 2016;10(20):84–9. https://doi.org/10.4103/0973-7847.194044</mixed-citation></citation-alternatives></ref><ref id="cit2"><label>2</label><citation-alternatives><mixed-citation xml:lang="ru">Oboh G, Odubanjo V, Bello F, Ademosun AO, Oyeleye SI, Nwanna Emem EE, Ademiluyi AO. Aqueous extracts of avocado pear (Persea americana Mill.) leaves and seeds exhibit anti-cholinesterases and antioxidant activities in vitro. J Basic Clin Physiol Pharmacol. 2016;27(2):131–40. https://doi.org/10.1515/jbcpp-2015-0049</mixed-citation><mixed-citation xml:lang="en">Oboh G, Odubanjo V, Bello F, Ademosun AO, Oyeleye SI, Nwanna Emem EE, Ademiluyi AO. Aqueous extracts of avocado pear (Persea americana Mill.) leaves and seeds exhibit anti-cholinesterases and antioxidant activities in vitro. J Basic Clin Physiol Pharmacol. 2016;27(2):131–40. https://doi.org/10.1515/jbcpp-2015-0049</mixed-citation></citation-alternatives></ref><ref id="cit3"><label>3</label><citation-alternatives><mixed-citation xml:lang="ru">Benković V, Knezević AH, Dikić D, Lisicić D, Orsolić N, Basić I, Kopjar N. Radioprotective effects of quercetin and ethanolic extract of propolis in gamma-irradiated mice. Arh Hig Rada Toksikol. 2009;60(2):129–38. https://doi.org/10.2478/10004-1254-60-2009-1908</mixed-citation><mixed-citation xml:lang="en">Benković V, Knezević AH, Dikić D, Lisicić D, Orsolić N, Basić I, Kopjar N. Radioprotective effects of quercetin and ethanolic extract of propolis in gamma-irradiated mice. Arh Hig Rada Toksikol. 2009;60(2):129–38. https://doi.org/10.2478/10004-1254-60-2009-1908</mixed-citation></citation-alternatives></ref><ref id="cit4"><label>4</label><citation-alternatives><mixed-citation xml:lang="ru">Patil SL, Mallaiah SH, Patil RK. Antioxidative and radioprotective potential of rutin and quercetin in Swiss albino mice exposed to gamma radiation. J Med Phys. 2013;38(2):87–92. https://doi.org/10.4103/0971-6203.111321</mixed-citation><mixed-citation xml:lang="en">Patil SL, Mallaiah SH, Patil RK. Antioxidative and radioprotective potential of rutin and quercetin in Swiss albino mice exposed to gamma radiation. J Med Phys. 2013;38(2):87–92. https://doi.org/10.4103/0971-6203.111321</mixed-citation></citation-alternatives></ref><ref id="cit5"><label>5</label><citation-alternatives><mixed-citation xml:lang="ru">Nierenstein M, Whedale M Anthocyanin I. Anthocyanin-like Oxidation Products of Quercetin. Ber Deut Chem Ges. 1912;(44):3487–91.</mixed-citation><mixed-citation xml:lang="en">Nierenstein M, Whedale M Anthocyanin I. Anthocyanin-like Oxidation Products of Quercetin. Ber Deut Chem Ges. 1912;(44):3487–91.</mixed-citation></citation-alternatives></ref><ref id="cit6"><label>6</label><citation-alternatives><mixed-citation xml:lang="ru">Fuentes J, Atala E, Pastene E, Carrasco-Pozo C, Speisky H. Quercetin Oxidation Paradoxically Enhances its Antioxidant and Cytoprotective Properties. J Agric Food Chem. 2017;65(50):11002–10. https://doi.org/10.1021/acs.jafc.7b05214</mixed-citation><mixed-citation xml:lang="en">Fuentes J, Atala E, Pastene E, Carrasco-Pozo C, Speisky H. Quercetin Oxidation Paradoxically Enhances its Antioxidant and Cytoprotective Properties. J Agric Food Chem. 2017;65(50):11002–10. https://doi.org/10.1021/acs.jafc.7b05214</mixed-citation></citation-alternatives></ref><ref id="cit7"><label>7</label><citation-alternatives><mixed-citation xml:lang="ru">Zenkevich IG, Eshchenko AY, Makarova SV, Vitenberg AG, Dobryakov YG, Utsal VA. Identification of the products of oxidation of quercetin by air oxygen at ambient temperature. Molecules. 2007;12(3):654–72. https://doi.org/10.3390/12030654</mixed-citation><mixed-citation xml:lang="en">Zenkevich IG, Eshchenko AY, Makarova SV, Vitenberg AG, Dobryakov YG, Utsal VA. Identification of the products of oxidation of quercetin by air oxygen at ambient temperature. Molecules. 