Sulfated Metabolites of Flavonolignans and 2,3-Dehydroflavonolignans: Preparation and Properties

Silymarin, an extract from milk thistle (Silybum marianum) fruits, is consumed in various food supplements. The metabolism of silymarin flavonolignans in mammals is complex, the exact structure of their metabolites still remains partly unclear and standards are not commercially available. This work...
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Autor*in:	Kateřina Valentová [verfasserIn] Kateřina Purchartová [verfasserIn] Lenka Rydlová [verfasserIn] Lenka Roubalová [verfasserIn] David Biedermann [verfasserIn] Lucie Petrásková [verfasserIn] Alena Křenková [verfasserIn] Helena Pelantová [verfasserIn] Veronika Holečková-Moravcová [verfasserIn] Eva Tesařová [verfasserIn] Josef Cvačka [verfasserIn] Jiří Vrba [verfasserIn] Jitka Ulrichová [verfasserIn] Vladimír Křen [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2018

Schlagwörter:	Silybum marianum sulfate sulfotransferase biotransformation metabolites activity

Übergeordnetes Werk:	In: International Journal of Molecular Sciences - MDPI AG, 2003, 19(2018), 8, p 2349
Übergeordnetes Werk:	volume:19 ; year:2018 ; number:8, p 2349

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc

DOI / URN:	10.3390/ijms19082349

Katalog-ID:	DOAJ01263610X

Internformat


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allfields	10.3390/ijms19082349 doi (DE-627)DOAJ01263610X (DE-599)DOAJ8946e26fc003456193d988433904ee1a DE-627 ger DE-627 rakwb eng QH301-705.5 QD1-999 Kateřina Valentová verfasserin aut Sulfated Metabolites of Flavonolignans and 2,3-Dehydroflavonolignans: Preparation and Properties 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Silymarin, an extract from milk thistle (Silybum marianum) fruits, is consumed in various food supplements. The metabolism of silymarin flavonolignans in mammals is complex, the exact structure of their metabolites still remains partly unclear and standards are not commercially available. This work is focused on the preparation of sulfated metabolites of silymarin flavonolignans. Sulfated flavonolignans were prepared using aryl sulfotransferase from Desulfitobacterium hafniense and p-nitrophenyl sulfate as a sulfate donor and characterized by high-resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR). 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; ferric (FRAP) and Folin–Ciocalteu reagent (FCR) reducing activity; anti-lipoperoxidant potential; and effect on the nuclear erythroid 2-related factor 2 (Nrf2) signaling pathway were examined. Pure silybin A 20-O-sulfate, silybin B 20-O-sulfate, 2,3-dehydrosilybin-20-O-sulfate, 2,3-dehydrosilybin-7,20-di-O-sulfate, silychristin-19-O-sulfate, 2,3-dehydrosilychristin-19-O-sulfate, and silydianin-19-O-sulfate were prepared and fully characterized. Sulfated 2,3-dehydroderivatives were more active in FCR and FRAP assays than the parent compounds, and remaining sulfates were less active chemoprotectants. The sulfated flavonolignans obtained can be now used as authentic standards for in vivo metabolic experiments and for further research on their biological activity. Silybum marianum sulfate sulfotransferase biotransformation metabolites activity Biology (General) Chemistry Kateřina Purchartová verfasserin aut Lenka Rydlová verfasserin aut Lenka Roubalová verfasserin aut David Biedermann verfasserin aut Lucie Petrásková verfasserin aut Alena Křenková verfasserin aut Helena Pelantová verfasserin aut Veronika Holečková-Moravcová verfasserin aut Eva Tesařová verfasserin aut Josef Cvačka verfasserin aut Jiří Vrba verfasserin aut Jitka Ulrichová verfasserin aut Vladimír Křen verfasserin aut In International Journal of Molecular Sciences MDPI AG, 2003 19(2018), 8, p 2349 (DE-627)316340715 (DE-600)2019364-6 14220067 nnns volume:19 year:2018 number:8, p 2349 https://doi.org/10.3390/ijms19082349 kostenfrei https://doaj.org/article/8946e26fc003456193d988433904ee1a kostenfrei http://www.mdpi.com/1422-0067/19/8/2349 kostenfrei https://doaj.org/toc/1422-0067 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ 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 19 2018 8, p 2349
