2014
DOI: 10.1021/jf502016z
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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

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" di… Show more

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Cited by 39 publications
(41 citation statements)
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“…As previously observed for B2 [18], depolymerization occurred, leading here to procyanidin B2 (compound 12 ) and (−)-epicatechin ( 6 ). Once created, epimerization also took place both on monomers and on dimers, yielding (−)-catechin ( 5 ) and epimers of B2 ( 10 , 11, and 13 ), respectively (Figure 1a,b).…”
Section: Resultssupporting
confidence: 75%
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“…As previously observed for B2 [18], depolymerization occurred, leading here to procyanidin B2 (compound 12 ) and (−)-epicatechin ( 6 ). Once created, epimerization also took place both on monomers and on dimers, yielding (−)-catechin ( 5 ) and epimers of B2 ( 10 , 11, and 13 ), respectively (Figure 1a,b).…”
Section: Resultssupporting
confidence: 75%
“…As for A2, which has been found in a model B2 degradation medium [18], oxidation occurred on procyanidin C1, leading to two compounds ( 38 and 39 , Table 1) monitored in ESI-(−) at m / z = 863 (Figure 1d). This oxidation occurred either between two extension units ((−)-epicatechin-(C4-C8, C2-O-C7)-(−)-epicatechin-(C4-C8)-(−)-epicatechin, also known as cinnamtannin B1) or with the terminal unit ((−)-epicatechin-(C4-C8)-(-)-epicatechin-(C4-C8, C2-O-C7)-(−)-epicatechin).…”
Section: Resultsmentioning
confidence: 84%
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