Strecker Degradation of Phenylalanine Initiated by 2,4-Decadienal or Methyl 13-Oxooctadeca-9,11-dienoate in Model Systems

Zamora, Rosario; Gallardo, Emerenciana; Hidalgo, Francisco J.

doi:10.1021/jf062838x

Cited by 59 publications

(72 citation statements)

References 21 publications

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“…Researches showed that some secondary lipid oxidation products can convert amino acids into the corresponding vinylogous derivatives Zamora et al 2007), and some lipid oxidation products can degrade asparagine to acrylamide ). They proposed α,β,γ,δ-diunsaturated carbonyl compounds as the most reactive, followed by hydroperoxides, likely because of their thermal decomposition upon heating.…”

Section: Lipid Oxidationmentioning

confidence: 99%

Acrylamide in Baking Products: A Review Article

Keramat

Le‐Bail

Prost

et al. 2010

Food Bioprocess Technol

140

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Acrylamide or 2-propenamide is a chemical compound, with chemical formula CH 2 =CH-CO-NH 2 , that can be produced at high levels in high-carbohydrate heattreated foods. The risks of acrylamide to health and its toxic properties (neurotoxicity, genotoxicity, carcinogenicity and reproductive toxicity) were demonstrated by the Scientific Committee on Toxicity, Ecotoxicity and the Environment in 2001. Potato and bakery products account for around 50% and 20% of human exposure to acrylamide, respectively. Factors affecting acrylamide formation and degradation in foods are acrylamide precursors such as free amino acids (mainly asparagine), reducing sugars and processing conditions (i.e. baking time and temperature, moisture content and matrix of product). The aim of this review was to present some results from recent investigations of the effects of different factors affecting acrylamide formation in bakery products. Finally, recommendations are proposed as guidelines for baking manufacturers to reduce the level of acrylamide in their products.

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Section: Lipid Oxidationmentioning

confidence: 99%

Acrylamide in Baking Products: A Review Article

Keramat

Le‐Bail

Prost

et al. 2010

Food Bioprocess Technol

140

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“…This is likely a consequence of the reactivity of these compounds, which can react with amino compounds in several other ways, in addition to contribute to its deamination. Thus, the formation of Strecker aldehydes and diverse heterocyclic compounds, among other reactions, has been described by carbonyl-amine reactions in amino acids/ alkadienals reactions mixtures [19][20][21]. All these results suggest the existence of diverse competitive pathways by which 3-aminopropionamide and 3-(alkylamino)propionamides are converted into acrylamide.…”

Section: Discussionmentioning

confidence: 91%

Conversion of 3‐aminopropionamide and 3‐alkylaminopropionamides into acrylamide in model systems

Zamora

Delgado

Hidalgo

2009

Molecular Nutrition Food Res

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Carbonyl compounds have been shown to play a major role in the conversion of asparagine into acrylamide. However, it is unclear at this point if its role is only restricted to the decarboxylation of the amino acid or if carbonyl compounds also play a role in the deamination reaction of the decarboxylated intermediates 3-aminopropionamide and 3-(alkylamino)propionamides. This study describes the deamination reaction of 3-aminopropionamide and 3-(alkylamino)propionamides (benzyl, phenylethyl, butyl, and octyl) in model systems and in the presence, or not, of different carbonyl compounds (alkadienals, alkenals, and alkanals). All these reactions were mainly produced at almost neutral or basic pH values. In addition, the reaction yields and the activation energies not only depended on the type of aminopropionamide involved but also on the water activity (a(w)) and in the presence, or not, of carbonyl compounds. However, there was not a clear correlation among the activation energies calculated for the different deamination reactions and the yields of acrylamide obtained; therefore, suggesting the existence of diverse pathways by which 3-aminopropionamide and 3-(alkylamino)propionamides are converted into acrylamide. In addition, these reactions are also competing with other carbonyl-amine reactions when carbonyl compounds are present. All these results suggest that the type of the intermediate aminopropionamide involved is going to play a major role in both the amount of acrylamide produced and the conditions required for its formation. On the other hand, the role of carbonyl compounds in the acrylamide produced, but not in the activation energy of the reactions implicated, seems to be more limited than either the type of amine or the a(w). A detailed analysis of the type of the intermediate aminopropionamide formed in foods may help to define strategies for mitigating the formation of this food toxicant.

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“…37,39 In fact, the ability of aldehydes and ketones for 35 degrading amino acids was similar in most experiments and differences found might be more related to differences in solubility among the different lipid oxidation products than differences in reactivity. 40 In addition, this reaction has also been described for lipid hydroperoxides, 41 although a free radical 40 mechanism is likely taking place in this degradation in addition to the contribution of the reactive carbonyls produced by Scheme 6 Strecker degradation of phenylalanine produced by glyoxal Scheme 7 Strecker degradation of phenylalanine produced by 4,5-epoxy-2-alkenals hydroperoxide decomposition.…”

Section: Other Degradative Pathways That Produce Strecker Aldehydes Amentioning

confidence: 87%

“…15 The Strecker degradation of amino acids produced by secondary lipid oxidation products was firstly described in 2004 for the formation of phenylacetaldehyde by phenylalanine degradation in the presence of epoxyalkenals, 26 and later extended to other lipid-derived reactive carbonyls. [36][37][38] aldehyde formation by lipid oxidation products is believed to be produced analogously to amino acid degradation by α-dicarbonyl compounds. Scheme 7 shows the reaction pathway for the degradation of phenylalanine in the presence of 4,5-epoxyalkenals.…”

Section: Other Degradative Pathways That Produce Strecker Aldehydes Amentioning

confidence: 99%

2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) formation and fate: an example of the coordinate contribution of lipid oxidation and Maillard reaction to the production and elimination of processing-related food toxicants

Zamora

Hidalgo

2015

RSC Adv.

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2-Amino-1-methyl-6-phenylimidazo [4,5-b]pyridine (PhIP) is produced by reaction of phenylacetaldehyde, the Strecker aldehyde of phenylalanine, with creati(ni)ne in the presence of formaldehyde and ammonia, which are formed in situ. Traditionally, the carbonyls compounds required 10 for the formation of PhIP ring were considered to be produced as a consequence of Maillard reaction between phenylalanine and carbohydrates. This review collects all recent evidences suggesting that lipids can also contribute to produce the Strecker degradation of phenylalanine and the formation of formaldehyde analogously to carbohydrates. Furthermore, lipid-derived reactive carbonyls not only contribute to PhIP formation but they can also be involved in PhIP fate observed in the presence of 15 oxidized oils. This role has not been yet investigated for carbohydrate-derived reactive carbonyls but it might be hypothesised to take place because of the decrease of PhIP observed when excess of monosacharides is employed to study PhIP formation. All these results suggest that carbohydrates and lipids can contribute simultaneously to PhIP formation and fate. This is another example of the simultaneous contribution of both lipids and carbohydrates to the carbonyl chemistry that takes place in 20 foods upon processing and/or storage. Furthermore, many of these conclusions can also be extended to the formation of other aminoimidazoazarenes with structure of imidazopyridine.

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Strecker Degradation of Phenylalanine Initiated by 2,4-Decadienal or Methyl 13-Oxooctadeca-9,11-dienoate in Model Systems

Cited by 59 publications

References 21 publications

Acrylamide in Baking Products: A Review Article

Acrylamide in Baking Products: A Review Article

Conversion of 3‐aminopropionamide and 3‐alkylaminopropionamides into acrylamide in model systems

2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) formation and fate: an example of the coordinate contribution of lipid oxidation and Maillard reaction to the production and elimination of processing-related food toxicants

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