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PubMed1997

Activation of intestinal mitochondrial phospholipase D by polyamines and monoamines.

Intestinal mitochondria have a phospholipase D (PLD) activity which was stimulated by polyamines and monoamines resulting in the formation of phosphatidic acid (PA) from endogenous phospholipids. When stimulated by polyamines, mitochondrial PLD utilized endogenous phosphatidylethanolamine (PE) as substrate whereas stimulated by monoamines, both PE and phosphatidylcholine (PC) were hydrolysed. Stimulation of PA formation by spermine was enhanced by the presence of calcium. Since polyamines are known to alter the calcium transport by mitochondria and PA is known to possess an ionophore effect, stimulation of PA formation in mitochondria by polyamines suggests that polyamine-induced alteration in calcium homeostasis might involve a PA related mechanism.

Animals↗
PubMed1999

Polyamine transport in bacteria and yeast.

The polyamine content of cells is regulated by biosynthesis, degradation and transport. In Escherichia coli, the genes for three different polyamine transport systems have been cloned and characterized. Two uptake systems (putrescine-specific and spermidine-preferential) were ABC transporters, each consisting of a periplasmic substrate-binding protein, two transmembrane proteins and a membrane-associated ATPase. The crystal structures of the substrate-binding proteins (PotD and PotF) have been solved. They consist of two domains with an alternating beta-alpha-beta topology, similar to other periplasmic binding proteins. The polyamine-binding site is in a cleft between the two domains, as determined by crystallography and site-directed mutagenesis. Polyamines are mainly recognized by aspartic acid and glutamic acid residues, which interact with the NH(2)- (or NH-) groups, and by tryptophan and tyrosine residues that have hydrophobic interactions with the methylene groups of polyamines. The precursor of one of the substrate binding proteins, PotD, negatively regulates transcription of the operon for the spermidine-preferential uptake system, thus providing another level of regulation of cellular polyamines. The third transport system, catalysed by PotE, mediates both uptake and excretion of putrescine. Uptake of putrescine is dependent on membrane potential, whereas excretion involves an exchange reaction between putrescine and ornithine. In Saccharomyces cerevisiae, the gene for a polyamine transport protein (TPO1) was identified. The properties of this protein are similar to those of PotE, and TPO1 is located on the vacuolar membrane.

Amino Acid Sequence↗
PubMedDate not supplied

[Brain monoamine oxidase in craniocerebral trauma].

Effect of craniocerebral trauma on monoamine oxidase (MAO) activity was studied. The activity of MAO with monoamines as substrates was shown to decrease. In this case transformation of MAO properties was observed: the enzyme exhibited an ability to deaminate di- and polyamines.

Animals↗
PubMed2003

Effects of human growth hormone (hrGH) treatment on amine metabolism in rats subjected to extensive small bowel resection.

The effect of human recombinant growth hormone (hrGH) on intestinal adaptation in rats subjected to massive small bowel resection has been followed by monitoring changes in the tissue polyamine system and in red blood cell (RBC) polyamine levels. In parallel, the activities of monoamine oxidase A and B and diamine oxidase, the enzymes that catalyse one of the major routes of biogenic amine metabolism, oxidative deamination, were also examined. The results suggest that whilst hrGH treatment accelerates adaptive intestinal hyperplasia evoked by the resection, it has no significant effect on RBC polyamine level or gut mucosal DNA concentration as measured 3 weeks post surgery. hrGH treated operated rats exhibited significantly lower amine oxidase activities which implies that GH may alter biogenic amine systems.

Amines↗
PubMed2004

Coordination mode of adenosine 5'-diphosphate in ternary systems containing Cu(II), Cd(II) or Hg(II) ions and polyamines.

