Study of Tetrahydroxylated Anthraquinones - Potential Tool to Assess Degradation of Anthocyanins Rich Food

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15210%2F21%3A73604414" target="_blank" >RIV/61989592:15210/21:73604414 - isvavai.cz</a>

Alternative codes found

RIV/61989592:15310/21:73604414

Result on the web

<a href="https://www.mdpi.com/1420-3049/26/1/2/htm" target="_blank" >https://www.mdpi.com/1420-3049/26/1/2/htm</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3390/molecules26010002" target="_blank" >10.3390/molecules26010002</a>

Result language

angličtina

Original language name

Study of Tetrahydroxylated Anthraquinones - Potential Tool to Assess Degradation of Anthocyanins Rich Food

Original language description

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.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

—

OECD FORD branch

10406 - Analytical chemistry

Project

<a href="/en/project/GA17-17346S" target="_blank" >GA17-17346S: Advanced chemical analysis of residues of organic materials in archaeological context</a><br>

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year

2021

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

MOLECULES

ISSN

1420-3049

e-ISSN

—

Volume of the periodical

26

Issue of the periodical within the volume

1

Country of publishing house

CH - SWITZERLAND

Number of pages

12

Pages from-to

"26010002-1"-"26010002-12"

UT code for WoS article

000606203100001

EID of the result in the Scopus database

2-s2.0-85099114687