Search Results (74)

Biogenic amines (BA) are simple organic bases of low molecular weight, formed during decarboxylation of amino acids. Ripened cheeses provide suitable conditions for the development of bacteria and production of BAs. The aim of the present study was to investigate the presence of eight BAs in ripened cheese samples (n = 125) using a high-performance liquid chromatography with diode array detector (HPLC-DAD). Furthermore, microbiological analyses towards identification of bacteria using matrix-assisted laser desorption ionisation—time of flight mass spectrometry (MALDI-TOF MS) were performed. Cadaverine and putrescine were detected in 28.0% and 20.8% of cheese samples at concentrations ranging from 6.12 to 2871 mg/kg and 5.74 to 441 mg/kg, respectively. High amounts of putrescine and cadaverine in cheeses were associated with the presence of Hafnia alvei. Tyramine was identified in 28.0% of samples in the concentration range of 5.62–646 mg/kg. High concentrations of this amine was found in cheeses containing Enterococcus faecium and Enterococcus faecalis. Histamine content, the only BA restricted in food according to Regulation 2073/2005, was observed above 100 mg/kg in 11.2% of the cheeses. Ripened cheeses available on the local retail market may contain significant levels of biogenic amines and may pose a potential health hazard to consumers. Full article

Glyphosate (N-phosphonomethylglycine) is a widely used organophosphorus herbicide that inhibits the shikimate pathway, a crucial metabolic route responsible for the synthesis of aromatic amino acids in plants and certain microorganisms. Due to its broad-spectrum activity, glyphosate serves as the main active ingredient in various commercial herbicide formulations, including Roundup and Kalach 360 SL (KL). It poses a health hazard to animals and humans due to its persistence in soil, water erosion, and crops. The aim of our study was to continue the previous research to explore the impact of KL on bone using physico-chemical parameters and in silico studies after exposing female wistar rats for 60 days. The in silico study concerned the assessment of binding affinity and molecular interactions using computational modeling approach. The rats were allocated into three experimental groups: group 1 (n = 6) served as controls, while groups 2 and 3 received low and high doses (Dose 1: 126 mg/Kg and Dose 2: 315 mg/Kg) of KL dissolved in water, respectively. All rats were sacrificed after 60 days of exposure. XRD and FTIR spectrum analysis of bone tissues in female rats showed significant histoarchitectural changes associated with bone mineralization disruption. Our results have demonstrated that sub-chronic exposure of adult female rats to KL causes bone rarefaction, as confirmed by a previous histological study. This physico-chemical study has further confirmed the harmful impact of KL on the crystalline fraction of bone tissue, composed of hydroxyapatite crystals. In addition, the computational analyses showed that glyphosate binds to 3 Glu form of osteocalcin (3 Glu-OCN) (4MZZ) and decarboxylated osteocalcin (8I75) with good affinities and strong molecular interactions, which justified and supported the in vivo findings. In conclusion, KL may interfere with hydroxyapatite and osteocalcin and, therefore, impair bone remodeling and metabolism. Full article

This study investigates nitrogen metabolism during the middle of the second fermentation in stopped bottles of sparkling wine, focusing on two flor Saccharomyces cerevisiae yeast strains (G1 and N62) isolated from the velum of biologically aged wine. Nitrogen compounds, including amino acids, biogenic amines, and ammonium chloride, were quantified, revealing strain-specific differences in nitrogen utilization and production. Proteomic analysis identified 1053 proteins, with 127 showing significant differences between strains. Strain G1 demonstrated enhanced cell wall remodeling and prioritized nitrogen conservation via arginine and lysine biosynthesis, while strain N62 exhibited increased translational activity and alternative carbon utilization pathways. Notably, strain N62 produced higher concentrations of biogenic amines (putrescine and tyramine), likely due to its greater decarboxylation capacity. Principal Component Analysis (PCA) highlighted clear differentiation in the nitrogen compound profiles across the base wine and wines inoculated with the two strains. The proteome of strain N62 showed increased mitochondrial activity and TCA cycle involvement, facilitating faster fermentation (27 days vs. 52 days for G1), growth (46 × 10⁶ cells/mL vs. 21 × 10⁶ cells/mL for G1) and cell viability (4 × 10⁶ cells/mL vs. 0.7 × 10⁶ cells/mL for G1). These findings suggest that yeast strain selection significantly influences nitrogen metabolism and potentially aroma profiles and and fermentation dynamics in sparkling wine production. Understanding these metabolic adaptations provides valuable insights for optimizing yeast performance to enhance wine quality and preserve regional characteristics. Full article

