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Sample records for acids biogenic amines

  1. Dry fermented sausages of Southern Italy: a comparison of free amino acids and biogenic amines between industrial and homemade products.

    PubMed

    Leggio, Antonella; Belsito, Emilia L; De Marco, Rosaria; Di Gioia, Maria L; Liguori, Angelo; Siciliano, Carlo; Spinella, Mariagiovanna

    2012-04-01

    This paper compares some important parameters and the free amino acid and biogenic amine contents of cured industrial and homemade meat products. To this aim, industrial and homemade "soppressata" and "salsiccia", typical dry fermented sausages produced in Southern Italy, were analyzed. The homemade sausages showed a higher level of free biogenic amines than that manufactured industrially, most likely because biogenic amine formation in industrial products is limited by the use of starter cultures. The industrial sausages are characterized by a higher total free amino acid content than the homemade products. Overall, free amino acid and biogenic amine contents demonstrated that appreciable differences exist between homemade and industrial sausages.

  2. Biogenic amines in natural ciders.

    PubMed

    Garai, G; Dueñas, M T; Irastorza, A; Martín-Alvarez, P J; Moreno-Arribas, M V

    2006-12-01

    Biogenic amines play an important physiological role in mammals, and high amounts of some exogenous amines in human diet may contribute to a wide variety of toxic effects. These amines are commonly found in many foodstuffs, particularly in fermented products such as cheese, meat products, beer, wine, and ciders. Here, the level of biogenic amines in some natural ciders was examined. Twenty-four samples of cider purchased from commercial sources were analyzed by reverse-phase high-performance liquid chromatography and fluorescence detection after precolumn derivatization with o-phthaldialdehyde. Amine levels were variable, ranging from not detected to 23 mg/liter. The average level of total biogenic amines in ciders was 5.94 +/- 8.42 mg/liter. Putrescine, histamine, and tyramine were the prevailing amines being present in 50.0, 37.5, and 33.3% of the ciders studied; very small amounts of ethylamine and phenylethylamine were observed in only one sample. Other cider parameters were analyzed to determine whether they affect the biogenic amine content in ciders, and the results were evaluated by applying cluster analysis and principal component analysis. Ciders that showed lower glycerol contents and higher amounts of 1,3-propanediol had much higher levels of histamine, tyramine, and putrescine, suggesting a high activity of lactic acid bacteria during cider making and thus the need for effective control of lactic acid bacteria. PMID:17186671

  3. Potential of wine-associated lactic acid bacteria to degrade biogenic amines.

    PubMed

    García-Ruiz, Almudena; González-Rompinelli, Eva M; Bartolomé, Begoña; Moreno-Arribas, M Victoria

    2011-08-01

    Some lactic acid bacteria (LAB) isolated from fermented foods have been proven to degrade biogenic amines through the production of amine oxidase enzymes. Since little is known about this in relation to wine micro-organisms, this work examined the ability of LAB strains (n=85) isolated from wines and other related enological sources, as well as commercial malolactic starter cultures (n=3) and type strains (n=2), to degrade histamine, tyramine and putrescine. The biogenic amine-degrading ability of the strains was evaluated by RP-HPLC in culture media and wine malolactic fermentation laboratory experiments. Although at different extent, 25% of the LAB isolates were able to degrade histamine, 18% tyramine and 18% putrescine, whereas none of the commercial malolactic starter cultures or type strains were able to degrade any of the tested amines. The greatest biogenic amine-degrading ability was exhibited by 9 strains belonging to the Lactobacillus and Pediococcus groups, and most of them were able to simultaneously degrade at least two of the three studied biogenic amines. Further experiments with one of the strains that showed high biogenic amine-degrading ability (L. casei IFI-CA 52) revealed that cell-free extracts maintained this ability in comparison to the cell suspensions at pH 4.6, indicating that amine-degrading enzymes were effectively extracted from the cells and their action was optimal in the degradation of biogenic amines. In addition, it was confirmed that wine components such as ethanol (12%) and polyphenols (75 mg/L), and wine additives such as SO(2) (30 mg/L), reduced the histamine-degrading ability of L. casei IFI-CA 52 at pH 4.6 by 80%, 85% and 11%, respectively, in cell suspensions, whereas the reduction was 91%, 67% and 50%, respectively, in cell-free extracts. In spite of this adverse influence of the wine matrix, our results proved the potential of wine-associated LAB as a promising strategy to reduce biogenic amines in wine.

  4. Biogenic amines in seafood: a review.

    PubMed

    Biji, K B; Ravishankar, C N; Venkateswarlu, R; Mohan, C O; Gopal, T K Srinivasa

    2016-05-01

    The biogenic amines are low molecular weight organic bases present normally in the body with biological activity influencing important physiological functions. The physiological functions of these molecules are achieved by very low concentrations in the tissues. However, significantly high amounts of biogenic amines are produced during processing and storage of seafood as a result of microbial contamination and inadequate storage conditions. Microorganisms having decarboxylase enzyme activity convert amino acids to their respective biogenic amines. Biogenic amines in seafood have been implicated as a major causative agent of food borne illness, where intoxication results from the ingestion of foods containing higher amount of biogenic amines. Hence its identification, quantitation and awareness of this food borne toxin are important in relation to food safety and spoilage. The aim of this paper is to review the basic concepts of seafood quality and safety in relation to biogenic amines along with its control measures and future areas for research. PMID:27407186

  5. Postprandial Differences in the Amino Acid and Biogenic Amines Profiles of Impaired Fasting Glucose Individuals after Intake of Highland Barley

    PubMed Central

    Liu, Liyan; Wang, Xinyang; Li, Ying; Sun, Changhao

    2015-01-01

    The aim of this study was to measure the postprandial changes in amino acid and biogenic amine profiles in individuals with impaired fasting glucose (IFG) and to investigate the changes of postprandial amino acid and biogenic amine profiles after a meal of highland barley (HB). Firstly, 50 IFG and 50 healthy individuals were recruited for the measurement of 2 h postprandial changes of amino acid and biogenic amine profiles after a glucose load. Secondly, IFG individuals received three different loads: Glucose (GL), white rice (WR) and HB. Amino acid and biogenic amine profiles, glucose and insulin were assayed at time zero and 30, 60, 90 and 120 min after the test load. The results showed fasting and postprandial amino acid and biogenic amine profiles were different between the IFG group and the controls. The level of most amino acids and their metabolites decreased after an oral glucose tolerance test, while the postprandial level of γ-aminobutyric acid (GABA) increased significantly in IFG individuals. After three different test loads, the area under the curve for glucose, insulin, lysine and GABA after a HB load decreased significantly compared to GL and WR loads. Furthermore, the postprandial changes in the level of GABA between time zero and 120 min during a HB load were associated positively with 2 h glucose and fasting insulin secretion in the IFG individuals. Thus, the HB load produced low postprandial glucose and insulin responses, which induced changes in amino acid and biogenic amine profiles and improved insulin sensitivity. PMID:26184292

  6. Postprandial Differences in the Amino Acid and Biogenic Amines Profiles of Impaired Fasting Glucose Individuals after Intake of Highland Barley.

