Amines cadaverine

Commercially available tests use a combination of lysine and glucose. Organisms such as Salmonella which are generally lysine positive will ferment glucose initially to produce an acid reaction, and this will change to an alkaline reaction as the lysine is decarboxylated to the amine cadaverine. Lysine negative species will remain acid. The test medium should be covered with a thin layer of mineral oil to exclude air. 

The starting material for the synthesis of the lupin alkaloids is the amino acid lysine, which is first decarboxylated to give its biogenic amine cadaverine. Two units of cadaverine are then joined via a still hypothetical intermediate to give lupinin. Addition of another cadaverine unit to lupinin gives sparteine, which then can be oxidized to lupanin and, further, to hydroxylupanin. The C skeleton of the quinolizidine alkaloids is derived entirely from lysine. We shall now consider two further groups of alkaloids, the nicotiana alkaloids and the tropane alkaloids, which derive only a part of their C skeleton from the aliphatic amino acids ornithine or lysine. 

One other characteristic of amines is their odor. Low-molecular-weight amines such as trimethyjamine have a distinctive fishlike aroma, while diamines such as 1,5-pentanediamine, commonly called cadaverine, have the appalling odors you might expect from their common names. 

The polyamines putrescine, cadaverine, spermidine, and spermine, which are seen at elevated levels in some victims of cancer, were separated on a Technicon (The Technicon Company Chauncey, NY) TSM Amino Acid Analyzer packed with an 8% divinylbenzene-co-polystyrene sulfonated resin with post-column ninhydrin detection.111 Amines such as ethanolamine, noradrenaline, hexamethylene diamine, methoxytryptamine, spermine, and spermidine were separated from amino acids on a DC-4A cation exchange resin.112 A similar approach, using a Beckman Model 121M amino acid analyzer equipped with an AA-20 column, was also successful.113 A Polyamin-pak strong cation exchange column (JASCO) was eluted with a citrate buffer for the detection of putrescene, spermine, cadaverine, and 1,5-diaminohex-ane from rat thymus.114 A post-column o-phthaldehyde detection system was used. 

Interlaboratory studies were carried out on the precision characteristics of the analytical methods used for determination of certain biogenic amines in fish and fish products, as required by German law. These included putrescine (4a), cadaverine (4b), tyramine (5) and histamine (6)78. 

However, there may be a type of poisoning that does not arise from high levels of histamine, therefore a low histamine level may not be an absolute assurance of product safety. It may be more appropriate to state that the absence of decomposition in the fish renders it a safe product. As such, a safe product would have no evidence of spoilage, including odors of decomposition, high histamine levels, or other amines, e.g. cadaverine. 

The prevalence of biogenic amines in fish depends on several factors. In general, concentrations in newly caught fish are low. Mietz and Karmas (1978) found that cadaverine values ranged from 0.116 to 1.036 mg per 100 g in high-quality rockfish, salmon steaks, and shrimp and that putrescine levels were... 

The predominant amines found in cheese are tyramine, cadaverine, putrescine and histamine (Table 6.6) (Stratton et ah, 1991 Silla Santos, 1996 Novella-Rodriguez et ah, 2002 Novella-Rodriguez et al., 2003). Biogenic amine levels may vary between types of cheese as well as within the varieties themselves. The differences within a variety of cheese may be due to a number of factors, including manufacturing processes, bacterial counts in the milk, heat treatments used, use of starter cultures, and the duration and conditions of the ripening process (Stratton et al., 1991 Pinho et al., 2001 Novella-Rodriguez et al., 2003). 

Biogenic amines are commonly found in fermented meats. Histamine poisoning has not been associated with this type of product, however histamine has been found at low levels in some fermented meats (Dierick et al., 1974 Taylor et al., 1978 Vidal et al., 1990 Shalaby, 1993 Maijala et al., 1993). The most common amine found in fermented meats is tyramine (Trevino et al., 1997 Eerola et al., 1998), which is found at higher concentrations than other amines. The toxic level of biogenic amines is 100 mg per 100 g of product (Arnold et al., 1978). Taylor et al. (1978) and Vandekerckhove (1977) found amounts of histamine up to 55 mg per 100 g, putrescine up to 40 mg per 100 g, cadaverine up to 5.6 mg per 100 g, tyramine up to 151 mg per 100 g, and p-phenylethylamine up to 6.1 mg per 100 g in dry sausage. Table 6.9 lists the... 

