Browse
Submit Data
Databases
API
Help

Dataset Information

24 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthetic Evidence of the Amadori-Type Alkylation of Biogenic Amines by the Neurotoxic Metabolite Dopegal.

ABSTRACT: The neurotransmitter metabolite 3,4-dihydroxy-phenylglycolaldehyde (dopegal) damages neurons and the myocardium by protein cross-linking, resulting in conglomerations and cell death. We investigated this process on a synthetic scale, leading to the discovery of an Amadori-type rearrangement of dopegal in the reaction with several amino acids and neuropeptides. This alkylation also occurs with neurotransmitters, suggesting an influence of dopegal on neurochemical processes. The rearrangement occurs readily under physiological conditions.

SUBMITTER: Wanner MJ

PROVIDER: S-EPMC6970265 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Synthetic Evidence of the Amadori-Type Alkylation of Biogenic Amines by the Neurotoxic Metabolite Dopegal.

Wanner Martin J MJ Zuidinga Ed E Tromp Dorette S DS Vilím Jan J Jørgensen Steen Ingemann SI van Maarseveen Jan H JH

The Journal of organic chemistry 20191230 2

The neurotransmitter metabolite 3,4-dihydroxy-phenylglycolaldehyde (dopegal) damages neurons and the myocardium by protein cross-linking, resulting in conglomerations and cell death. We investigated this process on a synthetic scale, leading to the discovery of an Amadori-type rearrangement of dopegal in the reaction with several amino acids and neuropeptides. This alkylation also occurs with neurotransmitters, suggesting an influence of dopegal on neurochemical processes. The rearrangement occu ...[more]

PMID: 31841007

Similar Datasets

Selective <i>N</i>-Alkylation of Amines with DMC over Biogenic Cu-Zr Bimetallic Nanoparticles.

Project description:Herein, we report the green synthesis of copper-zirconium bimetallic nanoparticles (Cu-Zr BNPs) from aqueous solutions using Azadirachta indica leaf extract as a reducing and stabilizing agent. The CuO, ZrO2 NP, and Cu-Zr BNP samples were characterized by X-ray diffraction and Fourier transform infrared (FTIR) spectroscopy, and the morphologies of the samples were analyzed by high-resolution transmission electron microscopy (HR-TEM) with selected area electron diffraction analysis (SAED). The synthesized Cu-Zr BNPs have been employed as efficient catalysts for the selective N-methylation of aromatic and aliphatic amines with dimethyl carbonate. The effect of process conditions on the percentage conversion of benzylamine with dimethyl carbonate as a model reaction has been investigated. The Cu-Zr bimetallic nanoparticle catalytic system in a 1:2 molar ratio was able to convert amines into the corresponding N-methylated amines with a selectivity up to 91% at 180 °C in 4 h. The analysis of catalytic reusability confirmed that the reported heterogeneous catalyst can be used for five consecutive cycles without much loss in activity. Thus, the current protocol can be considered as a simpler, reproducible, and environmentally benign approach for N-methylation of amines.

| S-EPMC8210448 | biostudies-literature

Oleuropein Reverses Repeated Corticosterone-Induced Depressive-Like Behavior in mice: Evidence of Modulating Effect on Biogenic Amines.

Project description:Depression is still one of challenging, and widely encountered disorders with complex etiology. The role of healthy diet and olive oil in ameliorating depression has been claimed. This study was designed to explore the effects of oleuropein; the main constituent of olive oil; on depression-like behaviors that are induced by repeated administration of corticosterone (40?mg/kg, i.p.), once a day for 21 days, in mice. Oleuropein (8, 16, and 32?mg/kg, i.p.) or fluoxetine (20?mg/kg, positive control, i.p.1) was administered 30?minutes prior to corticosterone injection. Sucrose consumption test, open-field test (OFT), tail suspension test (TST), and forced swimming test (FST) were performed. Reduced Glutathione (GSH), lipid peroxidation, and biogenic amines; serotonin, dopamine, and nor-epinephrine; levels were also analyzed in brain homogenates. Corticosterone treatment induced depression-like behaviors, it increased immobility time in the TST, OFT, and FST, decreased the number of movements in OFT, and decreased sucrose consumption. Corticosterone effect was associated with depletion of reduced glutathione and increase of lipid peroxidation, in addition to modification of biogenic amines; decreased serotonin and dopamine. Oleuropein or fluoxetine administration counteracted corticosterone-induced changes. In conclusion, oleuropein showed a promising antidepressant activity, that is evident by improving corticosterone-induced depression-like behaviors, and normalizing levels of biogenic amines.

