Abstract
Pyranoanthocyanins are anthocyanin-derived pigments with higher stability to pH and storage. However, their slow formation and scarcity in nature hinder their industrial application. Pyranoanthocyanin formation can be accelerated by selecting anthocyanin substitutions, cofactor concentrations, and temperature. Limited information is available on the impacts of the chemical structure of the cofactor and anthocyanin; therefore, we evaluated their impacts on pyranoanthocyanin formation efficiency under conditions reported as favorable for the reaction. Different cofactors were evaluated including pyruvic acid, acetone, and hydroxycinnamic acids (p-coumaric, caffeic, ferulic, and sinapic acid) by incubating them with anthocyanins in a molar ratio of 1:30 (anthocyanin:cofactor), pH 3.1, and 45 °C. The impact of the anthocyanin aglycone was evaluated by incubating delphinidin, cyanidin, petunidin, or malvidin derivatives with the most efficient cofactor (caffeic acid) under identical conditions. Pigments were identified using UHPLC-PDA and tandem mass spectrometry, and pyranoanthocyanin formation was monitored for up to 72 h. Pyranoanthocyanin yields were the highest with caffeic acid (~17% at 72 h, p < 0.05). When comparing anthocyanins, malvidin-3-O-glycosides yielded twice as many pyranoanthocyanins after 24 h (~20%, p < 0.01) as cyanidin-3-O-glycosides. Petunidin- and delphinidin-3-O-glycosides yielded <2% pyranoanthocyanins. This study demonstrated the importance of anthocyanin and cofactor selection in pyranoanthocyanin production.
Highlights
Anthocyanins (ACNs) are dietary flavonoids with bright colors that can range from red to blue [1,2]
The ACN extract was mainly composed of cyanidin-3-O-xylosylglucosyl-galactoside and cyanidin-3O-xylosyl-galactoside
Their hypsochromic shift of λvis-max compared to the precursor ACNs, later retention times, and MS spectra revealed that these new peaks corresponded to 10catechyl-PACNs derived from the ACNs previously identified in saponified black carrot ACN extracts (sBC)
Summary
Anthocyanins (ACNs) are dietary flavonoids with bright colors that can range from red to blue [1,2]. The use of ACN-rich extracts as food colorants has increased in recent years due to potential behavioral concerns associated with the consumption of artificial dyes [3,4]. Interest in ACN consumption has grown due to their potential bioactive and healthpromoting properties [5]. From an industrial point of view, the application of ACN-rich extracts as food colorants is restricted due to limited long-term stability and color expression [1]. Several mechanisms have been proposed for the stabilization of ACNs in foods such as copigmentation with phenolic compounds [7], complexation with proteins [8], encapsulation within polysaccharides [9], and chelation with metals [10]
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