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Zeitschrift Fur... Jul 1995A total of 523 strains representing 35 species related to food fermentation organisms of practical importance were investigated for their potential for formation of... (Comparative Study)
Comparative Study
A total of 523 strains representing 35 species related to food fermentation organisms of practical importance were investigated for their potential for formation of biogenic amines (BA). The investigation was performed with resting cells in phosphate buffer (pH 5.5) and the formation of the following BAs was followed: putrescine, cadaverine, histamine, tyramine and 2-phenylethylamine. No potential was observed in species of lactococcus, Leuconostoc, Pediococcus, Streptococcus and several Lactobacillus spp., such as L. Pentosus and L. sake. A remarkable potential to form BA was observed in strains of carnobacteria, Lactobacillus buchneri, L. curvatus, L. reuteri, Staphylococcus carnosus and, to a lesser extent, in L. alimentarius, L. brevis, L. bavaricus, L. delbrueckii ssp. lactis, Micrococcus spp. and S. piscifermentans. In well known species with a practical function in the fermentation of dairy products, wine or cabbage a potential was observed for few strains only. In view of their role as starters in food fermentation, or their potential use in protective cultures and as probiotics, BA formation by the organisms has to be taken into consideration by selecting appropriate strains.
Topics: Bacteria; Biogenic Amines; Cadaverine; Fermentation; Histamine; Phenethylamines; Putrescine; Species Specificity; Tyramine
PubMed: 7571871
DOI: 10.1007/BF01193205 -
Drug and Chemical Toxicology Jul 2020Phenylethylamine's acute toxic effects in a population of adult (10 to 12 weeks old; ∼30 g) Swiss male albino mice are significantly increased by para-position...
Phenylethylamine's acute toxic effects in a population of adult (10 to 12 weeks old; ∼30 g) Swiss male albino mice are significantly increased by para-position aromatic ring halogenation. LD, LD, and LD values (mg/kg; x ± SEM) for p-F- (116.7 ± 3.3, 136.7 ± 1.7, and 160.0 ± 2.9), p-Br- (126.7 ± 3.3, 145.0 ± 2.9, and 163.3 ± 3.3), p-Cl- (133.3 ± 3.3, 146.7 ± 1.7, and 165.0 ± 2.9), and p-I-PEA (133.3 ± 3.3, 153.3 ± 1.7, and 168.3 ± 1.7), compared to PEA 203.3 ± 3.3, 226.7 ± 4.4, and 258.3 ± 8.8). Like PEA, the difference between LD and LD, and LD and LD for individual amines were similar and in the range (10 to 20%). Toxicity variation between the various p-halogenatedPEAs also fell within a relatively narrow range (as a group: LD 116.7 ± 3.3 to 133.3 ± 3.3, LD 136.7 ± 1.7 to 153.3 ± 1.7, and LD 160.0 ± 2.9 to 168.3 ± 1.7 mg/kg). PEA methylation, (exception of its α-methyl derivative), results in relatively modest changes in acute toxicity. LD, LD, and LD values (mg/kg; x ± SEM) for N-Me- (176.6 ± 3.3, 200.0 ± 2.9, and 221.7 ± 3.3), p-Me- (183.3 ± 3.3, 206.7 ± 3.3, and 225.0 ± 2.9), o-Me- (210.0 ± 5.8, 233.3 ± 3.3, and 258.3 ± 1.7), and β-MePEA (220.0 ± 5.8, 243.3 ± 4.4, and 278.3 ± 44). Similar to PEA, and the p-HPEAs, the difference between LD and LD and LD and LD values for individual amines fell within a relatively narrow range (10 to 20%). Variation in toxicity among the methylatedPEAs also fell within a limited range (as a group: LD 176 ± 3.3 to 220 ± 5.8, LD 200.0 ± 2.9 to 243.3 ± 4.4 and LD 221.7 ± 3.3 to 278.3 ± 4.4 mg/kg). With the exception of PEA's methyl derivative (amphetamine) all the amines studied are rapidly metabolized by monoamine oxidase. This pharmacokinetics difference would help to explain the markedly higher amphetamine toxicity [(LD, LD and LD (mg/kg; x ± SEM) of 21.3 ± 0.9, 25.0 ± 0.6, and 29.3 ± 0.7, respectively)].