| S-EPMC7040186 | biostudies-literature

Biogenic amines in the testis: sources, receptors and actions.

Project description:Biogenic amines are signaling molecules with multiple roles in the central nervous system and in peripheral organs, including the gonads. A series of studies indicated that these molecules, their biosynthetic enzymes and their receptors are present in the testis and that they are involved in the regulation of male reproductive physiology and/or pathology. This mini-review aims to summarize the current knowledge in this field and to pinpoint existing research gaps. We suggest that the widespread clinical use of pharmacological agonists/antagonists of these signaling molecules, calls for new investigations in this area. They are necessary to evaluate the relevance of biogenic amines for human male fertility and infertility, as well as the potential value of at least one of them as an anti-aging compound in the testis.

| S-EPMC11222591 | biostudies-literature

A dopamine metabolite stabilizes neurotoxic amyloid-β oligomers.

Project description:Aberrant soluble oligomers formed by the amyloid-β peptide (Aβ) are major pathogenic agents in the onset and progression of Alzheimer's disease. A variety of biomolecules can influence the formation of these oligomers in the brain, although their mechanisms of action are still largely unknown. Here, we studied the effects on Aβ aggregation of DOPAL, a reactive catecholaldehyde intermediate of dopamine metabolism. We found that DOPAL is able to stabilize Aβ oligomeric species, including dimers and trimers, that exert toxic effects on human neuroblastoma cells, in particular increasing cytosolic calcium levels and promoting the generation of reactive oxygen species. These results reveal an interplay between Aβ aggregation and key biochemical processes regulating cellular homeostasis in the brain.

| S-EPMC7782527 | biostudies-literature

Effect of Biogenic Amine-Degrading Lactobacillus on the Biogenic Amines and Quality in Fermented Lamb Jerky

Project description:This study compares five types of lamb jerky, namely, CO (without starter culture), PL-4 (with producing putrescine, cadaverine, histamine, and tyramine), BL4-8 (degrading putrescine, cadaverine, histamine, and tyramine), CL4-3 (degrading putrescine and tyramine), and X3-2B (degrading histamine and tyramine). A study was performed to examine the effects of starter culture on the physical–chemical quality, flavor, and biogenic amines (BAs) during fermentation and ripening. At the end of fermentation, the pH value of the BL4-8 group (4.75) was significantly lower than that of other groups (p < 0.05). After high-temperature roasting, the water activity (0.55), water content (22.6%), nitrite residue (0.41 mg/kg), and TBARS value (0.27 mg/100 g) of the X3-2B group were significantly lower than those of other groups (p < 0.05). The findings show that adding starter BL4-8, CL4-3, and X3-2B can increase the variety and content of flavor in the product. The levels of histamine, putrescine, and tyramine were significantly lower in the BL4-8, CL4-3, and X3-2B groups than in CO and PL-4 groups. This study shows that BL4-8, CL4-3, and X3-2B are potential starters for fermented meat products.

| S-EPMC9322946 | biostudies-literature

Bacteria Responsible for Producing Biogenic Amines in Sufu

Project description:Bacteria Responsible for Producing Biogenic Amines in Sufu Raw sequence reads

| PRJNA658202 | ENA

Detection of common biogenic amines in fermented sausage produced in Turkey.

