Epoxyalkenal-trapping ability of phenolic compounds

Zamora, Rosario; Aguilar, Isabel; Hidalgo, Francisco J.

doi:10.1016/j.foodchem.2017.05.129

Cited by 30 publications

(16 citation statements)

References 21 publications

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“…Thus, adducts were produced to a small extent at neutral pH, but their yields increased rapidly to higher pH values. This behavior is likely related to the increase of nucleophilicity of phenolic carbons, also observed in the reaction of phenolics with other aldehydes (Zamora et al, 2017). This high nucleophilicity is needed for the first step of the reaction pathway proposed in Fig.…”

Section: Discussionmentioning

confidence: 71%

2,4-Alkadienal trapping by phenolics

Hidalgo

Zamora

2018

Food Chemistry

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Phenolics can trap lipid-derived reactive carbonyls as a protective function that diminishes the broadcasting of the lipid oxidative damage to food macromolecules. In an attempt to clarify the trapping of 2,4-alkadienals by phenolics, this study analyzes the reactions of 2,4-hexadienal, 2,4-heptadienal, and 2,4-decadienal with 2-methylresorcinol. These reactions produced (E)-4-(alk-1-en-1-yl)-8-methyl-2,7-bis(prop-1-en-2-yloxy)chromanes, which were isolated and characterized by 1D and 2D NMR and MS. Carbonyl-phenol adduct formation was favored at pH > 7 and moderate temperatures (25-80 °C). Adducts were quantified and shown to be produced as a mixture of diastereomers. Diastereomers 2R,4S plus 2S,4R were formed to a higher extent than diastereomers 2R,4R plus 2S,4S under the different conditions assayed, although activation energies (E) for the formation of all of them was mostly the same (∼62 kJ·mol). These results show that phenolics can trap 2,4-alkadienals and provide the basis for the later detection of the formed adducts in food pro[ducts.

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Section: Discussionmentioning

confidence: 71%

2,4-Alkadienal trapping by phenolics

Hidalgo

Zamora

2018

Food Chemistry

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“…In nature, polyphenols occur as monomers, oligomers, and polymers (proanthocyanidins, condensed tannins). There is also evidence indicating that, during the storage and aging of food products and beverages with a high content of flavonoids, the latter react with carbonyl compounds such as acetaldehyde, methylglyoxal, glyoxylic acid, and furfurol, which results in the formation of monomeric, oligomeric, and polymeric adducts [ 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 ].…”

Section: Introductionmentioning

confidence: 99%

Comparison of Antioxidant Properties of a Conjugate of Taxifolin with Glyoxylic Acid and Selected Flavonoids

2021

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It is known that flavonoids can react with toxic carbonyl compounds in the process of the storage, aging, and digestion of flavonoid-rich foods and beverages. However, the effect of these reactions on the antioxidant properties of the polyphenolic fraction and the properties of the resulting products remain poorly studied. The aim of the present work was to study the antioxidant activity of quercetin, taxifolin, catechin, eriodictyol, hesperetin, naringenin and a product of the condensation of taxifolin with glyoxylic acid, as well as to reveal the structure–activity relationship of these polyphenols. It was found that flavonoids containing the catechol moiety exhibited higher antioxidant activity than hesperetin and naringenin. The product showed the highest hydrogen peroxide scavenging activity, a lower metal-reducing and a higher iron-binding ability than catechol-containing flavonoids, and a lipid peroxidation inhibitory activity comparable with that of taxifolin. Thus, the condensation of flavonoids with toxic carbonyl compounds might lead to the formation of products exhibiting high antioxidant activity. Meanwhile, the conditions under which parent flavonoids and their products exhibit the maximal antioxidant activity may differ. The data suggest that the antioxidant profile of the polyphenolic fraction and bioavailability of polyphenols, carbonyl compounds, and metal ions may change when these reactions occur.

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“…26 As an exception, in 4,5-epoxy-2alkenals, the reaction is initiated by the attack of the hydroxyl group of the phenolic to the epoxide ring of the lipid carbonyl because of the high reactivity of this three membered ring. 27 4-Hydroxy-2-alkenals are basically ,-unsaturated carbonyl compounds. Therefore, its behavior, at least at the initial steps, should be similar to other unsaturated carbonyl compounds.…”

Section: Discussionmentioning

confidence: 99%

“…18 In addition, formation of these carbonyl-phenol adducts has been related to the protective function of some phenolics on the formation of heterocyclic aromatic amines and biogenic amines by carbonylamine reactions, 19,20 and the beneficial properties of polyphenolic-rich foods such as tea or coffee. 21 Although carbonyl-phenol reactions with different lipid-derived reactive carbonyls have been described, [22][23][24][25][26][27] the ability of phenolic compounds to trap and produce carbonyl-phenol adducts with 4-hydroxyalkenals has not been described. To the best of our knowledge, although several studies have shown that 4-hydroxy-2-nonenal (HNE) seems to be effectively trapped by phenolics, 28,29 neither the produced reaction has been described in detail nor the structure(s) of the formed adduct(s) has been unequivocally characterized.…”

Section: Introductionmentioning

confidence: 99%

Characterization of Carbonyl–Phenol Adducts Produced by Food Phenolic Trapping of 4-Hydroxy-2-hexenal and 4-Hydroxy-2-nonenal

Hidalgo

Zamora

2019

J. Agric. Food Chem.

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4-Hydroxy-2-alkenals disappear in the presence of food phenolics (i.e. cathechin or quercetin) and the corresponding carbonyl-phenol adducts are produced. In an attempt to identify structure(s) of formed adducts, the reactions between model phenolics (resorcinol, 2-methylresorcinol, orcinol, and 2,5-dimethylresorcinol) and hydroxyalkenals (4-hydroxy-2-hexenal and 4-hydroxy-2-nonenal) were studied and the produced adducts were isolated by column chromatography and unambiguously characterized by 1D and 2D NMR and MS as dihydrobenzofuranols (1), chromane-2,7diols (2), and 2H-chromen-7-ols (3). These compounds were mainly produced at slightly basic pH values and moderate temperatures. Their activation energies (Ea) of formation were 25 kJ•mol -1 for adducts 1, 32 kJ•mol -1 for adducts 2, and 38 kJ•mol -1 for adducts 3. A reaction pathway that explains their formation is proposed. All these results confirm that, analogously to other lipid-derived carbonyl compounds, phenolics can trap 4-hydroxy-2-alkenals in an efficient way. Obtained results provide the basis for the potential detection of carbonyl-phenol adducts derived from hydroxyalkenals in food products.

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Epoxyalkenal-trapping ability of phenolic compounds

Cited by 30 publications

References 21 publications

2,4-Alkadienal trapping by phenolics

2,4-Alkadienal trapping by phenolics

Comparison of Antioxidant Properties of a Conjugate of Taxifolin with Glyoxylic Acid and Selected Flavonoids

Characterization of Carbonyl–Phenol Adducts Produced by Food Phenolic Trapping of 4-Hydroxy-2-hexenal and 4-Hydroxy-2-nonenal

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