Topics: Animals; Lethal Dose 50; Male; Mice; Phenethylamines; Toxicity Tests, Acute
PubMed: 30614291
DOI: 10.1080/01480545.2018.1551899 -
Science (New York, N.Y.) Jun 1983The compound 2-phenylethylamine is an "endogenous amphetamine" which may modulate central adrenergic functions. 2-Phenylethylamine is mainly metabolized by monoamine...
The compound 2-phenylethylamine is an "endogenous amphetamine" which may modulate central adrenergic functions. 2-Phenylethylamine is mainly metabolized by monoamine oxidase to form phenyl acetate (PAA). The 24-hour urinary excretion of PAA was measured in normal healthy volunteers and depressed patients. Patients were diagnosed according to the Diagnostic and Statistical Manual of Mental Disorders, edition 3. In 70 percent of healthy volunteers of both sexes, the excretion of PAA ranged between 70 and 175 milligrams per 24 hours (mean = 141.1 +/- 10.2). Inpatients with major depressive disorder (unipolar type) (N = 31) excreted less PAA (68.7 +/- 7.0 milligrams per 24 hours) and 55 percent of them excreted less than 70 milligrams per 24 hours; there were no significant differences in the PAA excretion between untreated patients (N = 13) and those treated with antidepressants that were not effective (N = 18). The PAA excretion was reduced to a lesser extent in 35 less severely depressed unipolar outpatients (drug-free for 1 week) (86.3 +/- 11.8 milligrams per 24 hours). These results suggest that low PAA urinary excretion may be a reliable state marker for the diagnosis of some forms of unipolar major depressive disorders.
Topics: Adolescent; Adult; Aged; Antidepressive Agents; Depressive Disorder; Female; Humans; Male; Middle Aged; Phenethylamines; Phenylacetates
PubMed: 6857245
DOI: 10.1126/science.6857245 -
Journal of Bacteriology Aug 2019Aromatic amines like 2-phenylethylamine (2-PEA) and benzylamine (BAm) have been identified as novel growth substrates of the betaproteobacterium EbN1, which degrades a...
Aromatic amines like 2-phenylethylamine (2-PEA) and benzylamine (BAm) have been identified as novel growth substrates of the betaproteobacterium EbN1, which degrades a wide variety of aromatic compounds in the absence of oxygen under denitrifying growth conditions. The catabolic pathway of these amines was identified, starting with their oxidative deamination to the corresponding aldehydes, which are then further degraded via the enzymes of the phenylalanine or benzyl alcohol metabolic pathways. Two different periplasmic quinohemoprotein amine dehydrogenases involved in 2-PEA or BAm metabolism were identified and characterized. Both enzymes consist of three subunits, contain two heme cofactors in their α-subunits, and exhibit extensive processing of their γ-subunits, generating four intramolecular thioether bonds and a cysteine tryptophylquinone (CTQ) cofactor. One of the enzymes was present in cells grown with 2-PEA or other substrates, showed an αβγ composition, and had a rather broad substrate spectrum, which included 2-PEA, BAm, tyramine, and 1-butylamine. In contrast, the other enzyme was specifically induced in BAm-grown cells, showing an αβγ composition and activity only with BAm and 2-PEA. Since the former enzyme showed the highest catalytic efficiency with 2-PEA and the latter with BAm, they were designated 2-PEADH and benzylamine dehydrogenase (BAmDH). The catalytic properties and inhibition patterns of 2-PEADH and BAmDH showed considerable differences and were compared to previously characterized quinohemoproteins of the same enzyme family. The known substrate spectrum of EbN1 is expanded toward aromatic amines, which are metabolized as sole substrates coupled to denitrification. The characterization of the two quinohemoprotein isoenzymes involved in degrading either 2-PEA or BAm expands the knowledge of this enzyme family and establishes for the first time that the necessary maturation of their quinoid CTQ cofactors does not require the presence of molecular oxygen. Moreover, the study revealed a highly interesting regulatory phenomenon, suggesting that growth with BAm leads to a complete replacement of 2-PEADH by BAmDH, which has considerably different catalytic and inhibition properties.