spelling	10.3390/ijms19082349 doi (DE-627)DOAJ01263610X (DE-599)DOAJ8946e26fc003456193d988433904ee1a DE-627 ger DE-627 rakwb eng QH301-705.5 QD1-999 Kateřina Valentová verfasserin aut Sulfated Metabolites of Flavonolignans and 2,3-Dehydroflavonolignans: Preparation and Properties 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Silymarin, an extract from milk thistle (Silybum marianum) fruits, is consumed in various food supplements. The metabolism of silymarin flavonolignans in mammals is complex, the exact structure of their metabolites still remains partly unclear and standards are not commercially available. This work is focused on the preparation of sulfated metabolites of silymarin flavonolignans. Sulfated flavonolignans were prepared using aryl sulfotransferase from Desulfitobacterium hafniense and p-nitrophenyl sulfate as a sulfate donor and characterized by high-resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR). 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; ferric (FRAP) and Folin–Ciocalteu reagent (FCR) reducing activity; anti-lipoperoxidant potential; and effect on the nuclear erythroid 2-related factor 2 (Nrf2) signaling pathway were examined. Pure silybin A 20-O-sulfate, silybin B 20-O-sulfate, 2,3-dehydrosilybin-20-O-sulfate, 2,3-dehydrosilybin-7,20-di-O-sulfate, silychristin-19-O-sulfate, 2,3-dehydrosilychristin-19-O-sulfate, and silydianin-19-O-sulfate were prepared and fully characterized. Sulfated 2,3-dehydroderivatives were more active in FCR and FRAP assays than the parent compounds, and remaining sulfates were less active chemoprotectants. The sulfated flavonolignans obtained can be now used as authentic standards for in vivo metabolic experiments and for further research on their biological activity. Silybum marianum sulfate sulfotransferase biotransformation metabolites activity Biology (General) Chemistry Kateřina Purchartová verfasserin aut Lenka Rydlová verfasserin aut Lenka Roubalová verfasserin aut David Biedermann verfasserin aut Lucie Petrásková verfasserin aut Alena Křenková verfasserin aut Helena Pelantová verfasserin aut Veronika Holečková-Moravcová verfasserin aut Eva Tesařová verfasserin aut Josef Cvačka verfasserin aut Jiří Vrba verfasserin aut Jitka Ulrichová verfasserin aut Vladimír Křen verfasserin aut In International Journal of Molecular Sciences MDPI AG, 2003 19(2018), 8, p 2349 (DE-627)316340715 (DE-600)2019364-6 14220067 nnns volume:19 year:2018 number:8, p 2349 https://doi.org/10.3390/ijms19082349 kostenfrei https://doaj.org/article/8946e26fc003456193d988433904ee1a kostenfrei http://www.mdpi.com/1422-0067/19/8/2349 kostenfrei https://doaj.org/toc/1422-0067 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ 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 19 2018 8, p 2349
allfields_unstemmed	10.3390/ijms19082349 doi (DE-627)DOAJ01263610X (DE-599)DOAJ8946e26fc003456193d988433904ee1a DE-627 ger DE-627 rakwb eng QH301-705.5 QD1-999 Kateřina Valentová verfasserin aut Sulfated Metabolites of Flavonolignans and 2,3-Dehydroflavonolignans: Preparation and Properties 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Silymarin, an extract from milk thistle (Silybum marianum) fruits, is consumed in various food supplements. The metabolism of silymarin flavonolignans in mammals is complex, the exact structure of their metabolites still remains partly unclear and standards are not commercially available. This work is focused on the preparation of sulfated metabolites of silymarin flavonolignans. Sulfated flavonolignans were prepared using aryl sulfotransferase from Desulfitobacterium hafniense and p-nitrophenyl sulfate as a sulfate donor and characterized by high-resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR). 