    PubMed

    Liu, Liyan; Wang, Xinyang; Li, Ying; Sun, Changhao

    2015-07-01

    The aim of this study was to measure the postprandial changes in amino acid and biogenic amine profiles in individuals with impaired fasting glucose (IFG) and to investigate the changes of postprandial amino acid and biogenic amine profiles after a meal of highland barley (HB). Firstly, 50 IFG and 50 healthy individuals were recruited for the measurement of 2 h postprandial changes of amino acid and biogenic amine profiles after a glucose load. Secondly, IFG individuals received three different loads: Glucose (GL), white rice (WR) and HB. Amino acid and biogenic amine profiles, glucose and insulin were assayed at time zero and 30, 60, 90 and 120 min after the test load. The results showed fasting and postprandial amino acid and biogenic amine profiles were different between the IFG group and the controls. The level of most amino acids and their metabolites decreased after an oral glucose tolerance test, while the postprandial level of γ-aminobutyric acid (GABA) increased significantly in IFG individuals. After three different test loads, the area under the curve for glucose, insulin, lysine and GABA after a HB load decreased significantly compared to GL and WR loads. Furthermore, the postprandial changes in the level of GABA between time zero and 120 min during a HB load were associated positively with 2 h glucose and fasting insulin secretion in the IFG individuals. Thus, the HB load produced low postprandial glucose and insulin responses, which induced changes in amino acid and biogenic amine profiles and improved insulin sensitivity.

  7. Quality properties, fatty acids, and biogenic amines profile of fresh tilapia stored in ice.

    PubMed

    Kulawik, Piotr; Özoğul, Fatih; Glew, Robert H

    2013-07-01

    This work determines quality properties and fatty acids content of Nile tilapia (Oreochromis niloticus) stored in ice for 21 d. The quality properties consist of thiobarbituic acid (TBA), total volatile basic nitrogen (TVB-N), trimethylamine (TMA), and microbiological analysis (total viable count (TVC), total coliform, Salmonella and Staphylococcus aureus) and determination of biogenic amines content (histamine, cadaverine, putrescine, spermine, spermidine, 2-phenylethylamine, agmatine, tyramine, and ammonia). Moreover, the fat, moisture, and ash composition as well as fatty acids profile have also been analyzed. The TBA, TVB-N, and biogenic amines analysis showed rather low levels of spoilage even after 21 d of storage. The microbiological analysis, however, showed that tilapia was unsuitable for consumption after just 10 d. The fat, ash, moisture, and fatty acids profile analysis showed that tilapia is not a good source of n-3 fatty acids. The research indicated that the microbiological analysis was the best method to establish spoilage of tilapia stored in ice, of all analytical methods performed in this study.

  8. Bioactive Molecules Released in Food by Lactic Acid Bacteria: Encrypted Peptides and Biogenic Amines.

    PubMed

    Pessione, Enrica; Cirrincione, Simona

    2016-01-01

    Lactic acid bacteria (LAB) can produce a huge amount of bioactive compounds. Since their elective habitat is food, especially dairy but also vegetal food, it is frequent to find bioactive molecules in fermented products. Sometimes these compounds can have adverse effects on human health such as biogenic amines (tyramine and histamine), causing allergies, hypertensive crises, and headache. However, some LAB products also display benefits for the consumers. In the present review article, the main nitrogen compounds produced by LAB are considered. Besides biogenic amines derived from the amino acids tyrosine, histidine, phenylalanine, lysine, ornithine, and glutamate by decarboxylation, interesting peptides can be decrypted by the proteolytic activity of LAB. LAB proteolytic system is very efficient in releasing encrypted molecules from several proteins present in different food matrices. Alpha and beta-caseins, albumin and globulin from milk and dairy products, rubisco from spinach, beta-conglycinin from soy and gluten from cereals constitute a good source of important bioactive compounds. These encrypted peptides are able to control nutrition (mineral absorption and oxidative stress protection), metabolism (blood glucose and cholesterol lowering) cardiovascular function (antithrombotic and hypotensive action), infection (microbial inhibition and immunomodulation) and gut-brain axis (opioids and anti-opioids controlling mood and food intake). Very recent results underline the role of food-encrypted peptides in protein folding (chaperone-like molecules) as well as in cell cycle and apoptosis control, suggesting new and positive aspects of fermented food, still unexplored. In this context, the detailed (transcriptomic, proteomic, and metabolomic) characterization of LAB of food interest (as starters, biocontrol agents, nutraceuticals, and probiotics) can supply a solid evidence-based science to support beneficial effects and it is a promising approach as well to obtain

  9. Bioactive Molecules Released in Food by Lactic Acid Bacteria: Encrypted Peptides and Biogenic Amines

    PubMed Central

    Pessione, Enrica; Cirrincione, Simona

    2016-01-01

    Lactic acid bacteria (LAB) can produce a huge amount of bioactive compounds. Since their elective habitat is food, especially dairy but also vegetal food, it is frequent to find bioactive molecules in fermented products. Sometimes these compounds can have adverse effects on human health such as biogenic amines (tyramine and histamine), causing allergies, hypertensive crises, and headache. However, some LAB products also display benefits for the consumers. In the present review article, the main nitrogen compounds produced by LAB are considered. Besides biogenic amines derived from the amino acids tyrosine, histidine, phenylalanine, lysine, ornithine, and glutamate by decarboxylation, interesting peptides can be decrypted by the proteolytic activity of LAB. LAB proteolytic system is very efficient in releasing encrypted molecules from several proteins present in different food matrices. Alpha and beta-caseins, albumin and globulin from milk and dairy products, rubisco from spinach, beta-conglycinin from soy and gluten from cereals constitute a good source of important bioactive compounds. These encrypted peptides are able to control nutrition (mineral absorption and oxidative stress protection), metabolism (blood glucose and cholesterol lowering) cardiovascular function (antithrombotic and hypotensive action), infection (microbial inhibition and immunomodulation) and gut-brain axis (opioids and anti-opioids controlling mood and food intake). Very recent results underline the role of food-encrypted peptides in protein folding (chaperone-like molecules) as well as in cell cycle and apoptosis control, suggesting new and positive aspects of fermented food, still unexplored. In this context, the detailed (transcriptomic, proteomic, and metabolomic) characterization of LAB of food interest (as starters, biocontrol agents, nutraceuticals, and probiotics) can supply a solid evidence-based science to support beneficial effects and it is a promising approach as well to obtain

