Comparing the thermal stability of 10-carboxy-, 10-methyl-, and 10-catechyl-pyranocyanidin-3-glucosides and their precursor, cyanidin-3-glucoside

Danielle M Voss; Gonzalo Miyagusuku-Cruzado; M Mónica Giusti

doi:10.1038/s41538-022-00131-9

Comparing the thermal stability of 10-carboxy-, 10-methyl-, and 10-catechyl-pyranocyanidin-3-glucosides and their precursor, cyanidin-3-glucoside

NPJ Sci Food. 2022 Feb 18;6(1):16. doi: 10.1038/s41538-022-00131-9.

Authors

Danielle M Voss¹, Gonzalo Miyagusuku-Cruzado¹, M Mónica Giusti²

Affiliations

¹ Department of Food Science and Technology, The Ohio State University, 2015 Fyffe Road, Columbus, OH, 43210-1007, USA.
² Department of Food Science and Technology, The Ohio State University, 2015 Fyffe Road, Columbus, OH, 43210-1007, USA. giusti.6@osu.edu.

Abstract

Pyranoanthocyanins are vibrant, naturally derived pigments formed by the reaction of an anthocyanin with a cofactor containing a partially negatively charged carbon. This study compared the thermal stability and degradation products of 10-carboxy-pyranocyanidin-3-glucoside (pyruvic acid cofactor), 10-methyl-pyranocyanidin-3-glucoside (acetone cofactor), and 10-catechyl-pyranocyanidin-3-glucoside (caffeic acid cofactor) with their anthocyanin precursor to evaluate the role of the pyranoanthocyanin C₁₀ substitution on stability. Pyranoanthocyanins exhibited absorbance half-lives ~2.1-8.6 times greater than cyanidin-3-glucoside, with ~15-52% of their original pigment remaining after 12 h of 90 °C heating at pH 3.0. 10-Methyl-pyranocyanidin-3-glucoside was the most stable (p < 0.01) based on UHPLC-PDA analysis, while 10-catechyl-pyranocyanidin-3-glucoside had the most stable color in part due to contribution from a colored degradation compound. Protocatechuic acid formed in all heated samples, which suggested a similar degradation mechanism among pigments. In conclusion, the C₁₀ substitution impacted the extent of pyranoanthocyanin stability and the degradation compounds formed.

Abstract

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