Details
| Originalsprache | Englisch |
|---|---|
| Aufsatznummer | 143379 |
| Fachzeitschrift | Food chemistry |
| Jahrgang | 476 |
| Frühes Online-Datum | 14 Feb. 2025 |
| Publikationsstatus | Veröffentlicht - 1 Juni 2025 |
| Extern publiziert | Ja |
Abstract
Polyphenols can be widely found in plants and plant-based food. Polyphenols with an ortho-dihydroxy structure, such as caffeic acid (CA), can easily be oxidized to their ortho-quinones. These quinones can react with nucleophilic side chains of proteins, such as the thiol group in cysteine (Cys), and form adducts that can affect the structure and function of these proteins. Individual adducts have been described qualitatively, but quantitative analysis has been hampered by the poor stability of the adducts during sample preparation. In this study, 2-S-cysteinyl caffeic acid was synthesized either in a free or protein-bound form. A one-enzyme hydrolysis was developed using Pronase E. It yielded a hydrolysis rate of 97 % calculated via phenylalanine release. A recovery rate of 2-S-cysteinyl caffeic acid (2-CCA) of 64 % after hydrolysis was achieved when buffer systems containing borate anions were used. The formation of 2-CCA in bovine serum albumin (BSA) incubated with CA was shown.
ASJC Scopus Sachgebiete
- Chemie (insg.)
- Analytische Chemie
- Agrar- und Biowissenschaften (insg.)
- Lebensmittelwissenschaften
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in: Food chemistry, Jahrgang 476, 143379, 01.06.2025.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review
}
TY - JOUR
T1 - Release of protein-bound adducts of cysteine residues with caffeic acid by a modified enzymatic hydrolysis method using Pronase E
AU - Krax, Raphaela
AU - Schulte, Leon
AU - Fischer, Annik
AU - Hellwig, Michael
N1 - Publisher Copyright: © 2025 The Authors
PY - 2025/6/1
Y1 - 2025/6/1
N2 - Polyphenols can be widely found in plants and plant-based food. Polyphenols with an ortho-dihydroxy structure, such as caffeic acid (CA), can easily be oxidized to their ortho-quinones. These quinones can react with nucleophilic side chains of proteins, such as the thiol group in cysteine (Cys), and form adducts that can affect the structure and function of these proteins. Individual adducts have been described qualitatively, but quantitative analysis has been hampered by the poor stability of the adducts during sample preparation. In this study, 2-S-cysteinyl caffeic acid was synthesized either in a free or protein-bound form. A one-enzyme hydrolysis was developed using Pronase E. It yielded a hydrolysis rate of 97 % calculated via phenylalanine release. A recovery rate of 2-S-cysteinyl caffeic acid (2-CCA) of 64 % after hydrolysis was achieved when buffer systems containing borate anions were used. The formation of 2-CCA in bovine serum albumin (BSA) incubated with CA was shown.
AB - Polyphenols can be widely found in plants and plant-based food. Polyphenols with an ortho-dihydroxy structure, such as caffeic acid (CA), can easily be oxidized to their ortho-quinones. These quinones can react with nucleophilic side chains of proteins, such as the thiol group in cysteine (Cys), and form adducts that can affect the structure and function of these proteins. Individual adducts have been described qualitatively, but quantitative analysis has been hampered by the poor stability of the adducts during sample preparation. In this study, 2-S-cysteinyl caffeic acid was synthesized either in a free or protein-bound form. A one-enzyme hydrolysis was developed using Pronase E. It yielded a hydrolysis rate of 97 % calculated via phenylalanine release. A recovery rate of 2-S-cysteinyl caffeic acid (2-CCA) of 64 % after hydrolysis was achieved when buffer systems containing borate anions were used. The formation of 2-CCA in bovine serum albumin (BSA) incubated with CA was shown.
KW - 2-S-Cysteinyl caffeic acid
KW - Bovine serum albumin
KW - Pronase E
KW - Protein hydrolysis
KW - Protein-polyphenol interaction
UR - http://www.scopus.com/inward/record.url?scp=85217904601&partnerID=8YFLogxK
U2 - 10.1016/j.foodchem.2025.143379
DO - 10.1016/j.foodchem.2025.143379
M3 - Article
AN - SCOPUS:85217904601
VL - 476
JO - Food chemistry
JF - Food chemistry
SN - 0308-8146
M1 - 143379
ER -