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; ferric (FRAP) and Folin–Ciocalteu reagent (FCR) reducing activity; anti-lipoperoxidant potential; and effect on the nuclear erythroid 2-related factor 2 (Nrf2) signaling pathway were examined. Pure silybin A 20-O-sulfate, silybin B 20-O-sulfate, 2,3-dehydrosilybin-20-O-sulfate, 2,3-dehydrosilybin-7,20-di-O-sulfate, silychristin-19-O-sulfate, 2,3-dehydrosilychristin-19-O-sulfate, and silydianin-19-O-sulfate were prepared and fully characterized. Sulfated 2,3-dehydroderivatives were more active in FCR and FRAP assays than the parent compounds, and remaining sulfates were less active chemoprotectants. The sulfated flavonolignans obtained can be now used as authentic standards for in vivo metabolic experiments and for further research on their biological activity. Silybum marianum sulfate sulfotransferase biotransformation metabolites activity Biology (General) Chemistry Kateřina Purchartová verfasserin aut Lenka Rydlová verfasserin aut Lenka Roubalová verfasserin aut David Biedermann verfasserin aut Lucie Petrásková verfasserin aut Alena Křenková verfasserin aut Helena Pelantová verfasserin aut Veronika Holečková-Moravcová verfasserin aut Eva Tesařová verfasserin aut Josef Cvačka verfasserin aut Jiří Vrba verfasserin aut Jitka Ulrichová verfasserin aut Vladimír Křen verfasserin aut In International Journal of Molecular Sciences MDPI AG, 2003 19(2018), 8, p 2349 (DE-627)316340715 (DE-600)2019364-6 14220067 nnns volume:19 year:2018 number:8, p 2349 https://doi.org/10.3390/ijms19082349 kostenfrei https://doaj.org/article/8946e26fc003456193d988433904ee1a kostenfrei http://www.mdpi.com/1422-0067/19/8/2349 kostenfrei https://doaj.org/toc/1422-0067 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ 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 19 2018 8, p 2349
allfieldsGer	10.3390/ijms19082349 doi (DE-627)DOAJ01263610X (DE-599)DOAJ8946e26fc003456193d988433904ee1a DE-627 ger DE-627 rakwb eng QH301-705.5 QD1-999 Kateřina Valentová verfasserin aut Sulfated Metabolites of Flavonolignans and 2,3-Dehydroflavonolignans: Preparation and Properties 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Silymarin, an extract from milk thistle (Silybum marianum) fruits, is consumed in various food supplements. The metabolism of silymarin flavonolignans in mammals is complex, the exact structure of their metabolites still remains partly unclear and standards are not commercially available. This work is focused on the preparation of sulfated metabolites of silymarin flavonolignans. Sulfated flavonolignans were prepared using aryl sulfotransferase from Desulfitobacterium hafniense and p-nitrophenyl sulfate as a sulfate donor and characterized by high-resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR). 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; ferric (FRAP) and Folin–Ciocalteu reagent (FCR) reducing activity; anti-lipoperoxidant potential; and effect on the nuclear erythroid 2-related factor 2 (Nrf2) signaling pathway were examined. Pure silybin A 20-O-sulfate, silybin B 20-O-sulfate, 2,3-dehydrosilybin-20-O-sulfate, 2,3-dehydrosilybin-7,20-di-O-sulfate, silychristin-19-O-sulfate, 2,3-dehydrosilychristin-19-O-sulfate, and silydianin-19-O-sulfate were prepared and fully characterized. Sulfated 2,3-dehydroderivatives were more active in FCR and FRAP assays than the parent compounds, and remaining sulfates were less active chemoprotectants. The sulfated flavonolignans obtained can be now used as authentic standards for in vivo metabolic experiments and for further research on their biological activity. Silybum marianum sulfate sulfotransferase biotransformation metabolites activity Biology (General) Chemistry Kateřina Purchartová verfasserin aut Lenka Rydlová verfasserin aut Lenka Roubalová verfasserin aut David Biedermann verfasserin aut Lucie Petrásková verfasserin aut Alena Křenková verfasserin aut Helena Pelantová