Chemoenzymatic Preparation and Biophysical Properties of Sulfated Quercetin Metabolites
The result's identifiers
Result code in 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>
Alternative codes found
RIV/61388971:_____/17:00483673 RIV/61989592:15310/17:73584605
Result on the web
<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>
Alternative languages
Result language
angličtina
Original language name
Chemoenzymatic Preparation and Biophysical Properties of Sulfated Quercetin Metabolites
Original language description
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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10608 - Biochemistry and molecular biology
Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2017
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
International Journal of Molecular Sciences
ISSN
1422-0067
e-ISSN
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Volume of the periodical
18
Issue of the periodical within the volume
11
Country of publishing house
CH - SWITZERLAND
Number of pages
17
Pages from-to
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UT code for WoS article
000416811300005
EID of the result in the Scopus database
2-s2.0-85032581122