Semisynthesis and spectral characterization of 5-methylpyranopelargonidin and 4-methylfuropelargonidin and their separation and detection in strawberry fruit wine
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F17%3A73584095" target="_blank" >RIV/61989592:15310/17:73584095 - isvavai.cz</a>
Alternative codes found
RIV/61388971:_____/17:00479436
Result on the web
<a href="https://www.sciencedirect.com/science/article/pii/S0021967317309196" target="_blank" >https://www.sciencedirect.com/science/article/pii/S0021967317309196</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.chroma.2017.06.051" target="_blank" >10.1016/j.chroma.2017.06.051</a>
Alternative languages
Result language
angličtina
Original language name
Semisynthesis and spectral characterization of 5-methylpyranopelargonidin and 4-methylfuropelargonidin and their separation and detection in strawberry fruit wine
Original language description
Condensation of anthocyanins and their aglycons with small organic molecules yields more stable natural dyes, e.g. pyranoanthocyanins arising spontaneously in various food products. Reaction of pelargonidin with acetone produces two isomeric anthocyanidin dyes 5-methylpyranopelargonidin and 4-methylfuropelargonidin. A robust semipreparative liquid chromatographic method was developed to isolate both derivatives from a simple aged solution of pelargonidin in methanol: acetone: 37% aqueous hydrochloric acid (1:1:0.008, v/v/v). Detailed interpretation of mass and nuclear magnetic resonance spectra allowed to assign structures of both dyes in isolated fractions. A fast UHPLC-MS method was optimized for the control of their production in the reaction mixture. Use of reversed stationary phase and acidic mobile phases in gradient mode allowed separation of both isomers in less than one minute. Fragmentation of both dyes after collision activated dissociation in collision cell was studied comprehensively and the observed processes were compared with data from quantum calculations (computational chemistry utilizing DFT methods). When comparing both isomers, retro-Diels-Alder fragmentation appears preferred in furo-derivative, while small losses (i.e. methane and water molecules) were more pronounced in pyrano-derivative. Both studied isomeric dyes were found in laboratory prepared strawberry fruit wine and their content was compared with major present anthocyanins and their derivatives.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10406 - Analytical chemistry
Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2017
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Chromatography A: Symposium Volumes
ISSN
0021-9673
e-ISSN
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Volume of the periodical
1510
Issue of the periodical within the volume
aug
Country of publishing house
NL - THE KINGDOM OF THE NETHERLANDS
Number of pages
11
Pages from-to
40-50
UT code for WoS article
000405973400005
EID of the result in the Scopus database
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