Sulfation modulates the cell uptake, antiradical activity and biological effects of flavonoids in vitro: An examination of quercetin, isoquercitrin and taxifolin
Language English Country Great Britain, England Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
26260337
DOI
10.1016/j.bmc.2015.07.055
PII: S0968-0896(15)00639-2
Knihovny.cz E-resources
- Keywords
- Antiradical activity, Arylsulfate sulfotransferase, Flavonoids, Gene expression, Metabolism, Sulfate,
- MeSH
- Cell Line MeSH
- Hep G2 Cells MeSH
- Cytochrome P-450 CYP1A1 genetics MeSH
- Heme Oxygenase-1 genetics MeSH
- Humans MeSH
- Mice MeSH
- Quercetin analogs & derivatives chemistry metabolism pharmacokinetics pharmacology MeSH
- Gene Expression Regulation drug effects MeSH
- Free Radical Scavengers chemistry metabolism pharmacokinetics pharmacology MeSH
- Animals MeSH
- Check Tag
- Humans MeSH
- Mice MeSH
- Animals MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- CYP1A1 protein, human MeSH Browser
- Cytochrome P-450 CYP1A1 MeSH
- Heme Oxygenase-1 MeSH
- isoquercitrin MeSH Browser
- quercetin 3'-sulfate MeSH Browser
- Quercetin MeSH
- Free Radical Scavengers MeSH
- taxifolin MeSH Browser
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.
References provided by Crossref.org
New Bacterial Aryl Sulfotransferases: Effective Tools for Sulfation of Polyphenols
Selectively Halogenated Flavonolignans-Preparation and Antibacterial Activity
Sulfated Phenolic Substances: Preparation and Optimized HPLC Analysis
Identification of Human Sulfotransferases Active towards Silymarin Flavonolignans and Taxifolin
Sulfated Metabolites of Flavonolignans and 2,3-Dehydroflavonolignans: Preparation and Properties
