Dataset Information

Kinetics of ??dicarbonyl compounds formation in glucose-glutamic acid model of Maillard reaction.

ABSTRACT: As a potential health hazard, ?-dicarbonyl compounds have been detected in the thermally processed foods. In order to investigate the formation kinetics of ?-dicarbonyl compounds, liquid chromatography-electrospray tandem mass spectrometry was employed to determine the content of ?-dicarbonyl compounds in glucose-only and glucose-glutamic acid (glucose-Glu) thermal reaction models. The 3-deoxyglucosone content was significantly higher than 6 ?-dicarbonyl compounds at 90-110?, 0-6 hr in the two tested systems. The glutamic acid promoted the content accumulation of 1-deoxyglucosone, diacetyl, methylglyoxal, and glyoxal, whereas inhibited the content of 3-deoxyglucosone and 3,4-dideoxyglucosone. Three-fifths of the tested compounds content increased linearly with time increasing, but in glucose-only system, the 1-deoxyglucosone content increased logarithmically at 95-110? over reaction time. The formation of glucose (100-110?, glucose-only and glucose-Glu), 5-hydroxymethylfurfural (100-110?, glucose-only), 1-deoxyglucose (105-110?, glucose-Glu), 3,4-dideoxyglucosone (110?, glucose-Glu), glyoxal (95-110?, glucose-Glu) and diacetyl (90-95?, glucose-Glu) could be well fitted by exponential equation. Shortening the heating time and reducing heating temperature (except glyoxal in glucose-only system) were the effective methods to decrease ?-dicarbonyl compounds content in the two tested systems. Additionally, high temperature could also reduce ?-dicarbonyl compounds content, such as 3-deoxyglucosone (?110?, glucose-only), 1-deoxyglucosone (?110?, glucose-only), glucosone (?110?, glucose-only; ?100?, glucose-Glu), methyloxyl (?110?, glucose-only; ?100?, glucose-Glu), diacetyl (?110?, glucose-only), and glyoxal (?100?, glucose-Glu).

SUBMITTER: Zhang L

PROVIDER: S-EPMC7802556 | biostudies-literature | 2021 Jan

REPOSITORIES: biostudies-literature

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Kinetics of α‑dicarbonyl compounds formation in glucose-glutamic acid model of Maillard reaction.

Zhang Lili L Sun Ying Y Pu Dandan D Zhang Yuyu Y Sun Baoguo B Zhao Zhiyao Z

Food science & nutrition 20201108 1

As a potential health hazard, α-dicarbonyl compounds have been detected in the thermally processed foods. In order to investigate the formation kinetics of α-dicarbonyl compounds, liquid chromatography-electrospray tandem mass spectrometry was employed to determine the content of α-dicarbonyl compounds in glucose-only and glucose-glutamic acid (glucose-Glu) thermal reaction models. The 3-deoxyglucosone content was significantly higher than 6 α-dicarbonyl compounds at 90-110℃, 0-6 hr in the two t ...[more]

PMID: 33473293

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Project description:Glucose-lysine based Maillard reaction products (MRPs) are introduced to the human body via food ingestion or are synthesized in vivo. Depending on reaction conditions, they represent a mixture of compounds with diverse chemical structures and physiological properties. MRPs may also be a potential nutrient source for Salmonella, a major foodborne gastrointestinal pathogen. This study was designed to determine the growth and transcriptional responses of S. Typhimurium LT2 to MRPs generated at low water activity to simulate the reaction occurring during food processing and storage. Maillard reactions between N-α-acetyl-lysine and glucose were varied in time (4, 23, and 143 h) to generate sub-samples with prevailing Amadori compound, advanced glycation end products (AGEs), or melanoidines respectively. The addition of MRP up to 5 mg mL-1 to defined media with 0.4% glucose had no effect on S. Typhimurium LT2 growth. In media, where the MRP sub-samples (4 and 23 h) served as the only carbon source, MRP assimilation by S. Typhimurium LT2 was observed as secondary logarithmic growth phases (0.063 h-1 and 0.072 h-1) after the growth on glucose available in the MRP reaction mixtures (0.479 h-1). The MRPs sub-sample with the highest concentration of melanoidines (143 h) also supported S. Typhimurium LT2 growth (0.368 h-1). Of the three MRPs sub-samples, the Amadori compound was the preferred carbon source for S. Typhimurium LT2 as evidenced by its almost complete disappearance (98%). Decreases in AGEs (37%) and melanoidines (15%), when incubated with S. Typhimurium LT2, also occurred. Transcription profiles of the cells grown on the MRPs fractions revealed predominant up-regulation of genes associated with the functional groups of energy metabolism, fatty and phospholipid metabolism, cellular process, and regulatory functions, and general down-regulation of the genes in the groups of amino acid biosynthesis, protein synthesis and transcription, transport and binding proteins, and DNA metabolism. The carbon flow in tricarboxylic acid (TCA) cycle partitioned by the glyoxylate cycle appeared to play an essential role in the assimilation of glucose-lysine-derived MRPs. The high expression level of numerous genes encoding hypothetical proteins or proteins with unknown function suggested the presence of genes whose role in glucose-lysine MRPs catabolism in Salmonella remains to be determined.

