TY - JOUR
T1 - Impact of phenolic compounds in strecker aldehyde formation in wine model systems
T2 - target and untargeted analysis
AU - Monforte, A. R.
AU - Martins, S. I. F. S.
AU - Ferreira, A. C. Silva
N1 - Funding Information:
This work was supported by National Funds from Fundação para a Ciência e a Tecnologia (FCT) through Project UID/Multi/50016/2019 and also by the doctoral fellowship of Ana Rita Monforte (SFRH/BD/111889/2015).
Publisher Copyright:
Copyright © 2019 American Chemical Society.
PY - 2020/9/23
Y1 - 2020/9/23
N2 - The Strecker degradation of phenylalanine has been studied in a phenolic compound/phenylalanine wine model system. Six phenolic compounds (3,4-dihydroxybenzoic acid, gallic acid, caffeic acid, ferulic acid, catechin, and epicatechin) were compared in the formation of phenylacetaldehyde when in the presence of glucose or methylglyoxal (MG). The addition of glucose reduced the formation of Strecker aldehyde, independently of the phenolic compound. The addition of MG, on the other hand, increased phenylacetaldehyde formation for hydroxybenzoic acids and decreased phenylacetaldehyde formation for flavan-3-ols, confirming their capacity to trap the dicarbonyl compound. As a target phenolic compound, catechin was chosen to perform kinetic studies to further understand the reaction intermediates involved in the mechanism of phenylacetaldehyde formation, in particular, catechin o-quinone and catechin-MG adduct. The addition of glucose and MG increased the consumption of catechin, while a reduction in the respective o-quinone was observed, suggesting that these substrates have an impact in other reactions involving catechin. In that regard, for the first time, it was demonstrated that the catechin-MG adduct was capable of oxidizing and forming a new o-quinone, contributing to wine instability promoted by oxidation reactions.
AB - The Strecker degradation of phenylalanine has been studied in a phenolic compound/phenylalanine wine model system. Six phenolic compounds (3,4-dihydroxybenzoic acid, gallic acid, caffeic acid, ferulic acid, catechin, and epicatechin) were compared in the formation of phenylacetaldehyde when in the presence of glucose or methylglyoxal (MG). The addition of glucose reduced the formation of Strecker aldehyde, independently of the phenolic compound. The addition of MG, on the other hand, increased phenylacetaldehyde formation for hydroxybenzoic acids and decreased phenylacetaldehyde formation for flavan-3-ols, confirming their capacity to trap the dicarbonyl compound. As a target phenolic compound, catechin was chosen to perform kinetic studies to further understand the reaction intermediates involved in the mechanism of phenylacetaldehyde formation, in particular, catechin o-quinone and catechin-MG adduct. The addition of glucose and MG increased the consumption of catechin, while a reduction in the respective o-quinone was observed, suggesting that these substrates have an impact in other reactions involving catechin. In that regard, for the first time, it was demonstrated that the catechin-MG adduct was capable of oxidizing and forming a new o-quinone, contributing to wine instability promoted by oxidation reactions.
KW - Catechin
KW - Methylglyoxal
KW - O-quinones
KW - Phenylacetaldehyde
KW - Strecker degradation
UR - http://www.scopus.com/inward/record.url?scp=85091553862&partnerID=8YFLogxK
U2 - 10.1021/acs.jafc.9b02674
DO - 10.1021/acs.jafc.9b02674
M3 - Article
C2 - 31274314
AN - SCOPUS:85091553862
SN - 0021-8561
VL - 68
SP - 10281
EP - 10286
JO - Journal of Agricultural and Food Chemistry
JF - Journal of Agricultural and Food Chemistry
IS - 38
ER -