Topics: Anaerobiosis; Bacterial Proteins; Benzylamines; Oxidoreductases Acting on CH-NH Group Donors; Phenethylamines; Rhodocyclaceae
PubMed: 31138631
DOI: 10.1128/JB.00281-19 -
Efficacy of β-phenylethylamine as a novel anti-microbial and application as a liquid catheter flush.Journal of Medical Microbiology Dec 2018With this study, we introduce a liquid flush for catheters and other tubing-based applications that consists of a solution of β-phenylethylamine (PEA) in tryptic soy...
With this study, we introduce a liquid flush for catheters and other tubing-based applications that consists of a solution of β-phenylethylamine (PEA) in tryptic soy broth. The initial experiments in multiwell polystyrene plates were conducted with Escherichia coli K-12 to assess the effectiveness of PEA at reducing planktonic growth, as well as the biomass and adenosine triphosphate (ATP) content of biofilm; PEA reduced these growth parameters as a function of increasing concentration. This effect was also seen in mutants of PEA catabolism, which leads us to believe that the PEA effect is due to PEA itself and not one of its degradation products. Since PEA reduced planktonic growth and biofilm when added at the time of inoculation, as well as at later time points, we propose PEA as a novel compound for the prevention and treatment of biofilm. PEA reduced planktonic growth and the ATP content of the biofilm for five bacterial pathogens, including an enterohemorrhagic E. coli, two uropathogenic E. coli, Pseudomonas aeruginosa and Staphylococcus aureus. A major finding of this study is the reduction of the ATP content of biofilm that formed in silicone tubing by periodic flushes of PEA. This experiment was performed to model antibiotic-lock treatment of an intravenous catheter. It was found that 10 mg ml of PEA reduced the ATP content of biofilm of five bacterial strains by 96.3 % or more after 2 weeks of incubation and three treatments with PEA. For P. aeruginosa, the reduction in ATP content was paralleled by an identical percentage reduction in viable cells in the biofilm.
Topics: Adenosine Triphosphate; Bacteria; Biofilms; Catheter-Related Infections; Catheters, Indwelling; Escherichia coli K12; Mutation; Phenethylamines; Polystyrenes; Silicones; Surface Properties
PubMed: 30325301
DOI: 10.1099/jmm.0.000840 -
Determinants involved in subtype-specific functions of rat trace amine-associated receptors 1 and 4.British Journal of Pharmacology Mar 2013The trace amine-associated receptor (Taar) family displays high species- and subtype-specific pharmacology. Several trace amines such as β-phenylethylamine (β-PEA),...
AIMS
The trace amine-associated receptor (Taar) family displays high species- and subtype-specific pharmacology. Several trace amines such as β-phenylethylamine (β-PEA), p-tyramine and tryptamine are agonists at TA(1) but poorly activate rat and mouse Taar4.
PRINCIPAL RESULTS
Using rat TA(1) and Taar4 chimera, we identified determinants in transmembrane helices 3 and 6, which, when replaced by the corresponding portion of rat TA(1) , can rescue cell surface expression of rat Taar4. When expressed at the cell surface, rat Taar4 pharmacology was very similar to that of TA(1) and coupled to the Gα(s) -protein/AC pathway. Our data suggest that binding pockets of Taar for surrogate agonists overlap between paralogs.
