TY - JOUR
T1 - Browning of Epicatechin (EC) and Epigallocatechin (EGC) by Auto-Oxidation
AU - Tan, Junfeng
AU - De Bruijn, Wouter J.C.
AU - Van Zadelhoff, Annemiek
AU - Lin, Zhi
AU - Vincken, Jean Paul
PY - 2020/11/10
Y1 - 2020/11/10
N2 - Green tea catechins are well known for their health benefits. However, these compounds can easily be oxidized, resulting in brown color formation, even in the absence of active oxidative enzymes. Browning of catechin-rich beverages, such as green tea, during their shelf life is undesired. The mechanisms of auto-oxidation of catechins and the brown products formed are still largely unknown. Therefore, we studied auto-oxidative browning of epicatechin (EC) and epigallocatechin (EGC) in model systems. Products of EC and EGC auto-oxidation were analyzed by reversed-phase ultra-high-performance liquid chromatography with photodiode array detection coupled to mass spectrometry (RP-UHPLC-PDA-MS). In the EC model system, 11 δ-type dehydrodicatechins (DhC2s) and 18 δ-type dehydrotricatechins (DhC3s) that were related to browning could be tentatively identified by their MS2 signature fragments. In the EGC model system, auto-oxidation led to the formation of 13 dihydro-indene-carboxylic acid derivatives and 2 theaflagallins that were related to browning. Based on the products formed, we propose mechanisms for the auto-oxidative browning of EC and EGC. Furthermore, our results indicate that dimers and oligomers that possess a combination of an extended conjugated system, fused rings, and carbonyl groups are responsible for the brown color formation in the absence of oxidative enzymes.
AB - Green tea catechins are well known for their health benefits. However, these compounds can easily be oxidized, resulting in brown color formation, even in the absence of active oxidative enzymes. Browning of catechin-rich beverages, such as green tea, during their shelf life is undesired. The mechanisms of auto-oxidation of catechins and the brown products formed are still largely unknown. Therefore, we studied auto-oxidative browning of epicatechin (EC) and epigallocatechin (EGC) in model systems. Products of EC and EGC auto-oxidation were analyzed by reversed-phase ultra-high-performance liquid chromatography with photodiode array detection coupled to mass spectrometry (RP-UHPLC-PDA-MS). In the EC model system, 11 δ-type dehydrodicatechins (DhC2s) and 18 δ-type dehydrotricatechins (DhC3s) that were related to browning could be tentatively identified by their MS2 signature fragments. In the EGC model system, auto-oxidation led to the formation of 13 dihydro-indene-carboxylic acid derivatives and 2 theaflagallins that were related to browning. Based on the products formed, we propose mechanisms for the auto-oxidative browning of EC and EGC. Furthermore, our results indicate that dimers and oligomers that possess a combination of an extended conjugated system, fused rings, and carbonyl groups are responsible for the brown color formation in the absence of oxidative enzymes.
KW - catechins
KW - discoloration
KW - nonenzymatic
KW - oxidation
KW - tea
U2 - 10.1021/acs.jafc.0c05716
DO - 10.1021/acs.jafc.0c05716
M3 - Article
C2 - 33171045
AN - SCOPUS:85096568601
SN - 0021-8561
VL - 68
SP - 13879
EP - 13887
JO - Journal of Agricultural and Food Chemistry
JF - Journal of Agricultural and Food Chemistry
IS - 47
ER -