  10. Bioactive Molecules Released in Food by Lactic Acid Bacteria: Encrypted Peptides and Biogenic Amines.

    PubMed

    Pessione, Enrica; Cirrincione, Simona

    2016-01-01

    Lactic acid bacteria (LAB) can produce a huge amount of bioactive compounds. Since their elective habitat is food, especially dairy but also vegetal food, it is frequent to find bioactive molecules in fermented products. Sometimes these compounds can have adverse effects on human health such as biogenic amines (tyramine and histamine), causing allergies, hypertensive crises, and headache. However, some LAB products also display benefits for the consumers. In the present review article, the main nitrogen compounds produced by LAB are considered. Besides biogenic amines derived from the amino acids tyrosine, histidine, phenylalanine, lysine, ornithine, and glutamate by decarboxylation, interesting peptides can be decrypted by the proteolytic activity of LAB. LAB proteolytic system is very efficient in releasing encrypted molecules from several proteins present in different food matrices. Alpha and beta-caseins, albumin and globulin from milk and dairy products, rubisco from spinach, beta-conglycinin from soy and gluten from cereals constitute a good source of important bioactive compounds. These encrypted peptides are able to control nutrition (mineral absorption and oxidative stress protection), metabolism (blood glucose and cholesterol lowering) cardiovascular function (antithrombotic and hypotensive action), infection (microbial inhibition and immunomodulation) and gut-brain axis (opioids and anti-opioids controlling mood and food intake). Very recent results underline the role of food-encrypted peptides in protein folding (chaperone-like molecules) as well as in cell cycle and apoptosis control, suggesting new and positive aspects of fermented food, still unexplored. In this context, the detailed (transcriptomic, proteomic, and metabolomic) characterization of LAB of food interest (as starters, biocontrol agents, nutraceuticals, and probiotics) can supply a solid evidence-based science to support beneficial effects and it is a promising approach as well to obtain

  11. The influences of fish infusion broth on the biogenic amines formation by lactic acid bacteria

    PubMed Central

    Küley, Esmeray; Özogul, Fatih; Balikçi, Esra; Durmus, Mustafa; Ayas, Deniz

    2013-01-01

    The influences of fish infusion decarboxylase broth (IDB) on biogenic amines (BA) formation by lactic acid bacteria (LAB) were investigated. BA productions by single LAB strains were tested in five different fish (anchovy, mackerel, white shark, sardine and gilthead seabream) IDB. The result of the study showed that significant differences in ammonia (AMN) and BA production were observed among the LAB strains in fish IDB (p < 0.05). The highest AMN and TMA production by LAB strains were observed for white shark IDB. The all tested bacteria had decarboxylation activity in fish IDB. The uppermost accumulated amines by LAB strains were tyramine (TYM), dopamine, serotonin and spermidine. The maximum histamine production was observed in sardine (101.69 mg/L) and mackerel (100.84 mg/L) IDB by Leuconostoc mesenteroides subsp. cremoris and Pediococcus acidophilus, respectively. Lactobacillus delbrueckii subsp. lactis and Pediococcus acidophilus had a high TYM producing capability (2943 mg/L and 1157 mg/L) in sardine IDB. PMID:24294229

  12. Changes in the Content of Biogenic Amines and Fatty Acids in High Pressure-Processed Carp Flesh (Cyprinus carpio).

    PubMed

    KříŽek, Martin; Matějkoá, Kateřina; Dadáková, Eva; Špička, Jiří; Vácha, František; Vrchotová, NaděŽda

    2015-08-01

    Biogenic amine and fatty acid contents were determined in vacuum-packed fillets of common carp (Cyprinus carpio). Samples were pressure treated at 300 and 500 MPa and were stored at 3.5 and 12°C for up to 28 days (control, 0 MPa) and 70 days (pressure-treated). The content of eight biogenic amines (putrescine, cadaverine, spermidine, spermine, histamine, tyramine, tryptamine, and phenylethylamine) were determined. Putrescine and cadaverine were influenced by all factors (temperature, pressurization level, and time of storage). Tyramine content was the most sensitive indicator of the improper status of sample; levels exceeding 10 mg/kg indicated both the loss of meat freshness and temperature abuse, in spite of persisting good sensory indices. Neither storage temperature nor pressurization level had a statistically important effect on the contents of fatty acids. Only polyunsaturated fatty acids decreased slightly if the storage time exceeded 42 days.

  13. Impact of gluconic fermentation of strawberry using acetic acid bacteria on amino acids and biogenic amines profile.

    PubMed

    Ordóñez, J L; Sainz, F; Callejón, R M; Troncoso, A M; Torija, M J; García-Parrilla, M C

    2015-07-01

    This paper studies the amino acid profile of beverages obtained through the fermentation of strawberry purée by a surface culture using three strains belonging to different acetic acid bacteria species (one of Gluconobacter japonicus, one of Gluconobacter oxydans and one of Acetobacter malorum). An HPLC-UV method involving diethyl ethoxymethylenemalonate (DEEMM) was adapted and validated. From the entire set of 21 amino acids, multiple linear regressions showed that glutamine, alanine, arginine, tryptophan, GABA and proline were significantly related to the fermentation process. Furthermore, linear discriminant analysis classified 100% of the samples correctly in accordance with the microorganism involved. G. japonicus consumed glucose most quickly and achieved the greatest decrease in amino acid concentration. None of the 8 biogenic amines were detected in the final products, which could serve as a safety guarantee for these strawberry gluconic fermentation beverages, in this regard.