2007;12(3):654–72. https://doi.org/10.3390/12030654</mixed-citation></citation-alternatives></ref><ref id="cit8"><label>8</label><citation-alternatives><mixed-citation xml:lang="ru">Черников ДА, Пальшин ВА, Баженов БН, Сафронов АЮ, Кашевский АВ. Гидроксиацетофеноны – новые модели при изучении электроокисления кверцетина. Известия ВУЗов. Химия и химическая техно- логия. 2012;55(8):43–7. Chernikov DA, Palshin VA, Bazhenov BN, Safronov AYu, Kashevsky AV. Hydroxyacetophenones are new models in the study of quercetin electrooxidation. ChemChemTech [Izv Vyssh Uchebn Zaved Khim Khim Tekhnol]. 2012;55(8):43–7 (In Russian).</mixed-citation><mixed-citation xml:lang="en">Черников ДА, Пальшин ВА, Баженов БН, Сафронов АЮ, Кашевский АВ. Гидроксиацетофеноны – новые модели при изучении электроокисления кверцетина. Известия ВУЗов. Химия и химическая техно- логия. 2012;55(8):43–7. Chernikov DA, Palshin VA, Bazhenov BN, Safronov AYu, Kashevsky AV. Hydroxyacetophenones are new models in the study of quercetin electrooxidation. ChemChemTech [Izv Vyssh Uchebn Zaved Khim Khim Tekhnol]. 2012;55(8):43–7 (In Russian).</mixed-citation></citation-alternatives></ref><ref id="cit9"><label>9</label><citation-alternatives><mixed-citation xml:lang="ru">Makhotkina O, Kilmartin PA. Electrochemical Oxidation of Wine Polyphenols in the Presence of Sulfur Dioxide. J Agric Food Chem. 2013;61(23):5573–81. https://doi.org/10.1021/jf400282z</mixed-citation><mixed-citation xml:lang="en">Makhotkina O, Kilmartin PA. Electrochemical Oxidation of Wine Polyphenols in the Presence of Sulfur Dioxide. J Agric Food Chem. 2013;61(23):5573–81. https://doi.org/10.1021/jf400282z</mixed-citation></citation-alternatives></ref><ref id="cit10"><label>10</label><citation-alternatives><mixed-citation xml:lang="ru">Sokolová R, Degano I, Ramešová S, Bulíčková J, Hromadová M, Gál M, et al. The oxidation mechanism of the antioxidant quercetin in nonaqueous media. Electrochimica Acta. 2011;56(21):7421–7. https://doi.org/10.1016/j.electacta.2011.04.121</mixed-citation><mixed-citation xml:lang="en">Sokolová R, Degano I, Ramešová S, Bulíčková J, Hromadová M, Gál M, et al. The oxidation mechanism of the antioxidant quercetin in nonaqueous media. Electrochimica Acta. 2011;56(21):7421–7. https://doi.org/10.1016/j.electacta.2011.04.121</mixed-citation></citation-alternatives></ref><ref id="cit11"><label>11</label><citation-alternatives><mixed-citation xml:lang="ru">Cherviakovsky EM, Bolibrukh DA, Baranovsky AV, Vlasova TM, Kurchenko VP, Gilep AA, Usanov SA. Oxidative modification of quercetin by hemeproteins. Biochem Biophys Res Commun. 2006;342(2):459–64. https://doi.org/10.1016/j.bbrc.2006.02.001</mixed-citation><mixed-citation xml:lang="en">Cherviakovsky EM, Bolibrukh DA, Baranovsky AV, Vlasova TM, Kurchenko VP, Gilep AA, Usanov SA. Oxidative modification of quercetin by hemeproteins. Biochem Biophys Res Commun. 2006;342(2):459–64. https://doi.org/10.1016/j.bbrc.2006.02.001</mixed-citation></citation-alternatives></ref><ref id="cit12"><label>12</label><citation-alternatives><mixed-citation xml:lang="ru">Takahama U, Hirota S, Nishioka T, Yoshitama K. Oxidation of Quercetin by Salivary Components II. Effects of Quercetin on Reactive Oxygen Metabolism by Salivary Polymorphonuclear Leukocytes. Food Science and Technology Research. 2002;8(3):276–80. https://doi.org/10.3136/fstr.8.276</mixed-citation><mixed-citation xml:lang="en">Takahama U, Hirota S, Nishioka T, Yoshitama K. Oxidation of Quercetin by Salivary Components II. Effects of Quercetin on Reactive Oxygen Metabolism by Salivary Polymorphonuclear Leukocytes. Food Science and Technology Research. 