Alpha-Dicarbonyl Compounds

Zheng, Jie; Ou, Juanying; Ou, Shiyi

doi:10.1007/978-981-13-8118-8_2

Cited by 12 publications

(8 citation statements)

References 70 publications

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“…First, Schiff base hydrolyze to Amadori rearrangement products in aqueous systems. Amadori compounds transform to dicarbonyl compounds, 43 which further react with Asn to form Strecker aldehyde 41 . Strecker aldehyde can be reduced to Strecker alcohol, which finally dehydrates to form AA 3 .…”

Section: Resultsmentioning

confidence: 99%

Acceleration effect of galacturonic acid on acrylamide generation: evidence in model reaction systems

Wang

Sun

et al. 2022

J Sci Food Agric

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BACKGROUND Acrylamide (AA) is a potential carcinogen formed in food rich in carbohydrate during heating. Recently, AA has been found in several fruit products, such as prune juice, sugarcane molasses and canned black olives. This study focused on the role of galacturonic acid (GalA), the main acid hydrolysis product of fruit pectin, in AA formation in three model systems – asparagine (Asn)/glucose (Glc), Asn/GalA, and Asn/Glc/GalA – during heating under different pH values (pH 3.8–7.8), Glc concentration (0–0.1 mol L−1), molar ratio of substrates (Asn/Glc = 1:1, 0.025–0.5 mol L−1) and temperature (120–180 °C) for 30 min, respectively. RESULTS The results suggested that the addition of 0.1 mol L−1 GalA strongly accelerated AA formation in a manner dependent on pH value and temperature (P < 0.05). AA concentration under different Glc concentration and molar ratio of substrates suggested that GalA was more reactive than Glc when reacted with Asn. Furthermore, the Amadori rearrangement product/Schiff base/oxazolidine‐5‐one were identified as the intermediates formed in the Asn/GalA model system using ultra‐performance liquid chromatography–quadrupole‐time‐of‐flight–mass spectrometry. CONCLUSION The results suggested that Maillard reaction between Asn and GalA might contribute to AA formation. This study is significant in elucidating the contribution of interaction between components for AA formation in fruit products. © 2022 Society of Chemical Industry.

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Section: Resultsmentioning

confidence: 99%

Acceleration effect of galacturonic acid on acrylamide generation: evidence in model reaction systems

Wang

Sun

et al. 2022

J Sci Food Agric

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“…Dicarbonyl compounds are formed in thermally processed foods from the oxidation and degradation of sugars, the Maillard reaction, degradation of lipids, and degradation of vitamin C [ 86 ]. Dicarbonyl compounds found in honey samples of different floral origins include glyoxal, methylglyoxal, glucosone, 3-deoxyglucosone, 2,3-butanedione, 3-deoxypentulose, 1,4-dideoxyhexulose, and 3,4-dideoxyglucoson-3-ene (3,4-DGE) [ 87 , 88 ].…”

Section: Non-enzymatic Reactions In Honeymentioning

confidence: 99%

Biochemical Reactions and Their Biological Contributions in Honey

et al. 2022

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Honey is known for its content of biomolecules, such as enzymes. The enzymes of honey originate from bees, plant nectars, secretions or excretions of plant-sucking insects, or from microorganisms such as yeasts. Honey can be characterized by enzyme-catalyzed and non-enzymatic reactions. Notable examples of enzyme-catalyzed reactions are the production of hydrogen peroxide through glucose oxidase activity and the conversion of hydrogen peroxide to water and oxygen by catalase enzymes. Production of hydroxymethylfurfural (HMF) from glucose or fructose is an example of non-enzymatic reactions in honey.

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“…Nevertheless, MGO is ubiquitously present in all kinds of foods, especially in those containing high amounts of carbohydrates and lipids and underwent thermal processing. It is generated dominantly through the Maillard reaction in thermally processed foods when hexoses initially react with amino acids to generate Schiff bases, and convert to Amadori products, which undergo a serial of reaction steps to yield MGO ( 5 ). In foods containing high amounts of hexoses, such as honey, MGO is produced by the autoxidation of hexoses, which involves retro-aldol condensation, isomerisation and consequent fragmentation of sugars ( 6 ).…”

Section: Introductionmentioning

confidence: 99%

“…However, dihydroxyacetone do not contribute to the formation of MGO in other foods because of its absence. Oxidation of unsaturated fatty acids is another important pathway for the generation of MGO in fatty foods ( 5 , 9 ). Moreover, MGO could also be generated through the microbial metabolism of dihydroxyacetone phosphate by the catalysis of methylglyoxal synthase, which explains its occurrence in some fermented beverages and foods ( 10 ).…”

Section: Introductionmentioning

confidence: 99%

Formation and metabolism of 6-(1-acetol)-8-(1-acetol)-rutin in foods and in vivo, and their cytotoxicity

Chen

Liu²,

Zhou³

et al. 2022

Front. Nutr.

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Methylglyoxal (MGO) is a highly reactive precursor which forms advanced glycation end-products (AGEs) in vivo, which lead to metabolic syndrome and chronic diseases. It is also a precursor of various carcinogens, including acrylamide and methylimidazole, in thermally processed foods. Rutin could efficiently scavenge MGO by the formation of various adducts. However, the metabolism and safety concerns of the derived adducts were paid less attention to. In this study, the optical isomers of di-MGO adducts of rutin, namely 6-(1-acetol)-8-(1-acetol)-rutin, were identified in foods and in vivo. After oral administration of rutin (100 mg/kg BW), these compounds reached the maximum level of 15.80 μg/L in plasma at 15 min, and decreased sharply under the quantitative level in 30 min. They were detected only in trace levels in kidney and fecal samples, while their corresponding oxidized adducts with dione structures presented as the predominant adducts in kidney, heart, and brain tissues, as well as in urine and feces. These results indicated that the unoxidized rutin-MGO adducts formed immediately after rutin ingestion might easily underwent oxidation, and finally deposited in tissues and excreted from the body in the oxidized forms. The formation of 6-(1-acetol)-8-(1-acetol)-rutin significantly mitigated the cytotoxicity of MGO against human gastric epithelial (GES-1), human colon carcinoma (Caco-2), and human umbilical vein endothelial (HUVEC) cells, which indicated that rutin has the potential to be applied as a safe and effective MGO scavenger and detoxifier, and AGEs inhibitor.

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Alpha-Dicarbonyl Compounds

Cited by 12 publications

References 70 publications

Acceleration effect of galacturonic acid on acrylamide generation: evidence in model reaction systems

Acceleration effect of galacturonic acid on acrylamide generation: evidence in model reaction systems

Biochemical Reactions and Their Biological Contributions in Honey

Formation and metabolism of 6-(1-acetol)-8-(1-acetol)-rutin in foods and in vivo, and their cytotoxicity

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