High yield production of cyanidin-derived pyranoanthocyanins using 4-vinylphenol and 4-vinylguaiacol as cofactors

• Published in: Food chemistry 2023-11, Vol.427, p.136705-136705, Article 136705
• Main Authors: Miyagusuku-Cruzado, Gonzalo, Voss, Danielle M., Ortiz-Santiago, Thania N., Cheng, Yesen, Giusti, M. Monica
• Format: Article
• Language: English
• Subjects: 10-guaiacyl-pyranoanthocyanin; 10-p-hydroxyphenyl-pyranoanthocyanin; Anthocyanins; Coumaric Acids; Formation kinetics; Naturally derived pigment; Tandem Mass Spectrometry; Vinyl-pyranoanthocyanins
• ISSN: 0308-8146; 1873-7072
• DOI: 10.1016/j.foodchem.2023.136705

•4-vinylphenols (4VPs) produced pyranoanthocyanins (PACN) efficiently.•PACN yield with 4VPs were up to 12× higher than with hydroxycinnamic acids.•Intermediate compounds suggest cycloaddition and aromatization formation mechanism.•4-vinylphenols in molar excess promoted anthocyanin degradation.•PACNs formed with 4-vinylguaiacol were redder than those formed with 4-vinylphenol. Pyranoanthocyanins are anthocyanin-derived pigments with vivid colors and enhanced stability, making them promising food colorants. We evaluated two 4-vinylphenols, decarboxylated p-coumaric (pCA) and ferulic acid (FA), as cofactors for pyranoanthocyanin formation. Cyanidin-3-glycosides from saponified black carrot were incubated with 4-vinylphenol or 4-vinylguaiacol in different anthocyanin-to-cofactor molar ratios (1:1–1:30) to form pyranoanthocyanins. Formation efficiency (45 °C, ≤96 h) was compared to their respective precursors at a 1:30 ratio. Composition changes were monitored using uHPLC-PDA-ESI-MS/MS. Pyranoanthocyanin yields with 4-vinylphenol (13.8–33.4%) were ∼12× higher than with pCA and yields with 4-vinylguaiacol (8.1–31.0%) were ∼6.5× higher than with FA. Molar ratios of 1:5 and 1:10 yielded significantly more pyranoanthocyanins. Pyranoanthocyanin formation with 4-vinylphenols followed first-order kinetics, whereas formation with hydroxycinnamic acids followed zero-order kinetics. Detection of intermediate compounds was consistent with a nucleophilic addition and aromatization formation mechanism. Overall, pyranoanthocyanin formation with 4-vinylphenols was more efficient than with hydroxycinnamic acids.