Browning reactions of Heyns rearrangement products

Pilková, L.; Pokorný, Jan; Davı́dek, J.

doi:10.1002/food.19900340821

Cited by 20 publications

(4 citation statements)

References 12 publications

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“…Glucose-derived Amadori compounds—amino-deoxyfructos-1-yl adducts, represent the best characterized glycation products [8]. Ketoamine intermediates undergo a similar reaction cascade, known as Heyns rearrangement [9], i.e., migration of a proton from C2 to C1 leading to the formation of 2-amino-deoxyaldos-1-yl adducts (Heyns products) [10,11]. These first relatively stable intermediates of glycation, known as “early glycation products” [12] are readily involved in further degradation, oxidation and cross-linking reactions, yielding “advanced glycation end products” (AGEs) [13].…”

Section: Introductionmentioning

confidence: 99%

Glycation of Plant Proteins: Regulatory Roles and Interplay with Sugar Signalling?

Shumilina

Kusnetsova

Tsarev

et al. 2019

IJMS

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Glycation can be defined as an array of non-enzymatic post-translational modifications of proteins formed by their interaction with reducing carbohydrates and carbonyl products of their degradation. Initial steps of this process rely on reducing sugars and result in the formation of early glycation products—Amadori and Heyns compounds via Schiff base intermediates, whereas their oxidative degradation or reactions of proteins with α-dicarbonyl compounds yield a heterogeneous group of advanced glycation end products (AGEs). These compounds accompany thermal processing of protein-containing foods and are known to impact on ageing, pathogenesis of diabetes mellitus and Alzheimer’s disease in mammals. Surprisingly, despite high tissue carbohydrate contents, glycation of plant proteins was addressed only recently and its physiological role in plants is still not understood. Therefore, here we summarize and critically discuss the first steps done in the field of plant protein glycation during the last decade. We consider the main features of plant glycated proteome and discuss them in the context of characteristic metabolic background. Further, we address the possible role of protein glycation in plants and consider its probable contribution to protein degradation, methylglyoxal and sugar signalling, as well as interplay with antioxidant defense.

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Section: Introductionmentioning

confidence: 99%

Glycation of Plant Proteins: Regulatory Roles and Interplay with Sugar Signalling?

Shumilina

Kusnetsova

Tsarev

et al. 2019

IJMS

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“…Labuza and Baiser (1992a,b) consider that the browning processes presents an induction period followed by another period of pseudo-zero order. Nevertheless, such a period has not been observed in some model systems heated to 110 °C, and pH between 4 and 10 (Pilkova et al, 1990). Milk and concentrated milk heating induces important chemical changes in casein micelles, such as the saturation of calcium phosphate in the soluble phase which, in turn, constitutes the micelle (Fox, 1986).…”

Section: Resultsmentioning

confidence: 97%

Kinetics of heat-induced browning in concentrated milk with sucrose as affected by pH and temperature / Cinética del pardeamiento inducido por calor en sistemas de leche concentrada con alto contenido de sacarosa. Influencia del pH y de la temperatura

Pauletti

Matta

Rozycki

1999

Food sci. technol. int.

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A model system constituted by whole dry milk powder, sucrose, and distilled water was used to establish kinetic parameters of the heat-induced browning process (HIBP). Second-order central com posite design was chosen with pH and temperature as selected variables. Color response was the Kubelka-Munk index (K/S) calculated from reflectance colorimetric measures as a function of time using the self-backing reflectance transformation (SBRT) procedure. Results showed that HIBP pseudo- order reactions were variable between 0 and 0.6. Reaction rate coefficient (k) was strongly dependent on pH and temperature. In general, k increased as both pH and temperature increased but the influ ence of temperature was higher than that of pH. Q10 was dependent on temperature, ranging be tween 2.15 at 130-140 °C and 2.44 at 100-110 °C, whatever the pH. k values were analyzed with the Arrhenius expression. Values of Ea, calculated for different pH, were coincident (25.34 kcal/M).

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“…The pronounced increase was observed after the addition of glucose or fructose to semolina, slightly more intensive in mixture with glucose than in a mixture with fructose. It may be due to differences in reaction rates of browning intermediates between Amadori (POKORNÝ et al 1988) and Heyns (PILKOVÁ et al 1990) rearrangements. The increase of a* and b* corresponds to the increase in redness and yellowness, respectively, which occurs in the beginning of nonenzymic browning.…”

Section: Resultsmentioning

confidence: 99%

Changes during the extrusion of semolina in mixture with sugars

Farouk¹,

Pudil²,

Janda³

et al. 2001

Czech J. Food Sci.

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Wheat semolina and its mixtures with 5% glucose, fructose of sucrose were processed in a sigle screw extruder at the maximum temperature of 140°C and the processing time of 30 s. The nonenzymic browning was only moderate, but it was substantially more intensive in mixtures with glucose or fructose than in the case of wheat semolina or its mixture with sucrose. Red and yellow pigments were mainly formed. The odour acceptability was affected by the presence of sugars almost negligibly, but the intensities were different, higher in extruded mixtures with glucose and fructose than in wheat semolina or its mixture with sucrose. Small differences were observed in the sensory profile. Extrusion of semolina with sugars produced more sensory active volatiles (52-69 identified compounds) than in extruded semolina (41 compounds). Pyrazines, furans and pyrans were the most important sensory active compounds. Their amounts increased by the addition of sugars to semolina; the mixture of semolina with glucose was particularly rich in active compounds. The formation of pyrazines was more enhanced by the addition of fructose than of other sugars. Maltol, butyrolactone and acetic acid were present in large amounts. Even if sensory characteristics were improved by addition of sugars to semolina, the difference was not very pronounced.

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Browning reactions of Heyns rearrangement products

Cited by 20 publications

References 12 publications

Glycation of Plant Proteins: Regulatory Roles and Interplay with Sugar Signalling?

Glycation of Plant Proteins: Regulatory Roles and Interplay with Sugar Signalling?

Kinetics of heat-induced browning in concentrated milk with sucrose as affected by pH and temperature / Cinética del pardeamiento inducido por calor en sistemas de leche concentrada con alto contenido de sacarosa. Influencia del pH y de la temperatura

Changes during the extrusion of semolina in mixture with sugars

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