Glucose Maillard reaction products

YOKDTA A, MiYATA K, MURAGUCHi H and TAKAHASHi A (1987) Effect of glucose on the antioxidative activity of Maillard reaction products during extmsion cooking , Nippon Nogeikagaku Kaishi, 61 (10) 1273-8. 

Characterization of Antioxidative Maillard Reaction Products from Histidine and Glucose... 

Maillard reaction products were obtained by refluxing 100 ml of distilled water containing 0.1 mol L-histidine monohydrochloride mono-hydrate and 0.05 mol D-glucose for 20 h. The pH of the reaction mixture was adjusted to 7.0 with potassium hydroxide before starting the reaction. 

Figure 2. Influence of pH on the formation of precipitate in the retentate of Maillard reaction products from histidine and glucose.

Table IV. Effect of Maillard reaction products (2-methylpyridine or 2,5-dimethylpyrazine) on the mutagenic activity of different model reaction mixtures (creatinine, D-glucose, amino acid in diethylene glycol-water 6 1, v/v) after 4 h of refluxing, 10-yl samples being directly withdrawn from the reaction mixtures and assayed with TA98 after S9 activation.

Bosetto, M., Arafaioli, P., and Pantani, O. L. (2002). Study of the Maillard reaction products formed by glycine and D-glucose on different mineral substrates. Clay Miner. 37, 195-204. 

D. D. Roberts and T. E. Acree, Gas chromatography-olfactometry of glucose-proline Maillard reaction products, in Thermally Generated Flavors, T. H. Parliment, M. J. Morello, and R. J. McGorrin (eds), American Chemical Society, Washington, DC, 1994, 71-79. 

Y. Yoshimura, T. Iijima, T. Watanabe, and H. Nakazawa, Antioxidative effect of Maillard reaction products using glucose-glycine model system, J. Agric. Food Chem., 1997, 45, 4106 1109. 

M. Tanaka, C. W. Kuei, W. Yuji, and T. Taguchi, Application of antioxidative Maillard reaction products from histidine and glucose to sardine products, Nippon Suisan Gakk., 1988, 54, 1409-1414, via Chem. Abstr., 1988, 109, 169145f. 

Kitts, D.D., Wu, C.H., Stich, H.F., and Powrie, W.D. 1993. Effect of glucose-lysine Maillard reaction product on bacterial and mammalian cell mutagenesis. J. Agric. Food Chem. 41, 2353-2358. 

Lingnert, H., Eriksson, C., Waller, G.R. 1983. Characterization of anti-oxidative Maillard reaction products from histidine and glucose. In The Maillard Reaction in Food and Nutrition (G.R. Waller, M.S. Feather, eds.), pp. 335-345, ACS Symposium Series 215, American Chemical Society, Washington, DC. 

Reduction of yeast growth inhibitors— High glucose concentration, Maillard reaction products, and so on. 

Interestingly, some Maillard reaction products have antioxidant activity (reviewed in ref. [29]), the Maillard reaction products from the amino acid-sugar combination of histidine and glucose having stronger antioxidant properties than other combinations [30]. 

Cooking starch in the presence of amino acids may favour the occurrence of Maillard reactions, lowering the bioavailability of lysine in the diet. 13C CPMAS was used to follow the effect of Maillard reactions on the bioavailability of potato starch.124 A loss of crystallinity was found for the three samples studied starch, amylopectin, and amylose, being more marked for amylose. A similar study on chestnut starch indicated that Maillard reactions do not influence significantly its digestibility.125 NMR was used to characterize some Maillard reaction products extracted from model reactive mixtures such as starch-glucose-lysine 126 and lactose-lysine.127... 

