Identification of hydroxycinnamic acid - maillard reaction products in low-moisture baking model systems

Jiang Deshou, Chiaro Christopher, Maddali Pranav, K. Sandeep, Devin G Peterson

Research output: Contribution to journalArticlepeer-review

36 Scopus citations

Abstract

The chemistry and fate of hydroxycinnamic acids (ferulic, p-coumeric, caffeic, sinapic, and cinnamic acid) in a glucose/glycine simulated baking model (10% moisture at 200 °C for 15 min) were investigated. Liquid chromatography-mass spectrometry analysis of glucose/glycine and glucose/glycine/hydroxycinnamic acid model systems confirmed the phenolics reacted with Maillard intermediates; two main reaction product adducts were reported. On the basis of isotopomeric analysis, LC-MS, and NMR spectroscopy, structures of two ferulic acid-Maillard reaction products were identified as 6-(4-hydroxy-3-methoxyphenyl)-5-(hydroxymethyl)-8-oxabicyclo[3.2.1] oct-3-en-2-one (adduct I) and 2-(6-(furan-2-yl)-7-(4-hydroxy-3-methoxyphenyl)-1- methyl-3-oxo-2,5diazabicyclo[2.2.2]oct-5-en-2-yl)acetic acid (adduct II). In addition, a pyrazinone-type Maillard product, 2-(5-(furan-2-yl)-6-methyl-2- oxopyrazin-1(2H)-yl) acetic acid (IIa), was identified as an intermediate for reaction product adduct II, whereas 3-deoxy-2-hexosulose was identified as an Intermediate of adduct I. Both adducts I and II were suggested to be generated by pericyclic reaction mechanisms. Quantitative gas chromatography (GC) analysis and liquid chromatography (LC) also indicated that the addition of ferulic acid to a glucose/glycine model significantly reduced the generation of select Maillard-type aroma compounds, such as furiurals, methylpyrazines, 2-acetylfuran, 2-acetylpyridine, 2-acetylpyrrole, and cyclotene as well as inhibited color development in these Maillard models. In addition, adducts I and II suppressed the bacterial lipopolysaccharide (LPS)-mediated expression of two prototypical pro-inflammatory genes, inducible nitric oxide synthase (iNOS) and cyclooxygenase (COX)-2, in an in vitro murine macrophage model; ferulic acid reported negligible activity.

Original languageEnglish (US)
Pages (from-to)9932-9943
Number of pages12
JournalJournal of agricultural and food chemistry
Volume57
Issue number21
DOIs
StatePublished - Nov 11 2009

Keywords

  • Hydroxycinnamic acids
  • Inos and cox-2 suppression
  • Maillard reaction
  • Maillard-phenolic reaction product
  • Pericyclic reaction

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