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Degradation of (-)-epicatechin and procyanidin B2 in aqueous and lipidic model systems. first evidence of "chemical" flavan-3-ol oligomers in processed cocoa.
J Agric Food Chem. 2014 Sep 10; 62(36):9002-16.JA

Abstract

Despite the key role of flavan-3-ols in many foods, very little is yet known concerning the modification of their chemical structures through food processes. Degradation of model media containing (-)-epicatechin and procyanidin B2, either separately or together, was monitored by RP-HPLC-DAD-ESI(-)-MS/MS. Medium composition (aqueous or lipidic) and temperature (60 and 90 °C) were studied. In aqueous medium at 60 °C, (-)-epicatechin was mainly epimerized to (-)-catechin, but it was also oxidized to "chemical" dimers, a "chemical" trimer, and dehydrodi(epi)catechin A. Unlike oxidation, epimerization was enhanced at 90 °C. In lipidic medium, epimerization proved slow but degradation was faster. Procyanidin B2 likewise proved able to epimerize, especially at 90 °C and in aqueous medium. At high temperature only, the interflavan linkage was cleaved, yielding the same compounds as those found in the monomer-containing model medium. Oxidation to procyanidin A2 was also evidenced. With little epimerization and slow oxidation even at 90 °C, procyanidin B2 proved more stable in lipidic medium. Synergy was also observed: in the presence of the monomer, the dimer degradation rate increased 2-fold at 60 °C. This work states for the first time the presence of newly formed flavan-3-ol oligomers in processed cocoa.

Authors+Show Affiliations

Unité de Brasserie et des Industries Alimentaires, Earth and Life Institute, ELIM, Faculté d'Ingénierie Biologique, Agronomique et Environnementale, Université catholique de Louvain , Croix du Sud, 2 bte L07.05.07, B-1348 Louvain-la-Neuve, Belgium.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

25167469

Citation

De Taeye, Cédric, et al. "Degradation of (-)-epicatechin and Procyanidin B2 in Aqueous and Lipidic Model Systems. First Evidence of "chemical" Flavan-3-ol Oligomers in Processed Cocoa." Journal of Agricultural and Food Chemistry, vol. 62, no. 36, 2014, pp. 9002-16.
De Taeye C, Cibaka ML, Jerkovic V, et al. Degradation of (-)-epicatechin and procyanidin B2 in aqueous and lipidic model systems. first evidence of "chemical" flavan-3-ol oligomers in processed cocoa. J Agric Food Chem. 2014;62(36):9002-16.
De Taeye, C., Cibaka, M. L., Jerkovic, V., & Collin, S. (2014). Degradation of (-)-epicatechin and procyanidin B2 in aqueous and lipidic model systems. first evidence of "chemical" flavan-3-ol oligomers in processed cocoa. Journal of Agricultural and Food Chemistry, 62(36), 9002-16. https://doi.org/10.1021/jf502016z
De Taeye C, et al. Degradation of (-)-epicatechin and Procyanidin B2 in Aqueous and Lipidic Model Systems. First Evidence of "chemical" Flavan-3-ol Oligomers in Processed Cocoa. J Agric Food Chem. 2014 Sep 10;62(36):9002-16. PubMed PMID: 25167469.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Degradation of (-)-epicatechin and procyanidin B2 in aqueous and lipidic model systems. first evidence of "chemical" flavan-3-ol oligomers in processed cocoa. AU - De Taeye,Cédric, AU - Cibaka,Marie-Lucie Kankolongo, AU - Jerkovic,Vesna, AU - Collin,Sonia, Y1 - 2014/08/28/ PY - 2014/8/29/entrez PY - 2014/8/29/pubmed PY - 2015/9/1/medline KW - chocolate KW - cocoa KW - conching KW - flavan-3-ol KW - lipidic medium KW - polyphenol SP - 9002 EP - 16 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 62 IS - 36 N2 - Despite the key role of flavan-3-ols in many foods, very little is yet known concerning the modification of their chemical structures through food processes. Degradation of model media containing (-)-epicatechin and procyanidin B2, either separately or together, was monitored by RP-HPLC-DAD-ESI(-)-MS/MS. Medium composition (aqueous or lipidic) and temperature (60 and 90 °C) were studied. In aqueous medium at 60 °C, (-)-epicatechin was mainly epimerized to (-)-catechin, but it was also oxidized to "chemical" dimers, a "chemical" trimer, and dehydrodi(epi)catechin A. Unlike oxidation, epimerization was enhanced at 90 °C. In lipidic medium, epimerization proved slow but degradation was faster. Procyanidin B2 likewise proved able to epimerize, especially at 90 °C and in aqueous medium. At high temperature only, the interflavan linkage was cleaved, yielding the same compounds as those found in the monomer-containing model medium. Oxidation to procyanidin A2 was also evidenced. With little epimerization and slow oxidation even at 90 °C, procyanidin B2 proved more stable in lipidic medium. Synergy was also observed: in the presence of the monomer, the dimer degradation rate increased 2-fold at 60 °C. This work states for the first time the presence of newly formed flavan-3-ol oligomers in processed cocoa. SN - 1520-5118 UR - https://www.unboundmedicine.com/medline/citation/25167469/Degradation_of_____epicatechin_and_procyanidin_B2_in_aqueous_and_lipidic_model_systems__first_evidence_of_"chemical"_flavan_3_ol_oligomers_in_processed_cocoa_ L2 - https://doi.org/10.1021/jf502016z DB - PRIME DP - Unbound Medicine ER -