Its formation from rhamnose heated with piperidine acetate in ethanol, under the same conditions that produced amino-hexose-reductones from glucose and other hexoses, was described as early as 1963 by Hodge et al., who confirmed the structure by IR and NMR data and proposed a formation pathway. The formation from Amadori intermediates was been reviewed by Vernin (1981). Numerous model systems have confirmed that it is one of the main Maillard-reaction products. For instance we will mention the formation from L-rhamnose and ethylamine (Kato et al., 1972) and from pentose/glycine or alanine, whose mechanism was proposed by Blank and Fay (1996) and Blank et al. (1998), from the intermediate Amadori compound, /V-(l-deoxy-D-pentos-l-yl)glycine. Furaneol is also formed by recombination of... 

As explained by Ledl (1990), this pyranone, which has been detected in many heated or stored foods and results from the ring closure of a hexose, was previously isolated by Severin and Seilmeier (1968) and identified by Mills et al. (1970). It is a Maillard reaction product of glucose and glycine and has a mutagenic activity (Ref. 33 in Hiramoto et al., 1998). 

In order to study the influence of the pH value on the sweetness enhancing effect of the novel Maillard reaction product, binary mixtures of the tasteless alapyridaine and the sweet tasting compounds glucose, saccharose, or L-alanine were sensorially evaluated in a triangle test using water with pH 5.0, 7.0 and 9.0, and the sweet detection thresholds determined were compared to the threshold concentrations of aqueous solutions containing the sweet tastants alone (Table I). 

In our investigation on the effect of Maillard reaction products on the absorption of tryptophan (36), the kinetics of the absorption of tryptophan in the presence of Maillard reaction products formed in the glucose-tryptophan system was studied by bott vitro everted gut sac method and vivo catherization of the portal vein. Fructose-L-tryptophan (Amadori compound) appeared to be the major fraction of the reaction products when fractionated using a cellulose column eluted by water-saturated n-butanol. The absorption of L-tryptophan was partially inhibited vitro and vivo by fructose-L-tryptophan in a competitive manner with an inhibitor constant (Ki) of l.lmM. The relative absorption rate of L-tryptophan was significantly lower in the presence of the Maillard reaction products than in the presence of fructose-L-tryptophan indicating the presence of other inhibitory factors in the reaction products. The in vivo absorption of fructose-L-tryptophan was almost negligible compared to that of tryptophan. The inhibited absorption by Maillard reaction products, may have contributed in part to an incomplete recovery in the growth of the rats when fed a supplemented browned synthetic amino acid diet. 

Lertittikul, W., Benjakul, S., and Tanaka, M. Characteristics and antioxidative activity of Maillard reaction products from a porcine plasma protein-glucose model system as influenced by pH, Food Chem., 100, 669, 2007. 

Yen, G. C. and Chau, C. F. 1993. Inhibition by xylose-lysine Maillard reaction products of the formation of MelQx in a heated creatinine, glycine, and glucose model system. Biosci. Biotech. Biochem. 57 664-665. 

Measurement of Antioxidative Activity. The antioxidative activity of the Maillard reaction products was evaluated by a method similar to that developed by Macku and Shibamoto (9) and later modified by Eiserich et al. 10). The antioxidative activities of 25 iiL-aliquots of peanut oil/cysteine and peanut oil/methionine dichloromethane extracts and 5 nL-aliquots of the glucose/cysteine extracts were measured. 2-Alkyl-thiophenes, 2-thiophenethiol, 2-methyl-3-furanthiol, fiirfuryl mercaptan, thiazolidine, and 1,3-dithiolane were tested for antioxidative activity at a concentration of 1 mM. The above extracts and standards were added to dichloromethane solutions containing 25 mg of heptanal. Nonadecane (400 mg) was added as a gas chromatographic internal standard, and the resulting solutions were brought to a 5-mL final volume with... 

Utsunomiya, N. Hayase, F. Kato, H. Antioxidative activities of Maillard reaction products of D-glucose with ovalbumin hydrolyzed by proteases, and their synergistic effect with tocopherols. Nippon Eiyo Shokuryo Gakkaishi. 1983, 36, 461-465. 

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