Formation of β-phenylethylamine as a consequence of lipid oxidation

Zamora, Rosario; Delgado, Rosa M.; Hidalgo, Francisco J.

doi:10.1016/j.foodres.2011.12.029

Cited by 32 publications

(32 citation statements)

References 24 publications

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“…In particular, PhIP formation is considered a several step process in which sugars produce the conversion of phenylalanine into phenylacetaldehyde, and the later reaction between phenylacetaldehyde and creat(in)ine is the responsible for the formation of PhIP (Murkovic, 2004). Although, phenylacetaldehyde can be produced by thermal decomposition of phenylalanine, carbonyl compounds facilitate this reaction (Estevez, Ventanas, & Heinonen, 2011;Zamora, Delgado, & Hidalgo, 2011, 2012. Therefore, most carbonyl compounds should potentially contribute to PhIP formation in foods, although reaction yields will depend on the presence of additional functional groups in the carbonyl compound.…”

Section: Discussionmentioning

confidence: 99%

Effect of lipid oxidation products on the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in model systems

2012

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Section: Discussionmentioning

confidence: 99%

Effect of lipid oxidation products on the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in model systems

2012

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“…Several factors could affect the final accumulation of BAs. In particular, some authors have reported that Strecker degradation is responsible for the formation of BAs during the thermal decarboxylation of amino acids in the presence of α-dicarbonyl compounds formed during the Maillard reaction [12,36] or lipid peroxidation [37].…”

Section: Effect Of Roasting On the Bas Contentmentioning

confidence: 99%

Effect of Fermentation, Drying and Roasting on Biogenic Amines and Other Biocompounds in Colombian Criollo Cocoa Beans and Shells

Delgado‐Ospina

Mattia

Paparella

et al. 2020

Foods

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The composition of microbiota and the content and pattern of bioactive compounds (biogenic amines, polyphenols, anthocyanins and flavanols), as well as pH, color, antioxidant and reducing properties were investigated in fermented Criollo cocoa beans and shells. The analyses were conducted after fermentation and drying (T1) and after two thermal roasting processes (T2, 120 • C for 22 min; T3, 135 • C for 15 min). The fermentation and drying practices affected the microbiota of beans and shells, explaining the great variability of biogenic amines (BAs) content. Enterobacteriaceae were counted in a few samples with average values of 10 3 colony forming units per gram (CFU g −1 ), mainly in the shell, while Lactobacillus spp. was observed in almost all the samples, with the highest count in the shell with average values of 10 4 CFU g −1 . After T1, the total BAs content was found to be in a range of 4.9÷127.1 mg kg −1 DFW ; what was remarkable was the presence of cadaverine and histamine, which have not been reported previously in fermented cocoa beans. The total BAs content increased 60% after thermal treatment T2, and of 21% after processing at T3, with a strong correlation (p < 0.05) for histamine (ß = 0.75) and weakly correlated for spermidine (ß = 0.58), spermine (ß = 0.50), cadaverine (ß = 0.47) and serotonine (ß = 0.40). The roasting treatment of T3 caused serotonin degradation (average decrease of 93%) with respect to unroasted samples. However, BAs were detected in a non-alarming concentration (e.g., histamine: n.d ÷ 59.8 mg kg −1 DFW ; tyramine: n.d. ÷ 26.5 mg kg −1 DFW ). Change in BAs level was evaluated by principal component analysis. PC1 and PC2 explained 84.9% and 4.5% of data variance, respectively. Antioxidant and reducing properties, polyphenol content and BAs negatively influenced PC1 with both polyphenols and BA increasing during roasting, whereas PC1 was positively influenced by anthocyanins, catechin and epicatechin.

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“…Moreover, it has been reported that in cocoa the oxidative decarboxylation of the corresponding amino acid can be also obtained during thermal processes, indicating that roasting conditions such as temperature and relative humidity of air greatly affect the levels of BAs (Oracz & Nebesny 2014). To this regard, some authors have reported that the Strecker degradation is responsible for the formation of BAs in the way of thermal decarboxylation of amino acids in the presence of α-dicarbonyl compounds formed during the Maillard reaction or lipid peroxidation products (Granvogl et al 2006;Granvogl & Schieberle 2007;Zamora et al 2012). These results suggested a new 'thermogenic' formation pathway of BAs in cocoa beans.…”

Section: Introductionmentioning

confidence: 99%

Determination of biogenic amine profiles in conventional and organic cocoa-based products

Restuccia

Spizzirri

Puoci

et al. 2015

Food Additives & Contaminants: Part A

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Cocoa contains many compounds such as biogenic amines (BAs), known to influence consumer health. Spermidine, spermidine, putrescine, histamine, tyramine, β-phenylethylamine, cadaverine and serotonine have been found in several cocoa-based products using HPLC with UV detection after derivatisation with dansyl-chloride. Once optimised in terms of linearity, percentage recovery, LOD, LOQ and repeatability, this method was applied to real samples. Total concentrations of BAs ranged from 5.7 to 79.0 µg g(-)(1) with wide variations depending on the type of sample. BAs present in all samples were in decreasing order: histamine (1.9-38.1 µg g(-)(1)) and tyramine (1.7-31.7 µg g(-)(1)), while putrescine (0.9-32.7 µg g(-)(1)), spermidine (1.0-9.7 µg g(-)(1)) and spermidine (0.6-9.3 µg g(-)(1)) were present in most of the samples. Cadaverine, serotonine and β-phenylethylamine were present in a few samples at much lower concentrations. Organic samples always contained much lower levels of BAs than their conventional counterparts and, generally speaking, the highest amounts of BAs were found in the most processed products.

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Formation of β-phenylethylamine as a consequence of lipid oxidation

Cited by 32 publications

References 24 publications

Effect of lipid oxidation products on the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in model systems

Effect of lipid oxidation products on the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in model systems

Effect of Fermentation, Drying and Roasting on Biogenic Amines and Other Biocompounds in Colombian Criollo Cocoa Beans and Shells

Determination of biogenic amine profiles in conventional and organic cocoa-based products

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