BIOGENIC AMINES, BIOGENIC ALDEHYDES, AND ALCOHOL.
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Biogenic amines like dopamine or octopamine modify neural function at multiple levels, sensitizing or depressing behaviour. Recent studies in insects have now shown that, besides a role in motivational modulation, biogenic amines substitute the reinforcer function in associative learning, thus instructing the nervous system about the relevance of external events.
Biogenic amines, with a primary amino group, were reacted with glutaraldehyde to form insoluble precipitates. These precipitates had distinctive ultrastructural features upon further reaction with osmic acid. When tested in vitro, they had biological activity and showed evidence that part of this biological activity was due to the large polymer of glutaraldehyde and amine. Experiments with isotope-labelled amines in the production of these precipitates showed that the precipitated polymers were not completely stable and that free amine was liberated from them. Since they were not stable, , they could not be used for the morphological localization of the amines as had been intended, but they may have some use as depot drugs or in the immunization of animals against these amines.
Biogenic amines were found to inhibit the transfer of 3H-labelled methyl groups from S-adenosyl methionine to histamine by rat kidney histamine methyl transferase, the most potent being tyramine, tryptamine and their hydroxyl derivatives. There appeared to be no competition between histamine and other amines for methyl groups since methyl histamine was the only methylation product formed. The inhibition could not be explained by the formation of stable complexes between inhibitor and the methyl transferase. It is recommended that histamine determinations on biologic specimens by the radioenzymatic assay include a control with added authentic histamine.
Capillary electrophoresis was coupled successfully and reliably to potentiometric sensors, which are based on an ionically conductive rubber phase coating, applied on a 250 microm diameter metal substrate. The membrane components included potassium tetrakis(p-chlorophenyl)borate (TCPB), bis(2-ethylhexyl)sebacate (DOS), and high molecular mass poly(vinyl chloride) (PVC). Potentiometry reveals a very sensitive CE detection mode, with sub-micromolar detection limits for amines and the randomly chosen drugs quinine, clozapine, cocaine, heroine, noscapine, papaverine, and ritodrine. The lowest detection limit, 1 x 10(-8) M injected concentration, was obtained for the quaternary ammonium compound tetrahexylammonium chloride. The more polar lower aliphatic amines and the biogenic amines dopamine, adrenaline, and cadaverine have much higher detection limits. The detection limits are log P dependent. Addition of a commercially available calixarene molecule or a synthetic macrocyclic amphiphilic receptor molecule to the electrode coatings enhanced the sensitivity respectively for the lower aliphatic amines and for the biogenic amines. A transpose of the Nikolskii-Eisenman-type function was suggested and used to convert the signal of the detector to a concentration-dependent signal.
In laboratory silages made from orchardgrass, red clover and oats, significant levels of toxic biogenic amines were found. The most widespread were putrescine and cadaverine, concentrations of spermidine, spermine and histamine were ten times lower on average. Of the amines considered, putrescine content seems to be the most sensitive indicator of the extent of putrefaction in silages. A relationship between the putrescine contents and the degree of proteolysis was found. The biogenic amine content is closely connected with both the variety of crop ensiled and even more so with the method and the efficiency of preservation. Neither the application of formic acid nor wilting suppressed the formation of any of the amines in silages selectively. Formic acid suppressed the total concentration of amines to 23% as compared with controls. The highest levels of amines were found in orchardgrass and oat silages; smaller amounts were detected in clover silages. In the case of very poorly preserved silage 100-150 g of toxic amines can be consumed by a cow in a day. This could have a deleterious effect on the physiological condition and the performance of livestock.
