Chemoenzymatic Synthesis and Radical Scavenging of Sulfated Hydroxytyrosol, Tyrosol, and Acetylated Derivatives
| Autor: | Lucie Petrásková, Paloma Begines, Inés Maya, Helena Pelantová, Kateřina Valentová, David Biedermann, Vladimír Křen, José G. Fernández-Bolaños |
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| Rok vydání: | 2019 |
| Předmět: |
0106 biological sciences
Desulfitobacterium 01 natural sciences Mass Spectrometry chemistry.chemical_compound Sulfation Bacterial Proteins Phenols Organic chemistry Scavenging Olive Oil Chromatography High Pressure Liquid biology Molecular Structure Chemistry Sulfates 010401 analytical chemistry Desulfitobacterium hafniense Acetylation General Chemistry Free Radical Scavengers Phenylethyl Alcohol biology.organism_classification Arylsulfotransferase 0104 chemical sciences Tyrosol Biocatalysis Hydroxytyrosol General Agricultural and Biological Sciences 010606 plant biology & botany |
| Zdroj: | Journal of agricultural and food chemistry. 67(26) |
| ISSN: | 1520-5118 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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