Autism spectrum disorder (ASD) is a genetically heterogeneous syndrome characterized by repetitive, restricted, and stereotyped behaviors, along with persistent difficulties with social interaction and communication. Despite its increasing prevalence globally, the underlying pathogenic mechanisms of this complex neurodevelopmental disorder remain poorly understood. Therefore, the identification of reliable biomarkers could play a crucial role in enabling early screening and more precise classification of ASD subtypes, offering valuable insights into its physiopathology and aiding the customization of treatment or early interventions. Biogenic amines, including serotonin, histamine, dopamine, epinephrine, norepinephrine, and polyamines, are a class of organic compounds mainly produced by the decarboxylation of amino acids. A substantial portion of the genetic variation observed in ASD has been linked to genes that are either directly or indirectly involved in the metabolism of biogenic amines. Their potential involvement in ASD has become an area of growing interest due to their pleiotropic activities in the central nervous system, where they act as both neurotransmitters and neuromodulators or hormones. This review examines the role of biogenic amines in ASD, with a particular focus on genetic alterations in the enzymes responsible for their synthesis and degradation. Full article

γ-Aminobutyric acid (GABA), an endogenous amino acid widely found in living organisms, has important functions in plants such as regulating growth and development, maintaining carbon and nitrogen nutrient balance, and coping with adversity. In this study, we investigated the effects of exogenous 0.5 mmol/L GABA on the growth, antioxidant metabolism, and GABA shunt metabolism of tall fescue under 20 μmol/L Cd stress, using tall fescue (Festuca arundinacea) ‘Ruby II’ under hydroponics conditions. The results showed that (1) applying GABA for 3, 7, 11, and 15 d under Cd stress inhibited Cd transport from roots to leaves and promoted plant height, alleviating the effects of Cd stress on plant growth. (2) Exogenous 0.5 mmol/L GABA had an interesting regulatory effect on the activation of the antioxidant enzyme system induced by stress at different stages, which was accompanied by a decrease in malondialdehyde (MDA) contents and alleviated the degree of cell membrane lipid peroxidation under cadmium stress. Specifically, peroxidase (POD) enzyme activity reactions initially responded on the 3rd and 7th days of stress, and the changes in catalase (CAT) enzyme activities concentrated on the 11th and 15th days of the later stage. Ascorbate peroxidase (APX) enzyme was active throughout the whole stress period in the roots. Multiple factorial analyses further proved that the antioxidant pathway strongly influenced the survival and growth of tall fescue under stress in the presence of GABA. (3) Application of exogenous GABA activated the branching pathway for GABA synthesis from Glu decarboxylation (GABA shunt) with a higher contribution in the leaves, which induced changes in glutamate content, and plants maintained a higher endogenous GABA content and signal to regulate the plant antioxidant system and reduce cell membrane damage, thus improving the tolerance of plants to Cd stress. Full article

Leucine, isoleucine, and valine are collectively known as branched chain amino acids (BCAAs) and are often discussed in the same physiological and pathological situations. The two consecutive initial reactions of BCAA catabolism are catalyzed by the common enzymes referred to as branched chain aminotransferase (BCAT) and branched chain α-keto acid dehydrogenase (BCKDH). BCAT transfers the amino group of BCAAs to 2-ketoglutarate, which results in corresponding branched chain 2-keto acids (BCKAs) and glutamate. BCKDH performs an oxidative decarboxylation of BCKAs, which produces their coenzyme A-conjugates and NADH. BCAT2 in skeletal muscle dominantly catalyzes the transamination of BCAAs. Low BCAT activity in the liver reduces the metabolization of BCAAs, but the abundant presence of BCKDH promotes the metabolism of muscle-derived BCKAs, which leads to the production of glucose and ketone bodies. While mutations in the genes responsible for BCAA catabolism are involved in rare inherited disorders, an aberrant regulation of their enzymatic activities is associated with major metabolic disorders such as diabetes, cardiovascular disease, and cancer. Therefore, an understanding of the regulatory process of metabolic enzymes, as well as the functions of the BCAAs and their metabolites, make a significant contribution to our health. Full article

