Biogenic amines polyamine

Kalac P., Abreu Gloria M.B. Biogenic amines in cheesess, wines, beers and sauerkraut. In Biological Aspects of Biogenic Amines, Polyamines and Conjugates, Dandrifosse G. (ed.). Transworld Research Network, Kerala, India, pp. 267-309 (2009). 

Primary ( ) amines e.g. alkyl amines [1—3] lipid amines [4] a, co-diamines [5, 6] polyamines [6] alkanol amines [7] subst. anilines [8] aminoglycoside antibiotics [9, 10] biogenic amines [11] hydrazines... 

Novella-Rodriguez, S., Veciana-Nogues, M.T., Izquierdo-Pulido, M. and Vidal-Carou, M.C. (2003). Distribution of biogenic amines and polyamines in cheese, J. Food Sci., 68, 750. 

The venoms of many kinds of bees, wasps, and hornets (the genera Vespa, Polistes, Vespula, Ropalidia, etc.) contain biogenic amines such as histamine (136), serotonin (141), and catecholamines in addition to polyamines such as putrescine (111), spermidine (110), and spermine (112) (Table VIII). The biogenic amines in the venoms act as the main pain-producing principles 46). The contents of these amines in the venom may affect the severity of pain production, edematous reaction of the skin, or increase in skin permeability by stings of these insects. Consequently these amines act as toxins for their defense, together with acetylcholine, enzymes, and peptides 47). 

Amine oxidases catalyze the oxidative deamination of both xenobiotic and biogenic amines, and thus have many critical biological functions. Two distinct classes differ in the nature of their prosthetic groups [1]. The flavin-(FAD flavin adenine dinucleotide)-dependent amine oxidases include monoamine oxidases (MAO A and B) and polyamine oxidases. Amine oxidases not containing FAD, the so-called semicarbazide-sensitive amine oxidases (SSAO), include both plasma amine oxidases and tissue amine oxidases. These contain quinonoid structures as redox cofactors that are derived from posttranslationally modified tyrosine or tryptophan side chains, topaoquinone frequently playing this role [2]. 

Malolactic fermentation is often viewed as the main source of polyamines in wine production (Marcobal et al., 2006). Thus, their presence is more significant in red wines than in white ones. Of white wines, sparkling wines, biologically aged wines, and botrytized wines might be the most susceptible to biogenic amine formation. 

Lavizzari, T. et al. Improved method for determination of biogenic amines and polyamines in vegetable products by ion-pair high-performance liquid chromatography. J. Chromatogr. A. 2006, 1129, 67—72. 

The lack of suitable chromophores for UV-Vis detection can be circumvented by derivatization, and the same strategy can be nsed to obtain the required fluorescence of an analyte if it does not naturally fluoresce. Many flnorophores were investigated and nsed. Determination of leukocyte DNA 6-thioguanine nucleotide levels relied on derivatization with chloroacetaldehyde [25]. A post-column derivatization with )8-naphthoqninone-4-sulfonate allowed the detection of streptomycin and dihydrostreptomycin in foods [26], A post-colnmn derivatization with 0-phthalaldehyde was used for the detection of biogenic amines and polyamines in vegetable products... 

In plants, aliphatic di- and polyamines have been implicated in many processes including rapid cell division, fruit development, stress response and senescence (Evans and Malmberg, 1989 Galston and Kaur-Sawhney, 1995). Amine oxidases catalyse the eatabolism of biogenic amines and hence could be involved in regulating sueh eellular processes. It is eonve-nient to separate discussion of the roles of the copper-containing idiamine... 

Several reports of in vivo and in vitro studies suggest that the absorption, metabolism, and/or potency of one biogenic amine might be modified in the presence of a second amine (Bjeldanes et al., 1978 Taylor and Lieber, 1979 Lyons et al., 1983). Histamine taken in combination with wholesome tuna is reported to yield toxic effects in people even at moderate doses (100-180 mg/100 g tuna) (Motil and Scrimshaw, 1979). Diamines and polyamines inhibit the binding of histamine to mucin, therefore histamine could be released from intestinal mucin and increase the amount of histamine... 

A much more general application of OPA was introduced when Roth [275] showed that nearly all amino acids can form fluorescent condensation products in the presence of an alkylthiol, such as 2-mercaptoethanol. Continuous reaction of the column effluent with OPA/ 2-mercaptoethanol or other thiol at pH 10, followed by recording of fluorescence intensity (excitation at 340-345 nm, emission at 455 nm), became a very widely used method for the determination of amino acids [276-298], peptides [280,291, 294—299], biogenic amines and polyamines [300-317], antibiotics [318-323] carbamates [324] and other primary amino group-containing compounds. OPA/R-SH reagents have to a considerable extent replaced ninhydrin for post-column derivative formation. 

Bover-Cid, S., Izquierdo-Pulido, M., Vidal-Carou, M. C. (2001). Changes in biogenic amine and polyamine contents in slightly fermented sausages manufactured with and without sugar. Meat Science, 57, 215-221. http //dx.doi.org/10.1016/S0309-1740(00)00096-6. 

Komprda, T., Rejchrtova, E., Slddkova, R, Zemanek, L., VymlatUova, L. (2012). Effect of some external factors on the content of biogenic amines and polyamines in a smear-ripened cheese. Dairy Science Technology, 92, 367-382. 

Most spider neurotoxins characterized to date have been found to be low molecular weight organic molecules (inorganic ions and salts, free acids and ami-noacids, biogenic amines, neurotransmitters, and acylpolyamines), peptides, or proteins. Polyamines and a variety of polypeptides with a molecular mass ranging from 3000 to 8000 Da appear to represent the main toxic compounds in spiders. More than 60 peptide toxins have been described to date, whose presence can be confirmed by reversed-phase LC. Peptides can be easily distinguished from polyamines because of their different retention times and by ultraviolet detection using a diode-array detector. 

Biogenic amines, biological amines biologically and pharmacologically important naturally occurring amines, occurring widely in plants and animals. They can be divided into 1. derivatives of ethanolamine, e.g. choline, acetylcholine, muscarine 2. polymethylene diamines, e.g. putrescine, cadaverine 3.polyamines, e.g. spermine 4. imidazolylalkylamines, e.g. histamine 5.phenylalkylamines, e.g. mescaline, tyra-mine, hordenine 6. catecholamines, e. g. adrenalin, nor-adrenalin and dopamine 7. indolylalkylamines, e.g. tryptamine, serotonin and 8. betaines, e.g. carnitine. 

In contrast to the harmful biogenic amines, the polyamines putrescene, spermidine and spermine are necessary for optimal growth and function of cells. They are involved in DNA, RNA and protein synthesis, regulation of gene expression, enzyme activity, cell proliferation and cell signaUtng. 

The first successful polyamine separations were accomplished in the mid-1970s with the introduction of surface-sulfonated cation exchangers. The separation of biogenic amins such as putrescine (1,4-diaminobutane), cadaverine (1,5-diaminopentane), spermidine (Al-(3-aminopropyl-l,4-diaminobutane), and spermine (Al,Al -bis-(3-aminopropyl)-l,4-diaminobutane) took more than 30 min. The required eluent comprised three buffer solutions that differed both in pH and in the trisodium citrate and sodium chloride concentration. Owing to the high ionic strength of these buffer solutions, detection could not be carried out by means of suppressed conductivity measurements. However, polyamines carry terminal NH2 groups and thus, fluorescence detection after reaction with... 

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