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Int. J. Mol. Sci. 2017, 18(11), 2231; https://doi.org/10.3390/ijms18112231

Chemoenzymatic Preparation and Biophysical Properties of Sulfated Quercetin Metabolites

1
Institute of Microbiology of the Czech Academy of Sciences, Vídeňská 1083, CZ-14220 Prague, Czech Republic
2
INSERM U850, Univ. Limoges, School of Pharmacy, 2 rue du Docteur Marcland, F-87025 Limoges, France
3
Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Flemingovo nám. 2, CZ-16610 Prague, Czech Republic
4
Regional Centre of Advanced Technologies and Materials, Department of Physical Chemistry, Faculty of Science, Palacký University, tř. 17. listopadu 12, CZ-77146 Olomouc, Czech Republic
*
Authors to whom correspondence should be addressed.
Received: 12 September 2017 / Revised: 2 October 2017 / Accepted: 20 October 2017 / Published: 25 October 2017
(This article belongs to the Special Issue Bioactive Phenolics and Polyphenols 2018)
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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. View Full-Text
Keywords: quercetin; sulfotransferase; sulfates; metabolites; antiradical activity; lipid peroxidation; density functional theory; molecular dynamics quercetin; sulfotransferase; sulfates; metabolites; antiradical activity; lipid peroxidation; density functional theory; molecular dynamics
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Valentová, K.; Káňová, K.; Di Meo, F.; Pelantová, H.; Chambers, C.S.; Rydlová, L.; Petrásková, L.; Křenková, A.; Cvačka, J.; Trouillas, P.; Křen, V. Chemoenzymatic Preparation and Biophysical Properties of Sulfated Quercetin Metabolites. Int. J. Mol. Sci. 2017, 18, 2231.

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