A 4 x 4 Latin square experiment was conducted to examine abomasal passage of biogenic amines in steers fed silage and their related effects on intake, digestibility, and digestive function. Thirty percent of the dry matter (DM) in the diets consisted of alfalfa forage, which was fed as either hay or silage. The DM from alfalfa silage DM was substituted at 0, 33, 67, and 100% for DM from alfalfa hay and was fed to four ruminally and abomasally cannulated steers. The roughage component of the diet constituted 50% of the DM and consisted of 60% alfalfa silage or hay and 40% tropical corn silage. The concentrate was composed mainly of ground corn. The concentrations of putrescine and cadaverine in abomasal digesta increased as alfalfa silage in the diet increased. Abomasal recovery of biogenic amines, a product of their concentration in abomasal digesta and the passage of DM through the abomasum, was negatively correlated with intake. Abomasal recovery of most amines was 5 to 20% of intake. Abomasal recovery of cadaverine was correlated with depressed intake. Total DM intake was reduced 8.3 to 25.8% as the proportion of alfalfa silage in the diet increased. Frequency of reticular contractions, intake, ruminal DM digestibility, ruminal outflow, volatile fatty acids, and total tract DM digestibility decreased in steers fed diets that contained more alfalfa silage. Ruminal fluid pH and NH3 concentration increased in steers fed more alfalfa silage; however, mass and the DM percentage of ruminal contents decreased linearly. Postprandial insulin concentrations were quadratically related to the proportion of alfalfa hay or silage in the diet. Intraruminal metabolism of biogenic amines is extensive based on the relatively low quantities recovered in abomasal digesta; however, the amounts recovered in abomasal digesta were related to intake depression and associated physiological effects.
Biogenic amine transport systems in the presynaptic plasma membrane and the synaptic vesicle provide a mechanism for rapidly terminating the action of released transmitters and for recycling neurotransmitters. Alterations in the activity of these transporters, either by endogenous regulatory mechanisms or by drugs, affect the regulation of synaptic transmitter levels. For drugs such as antidepressants and stimulants that interact with these transport systems, the therapeutic and behavioral consequences are profound. Now that the cDNAs encoding the transporters have been isolated, we can expect rapid progress in understanding how the individual proteins work at the molecular level to couple ion gradients to the reuptake and storage of biogenic amine neurotransmitters.
When analysing a series of laboratory silages made from orchardgrass, red clover and oats, the fluctuating dynamics of biogenic amines were observed. For levels of putrescine and cadaverine, a rapid exponential increase culminating approximately 30-50 days after ensiling is typical. A small decrease, reaching the minimum at approximately the 100th day, is sometimes followed by a second increase in amine concentrations achieving its maximum approximately 200-230 days after ensiling. Irregular curves of the dynamics probably originate in the simultaneous decarboxylation and deamination reactions along with other relevant amine degradation processes. The dynamics of other biogenic amines-spermidine, spermine and histamine are more difficult to predict. The changes in histamine levels resembled those in the diamines. Some 200 days after ensiling, considerable increases in this toxic amine were observed. The dynamics of some quality criteria, especially the degree of proteolysis, were in many cases similar to those of the amines.
The biogenic amines tryptamine, 5-hydroxytryptamine, tyramine and histamine were assessed for their abilities to modify the genotoxicity of the cooked-food mutagens IQ, MeIQ, MeIQx, Trp-P-1 and Trp-P-2. These measurements were made using a bacterial mutation assay with hepatic fractions from either SWR mice or DSN Syrian hamsters as the activating system and Salmonella typhimurium TA98 as the indicator organism. Although histamine had very little effect on the genotoxicity of these mutagens, the other amines reduced genotoxicity, with tryptamine and 5-hydroxytryptamine exerting the greatest effect. Generally the amines exhibited greater potency when S-9 fractions from mice rather than from hamsters were used.
Concentrations of putrescine (PUT), cadaverine (CAD), spermidine (SPD), spermine (SPM), histamine (HIS) and tyramine (TYR) in 53 grass silages and 54 maize silages were determined using an HPLC method. Concentrations of all amines excluding SPD in grass silages decreased significantly with increasing dry matter (DM) contents and decreasing acetic acid concentrations. The mean concentrations were 1310, 642, 414, 139, 120 and 33.6 mg/kg for TYR, CAD, PUT, SPM, HIS and SPD respectively in grass silages of 20-30% DM. The maximal values found were twice to five times higher than the mean values. The effect of increasing DM on the amines concentrations was not evident in maize silages. The mean concentrations, regardless of the DM content, were surprisingly high: 435, 388, 341, 71.7, 25.1 and 5.4 mg/kg for TYR, PUT, CAD, HIS, SPD and SPM. The maximal values in maize silages were three times to ten times higher than the mean values. Considering that maize silage forms the great proportion of the diets of cattle during long-term winter feeding, further toxicological and physiological research should be carried out.
