Occurrence and Antioxidant Activity of C1 Degradation Products in Cocoa

Abstract

Procyanidin C1 is by far the main flavan-3-ol trimer in cocoa. Like other flavan-3-ols, however, it suffers a lot during heat treatments such as roasting. RP-HPLC-HRMS/MS(ESI(−))analysis applied to an aqueous model medium containing commercial procyanidin C1 proved that epimerization is the main reaction involved in its degradation (accounting for 62% of degradation products). In addition to depolymerization, cocoa procyanidin C1 also proved sensitive to oxidation, yielding once- and twice-oxidized dimers. No chemical oligomer involving the native trimer was found in either model medium or cocoa, while two C1 isomers were retrieved. C1 degradation products exhibited antioxidant activity (monitored by RP-HPLC-Online TEAC) close to that of C1 (when expressed in µM TE/mg·kg−1).

Oxidation of Procyanidins with Various Degrees of Condensation: Influence on the Color-Deepening Phenomenon

“…The reconstructed ion chromatograms for m / z 863 and 861 facilitated the resolution of multiple well-separated peaks with the same mass number that correspond to positional or stereoisomers. De Taeye et al reported that procyanidin is chemically modified by food processes; , in their research, procyanidin B2 and C1, which are the dimer and trimer of epicatechin, were epimerized by heating in a model aqueous system to generate dehydrodicatechin A; however, this was not observed in our experiment. It is well-known that catechin rapidly epimerizes at the 2-position at high temperatures in an aqueous medium .…”

Polyphenols, Antioxidants, and Wound Healing of Lecythis pisonis Seed Coats

“…The compounds identified by ESI(+)FT-ICR MS, such as procyanidin and catechin, are presented in ▶ Table 1 [17][18][19][20][21][22][23][24][25][26][27][28][29][31][32][33]. Polyphenols are secondary metabolites having a common intermediate, phenylalanine, or a close precursor, shikimic acid [34] m/z 883.21008.…”

Antioxidants in Food: The Significance of Characterisation, Identification, Chemical and Biological Assays in Determining the Role of Antioxidants in Food

“…De Taeye and Kankolongo, used online HPLC/TEAC and high resolution MS techniques to follow the heat-induced degradation of procyanidin, the major flavanol-3-ol trimer extracted from cocoa [ 3 ]. Epimerization was the major process.…”