Project description:The application of HPLC method to detect the BA concentration in fermented sausage was successful and proved that HPLC system and method served its purposes. Biogenic amines are generated in foods as a result of free amino acid decarboxylation by bacterial enzymes. Biogenic amines accumulations are unwanted in all foods and beverages because if consumed at high concentrations, they may induce foodborne intoxications. Histamine, putrescine, cadaverine, tyramine, tryptamine, beta-phenylethylamine, spermine and spermidine are considered to be the most important biogenic amines occurring in foods. The determination of biogenic amines in foods is of great interest due to their potential toxicity and can be used as indicators for food quality markers.

| S-EPMC6146452 | biostudies-literature

Natural Contaminants in Wines: Determination of Biogenic Amines by Chromatographic Techniques.

Project description:Biogenic amines (BAs) are natural contaminants of wine that originate from decarboxylase microorganisms involved in fermentation processes. The primary relevance of biogenic amines in food could have both toxic effects on consumers' health (i.e., allergic reactions, nausea, tremors, etc.), if present at high concentrations, and concurrently it can be considered as a remarkable indicator of quality and/or freshness. Therefore, the presence of nine biogenic amines [Tryptamine (TRP), ß-phenylethylamine (ß-PEA), putrescine (PUT), cadaverine (CAD), histamine (HIS), serotonin (SER), tyramine (TYR), spermidine (SPD), and spermine (SPM)] was investigated in red and white wine samples, which differed in the winemaking processes. The qualitative-quantitative determination of BAs was carried out by chromatographic methods (HPLC-UV/Vis and LC-ESI-MS). The analysis showed that both winemaking processes had all the nine BAs considered in the study at different amounts. Data showed that red wines had a higher concentration of PUT (10.52 mg L-1), TYR (7.57 mg L-1), and HIS (6.5 mg L-1), the BAs most involved in food poisoning, compared to white wines, probably related to the different type of fermentation (alcoholic and malolactic).

| S-EPMC8508579 | biostudies-literature

Direct ?-alkylation of primary aliphatic amines enabled by CO2 and electrostatics.

Project description:Primary aliphatic amines are important building blocks in organic synthesis due to the presence of a synthetically versatile NH2 group. N-functionalization of primary amines is well established, but selective C-functionalization of unprotected primary amines remains challenging. Here, we report the use of CO2 as an activator for the direct transformation of abundant primary aliphatic amines into valuable ?-lactams under photoredox and hydrogen atom transfer (HAT) catalysis. Experimental and computational studies suggest that CO2 not only inhibits undesired N-alkylation of primary amines, but also promotes selective intermolecular HAT by an electrostatically accelerated interaction between the in situ-generated negatively charged carbamate and the positively charged quinuclidinium radical. This electrostatic attraction overwhelms the inherent bond dissociation energies which suggest that HAT should occur unselectively. We anticipate that our findings will open up new avenues for amine functionalizations as well as selectivity control in HAT reactions.

| S-EPMC6150826 | biostudies-literature

Neurotoxic catecholamine metabolite in nociceptors contributes to painful peripheral neuropathy.

Project description:The neurotoxic effects of catecholamine metabolites have been implicated in neurodegenerative diseases. As some sensory neurons express tyrosine hydroxylase and monoamine oxidase (MAO), we investigated the potential contribution of catecholamine metabolites to neuropathic pain in a model of alcoholic neuropathy. The presence of catecholamines in sensory neurons is supported by capsaicin-stimulated epinephrine release, an effect enhanced in ethanol-fed rats. mRNA for enzymes in dorsal root ganglia involved in catecholamine uptake and metabolism, dopamine beta-hydroxylase and MAO-A, were decreased by neonatal administration of capsaicin. Ethanol-induced hyperalgesia was attenuated by systemic and local peripheral administration of inhibitors of MAO-A, reduction of norepinephrine transporter (NET) in sensory neurons and a NET inhibitor. Finally, intradermal injection of 3,4-dihydroxyphenylglycolaldehyde (DOPEGAL), a neurotoxic MAO-A catecholamine metabolite, produced robust mechanical hyperalgesia. These observations suggest that catecholamines in nociceptors are metabolized to neurotoxic products by MAO-A, which can cause neuronal dysfunction underlying neuropathic pain.

| S-EPMC2746092 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data