The interactions of adenosine 5'-diphosphate (ADP) with some polyamines (PA) (1,3-diaminopropane (tn), 1,4-diaminobutane (Put), 1,7-diamino-4-azaheptane (3,3-tri) and 1,8-diamino-4-azaoctane (Spd)) both in presence and in the absence of metal ions (Cu(II), Cd(II) and Hg(II)) have been studied. In the metal-free systems the formation of adducts (ADP)Hx(PA) has been observed, in which the main reaction centres are the endocyclic nitrogen atoms of the purine ring, the phosphate group of the nucleotide and the protonated nitrogen atoms of the polyamine. The effectiveness of the phosphate group in formation of adducts has been found to decrease in the series Put > Spd > Spm and to be lower than in the reactions with shorter homologues of biogenic amines. In the ternary systems with metal ions the formation of molecular complexes (ML L' type) has been evidenced in which the protonated polyamine interacts with the nitrogen atoms N(1) or N(7) of the purine ring of the nucleotide. In the ternary systems Cu(II)/ADP/polyamine the coordination dichotomy observed in the binary system Cu(II)/ADP disappears. In the systems with Hg(II) ions the pH range of the dichotomy is extended, while for the systems Cd(II)/ADP/polyamine no changes of the range relative to the binary system Cd(II)/ADP have been noted.

Adenosine Diphosphate↗
PubMed2006

Sequestration of biogenic amines by alginic and fulvic acids.

The interaction of natural (alginic and fulvic acids) and synthetic (polyacrylic acid 2.0 kDa) polyelectrolytes with some protonated polyamines [diamines: ethylendiamine, 1,4-diaminobutane (or putrescine), 1,5-diaminopentane (or cadaverine); triamines: N-(3-aminopropyl)-1,4-diaminobutane (or spermidine), diethylenetriamine; tetramine: N,N'-bis(3-aminopropyl)-1,4-diaminobutane (or spermine); pentamine: tetraethylene-pentamine; hexamine: pentaethylenehexamine] was studied at T=25 degrees C by potentiometry and calorimetry. Measurements were performed without supporting electrolyte, in order to avoid interference, and results were reported at I=0 mol L(-)(1). For all the systems, the formation of (am)L(2)H(i) species was found (am=amine; L=polyelectrolyte; i=1...4, depending on the amine considered). The stability of polyanion-polyammonium cation complexes is always significant, and for high-charged polycations, we observe a stability comparable to that of strong metal complexes. For example, by considering the formation reaction (am)H(i)+2L=(am)L(2)H(i) we found log K(i)=6.0, 6.5 and 10.8 for i=1, 2 and 3, respectively, in the system alginate-spermidine. Low and positive formation DeltaH(degrees) values indicate that the main contribution to the stability is entropic in nature. The sequestering ability of polyelectrolytes toward amines was modelled by a sigmoid Boltzman type equation. Some empirical relationships between stability, charges and DeltaG(degrees) and TDeltaS(degrees) are reported. Mean values per salt bridge of formation thermodynamic parameters (DeltaX(degrees) (n)) are DeltaG(degrees) (n)=-5.8+/-0.4, DeltaH degrees (n)=0.7+/-0.5 and TDeltaS(degrees) (n)=6.5+/-0.5 kJmol(-)(1) for all the systems studied in this work.

Alginates↗
PubMed2000

Highly selective fluorometric determination of polyamines based on intramolecular excimer-forming derivatization with a pyrene-labeling reagent.

We introduce a novel approach in highly selective and sensitive fluorescence derivatization of polyamines. This method is based on an intramolecular excimer-forming fluorescence derivatization with a pyrene reagent, 4-(1-pyrene)butyric acid N-hydroxysuccinimide ester (PSE), followed by reversed-phase high-performance liquid chromatography (HPLC). Polyamines, having two to four amino moieties in a molecule, were converted to the corresponding dipyrene- to tetrapyrene-labeled derivatives by reaction (100 degrees C, 20 min) with PSE. The derivatives afforded intramolecular excimer fluorescence (450-520 nm), which can clearly be discriminated from the monomer (normal) fluorescence (360-420 nm) emitted from PSE, its hydrolysate and monopyrene-labeled derivatives of monoamines. The structures of the derivatives were confirmed by HPLC with mass spectrometry, and the emission of excimer fluorescence could be proved by spectrofluorometry and time-resolved fluorometry. The PSE derivatives of four polyamines [putrescine (Put), cadaverine (Cad), spermidine (Spd), and spermine (Spm)] could be separated by reversed-phase HPLC on a C8 column with linear gradient elution. The detection limits (signal-to-noise ratio of 3) for the polyamines were 1 (Put), 1 (Cad), 5 (Spd), and 8 (Spm) fmol on the column. Furthermore, the present method was so selective that biogenic monoamines gave no peak in the chromatogram.

