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Reactions of anthocyanins and o-quinones in model systems and foods Open Access

Descriptions

Other title
Subject/Keyword
nucleophilic
amino acids
beta-carotene
browning
apricot
phenolics
anthocyanins
Type of item
Thesis
Degree grantor
University of Alberta
Author or creator
Afanas'yev, Dmytro
Supervisor and department
Schieber, Andreas (Agricultural, Food and Nutritional Science)
Examining committee member and department
Vederas, John (Chemistry)
Ozga, Jocelyn (Agricultural, Food and Nutritional Science)
Department
Department of Agricultural, Food and Nutritional Science
Specialization

Date accepted
2010-09-09T19:19:30Z
Graduation date
2010-11
Degree
Master of Science
Degree level
Master's
Abstract
Molecules of anthocyanins and quinones possess distinctive electrophilic character, which is demonstrated by their facile reactions with nucleophiles such as sulfite, thiols, amines and water. In food systems, one of their likely targets would be nucleophilic centers in the side chains of amino acids. Our experiments revealed that on a short-term exposure (1 – 72 h) to free amino acids in solutions with pH < 7 glycosides of cyanidin and quinones of phenolic acids did not yield nucleophilic addition products with most of the amino acids. A notable exception was cysteine, which reacted with oxidized phenolic acids and caused anthocyanin bleaching at elevated temperature. Thermodynamic aspects of the nucleophilic addition reactions were investigated with the aid of computational chemistry. We have also found that enzymatic browning in apricot puree does not lead to trans-cis β-carotene isomerization, contrary to some previous reports. Increased availability of β-carotene for extraction was recorded for browned apple- and pear-apricot purees in comparison with the non-browned purees.
Language
English
DOI
doi:10.7939/R3DD8R
Rights
License granted by Dmytro Afanas'yev (afanasye@ualberta.ca) on 2010-09-09T16:37:39Z (GMT): Permission is hereby granted to the University of Alberta Libraries to reproduce single copies of this thesis and to lend or sell such copies for private, scholarly or scientific research purposes only. Where the thesis is converted to, or otherwise made available in digital form, the University of Alberta will advise potential users of the thesis of the above terms. The author reserves all other publication and other rights in association with the copyright in the thesis, and except as herein provided, neither the thesis nor any substantial portion thereof may be printed or otherwise reproduced in any material form whatsoever without the author's prior written permission.
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