Quinoxalines derived from D-xylose and o-phenylenediamine under acidic refluxed conditions.

Morita, Naofumi; Daido, Yoshiyuki; Hideo, Hayashi; Takagi, Masanosuke

doi:10.1271/bbb1961.47.765

Cited by 7 publications

(8 citation statements)

References 1 publication

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“…This compound was isolated by MLCCC ( t R 120 min, ethyl acetate extract, deaerated incubation setup). NMR results were in line with ref . HR-MS: m / z 257.0897 (found); m / z 257.0898 (calculated for C 12 H 14 O 3 N 2 Na [M + Na] + ).…”

Section: Methodssupporting

confidence: 86%

Novel Insights into the Maillard Catalyzed Degradation of Maltose

Smuda

Glomb

2011

J. Agric. Food Chem.

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Numerous investigations concerning Maillard degradation of carbohydrates clearly depict the important impact of α-dicarbonyl compounds on changes occurring during preparation of food or physiological processes in vivo. To study the formation of these reactive intermediates during degradation of maltose in the presence of lysine, α-dicarbonyl compounds were isolated, identified and quantified after reaction with o-phenylenediamine to form their stable quinoxaline derivatives. Maltosone and 1,4-dideoxyglucosone were synthesized and incubated independently with lysine to investigate follow-up products and to gain further insights into the complex degradation mechanisms. Glyoxylic acid as a dicarbonyl structure and 5,6-dihydroxy-2,3-dioxohexanal as a 1,2,3-tricarbonyl compound were established as novel Maillard degradation products of maltose. Conducted experiments unequivocally demonstrated that inter- and intramolecular redox reactions are of major importance during degradation of disaccharides. 1,4-Dideoxyglucosone, 1-lysino-1,4-dideoxyglucosone, 5,6-dihydroxy-2,3-dioxohexanal, 3,4-dideoxypentosone and glyoxylic acid were found to be the central intermediates involved in the redox chemistry. With the present study we deliver a comprehensive overview on the mechanisms behind α-dicarbonyl compounds evolving from Maillard degradation of maltose.

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Section: Methodssupporting

confidence: 86%

Novel Insights into the Maillard Catalyzed Degradation of Maltose

Smuda

Glomb

2011

J. Agric. Food Chem.

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“…HRGC-FID/MS (methylglyoxal-quinoxaline): tR 17.40 min; m/z 144 (M •+ , 88%), 117 (100), 103 (8), 90 (22), 75 (55), 63 (12), 50 (50).…”

Section: -Ethyl-3-methylquinoxaline (Istd-quinoxaline) and (1s2r)-1-(...mentioning

confidence: 99%

“…After filtration, solvents were evaporated and the residue was subjected to column chromatography with EtOAc. Fractions with material having Rf 0.15 (TLC, EtOAc) were combined and volatiles evaporated to yellowish crystals [250 mg, 66%, spectroscopic data compliant with those of Morita et al (22)].…”

Section: (2s3r)-1-(2-quinoxalinyl)-234-trihydroxybutane (3-dgquinoxal...mentioning

confidence: 99%

Detection of α-Dicarbonyl Compounds in Maillard Reaction Systems and in Vivo

Glomb

Tschirnich

2001

J. Agric. Food Chem.

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alpha-Dicarbonyl compounds are of major interest in food chemistry and biochemistry as important precursors of, for example, protein modifications and flavor. Due to their high reactivity most of the published structures were identified and quantitated as stable derivatives after reaction with trapping reagents. However, the present study showed for the first time that the trapping reagents are of dramatic impact on the final qualitative and quantitative alpha-dicarbonyl spectrum. As important representatives, aminoguanidine and o-phenylenediamine were used to compare trapping characteristics and to monitor the dicarbonyl structures arising from the degradation of an Amadori compound. Dicarbonyl structures with a reductone moiety could not be or were only insufficiently detected by slow-reacting reagents such as aminoguanidine. On the other hand, fast-reacting chemicals such as o-phenylenediamine imposed high oxidative stress on the investigated system and led to enhanced or false positive formation of dicarbonyl compounds generated by oxidative pathways.

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“…Quinoxalines were prepared according to the method of Morita et al (1983) with a slight modification (Morita, Mizutani, Hayashi, Kirihata, Ichimoto, Ueda, et al, 1983 Usui et al (Usui, et al, 2007). MGO-Q was verified in comparison to commercial available materials.…”

Section: Syntheses Of Quinoxalinesmentioning

confidence: 99%

Promotion effect of sulfite on deoxyosones and 4-methylimidazole in caramel model system

2017

Food Chemistry

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In this study, hydrogen-deuterium (H/D) exchange experiment was carried out to reveal the promotion effect of sulfite on the formation of deoxyosones and 4-methylimidazole (4-MeI) in the Maillard reaction. Glucose-ammonium (40mmol/L, pH 7.4 in PBS) model systems with different levels of sulfite were incubated at 110°C for 2h. Alpha-dicarbonyls were detected after derivatization by a high-performance liquid chromatography with a diode array detector (HPLC-DAD). 4-MeI in the Maillard reaction was tested using a high-performance anion exchange chromatography with an electrochemical detector (HPAEC-ED). The H/D exchange ratios of hexose (fructose, glucose and mannose) were tested by HPAEC-MS. Results showed that the aldo-enol transition of enediol was promoted by sulfite, which promoted the formation of deoxyosones and 4-MeI. In addition, the oxidation reaction of enediols was inhibited by the antioxidant sulfite, which caused the inhibition of osones formation in the Maillard reaction.

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Quinoxalines derived from D-xylose and o-phenylenediamine under acidic refluxed conditions.

Cited by 7 publications

References 1 publication

Novel Insights into the Maillard Catalyzed Degradation of Maltose

Novel Insights into the Maillard Catalyzed Degradation of Maltose

Detection of α-Dicarbonyl Compounds in Maillard Reaction Systems and in Vivo

Promotion effect of sulfite on deoxyosones and 4-methylimidazole in caramel model system

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