Chemoenzymatic Preparation and Biophysical Properties of Sulfated Quercetin Metabolites

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F17%3A00483673" target="_blank" >RIV/61388963:_____/17:00483673 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61388971:_____/17:00483673 RIV/61989592:15310/17:73584605

Výsledek na webu

<a href="http://dx.doi.org/10.3390/ijms18112231" target="_blank" >http://dx.doi.org/10.3390/ijms18112231</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3390/ijms18112231" target="_blank" >10.3390/ijms18112231</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Chemoenzymatic Preparation and Biophysical Properties of Sulfated Quercetin Metabolites

Popis výsledku v původním jazyce

Sulfated quercetin derivatives are important authentic standards for metabolic studies. Quercetin-3-O-sulfate, quercetin-4'-O-sulfate, and quercetin-3'-O-sulfate as well as quercetin-di-O-sulfate mixture (quercetin-7',3'-di-O-sulfate, quercetin-7',4'-di-O-sulfate, and quercetin-3',4'-di-O-sulfate) were synthetized by arylsulfotransferase from Desulfitobacterium hafniense. Purified monosulfates and disulfates were fully characterized using MS and NMR and tested for their 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2',2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS(+)) and N,N-dimethyl-p-phenylenediamine (DMPD) radical scavenging, Folin-Ciocalteau reduction (FCR), ferric reducing antioxidant power (FRAP), and anti-lipoperoxidant activities in rat liver microsomes damaged by tert-butylhydroperoxide. Although, as expected, the sulfated metabolites were usually less active than quercetin, they remained still effective antiradical and reducing agents. Quercetin-3'-O-sulfate was more efficient than quercetin-4'-O-sulfate in DPPH and FCR assays. In contrast, quercetin-4'-O-sulfate was the best ferric reductant and lipoperoxidation inhibitor. The capacity to scavenge ABTS(+center dot) and DMPD was comparable for all substances, except for disulfates, which were the most efficient. Quantum calculations and molecular dynamics simulations on membrane models supported rationalization of free radical scavenging and lipid peroxidation inhibition. These results clearly showed that individual metabolites of food bioactives can markedly differ in their biological activity. Therefore, a systematic and thorough investigation of all bioavailable metabolites with respect to native compounds is needed when evaluating food health benefits.

Název v anglickém jazyce

Chemoenzymatic Preparation and Biophysical Properties of Sulfated Quercetin Metabolites

Popis výsledku anglicky

Sulfated quercetin derivatives are important authentic standards for metabolic studies. Quercetin-3-O-sulfate, quercetin-4'-O-sulfate, and quercetin-3'-O-sulfate as well as quercetin-di-O-sulfate mixture (quercetin-7',3'-di-O-sulfate, quercetin-7',4'-di-O-sulfate, and quercetin-3',4'-di-O-sulfate) were synthetized by arylsulfotransferase from Desulfitobacterium hafniense. Purified monosulfates and disulfates were fully characterized using MS and NMR and tested for their 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2',2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS(+)) and N,N-dimethyl-p-phenylenediamine (DMPD) radical scavenging, Folin-Ciocalteau reduction (FCR), ferric reducing antioxidant power (FRAP), and anti-lipoperoxidant activities in rat liver microsomes damaged by tert-butylhydroperoxide. Although, as expected, the sulfated metabolites were usually less active than quercetin, they remained still effective antiradical and reducing agents. Quercetin-3'-O-sulfate was more efficient than quercetin-4'-O-sulfate in DPPH and FCR assays. In contrast, quercetin-4'-O-sulfate was the best ferric reductant and lipoperoxidation inhibitor. The capacity to scavenge ABTS(+center dot) and DMPD was comparable for all substances, except for disulfates, which were the most efficient. Quantum calculations and molecular dynamics simulations on membrane models supported rationalization of free radical scavenging and lipid peroxidation inhibition. These results clearly showed that individual metabolites of food bioactives can markedly differ in their biological activity. Therefore, a systematic and thorough investigation of all bioavailable metabolites with respect to native compounds is needed when evaluating food health benefits.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10608 - Biochemistry and molecular biology

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)

Rok uplatnění

2017

Kód důvěrnosti údajů

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

Název periodika

International Journal of Molecular Sciences

ISSN

1422-0067

e-ISSN

—

Svazek periodika

18

Číslo periodika v rámci svazku

11

Stát vydavatele periodika

CH - Švýcarská konfederace

Počet stran výsledku

17

Strana od-do

—

Kód UT WoS článku

000416811300005

EID výsledku v databázi Scopus

2-s2.0-85032581122