Quantitative Antioxidant Profiling Throughout Beer Brewing Followed by Discovery and Isolation of Precursors from Barley (Hordeum vulgare L.)

Stefan Spreng, Julia Wannenmacher, Martina Gastl, Corinna Dawid, Thomas Hofmann

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

The application of high-performance liquid chromatography-mass spectrometry (HPLC-MS/MS) revealed the origin and evolution of antioxidants during the brewing process of hopped and unhopped reference beer. As tachioside (3-methoxy-4-hydroxyphenyl-β-d-glucopyranoside), arbutin (4-hydroxyphenyl-β-d-glucopyranoside), and hordatines clearly increased during the fermentation step, the raw material barley was investigated as a source of the corresponding precursors. Therefore, 4-hydroxyphenyl-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranoside, 4-hydroxy-3-methoxyphenyl-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranoside, 4-hydroxy-3-methoxyphenyl-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranoside, and 4-hydroxy-2-methoxyphenyl-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranoside were isolated from barley for the first time, and identified using liquid chromatography-mass spectrometry (LC-MS) and one-dimensional/two-dimensional-nuclear magnetic resonance (1D/2D-NMR) experiments. Moreover, hordatine glucosides A, B, and C were isolated and identified from barley, and hordatine C glucoside was characterized for the first time. A fermentation model followed by HPLC-MS/MS analysis substantiated the release of tachioside from 4-hydroxy-3-methoxyphenyl-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranoside by Saccharomyces cerevisiae. Quantitation experiments monitoring the content in wheat, barley, and different barley malt types demonstrated a wide range of concentrations, providing a basis for further comprehensive investigations to optimize the antioxidant yield in beer to contribute to improved flavor stability.

Original languageEnglish
Pages (from-to)13885-13897
Number of pages13
JournalJournal of agricultural and food chemistry
Volume72
Issue number24
DOIs
StatePublished - 19 Jun 2024

Keywords

  • Hordeum vulgare
  • antioxidants
  • barley
  • beer
  • brewing process
  • hordatines
  • phenols
  • quantification
  • tachioside

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