verfasserin aut Veronika Holečková-Moravcová verfasserin aut Eva Tesařová verfasserin aut Josef Cvačka verfasserin aut Jiří Vrba verfasserin aut Jitka Ulrichová verfasserin aut Vladimír Křen verfasserin aut In International Journal of Molecular Sciences MDPI AG, 2003 19(2018), 8, p 2349 (DE-627)316340715 (DE-600)2019364-6 14220067 nnns volume:19 year:2018 number:8, p 2349 https://doi.org/10.3390/ijms19082349 kostenfrei https://doaj.org/article/8946e26fc003456193d988433904ee1a kostenfrei http://www.mdpi.com/1422-0067/19/8/2349 kostenfrei https://doaj.org/toc/1422-0067 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ 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 19 2018 8, p 2349
allfieldsSound	10.3390/ijms19082349 doi (DE-627)DOAJ01263610X (DE-599)DOAJ8946e26fc003456193d988433904ee1a DE-627 ger DE-627 rakwb eng QH301-705.5 QD1-999 Kateřina Valentová verfasserin aut Sulfated Metabolites of Flavonolignans and 2,3-Dehydroflavonolignans: Preparation and Properties 2018 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Silymarin, an extract from milk thistle (Silybum marianum) fruits, is consumed in various food supplements. The metabolism of silymarin flavonolignans in mammals is complex, the exact structure of their metabolites still remains partly unclear and standards are not commercially available. This work is focused on the preparation of sulfated metabolites of silymarin flavonolignans. Sulfated flavonolignans were prepared using aryl sulfotransferase from Desulfitobacterium hafniense and p-nitrophenyl sulfate as a sulfate donor and characterized by high-resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR). 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; ferric (FRAP) and Folin–Ciocalteu reagent (FCR) reducing activity; anti-lipoperoxidant potential; and effect on the nuclear erythroid 2-related factor 2 (Nrf2) signaling pathway were examined. Pure silybin A 20-O-sulfate, silybin B 20-O-sulfate, 2,3-dehydrosilybin-20-O-sulfate, 2,3-dehydrosilybin-7,20-di-O-sulfate, silychristin-19-O-sulfate, 2,3-dehydrosilychristin-19-O-sulfate, and silydianin-19-O-sulfate were prepared and fully characterized. Sulfated 2,3-dehydroderivatives were more active in FCR and FRAP assays than the parent compounds, and remaining sulfates were less active chemoprotectants. The sulfated flavonolignans obtained can be now used as authentic standards for in vivo metabolic experiments and for further research on their biological activity. Silybum marianum sulfate sulfotransferase biotransformation metabolites activity Biology (General) Chemistry Kateřina Purchartová verfasserin aut Lenka Rydlová verfasserin aut Lenka Roubalová verfasserin aut David Biedermann verfasserin aut Lucie Petrásková verfasserin aut Alena Křenková verfasserin aut Helena Pelantová verfasserin aut Veronika Holečková-Moravcová verfasserin aut Eva Tesařová verfasserin aut Josef Cvačka verfasserin aut Jiří Vrba verfasserin aut Jitka Ulrichová verfasserin aut Vladimír Křen verfasserin aut In International Journal of Molecular Sciences MDPI AG, 2003 19(2018), 8, p 2349 (DE-627)316340715 (DE-600)2019364-6 14220067 nnns volume:19 year:2018 number:8, p 2349 https://doi.org/10.3390/ijms19082349 kostenfrei https://doaj.org/article/8946e26fc003456193d988433904ee1a kostenfrei http://www.mdpi.com/1422-0067/19/8/2349 kostenfrei https://doaj.org/toc/1422-0067 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ 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 19 2018 8, p 2349
language	English
source	In International Journal of Molecular Sciences 19(2018), 8, p 2349 volume:19 year:2018 number:8, p 2349
sourceStr	In International Journal of Molecular Sciences 19(2018), 8, p 2349 volume:19 year:2018 number:8, p 2349
format_phy_str_mv	Article
institution	findex.gbv.de
topic_facet	Silybum marianum sulfate sulfotransferase biotransformation metabolites activity Biology (General) Chemistry
isfreeaccess_bool	true
