Metabolization of Free Oxidized Aromatic Amino Acids by Saccharomyces cerevisiae

Research output: Contribution to journalResearch articleContributedpeer-review

Contributors

  • Kim Ina Behringer - , Technical University of Braunschweig (Author)
  • Julia Kapeluch - , Technical University of Braunschweig (Author)
  • Annik Fischer - , Technical University of Braunschweig (Author)
  • Michael Hellwig - , Chair of Special Food Chemistry, Technical University of Braunschweig, TUD Dresden University of Technology (Author)

Abstract

The aromatic amino acids tryptophan, phenylalanine, and tyrosine are targets for oxidation during food processing. We investigated whether S. cerevisiae can use nonproteinogenic aromatic amino acids as substrates for degradation via the Ehrlich pathway. The metabolic fate of seven amino acids (p-, o-, m-tyrosine, 3,4-dihydroxyphenylalanine (DOPA), 3-nitrotyrosine, 3-chlorotyrosine, and dityrosine) in the presence of S. cerevisiae was assessed. All investigated amino acids except dityrosine were metabolized by yeast. The amino acids 3-nitrotyrosine and o-tyrosine were removed from the medium as fast as p-tyrosine, and m-tyrosine, 3-chlorotyrosine, and DOPA more slowly. In summary, 11 metabolites were identified by high-performance liquid chromatography-mass spectrometry (HPLC-MS/MS). DOPA, 3-nitrotyrosine, and p-tyrosine were metabolized predominantly to the Ehrlich alcohols, whereas o-tyrosine and m-tyrosine were metabolized predominantly to α-hydroxy acids. Our results indicate that nonproteinogenic aromatic amino acids can be taken up and transaminated by S. cerevisiae quite effectively but that decarboxylation and reduction to Ehrlich alcohols as the final metabolites is hampered by hydroxyl groups in the o- or m-positions of the phenyl ring. The data on amino acid metabolism were substantiated by the analysis of five commercial beer samples, which revealed the presence of hydroxytyrosol (ca. 0.01-0.1 mg/L) in beer for the first time.

Details

Original languageEnglish
Pages (from-to)5766-5776
Number of pages11
JournalJournal of agricultural and food chemistry
Volume72
Issue number11
Publication statusPublished - 20 Mar 2024
Peer-reviewedYes

External IDs

PubMed 38447044
ORCID /0000-0001-8528-6893/work/173516449

Keywords

Keywords

  • 3-chlorotyrosine, 3-nitrotyrosine, beer, dityrosine, fermentation, m-tyrosine, metabolism, o-tyrosine, protein oxidation, tyrosine, yeast