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Color Properties of Four Cyanidin−Pyruvic Acid Adducts

Authors: Joana, Oliveira; Virgínia, Fernandes; Candida, Miranda; Celestino, Santos-Buelga; Artur, Silva; Victor, de Freitas; Nuno, Mateus;

Color Properties of Four Cyanidin−Pyruvic Acid Adducts

Abstract

Four anthocyanin-pyruvic adducts were synthesized through the reaction of cyanidin 3-O-glucoside, cyanidin 3-O-rutinoside, cyanidin 3-O-sophoroside, and cyanidin 3-O-sambubioside with pyruvic acid, structurally characterized by liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance (NMR), and their chromatic properties were studied (pH and SO2 stability assays). Overall, these pigments were shown to have a higher resistance to discoloration toward pH variations and also in the presence of SO2, being that this resistance to discoloration was explained by a higher protection of the chromophore group against the water or bisulfite nucleophilic attack that gives rise to the colorless hemiacetal form. Only slight differences in the protection against the nucleophilic attack of water and bisulfite were found to occur between all of the cyanidin-pyruvic acid adducts studied. Indeed, anthocyanin-pyruvic acid adducts with glucose or sambubiose attached to the 3-O position of the flavylium moiety were shown to have smaller bleaching constants compared with similar pigments that possess a rutinosyl or sophorosyl moiety. The study of the pigments (A-D and cyanidin-3-O-glucoside) color parameters, namely, chroma (C), lightness (L), and the hue angle (h(a,b)), obtained from the CIELAB system, revealed that different patterns of sugars in the anthocyanin-pyruvic acid adduct moiety affected the referred three parameters of color. The loss of saturation (DeltaC 0) presented by the cyanidin-pyruvic acid adduct solutions at acidic pH values (1.0 and 2.0) showed that they are much less colored than the cyanidin-3-O-glucoside. For higher pH values (5.0 and 7.0), the reverse trend was observed. This means that the cyanidin-pyruvic acid adducts A-D are much more colored than the anthocyanin at these pH values. The higher coloring capacity of these pigments at higher pH values may be an important feature, indicating a putative application of these compounds in food products.

Keywords

Magnetic Resonance Spectroscopy, Color, Pigments, Biological, Hydrogen-Ion Concentration, Anthocyanins, Drug Stability, Sambucus nigra, Spectrophotometry, Fruit, Pyruvic Acid, Prunus, Rosaceae, Chromatography, High Pressure Liquid

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selected citations
These citations are derived from selected sources.
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
69
Top 10%
Top 10%
Top 10%
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