container_title	International Journal of Molecular Sciences
authorswithroles_txt_mv	Kateřina Valentová @@aut@@ Kateřina Purchartová @@aut@@ Lenka Rydlová @@aut@@ Lenka Roubalová @@aut@@ David Biedermann @@aut@@ Lucie Petrásková @@aut@@ Alena Křenková @@aut@@ Helena Pelantová @@aut@@ Veronika Holečková-Moravcová @@aut@@ Eva Tesařová @@aut@@ Josef Cvačka @@aut@@ Jiří Vrba @@aut@@ Jitka Ulrichová @@aut@@ Vladimír Křen @@aut@@
publishDateDaySort_date	2018-01-01T00:00:00Z
hierarchy_top_id	316340715
id	DOAJ01263610X
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 Silybum marianum misc sulfate misc sulfotransferase misc biotransformation misc metabolites misc activity misc Biology (General) misc Chemistry Sulfated Metabolites of Flavonolignans and 2,3-Dehydroflavonolignans: Preparation and Properties
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topic_title	QH301-705.5 QD1-999 Sulfated Metabolites of Flavonolignans and 2,3-Dehydroflavonolignans: Preparation and Properties Silybum marianum sulfate sulfotransferase biotransformation metabolites activity
topic	misc QH301-705.5 misc QD1-999 misc Silybum marianum misc sulfate misc sulfotransferase misc biotransformation misc metabolites misc activity misc Biology (General) misc Chemistry
topic_unstemmed	misc QH301-705.5 misc QD1-999 misc Silybum marianum misc sulfate misc sulfotransferase misc biotransformation misc metabolites misc activity misc Biology (General) misc Chemistry
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title	Sulfated Metabolites of Flavonolignans and 2,3-Dehydroflavonolignans: Preparation and Properties
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title_full	Sulfated Metabolites of Flavonolignans and 2,3-Dehydroflavonolignans: Preparation and Properties
author_sort	Kateřina Valentová
journal	International Journal of Molecular Sciences
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author_browse	Kateřina Valentová Kateřina Purchartová Lenka Rydlová Lenka Roubalová David Biedermann Lucie Petrásková Alena Křenková Helena Pelantová Veronika Holečková-Moravcová Eva Tesařová Josef Cvačka Jiří Vrba Jitka Ulrichová Vladimír Křen
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author-letter	Kateřina Valentová
doi_str_mv	10.3390/ijms19082349
author2-role	verfasserin
title_sort	sulfated metabolites of flavonolignans and 2,3-dehydroflavonolignans: preparation and properties
callnumber	QH301-705.5
title_auth	Sulfated Metabolites of Flavonolignans and 2,3-Dehydroflavonolignans: Preparation and Properties
abstract	Silymarin, an extract from milk thistle (Silybum marianum) fruits, is consumed in various food supplements. The metabolism of silymarin flavonolignans in mammals is complex, the exact structure of their metabolites still remains partly unclear and standards are not commercially available. This work is focused on the preparation of sulfated metabolites of silymarin flavonolignans. Sulfated flavonolignans were prepared using aryl sulfotransferase from Desulfitobacterium hafniense and p-nitrophenyl sulfate as a sulfate donor and characterized by high-resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR). 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; ferric (FRAP) and Folin–Ciocalteu reagent (FCR) reducing activity; anti-lipoperoxidant potential; and effect on the nuclear erythroid 2-related factor 2 (Nrf2) signaling pathway were examined. Pure silybin A 20-O-sulfate, silybin B 20-O-sulfate, 2,3-dehydrosilybin-20-O-sulfate, 2,3-dehydrosilybin-7,20-di-O-sulfate, silychristin-19-O-sulfate, 2,3-dehydrosilychristin-19-O-sulfate, and silydianin-19-O-sulfate were prepared and fully characterized. Sulfated 2,3-dehydroderivatives were more active in FCR and FRAP assays than the parent compounds, and remaining sulfates were less active chemoprotectants. The sulfated flavonolignans obtained can be now used as authentic standards for in vivo metabolic experiments and for further research on their biological activity.