CONCLUSIONS
This implicates that the repertoire of Taar ensures functional redundancy, tissue- and cell-specific expression and/or different downstream signalling rather than different agonist specificity.
Topics: Animals; COS Cells; Cell Membrane; Chlorocebus aethiops; HEK293 Cells; Humans; Phenethylamines; Protein Transport; Rats; Receptors, G-Protein-Coupled; Tryptamines; Tyramine
PubMed: 23072560
DOI: 10.1111/bph.12020 -
Drug Testing and Analysis Feb 2017This paper reports analytical properties of five substituted phenethylamine derivatives seized from a clandestine laboratory. These five derivatives include...
This paper reports analytical properties of five substituted phenethylamine derivatives seized from a clandestine laboratory. These five derivatives include 5-(2-methylaminopropyl)-2,3-dihydrobenzofuran (5-MAPDB, 1), 5-(2-aminoethyl)-2,3-dihydrobenzofuran (5-AEDB, 2), N,2-dimethyl-3-(3,4-methylenedioxyphenyl)propan-1-amine (MDMA methylene homolog, 3), 6-bromo-3,4-methylenedioxymethamphetamine (6-Br-MDMA, 4), and 1-(benzofuran-5-yl)-N-(2-methoxybenzyl)propan-2-amine (5-APB-NBOMe, 5). These compounds were identified by liquid chromatography-quadrupole time-of-flight mass spectrometry (LC-QTOF-MS), gas chromatography-mass spectrometry (GC-MS), and nuclear magnetic resonance spectroscopy (NMR). No analytical properties about compounds 1-4 have appeared until now, making this the first report on these compounds. Copyright © 2016 John Wiley & Sons, Ltd.
Topics: Designer Drugs; Gas Chromatography-Mass Spectrometry; Magnetic Resonance Spectroscopy; Mass Spectrometry; N-Methyl-3,4-methylenedioxyamphetamine; Phenethylamines; Psychotropic Drugs
PubMed: 26856255
DOI: 10.1002/dta.1955 -
Analytica Chimica Acta Jun 2014A new procedure for determination of biogenic amines (BA): histamine, phenethylamine, tyramine and tryptamine, based on the derivatization reaction with...
A new procedure for determination of biogenic amines (BA): histamine, phenethylamine, tyramine and tryptamine, based on the derivatization reaction with 2-chloro-1,3-dinitro-5-(trifluoromethyl)-benzene (CNBF), is proposed. The amines derivatives with CNBF were isolated and characterized by X-ray crystallography and (1)H, (13)C, (19)F NMR spectroscopy in solution. The novelty of the procedure is based on the pure and well-characterized products of the amines derivatization reaction. The method was applied for the simultaneous analysis of the above mentioned biogenic amines in wine samples by the reversed phase-high performance liquid chromatography. The procedure revealed correlation coefficients (R(2)) between 0.9997 and 0.9999, and linear range: 0.10-9.00 mg L(-1) (histamine); 0.10-9.36 mg L(-1) (tyramine); 0.09-8.64 mg L(-1) (tryptamine) and 0.10-8.64 mg L(-1) (phenethylamine), whereas accuracy was 97%-102% (recovery test). Detection limit of biogenic amines in wine samples was 0.02-0.03 mg L(-1), whereas quantification limit ranged 0.05-0.10 mg L(-1). The variation coefficients for the analyzed amines ranged between 0.49% and 3.92%. Obtained BA derivatives enhanced separation the analytes on chromatograms due to the inhibition of hydrolysis reaction and the reduction of by-products formation.
Topics: Benzene Derivatives; Biogenic Amines; Chromatography, High Pressure Liquid; Chromatography, Reverse-Phase; Crystallography, X-Ray; Histamine; Limit of Detection; Magnetic Resonance Spectroscopy; Models, Molecular; Phenethylamines; Tryptamines; Tyramine; Wine
PubMed: 24928246
DOI: 10.1016/j.aca.2014.05.028 -
Journal of Synchrotron Radiation Jan 2011To reveal the chemical changes and geometry changes of active-site residues that cooperate with a reaction is important for understanding the functional mechanism of...
