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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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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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 |
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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 |
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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 |
work_keys_str_mv |
AT fayeullenoemie characterizationofnewflavan3olderivativesinfermentedcocoabeans AT vallverduqueraltanna characterizationofnewflavan3olderivativesinfermentedcocoabeans AT meudecemmanuelle characterizationofnewflavan3olderivativesinfermentedcocoabeans AT hueclotilde characterizationofnewflavan3olderivativesinfermentedcocoabeans AT boulangerrenaud characterizationofnewflavan3olderivativesinfermentedcocoabeans AT cheynierveronique characterizationofnewflavan3olderivativesinfermentedcocoabeans AT sommerernicolas characterizationofnewflavan3olderivativesinfermentedcocoabeans |
_version_ |
1792499488607174656 |