Chromatography, High Pressure Liquid↗
PubMed2000

Electromigration methods for amino acids, biogenic amines and aromatic amines.

Methods of electromigration in laboratory apparatus of small-bore size have recently undergone development at a remarkably rapid pace, leading to a variety of new analytical techniques. One such technique is called "capillary electrophoresis" (CE), which is further classified on the basis of electromigration mode, viz., "capillary zone electrophoresis" (CZE), which, in turn, has several variations. This review aims to give a short overview of the various electromigration methods for amino compounds by using CE. Firstly, this review briefly summarizes the detection methods employed for detection of monoamines and polyamines by CE for both native and derivative forms. Next, current CE methods are described, and their applications to detection of amino acids, biogenic amines, aromatic amines, including heteroaromatic amines and their enantiomers, are introduced from representative papers. Finally, new methods for single-cell analysis and microchip CE techniques are focused on.

Amines↗
PubMed2004

The effects of lactic acid bacteria inoculants and formic acid on the formation of biogenic amines in grass silages.

Silages were prepared in six laboratory experiments from four direct-cut grassland swards and pure swards of perennial ryegrass and false oat with dry matter contents ranging between 180 and 325 g/kg. Grass was fermented at 22 degrees C and silages were stored at the same temperature for 4 months. Untreated silages (negative control) and silages preserved with 3 g/kg of formic acid (positive control) were compared with silages inoculated with commercial strains of Lactobacillus plantarum, Lactobacillus buchneri and a mixed preparation Microsil. The inoculants were applied at a dose of 5.10(6) CFU/g of grass. Seven biogenic amines were extracted from silages with perchloric acid and determined as N-benzamides by micellar electrokinetic capillary chromatography. Common chemical quality parameters of silages were also determined. Tyramine, cadaverine and putrescine were the amines occurring at the highest concentration. As compared to untreated silages, formic acid was most effective to suppress formation of the main amines. Also the inoculants often decreased amine contents significantly (P < 0.05). The inoculants decreased levels of polyamine spermidine more efficiently than formic acid. Contents of histamine, tryptamine and polyamine spermine were very low, commonly below the detection limits.

Animals↗
PubMed2000

Mixed starter cultures to control biogenic amine production in dry fermented sausages.

Several combinations of an amine-negative Lactobacillus sakei strain, along with proteolytic Staphylococcus carnosus or Staphylococcus xylosus strains, were used to study the influence of mixed starter cultures on biogenic amine production during the manufacture of dry fermented sausages. Changes in pH, water content, proteolysis, microbial counts, and biogenic amine contents were simultaneously examined in a spontaneously fermented batch and in three mixed starter-mediated batches. A double-controlled microbial charge initially inoculated as mixed starter culture of L. sakei and Staphylococcus spp. (all amine-negative strains) drastically reduced tyramine, cadaverine, and putrescine accumulation. No production of other aromatic amines such as histamine, phenylethylamine, or tryptamine was observed in any batch. The polyamines, spermine and spermidine, were found in raw materials and their levels decreased slightly in the spontaneously fermented batch. No correlation between proteolysis and biogenic amine production was observed. The use of proper technological conditions favoring starter development and the use of the raw materials with good hygienic quality make it possible to produce fermented sausages nearly free of biogenic amines.

Animals↗
PubMed1995

Biogenic amines and microbial quality of sprouts.

