Formation of proline- and hydroxyproline-specific Maillard products from [1-13C]glucose

Tressl, Roland; Helak, Bernd; Kersten, E.; Rewicki, Dieter

doi:10.1021/jf00028a008

Cited by 41 publications

(35 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Specifically at pH 5.5, 36.8%, 79.2% and 101.3% more 3-DG were produced after adding 0.5, 5.0 and 50 lmol/ml CGA, respectively (Table 1). CGA did not increase the formation of furfural, a product produced from the dehydration of 3-deoxyosulose (Tressl, Helak, Kersten, & Rewicki, 1993) at pH 5.5 significantly, but slightly increased 3-DG formation at pH 7.0 after the addition of 50.0 lmol/ml CGA. At pH 5.5, CGA did not influence the formation of MGO, a cleavage product of 3-DG (Nuesten, 2005); however, CGA reduced its formation at pH 7.0 (Table 1).…”

Section: Effect Of Cga On Hmf Formationmentioning

confidence: 80%

Chlorogenic acid increased 5-hydroxymethylfurfural formation when heating fructose alone or with aspartic acid at two pH levels

Zhang

Zou

et al. 2016

Food Chemistry

View full text Add to dashboard Cite

Section: Effect Of Cga On Hmf Formationmentioning

confidence: 80%

Chlorogenic acid increased 5-hydroxymethylfurfural formation when heating fructose alone or with aspartic acid at two pH levels

Zhang

Zou

et al. 2016

Food Chemistry

View full text Add to dashboard Cite

“…However, 3‐DG is not only a precursor of pyrraline, but also an important precursor of other compounds in the Maillard reaction. Proline‐ and hydroxyproline‐specific heterocyclic volatiles can be produced from glucose via the 3‐DG pathway (Tressl and others ). In addition, other compounds, such as pyrazines (Weenen and others ) and melanoidins (Martins and van Boekel ), can also be formed via the 3‐DG pathway.…”

Section: Resultsmentioning

confidence: 99%

Kinetic Study on Peptide‐Bound Pyrraline Formation and Elimination in the Maillard Reaction Using Single‐ and Multiple‐Response Models

Liang

et al. 2016

Journal of Food Science

View full text Add to dashboard Cite

Pyrraline, an advanced glycation end product (AGE), is related to some chronic diseases and can be employed as an indicator for heat damage in food processing. In this study, the impact of changing the reactant concentration and ratio on the kinetic parameters describing peptide-bound pyrraline (pep-pyr) formation and elimination was evaluated in the Lys-Gly/glucose model systems, with microwave heating treatment ranging from 120 to 200 °C. The maximum pep-pyr concentration increased as follows: 200 °C ˂ 180 °C ˂ 160 °C ˂ 120 °C ˂ 140 °C. First, the pep-pyr formation and elimination was modeled by using a single-response modelling. The formation rate constant (k ) of pep-pyr was independent of the initial concentration of the reactants and ratios. However, the elimination rate constant of pep-pyr (k ) increased with increasing reactant concentrations. Second, a multiresponse modelling was performed to illustrate the pathways of pep-pyr formation and elimination. Two adapted models can fit to the experimental data with the goodness-of-fit ranging from 0.663 to 0.920. Glucose-to-fructose isomerization rather than glucose-to-mannose epimerization was detected in an equimolar model system and the model system with an excess of any of the reactants. The caramelization reaction was negligible in the equimolar systems and the model systems with an excess of peptide. The reaction rate constant of glucose-to-fructose isomerization was independent of the initial reactant ratios. It was more difficult for pep-pyr elimination in the model system with an excess of peptide than that in the other 2 model systems (the equimolar system and the system with an excess of glucose), whereas a reverse result in pep-pyr formation was obtained.

show abstract

“…As presented in Table 1, three cyclopent[b]azepin-8(1H)-one compounds, compounds 12, 14, and 15, were found in the 2-deoxyglucose/proline model system. The pathway for the formation of compound 12 and 14 was reported by Tressl et al (1985cTressl et al ( , 1993. 2-Hydroxy-2-cyclopenten-1-one was demonstrated to be an effective precursor for the formation of these two compounds.…”

Section: Resultsmentioning

confidence: 87%

Generation of Proline-Specific Maillard Compounds by the Reaction of 2-Deoxyglucose with Proline

Chen

1997

J. Agric. Food Chem.

View full text Add to dashboard Cite

The proline-specific Maillard products including 2,3-dihydro-1H-pyrrolizines, hexahydro-7H-cyclopenta[b]pyridin-7-ones, and cyclopent[b]azepin-8(1H)-ones were generated by both 2-deoxyglucose/ proline and glucose/proline model reactions at 180°C for 2 h. The amounts of these products generated in 2-deoxyglucose/proline reaction were far less than (<12%) those generated in the glucose/proline model reaction at both pH 9.0 and 4.0. The pH effect on the formation of these products in the 2-deoxyglucose/proline model was not significant, while a lower pH favored the generation of these products in the glucose/proline reaction. The generation of the active precursors of these proline-specific Maillard products from 2-deoxyglucose is proposed.

show abstract

Formation of proline- and hydroxyproline-specific Maillard products from [1-13C]glucose

Cited by 41 publications

References 12 publications

Chlorogenic acid increased 5-hydroxymethylfurfural formation when heating fructose alone or with aspartic acid at two pH levels

Chlorogenic acid increased 5-hydroxymethylfurfural formation when heating fructose alone or with aspartic acid at two pH levels

Kinetic Study on Peptide‐Bound Pyrraline Formation and Elimination in the Maillard Reaction Using Single‐ and Multiple‐Response Models

Generation of Proline-Specific Maillard Compounds by the Reaction of 2-Deoxyglucose with Proline

Contact Info

Product

Resources

About