Sulfated Metabolites of Luteolin, Myricetin, and Ampelopsin: Chemoenzymatic Preparation and Biophysical Properties
Jazyk angličtina Země Spojené státy americké Médium print-electronic
Typ dokumentu časopisecké články
PubMed
32910657
DOI
10.1021/acs.jafc.0c03997
Knihovny.cz E-zdroje
- Klíčová slova
- ampelopsin, arylsulfotransferase, luteolin, myricetin, quercetin, sulfates,
- MeSH
- antioxidancia chemie farmakologie MeSH
- arylsulfotransferasa chemie MeSH
- bakteriální proteiny chemie MeSH
- biofyzikální jevy MeSH
- biokatalýza MeSH
- Desulfitobacterium enzymologie MeSH
- flavonoidy chemie metabolismus farmakologie MeSH
- isomerie MeSH
- jaterní mikrozomy účinky léků metabolismus MeSH
- krysa rodu Rattus MeSH
- luteolin chemie metabolismus farmakologie MeSH
- molekulární struktura MeSH
- peroxidace lipidů účinky léků MeSH
- sírany chemie metabolismus MeSH
- zvířata MeSH
- Check Tag
- krysa rodu Rattus MeSH
- mužské pohlaví MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- ampelopsin MeSH Prohlížeč
- antioxidancia MeSH
- arylsulfotransferasa MeSH
- bakteriální proteiny MeSH
- flavonoidy MeSH
- luteolin MeSH
- myricetin MeSH Prohlížeč
- sírany MeSH
Authentic standards of food flavonoids are important for human metabolic studies. Their isolation from biological materials is impracticable; however, they can be prepared in vitro. Twelve sulfated metabolites of luteolin, myricetin, and ampelopsin were obtained with arylsulfotransferase from Desulfitobacterium hafniense and fully characterized by high-performance liquid chromatography, MS, and NMR. The compounds were tested for their ability to scavenge 1,1-diphenyl-2-picrylhydrazyl, 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid), and N,N-dimethyl-p-phenylenediamine radicals, to reduce ferric ions and Folin-Ciocalteu reagent, and to inhibit tert-butyl hydroperoxide-induced lipid peroxidation of rat liver microsomes. The activity differed considerably even between monosulfate isomers. The parent compounds and myricetin-3'-O-sulfate were the most active while other compounds displayed significantly lower activity, particularly luteolin sulfates. No mutagenic activity of the parent compounds and their main metabolites was observed; only myricetin showed minor pro-mutagenicity. The prepared sulfated metabolites are now available as authentic standards for future in vitro and in vivo metabolic studies.
Citace poskytuje Crossref.org
New Bacterial Aryl Sulfotransferases: Effective Tools for Sulfation of Polyphenols
Sulfation of Phenolic Acids: Chemoenzymatic vs. Chemical Synthesis
Sulfated Phenolic Substances: Preparation and Optimized HPLC Analysis
