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Comparing the thermal stability of 10-carboxy-, 10-methyl-, and 10-catechyl-pyranocyanidin-3-glucosides and their precursor, cyanidin-3-glucoside

Pyranoanthocyanins are vibrant, naturally derived pigments formed by the reaction of an anthocyanin with a cofactor containing a partially negatively charged carbon. This study compared the thermal stability and degradation products of 10-carboxy-pyranocyanidin-3-glucoside (pyruvic acid cofactor), 1...

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Detalles Bibliográficos
Autores principales: Voss, Danielle M., Miyagusuku-Cruzado, Gonzalo, Giusti, M. Mónica
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8857255/
https://www.ncbi.nlm.nih.gov/pubmed/35181657
http://dx.doi.org/10.1038/s41538-022-00131-9
Descripción
Sumario:Pyranoanthocyanins are vibrant, naturally derived pigments formed by the reaction of an anthocyanin with a cofactor containing a partially negatively charged carbon. This study compared the thermal stability and degradation products of 10-carboxy-pyranocyanidin-3-glucoside (pyruvic acid cofactor), 10-methyl-pyranocyanidin-3-glucoside (acetone cofactor), and 10-catechyl-pyranocyanidin-3-glucoside (caffeic acid cofactor) with their anthocyanin precursor to evaluate the role of the pyranoanthocyanin C(10) substitution on stability. Pyranoanthocyanins exhibited absorbance half-lives ~2.1–8.6 times greater than cyanidin-3-glucoside, with ~15–52% of their original pigment remaining after 12 h of 90 °C heating at pH 3.0. 10-Methyl-pyranocyanidin-3-glucoside was the most stable (p < 0.01) based on UHPLC-PDA analysis, while 10-catechyl-pyranocyanidin-3-glucoside had the most stable color in part due to contribution from a colored degradation compound. Protocatechuic acid formed in all heated samples, which suggested a similar degradation mechanism among pigments. In conclusion, the C(10) substitution impacted the extent of pyranoanthocyanin stability and the degradation compounds formed.