Changes in the biogenic amine content relative to microbial activities in mung bean, lentil and radish sprouts were investigated in prepacked and "home-grown" products. Biogenic amines were determined by ion-exchange chromatography. The major groups of micro-organisms were enumerated by aerobic plate count procedures, using universal and selective media. Putrescine, cadaverine, spermidine, agmatine and spermine were detected in different concentrations, depending on the type of sprouts. In prepacked retail products the total biogenic amine content was higher than in home-grown samples (mung bean 106 micrograms/g compared to 87 micrograms/g; lentil 316 micrograms/g compared to 181 micrograms/g; radish 1486 micrograms/g compared to 252 micrograms/g). It is concluded that sprouting time and storage conditions play a major part in the hygienic quality of legume sprouts.

Agmatine↗
PubMed1997

Uptake of agmatine into rat brain synaptosomes: possible role of cation channels.

Agmatine (decarboxylated arginine), an endogenous ligand for imidazoline receptors, has been identified in brain where it is synthesized from arginine by arginine decarboxylase. Here we report a mechanism for the transport of agmatine into rat brain synaptosomes. The uptake of agmatine was energy- and temperature-dependent and saturable with a Km of 18.83 +/- 3.31 mM and a Vmax of 4.78 +/- 0.67 nmol/mg of protein/min. Treatment with ouabain (Na+,K+-ATPase inhibitor) or removal of extracellular Na+ did not attenuate the uptake rate. Agmatine transport was not inhibited by amino acids, polyamines, or monoamines, indicating that the uptake is not mediated by any amino acid, polyamine, or monoamine carriers. When we examined the effects of some ion-channel agents on agmatine uptake, only Ca2+-channel blockers inhibited the uptake, whereas a reduction in extracellular Ca2+ increased it. In addition, some imidazoline drugs, such as idazoxan and phentolamine, were strong noncompetitive inhibitors of agmatine uptake. Thus, a selective, Na+-independent uptake system for agmatine exists in brain and may be important in regulating the extracellular concentration of agmatine.

Agmatine↗
PubMed1994

Determination of biogenic amines in leafy vegetables by amino acid analyser.

An automated ion-exchange chromatographic method is described for determination of biogenic amines in leafy vegetables using a cation-exchange resin column in potassium form and a three-buffer system. The following amines were separated and quantified for Chinese cabbage, endive, iceberg lettuce and radiocchio: putrescine, histamine, cadaverine, spermidine, agmatine, spermine, tyramine. Amines from vegetable samples were extracted with 10% trichloroacetic acid. The total concentration of these amines ranged from 14 to 20 micrograms/g fresh weight. Spermidine was the major polyamine detected, present at concentrations of 7-15 micrograms/g fresh weight.

Biogenic Amines↗
PubMed1984

High-performance liquid chromatographic analysis of S-adenosylmethionine and its metabolites in rat tissues: interrelationship with changes in biogenic catechol levels following treatment with L-dopa.

A method is described for the simultaneous analysis of S-adenosylmethionine (SAM) and its metabolites, S-adenosylhomocysteine (SAH) and decarboxylated S-adenosylmethionine along with the natural polyamines, putrescine, spermidine and spermine. The separation is obtained by a reversed-phase ion-pair liquid chromatographic procedure with gradient elution followed by dual detection. The UV absorbance at 254 nm is used for the analysis of SAM and of the SAM metabolites, whereas the polyamines and some major amino acids, e.g., methionine, tyrosine and tryptophan, are analyzed by fluorescence detection after UV-cell derivatization with o-phthalaldehyde. A separate ion-pair reversed-phase high-performance liquid chromatographic (HPLC) procedure using isocratic elution and electrochemical detection is employed to analyse in the same tissue extracts the catechols and 5-hydroxyindoles, 3,4-dihydroxyphenylalanine (DOPA), dopamine, norepinephrine, 3,4-dihydroxyphenylacetic acid, homovanillic acid, 4-hydroxy-3- methoxyphenylalanine , tryptophan, 5-hydroxytryptophan, serotonin and 5- hydroxyindolacetic acid. The sample preparation for the two HPLC procedures requires only homogenization of the tissues in perchloric acid and centrifugation before injection onto the column. The two chromatographic procedures have been applied to study the interrelationship, in various tissues of rats, between the SAM and SAH levels and the biogenic catechols after different treatments with L-DOPA alone or in combination with alpha- monofluoromethyl -DOPA, a potent enzyme-activated irreversible inhibitor of aromatic L-amino acid decarboxylase.