  14. Fatty acid composition and biogenic amines in acidified and fermented fish silage: a comparison study.

    PubMed

    Özyurt, Gülsün; Gökdoğan, Saadet; Şimşek, Ayşe; Yuvka, Ilknur; Ergüven, Merve; Kuley Boga, Esmeray

    2016-01-01

    In the presented study, ensiling of discard fish by acidification or fermentation was evaluated. Klunzinger's ponyfish which is a discard fish was used for the production of fish silage by acidification (3% formic acid for Method FA; 1.5% formic and 1.5% sulphuric acid for Method FASA) and fermentation (Lactobacillus plantarum for Method LP and Streptococcus thermophilus for Method ST). The chemical, microbiological and nutritional properties of the differently preserved fish silages were estimated during a storage period of 60 d at ambient temperature. Compared to the raw material, a slight increase in saturated fatty acids and a slight decrease in polyunsaturated fatty acids were observed in all silages. At the end of the storage period, the aerobic bacteria counts after applying Methods FA, FASA, LP and ST amounted to 2.35, 2.39, 5.77 and 5.43 log cfu/g, respectively. The analysis of thiobarbituric acid revealed that acidification of silages accelerated the lipid oxidation. Nine biogenic amines were found in raw fish and different silages. The initial histamine concentration in raw fish was 0.17 mg/100 g and in all silages it remained at low levels during the storage period. The initial tyramine content was found to be 1.56 mg/100 g in raw fish and increased significantly in all silages. The increase of the tyramine content in fermented silages was considerably higher than in acidified silages (23-48 mg/100 g and 5-10 mg/100 g, respectively). It can be concluded that acidified or fermented fish silage should be considered as potential feed component for animals because of its high nutritional value and appropriate microbiological and chemical quality.

  15. Fatty acid composition and biogenic amines in acidified and fermented fish silage: a comparison study.

    PubMed

    Özyurt, Gülsün; Gökdoğan, Saadet; Şimşek, Ayşe; Yuvka, Ilknur; Ergüven, Merve; Kuley Boga, Esmeray

    2016-01-01

    In the presented study, ensiling of discard fish by acidification or fermentation was evaluated. Klunzinger's ponyfish which is a discard fish was used for the production of fish silage by acidification (3% formic acid for Method FA; 1.5% formic and 1.5% sulphuric acid for Method FASA) and fermentation (Lactobacillus plantarum for Method LP and Streptococcus thermophilus for Method ST). The chemical, microbiological and nutritional properties of the differently preserved fish silages were estimated during a storage period of 60 d at ambient temperature. Compared to the raw material, a slight increase in saturated fatty acids and a slight decrease in polyunsaturated fatty acids were observed in all silages. At the end of the storage period, the aerobic bacteria counts after applying Methods FA, FASA, LP and ST amounted to 2.35, 2.39, 5.77 and 5.43 log cfu/g, respectively. The analysis of thiobarbituric acid revealed that acidification of silages accelerated the lipid oxidation. Nine biogenic amines were found in raw fish and different silages. The initial histamine concentration in raw fish was 0.17 mg/100 g and in all silages it remained at low levels during the storage period. The initial tyramine content was found to be 1.56 mg/100 g in raw fish and increased significantly in all silages. The increase of the tyramine content in fermented silages was considerably higher than in acidified silages (23-48 mg/100 g and 5-10 mg/100 g, respectively). It can be concluded that acidified or fermented fish silage should be considered as potential feed component for animals because of its high nutritional value and appropriate microbiological and chemical quality. PMID:26635094

  16. Content of biogenic amines in table olives.

    PubMed

    García-García, P; Brenes-Balbuena, M; Hornero-Méndez, D; García-Borrego, A; Garrido-Fernández, A

    2000-01-01

    Content of biogenic amines in flesh and brines of table olives was determined by high-pressure liquid chromatography analysis of their benzoyl derivatives. No biogenic amines were found in the flesh of fresh fruits at any stage of ripeness. Contents of biogenic amines in Spanish-style green or stored olives increased throughout the brining period but were always higher in the former. Putrescine was the amine found in the highest concentration. Small quantities of cadaverine were found in the samples taken after 3 months of brining. This compound and histamine, tyramine, and tryptamine were also found in samples taken after 12 months. Gordal cultivar showed the highest contents, followed by Manzanilla and Hojiblanca. No relationship was found between contents of biogenic amines and lactic acid production or table olive spoilages, although zapatera olives had considerably higher amounts than those brines that had undergone a normal process. Concentrations in directly brined olives were markedly lower than contents in Spanish-style olives. With respect to partition between flesh and brine, there was equilibrium between both media in the case of Spanish-style olives, whereas the contents in directly brined olives were higher in flesh than brine. PMID:10643779

  17. Data on recovery of 21 amino acids, 9 biogenic amines and ammonium ions after spiking four different beers with five concentrations of these analytes.

    PubMed

    Redruello, Begoña; Ladero, Victor; Del Rio, Beatriz; Fernández, María; Martín, M Cruz; Alvarez, Miguel A

    2016-12-01

    A novel chromatographic method for the simultaneous analysis of nine biogenic amines, 21 amino acids and ammonium ions in beer has been recently described in "A UHPLC method for the simultaneous analysis of biogenic amines, amino acids and ammonium ions in beer" (Redruello et al., 2017) [1]. The present article provides recovery data of the 31 analytes after spiking four different beers with five concentrations of each analyte (15, 30, 60, 120 and 240 µM). PMID:27689128

  18. Evolution of amino acids and biogenic amines throughout storage in sausages made of horse, beef and turkey meats.

    PubMed

    Rabie, Mohamed A; Peres, Cidalia; Malcata, F Xavier

    2014-01-01

    The changes in concentration of free amino acids and biogenic amines, along 28 d of storage at 4°C, were monitored in a wide range of European ripened sausages manufactured from horse, beef and turkey meats. Generally speaking, both chemical families became more concentrated with elapsing time--but rather distinct patterns were followed in each meat type: total free amino acids increased by 13-fold in the case of horse sausages, and 5-fold in the case of beef sausages, but decreased to one third in the case of turkey sausages; and total biogenic amines attained 730 mg/kg in turkey sausages, 500 mg/kg in beef sausages and 130 mg/kg in horse sausages by 28 d of refrigerated storage. For putrescine, maximum levels of 285 mg/kg were attained in turkey and 278 mg/kg in beef sausages; for cadaverine, maximum levels of 6 mg/kg in turkey and 9 mg/kg in beef; and for histamine, maximum levels of 263 mg/kg in turkey and 26 mg/kg in beef. Hence, public safety concerns may be raised in the case of turkey sausages.

