Covalent bonding of 4-methylcatechol to β-lactoglobulin results in the release of cysteine-4-methylcatechol adducts after in vitro digestion

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Standard

Covalent bonding of 4-methylcatechol to β-lactoglobulin results in the release of cysteine-4-methylcatechol adducts after in vitro digestion. / Waqar, Khadija; Engholm-Keller, Kasper; Joehnke, Marcel S.; Chatterton, Dereck E.W.; Poojary, Mahesha M.; Lund, Marianne N.

I: Food Chemistry, Bind 397, 133775, 2022.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Harvard

Waqar, K, Engholm-Keller, K, Joehnke, MS, Chatterton, DEW, Poojary, MM & Lund, MN 2022, 'Covalent bonding of 4-methylcatechol to β-lactoglobulin results in the release of cysteine-4-methylcatechol adducts after in vitro digestion', Food Chemistry, bind 397, 133775. https://doi.org/10.1016/j.foodchem.2022.133775

APA

Waqar, K., Engholm-Keller, K., Joehnke, M. S., Chatterton, D. E. W., Poojary, M. M., & Lund, M. N. (2022). Covalent bonding of 4-methylcatechol to β-lactoglobulin results in the release of cysteine-4-methylcatechol adducts after in vitro digestion. Food Chemistry, 397, [133775]. https://doi.org/10.1016/j.foodchem.2022.133775

Vancouver

Waqar K, Engholm-Keller K, Joehnke MS, Chatterton DEW, Poojary MM, Lund MN. Covalent bonding of 4-methylcatechol to β-lactoglobulin results in the release of cysteine-4-methylcatechol adducts after in vitro digestion. Food Chemistry. 2022;397. 133775. https://doi.org/10.1016/j.foodchem.2022.133775

Author

Waqar, Khadija ; Engholm-Keller, Kasper ; Joehnke, Marcel S. ; Chatterton, Dereck E.W. ; Poojary, Mahesha M. ; Lund, Marianne N. / Covalent bonding of 4-methylcatechol to β-lactoglobulin results in the release of cysteine-4-methylcatechol adducts after in vitro digestion. I: Food Chemistry. 2022 ; Bind 397.

Bibtex

@article{6a7f2bd05efa487698263641c03b8efc,
title = "Covalent bonding of 4-methylcatechol to β-lactoglobulin results in the release of cysteine-4-methylcatechol adducts after in vitro digestion",
abstract = "Protein-polyphenol adducts are formed upon covalent bonding between oxidized polyphenols and proteins. 4-Methylcatechol (4MC) is a polyphenol with origin in coffee and is oxidized to 4-methylbenzoquinone (4MBQ) under conditions used during food processing. The present study characterizes 4MBQ-induced covalent modifications on β-lactoglobulin (β-LG) from bovine milk, (henceforth β-LQ) and the effect on protein digestibility. Significant thiol and amine loss was found in β-LQ compared to β-LG. Site-specific 4MBQ-induced modifications were identified on Cys, Lys, Arg, His and Trp in β-LQ. No significant differences between β-LG and β-LQ on in vitro digestibility were observed by assessment with SDS-PAGE, degree of hydrolysis and LC-MS/MS unmodified peptide intensities. Cys-4MC adduct (1.7 ± 0.1 µmol/g) was released from β-LQ after in vitro digestion. Thus, it is relevant to investigate how released Cys-4MC adducts are absorbed in vivo in future studies.",
keywords = "4-methylbenzoquinone, Amino acid-polyphenol adducts, Michael addition reaction, Polyphenols, Protein-polyphenol bonding, Whey protein",
author = "Khadija Waqar and Kasper Engholm-Keller and Joehnke, {Marcel S.} and Chatterton, {Dereck E.W.} and Poojary, {Mahesha M.} and Lund, {Marianne N.}",
note = "Publisher Copyright: {\textcopyright} 2022 The Authors",
year = "2022",
doi = "10.1016/j.foodchem.2022.133775",
language = "English",
volume = "397",
journal = "Food Chemistry",
issn = "0308-8146",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Covalent bonding of 4-methylcatechol to β-lactoglobulin results in the release of cysteine-4-methylcatechol adducts after in vitro digestion

AU - Waqar, Khadija

AU - Engholm-Keller, Kasper

AU - Joehnke, Marcel S.

AU - Chatterton, Dereck E.W.

AU - Poojary, Mahesha M.

AU - Lund, Marianne N.

N1 - Publisher Copyright: © 2022 The Authors

PY - 2022

Y1 - 2022

N2 - Protein-polyphenol adducts are formed upon covalent bonding between oxidized polyphenols and proteins. 4-Methylcatechol (4MC) is a polyphenol with origin in coffee and is oxidized to 4-methylbenzoquinone (4MBQ) under conditions used during food processing. The present study characterizes 4MBQ-induced covalent modifications on β-lactoglobulin (β-LG) from bovine milk, (henceforth β-LQ) and the effect on protein digestibility. Significant thiol and amine loss was found in β-LQ compared to β-LG. Site-specific 4MBQ-induced modifications were identified on Cys, Lys, Arg, His and Trp in β-LQ. No significant differences between β-LG and β-LQ on in vitro digestibility were observed by assessment with SDS-PAGE, degree of hydrolysis and LC-MS/MS unmodified peptide intensities. Cys-4MC adduct (1.7 ± 0.1 µmol/g) was released from β-LQ after in vitro digestion. Thus, it is relevant to investigate how released Cys-4MC adducts are absorbed in vivo in future studies.

AB - Protein-polyphenol adducts are formed upon covalent bonding between oxidized polyphenols and proteins. 4-Methylcatechol (4MC) is a polyphenol with origin in coffee and is oxidized to 4-methylbenzoquinone (4MBQ) under conditions used during food processing. The present study characterizes 4MBQ-induced covalent modifications on β-lactoglobulin (β-LG) from bovine milk, (henceforth β-LQ) and the effect on protein digestibility. Significant thiol and amine loss was found in β-LQ compared to β-LG. Site-specific 4MBQ-induced modifications were identified on Cys, Lys, Arg, His and Trp in β-LQ. No significant differences between β-LG and β-LQ on in vitro digestibility were observed by assessment with SDS-PAGE, degree of hydrolysis and LC-MS/MS unmodified peptide intensities. Cys-4MC adduct (1.7 ± 0.1 µmol/g) was released from β-LQ after in vitro digestion. Thus, it is relevant to investigate how released Cys-4MC adducts are absorbed in vivo in future studies.

KW - 4-methylbenzoquinone

KW - Amino acid-polyphenol adducts

KW - Michael addition reaction

KW - Polyphenols

KW - Protein-polyphenol bonding

KW - Whey protein

UR - http://www.scopus.com/inward/record.url?scp=85135148565&partnerID=8YFLogxK

U2 - 10.1016/j.foodchem.2022.133775

DO - 10.1016/j.foodchem.2022.133775

M3 - Journal article

C2 - 35917780

AN - SCOPUS:85135148565

VL - 397

JO - Food Chemistry

JF - Food Chemistry

SN - 0308-8146

M1 - 133775

ER -

ID: 316395346