To reveal the chemical changes and geometry changes of active-site residues that cooperate with a reaction is important for understanding the functional mechanism of proteins. Consecutive temporal analyses of enzyme structures have been performed during reactions to clarify structure-based reaction mechanisms. Phenylethylamine oxidase from Arthrobacter globiformis (AGAO) contains a copper ion and topaquinone (TPQ(ox)). The catalytic reaction of AGAO catalyzes oxidative deaminations of phenylethylamine and consists of reductive and oxidative half-reactions. In the reduction step, TPQ(ox) reacts with a phenylethylamine (PEA) substrate giving rise to a topasemiquinone (TPQ(sq)) formed Schiff-base and produces phenylacetaldehyde. To elucidate the mechanism of the reductive half-reaction, an attempt was made to trap the reaction intermediates in order to analyze their structures. The reaction proceeded within the crystals when AGAO crystals were soaked in a PEA solution and freeze-trapped in liquid nitrogen. The reaction stage of each crystal was confirmed by single-crystal microspectrometry, before X-ray diffraction measurements were made of four reaction intermediates. The structure at 15 min after the onset of the reaction was analyzed at atomic resolution, and it was shown that TPQ(ox) and some residues in the substrate channel were alternated via catalytic reductive half-reactions.
Topics: Amine Oxidase (Copper-Containing); Arthrobacter; Catalysis; Crystallography, X-Ray; Dihydroxyphenylalanine; Phenethylamines; Schiff Bases; X-Ray Diffraction
PubMed: 21169693
DOI: 10.1107/S0909049510034989 -
Journal of the American Chemical Society Aug 2016The drug olsalazine (H4olz) was employed as a ligand to synthesize a new series of mesoporous metal-organic frameworks that are expanded analogues of the well-known...
The drug olsalazine (H4olz) was employed as a ligand to synthesize a new series of mesoporous metal-organic frameworks that are expanded analogues of the well-known M2(dobdc) materials (dobdc(4-) = 2,5-dioxido-1,4-benzenedicarboxylate; M-MOF-74). The M2(olz) frameworks (M = Mg, Fe, Co, Ni, and Zn) exhibit high surface areas with large hexagonal pore apertures that are approximately 27 Å in diameter. Variable temperature H2 adsorption isotherms revealed strong adsorption at the open metal sites, and in situ infrared spectroscopy experiments on Mg2(olz) and Ni2(olz) were used to determine site-specific H2 binding enthalpies. In addition to its capabilities for gas sorption, the highly biocompatible Mg2(olz) framework was also evaluated as a platform for the delivery of olsalazine and other encapsulated therapeutics. The Mg2(olz) material (86 wt % olsalazine) was shown to release the therapeutic linker through dissolution of the framework under simulated physiological conditions. Furthermore, Mg2(olz) was used to encapsulate phenethylamine (PEA), a model drug for a broad class of bioactive compounds. Under simulated physiological conditions, Mg2(olz)(PEA)2 disassembled to release PEA from the pores and olsalazine from the framework itself, demonstrating that multiple therapeutic components can be delivered together at different rates. The low toxicity, high surface areas, and coordinatively unsaturated metal sites make these M2(olz) materials promising for a range of potential applications, including drug delivery in the treatment of gastrointestinal diseases.
Topics: Adsorption; Aminosalicylic Acids; Binding Sites; Biocompatible Materials; Chemistry, Organic; Drug Carriers; Drug Delivery Systems; Gastrointestinal Diseases; Humans; Hydrogen; Ligands; Metal-Organic Frameworks; Metals; Organic Chemicals; Phenethylamines; Phthalic Acids; Spectrophotometry, Infrared; Surface Properties
PubMed: 27486905
DOI: 10.1021/jacs.6b03523