Amines putrescine

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. 

Draisci et al. [7] Biogenic amines putrescine, cadaverine, histamine, tyramine, spermidine, spermine, tryptamine Anchovies Diamine oxidase (DAO)/on a nylon-net membrane, using glutaraldehyde Platinum electrode/ +0.650V vs. Ag/AgCl ... 

Amines are the particular products of putrefaction. None of the AF tested utilized amines (putrescine, ethylenediamine) as the sole source of nitrogen in culture (Table 4.1), although some amines (ethylenediamine, trimethyl-amine) are as effective as urea in the field (Sagara 1975,1992). This would show that AF do not directly utilize amines but utilize them only after decomposition to ammonia. Thus, the word postputrefaction in the term PPF may seem inappropriate from the fungal physiological point of view (Yamanaka 2002), but this word indicates the characteristic feature of cadaver and fecal decomposition. It also describes the major cause for growth of the AF in nature. 

Pyrrolidine may be synthesized from tetra-methylene di-amine, putrescine (p. 194), by the loss of ammonia. 

Specific decarboxylases are known for a majority of the amino acids, and several are prime targets for inactivation by virtue of their substantial medicinal importance. These include aromatic-amino-acid decarboxylase, which is responsible for the production of dopamine (DOPA) orithine decarboxylase, which supplies the p amine putrescine and glutamate decarboxylase, which converts glutamate to the inhibitory neurotransmitter y-aminobutyric acid (GABA). The accepted mechanism of these enzymes involves decarboxylation of the amino acid to yield a resonance-stabilized carbanion at the a-carbon of the substrate. The intermediate is then protonated with retention of configuration to yield product (Walsh, 1979, p. 800). 

This pathway which is widely distributed in bacteria, acts as an energy source under anaerobic conditions, and produces a marked pH-rise effect due to the production of NH3. It is induced by arginine supplementation. It also acts as a source of ornithine which can subsequently be decarboxylated, particularly at low pH values, to produce an increase in the pH (page 508) and the evil-smelling amine putrescine which occurs in decaying meat. 

These microorganisms generate a wide array of compounds that contribute to whole fish spoilage and produce many off-odor and off-flavor compounds such as biogenic amines (putrescine, cadaverine, and histamine), hydroxylamine, ketones, aldehydes, alcohols, and organic acids that are essentially absent or only occur at very low levels in fresh fish (Ghaly et al., 2010). 

The poly amines putrescine (butane-1,4-diamine), spermidine [N-(3-aminopropyl)butane-1,4-diamine] and spermine [N,N -bis-(3-aminopropyl)-... 

The amines putrescine and cadaverine are poisonous compounds formed when amino acids are degraded in the body. Because these amines are excreted as quickly as possible, their odors may be detected in the urine and breath. Putrescine and cadaverine are also responsible for the odor of decaying flesh. 

Hi) Poly amines. In many respects the role of poly amines in plant functioning is still mysterious after many years work. They are almost certainly involved in the control of growth and development through their interactions with nucleic acids and membranes (Smith, 1985). There is increasing circumstantial evidence for their involvement, especially of putrescine, in plant responses to a wide range of stresses including pH, Mg deficiency, osmotic shock, cold, SO2 pollution, and cadmium and ammonium toxicity (Smith, 1985). It remains to be determined, however, how, and indeed whether, putrescine accumulation in response to these diverse stresses is beneficial. 

Species of Pseudomonas can utilize the a,(i)-diamines putrescine, spermidine, and spermine as sources of carbon and nitrogen, and putrescine can be produced from the secondary amine spermidine together with 1,3-diaminopropane (Dasu et al. 2006). Putrescine (1,4-diaminobutane) is an intermediate in the arginine decarboxylase (ADC) pathway of L-arginine degradation, which is described later, and can be degraded, by two pathways ... 

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. 

At physiological pH, polyamines are fully protonated and polycationic. It is possible that the amino group of amines prevents SAM from reacting with ACS by interfering with the prosthetic groups of the enzyme. Polyamines such as putrescine, spermidine, and spermine, and methionine cycle intermediates such as MTA and KMB have been shown to have an inhibitory effect on ACS activity. ... 

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... 

Ansorena et al. (2002) also found that this change in pH leads to a decrease in the amounts of histamine and putrescine produced. Use of acidulants, such as glucono 8-lactone, may influence amine production by ensuring a drop in pH (Santos et al., 1986 Buncic et al., 1993 Maijala et al., 1993). A gradual increase in pH throughout the ripening process is related to the proteolytic activity of the starter culture as it forms peptides and amino acids (Bover-Cid et al., 1999). 

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