  19. A UHPLC method for the simultaneous analysis of biogenic amines, amino acids and ammonium ions in beer.

    PubMed

    Redruello, Begoña; Ladero, Victor; Del Rio, Beatriz; Fernández, María; Martin, M C; Alvarez, Miguel A

    2017-02-15

    This paper reports a novel UHPLC method for simultaneously quantifying nine biogenic amines, 21 amino acids, and ammonium ions, in beer. Precision values of standard curves slopes were lower than 3.4% and recovery was between 85% and 106%, indicating the absence of matrix effect. Linear calibration curves were obtained for analyte concentrations between two and four orders of magnitude (R(2)>0.996). Repeatability tests returned mean variations of 3.2% and 0.5% for beer and a standard solution, respectively. Sensitivity ranged between 0.03mg/L and 0.63mg/L for the biogenic amines, and 0.05mg/L and 5.19mg/L for other compounds. Original data on the habitual presence of ethanolamine in beers are presented. The method allows for more samples to be assayed per unit time, it uses less solvent than other techniques and therefore reduces costs and the associated waste. It could be a valuable tool for monitoring the safety and quality of beers. PMID:27664616

  20. Determination of dansylated amino acids and biogenic amines in Cannonau and Vermentino wines by HPLC-FLD.

    PubMed

    Tuberoso, Carlo Ignazio Giovanni; Congiu, Francesca; Serreli, Gabriele; Mameli, Stefano

    2015-05-15

    Free amino acids (AA) and biogenic amines (BA) were quantified for the first time in Cannonau and Vermentino wines, the two most popular "Controlled Designation of Origin" wines from Sardinia (Italy). An analytical method for the simultaneous determination of AA and BA was developed, using selective derivatization with dansyl chloride followed by HPLC with fluorescence detection. Thirty-two compounds were identified in the wines analysed. High levels of AA were found, with proline being the most abundant with average levels of 1244 ± 398 and 1008 ± 281 mg/L in Cannonau and Vermentino wines, respectively. BA were detected at average concentrations <10mg/L, except putrescine which reached 20.5 ± 10.2mg/L in Cannonau wines. Histamine was never detected in any Vermentino wines. γ-Aminobutyric acid, 4-hydroxyproline, glycine, leucine+isoleucine and putrescine proved to be useful for differentiating Cannonau wines from Vermentino wines.

  1. Biogenic amines in wines from three Spanish regions.

    PubMed

    Landete, José M; Ferrer, Sergi; Polo, Lucía; Pardo, Isabel

    2005-02-23

    One hundred and sixty-three wines from La Rioja, Utiel-Requena, and Tarragona were analyzed to determine if there were any differences in the concentrations of six biogenic amines that are found in these three regions. The influence of grape variety, type of vinification, wine pH, malolactic fermentation, and storage in bottle on biogenic amine concentrations was studied. Results show important differences in putrescine and histamine concentrations among regions, varieties of grape, and type of wine; differences were less appreciable for the remaining biogenic amines studied. Low pH prevented biogenic amine formation. Malolactic fermentation and short storage periods in bottle (3-6 months) showed increases in histamine concentration, whereas longer periods of storage led to a general decrease in histamine. Several strains of lactic acid bacteria were isolated in this work, and their ability to form biogenic amines was assayed in synthetic media, grape must, and wine. Grape varieties, different types of winemaking, pH, and lactic acid bacteria may be responsible for the differences observed in the biogenic amine concentrations of the wines analyzed.

  2. High-performance liquid chromatography-ultraviolet detection method for the simultaneous determination of typical biogenic amines and precursor amino acids. Applications in food chemistry.

    PubMed

    Mazzucco, Eleonora; Gosetti, Fabio; Bobba, Marco; Marengo, Emilio; Robotti, Elisa; Gennaro, Maria Carla

    2010-01-13

    A reversed-phase high-performance liquid chromatography (HPLC) method was developed for the simultaneous determination in food of biogenic amines and their precursor amino acids after a precolumn derivatization with dansyl chloride. The chromatographic conditions, selected to be suitable for mass spectrometry detection, were optimized through experimental design and artificial neural networks. The HPLC-UV method was validated by comparing the separation results with those obtained through a HPLC method, working under the same chromatographic conditions but employing mass spectrometry detection. The HPLC-UV method was then applied to the analysis of different food samples, namely, cheese, clams, salami, and beer. For all of the matrices, recoveries (relative standard deviation always <5%) always >92% were obtained. The results are discussed as a function of the total biogenic amine content and of the concentration ratio between amines and precursor amino acids.

  3. Amino Acid and Biogenic Amine Profile Deviations in an Oral Glucose Tolerance Test: A Comparison between Healthy and Hyperlipidaemia Individuals Based on Targeted Metabolomics

    PubMed Central

    Li, Qi; Gu, Wenbo; Ma, Xuan; Liu, Yuxin; Jiang, Lidan; Feng, Rennan; Liu, Liyan

    2016-01-01

    Hyperlipidemia (HLP) is characterized by a disturbance in lipid metabolism and is a primary risk factor for the development of insulin resistance (IR) and a well-established risk factor for cardiovascular disease and atherosclerosis. The aim of this work was to investigate the changes in postprandial amino acid and biogenic amine profiles provoked by an oral glucose tolerance test (OGTT) in HLP patients using targeted metabolomics. We used ultra-high-performance liquid chromatography-triple quadrupole mass spectrometry to analyze the serum amino acid and biogenic amine profiles of 35 control and 35 HLP subjects during an OGTT. The amino acid and biogenic amine profiles from 30 HLP subjects were detected as independent samples to validate the changes in the metabolites. There were differences in the amino acid and biogenic amine profiles between the HLP individuals and the healthy controls at baseline and after the OGTT. The per cent changes of 13 metabolites from fasting to the 2 h samples during the OGTT in the HLP patients were significantly different from those of the healthy controls. The lipid parameters were associated with the changes in valine, isoleucine, creatine, creatinine, dimethylglycine, asparagine, serine, and tyrosine (all p < 0.05) during the OGTT in the HLP group. The postprandial changes in isoleucine and γ-aminobutyric acid (GABA) during the OGTT were positively associated with the homeostasis model assessment of insulin resistance (HOMA-IR; all p < 0.05) in the HLP group. Elevated oxidative stress and disordered energy metabolism during OGTTs are important characteristics of metabolic perturbations in HLP. Our findings offer new insights into the complex physiological regulation of metabolism during the OGTT in HLP. PMID:27338465

  4. Amino Acid and Biogenic Amine Profile Deviations in an Oral Glucose Tolerance Test: A Comparison between Healthy and Hyperlipidaemia Individuals Based on Targeted Metabolomics.

