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Int. J. Mol. Sci. 2016, 17(10), 1751; doi:10.3390/ijms17101751

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

1
LAQV-REQUIMTE, Department of Chemistry, Faculty of Science & Technology, Universidade NOVA de Lisboa, 2829-516 Monte de Caparica, Portugal
2
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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Abstract

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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MDPI and ACS Style

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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