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| Content Provider | MDPI |
|---|---|
| Author | Valentová, Kateřina Káňová, Kristýna Di Meo, Florent Pelantová, Helena Chambers, Christopher Rydlová, Lenka Petrásková, Lucie Křenková, Alena Cvačka, Josef Trouillas, Patrick Křen, Vladimír |
| Abstract | 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+• 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. |
| File Size | 2176000 |
| File Format | |
| e-ISSN | 14220067 |
| DOI | 10.3390/ijms18112231 |
| Journal | International Journal of Molecular Sciences |
| Issue Number | 11 |
| Volume Number | 18 |
| Language | English |
| Publisher Date | 2017-10-25 |
| Access Restriction | Open |
| Subject Keyword | quercetin sulfotransferase sulfates metabolites antiradical activity lipid peroxidation density functional theory molecular dynamics |
| Content Type | Text |
| Resource Type | Article |
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