    PubMed

    Li, Qi; Gu, Wenbo; Ma, Xuan; Liu, Yuxin; Jiang, Lidan; Feng, Rennan; Liu, Liyan

    2016-01-01

    Hyperlipidemia (HLP) is characterized by a disturbance in lipid metabolism and is a primary risk factor for the development of insulin resistance (IR) and a well-established risk factor for cardiovascular disease and atherosclerosis. The aim of this work was to investigate the changes in postprandial amino acid and biogenic amine profiles provoked by an oral glucose tolerance test (OGTT) in HLP patients using targeted metabolomics. We used ultra-high-performance liquid chromatography-triple quadrupole mass spectrometry to analyze the serum amino acid and biogenic amine profiles of 35 control and 35 HLP subjects during an OGTT. The amino acid and biogenic amine profiles from 30 HLP subjects were detected as independent samples to validate the changes in the metabolites. There were differences in the amino acid and biogenic amine profiles between the HLP individuals and the healthy controls at baseline and after the OGTT. The per cent changes of 13 metabolites from fasting to the 2 h samples during the OGTT in the HLP patients were significantly different from those of the healthy controls. The lipid parameters were associated with the changes in valine, isoleucine, creatine, creatinine, dimethylglycine, asparagine, serine, and tyrosine (all p < 0.05) during the OGTT in the HLP group. The postprandial changes in isoleucine and γ-aminobutyric acid (GABA) during the OGTT were positively associated with the homeostasis model assessment of insulin resistance (HOMA-IR; all p < 0.05) in the HLP group. Elevated oxidative stress and disordered energy metabolism during OGTTs are important characteristics of metabolic perturbations in HLP. Our findings offer new insights into the complex physiological regulation of metabolism during the OGTT in HLP. PMID:27338465

  5. Control of Biogenic Amines in Fermented Sausages: Role of Starter Cultures

    PubMed Central

    Latorre-Moratalla, M.L.; Bover-Cid, Sara; Veciana-Nogués, M.T.; Vidal-Carou, M.C.

    2012-01-01

    Biogenic amines show biological activity and exert undesirable physiological effects when absorbed at high concentrations. Biogenic amines are mainly formed by microbial decarboxylation of amino acids and thus are usually present in a wide range of foods, fermented sausages being one of the major biogenic amine sources. The use of selected starter cultures is one of the best technological measures to control aminogenesis during meat fermentation. Although with variable effectiveness, several works show the ability of some starters to render biogenic amine-free sausages. In this paper, the effect of different starter culture is reviewed and the factors determining their performance discussed. PMID:22586423

  6. Production of biogenic amines by lactic acid bacteria and enterobacteria isolated from fresh pork sausages packaged in different atmospheres and kept under refrigeration.

    PubMed

    Curiel, J A; Ruiz-Capillas, C; de Las Rivas, B; Carrascosa, A V; Jiménez-Colmenero, F; Muñoz, R

    2011-07-01

    The occurrence of in vitro amino acid activity in bacterial strains associated with fresh pork sausages packaged in different atmospheres and kept in refrigeration was studied. The presence of biogenic amines in decarboxylase broth was confirmed by ion-exchange chromatography and by the presence of the corresponding decarboxylase genes by PCR. From the 93 lactic acid bacteria and 100 enterobacteria strains analysed, the decarboxylase medium underestimates the number of biogenic amine-producer strains. 28% of the lactic acid bacteria produced tyramine and presented the tdc gene. All the tyramine-producer strains were molecularly identified as Carnobacterium divergens. Differences on the relative abundance of C. divergens were observed among the different packaging atmospheres assayed. After 28 days of storage, the presence of argon seems to inhibit C. divergens growth, while packing under vacuum seems to favour it. Among enterobacteria, putrescine was the amine more frequently produced (87%), followed by cadaverine (85%); agmatine and tyramine were only produced by 13 and 1%, respectively, of the strains analysed. Packing under vacuum or in an atmosphere containing nitrogen seems to inhibit the growth of enterobacteria which produce simultaneously putrescine, cadaverine, and agmatine. Contrarily, over-wrapping or packing in an atmosphere containing argon seems to favour the growth of agmatine producer-enterobacteria. The production of putrescine and cadaverine was associated with the presence of the corresponding amino acid decarboxylase genes. The biogenic amine-producer strains were included in a wide range of enterobacterial species, including Kluyvera intermedia, Enterobacter aerogenes, Yersinia kristensenii, Serratia grimesii, Serratia ficaria, Yersinia rodhei, Providencia vermicola and Obesumbacterium proteus.

  7. Effect of γ-Aminobutyric Acid (GABA) Producing Bacteria on In vitro Rumen Fermentation, Biogenic Amine Production and Anti-oxidation Using Corn Meal as Substrate.

    PubMed

    Ku, Bum Seung; Mamuad, Lovelia L; Kim, Seon-Ho; Jeong, Chang Dae; Soriano, Alvin P; Lee, Ho-Il; Nam, Ki-Chang; Ha, Jong K; Lee, Sang Suk

    2013-06-01

    The effects and significance of γ-amino butyric acid (GABA) producing bacteria (GPB) on in vitro rumen fermentation and reduction of biogenic amines (histamine, methylamine, ethylamine, and tyramine) using corn meal as a substrate were determined. Ruminal samples collected from ruminally fistulated Holstein cows served as inoculum and corn was used as substrate at 2% dry matter (DM). Different inclusion rates of GPB and GABA were evaluated. After incubation, addition of GPB had no significant effect on in vitro fermentation pH and total gas production, but significantly increased the ammonia nitrogen (NH3-N) concentration and reduced the total biogenic amines production (p<0.05). Furthermore, antioxidation activity was improved as indicated by the significantly higher concentration of superoxide dismutase (SOD) and glutathione peroxidase (GSH-Px) among treated samples when compared to the control (p<0.05). Additionally, 0.2% GPB was established as the optimum inclusion level. Taken together, these results suggest the potential of utilizing GPB as feed additives to improve growth performance in ruminants by reducing biogenic amines and increasing anti-oxidation.

  8. Effect of γ-Aminobutyric Acid (GABA) Producing Bacteria on In vitro Rumen Fermentation, Biogenic Amine Production and Anti-oxidation Using Corn Meal as Substrate

    PubMed Central

    Ku, Bum Seung; Mamuad, Lovelia L.; Kim, Seon-Ho; Jeong, Chang Dae; Soriano, Alvin P.; Lee, Ho-Il; Nam, Ki-Chang; Ha, Jong K.; Lee, Sang Suk

    2013-01-01

    The effects and significance of γ-amino butyric acid (GABA) producing bacteria (GPB) on in vitro rumen fermentation and reduction of biogenic amines (histamine, methylamine, ethylamine, and tyramine) using corn meal as a substrate were determined. Ruminal samples collected from ruminally fistulated Holstein cows served as inoculum and corn was used as substrate at 2% dry matter (DM). Different inclusion rates of GPB and GABA were evaluated. After incubation, addition of GPB had no significant effect on in vitro fermentation pH and total gas production, but significantly increased the ammonia nitrogen (NH3-N) concentration and reduced the total biogenic amines production (p<0.05). Furthermore, antioxidation activity was improved as indicated by the significantly higher concentration of superoxide dismutase (SOD) and glutathione peroxidase (GSH-Px) among treated samples when compared to the control (p<0.05). Additionally, 0.2% GPB was established as the optimum inclusion level. Taken together, these results suggest the potential of utilizing GPB as feed additives to improve growth performance in ruminants by reducing biogenic amines and increasing anti-oxidation. PMID:25049853

  9. Reducing biogenic-amine-producing bacteria, decarboxylase activity, and biogenic amines in raw milk cheese by high-pressure treatments.

