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Preparation and Characterization of Protocatechuic Acid Sulfates
- Source :
- Molecules, Molecules, Vol 24, Iss 2, p 307 (2019), Volume 24, Issue 2, GREDOS. Repositorio Institucional de la Universidad de Salamanca, instname
- Publication Year :
- 2019
- Publisher :
- MDPI, 2019.
-
Abstract
- Protocatechuic acid (3,4-dihydroxybenzoic acid<br />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 different 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). Differential 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 effects of dietary polyphenols.
- Subjects :
- Identification
030309 nutrition & dietetics
Phenolic acids
Metabolite
Proton Magnetic Resonance Spectroscopy
phenolic metabolites
Pharmaceutical Science
Secondary metabolite
Protocatechuic acid
Article
Mass Spectrometry
Analytical Chemistry
lcsh:QD241-441
03 medical and health sciences
chemistry.chemical_compound
2302 Bioquímica
lcsh:Organic chemistry
In vivo
Drug Discovery
medicine
Hydroxybenzoates
Physical and Theoretical Chemistry
Carbon-13 Magnetic Resonance Spectroscopy
polyphenols
030304 developmental biology
0303 health sciences
sulfates
Chromatography
Molecular Structure
Sulfates
Organic Chemistry
Polyphenols
food and beverages
Phenolic acid
Phenolic metabolites
2306 Química Orgánica
phase II conjugates
In vitro
Hemisynthesis
hemisynthesis
chemistry
Heteronuclear molecule
Chemistry (miscellaneous)
Polyphenol
Molecular Medicine
identification
Phase II conjugates
phenolic acids
medicine.drug
Subjects
Details
- Language :
- English
- ISSN :
- 14203049
- Volume :
- 24
- Issue :
- 2
- Database :
- OpenAIRE
- Journal :
- Molecules
- Accession number :
- edsair.doi.dedup.....a88066304141e11ee88dbd265c94b656