Chemoenzymatic Preparation and Biophysical Properties of Sulfated Quercetin Metabolites

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) wer...
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Autor*in:	Kateřina Valentová [verfasserIn] Kristýna Káňová [verfasserIn] Florent Di Meo [verfasserIn] Helena Pelantová [verfasserIn] Christopher Steven Chambers [verfasserIn] Lenka Rydlová [verfasserIn] Lucie Petrásková [verfasserIn] Alena Křenková [verfasserIn] Josef Cvačka [verfasserIn] Patrick Trouillas [verfasserIn] Vladimír Křen [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2017

Schlagwörter:	quercetin sulfotransferase sulfates metabolites antiradical activity lipid peroxidation density functional theory molecular dynamics

Übergeordnetes Werk:	In: International Journal of Molecular Sciences - MDPI AG, 2003, 18(2017), 11, p 2231
Übergeordnetes Werk:	volume:18 ; year:2017 ; number:11, p 2231

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.3390/ijms18112231

Katalog-ID:	DOAJ036670839

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allfields	10.3390/ijms18112231 doi (DE-627)DOAJ036670839 (DE-599)DOAJ2ebb7d28fee849968190bd7fde992a58 DE-627 ger DE-627 rakwb eng QH301-705.5 QD1-999 Kateřina Valentová verfasserin aut Chemoenzymatic Preparation and Biophysical Properties of Sulfated Quercetin Metabolites 2017 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier 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. quercetin sulfotransferase sulfates metabolites antiradical activity lipid peroxidation density functional theory molecular dynamics Biology (General) Chemistry Kristýna Káňová verfasserin aut Florent Di Meo verfasserin aut Helena Pelantová verfasserin aut Christopher Steven Chambers verfasserin aut Lenka Rydlová verfasserin aut Lucie Petrásková verfasserin aut Alena Křenková verfasserin aut Josef Cvačka verfasserin aut Patrick Trouillas verfasserin aut Vladimír Křen verfasserin aut In International Journal of Molecular Sciences MDPI AG, 2003 18(2017), 11, p 2231 (DE-627)316340715 (DE-600)2019364-6 14220067 nnns volume:18 year:2017 number:11, p 2231 https://doi.org/10.3390/ijms18112231 kostenfrei https://doaj.org/article/2ebb7d28fee849968190bd7fde992a58 kostenfrei https://www.mdpi.com/1422-0067/18/11/2231 kostenfrei https://doaj.org/toc/1422-0067 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 18 2017 11, p 2231
spelling	10.3390/ijms18112231 doi (DE-627)DOAJ036670839 (DE-599)DOAJ2ebb7d28fee849968190bd7fde992a58 DE-627 ger DE-627 rakwb eng QH301-705.5 QD1-999 Kateřina Valentová verfasserin aut Chemoenzymatic Preparation and Biophysical Properties of Sulfated Quercetin Metabolites 2017 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier 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. quercetin sulfotransferase sulfates metabolites antiradical activity lipid peroxidation density functional theory molecular dynamics Biology (General) Chemistry Kristýna Káňová verfasserin aut Florent Di Meo verfasserin aut Helena Pelantová verfasserin aut Christopher Steven Chambers verfasserin aut Lenka Rydlová verfasserin aut Lucie Petrásková verfasserin aut Alena Křenková verfasserin aut Josef Cvačka verfasserin aut Patrick Trouillas verfasserin aut Vladimír Křen verfasserin aut In International Journal of Molecular Sciences MDPI AG, 2003 18(2017), 11, p 2231 (DE-627)316340715 (DE-600)2019364-6 14220067 nnns volume:18 year:2017 number:11, p 2231 https://doi.org/10.3390/ijms18112231 kostenfrei https://doaj.org/article/2ebb7d28fee849968190bd7fde992a58 kostenfrei https://www.mdpi.com/1422-0067/18/11/2231 kostenfrei https://doaj.org/toc/1422-0067 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 18 2017 11, p 2231
