Characterization of new flavan-3-ol derivatives in fermented cocoa beans

Two series of compounds showing mass signals at m/z 605 and 893 (negative ionization mode) have been detected in fermented cocoa beans. This study objective is to identify these mass signals and characterize their structure in fermented cocoa samples. Our hypothesis is that these signals may correspond to ethyl-bridged flavan-3-ols resulting from flavan-3-ol condensation with acetaldehyde which is a microbial metabolite. Mass spectrometry was used to compare the retention times and mass fragmentation patterns between a model solution using epicatechin and procyanidin dimer B2, the major flavan-3-ols of cocoa, as precursors and extracts of fermented cocoa. Their identification was confirmed: four isomers of ethyl-linked epicatechin as well as several isomers of epicatechin-ethyl-procyanidin B2, in which B2 was mostly linked through its upper unit, were characterized in cocoa. This study demonstrates the presence of flavan-3-ol acetaldehyde condensation products in fermented cocoa beans and provides the first report of epicatechin-ethyl-procyanidin B2.

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Main Authors: Fayeulle, Noémie, Vallverdu-Queralt, Anna, Meudec, Emmanuelle, Hue, Clotilde, Boulanger, Renaud, Cheynier, Véronique, Sommerer, Nicolas
Format: article biblioteca
Language:eng
Subjects:Q04 - Composition des produits alimentaires, Theobroma cacao, composition chimique, flaveur, composé de la flaveur, http://aims.fao.org/aos/agrovoc/c_7713, http://aims.fao.org/aos/agrovoc/c_1794, http://aims.fao.org/aos/agrovoc/c_10893, http://aims.fao.org/aos/agrovoc/c_28309,
Online Access:http://agritrop.cirad.fr/587940/
http://agritrop.cirad.fr/587940/1/1-s2.0-S0308814618305752-main.pdf
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spelling dig-cirad-fr-5879402024-01-29T01:01:31Z http://agritrop.cirad.fr/587940/ http://agritrop.cirad.fr/587940/ Characterization of new flavan-3-ol derivatives in fermented cocoa beans. Fayeulle Noémie, Vallverdu-Queralt Anna, Meudec Emmanuelle, Hue Clotilde, Boulanger Renaud, Cheynier Véronique, Sommerer Nicolas. 2018. Food Chemistry, 259 : 207-212.https://doi.org/10.1016/j.foodchem.2018.03.133 <https://doi.org/10.1016/j.foodchem.2018.03.133> Characterization of new flavan-3-ol derivatives in fermented cocoa beans Fayeulle, Noémie Vallverdu-Queralt, Anna Meudec, Emmanuelle Hue, Clotilde Boulanger, Renaud Cheynier, Véronique Sommerer, Nicolas eng 2018 Food Chemistry Q04 - Composition des produits alimentaires Theobroma cacao composition chimique flaveur composé de la flaveur http://aims.fao.org/aos/agrovoc/c_7713 http://aims.fao.org/aos/agrovoc/c_1794 http://aims.fao.org/aos/agrovoc/c_10893 http://aims.fao.org/aos/agrovoc/c_28309 Two series of compounds showing mass signals at m/z 605 and 893 (negative ionization mode) have been detected in fermented cocoa beans. This study objective is to identify these mass signals and characterize their structure in fermented cocoa samples. Our hypothesis is that these signals may correspond to ethyl-bridged flavan-3-ols resulting from flavan-3-ol condensation with acetaldehyde which is a microbial metabolite. Mass spectrometry was used to compare the retention times and mass fragmentation patterns between a model solution using epicatechin and procyanidin dimer B2, the major flavan-3-ols of cocoa, as precursors and extracts of fermented cocoa. Their identification was confirmed: four isomers of ethyl-linked epicatechin as well as several isomers of epicatechin-ethyl-procyanidin B2, in which B2 was mostly linked through its upper unit, were characterized in cocoa. This study demonstrates the presence of flavan-3-ol acetaldehyde condensation products in fermented cocoa beans and provides the first report of epicatechin-ethyl-procyanidin B2. article info:eu-repo/semantics/article Journal Article info:eu-repo/semantics/publishedVersion http://agritrop.cirad.fr/587940/1/1-s2.0-S0308814618305752-main.pdf text Cirad license info:eu-repo/semantics/restrictedAccess https://agritrop.cirad.fr/mention_legale.html https://doi.org/10.1016/j.foodchem.2018.03.133 10.1016/j.foodchem.2018.03.133 info:eu-repo/semantics/altIdentifier/doi/10.1016/j.foodchem.2018.03.133 info:eu-repo/semantics/altIdentifier/purl/https://doi.org/10.1016/j.foodchem.2018.03.133