Amines are produced through various industrial and biological processes, contributing significantly to atmospheric pollution, particularly in the troposphere. Moreover, amine-related pollution raises global concerns due to its detrimental effects on human health, environmental quality, and the preservation of animal species. Low-molecular-weight volatile amines, categorized as volatile organic compounds (VOCs), are present in the atmosphere, and they represent the main cause of air pollution. Biogenic amines, resulting from the natural decarboxylation of amino acids, are released into the environment from both natural and industrial sources. Several methods have been developed so far to detect amines in the environment. In this study, we present a novel fluorescent receptor based on a Zn–Salen complex, functionalized with pyrenyl moieties and a chiral diamine bridge, to enhance its affinity for a broad range of amines. Fluorescence titrations and density functional theory (DFT) calculations reveal and explain the high binding affinity of this receptor toward selected amines, demonstrating its potential as an effective tool for amine detection. Full article

γ-Aminobutyric acid (GABA) is a widely distributed non-protein amino acid that serves as a crucial inhibitory neurotransmitter in the brain, regulating various physiological functions. As a result of its potential benefits, GABA has gained substantial interest in the functional food and pharmaceutical industries. The enzyme responsible for GABA production is glutamic acid decarboxylase (GAD), which catalyzes the irreversible decarboxylation of glutamate. Understanding the crystal structure and catalytic mechanism of GAD is pivotal in advancing our knowledge of GABA production. This article provides an overview of GAD’s sources, structure, and catalytic mechanism, and explores strategies for enhancing GABA production through fermentation optimization, metabolic engineering, and genetic engineering. Furthermore, the effects of GABA on the physiological functions of animal organisms are also discussed. To meet the increasing demand for GABA, various strategies have been investigated to enhance its production, including optimizing fermentation conditions to facilitate GAD activity. Additionally, metabolic engineering techniques have been employed to increase the availability of glutamate as a precursor for GABA biosynthesis. By fine-tuning fermentation conditions and utilizing metabolic and genetic engineering techniques, it is possible to achieve higher yields of GABA, thus opening up new avenues for its application in functional foods and pharmaceuticals. Continuous research in this field holds immense promise for harnessing the potential of GABA in addressing various health-related challenges. Full article

Substantial proteolysis occurs and free amino acids can be degraded to biogenic amines by decarboxylation during stylo (Stylosanthes guianensis) ensiling. High biogenic amine concentrations in silage are harmful to the health of ruminant animals. The purposes of this work were to (1) analyze the biogenic amines and amino acids concentrations, bacterial composition, and fermentation profile of spontaneously fermented stylo silage, (2) explore the effect of formic acid or sugar additive on these silage parameters, and (3) further reveal the correlations between silage amines and fermentation parameters, amino acids, and bacteria. Freshly chopped stylo was treated with distilled water (control), formic acid (4 mL/kg), and sugar (20 g/kg) and fermented for 28 days. The results indicated that putrescine (321 mg/kg dry matter), cadaverine (384 mg/kg dry matter), and tyramine (127 mg/kg dry matter) rapidly increased in concentration and become predominant in the control silage after 28 days of fermentation. Applying formic acid and sugar at ensiling, especially the acidifier, significantly decreased putrescine, cadaverine, tyramine, and total biogenic amine concentrations compared with the control treatment (p < 0.0001). Clostridium pabulibutyricum, Weissella cibaria and W. paramesenteroides were the predominant bacteria in the control silage, and the application of both additives remarkably lowered their relative abundance in comparison with the control treatment (p < 0.001). Correlation analysis showed that putrescine, cadaverine, and tyramine were positively related to pH, butyric acid, non-protein nitrogen, and ammonia nitrogen (p < 0.01). These amines also had significant correlations with C. pabulibutyricum, W. cibaria and W. paramesenteroides (p < 0.001). Putrescine, cadaverine, and tyramine were the main biogenic amines and C. pabulibutyricum was the predominant undesirable bacterium in naturally fermented stylo silage. C. pabulibutyricum, W. cibaria and W. paramesenteroides were positively related to putrescine, cadaverine, and tyramine formation. The application of formic acid or sugar significantly reduced the undesirable bacterial population and improved the fermentation and hygienic quality of the stylo silage. These findings lay the foundation for further elucidating the microbial mechanism underlying the main biogenic amine formation during fermentation of stylo silage. Full article