abstractGer	Silymarin, an extract from milk thistle (Silybum marianum) fruits, is consumed in various food supplements. The metabolism of silymarin flavonolignans in mammals is complex, the exact structure of their metabolites still remains partly unclear and standards are not commercially available. This work is focused on the preparation of sulfated metabolites of silymarin flavonolignans. Sulfated flavonolignans were prepared using aryl sulfotransferase from Desulfitobacterium hafniense and p-nitrophenyl sulfate as a sulfate donor and characterized by high-resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR). 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; ferric (FRAP) and Folin–Ciocalteu reagent (FCR) reducing activity; anti-lipoperoxidant potential; and effect on the nuclear erythroid 2-related factor 2 (Nrf2) signaling pathway were examined. Pure silybin A 20-O-sulfate, silybin B 20-O-sulfate, 2,3-dehydrosilybin-20-O-sulfate, 2,3-dehydrosilybin-7,20-di-O-sulfate, silychristin-19-O-sulfate, 2,3-dehydrosilychristin-19-O-sulfate, and silydianin-19-O-sulfate were prepared and fully characterized. Sulfated 2,3-dehydroderivatives were more active in FCR and FRAP assays than the parent compounds, and remaining sulfates were less active chemoprotectants. The sulfated flavonolignans obtained can be now used as authentic standards for in vivo metabolic experiments and for further research on their biological activity.
abstract_unstemmed	Silymarin, an extract from milk thistle (Silybum marianum) fruits, is consumed in various food supplements. The metabolism of silymarin flavonolignans in mammals is complex, the exact structure of their metabolites still remains partly unclear and standards are not commercially available. This work is focused on the preparation of sulfated metabolites of silymarin flavonolignans. Sulfated flavonolignans were prepared using aryl sulfotransferase from Desulfitobacterium hafniense and p-nitrophenyl sulfate as a sulfate donor and characterized by high-resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR). 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; ferric (FRAP) and Folin–Ciocalteu reagent (FCR) reducing activity; anti-lipoperoxidant potential; and effect on the nuclear erythroid 2-related factor 2 (Nrf2) signaling pathway were examined. Pure silybin A 20-O-sulfate, silybin B 20-O-sulfate, 2,3-dehydrosilybin-20-O-sulfate, 2,3-dehydrosilybin-7,20-di-O-sulfate, silychristin-19-O-sulfate, 2,3-dehydrosilychristin-19-O-sulfate, and silydianin-19-O-sulfate were prepared and fully characterized. Sulfated 2,3-dehydroderivatives were more active in FCR and FRAP assays than the parent compounds, and remaining sulfates were less active chemoprotectants. The sulfated flavonolignans obtained can be now used as authentic standards for in vivo metabolic experiments and for further research on their biological activity.
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container_issue	8, p 2349
title_short	Sulfated Metabolites of Flavonolignans and 2,3-Dehydroflavonolignans: Preparation and Properties
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author2	Kateřina Purchartová Lenka Rydlová Lenka Roubalová David Biedermann Lucie Petrásková Alena Křenková Helena Pelantová Veronika Holečková-Moravcová Eva Tesařová Josef Cvačka Jiří Vrba Jitka Ulrichová Vladimír Křen
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