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. 2024 Jul 17;72(28):15933-15947.
doi: 10.1021/acs.jafc.4c02959. Epub 2024 Jul 5.

Influence of Hydroxycinnamic Acids on the Maillard Reaction of Arabinose and Galactose beyond Carbonyl-Trapping

Leon Valentin Bork  1 , Nicolas Proksch  1   2 , Tobias Stobernack  3 , Sascha Rohn  1 , Clemens Kanzler  1
Affiliations

Influence of Hydroxycinnamic Acids on the Maillard Reaction of Arabinose and Galactose beyond Carbonyl-Trapping

Leon Valentin Bork et al. J Agric Food Chem. .

Abstract

Hydroxycinnamic acids, known for their health benefits and widespread presence in plant-based food, undergo complex transformations during high-temperature processing. Recent studies revealed a high browning potential of hydroxycinnamic acids and reactive Maillard reaction intermediates, but the role of phenolic compounds in the early stage of these reactions is not unambiguously understood. Therefore, we investigated the influence of caffeic acid and ferulic acid on the nonenzymatic browning of arabinose, galactose, and/or alanine, focusing on the implications on the formation of relevant early-stage Maillard intermediates and phenol-deriving products. Contrary to previous assumptions, hydroxycinnamic acids were found to promote nonenzymatic browning instead of solely trapping reactive intermediates. This was reflected by an intense browning, which was attributed to the formation of heterogeneous phenol-containing Maillard products. Although, caffeic acid is more reactive than ferulic acid, the formation of reactive furan derivatives and of heterogeneous phenol-containing colorants was promoted in the presence of both hydroxycinnamic acids.

Keywords: 5-hydroxymethylfurfural; Maillard reaction; furfural; nonenzymatic browning; pyrrole-2-carbaldehyde; vinylcatechol; vinylguaiacol.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Color formation of individual, binary, and ternary reaction systems composed of different hydroxycinnamic acids (HCA), sugars, and alanine (Ala). Color index of (A) ferulic acid (FA) in combination with arabinose (Ara) and/or alanine, as well as of analogous mixtures of (B) caffeic acid (CA) heated at 220 °C for up to 10 min. Color formation of (C) arabinose, galactose (Gal), alanine, and the corresponding Maillard mixtures Ara/Ala as well as Gal/Ala, and of (D) the phenol-galactose mixtures. Statistical analyses were performed by two-way ANOVA and Tukey’s test (p < 0.05). Statistically equal values are designated by equal letters.
Figure 2
Figure 2
Heat-induced conversion of the hydroxycinnamic acids ferulic acid (FA) and caffeic acid (CA) during the incubation with arabinose (Ara) and/or alanine (Ala) at 220 °C for 10 min. Relative concentration of the reactants (A) FA, (B) CA, (C) Ara (FA systems), (D) Ara (CA systems), (E) Ala (FA systems), and (F) Ala (CA systems) in the corresponding reaction systems. Data obtained for individually treated Ara, galactose (Gal), Ala, the Maillard mixtures of Ara/Ala and Gal/Ala, as well as of the phenol/Gal mixtures are shown in the Supporting Information (Figure S-2).
Figure 3
Figure 3
Proposed decarboxylation mechanism of ferulic acid 1 in the presence of alanine 2 to vinylguaiacol 3 via its anion 3a.
Figure 4
Figure 4
Heat-induced formation of the heterocyclic Maillard intermediates furfural (FF), hydroxymethylfurfural (HMF), and pyrrole-2-carbaldehyde (PA). Formation of (A) FF, (B) HMF, and (C) PA after individual incubation of arabinose (Ara) and galactose (Gal) as well as in combination with alanine (Ala) and the hydroxycinnamic acids ferulic acid (FA) or caffeic acid (CA). Statistical analyses were performed by two-way ANOVA and Tukey’s test (p < 0.05). Statistically equal values are designated by equal letters.
Figure 5
Figure 5
Change in color and antioxidant activity after heating under roasting conditions for (A) ferulic acid (FA) and (B) caffeic acid (CA). Statistical analyses were performed by two-way ANOVA and Tukey’s test (p < 0.05). Statistically equal values are designated by equal letters. Data obtained for individually treated arabinose (Ara), galactose (Gal), alanine (Ala), the Maillard mixtures of Ara/Ala and Gal/Ala as well as of the HCA/Gal mixtures are shown in the Supporting Information (Figure S-6).
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