Most of the biogenic amines are naturally found in fermented foods as a consequence of amino acid decarboxylation. Their formation is ascribable to microorganisms (starters, contaminants and autochthonous) present in the food matrix. The concentration of these molecules is important for food security reasons, as they are involved in food poisoning illnesses. The most frequent amines found in foods are histamine, putrescine, cadaverine, tyramine, tryptamine, phenylethylamine, spermine and spermidine. One of the most risk-prone foods are cheeses, mostly ripened ones, which could easily accumulate amines due to their peculiar manufacturing process and ripening. Cheeses represent a pivotal food in our diet, providing for nutrients such as amino acids, calcium, vitamins and others; thus, since they are widely consumed, it is important to evaluate the presence of toxic molecules to avoid consumers’ poisoning. This review aimed to gather general information on the role of biogenic amines, their formation, the health issues and the microorganisms and processes that produce/reduce them, with a focus on their content in different types of cheese (from soft to hard cheeses) and the biotic and abiotic factors that influence their formation or reduction and concentration. Finally, a multivariate analysis was performed on the biogenic amine content, derived from data available in the literature, to obtain more information about the factors influencing their presence in cheeses. Full article

In classical methods of wine production, amino acids play a critical role, as they are fundamental to all types of fermentation. Beyond their consumption in fermentative processes, amino acids undergo several transformations, such as decarboxylation, which produces biogenic amines. These biogenic amines can increase under certain conditions, such as the presence of spoilage bacteria or during malolactic fermentation. Alternative methods of vinification were applied, using sulfur dioxide as a preservative (+SO₂) and methods without added sulfites. Alternative methods of vinification were applied using sulfur dioxide as a preservative (+SO₂) and methods without added sulfite (−SO₂). Monitoring was conducted for Cabernet Sauvignon red (CS), Cabernet Sauvignon rosé (CSR), Fetească regală still (FR), and Fetească regală frizzante (FRF). Alternative procedures employed the use of Pichia kluyveri for its ability to block the oxidation reactions of grapes, malolactic fermentation for all wines without sulfur dioxide (−SO₂) to ensure superior stability, and the use of several tannin mixtures to avoid oxidation reactions. Correlations were considered between the amino acids and biogenic amines that have a direct relation through decarboxylation or deamination. The pH of the wines, total acidity, and volatile acidity as principal factors of microbiological wine evolution remained constant. The highest mean concentrations of the detected biogenic amines were putrescine at 23.71 ± 4.82 mg/L (CSRSO₂), tyramine at 14.62 ± 1.50 mg/L (FR-SO₂), cadaverine at 4.36 ± 1.19 mg/L (CS-SO₂), histamine at 2.66 ± 2.19 mg/L (FR + SO₂), and spermidine at 9.78 ± 7.19 mg/L (FR + SO₂). The wine conditions ensured the inhibition of decarboxylases, but some correlations were found with the corresponding amino acids such as glutamine (r = −0.885, p < 0.05) (CSR-SO₂), tyrosine (r = −0,858, p < 0.05) (FR-SO₂), lysine (r = −0.906, p < 0.05) (FR-SO₂), and histamine (r = −0.987, p < 0.05) (CSR-SO₂). Multivariate analysis was performed, and no statistical differences were found between samples with (+SO₂) and without added sulfur dioxide (−SO₂). The vinification conditions ensured the wines’ stability and preservation and the conditions of producing biogenic amines at the lowest levels in order to not interfere with the olfactive and gustative characteristics. Full article

