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Molecules 2018, 23(4), 744;

Investigating the Interaction of Ascorbic Acid with Anthocyanins and Pyranoanthocyanins

Department of Food Science and Technology, The Ohio State University, 2015 Fyffe Ct., Columbus, OH 43210-1007, USA
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 27 February 2018 / Revised: 18 March 2018 / Accepted: 21 March 2018 / Published: 23 March 2018
(This article belongs to the Special Issue Advances in Anthocyanin Research 2018)
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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 (λvis-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. View Full-Text
Keywords: anthocyanins; pyranoanthocyanins; ascorbic acid; bleaching; condensation anthocyanins; pyranoanthocyanins; ascorbic acid; bleaching; condensation

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Farr, J.E.; Giusti, M.M. Investigating the Interaction of Ascorbic Acid with Anthocyanins and Pyranoanthocyanins. Molecules 2018, 23, 744.

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