allfields_unstemmed	10.3390/ijms18112231 doi (DE-627)DOAJ036670839 (DE-599)DOAJ2ebb7d28fee849968190bd7fde992a58 DE-627 ger DE-627 rakwb eng QH301-705.5 QD1-999 Kateřina Valentová verfasserin aut Chemoenzymatic Preparation and Biophysical Properties of Sulfated Quercetin Metabolites 2017 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier 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. quercetin sulfotransferase sulfates metabolites antiradical activity lipid peroxidation density functional theory molecular dynamics Biology (General) Chemistry Kristýna Káňová verfasserin aut Florent Di Meo verfasserin aut Helena Pelantová verfasserin aut Christopher Steven Chambers verfasserin aut Lenka Rydlová verfasserin aut Lucie Petrásková verfasserin aut Alena Křenková verfasserin aut Josef Cvačka verfasserin aut Patrick Trouillas verfasserin aut Vladimír Křen verfasserin aut In International Journal of Molecular Sciences MDPI AG, 2003 18(2017), 11, p 2231 (DE-627)316340715 (DE-600)2019364-6 14220067 nnns volume:18 year:2017 number:11, p 2231 https://doi.org/10.3390/ijms18112231 kostenfrei https://doaj.org/article/2ebb7d28fee849968190bd7fde992a58 kostenfrei https://www.mdpi.com/1422-0067/18/11/2231 kostenfrei https://doaj.org/toc/1422-0067 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 18 2017 11, p 2231
allfieldsGer	10.3390/ijms18112231 doi (DE-627)DOAJ036670839 (DE-599)DOAJ2ebb7d28fee849968190bd7fde992a58 DE-627 ger DE-627 rakwb eng QH301-705.5 QD1-999 Kateřina Valentová verfasserin aut Chemoenzymatic Preparation and Biophysical Properties of Sulfated Quercetin Metabolites 2017 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier 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. quercetin sulfotransferase sulfates metabolites antiradical activity lipid peroxidation density functional theory molecular dynamics Biology (General) Chemistry Kristýna Káňová verfasserin aut Florent Di Meo verfasserin aut Helena Pelantová verfasserin aut Christopher Steven Chambers verfasserin aut Lenka Rydlová verfasserin aut Lucie Petrásková verfasserin aut Alena Křenková verfasserin aut Josef Cvačka verfasserin aut Patrick Trouillas verfasserin aut Vladimír Křen verfasserin aut In International Journal of Molecular Sciences MDPI AG, 2003 18(2017), 11, p 2231 (DE-627)316340715 (DE-600)2019364-6 14220067 nnns volume:18 year:2017 number:11, p 2231 https://doi.org/10.3390/ijms18112231 kostenfrei https://doaj.org/article/2ebb7d28fee849968190bd7fde992a58 kostenfrei https://www.mdpi.com/1422-0067/18/11/2231 kostenfrei https://doaj.org/toc/1422-0067 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 18 2017 11, p 2231
allfieldsSound	10.3390/ijms18112231 doi (DE-627)DOAJ036670839 (DE-599)DOAJ2ebb7d28fee849968190bd7fde992a58 DE-627 ger DE-627 rakwb eng QH301-705.5 QD1-999 Kateřina Valentová verfasserin aut Chemoenzymatic Preparation and Biophysical Properties of Sulfated Quercetin Metabolites 2017 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier 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. quercetin sulfotransferase sulfates metabolites antiradical activity lipid peroxidation density functional theory molecular dynamics Biology (General) Chemistry Kristýna Káňová verfasserin aut Florent Di Meo verfasserin aut Helena Pelantová verfasserin aut Christopher Steven Chambers verfasserin aut Lenka Rydlová verfasserin aut Lucie Petrásková verfasserin aut Alena Křenková verfasserin aut Josef Cvačka verfasserin aut Patrick Trouillas verfasserin aut Vladimír Křen verfasserin aut In International Journal of Molecular Sciences MDPI AG, 2003 18(2017), 11, p 2231 (DE-627)316340715 (DE-600)2019364-6 14220067 nnns volume:18 year:2017 number:11, p 2231 https://doi.org/10.3390/ijms18112231 kostenfrei https://doaj.org/article/2ebb7d28fee849968190bd7fde992a58 kostenfrei https://www.mdpi.com/1422-0067/18/11/2231 kostenfrei https://doaj.org/toc/1422-0067 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_224 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 18 2017 11, p 2231
language	English
source	In International Journal of Molecular Sciences 18(2017), 11, p 2231 volume:18 year:2017 number:11, p 2231
sourceStr	In International Journal of Molecular Sciences 18(2017), 11, p 2231 volume:18 year:2017 number:11, p 2231
