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

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 t...

Full description

Saved in:
Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2018-03, Vol.23 (3), p.598
Main Authors: Sigurdson, Gregory T, Tang, Peipei, Giusti, M Mónica
Format: Article
Language:English
Subjects:
Acids
Acylation
Anthocyanins
Anthocyanins - chemistry
Chromatography, High Pressure Liquid
cis acylation
Color
Colorimetry
Configurations
Coumaric acid
Coumaric Acids - chemistry
delphinidin
Environmental factors
Food products
Fruits
Hydration
Hydrogen-Ion Concentration
Isomerism
Isomers
Lycium ruthenicum
natural color
petunidin
Pigments
Pigments, Biological - chemistry
Solanum melongena L
Spectra
Spectrophotometry
Spectrum Analysis
Stability
Stereochemistry
trans acylation
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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 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 and 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. acylated pigments exhibited the greatest λ in all pH, as much as 66 nm greater than their counterparts, showing bluer hues. acylation seemed to reduce hydration across pH, increasing color intensity, while acylation generally improved color retention over time. Dp-3- -cou-rut-5-glu exhibited blue hues even in pH 5 (C* = 10, h = 256°) where anthocyanins are typically colorless. or double bond configurations of the acylating group affected anthocyanin spectral and stability properties.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules23030598