Compartir
Título
Preparation and Characterization of Protocatechuic Acid Sulfates
Autor(es)
Palabras clave
Polyphenols
Phenolic metabolites
Phase II conjugates
Phenolic acids
Sulfates
Hemisynthesis
Identification
Clasificación UNESCO
2302 Bioquímica
2306 Química Orgánica
Fecha de publicación
2019
Resumen
[EN]Protocatechuic acid (3,4-dihydroxybenzoic acid; PCA) is a phenolic acid present in plants
as a secondary metabolite and is also produced in the human organism as a metabolite from the
degradation of polyphenols by the intestinal microbiota, particularly of flavonoids. However, PCA,
like most polyphenols, is biotransformed in the human body to di erent conjugates as sulfates,
which are found circulating in blood and could be involved in the bioactivity of the original compound.
This paper describes a simple process for the preparation of PCA monosulfates with satisfactory yields.
Two compounds were obtained that were identified as PCA-3-sulfate and PCA-4-sulfate by mass
spectrometry and 1H and 13C nuclear magnetic resonance using one- and two-dimensional techniques
(heteronuclear single-quantum coherence and heteronuclear multiple-bond correlation). Di erential
MS fragmentation behavior and UV spectra were observed for each compound, which could be used
for their identification in samples of unknown composition. The described procedure can be used for
the preparation of these polyphenol metabolites in view of their use in in vivo and in vitro studies,
as well as standards for their analysis in biological fluids, to contribute to the elucidation of biological
e ects of dietary polyphenols.
URI
DOI
10.3390/molecules24020307
Versión del editor
Collections
- GIP. Artículos [86]