format_phy_str_mv	Article
institution	findex.gbv.de
topic_facet	quercetin sulfotransferase sulfates metabolites antiradical activity lipid peroxidation density functional theory molecular dynamics Biology (General) Chemistry
isfreeaccess_bool	true
container_title	International Journal of Molecular Sciences
authorswithroles_txt_mv	Kateřina Valentová @@aut@@ Kristýna Káňová @@aut@@ Florent Di Meo @@aut@@ Helena Pelantová @@aut@@ Christopher Steven Chambers @@aut@@ Lenka Rydlová @@aut@@ Lucie Petrásková @@aut@@ Alena Křenková @@aut@@ Josef Cvačka @@aut@@ Patrick Trouillas @@aut@@ Vladimír Křen @@aut@@
publishDateDaySort_date	2017-01-01T00:00:00Z
hierarchy_top_id	316340715
id	DOAJ036670839
language_de	englisch
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callnumber-first	Q - Science
author	Kateřina Valentová
spellingShingle	Kateřina Valentová misc QH301-705.5 misc QD1-999 misc quercetin misc sulfotransferase misc sulfates misc metabolites misc antiradical activity misc lipid peroxidation misc density functional theory misc molecular dynamics misc Biology (General) misc Chemistry Chemoenzymatic Preparation and Biophysical Properties of Sulfated Quercetin Metabolites
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topic_title	QH301-705.5 QD1-999 Chemoenzymatic Preparation and Biophysical Properties of Sulfated Quercetin Metabolites quercetin sulfotransferase sulfates metabolites antiradical activity lipid peroxidation density functional theory molecular dynamics
topic	misc QH301-705.5 misc QD1-999 misc quercetin misc sulfotransferase misc sulfates misc metabolites misc antiradical activity misc lipid peroxidation misc density functional theory misc molecular dynamics misc Biology (General) misc Chemistry
topic_unstemmed	misc QH301-705.5 misc QD1-999 misc quercetin misc sulfotransferase misc sulfates misc metabolites misc antiradical activity misc lipid peroxidation misc density functional theory misc molecular dynamics misc Biology (General) misc Chemistry
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title	Chemoenzymatic Preparation and Biophysical Properties of Sulfated Quercetin Metabolites
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title_full	Chemoenzymatic Preparation and Biophysical Properties of Sulfated Quercetin Metabolites
author_sort	Kateřina Valentová
journal	International Journal of Molecular Sciences
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author_browse	Kateřina Valentová Kristýna Káňová Florent Di Meo Helena Pelantová Christopher Steven Chambers Lenka Rydlová Lucie Petrásková Alena Křenková Josef Cvačka Patrick Trouillas Vladimír Křen
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author-letter	Kateřina Valentová
doi_str_mv	10.3390/ijms18112231
author2-role	verfasserin
title_sort	chemoenzymatic preparation and biophysical properties of sulfated quercetin metabolites
callnumber	QH301-705.5
title_auth	Chemoenzymatic Preparation and Biophysical Properties of Sulfated Quercetin Metabolites
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.
abstractGer	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.
abstract_unstemmed	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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container_issue	11, p 2231
title_short	Chemoenzymatic Preparation and Biophysical Properties of Sulfated Quercetin Metabolites
url	https://doi.org/10.3390/ijms18112231 https://doaj.org/article/2ebb7d28fee849968190bd7fde992a58 https://www.mdpi.com/1422-0067/18/11/2231 https://doaj.org/toc/1422-0067
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author2	Kristýna Káňová Florent Di Meo Helena Pelantová Christopher Steven Chambers Lenka Rydlová Lucie Petrásková Alena Křenková Josef Cvačka Patrick Trouillas Vladimír Křen
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Chemoenzymatic Preparation and Biophysical Properties of Sulfated Quercetin Metabolites

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