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Investigating the Interaction of Ascorbic Acid with Anthocyanins and Pyranoanthocyanins
Juices colored by anthocyanins experience color loss related to fortification with ascorbic acid (AA), thought to be the result of condensation at Carbon-4 of anthocyanins. To further understand this mechanism, pyranoanthocyanins, having a fourth-ring covalently occupying Carbon-4, were synthesized...
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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MDPI
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6017693/ https://www.ncbi.nlm.nih.gov/pubmed/29570649 http://dx.doi.org/10.3390/molecules23040744 |
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author | Farr, Jacob E. Giusti, M. Monica |
author_facet | Farr, Jacob E. Giusti, M. Monica |
author_sort | Farr, Jacob E. |
collection | PubMed |
description | Juices colored by anthocyanins experience color loss related to fortification with ascorbic acid (AA), thought to be the result of condensation at Carbon-4 of anthocyanins. To further understand this mechanism, pyranoanthocyanins, having a fourth-ring covalently occupying Carbon-4, were synthesized to compare its reactivity with AA against that of anthocyanins. Pyranoanthocyanins were synthesized by combining chokeberry anthocyanins with pyruvic acid. AA (250–1000 mg/L) was added to either chokeberry extract, cyanidin-3-galactoside, or 5-Carboxypyranocyanidin-3-galactoside. Samples were stored in the dark for 5 days at 25 °C and spectra (380–700 nm), color (CIE-L*c*h*), and composition changes (HPLC-MS/MS) were monitored. Extensive bleaching occurred for cyanidin-3-galactoside and chokeberry colored solutions, with a decrease in half-lives from 22.8 to 0.3 days for Cyanidin-3-galactoside when 1000 mg/L AA was added. 5-Carboxypyranocyanidin-3-galactoside solution better maintained color with limited loss in absorbance, due to the formation of colored degradation products (λ(vis-max) = 477 to 487 nm), and half-life decrease from 40.8 to 2.7 days, an 8–13-fold improvement compared to anthocyanins. This suggested alternative sites of reactivity with AA. Carbon-4 may be the preferred site for AA-pigment interactions, but it was not the only location. With Carbon-4 blocked, 5-Carboxypyranocyanidin-3-galactoside reacted with AA to form new pigments and reduce bleaching. |
format | Online Article Text |
id | pubmed-6017693 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-60176932018-11-13 Investigating the Interaction of Ascorbic Acid with Anthocyanins and Pyranoanthocyanins Farr, Jacob E. Giusti, M. Monica Molecules Article Juices colored by anthocyanins experience color loss related to fortification with ascorbic acid (AA), thought to be the result of condensation at Carbon-4 of anthocyanins. To further understand this mechanism, pyranoanthocyanins, having a fourth-ring covalently occupying Carbon-4, were synthesized to compare its reactivity with AA against that of anthocyanins. Pyranoanthocyanins were synthesized by combining chokeberry anthocyanins with pyruvic acid. AA (250–1000 mg/L) was added to either chokeberry extract, cyanidin-3-galactoside, or 5-Carboxypyranocyanidin-3-galactoside. Samples were stored in the dark for 5 days at 25 °C and spectra (380–700 nm), color (CIE-L*c*h*), and composition changes (HPLC-MS/MS) were monitored. Extensive bleaching occurred for cyanidin-3-galactoside and chokeberry colored solutions, with a decrease in half-lives from 22.8 to 0.3 days for Cyanidin-3-galactoside when 1000 mg/L AA was added. 5-Carboxypyranocyanidin-3-galactoside solution better maintained color with limited loss in absorbance, due to the formation of colored degradation products (λ(vis-max) = 477 to 487 nm), and half-life decrease from 40.8 to 2.7 days, an 8–13-fold improvement compared to anthocyanins. This suggested alternative sites of reactivity with AA. Carbon-4 may be the preferred site for AA-pigment interactions, but it was not the only location. With Carbon-4 blocked, 5-Carboxypyranocyanidin-3-galactoside reacted with AA to form new pigments and reduce bleaching. MDPI 2018-03-23 /pmc/articles/PMC6017693/ /pubmed/29570649 http://dx.doi.org/10.3390/molecules23040744 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Farr, Jacob E. Giusti, M. Monica Investigating the Interaction of Ascorbic Acid with Anthocyanins and Pyranoanthocyanins |
title | Investigating the Interaction of Ascorbic Acid with Anthocyanins and Pyranoanthocyanins |
title_full | Investigating the Interaction of Ascorbic Acid with Anthocyanins and Pyranoanthocyanins |
title_fullStr | Investigating the Interaction of Ascorbic Acid with Anthocyanins and Pyranoanthocyanins |
title_full_unstemmed | Investigating the Interaction of Ascorbic Acid with Anthocyanins and Pyranoanthocyanins |
title_short | Investigating the Interaction of Ascorbic Acid with Anthocyanins and Pyranoanthocyanins |
title_sort | investigating the interaction of ascorbic acid with anthocyanins and pyranoanthocyanins |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6017693/ https://www.ncbi.nlm.nih.gov/pubmed/29570649 http://dx.doi.org/10.3390/molecules23040744 |
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