2002;8(3):276–80. https://doi.org/10.3136/fstr.8.276</mixed-citation></citation-alternatives></ref><ref id="cit13"><label>13</label><citation-alternatives><mixed-citation xml:lang="ru">Kubo I, Nihei K, Shimizu K. Oxidation products of quercetin catalyzed by mushroom tyrosinase. Bioorganic Medicinal Chemistry. 2004;12(20):5343–7. https://doi.org/10.1016/j.bmc.2004.07.050</mixed-citation><mixed-citation xml:lang="en">Kubo I, Nihei K, Shimizu K. Oxidation products of quercetin catalyzed by mushroom tyrosinase. Bioorganic Medicinal Chemistry. 2004;12(20):5343–7. https://doi.org/10.1016/j.bmc.2004.07.050</mixed-citation></citation-alternatives></ref><ref id="cit14"><label>14</label><citation-alternatives><mixed-citation xml:lang="ru">Momić T, Savić J, Vasić V. Oxidation of Quercetin by Myeloperoxidase. Research Letters in Physical Chemistry. 2009;2009:614362. https://doi.org/10.1155/2009/614362</mixed-citation><mixed-citation xml:lang="en">Momić T, Savić J, Vasić V. Oxidation of Quercetin by Myeloperoxidase. Research Letters in Physical Chemistry. 2009;2009:614362. https://doi.org/10.1155/2009/614362</mixed-citation></citation-alternatives></ref><ref id="cit15"><label>15</label><citation-alternatives><mixed-citation xml:lang="ru">Takahama U, Oniki T, Hirota S. Oxidation of Quercetin by Salivary Components. I. Salivary Peroxidase- Dependent Oxidation of Quercetin and Characterization of the Oxidation Products. FSTR. 2002;8(2):148–53. https://doi.org/10.1021/jf011697q</mixed-citation><mixed-citation xml:lang="en">Takahama U, Oniki T, Hirota S. Oxidation of Quercetin by Salivary Components. I. Salivary Peroxidase- Dependent Oxidation of Quercetin and Characterization of the Oxidation Products. FSTR. 2002;8(2):148–53. https://doi.org/10.1021/jf011697q</mixed-citation></citation-alternatives></ref><ref id="cit16"><label>16</label><citation-alternatives><mixed-citation xml:lang="ru">Зенкевич ИГ, Пушкарева ТИ. О моделировании механизма образования димерных продуктов окисления флафоноидов. Химия растительного сырья. 2018;(3):185–97. https://doi.org/10.14258/jcprm.2018033589 Zenkevich IG, Pushkareva TI. On modeling the mechanism of formation of dimeric oxidation products of flafonoids. Chemistry of plant raw materials. 2018;(3):185–97 (In Russian). https://doi.org/10.14258/jcprm.2018033589</mixed-citation><mixed-citation xml:lang="en">Зенкевич ИГ, Пушкарева ТИ. О моделировании механизма образования димерных продуктов окисления флафоноидов. Химия растительного сырья. 2018;(3):185–97. https://doi.org/10.14258/jcprm.2018033589 Zenkevich IG, Pushkareva TI. On modeling the mechanism of formation of dimeric oxidation products of flafonoids. Chemistry of plant raw materials. 2018;(3):185–97 (In Russian). https://doi.org/10.14258/jcprm.2018033589</mixed-citation></citation-alternatives></ref><ref id="cit17"><label>17</label><citation-alternatives><mixed-citation xml:lang="ru">Barnes JS., Schug KA. Oxidative Degradation of Quercetin with Hydrogen Peroxide Using Continuous- Flow Kinetic Electrospray–Ion Trap–Time-of-Flight Mass Spectrometry. J Agric Food Chem. 2014;62(19):4322–31. https://doi.org/10.1021/jf500619x</mixed-citation><mixed-citation xml:lang="en">Barnes JS., Schug KA. Oxidative Degradation of Quercetin with Hydrogen Peroxide Using Continuous- Flow Kinetic Electrospray–Ion Trap–Time-of-Flight Mass Spectrometry. J Agric Food Chem. 2014;62(19):4322–31. https://doi.org/10.1021/jf500619x</mixed-citation></citation-alternatives></ref><ref id="cit18"><label>18</label><citation-alternatives><mixed-citation xml:lang="ru">Zhou A, Sadik OA. Comparative Analysis of Quercetin Oxidation by Electrochemical, Enzymatic, Autoxidation, and Free Radical Generation Techniques: A Mechanistic Study. J Agric Food Chem. 2008;56(24):12081–91. https://doi.org/10.1021/jf802413v</mixed-citation><mixed-citation