Pyranoanthocyanin formation rates and yields as affected by cyanidin-3-substitutions and pyruvic or caffeic acids.

Anthocyanin-derived pyranoanthocyanins (PACNs) offer potential as food colorants as they may exhibit higher stability than anthocyanins (ACNs). Our objective was to compare PACN formation rate and efficiency from different cyanidin-3-derivatives and cofactors, in order to facilitate PACN production. Four cyanidin-3-derivatives (cyanidin-3-glucoside, cyanidin-3-xylosylglucosylgalactoside, cyanidin-3-malonylglucoside and cyanidin-3-xylosyl(sinapoylglucosyl)galactoside) were incubated with pyruvic or caffeic acids (PA, CA) at 25 °C in the dark for two months. PACN formation was monitored by uHPLC-PDA-MS/MS over time. ACNs incubated with PA produced PACNs with yields increasing steadily over time, reaching 15% after 2 months. PACN formation with CA increased exponentially from the start, reaching 85% during storage. PACNs were efficiently produced from 3 of the 4 ACNs in the presence of CA, with minimal pigment loss. Copigmentation between CA and ACNs may facilitate PACN formation by keeping reactants in close proximity. Anthocyanin glycosylation and acylation affected PACN formation to a lower degree than cofactors.