Formation of genotoxic dicarbonyl compounds in dietary oils upon oxidation

Fujioka, Kazutoshi; Shibamoto, Takayuki

doi:10.1007/s11745-004-1254-y

Cited by 70 publications

(56 citation statements)

References 38 publications

(44 reference statements)

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“…For example, a high level of glyoxal formation (12.8 ppm) was observed when salmon oil was heated at 608C for 7 days (Fujioka and Shibamoto, 2004). Methylglyoxal found in brewed coffee was found to be mutagenic by the Ames test (Kasai et al, 1982).…”

Section: Discussionmentioning

confidence: 99%

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Determination of toxic carbonyl compounds in cigarette smoke

2006

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Toxic carbonyl compounds, including formaldehyde, malonaldehyde, and glyoxal, formed in mainstream cigarette smoke were quantified by derivatization-solid phase extraction-gas chromatography methods. Cigarette smoke from 14 commercial brands and one reference (2R1F) was drawn into a separatory funnel containing aqueous phosphate-buffered saline. Reactive carbonyl compounds trapped in the buffer solution were derivatized into stable nitrogen containing compounds (pyrazoles for -dicarbonyl and , -unsaturated aldehyde; quinoxalines for -dicarbonyls; and thiazolidines for alkanals). After derivatives were recovered using C 18 solid phase extraction cartridges, they were analyzed quantitatively by a gas chromatograph with a nitrogen phosphorus detector. The total carbonyl compounds recovered from regular size cigarettes ranged from 1.92 mg/cigarette À1 to 3.14 mg/cigarette À1 . The total carbonyl compounds recovered from a reference cigarette and a king size cigarette were 3.23 mg/cigarette À1 and 3.39 mg/cigarette À1 , respectively. The general decreasing order of the carbonyl compounds yielded was acetaldehyde (1110-2101 g/cigarette À1 ) > diacetyl (301-433 g/cigarette À1 ), acrolein (238-468 g/cigarette À1 ) > formaldehyde (87.0-243 g/cigarette À1 ), propanal (87.0-176 g/cigarette À1 ) > malonaldehyde (18.9-36.0 g/cigarette À1 ), methylglyoxal (13.4-59.6 g/cigarette À1 ) > glyoxal (1.93-6.98 g/cigarette À1 ).

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Section: Discussionmentioning

confidence: 99%

“…Methylglyoxal found in brewed coffee was found to be mutagenic by the Ames test (Kasai et al, 1982). Methylglyoxal was also formed in heated dietary oils such as cod liver oil (2.03 ppm) and tuna oil (2.89 ppm) (Fujioka and Shibamoto, 2004).…”

Section: Discussionmentioning

confidence: 99%

Determination of toxic carbonyl compounds in cigarette smoke

2006

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“…Dehydration of hexose sugars mainly leads to 3-deoxyglucosone formation and, to a smaller extent, to 1-deoxyglucosone, while major oxidation product of hexoses is glucosone [9,10]. Glyoxal, methylglyoxal and diacetyl (dimethylglyoxal) are formed from fragmentation of reactive intermediates during Maillard reaction and also from degradation of lipid oxidation products [11][12][13][14]. Progresses of Maillard reaction, caramelization and thermal oxidation highly depend on time-temperature profile of the thermal process.…”

Section: Introductionmentioning

confidence: 99%

Formation of α-dicarbonyl compounds in cookies made from wheat, hull-less barley and colored corn and its relation with phenolic compounds, free amino acids and sugars

Kocadağlı

Žilić

Taş

et al. 2015

Eur Food Res Technol

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“…The methods, validated for specific samples, were used for determination of MG in different wines [37,53,54], beer [54], lipids [42,55], dairy products [56,57], honey [58], and many others.…”

Section: Quantification Of Methylglyoxal In Food Samples and Cigarettmentioning

confidence: 99%

“…Depending on oil origin (tuna, salmon, cod liver, soybean, olive, and corn oils) under accelerated storage conditions (608C for 3 and 7 days) or cooking (2008C for 1 h), a broad range in MG levels were obtained. In such a manner, the amount of MG formed in fish oils heated at 608C for 7 days ranged from 2.03 € 0.13 (cod liver oil) to 2.89 € 0.11 mg/kg (tuna oil), whereas among vegetable oils under these conditions, only olive oil yielded MG (0.61 € 0.03 mg/kg) [55]. Photodegradation of lipids and related compounds also yielded MG as a degradation product [42].…”

Section: Generalmentioning

confidence: 99%

Methylglyoxal in food and living organisms

Nemet

Varga-Defterdarović

Turk³

2006

Molecular Nutrition Food Res

142

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Methylglyoxal (MG) is a highly reactive alpha-oxoaldehyde formed endogenously in numerous enzymatic and nonenzymatic reactions. It modifies arginine and lysine residues in proteins forming advanced glycation end-products such as N(delta)-(5-methyl-4-imidazolon-2-yl)-L-ornithine (MG-H1), 2-amino-5-(2-amino-5-hydro-5-methyl-4-imidazolon-1-yl)pentanoic acid (MG-H2), 2-amino-5-(2-amino-4-hydro-4-methyl-5-imidazolon-1-yl)pentanoic acid (MG-H3), argpyrimidine, N(delta)-(4-carboxy-4,6-dimethyl-5,6-dihydroxy-1,4,5,6-tetrahydropyrimidine-2-yl)-L-ornithine (THP), N(epsilon)-(1-carboxyethyl)lysine (CEL), MG-derived lysine dimer (MOLD), and 2-ammonio-6-({2-[4-ammonio-5-oxido-5-oxopently)amino]-4-methyl-4,5-dihydro-1H-imidazol-5-ylidene}amino)hexanoate (MODIC), which have been identified in vivo and are associated with complications of diabetes and some neurodegenerative diseases. In foodstuffs and beverages, MG is formed during processing, cooking, and prolonged storage. Fasting and metabolic disorders and/or defects in MG detoxification processes cause accumulation of this reactive dicarbonyl in vivo. In addition, the intake of low doses of MG over a prolonged period of time can cause degenerative changes in different tissues, and can also exert anticancer activity. MG in biological samples can be quantified by HPLC or GC methods with preliminary derivatization into more stable chromophores and/or fluorophores, or derivatives suitable for determination by MS by use of diamino derivatives of benzene and naphthalene, 6-hydroxy-2,4,5-triaminopyrimidine, cysteamine, and o-(2,3,4,5,6-pentafluorobenzyl) hydroxylamine. The methods include three basic steps: deproteinization, incubation with derivatization agent, and chromatographic analysis with or without preliminary extraction of the formed products.

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Formation of genotoxic dicarbonyl compounds in dietary oils upon oxidation

Cited by 70 publications

References 38 publications

Determination of toxic carbonyl compounds in cigarette smoke

Determination of toxic carbonyl compounds in cigarette smoke

Formation of α-dicarbonyl compounds in cookies made from wheat, hull-less barley and colored corn and its relation with phenolic compounds, free amino acids and sugars

Methylglyoxal in food and living organisms

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