    PubMed

    Calzada, Javier; del Olmo, Ana; Picón, Antonia; Gaya, Pilar; Nuñez, Manuel

    2013-02-01

    Biogenic amines may reach concentrations of public health concern in some cheeses. To minimize biogenic amine buildup in raw milk cheese, high-pressure treatments of 400 or 600 MPa for 5 min were applied on days 21 and 35 of ripening. On day 60, counts of lactic acid bacteria, enterococci, and lactobacilli were 1 to 2 log units lower in cheeses treated at 400 MPa and 4 to 6 log units lower in cheeses treated at 600 MPa than in control cheese. At that time, aminopeptidase activity was 16 to 75% lower in cheeses treated at 400 MPa and 56 to 81% lower in cheeses treated at 600 MPa than in control cheese, while the total free amino acid concentration was 35 to 53% higher in cheeses treated at 400 MPa and 3 to 15% higher in cheeses treated at 600 MPa, and decarboxylase activity was 86 to 96% lower in cheeses treated at 400 MPa and 93 to 100% lower in cheeses treated at 600 MPa. Tyramine, putrescine, and cadaverine were the most abundant amines in control cheese. The total biogenic amine concentration on day 60, which reached a maximum of 1.089 mg/g dry matter in control cheese, was 27 to 33% lower in cheeses treated at 400 MPa and 40 to 65% lower in cheeses treated at 600 MPa. On day 240, total biogenic amines attained a concentration of 3.690 mg/g dry matter in control cheese and contents 11 to 45% lower in cheeses treated at 400 MPa and 73 to 76% lower in cheeses treated at 600 MPa. Over 80% of the histidine and 95% of the tyrosine had been converted into histamine and tyramine in control cheese by day 60. Substrate depletion played an important role in the rate of biogenic amine buildup, becoming a limiting factor in the case of some amino acids.

  10. Reducing Biogenic-Amine-Producing Bacteria, Decarboxylase Activity, and Biogenic Amines in Raw Milk Cheese by High-Pressure Treatments

    PubMed Central

    Calzada, Javier; del Olmo, Ana; Picón, Antonia; Gaya, Pilar

    2013-01-01

    Biogenic amines may reach concentrations of public health concern in some cheeses. To minimize biogenic amine buildup in raw milk cheese, high-pressure treatments of 400 or 600 MPa for 5 min were applied on days 21 and 35 of ripening. On day 60, counts of lactic acid bacteria, enterococci, and lactobacilli were 1 to 2 log units lower in cheeses treated at 400 MPa and 4 to 6 log units lower in cheeses treated at 600 MPa than in control cheese. At that time, aminopeptidase activity was 16 to 75% lower in cheeses treated at 400 MPa and 56 to 81% lower in cheeses treated at 600 MPa than in control cheese, while the total free amino acid concentration was 35 to 53% higher in cheeses treated at 400 MPa and 3 to 15% higher in cheeses treated at 600 MPa, and decarboxylase activity was 86 to 96% lower in cheeses treated at 400 MPa and 93 to 100% lower in cheeses treated at 600 MPa. Tyramine, putrescine, and cadaverine were the most abundant amines in control cheese. The total biogenic amine concentration on day 60, which reached a maximum of 1.089 mg/g dry matter in control cheese, was 27 to 33% lower in cheeses treated at 400 MPa and 40 to 65% lower in cheeses treated at 600 MPa. On day 240, total biogenic amines attained a concentration of 3.690 mg/g dry matter in control cheese and contents 11 to 45% lower in cheeses treated at 400 MPa and 73 to 76% lower in cheeses treated at 600 MPa. Over 80% of the histidine and 95% of the tyrosine had been converted into histamine and tyramine in control cheese by day 60. Substrate depletion played an important role in the rate of biogenic amine buildup, becoming a limiting factor in the case of some amino acids. PMID:23241980

  11. Biogenic amines in italian pecorino cheese.

    PubMed

    Schirone, Maria; Tofalo, Rosanna; Visciano, Pierina; Corsetti, Aldo; Suzzi, Giovanna

    2012-01-01

    The quality of distinctive artisanal cheeses is closely associated with the territory of production and its traditions. Pedoclimatic characteristics, genetic autochthonous variations, and anthropic components create an environment so specific that it would be extremely difficult to reproduce elsewhere. Pecorino cheese is included in this sector of the market and is widely diffused in Italy (∼62.000t of production in 2010). Pecorino is a common name given to indicate Italian cheeses made exclusively from pure ewes' milk characterized by a high content of fat matter and it is mainly produced in the middle and south of Italy by traditional procedures from raw or pasteurized milk. The microbiota plays a major role in the development of the organoleptic characteristics of the cheese but it can also be responsible for the accumulation of undesirable substances, such as biogenic amines (BA). Bacterial amino acid decarboxylase activity and BA content have to be investigated within the complex microbial community of raw milk cheese for different cheese technologies. The results emphasize the necessity of controlling the indigenous bacterial population responsible for high production of BA and the use of competitive adjunct cultures could be suggested. Several factors can contribute to the qualitative and quantitative profiles of BA's in Pecorino cheese such as environmental hygienic conditions, pH, salt concentration, water activity, fat content, pasteurization of milk, decarboxylase microorganisms, starter cultures, temperature and time of ripening, storage, part of the cheese (core, edge), and the presence of cofactor (pyridoxal phosphate, availability of aminases and deaminases). In fact physico-chemical parameters seem to favor biogenic amine-positive microbiota; both of these environmental factors can easily be modulated, in order to control growth of undesirable microorganisms. Generally, the total content of BA's in Pecorino cheeses can range from about 100-2400

  12. Rett syndrome - Stimulation of endogenous biogenic amines

    NASA Technical Reports Server (NTRS)

    Pelligra, R.; Norton, R. D.; Wilkinson, R.; Leon, H. A.; Matson, W. R.

