Procyanidin A2 and Its Degradation Products in Raw, Fermented, and Roasted Cocoa

被引:30
作者
De Taeye, Cedric [1 ]
Caullet, Gilles [1 ]
Evina, Victor Jos Eyamo [1 ]
Collin, Sonia [1 ]
机构
[1] Catholic Univ Louvain, Fac Bioingenieurs, Unite Brasserie & Ind Alimentaires, Earth & Life Inst,ELIM, 2 Bte L07-05-07, B-1348 Louvain La Neuve, Belgium
关键词
procyanidin A2; epimers; flavan-3-ol; cocoa fermentation; cyanidin; CONDENSED TANNINS; PROANTHOCYANIDINS; PERICARP; ANTHOCYANINS; OXIDATION; IMPACT; DIMER;
D O I
10.1021/acs.jafc.6b05262
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
Cocoa is known as an important source of flavan-3-ols, but their fate "from the bean to the bar" is not yet clear. Here, procyanidin A2 found in native cocoa beans (9-13 mg/kg) appeared partially epimerized into A2(E1) through fermentation, whereas a second epimer (A2(E2)) emerged after roasting. At m/z 575, dehydrodiepicatechin A was revealed to be the major HPLC peak before fermentation, whereas F1, a marker of well-conducted fermentations, becomes the most intense after roasting.RP-HPLC-ESI(-)-HRMS/MS analysis performed on a procyanidin A2 model medium after 12 h at 90 degrees C revealed many more degradation products than those identified in fermented cocoa, including the last epimer of A2, A2 open structure intermediates (m/z 577), and oxidized A -type dimers (m/z 573).
引用
收藏
页码:1715 / 1723
页数:9
相关论文
共 41 条
[1]   Green tea polyphenol epigallocatechin-3-gallate differentially modulates nuclear factor κB in cancer cells versus normal cells [J].
Ahmad, N ;
Gupta, S ;
Mukhtar, H .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 2000, 376 (02) :338-346
[2]  
[Anonymous], 2011, POLYPHENOLS PROCEDES
[3]   Free radicals and grape seed proanthocyanidin extract: importance in human health and disease prevention [J].
Bagchi, D ;
Bagchi, M ;
Stohs, SJ ;
Das, DK ;
Ray, SD ;
Kuszynski, CA ;
Joshi, SS ;
Pruess, HG .
TOXICOLOGY, 2000, 148 (2-3) :187-197
[4]   Effects of sublethal attack by a sucking insect, Hyalymenus tarsatus, on Sesbania drummondii seeds:: Impact on some seed traits related to fitness [J].
Ceballos, L ;
Andary, C ;
Delescluse, M ;
Gibernau, M ;
McKey, D ;
Hossaert-Mckey, M .
ECOSCIENCE, 2002, 9 (01) :28-36
[5]   Effect of the number of flavanol units on the antioxidant activity of procyanidin fractions isolated from chocolate [J].
Counet, C ;
Collin, S .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2003, 51 (23) :6816-6822
[6]   Fate of Anthocyanins through Cocoa Fermentation. Emergence of New Polyphenolic Dimers [J].
De Taeye, Cedric ;
Evina, Victor Jos Eyamo ;
Caullet, Gilles ;
Niemenak, Nicolas ;
Collin, Sonia .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2016, 64 (46) :8876-8885
[7]   Degradation of (-)-Epicatechin and Procyanidin B2 in Aqueous and Lipidic Model Systems. First Evidence of "Chemical" Flavan-3-ol Oligomers in Processed Cocoa [J].
De Taeye, Cedric ;
Cibaka, Marie-Lucie Kankolongo ;
Jerkovic, Vesna ;
Collin, Sonia .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2014, 62 (36) :9002-9016
[8]   Formation of anthocyanin-flavanol adducts in model solutions [J].
Dueñas, M ;
Fulcrand, H ;
Cheynier, V .
ANALYTICA CHIMICA ACTA, 2006, 563 (1-2) :15-25
[9]   Influence of acetic and lactic acids on cocoa flavan-3-ol degradation through fermentation-like incubations [J].
Evina, Victor Jos Eyamo ;
De Taeye, Cedric ;
Niemenak, Nicolas ;
Youmbi, Emmanuel ;
Collin, Sonia .
LWT-FOOD SCIENCE AND TECHNOLOGY, 2016, 68 :514-522
[10]   The structure of cranberry proanthocyanidins which inhibit adherence of uropathogenic P-fimbriated Escherichia coli in vitro [J].
Foo, LY ;
Lu, YR ;
Howell, AB ;
Vorsa, N .
PHYTOCHEMISTRY, 2000, 54 (02) :173-181