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Int. J. Mol. Sci. 2016, 17(10), 1751;

Analogs of Natural 3-Deoxyanthocyanins: O-Glucosides of the 4′,7-Dihydroxyflavylium Ion and the Deep Influence of Glycosidation on Color

LAQV-REQUIMTE, Department of Chemistry, Faculty of Science & Technology, Universidade NOVA de Lisboa, 2829-516 Monte de Caparica, Portugal
Faculty of Sciences, Technology & Health, University of Avignon, INRA, UMR408, 84000 Avignon, France
Authors to whom correspondence should be addressed.
Academic Editors: Nuno Mateus and Iva Fernandes
Received: 23 August 2016 / Revised: 28 September 2016 / Accepted: 12 October 2016 / Published: 20 October 2016
(This article belongs to the Special Issue Anthocyanins)
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3-Deoxyanthocyanidins and their O-β-d-glucosides are natural pigments abundant in black sorghum. O-glycosidation can perturb the acid-base properties of the chromophore and lower its electron density with a large impact on the distribution of colored and colorless forms in aqueous solution. In this work, the influence of O-glycosidation on color is systematically studied from a series of 3-deoxyanthocyanin analogs. The pH- and light-dependent reversible reactions of 7-β-d-glucopyranosyloxy-4′-hydroxyflavylium (P3) and 4′-β-d-glucopyranosyloxy-7-hydroxyflavylium (P5) were completely characterized in mildly acidic solution and compared with the parent aglycone 4′,7-dihydroxyflavylium ion and the O-methylethers of P3 and P5. Except P5, the chalcone forms of the pigments exhibit a high cis-trans isomerization barrier that allows a pseudo-equilibrium involving all species except the trans-chalcone. At equilibrium, only the flavylium cation and trans-chalcone are observed. With all pigments, the colored flavylium ion can be generated by irradiation of the trans-chalcone (photochromism). Glycosidation of C7–OH accelerates hydration and strongly slows down cis-trans isomerization with the pH dependence of the apparent isomerization rate constant shifting from a bell-shaped curve to a sigmoid. The color of P5 is much more stable than that of its regioisomer P3 in near-neutral conditions. View Full-Text
Keywords: 3-deoxyanthocyanidin; flavylium; glucoside; photochromism; multistate 3-deoxyanthocyanidin; flavylium; glucoside; photochromism; multistate

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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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Basílio, N.; Al Bittar, S.; Mora, N.; Dangles, O.; Pina, F. Analogs of Natural 3-Deoxyanthocyanins: O-Glucosides of the 4′,7-Dihydroxyflavylium Ion and the Deep Influence of Glycosidation on Color. Int. J. Mol. Sci. 2016, 17, 1751.

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