Antioxidative Maillard reaction

An antioxidative Maillard reaction product (AX) can be formed from arginine and xylose. Optimum results were obtained by refluxing 1M arginine-HCl with 1M xylose in water at 100°C for 10-20 h at initial pH of approximately 5. 

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

A. J. Bedinghaus and H. W. Ockerman, Antioxidative Maillard reaction products from reducing sugars and free amino acids in cooked ground pork patties, J. Food Sci., 1995, 60, 992-995. 

H. Lingnert and G. Hall, Formation of antioxidative Maillard reaction products during food processing, in C, 1986, 273-279. 

H. Lingnert, C. E. Eriksson, and G. R. Waller, Characterization of antioxidative Maillard reaction products from histidine and glucose, in B, 1983, 335-345. 

H. Lingnert, Antioxidative Maillard reaction products. III. Application in cookies, J. Food Proc. Preserv., 1980, 4, 219-233. 

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. 

Lingnert, H. Ericksson, C.E. Antioxidative Maillard reaction products I. Products from sugars and free amino acids. 7. Food Process. Preserv. 1980a, 4, 161-172. 

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. 

At present, antioxidants are extensively studied as supplements for the treatment diabetic patients. Several clinical trials have been carried out with vitamin E. In 1991, Ceriello et al. [136] showed that supplementation of vitamin E to insulin-requiring diabetic patients reduced protein glycosylation without changing plasma glucose, probably due to the inhibition of the Maillard reaction. Then, Paolisso et al. [137] found that vitamin E decreased glucose level and improved insulin action in noninsulin-dependent diabetic patients. Recently, Jain et al. [138] showed that vitamin E supplementation increased glutathione level and diminished lipid peroxidation and HbAi level in erythrocytes of type 1 diabetic children. Similarly, Skyrme-Jones et al. [139] demonstrated that vitamin E supplementation improved endothelial vasodilator function in type 1 diabetic children supposedly due to the suppression of LDL oxidation. Devaraj et al. [140] used the urinary F2-isoprostane test for the estimate of LDL oxidation in type 2 diabetics. They also found that LDL oxidation decreased after vitamin E supplementation to patients. 

The most practical method for preventing WOF in meat products is to add antioxidants prepared from natural precursors such as sugars and amino adds by heating them to produce constituents that not only act as antioxidants but serve to enhance meaty flavor as well. The resulting Maillard products have been known to have antioxidant activity in lipid systems (6-8). It is assumed that the antioxidative property of the Maillard reaction is assodated with the formation of low molecular weight reductones and high molecular weight melanoidins (6, 7, 9-13). 

Lingnert, H. Eriksson, C. E. Antioxidative effect of Maillard reaction products. Prog. Food Nutr. Sci. 1981,... 

Conditions for the Synthesis of Antioxidative Arginine-Xylose Maillard Reaction Products... 

A considerable amount of research pertaining to the Maillard reaction has revolved around the conditions of the reaction (1, 2, 3). However, very little attention has been directed toward the conditions for maximizing the yield of antioxidative products. The studies that have been conducted have focused primarily on very specific reactants, as does this study, and although some generalizations can be drawn about reaction parameters, most reactant combinations used so far have only been treated with a single set of reaction conditions. 

Foster, R. C. "Preliminary isolation and characterization of an antioxidative component of the Maillard reaction between arginine and xylose" M. S. Thesis, Oklahoma State University, Stillwater, Oklahoma, 1980 72 pp. 

Lingnert, H. "Antioxidative effect of Maillard reaction products". ISBN 91-7290-079-2 (SIK-Rapport), Goteborg, 1979. 

Phosphate, ascorbate, NaCl, nitrite, Maillard reaction products, and other antioxidants or prooxidants have been reported to influence development of WOF. Their roles have been reviewed (5), but newer evidence is now available and will be covered herein. 

Sato et a2- (34) demonstrated that a variety of common meat additives, inclucnrTg cottonseed flour, nonfat dry milk, spray-dried whey, wheat germ, and textured soy flour, inhibited WOF in the meat system. These products may have exerted their inhibitory effect on WOF through the Maillard reaction, since most of them contain some reducing sugars. Pratt (40) reported soybeans and soy protein concentrate had an inhibitory effect upon development of WOF and was able to demonstrate that the active components are water soluble. Fractionation and analysis of the water-soluble fraction showed the antioxidant activity was due to the presence of isoflavones and hydroxylated cinnamic acids (40). This confirms earlier work showing that the flavonoTcis present in plant extracts inhibit oxidation in sliced roast beef (41 ). 

The most common antioxidants are phenols, such as butylated hydroxyanisole (BHA) or butylated hydroxytoluene (BHT). Increasing interest has, however, been directed towards the utilization of normal food constituents with antioxidative properties (2). Among those, the Maillard reaction products (MRP) might be of special importance, since they are so widespread in foods. 

The first report on antioxidative effect of MRP was made by Franzke and Iwainsky (3). Shortly afterward Griffith and Johnson (4) reported that the addition of glucose to cookie dough resulted in a better stability against oxidative rancidity during storage of the cookies. Research on antioxidative MRP was then mainly performed by groups in Japan. A symposium on Maillard Reactions in Food held in Uddevalla, Sweden, 1979 included also the aspect of antioxidative properties. The contributions on this subject contained also brief reviews (5, 6, 7). Most of the work has been done on model systems. Some applications in food systems have, however, also been reported (8 - 11). 

Possibly several different compounds formed by the Maillard reaction can exhibit antioxidative properties. Their formation might be dependent on what reactants are used and on the reaction conditions (temperature, time, water content etc.)... 

Table II summarizes the yield and the antioxidative effect of products obtained in the various steps in the purification of the antioxidants from histidine and glucose. The yield is expressed as percent of the starting material, the crude Maillard reaction mixture. The antioxidative effect of the various fractions is compared to that of the crude reaction mixture on a weight basis, the crude reaction mixture being given the value 1. The relative antioxidative effect of 6 for the retentate means, for example, that the retentate gives the same antioxidative effect as the crude reaction mixture with only one sixth of the amount of material. In the table is also shown the calculated "total antioxidative effect" ("yield " x "relative antioxidative effect").

A constant observation when the MRP were separated by various methods was that antioxidative effect was found in many different fractions. Both the dialysates and the retentates from dialysis were antioxidative to some extent. All the electrophoresis fractions exhibited some antioxidative effect. Attempts to separate the MRP by column chromatography on Sephadex G-50 have resulted in several fractions with some antioxidative effect, and so on. This indicates that several antioxidative products are formed by the Maillard reaction, possibly differing in molecular size and chemical structure, but perhaps with one single antioxidative functional group in common, such as a free radical function. However, it can not be excluded that the MRP contain a few entirely different antioxidants with different modes of action. Various mechanisms have also been suggested. Eichner (6) claimed MRP to inactivate the hydroperoxides formed by the lipid oxidation. There are also reports on the complex binding of metals by MRP (18, 19). 

Although the early Maillard reaction products are reported to have antioxidant properties and, in fact, can be utilized by processors to inhibit lipid oxidation in animal protein foods such as fish products, there is an accompanying lysine loss (4 5). 

The Maillard reaction appears to be the one to occur most commonly, accompanied not only by browning but also by change of aroma, loss of nutritional value, and development of antioxidative ac-... 

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