Sulfated Metabolites of Luteolin, Myricetin, and Ampelopsin: Chemoenzymatic Preparation and Biophysical Properties
Language English Country United States Media print-electronic
Document type Journal Article
- Keywords
- ampelopsin, arylsulfotransferase, luteolin, myricetin, quercetin, sulfates,
- MeSH
- Antioxidants chemistry pharmacology MeSH
- Arylsulfotransferase chemistry MeSH
- Bacterial Proteins chemistry MeSH
- Biophysical Phenomena MeSH
- Biocatalysis MeSH
- Desulfitobacterium enzymology MeSH
- Flavonoids chemistry metabolism pharmacology MeSH
- Isomerism MeSH
- Microsomes, Liver drug effects metabolism MeSH
- Rats MeSH
- Luteolin chemistry metabolism pharmacology MeSH
- Molecular Structure MeSH
- Lipid Peroxidation drug effects MeSH
- Sulfates chemistry metabolism MeSH
- Animals MeSH
- Check Tag
- Rats MeSH
- Male MeSH
- Animals MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- ampelopsin MeSH Browser
- Antioxidants MeSH
- Arylsulfotransferase MeSH
- Bacterial Proteins MeSH
- Flavonoids MeSH
- Luteolin MeSH
- myricetin MeSH Browser
- Sulfates 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.
References provided by 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
