Sulfation modulates the cell uptake, antiradical activity and biological effects of flavonoids in vitro: An examination of quercetin, isoquercitrin and taxifolin
Jazyk angličtina Země Velká Británie, Anglie Médium print-electronic
Typ dokumentu časopisecké články, práce podpořená grantem
PubMed
26260337
DOI
10.1016/j.bmc.2015.07.055
PII: S0968-0896(15)00639-2
Knihovny.cz E-zdroje
- Klíčová slova
- Antiradical activity, Arylsulfate sulfotransferase, Flavonoids, Gene expression, Metabolism, Sulfate,
- MeSH
- buněčné linie MeSH
- buňky Hep G2 MeSH
- cytochrom P-450 CYP1A1 genetika MeSH
- hemoxygenasa-1 genetika MeSH
- lidé MeSH
- myši MeSH
- quercetin analogy a deriváty chemie metabolismus farmakokinetika farmakologie MeSH
- regulace genové exprese účinky léků MeSH
- scavengery volných radikálů chemie metabolismus farmakokinetika farmakologie MeSH
- zvířata MeSH
- Check Tag
- lidé MeSH
- myši MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- CYP1A1 protein, human MeSH Prohlížeč
- cytochrom P-450 CYP1A1 MeSH
- hemoxygenasa-1 MeSH
- isoquercitrin MeSH Prohlížeč
- quercetin 3'-sulfate MeSH Prohlížeč
- quercetin MeSH
- scavengery volných radikálů MeSH
- taxifolin MeSH Prohlížeč
Quercetin 3'-O-sulfate is one of the main metabolites of the natural flavonoid quercetin in humans. This study was designed to prepare quercetin 3'-O-sulfate (1), isoquercitrin 4'-O-sulfate (2) and taxifolin 4'-O-sulfate (3) by the sulfation of quercetin, isoquercitrin (quercetin 3-O-glucoside) and taxifolin (2,3-dihydroquercetin) using the arylsulfate sulfotransferase from Desulfitobacterium hafniense, and to examine the effect of sulfation on selected biological properties of the flavonoids tested. We found that flavonoid sulfates 1-3 were weaker DPPH radical scavengers than the corresponding nonsulfated flavonoids, and that 1-3, unlike quercetin, did not induce the expression of either heme oxygenase-1 in RAW264.7 cells or cytochrome P450 1A1 in HepG2 cells. In both cell types, the cell uptake of compounds 1-3 was much lower than that of quercetin, but comparable to that of the glycoside isoquercitrin. Moreover, HPLC/MS metabolic profiling in HepG2 cells showed that flavonoid sulfates 1-3 were metabolized to a limited extent compared to the nonsulfated compounds. We conclude that sulfation of the tested flavonoids reduces their antiradical activity, and affects their cell uptake and biological activity in vitro.
Citace poskytuje Crossref.org
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