Maillard reaction products

Fig. 12.—Carbonyl-amine reactions leading to Maillard reaction products and reductones (adapted from Ref. 51a).

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. 

A number of Maillard reaction products have been found to be mutagenic or carcinogenic (Lee and Shibamoto, 2002). Reactions of the lysine residue with other food components, including dehydroascorbic acid, result in crosslinking of the heated protein (Fayle et al., 2000). 

The extent of heat-induced changes in protein-rich foods can be measured by determining some early Maillard reaction products (O Brien and Morrissey, 1989). Acid treatment of protein-bound or free A -fructoselysine liberates lysine, with a yield of 50%, and two other amino acids, furosine (20%) and pyridosine (10%) (Figure 13.1). The three products that result from hydrolysis of A -lactuloselysine are formed in the proportions of approximately 5 3 to 4 1 to 2, however the yield of different derivatives is variable. Therefore, in order to use these unique amino acids as indicators of changes in lysine content, the hydrolysis should be carried out in strictly-defined conditions. Furosine is present in various food products in a very wide range of concentrations (Table 13.2). 

Kobayashi S, Koga K, Hayashida O, Nakano Y and Hasegawa Y (1990) Specific inhibition of insoluble glucan synthase (GTF-1) by Maillard reaction products from casein and albumins. Agric Biol Chem 54, 1417-1424. 

Liardon R, De Weck-Gaudard D, Philippossian G and Finot P-A (1987) Identification of N-carboxymethyllysine a new Maillard reaction product, in rat urine. J Agr Food Chem 35, 427-431. 

As part of extensive studies lasting over 30 years on the structures of chromophores involved in nonenzymatic browning reactions, two intensely orange, previously unknown, compounds have been identified (2R,8aR)-l and ZS, 8aR)-4-(2-furyl)-7-[(2-furyl)methylidene]-2-hydroxy-2//,7//,8a//-pyrano[2,3-3]pyran-3-one <1998CAR215>. Additional studies on the single Maillard reaction products of these compounds have also been reported <1998JFA3912>. 

Human perception of flavor occurs from the combined sensory responses elicited by the proteins, lipids, carbohydrates, and Maillard reaction products in the food. Proteins Chapters 6, 10, 11, 12) and their constituents and sugars Chapter 12) are the primary effects of taste, whereas the lipids Chapters 5, 9) and Maillard products Chapter 4) effect primarily the sense of smell (olfaction). Therefore, when studying a particular food or when designing a new food, it is important to understand the structure-activity relationship of all the variables in the food. To this end, several powerful multivariate statistical techniques have been developed such as factor analysis Chapter 6) and partial least squares regression analysis Chapter 7), to relate a set of independent or "causative" variables to a set of dependent or "effect" variables. Statistical results obtained via these methods are valuable, since they will permit the food... 

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

This book is a result of the first symposium on the Maillard reaction held in this country (the second in the world2). Panel discussions with audience participation were held on the subjects of food and nutritional benefits of Maillard reaction products and the toxicology of Maillard reaction products but are not reported here. Interaction between participants during this meeting helped cement relations for continued help and perhaps will promote some new areas for cooperative research between American and foreign scientists. This symposium was also an important element in the training of graduate students it provided them with increased awareness of the breadth of the scientific field. We hope that it is true of each of you ... 

The oral administration of Maillard reaction products caused an increase in the growth of both aerobic and anaerobic lactobacilli in the microflora of rats (60). 

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... 

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. 

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

Meat aroma is not the result of one chemical constituent but the sum of the sensory effects of many of these volatiles. Over 90% of the volume of volatile constituents from freshly roasted beef is from lipid, but approximately 40 percent of the volatiles from the aqueous fraction are thought to be heterocyclic compounds, many resulting from Maillard reaction products or their interactions with other ingredients. 

Maillard reaction products formed by interaction of reducing sugar and amino acids such as a-dicarbonyl compounds, aldehydes, hydrogen sulfide, and ammonia can react further to form derivatives that have been identified from meat or its components during heating. Important reviews of sulfur compounds that might be produced by these reactions have been published by Schutte (35) and... 

Figure 6. Interaction of Maillard reaction products to form pyrazines (54).

Sensory Properties of Volatile Maillard Reaction Products and Related Compounds... 

Literature information about the sensory properties for nearly 450 Maillard reaction products has been compiled in a survey. It includes qualitative aroma and flavor descriptions as well as sensory threshold values in different media for the compounds, classified according to their chemical structure. 

The majority of the compounds in this compilation are Maillard reaction products and likewise recognized as important aroma and flavor substances in foods. 

Since this compilation concerns volatile Maillard reaction products, a brief presentation of different types of substances in this group is justified. The classification system given by Nursten (1980-1981) (2) has been a valuable tool. The volatiles may be classified into three groups... 

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. 

The studies reviewed demonstrate that browning products produced on retorting of meat inhibit development of WOF, so that canned meat products are not subject to this flavor defect. The flavor of canned meat is less desirable, however, than that of freshly cooked meat. Nevertheless, the strong inhibitory action of the Maillard reaction products against WOF suggests that they could be useful in preventing development of WOF, so further research in this area could be fruitful. 

Maillard reaction products are being manufactured commercially today by detailed, proprietary processes which are not given by any patent. 

Knox Ingredients Technology (KIT), successor to Knox Gelatine, a wholly owned subsidiary of Thomas J. Lipton, Inc., is a major producer of HVP s, and of a line of "Tastemaker Natural and Artificial Flavorings" based on them. Recent press releases by KIT are quite explicit about the role of Maillard reaction products in the more sophisticated versions of these flavoring agents. 

Wm. M. Bell Co., Melrose Park, Illinois, is one of the companies active in this technology. They incorporate Maillard reaction products into a variety of flavors, including chocolate. 

Maillard Reaction Products as Indicator Compounds for Optimizing Drying and Storage Conditions... 

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

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