However, these experiments were not directed at the oral toxicity of histamine. Taylor and Lieber ( ) showed that rat intestinal HMT and DAO could be inhibited iri vitro by certain amines, including some putrefactive amines that are known to occur in spoiled fish (46.47). Many of these amines inhibited only one of the two histamine-metabolizing enzymes, but several including cadaverine and aminoguanidine were effective inhibitors of both HMT and DAO (45). Mixtures of the inhibitors were not tested, but would be predicted to be quite effective in inhibiting intestinal histamine metabolism. 

Later, Chu and Bjeldanes (53) showed that the binding histamine to mucin could be inhibited in vitro by spermine, spermidine, putrescine, cadaverine, and a basic extract of tuna. The inhibition required relatively high amine concentrations, and the concentrated tuna extract exerted only a 23% inhibition of binding ( ). Each mole of intestinal mucin can bind 2.5 moles of histamine (53). 

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... 

The synthesis of tropine from tropinione requires dehydrogenase NADPH+. Similarly, the synthesis of cocaine requires the Mannich reaction, SAM and NADPH+. Putrescine is a biogenic amine. Other biogenic amines also participate in alkaloid synthesis, for example cadaverine in the case of lysine alkaloids. Aniszewski et al. " drew attention to the fact that the various biogenic amines... 

Alkaloids with the piperidine nucleus, such as pelletierine (Punica grana-tum), lobelanine Lobelia inflata) and piperine Piper nigrum), have a typical biosynthesis pathway. It starts with L-lysine and continues via cadaverine (biogenic amine), A -piperideine and A -piperidinium cations and lobelanine, to be synthesized as lobeline. Piperine is synthesized from A -piperideine via piperidine (Figure 49). For the transformation from A -piperideine to A -piperideine cation, the residue from acetyl-CoA is needed, together with SAM activity in the transformation to lobelanine. Piperine is synthesized from piperidine through the formation of amide. 

The synthesis pathway of quinolizidine alkaloids is based on lysine conversion by enzymatic activity to cadaverine in exactly the same way as in the case of piperidine alkaloids. Certainly, in the relatively rich literature which attempts to explain quinolizidine alkaloid synthesis °, there are different experimental variants of this conversion. According to new experimental data, the conversion is achieved by coenzyme PLP (pyridoxal phosphate) activity, when the lysine is CO2 reduced. From cadeverine, via the activity of the diamine oxidase, Schiff base formation and four minor reactions (Aldol-type reaction, hydrolysis of imine to aldehyde/amine, oxidative reaction and again Schiff base formation), the pathway is divided into two directions. The subway synthesizes (—)-lupinine by two reductive steps, and the main synthesis stream goes via the Schiff base formation and coupling to the compound substrate, from which again the synthetic pathway divides to form (+)-lupanine synthesis and (—)-sparteine synthesis. From (—)-sparteine, the route by conversion to (+)-cytisine synthesis is open (Figure 51). Cytisine is an alkaloid with the pyridone nucleus. 

Piperidine alkaloids contain the piperidine nucleus. The structural development of this group of alkaloids in synthesis is presented in Figure 52. Here a is L-lysine and /3 is cadaverine. The basic ring of j3 is the same as in a, although the activity of PLP reduces carbon dioxide. The j3 is biogenic amine, neither a stable nor a poisonous compound... 

One of the most notable physical properties of many low-formula-mass amines is their offensive odor. Figure 12.16 on page 406 shows two appropriately named amines, putrescine and cadaverine, responsible for the odor of decaying flesh. 

Other BAs, such as putrescine (Put), cadaverine (Cad), tryptamine (Try), /3-phenylethyl-amine (Phe), spermine (Spm), and spermidine (Spd), have been described as potentiators that enhance the toxicity of His (21,22) likewise, Tyr and Phe are thought to precipitate migraine attacks in susceptible subjects (23). 

Fig. 2 Reversed-phase HPLC chromatogram of the dansyl derivatives of amines from a sample of spoiled table olives. Peak identities 1, putrescine 2, cadaverine 3, 1,7-diaminoheptane (IS) 4, tyramine. (From Ref. 19.)...

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