vestibИзвестия Национальной академии наук Беларуси. Серия биологических наукProceedings of the National Academy of Sciences of Belarus, Biological Series1029-89402524-230XThe Republican Unitary Enterprise Publishing House "Belaruskaya Navuka"10.29235/1029-8940-2018-63-4-500-512vestib-401Research ArticleСтатьиКвантово-химическое моделирование электронной структуры кверцетина и ингибирование кверцетином и комплексом кверцетин–гидроксипропил-β-циклодекстрин перекисного окисления липидов в митохондриях и эритроцитах крысQuantum-chemical modeling of the electronic structure of quercetin and inhibition by quercetin and quercetin–hydroxypropyl-β-cyclodextrin complex of lipid peroxidation in mitochondria and red blood cells of ratsВейкоА. Г.VeikoA. G.

Вейко Артем Геннадьевич – аспирант.

ул. Ожешко, 22, 230023, Гродно.

Artem G. Veiko – Postgraduate student.

22,  Ozheshko Str.,  230023, Grodno.

Wei93@yandex.ruИльичТ. В.IlyichT. V.

Ильич  Татьяна  Викторовна  – аспирант.

ул.  Ожешко,  22, 230023, Гродно.

Tatsiana V. Ilyich – Postgraduate student.

22, Ozheshko Str., 230023, Grodno.

Tatyana-luchic@yandex.ruЛапшинаЕ. А.LapshinaE. A.

Лапшина Елена Алексеевна – кандидат биологических наук, доцент.

ул. Ожешко, 22, 230023, Гродно.

Elena A. Lapshina – Ph. D. (Biol.), Assistant professor.

22, Ozheshko Str., 230023, Grodno.

Lapshina_EA@grsu.byБукоВ. У.BukoV. U.

Буко Вячеслав Ульянович – доктор биологических наук, профессор, заведующий отделом.

БЛК, 50, 230030, Гродно.

Vyacheslav U. Buko – D. Sc. (Biol.), Professor, Head of the Department.

50, BLK, 230030, Grodno.

Buko@bioch.basnet.byЗаводникИ. Б.ZavodnikI. B.

Заводник Илья Борисович – доктор биологических наук, профессор, заведующий  кафедрой.

ул. Ожешко, 22, 230023, Гродно.

Ilya B. Zavodnik – D. Sc. (Biol.), Professor, Head of the Department.

22, Ozheshko Str., 230023, Grodno.

zavodnik_il@mail.ruГродненский государственный университет им. Янки КупалыYanka Kupala Grodno State UniversityИнститут биохимии биологически активных соединений НАН БеларусиInstitute of Biochemistry of Biologically Active Compounds of the National Academy of Sciences of Belarus201830102018634500512Copyright © Вейко А.Г., Ильич Т.В., Лапшина Е.А., Буко В.У., Заводник И.Б., 20182018Вейко А.Г., Ильич Т.В., Лапшина Е.А., Буко В.У., Заводник И.Б.Veiko A.G., Ilyich T.V., Lapshina E.A., Buko V.U., Zavodnik I.B.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://vestibio.belnauka.by/jour/article/view/401

Кверцетин (3,3ʹ,4ʹ,5,7-пeнтагидроксифлавон) – один из наиболее распространенных  и изученных флавоноидов, который обладает доказанной антиоксидантной активностью  и демонстрирует выраженный терапевтический потенциал при целом ряде патологических состояний.

Изучена электронная структура молекулы кверцетина и его семихинон-радикала, оценена антиоксидантная активность кверцетина и его комплекса включения  с гидроксипропил-β-циклодекстрином. Генерирование карт распределения электронной плотности в молекуле кверцетина и семихинон-радикала кверцетина показало, что активные электронные орбитали (HOMO и LUMO) кверцетина и его семихинон-радикала делокализованы по всем фенольным кольцам, что в случае радикала обеспечивает его определенную стабилизацию. Установлено также, что кверцетин эффективно предотвращает перекисное окисление липидов мембран эритроцитов и митохондрий, индуцируемое  терт-бутилгидропероксидом: IC50 = 31 ± 4 μМ для митохондрий и IC50 = 25 ± 3 μМ для эритроцитов. Эффективность ингибирования кверцетином окисления восстановленного глутатиона эритроцитов и митохондрий значительно ниже, что отражает липофильность полифенола. Кроме того, показано, что кверцетин предотвращает лизис эритроцитов гипохлорной кислотой: IC50 = 3 ± 0,5 μМ. Комплекс кверцетин–гидроксипропил-β-циклодекстрин оказался более эффективен в качестве ингибитора процессов перекисного окисления мембранных липидов и окисления глутатиона.

Quercetin (3,3ʹ,4ʹ,5,7-pentahydroxyflavon), one of the most common and studied flavonoids, possesses the antioxidant activity  and demonstrates the pronounced therapeutic potential under a number of pathological conditions. The purpose of this work is to estimate the electronic structure of the quercetin and its semi-quinone radical molecules and to compare the antioxidant activities of quercetin and its inclusion complex with hydroxypropyl-β-cyclodextrin. Generation of maps of the electron density distribution in quercetin and quercetin semi-quinone radical molecules showed that the active electron orbitals (HOMO and LUMO) are delocalized over all phenolic rings providing the radical stabilization. We have showed that quercetin prevents the tert-butyl hydroperoxide-induced lipid peroxidation of erythrocytes (IC50 = 25 ± 3 μM) and mitochondrial membranes (IC50 = 31 ± 4 μM). The efficiency of quercetin inhibition the reduced glutathione oxidation in erythrocytes and mitochondria is much lower reflecting the lipophilicity  of polyphenol. Quercetin also prevented the hypochlorite-induced lysis of red blood cells (IC50 = 3 ± 0.5 μM). Our data revealed that the quercetin-hydroxypropyl-β-cyclodex-trin complex is more effective inhibitor of the membrane lipids peroxidation and glutathione oxidation processes.

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The authors declare that there are no conflicts of interest present.