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Article

Influence of the Anthocyanin and Cofactor Structure on the Formation Efficiency of Naturally Derived Pyranoanthocyanins

Department of Food Science and Technology, The Ohio State University, 2015 Fyffe Rd., Columbus, OH 43210 1007, USA
*
Author to whom correspondence should be addressed.
These authors contributed equally to this work.
Academic Editor: Maurizio Battino
Int. J. Mol. Sci. 2021, 22(13), 6708; https://doi.org/10.3390/ijms22136708
Received: 14 May 2021 / Revised: 11 June 2021 / Accepted: 17 June 2021 / Published: 23 June 2021
(This article belongs to the Collection Feature Papers in Bioactives and Nutraceuticals)
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. View Full-Text
Keywords: hydroxyphenyl-pyranoanthocyanins; naturally derived pigments; accelerated formation; 10-catechyl-pyranoanthocyanins hydroxyphenyl-pyranoanthocyanins; naturally derived pigments; accelerated formation; 10-catechyl-pyranoanthocyanins
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MDPI and ACS Style

Miyagusuku-Cruzado, G.; Voss, D.M.; Giusti, M.M. Influence of the Anthocyanin and Cofactor Structure on the Formation Efficiency of Naturally Derived Pyranoanthocyanins. Int. J. Mol. Sci. 2021, 22, 6708. https://doi.org/10.3390/ijms22136708

AMA Style

Miyagusuku-Cruzado G, Voss DM, Giusti MM. Influence of the Anthocyanin and Cofactor Structure on the Formation Efficiency of Naturally Derived Pyranoanthocyanins. International Journal of Molecular Sciences. 2021; 22(13):6708. https://doi.org/10.3390/ijms22136708

Chicago/Turabian Style

Miyagusuku-Cruzado, Gonzalo, Danielle M. Voss, and M. M. Giusti 2021. "Influence of the Anthocyanin and Cofactor Structure on the Formation Efficiency of Naturally Derived Pyranoanthocyanins" International Journal of Molecular Sciences 22, no. 13: 6708. https://doi.org/10.3390/ijms22136708

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