Amine, fish formation

The fishy aroma of seafood is incorrectly attributed to trimethyl amine. Flavor formation in fresh and saltwater fish results from complex enzymatic, oxidative, and microbial reactions of n-3 polyunsaturated fatty acid precursors (e.g., eicosapentaenoic acid) (69,70). Hence, fish flavor is mostly composed of non-characterizing planty or melon-like aromas from lipid-derived unsaturated carbonyl compounds. Examples are (Z)-l,5-octadien-3-one ( geranium-like ) in boiled cod (71) and (7i,Z)-2,6-nonadienal ( cucumber-like ) in boiled trout (72). 

Biogenic amine formation in fish and fish products. 

Leuschner, R.G.K. and Hammes, W.P. (1999). Formation of biogenic amine in mayonnaise, herring and tuna fish salad by lactobacilli, Int. J. Food Sci. Nutr., 50, 159. 

Wendakoon, C. and Sakaguchi. M. (1992A). Elfects of spices on growth of and biogenic amine formation by bacteria in fish muscle, in Huss, H., Jakobsen, M. and Liston, J., Quality Assurance in the Fish Industry, Developments in Food Science, Elsevier, Amsterdam, pp. 305-313. 

Amine build-up in fish muscle usually results from decarboxylation of amino acids in the muscle by enzymes of bacterial origin. This review will present information on the activity of bacterial decarboxylases and the formation of amines in fish. Mechanisms of decarboxylase action and production of bacterial decarboxylases in fish muscle are discussed. Emphasis is placed upon studies dealing with formation of histidine decarboxylase and histamine. Histamine, because of its involvement in Scombroid food poisoning, has been extensively studied with regard to its formation in fish and fishery products. 

Examples of amines that frequently occur in fish muscle include cadaverine from lysine, putrescine from ornithine and histamine from histidine. Histamine, because of its involvement in Scombroid food poisoning (histamine intoxication), has been extensively studied with respect to factors influencing its formation in many different fish species. Tuna and other fish from the families Scomberesocidae and Scombridae and a non-scombroid fish, mahi-mahi (dolphin fish) have been most... 

Because amine formation in fish muscle and other foods usually results from bacterial growth with concomitant production of a bacterial decarboxylase, this paper will concentrate on the mechanisms of bacterial decarboxylation and factors influencing the production and activity of the enzymes. Also, because of the overall scope of the subject, the availability of excellent reviews on bacterial decarboxylation (2, 3) and the public health importance of histamine in fish and fishery products, this paper will primarily be limited to a discussion of histidine decarboxylase (EC 4.1.1.22) and the formation of histamine in fish muscle. 

It is further recommended that amine-nitrite mixtures be kept away from electrophilic carbonyl compounds and gem-di-halides capable of supporting immonium ion formation, for example in the preservation of amine-rich fish products with formaldehyde ( ) or in the use of methylene chloride as an aerosol propellant (13). It also seems advisable to avoid storing treflan and related herbicides in the presence of... 

Figure 11.4. Structures of various heterocyclic amines. IQ is 2-amino-3-methylimidazo-quinoline. MelQx is 2-amino-3,8-dimethylLtnidazo-quinoxalme. 4,8-DiMelQx is 2-amino-3,4,8-trimethylimidazo-quinoxaline. PhIP is 2-amino-l-methyl-6-phenylimidazo-pyridine. These and other related compounds can be found in fried or broil beef, fish, and chicken, but can also be created by cooking mixtures of creatinine, amino acids, and glucose. Microwave cooking, or cooking in aluminum foil, reduces the formation of heterocyclic amines. (From Sugimura, 1997.)...

Fish muscle can support formation of a wide variety of amine compounds resulting from the direct enzymatic decarboxylation of amino acids. The substrate for the decarboxylase enzymes are free amino acids, therefore amine build-up normally occurs during a decomposition or spoilage process involving formation of free amino acids through proteolysis together with bacterial production and action of an amino acid decarboxylase (Eitenmiller... 

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