Evaluating Pyranoanthocyanins as Innovative, Naturally Derived Colorants for Foods

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2024-03

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Abstract

A food’s color plays a key role in consumer perception and a product’s success. While many nature derived colorants, like anthocyanins in fruits and vegetables, are limited in their application due to stability challenges, pyranoanthocyanins are emerging as promising, more stable options. Pyranoanthocyanins are known for producing the bold, stable color of aged wine, and they can be formed by mixing anthocyanin-containing extracts (i.e. grape, blueberry) with small molecule cofactors. With this formation process, a large number of diverse pyranoanthocyanins can be formed. The purpose of our study was to systematically characterize how the chemical structure of pyranoanthocyanins (the B ring, E ring, and C3 glycosylation) influence their coloring characteristics at pH 3 buffer. Pyranoanthocyanins with the desired chemical structures were selectively formed following previously reported methods from different anthocyanin sources (elderberry, aronia, black carrot, Berberis boliviana) and hydroxycinnamic acid derived cofactors. Pyranoanthocyanin identities were verified with uHPLC-PDA-ESI-MS/MS, and each pyranoanthocyanin was isolated with semi-preparatory HPLC, dried, and dissolved into pH 3 KCl (0.025 M) buffers at 40 µM concentration. UV-vis spectra were measured from 260–700 nm. A total of 13 unique pyranoanthocyanins were successfully formed with different patterns of hydroxyl (OH), methoxy (OCH3), and sugar substitutions. The pyranoanthocyanins all had hypsochromic shifts in the lambda vis-max compared with the parent anthocyanins, producing more vibrant yellow, orange, and red colors in contrast to pale pink produced by the anthocyanins at pH 3. Both B ring and E ring substitutions affected the color with cyanidin derived pyranoanthocyanins (B ring) producing more yellow/orange color (hypsochromic lambda vis-max) compared to those formed from malvidin anthocyanins, and the 10-p-hydroxyphenyl-PACNs (E ring) producing the most yellow/orange color. Glycosylation had a small but noticeable effect on the color with the two disaccharides evaluated producing lower intensity color with lower lambda vis-max values than the two monosaccharides and the trisaccharide. Our results highlighted the versatility of pyranoanthocyanins as nature derived colors as they could form from many anthocyanin-rich extracts and produced a range of colors at pH 3. Their bright, vibrant colors are promising for their application as food colorants.

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Poster Division: Food, Agricultural, and Environmental Sciences (FAES): 3rd Place (The Ohio State University Edward F. Hayes Advanced Research Forum)

Keywords

Food Chemistry, Anthocyanin, Nature Derived Color, Pyranoanthocyanin, Structure-function

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