xml:lang="en">Zhou A, Sadik OA. Comparative Analysis of Quercetin Oxidation by Electrochemical, Enzymatic, Autoxidation, and Free Radical Generation Techniques: A Mechanistic Study. J Agric Food Chem. 2008;56(24):12081–91. https://doi.org/10.1021/jf802413v</mixed-citation></citation-alternatives></ref><ref id="cit19"><label>19</label><citation-alternatives><mixed-citation xml:lang="ru">Barnes JS, Foss FW Jr, Schug KA. Thermally Accelerated Oxidative Degradation of Quercetin Using Continuous Flow Kinetic Electrospray-Ion Trap-Time of Flight Mass Spectrometry. J Am Soc Mass Spectrom. 2013;24(10):1513–22. https://doi.org/10.1007/s13361-013-0698-6</mixed-citation><mixed-citation xml:lang="en">Barnes JS, Foss FW Jr, Schug KA. Thermally Accelerated Oxidative Degradation of Quercetin Using Continuous Flow Kinetic Electrospray-Ion Trap-Time of Flight Mass Spectrometry. J Am Soc Mass Spectrom. 2013;24(10):1513–22. https://doi.org/10.1007/s13361-013-0698-6</mixed-citation></citation-alternatives></ref><ref id="cit20"><label>20</label><citation-alternatives><mixed-citation xml:lang="ru">Krishnamachari V, Levine LH, Paré PW. Flavonoid oxidation by the radical generator AIBN: a unified mechanism for quercetin radical scavenging. J Agric Food Chem. 2002;50(15):4357–63. https://doi.org/10.1021/jf020045e</mixed-citation><mixed-citation xml:lang="en">Krishnamachari V, Levine LH, Paré PW. Flavonoid oxidation by the radical generator AIBN: a unified mechanism for quercetin radical scavenging. J Agric Food Chem. 2002;50(15):4357–63. https://doi.org/10.1021/jf020045e</mixed-citation></citation-alternatives></ref><ref id="cit21"><label>21</label><citation-alternatives><mixed-citation xml:lang="ru">Brown SB, Rajananda V, Holroyd JA, Evans EG. A study of the mechanism of quercetin oxygenation by 18O labelling. A comparison of the mechanism with that of haem degradation. Biochem J. 1982;205(1):239–44. https://doi.org/10.1042/bj2050239</mixed-citation><mixed-citation xml:lang="en">Brown SB, Rajananda V, Holroyd JA, Evans EG. A study of the mechanism of quercetin oxygenation by 18O labelling. A comparison of the mechanism with that of haem degradation. Biochem J. 1982;205(1):239–44. https://doi.org/10.1042/bj2050239</mixed-citation></citation-alternatives></ref><ref id="cit22"><label>22</label><citation-alternatives><mixed-citation xml:lang="ru">Miller E, Schreier P. Studies on flavonol degradation by peroxidase (donor: H2O2-oxidoreductase, EC 1.11.1.7): Part 1–Kaempferol. Food Chemistry. 1985;17(@):143–54. https://doi.org/10.1016/0308-8146(85)90111-6</mixed-citation><mixed-citation xml:lang="en">Miller E, Schreier P. Studies on flavonol degradation by peroxidase (donor: H2O2-oxidoreductase, EC 1.11.1.7): Part 1–Kaempferol. Food Chemistry. 1985;17(@):143–54. https://doi.org/10.1016/0308-8146(85)90111-6</mixed-citation></citation-alternatives></ref><ref id="cit23"><label>23</label><citation-alternatives><mixed-citation xml:lang="ru">Ramos FA, Takaishi Y, Shirotori M, Kawaguchi Y, Tsuchiya K, Shibata H, et al. Antibacterial and antioxidant activities of quercetin oxidation products from yellow onion (Allium cepa) skin. J Agric Food Chem. 2006;54(10):3551–7. https://doi.org/10.1021/jf060251c</mixed-citation><mixed-citation xml:lang="en">Ramos FA, Takaishi Y, Shirotori M, Kawaguchi Y, Tsuchiya K, Shibata H, et al. Antibacterial and antioxidant activities of quercetin oxidation products from yellow onion (Allium cepa) skin. J Agric Food Chem. 2006;54(10):3551–7. https://doi.org/10.1021/jf060251c</mixed-citation></citation-alternatives></ref></ref-list><fn-group><fn fn-type="conflict"><p>The authors declare that there are no conflicts of interest present.</p></fn></fn-group></back></article>