Studies on the uptake and storage of sodium and biogenic amines (phenylethylamine, noradrenaline, histamine) by two weak cation-exchangers, IRC-50 and Sephadex C-50, and by biogenic granule-enriched preparations demonstrated that the synthetic and biogenic materials had several common characteristics. They showed similar concentration- and pH-dependence and fitted the same cation-exchange and receptor-binding equations. The observations were taken to support the view that the matrices of amine-storing granules have the properties of weak cation-exchangers, with carboxyls as the cation-binding groups.
This study evaluated the formation of biogenic amines (BAs) in breast chicken meat during storage under aerobic and modified atmospheric packaging (MAP) conditions at 4 degrees C, the correlation of microbial and sensory changes in chicken meat with formation of BAs and the possible role of BAs as indicators of poultry meat spoilage. Poultry breast fillets were stored aerobically or under MAP (30%, CO(2), 70% N(2)) at 4 degrees C for up to 17 days. Quality evaluation was carried out using microbiological, chemical and sensory analyses. Total viable counts, Pseudomonads and Enterobacteriaceae, were in general higher for chicken samples packaged in air whereas lactic acid bacteria (LAB) and Enterobacteriaceae were among the dominant species for samples under MAP. Levels of putrescine and cadaverine increased linearly with storage time and were higher in aerobically stored chicken samples. Spermine and spermidine levels were also detected in both aerobically and MAP stored chicken meat. Levels of tyramine in both chicken samples stored aerobically and or under MAP were low (< 10 mg kg(-1)) whereas the formation of histamine was only observed after day 11 of storage when Enterobacteriaceae had reached a population of ca. 10(7) CFU g(-1). Based on sensory and microbiological analyses and also taking into account a biogenic amines index (BAI, sum of putrescine, cadaverine and tyramine), BAI values between 96 and 101 mg kg(-1) may be proposed as a quality index of MAP and aerobically-packaged fresh chicken meat. Spermine and spermidine decreased steadily throughout the entire storage period of chicken meat under aerobic and MAP packaging, and thus these two amines cannot be used as indicators of fresh chicken meat quality.
Biogenic amines are organic bases with low molecular weight. They can be expected in all foods that contain proteins or free amino acids. Consumption of food containing high amounts of biogenic amines may cause toxicological effects. The most notorious foodborne intoxications caused by biogenic amines are related to histamine. The article reviewed methods of determination of biogenic amines in foods in recently years and emphasized on the characteristics of HPLC, CE, biosensor and TLC and their applications.
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Superfusion of phenylethylamine-, noradrenaline- or histamine-charged weak (carboxyl) cation-exchangers (IRC-50 and Duolite CS-100) with isotonic NaCl caused a release of the amines. Similarly, bovine chromaffin granules and nerve granule preparations from bovine splenic nerve, rat vas deferens and rat corpus striatum released their amine(s) upon superfusion with the same solution. The courses of release from the synthetic and biogenic materials showed very similar characteristics and fitted the same exchange equations. The observations support the view that the matrices of the biogenic amine-storing granules have the properties of weak cation-exchanger materials with carboxyls as the cation-binding groups, and that the NaCl-induced release of the biogenic amines is due to cation exchange (Na+ in equilibrium Amine+). The possibility that amine release in vivo is based on cation exchange is discussed.
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Biogenic amines in spoiled animal by-product feeds have been implicated in causing poor performance and intestinal lesions in broilers. This study was designed to determine if biogenic amines, at the concentrations found in animal by-product meals, would reduce performance in broilers or cause lesions. Twelve treatments were used in a 2 x 6 factorial arrangement with the main effects being either a corn-soybean meal diet or a corn-soybean meal diet with 10% animal by-products added and either no amines added or added levels of phenylethylamine (4.8 mg/kg), putrescine (49 mg/kg), cadaverine (107 mg/kg), histamine (131 mg/kg), or a combination of all these amines. Levels of biogenic amines used in this study simulated those found in areas with reported problems attributed to biogenic amines. Broilers were monitored for performance, gross lesions, and histologic evidence of lesions at 2, 4, and 6 wk. No consistent effects were observed on performance, and by the conclusion of the trial, no statistical differences were noted in the performance of any of the treatments. No gross lesions were observed on a consistent basis in any of the treatments. Histopathology was likewise unremarkable. On the basis of this study, it would appear that these four biogenic amines, at levels detected in the United States, do not pose a serious health concern for the broiler industry.