18393-49-2Relevant articles and documents
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
Mora-Soumille, Nathalie,Al Bittar, Sheiraz,Rosa, Maxence,Dangles, Olivier
, p. 7 - 15,9 (2020/07/31)
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 (3+, the Al3+-glucoside complex is more stable than the Al3+-aglycone complex due to the higher sensitivity of the latter to water addition and conversion into the corresponding chalcone. Finally, the glucopyranosyloxyflavylium ion and its aglycone are compared for their ability to reduce the 1,1-diphenyl-2-picrylhydrazyl radical in a mildly acidic water/MeOH (1:1) mixture as a first evaluation of their antioxidant activity. Glycosidation at C7-OH results in a lower rate constant of first electron transfer to DPPH and a lower stoichiometry (total number of 1,1-diphenyl-2-picrylhydrazyl radicals reduced per pigment molecule). Anthocyanins are difficult to extract from plants in substantial amount. However, the analogs investigated in this work are of easy access by chemical synthesis and express the physico-chemical properties typical of anthocyanins. They can thus be regarded as valuable models for investigating the coloring, metal-binding and antioxidant properties of these important natural pigments.
30. 3′-(β-D-GlycopyranosyIoxy)flavylium Ions: Synthesis and Investigation of Their Properties in Aqueous Solution. Hydrogen Bonding as a Mean of Colour Variation
El Hajji, Hakima,Dangles, Olivier,Figueiredo, Paulo,Brouillard, Raymond
, p. 398 - 413 (2007/10/03)
This work describes a straightforward synthesis of two 3′-(β-D-glycopyranosyloxy)flavylium ions thought to be good models of natural anthocyanins (pigments). For both pigments and for the non-glycosylated flavylium ion taken as a reference, H2O
