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.

INSERM U850 Univ Limoges School of Pharmacy 2 rue du Docteur Marcland F 87025 Limoges France

INSERM U850 Univ Limoges School of Pharmacy 2 rue du Docteur Marcland F 87025 Limoges France 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

Institute of Microbiology of the Czech Academy of Sciences Vídeňská 1083 CZ 14220 Prague Czech Republic

Institute of Organic Chemistry and Biochemistry Czech Academy of Sciences Flemingovo nám 2 CZ 16610 Prague Czech Republic

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$a Valentová, Kateřina $u Institute of Microbiology of the Czech Academy of Sciences, Vídeňská 1083, CZ-14220 Prague, Czech Republic. kata.valentova@email.cz.

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$a Chemoenzymatic Preparation and Biophysical Properties of Sulfated Quercetin Metabolites / $c K. Valentová, K. Káňová, F. Di Meo, H. Pelantová, CS. Chambers, L. Rydlová, L. Petrásková, A. Křenková, J. Cvačka, P. Trouillas, V. Křen,

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$a 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.

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$a Káňová, Kristýna $u Institute of Microbiology of the Czech Academy of Sciences, Vídeňská 1083, CZ-14220 Prague, Czech Republic. astriik@gmail.com.

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$a Di Meo, Florent $u INSERM U850, Univ. Limoges, School of Pharmacy, 2 rue du Docteur Marcland, F-87025 Limoges, France. florent.di-meo@unilim.fr.

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$a Pelantová, Helena $u Institute of Microbiology of the Czech Academy of Sciences, Vídeňská 1083, CZ-14220 Prague, Czech Republic. pelantova@biomed.cas.cz.

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$a Chambers, Christopher Steven $u Institute of Microbiology of the Czech Academy of Sciences, Vídeňská 1083, CZ-14220 Prague, Czech Republic. christopher.chambers@biomed.cas.cz.

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$a Rydlová, Lenka $u Institute of Microbiology of the Czech Academy of Sciences, Vídeňská 1083, CZ-14220 Prague, Czech Republic. rydlova.l@email.cz.

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$a Petrásková, Lucie $u Institute of Microbiology of the Czech Academy of Sciences, Vídeňská 1083, CZ-14220 Prague, Czech Republic. petraskova@biomed.cas.cz.

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$a Křenková, Alena $u Institute of Microbiology of the Czech Academy of Sciences, Vídeňská 1083, CZ-14220 Prague, Czech Republic. alenka.petrickova@gmail.com.

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$a Cvačka, Josef $u Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences, Flemingovo nám. 2, CZ-16610 Prague, Czech Republic. cvacka@uochb.cas.cz.

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$a Trouillas, Patrick $u INSERM U850, Univ. Limoges, School of Pharmacy, 2 rue du Docteur Marcland, F-87025 Limoges, France. patrick.trouillas@unilim.fr. 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. patrick.trouillas@unilim.fr.

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$a Křen, Vladimír $u Institute of Microbiology of the Czech Academy of Sciences, Vídeňská 1083, CZ-14220 Prague, Czech Republic. kren@biomed.cas.cz.

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