institution CIRAD FR
collection DSpace
country Francia
countrycode FR
component Bibliográfico
access En linea
databasecode dig-cirad-fr
tag biblioteca
region Europa del Oeste
libraryname Biblioteca del CIRAD Francia
language eng
topic Q04 - Composition des produits alimentaires
Theobroma cacao
composition chimique
flaveur
composé de la flaveur
http://aims.fao.org/aos/agrovoc/c_7713
http://aims.fao.org/aos/agrovoc/c_1794
http://aims.fao.org/aos/agrovoc/c_10893
http://aims.fao.org/aos/agrovoc/c_28309
Q04 - Composition des produits alimentaires
Theobroma cacao
composition chimique
flaveur
composé de la flaveur
http://aims.fao.org/aos/agrovoc/c_7713
http://aims.fao.org/aos/agrovoc/c_1794
http://aims.fao.org/aos/agrovoc/c_10893
http://aims.fao.org/aos/agrovoc/c_28309
spellingShingle Q04 - Composition des produits alimentaires
Theobroma cacao
composition chimique
flaveur
composé de la flaveur
http://aims.fao.org/aos/agrovoc/c_7713
http://aims.fao.org/aos/agrovoc/c_1794
http://aims.fao.org/aos/agrovoc/c_10893
http://aims.fao.org/aos/agrovoc/c_28309
Q04 - Composition des produits alimentaires
Theobroma cacao
composition chimique
flaveur
composé de la flaveur
http://aims.fao.org/aos/agrovoc/c_7713
http://aims.fao.org/aos/agrovoc/c_1794
http://aims.fao.org/aos/agrovoc/c_10893
http://aims.fao.org/aos/agrovoc/c_28309
Fayeulle, Noémie
Vallverdu-Queralt, Anna
Meudec, Emmanuelle
Hue, Clotilde
Boulanger, Renaud
Cheynier, Véronique
Sommerer, Nicolas
Characterization of new flavan-3-ol derivatives in fermented cocoa beans
description Two series of compounds showing mass signals at m/z 605 and 893 (negative ionization mode) have been detected in fermented cocoa beans. This study objective is to identify these mass signals and characterize their structure in fermented cocoa samples. Our hypothesis is that these signals may correspond to ethyl-bridged flavan-3-ols resulting from flavan-3-ol condensation with acetaldehyde which is a microbial metabolite. Mass spectrometry was used to compare the retention times and mass fragmentation patterns between a model solution using epicatechin and procyanidin dimer B2, the major flavan-3-ols of cocoa, as precursors and extracts of fermented cocoa. Their identification was confirmed: four isomers of ethyl-linked epicatechin as well as several isomers of epicatechin-ethyl-procyanidin B2, in which B2 was mostly linked through its upper unit, were characterized in cocoa. This study demonstrates the presence of flavan-3-ol acetaldehyde condensation products in fermented cocoa beans and provides the first report of epicatechin-ethyl-procyanidin B2.
format article
topic_facet Q04 - Composition des produits alimentaires
Theobroma cacao
composition chimique
flaveur
composé de la flaveur
http://aims.fao.org/aos/agrovoc/c_7713
http://aims.fao.org/aos/agrovoc/c_1794
http://aims.fao.org/aos/agrovoc/c_10893
http://aims.fao.org/aos/agrovoc/c_28309
author Fayeulle, Noémie
Vallverdu-Queralt, Anna
Meudec, Emmanuelle
Hue, Clotilde
Boulanger, Renaud
Cheynier, Véronique
Sommerer, Nicolas
author_facet Fayeulle, Noémie
Vallverdu-Queralt, Anna
Meudec, Emmanuelle
Hue, Clotilde
Boulanger, Renaud
Cheynier, Véronique
Sommerer, Nicolas
author_sort Fayeulle, Noémie
title Characterization of new flavan-3-ol derivatives in fermented cocoa beans
title_short Characterization of new flavan-3-ol derivatives in fermented cocoa beans
title_full Characterization of new flavan-3-ol derivatives in fermented cocoa beans
title_fullStr Characterization of new flavan-3-ol derivatives in fermented cocoa beans
title_full_unstemmed Characterization of new flavan-3-ol derivatives in fermented cocoa beans
title_sort characterization of new flavan-3-ol derivatives in fermented cocoa beans
url http://agritrop.cirad.fr/587940/
http://agritrop.cirad.fr/587940/1/1-s2.0-S0308814618305752-main.pdf
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