Radical-Assisted Melanoidin Formation during Thermal Processing of Foods as well as under Physiological Conditions
Abstract
Color-generating reactions of protein-bound lysine with carbohydrates were studied under thermal as well as under physiological conditions to gain insights into the role of protein/carbohydrate reactions in the formation of food melanoidins as well as nonenzymatic browning products in vivo. EPR spectroscopy of orange-brown melanoidins, which were isolated from heated aqueous solutions of bovine serum albumin and glycolaldehyde, revealed the protein-bound 1,4-bis(5-amino-5-carboxy-1-pentyl)pyrazinium radical cation (CROSSPY) as a previously unknown type of cross-linking amino acid leading to protein dimerization. To verify their formation in foods, wheat bread crust and roasted cocoa as well as coffee beans, showing elevated nonenzymatic browning, were investigated by EPR spectroscopy. An intense radical was detected, which, by comparison with the radical formed upon reaction bovine serum albumin with glycolaldehyde, was identified as the protein-bound CROSSPY. The radical-assisted protein oligomerization as well as the browning of bovine serum albumin in the presence of glycolaldehyde occurred also rapidly under physiological conditions, thereby suggesting CROSSPY formation to be probably involved also in nonenzymatic glycation reactions in vivo.
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Melanoidin compounds are known to have antiradical properties and account for upwards of 25% of coffee's dry matter.
“Melanoidin compounds are known to have antiradical properties and account for upwards of 25% of coffee’s dry matter54,55, however, they have not been characterized in cold brew coffees.”
From Acidity and Antioxidant Activity of Cold Brew Coffee (2018) · cites this paper as [55]
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- Authors
- Hofmann, T., Bors, W., & Stettmaier, K.
- Affiliations
- Helmholtz Munich (DE)
- Corresponding author
- Hofmann, Thomas
- ORCID
- Hofmann, Thomas
- Venue
- Journal of Agricultural and Food Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1999-01-22
- Volume
- 47
- Issue
- 2
- Pages
- 391-396
- ISSN
- 0021-8561 (ISSN-L)
- 1520-5118
- OpenAlex
- W1971622981
- Cited by
- 87
- References
- 11
- Citations by year
- 2026: 1 · 2025: 1 · 2024: 2 · 2022: 1 · 2021: 7 · 2020: 2 · 2019: 1 · 2018: 2 · 2017: 4 · 2015: 5 · 2014: 7 · 2013: 8 · 2012: 8
- FWCI
- 2.35
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of Agricultural and Food Chemistry (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Clinical Biochemistry › Advanced Glycation End Products research
- Life Sciences › Agricultural and Biological Sciences › Food Science › Potato Plant Research
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Biophysics › Electron Spin Resonance Studies
- Keywords
- melanoidins, non-enzymatic browning, lysine, radical cations, bovine serum albumin, glycolaldehyde, protein dimerization, protein oligomerization, glycation, coffee beans, food coloration
- MeSH terms
- Chromatography, High Pressure Liquid, Color, Cooking, Electron Spin Resonance Spectroscopy, Food Analysis, Food Handling, Free Radicals, Polymers, Spectrophotometry, Ultraviolet, Mass Spectrometry, Sulfites
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