Study of Tetrahydroxylated Anthraquinones—Potential Tool to Assess Degradation of Anthocyanins Rich Food
| Autor: | Martin Golec, Petr Bednář, Lukáš Kučera, Ondřej Kurka |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Models
Molecular Flavonoid Pharmaceutical Science Anthraquinones Hydroxyanthraquinone 01 natural sciences Mass Spectrometry Article anthocyanin Analytical Chemistry Anthocyanins lcsh:QD241-441 03 medical and health sciences chemistry.chemical_compound 0302 clinical medicine Column chromatography lcsh:Organic chemistry hydroxyanthraquinone Drug Discovery Physical and Theoretical Chemistry wine Bond cleavage Chromatography High Pressure Liquid degradation Wine chemistry.chemical_classification Chromatography Molecular Structure phloroglucinaldehyde 010401 analytical chemistry Organic Chemistry Phenolic acid 0104 chemical sciences chemistry Chemistry (miscellaneous) 030220 oncology & carcinogenesis Anthocyanin Molecular Medicine Food Analysis Chromatography Liquid |
| Zdroj: | Molecules, Vol 26, Iss 2, p 2 (2021) Molecules Molecules; Volume 26; Issue 1; Pages: 2 |
| ISSN: | 1420-3049 |
| Popis: | Degradation of anthocyanins involves scission of the flavonoid skeleton yielding 2,4,6-trihydroxybenzaldehyde (phloroglucinaldehyde, PGA) and a phenolic acid. However, the process is not finished with the formation of PGA, as the consequent condensation of two PGA molecules providing colored hydroxylated anthraquinones was observed for the first time. This process was studied using a combination of preparative column chromatography, nuclear magnetic resonance, liquid chromatography/high resolution tandem mass spectrometry (LC/HRMS2), and quantum calculations using density functional theory. 1,3,5,7-tetrahydroxyanthraquinone (anthrachrysone) and its isomers were found to rise during heating (95 °C) in a buffered PGA model solution (phosphate buffer, pH 7). These compounds were detected in heated red wine after an increase of its pH value. The concentration of the identified anthrachrysone in the red wine reached 0.01 mg·L−1. Presence of those compounds could therefore indicate involvement of certain steps in the processing of plant materials rich in anthocyanins (e.g., utilization of a higher temperature and/or reduction of acidity) or long-term transformation of anthocyanins (potentially, for instance, in archaeological findings such as wine or fruit residues). Additionally, measurement of wine–soil suspensions proved an increase of their pH to the values suitable for anthocyanin cleavage (neutral to slightly alkaline; reached using soil from archaeologically well-known Bull Rock Cave). Although not found in artificially prepared samples (imitations) or authentic materials so far, according to our results the above mentioned conditions are suitable for the formation of tetrahydroxylated anthraquinone derivatives and their monitoring would be beneficial. |
| Databáze: | OpenAIRE |
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