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Molecules 2018, 23(3), 598; https://doi.org/10.3390/molecules23030598

Cis–Trans Configuration of Coumaric Acid Acylation Affects the Spectral and Colorimetric Properties of Anthocyanins

Department of Food Science and Technology 2015 Fyffe Ct., The Ohio State University, Columbus, OH 43210-1007, USA
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Received: 2 February 2018 / Revised: 23 February 2018 / Accepted: 4 March 2018 / Published: 7 March 2018
(This article belongs to the Special Issue Advances in Anthocyanin Research 2018)
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Abstract

The color expression of anthocyanins can be affected by a variety of environmental factors and structural characteristics. Anthocyanin acylation (type and number of acids) is known to be key, but the influence of acyl isomers (with unique stereochemistries) remains to be explored. The objective of this study was to investigate the effects of cis–trans configuration of the acylating group on the spectral and colorimetric properties of anthocyanins. Petunidin-3-rutinoside-5-glucoside (Pt-3-rut-5-glu) and Delphinidin-3-rutinoside-5-glucoside (Dp-3-rut-5-glu) and their cis and trans coumaroylated derivatives were isolated from black goji and eggplant, diluted in pH 1–9 buffers, and analyzed spectrophotometrically (380–700 nm) and colorimetrically (CIELAB) during 72 h of storage (25 °C, dark). The stereochemistry of the acylating group strongly impacted the spectra, color, and stability of the Dp and Pt anthocyanins. Cis acylated pigments exhibited the greatest λmax in all pH, as much as 66 nm greater than their trans counterparts, showing bluer hues. Cis acylation seemed to reduce hydration across pH, increasing color intensity, while trans acylation generally improved color retention over time. Dp-3-cis-p-cou-rut-5-glu exhibited blue hues even in pH 5 (C*ab = 10, hab = 256°) where anthocyanins are typically colorless. Cis or trans double bond configurations of the acylating group affected anthocyanin spectral and stability properties. View Full-Text
Keywords: delphinidin; petunidin; natural color; isomers; cis acylation; trans acylation; Solanum melongena L.; Lycium ruthenicum delphinidin; petunidin; natural color; isomers; cis acylation; trans acylation; Solanum melongena L.; Lycium ruthenicum
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).
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Sigurdson, G.T.; Tang, P.; Giusti, M.M. Cis–Trans Configuration of Coumaric Acid Acylation Affects the Spectral and Colorimetric Properties of Anthocyanins. Molecules 2018, 23, 598.

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