Project description:Glucose-lysine based Maillard reaction products (MRPs) are introduced to the human body via food ingestion or are synthesized in vivo. Depending on reaction conditions, they represent a mixture of compounds with diverse chemical structures and physiological properties. MRPs may also be a potential nutrient source for Salmonella, a major foodborne gastrointestinal pathogen. This study was designed to determine the growth and transcriptional responses of S. Typhimurium LT2 to MRPs generated at low water activity to simulate the reaction occurring during food processing and storage. Maillard reactions between N-Î±-acetyl-lysine and glucose were varied in time (4, 23, and 143 h) to generate sub-samples with prevailing Amadori compound, advanced glycation end products (AGEs), or melanoidines respectively. The addition of MRP up to 5 mg mL-1 to defined media with 0.4% glucose had no effect on S. Typhimurium LT2 growth. In media, where the MRP sub-samples (4 and 23 h) served as the only carbon source, MRP assimilation by S. Typhimurium LT2 was observed as secondary logarithmic growth phases (0.063 h-1 and 0.072 h-1) after the growth on glucose available in the MRP reaction mixtures (0.479 h-1). The MRPs sub-sample with the highest concentration of melanoidines (143 h) also supported S. Typhimurium LT2 growth (0.368 h-1). Of the three MRPs sub-samples, the Amadori compound was the preferred carbon source for S. Typhimurium LT2 as evidenced by its almost complete disappearance (98%). Decreases in AGEs (37%) and melanoidines (15%), when incubated with S. Typhimurium LT2, also occurred. Transcription profiles of the cells grown on the MRPs fractions revealed predominant up-regulation of genes associated with the functional groups of energy metabolism, fatty and phospholipid metabolism, cellular process, and regulatory functions, and general down-regulation of the genes in the groups of amino acid biosynthesis, protein synthesis and transcription, transport and binding proteins, and DNA metabolism. The carbon flow in tricarboxylic acid (TCA) cycle partitioned by the glyoxylate cycle appeared to play an essential role in the assimilation of glucose-lysine-derived MRPs. The high expression level of numerous genes encoding hypothetical proteins or proteins with unknown function suggested the presence of genes whose role in glucose-lysine MRPs catabolism in Salmonella remains to be determined. This study was designed to determine the growth and transcriptional responses of S. Typhimurium LT2 to MRPs generated at low water activity to simulate the reaction occurring during food processing and storage. Maillard reactions between N-Î±-acetyl-lysine and glucose were varied in time (4, 23, and 143 h) to generate sub-samples with prevailing Amadori compound, advanced glycation end products (AGEs), or melanoidines respectively. Total bacterial RNA was isolated as previously described and the RNA samples were then converted to fluorescently-labeled cDNA and hybridized to S. Typhimurium microarrays version 5 (NIAID's Pathogen Functional Genomics Resource Center). Real-time PCR and physiological experiments were performed to validate the microarray data. In all supplementary files channel A = Cy3, channel B = Cy5.

Project description:Isocyanic acid, HNCO, mainly emitted by combustion processes, is doubted to be detrimental to human health if its concentration surpasses ∼1 ppbv. Very little information has been found regarding the HNCO loss in the gas phase. This study aims to close this knowledge gap by performing a theoretical kinetic study on the reaction of HNCO with the propargyl radical. The potential energy surface of the HNCO + C3H3 reaction was characterized utilizing high-level CCSD(T)/CBS(TQ5)//B3LYP/6-311++G(3df,2p) quantum-chemical approaches, followed by TST and RRKM/ME kinetic computations. The obtained results reveal that the reaction can proceed via H-abstraction, leading to the C3H4 + NCO bimolecular products with energy barriers of 23-25 kcal/mol, and/or addition, resulting in C4H4NO intermediates with 23-26 kcal/mol barrier heights. The C4H4NO adducts when formed can decompose to products and/or return to HNCO + C3H3 in which the reverse decompositions are found to be dominant with a branching ratio that accounts for nearly 100% at 300 K and 760 Torr. The calculated P-independent rate coefficients indicate that at low temperatures, the H-abstraction channels are insignificant. However, at high temperatures (T > 1500 K), the H-abstraction path leading to H3CCCH + NCO prevails with a branching ratio of ∼50-53% in the descending 1800-1500 K temperature range at 760 Torr, while the H-abstraction leading to H2CCCH2 + NCO is favorable at T > 1800 K, with the yield reaching above 50% at 760 Torr. In contrast to the H-abstraction rate constants, the calculated values for the additions and the C4H4NO decompositions show a positive pressure dependence. Both the total rate constants for the reactions HNCO + C3H3 → products and C4H4NO → products, which are, respectively, k _total_bimo(T) = 3.53 × 10-23 T 3.27 exp[(-21.35 ± 0.06 kcal/mol)/RT] cm3 molecule-1 s-1 and k _total_uni(T) = 1.13 × 1025 T -4.02 exp[(-11.77 ± 0.16 kcal/mol)/RT] s-1, increase with the increasing temperature in the 300-2000 K range at 760 Torr. The rate constant of HNCO + C3H3 → products is about 8 orders of magnitude smaller than the value of HCHO + C3H3 → products, showing that HCHO is more reactive toward the C3H3 free radicals than HNCO. The computed heats of formation for several species agree well with the available literature data with the deviation less than 1.0 kcal/mol, indicating that the methods used in this study are extremely reliable. With the given results, it is vigorously suggested that the predicted rate constants, together with the thermodynamic data of the species involved, can be confidently used for modeling HNCO-related systems under atmospheric and combustion conditions.

Dataset Information

Kinetics of ??dicarbonyl compounds formation in glucose-glutamic acid model of Maillard reaction.

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Kinetics of α‑dicarbonyl compounds formation in glucose-glutamic acid model of Maillard reaction.

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