Stability of acrylamide in model systems and its reactivity with selected nucleophiles

Adams, An; Hamdani, Samira; Lancker, Fien Van; Méjri, Slah; Kimpe, Norbert De

doi:10.1016/j.foodres.2010.04.033

Cited by 53 publications

(47 citation statements)

References 22 publications

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“…Then, nucleophilic amino groups arising from the proteinaceous residue of the melanoidin skeleton are probably involved in the elimination of ACR during coffee roasting. This hypothesis is supported by earlier studies, in which amino acids with nucleophilic side chains considerably decrease levels of the free ACR, due to Michael-type addition reactions producing the corresponding 3-(alkylamino)-propionamide (Adams et al, 2010;Koutsidis et al, 2009;Zamora, Delgado, & Hidalgo, 2010). In addition, it is known that the addition of free amino acids other than the ACR precursor asparagine, such as glycine, lysine and cysteine, can reduce ACR concentrations in thermally treated foods (Brathen, Kita, Knutsen, & Wicklund, 2005;Rydberg et al, 2003).…”

Section: Discussionsupporting

confidence: 60%

“…Evaporation and/or polymerization are assumed to be the main causes of ACR decrease in the control as reported by others (i.e. Adams, Hamdani, Lancker, Méjri, & Kimpe, 2010;Claeys, de Vleeschouwer, & Hendrickx, 2005).…”

Section: Resultsmentioning

confidence: 76%

“…In addition, it is known that the addition of free amino acids other than the ACR precursor asparagine, such as glycine, lysine and cysteine, can reduce ACR concentrations in thermally treated foods (Brathen, Kita, Knutsen, & Wicklund, 2005;Rydberg et al, 2003). But the exact mechanisms of ACR degradation and adduct-formation in food products remain unknown (Adams et al, 2010).…”

Section: Discussionmentioning

confidence: 99%

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Reactivity of acrylamide with coffee melanoidins in model systems

Pastoriza

Rufián-Henares

Morales

2012

LWT - Food Science and Technology

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Coffee and its substitutes have been described as complex matrices for acrylamide (ACR) analysis due to both analytical interferences and ACR instability in the matrix. Melanoidins are multifunctional and biochemically active polymers which are formed in large extent during coffee roasting. Model systems composed of ACR (elimination studies) or glucose-asparagine (ACR formation/elimination studies) with/without melanoidins was heated at 180 _C. Washed sea sand and cellulose microcrystalline were used as matrix. Coffee melanoidins had a direct influence on the fate of ACR under heating, while the effect was not observed at room temperature. In addition, ACR decrease was also related to the reaction time and the initial amount of melanoidins in the media, where clearly a dose-response was observed. In contrast, pH (from 3.5 to 7.0) had no significant effect on ACR reactivity towards melanoidins. It is hypothesized that nucleophilic amino groups of amino acids from the proteinaceous backbone of melanoidins react via the Michael addition reaction with ACR, although the exact mechanism is unknown. Then, melanoidins could modulate the reaction pathways of ACR formation and elimination during coffee roasting and serve as acrylamide-mitigation substance.

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Section: Discussionsupporting

confidence: 60%

Section: Resultsmentioning

confidence: 76%

Section: Discussionmentioning

confidence: 99%

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Reactivity of acrylamide with coffee melanoidins in model systems

Pastoriza

Rufián-Henares

Morales

2012

LWT - Food Science and Technology

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“…Claeys et al (2005) kinetically analyzed the effect of amino acids on acrylamide formation/ elimination by heating a mixture of asparagine and glucose at temperatures between 140 and 200℃, and reported that the presence of cysteine or lysine significantly reduced acrylamide formation, whereas glutamine promoted the formation of acrylamide. There are also several studies reporting the reaction of acrylamide with amino acids such as glycine, lysine and cysteine at high temperatures (Adams et al, 2010;Liu et al, 2011;Zamora et al, 2010;Hidalgo et al, 2011). The addition of amino acids other than asparagine reduced acrylamide formation in homogenized potatoes heated at 180℃ for 20 min, probably due to the competitive consumption of acrylamide precursors and/or elimination of produced acrylamide by nucleophilic components in the amino acids (Rydberg et al, 2003).…”

Section: Introductionmentioning

confidence: 99%

“…However, the studies mentioned above dealt with reactions over 120℃, where acrylamide is preferentially produced. In contrast, there have been only a few studies of acrylamide formation at temperatures where acrylamide is not readily formed (Adams et al, 2010).…”

Section: Introductionmentioning

confidence: 99%

Elimination of Acrylamide by Moderate Heat Treatment below 120°C with Lysine and Cysteine

Kobayashi

Gomikawa

Yamazaki

et al. 2014

FSTR

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Acrylamide is a toxic compound generated in processed foods prepared at high temperatures. To explore means by which food processing can reduce the acrylamide content in foods, we studied the reaction of acrylamide with lysine and cysteine, which carry nucleophilic functional groups, at temperatures below the initiation of acrylamide generation. The amino acid-mediated reduction of acrylamide content followed first-order reaction kinetics in aqueous solution below 120℃. The profile of acrylamide decrease correlated well with the formation of a 1:1 adduct of acrylamide with the respective amino acid, indicating that these amino acids reacted directly with acrylamide.The reactivity of acrylamide toward both amino acids was pH-dependent. In particular, the reactivity of cysteine toward acrylamide was remarkably enhanced by an increase in pH. These findings suggested the possibility of reducing acrylamide levels during food processing by treating foods with the appropriate amino acid(s) at moderate temperatures below 120℃.

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