Accurate and reliable quantification of organic acids with carboxylic acid functional groups in complex biological samples remains a major analytical challenge in clinical chemistry. Issues such as spontaneous decarboxylation during ionization, poor chromatographic resolution, and retention on a reverse-phase column hinder sensitivity, specificity, and reproducibility in multiple-reaction monitoring (MRM)-based LC–MS assays. We report a targeted metabolomics method using phenylenediamine derivatization for quantifying carboxylic acid-containing metabolites (CCMs). This method achieves accurate and sensitive quantification in various biological matrices, with recovery rates from 90% to 105% and CVs ≤ 10%. It shows linearity from 0.1 ng/mL to 10 µg/mL with linear regression coefficients of 0.99 and LODs as low as 0.01 ng/mL. The library included a wide variety of structurally variant CCMs such as amino acids/conjugates, short- to medium-chain organic acids, di/tri-carboxylic acids/conjugates, fatty acids, and some ring-containing CCMs. Comparing CCM profiles of pancreatic cancer cells to normal pancreatic cells identified potential biomarkers and their correlation with key metabolic pathways. This method enables sensitive, specific, and high-throughput quantification of CCMs from small samples, supporting a wide range of applications in basic, clinical, and translational research. Full article

Trace amines are a separate, independent group of biogenic amines, close in structure to classical monoamine neurotransmitters such as dopamine, serotonin, and norepinephrine that include many products of the endogenous or bacteria-mediated decarboxylation of amino acids. A family of G protein-coupled trace amine-associated receptors (in humans, TAAR1, TAAR2, TAAR5, TAAR6, TAAR8, and TAAR9) that senses trace amines was discovered relatively recently. They are mostly investigated for their involvement in the olfaction of volatile amines encoding innate behaviors and their potential contribution to the pathogenesis of neuropsychiatric disorders, but the expression of the TAAR family of receptors is also observed in various populations of cells in the immune system. This review is focused on the basic information of the interaction of trace amines and their receptors with cells of the general immune systems of humans and other mammals. We also overview the available data on TAARs’ role in the function of individual populations of myeloid and lymphoid cells. With further research on the regulatory role of the trace amine system in immune functions and on uncovering the contribution of these processes to the pathogenesis of the immune response, a significant advance in the field could be expected. Furthermore, the determination of the molecular mechanisms of TAARs’ involvement in immune system regulation and the further investigation of their potential chemotactic role could bring about the development of new approaches for the treatment of disorders related to immune system dysfunctions. Full article

Herein, we present the first examples of amino acid decarboxylation via photochemically activated carbonyl sulfide (COS) elimination of the corresponding thioacids. This method offers a mild approach for the decarboxylation of amino acids, furnishing N-alkyl amino derivatives. The methodology was compatible with amino acids displaying both polar and hydrophobic sidechains and was tolerant towards widely used amino acid-protecting groups. The compatibility of the reaction with continuous-flow conditions demonstrates the scalability of the process. Full article

Food-borne pathogens and their toxins cause significant health problems in humans. Formation of biogenic amines (BAs) produced by microbial decarboxylation of amino acids in food is undesirable because it can induce toxic effects in consumers. Therefore, it is crucial to investigate the effects of natural additives with high bioactivity like spice extracts to inhibit the growth of these bacteria and the formation of BAs in food. In the present study, the antibacterial effects of diethyl ether spice (sumac, cumin, black pepper, and red pepper) extracts at doses of 1% (w/v) on Gram-positive (Staphylococcus aureus and Enterococcus faecalis) and Gram-negative (Klebsiella pneumoniae, Pseudomonas aeruginosa, Campylobacter jejuni, Aeromonas hydrophila, Salmonella Paratyphi A, and Yersinia enterocolitica) food-borne pathogen bacterial strains (FBP) were established. In addition, the accumulation of ammonia (AMN), trimethylamine (TMA), and biogenic amines (BAs) in tyrosine decarboxylase broth (TDB) was investigated by using high performance liquid chromatography (HPLC). Sumac extract exhibited the highest antibacterial potential against all FBPs, followed by cumin and peppers. AMN (570.71 mg/L) and TMA (53.66 mg/L) production were strongly inhibited by sumac extract in the levels of 55.10 mg/L for Y. enterocolitica and 2.76 mg/L for A. hydrophila, respectively. With the exception of S. aureus, black pepper dramatically reduced the synthesis of putrescine, serotonin, dopamine, and agmatine by FBP especially for Gram-negative ones. Furthermore, sumac extracts inhibited histamine and tyramine production by the majority of FBP. This research suggests the application of sumac extracts as natural preservatives for inhibiting the growth of FBPs and limiting the production of AMN, TMA, and BAs. Full article