Analogs of anthocyanins with a 3′,4′-dihydroxy substitution: Synthesis and investigation of their acid–base, hydration, metal binding and hydrogen-donating properties in aqueous solution

Glycosides of hydroxylated flavylium ions are proposed as pertinent analogs of anthocyanins, a major class of polyphenolic plant pigments. Anthocyanins with a 3′,4′-dihydroxy substitution on the B-ring (catechol nucleus) are especially important for their metal chelating and electron-donating (antio...

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Bibliographic Details
Published in:Dyes and pigments 2013-01, Vol.96 (1), p.7-15
Main Authors: Mora-Soumille, Nathalie, Al Bittar, Sheiraz, Rosa, Maxence, Dangles, Olivier
Format: Article
Language:English
Subjects:
Aluminum
Analogs
Anthocyanin
Anthocyanins
Antioxidant
Antioxidants
Conversion
Flavylium
Glycoside
Life Sciences
Pigments
Radicals
Synthesis
Thermodynamics
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Summary:Glycosides of hydroxylated flavylium ions are proposed as pertinent analogs of anthocyanins, a major class of polyphenolic plant pigments. Anthocyanins with a 3′,4′-dihydroxy substitution on the B-ring (catechol nucleus) are especially important for their metal chelating and electron-donating (antioxidant) capacities. In this work, an efficient chemical synthesis of 3′,4′-dihydroxy-7-O-β-d-glucopyranosyloxyflavylium chloride and its aglycone is reported. Then, the ability of the two pigments to undergo proton transfer (formation of colored quinonoid bases) and add water (formation of a colorless chalcone) is investigated: at equilibrium the colored quinonoid bases (kinetic products) are present in very minor concentrations (
ISSN:0143-7208
1873-3743
DOI:10.1016/j.dyepig.2012.07.006