Chemoenzymatic Synthesis and Radical Scavenging of Sulfated Hydroxytyrosol, Tyrosol, and Acetylated Derivatives
Language English Country United States Media print-electronic
Document type Journal Article
- Keywords
- arylsulfotransferase, chemoenzymatic, hydroxytyrosol, tyrosol, metabolites, olive phenols,
- MeSH
- Acetylation MeSH
- Arylsulfotransferase chemistry MeSH
- Bacterial Proteins chemistry MeSH
- Biocatalysis MeSH
- Desulfitobacterium enzymology MeSH
- Phenylethyl Alcohol analogs & derivatives chemical synthesis chemistry MeSH
- Phenols chemistry MeSH
- Mass Spectrometry MeSH
- Molecular Structure MeSH
- Olive Oil chemistry MeSH
- Free Radical Scavengers chemical synthesis chemistry MeSH
- Sulfates chemistry MeSH
- Chromatography, High Pressure Liquid MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- 3,4-dihydroxyphenylethanol MeSH Browser
- 4-hydroxyphenylethanol MeSH Browser
- Arylsulfotransferase MeSH
- Bacterial Proteins MeSH
- Phenylethyl Alcohol MeSH
- Phenols MeSH
- Olive Oil MeSH
- Free Radical Scavengers MeSH
- Sulfates MeSH
Potential metabolites of bioactive compounds are important for their biological activities and as authentic standards for metabolic studies. The phenolic compounds contained in olive oil are an important part of the human diet, and therefore their potential metabolites are of utmost interest. We developed a convenient, scalable, one-pot chemoenzymatic method using the arylsulfotransferase from Desulfitobacterium hafniense for the sulfation of the natural olive oil phenols tyrosol, hydroxytyrosol, and of their monoacetylated derivatives. Respective monosulfated (tentative) metabolites were fully structurally characterized using LC-MS, NMR, and HRMS. In addition, Folin-Ciocalteu reduction, 1,1-diphenyl-2-picrylhydrazyl radical scavenging, and antilipoperoxidant activity in rat liver microsomes damaged by tert-butylhydroperoxide were measured and compared to the parent compounds. As expected, the sulfation diminished the radical scavenging properties of the prepared compounds. These compounds will serve as authentic standards of phase II metabolites.
Department of Organic Chemistry Faculty of Chemistry University of Seville Sevilla E 41012 Spain
Institute of Microbiology Czech Academy of Sciences Vídeňská 1083 Prague CZ 142 20 Czech Republic
References provided by Crossref.org
Sulfated Phenolic Substances: Preparation and Optimized HPLC Analysis
