Antioxidant, metal-binding and DNA-damaging properties of flavonolignans: A joint experimental and computational highlight based on 7-O-galloylsilybin

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F13%3A33144010" target="_blank" >RIV/61989592:15310/13:33144010 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61388971:_____/13:00395322 RIV/61989592:15110/13:33144010

Výsledek na webu

<a href="http://dx.doi.org/10.1016/j.cbi.2013.07.006" target="_blank" >http://dx.doi.org/10.1016/j.cbi.2013.07.006</a>

DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

Antioxidant, metal-binding and DNA-damaging properties of flavonolignans: A joint experimental and computational highlight based on 7-O-galloylsilybin

Popis výsledku v původním jazyce

Besides the well-known chemoprotective effects of polyphenols, their prooxidant activities via interac- tions with biomacromolecules as DNA and proteins are of the utmost importance. Current research focuses not only on natural polyphenols but also on synthetically prepared analogs with promising bio-logical activities. In the present study, the antioxidant and prooxidant properties of a semi-synthetic flavonolignan 7-O-galloylsilybin (7-GSB) are described. The presence of the galloyl moiety significantly enhances the antioxidant capacity of 7-GSB compared to that of silybin (SB). These findings were supported by electrochemistry, DPPH (2,2-diphenyl-1-picrylhydrazyl) scavenging activity, total antioxidant capacity (CL-TAC) and DFT (density functional theory) calculations. A three-step oxidation mechanism of 7-GSB is proposed at pH 7.4, in which the galloyl moiety is first oxidized at Ep,1= +0.20 V (vs. Ag/AgCl 3M KCl) followed by oxidation of the 20-OH (Ep,2 = +0.55 V) and most probabl

Název v anglickém jazyce

Antioxidant, metal-binding and DNA-damaging properties of flavonolignans: A joint experimental and computational highlight based on 7-O-galloylsilybin

Popis výsledku anglicky

Besides the well-known chemoprotective effects of polyphenols, their prooxidant activities via interac- tions with biomacromolecules as DNA and proteins are of the utmost importance. Current research focuses not only on natural polyphenols but also on synthetically prepared analogs with promising bio-logical activities. In the present study, the antioxidant and prooxidant properties of a semi-synthetic flavonolignan 7-O-galloylsilybin (7-GSB) are described. The presence of the galloyl moiety significantly enhances the antioxidant capacity of 7-GSB compared to that of silybin (SB). These findings were supported by electrochemistry, DPPH (2,2-diphenyl-1-picrylhydrazyl) scavenging activity, total antioxidant capacity (CL-TAC) and DFT (density functional theory) calculations. A three-step oxidation mechanism of 7-GSB is proposed at pH 7.4, in which the galloyl moiety is first oxidized at Ep,1= +0.20 V (vs. Ag/AgCl 3M KCl) followed by oxidation of the 20-OH (Ep,2 = +0.55 V) and most probabl

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CE - Biochemie

OECD FORD obor

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Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2013

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Chemico-Biological Interactions

ISSN

0009-2797

e-ISSN

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Svazek periodika

205

Číslo periodika v rámci svazku

3

Stát vydavatele periodika

IE - Irsko

Počet stran výsledku

8

Strana od-do

173-180

Kód UT WoS článku

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EID výsledku v databázi Scopus

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