Adrenal Glands↗
PubMed2003

Determination of biogenic amines by capillary electrophoresis with pulsed amperometric detection.

The biogenic amines, putrescine, cadaverine, spermidine and spermine were separated and quantified by capillary electrophoresis with pulsed amperometric detection. Detection potential of the pulsed amperometric detection was optimized as 0.6 V. Optimal separation of the biogenic amines was achieved using a separation buffer of 30 mM citrate at pH 3.5, while keeping the buffer in the detection cell as 20 mM NaOH. Using these conditions, the four biogenic amines were baseline separated. Extrapolated limits of detection for putrescine, cadaverine, spermidine and spermine were 400, 200, 100 and 400 nM for the standard mixture (polyamines dissolved in running buffer), respectively. These are lower than ultraviolet detection and comparable or even lower than laser-induced fluorescence detection results as reported in the literature. The number of theoretical plates was maintained at the 10(5) level, which is absolutely higher than any reported method. When applying capillary electrophoresis-pulsed amperometric detection to milk analysis, only spermidine was found in amounts varying between 0.1 and 0.5 mg/kg.

Animals↗
PubMedDate not supplied

Biogenic amines as regulators of the proliferative activity of normal and neoplastic intestinal epithelial cells (review).

The role of extracellular amines such as noradrenaline and serotonin and their interaction with cyclic nucleotides and intracellular polyamines in the regulation of intestinal epithelial cell proliferation is reviewed with particular reference to the differences between normal and neoplastic cells. In respect to the normal epithelium of the small intestine there is a strong case to support the notion that cell proliferation is controlled by, amongst other things, sympathetic nerves. In colonic carcinomas, antagonists for certain serotonin receptors, for histamine H2 receptors and for dopamine D2 receptors inhibit both cell division and tumour growth. Because of the reproducible variations between tumour lines in the response to these antagonists, this inhibition appears to be due to a direct effect on the tumour cells rather than an indirect effect via the tumour host or stroma. This conclusion is supported by the cytocidal effects of toxic congeners of serotonin on the tumour cells. The most salient difference between the amine responses of normal and neoplastic cells relates to the issue of amine uptake. Proliferation of crypt cells is promoted by amine uptake inhibitors, presumably because they block amine re-uptake by the amine secreting cells--sympathetic neurones and enteroendocrine cells. However, tumour cell proliferation is strongly inhibited by amine uptake inhibitors, suggesting that neoplastic cells can, and need to take up the amine before being stimulated by it. Recent revelations in the field of oncogenes also support an important association between amines, cyclic nucleotides and cell division. The ras oncogenes code for a protein that is a member of a family of molecules which relay information from extracellular regulators, such as biogenic amines, to the intracellular regulators, including cyclic nucleotides. Evidence is presented suggesting that enteroendocrine cells, enterocytes, carcinoid tumour cells and adenocarcinoma cells all have the same embryonic origin and that cells exhibiting an admixture of endocrine and proliferative properties exist in colonic tumours, but not in the normal intestinal epithelium. Thus, it appears that in the normal intestine a clear structural and functional distinction exists between the regulating cells (i.e. the sympathetic neurones and enteroendocrine cells) and the regulated cells (i.e. the undifferentiated crypt cells): cells that have acquired a regulating role are no longer able to divide and cells which are able to divide do not take up or store amines.(ABSTRACT TRUNCATED AT 400 WORDS)

Animals↗