    1992-01-01

    Transient hypercapnic hyperoxemia was induced in two Rett syndrome children by the administration of a gaseous mixture of 80 percent O2 and 20 percent CO2. Time course studies of neurotransmitters and their metabolites showed an immediate and marked increase in central biogenic amine turnover following inhalation of the gas mixture. The increased turnover of biogenic amines was associated with improved clinical changes. This suggests a coupled relationship and provides further support for an etiological role of neurotransmitter dysfunction in Rett syndrome. In a complementary study, elevation of pulmonary CO2 by application of a simple rebreathing device resulted in improvement of abnormal blood gases and elimination of the Cheyne-Stokes-like respiratory pattern of the Rett syndrome. Near normalization of the EEG occurred when a normal respiratory pattern was imposed by means of a respirator. Taken together, these results lead to the preliminary conclusion that cerebral hypoxemia secondary to abnormal respiratory function may contribute to diminished production of biogenic amines in Rett syndrome.

  13. Biogenic Amines in Raw and Processed Seafood

    PubMed Central

    Visciano, Pierina; Schirone, Maria; Tofalo, Rosanna; Suzzi, Giovanna

    2012-01-01

    The presence of biogenic amines (BAs) in raw and processed seafood, associated with either time/temperature conditions or food technologies is discussed in the present paper from a safety and prevention point of view. In particular, storage temperature, handling practices, presence of microbial populations with decarboxylase activity and availability of free amino acids are considered the most important factors affecting the production of BAs in raw seafood. On the other hand, some food technological treatments such as salting, ripening, fermentation, or marination can increase the levels of BAs in processed seafood. The consumption of high amount of BAs, above all histamine, can result in food borne poisoning which is a worldwide problem. The European Regulation established as maximum limits for histamine, in fishery products from fish species associated with high histidine amounts, values ranging from 100 to 200 mg/kg, while for products which have undergone enzyme maturation treatment in brine, the aforementioned limits rise to 200 and 400 mg/kg. Preventive measures and emerging methods aiming at controlling the production of BAs are also reported for potential application in seafood industries. PMID:22675321

  14. [Metabolism of various biogenic amines in acute viral neuroinfections].

    PubMed

    Martynenko, I N; Shchegoleva, R A; Ponomarenko, V P; Leshchinskaia, E V; Kodkind, G Kh

    1983-01-01

    The metabolism of biogenic amines was examined in 62 patients with various acute viral neuroinfections. The control group consisted of 57 persons. Depending on the process character and disease period variations of the levels of serotonin, 5-hydroxyindolylacetic acid, coeruloplasmin and histamine were discovered. A comparison of the results obtained with the clinical course of the diseases revealed a certain correlation, especially in patients with acute meningoencephalitis.

  15. Influence of packaging conditions on biogenic amines and fatty acids evolution during 15months storage of a typical spreadable salami ('Nduja).

    PubMed

    Loizzo, Monica Rosa; Spizzirri, U Gianfranco; Bonesi, Marco; Tundis, Rosa; Picci, Nevio; Restuccia, Donatella

    2016-12-15

    The study evaluated the fatty acids and the biogenic amines (BAs) in 'Nduja of Spilinga stored in different packaging materials (i.e. natural casing under vacuum, glass jar, aluminum tube and OVTENE®) during 15months of shelf-life. Raw materials and pepper mixture were analysed as well. BAs concentrations increased with time, tyramine (TYR), putrescine (PUT) and cadaverine (CAD) were the most abundant. BAs in natural casing were always higher than those found in glass jar, aluminum tube and OVTENE®. Total fatty acids were characterized by higher level of unsaturated fatty acid that decreased with time (glass jar>natural casing under vacuum>aluminum tube>OVTENE®). The reduction of PUFA is the consequence of the increase of peroxides and carbonyls reacting with amino acids to form BAs. This was confirmed by Pearson's correlation matrices implying that lipid oxidation processes were in some way linked to the chemical production of BAs. PMID:27451162

  16. Cyclodextrin-modified MEKC method for quantification of selected acidic metabolites of catecholamines in the presence of various biogenic amines. Application to diagnosis of neuroblastoma.

    PubMed

    Miękus, Natalia; Kowalski, Piotr; Olędzka, Ilona; Plenis, Alina; Bień, Ewa; Miękus, Aleksandra; Krawczyk, Małgorzata; Adamkiewicz-Drożyńska, Elżbieta; Bączek, Tomasz

    2015-10-15

    The main aim of the presented study was to develop a reliable and non-time-consuming method for the simultaneous separation of biogenic amines (BAs) like noradrenalin, adrenalin, dopamine and their main metabolites - homovanillic acid (HVA), vanillylmandelic acid (VMA), 3,4-dihydroxyphenylacetic acid (DOPAC) - in urine samples. To achieve this, the validated α-cyclodextrin (α-CD)-modified micellar electrokinetic chromatography method with DAD was proposed. The optimized separation parameters were as follows: background electrolyte was composed of 10mM sodium tetraborate decahydrate, 30mM SDS, 15% (v/v) methanol and 25mM α-CD, adjusted to pH 9.36 with 1N NaOH; uncoated fused silica capillary (75μm i.d.×60.2cm length); λ=200nm; injection time 5s, applied voltage 25kV; temperature 25 (±0.1)°C. Next, the developed MEKC method was practically applied to evaluate the levels of selected acidic metabolites of catecholamines like HVA, VMA and DOPAC in urine samples collected from patients diagnosed with neuroblastoma (NB), melanotic neuroectodermal tumor of infancy (MNTI). PMID:26402573

  17. Control of Biogenic Amines in Food—Existing and Emerging Approaches

    PubMed Central

    Naila, Aishath; Flint, Steve; Fletcher, Graham; Bremer, Phil; Meerdink, Gerrit

    2010-01-01

    Biogenic amines have been reported in a variety of foods, such as fish, meat, cheese, vegetables, and wines. They are described as low molecular weight organic bases with aliphatic, aromatic, and heterocyclic structures. The most common biogenic amines found in foods are histamine, tyramine, cadaverine, 2-phenylethylamine, spermine, spermidine, putrescine, tryptamine, and agmatine. In addition octopamine and dopamine have been found in meat and meat products and fish. The formation of biogenic amines in food by the microbial decarboxylation of amino acids can result in consumers suffering allergic reactions, characterized by difficulty in breathing, itching, rash, vomiting, fever, and hypertension. Traditionally, biogenic amine formation in food has been prevented, primarily by limiting microbial growth through chilling and freezing. However, for many fishing based subsistence populations, such measures are not practical. Therefore, secondary control measures to prevent biogenic amine formation in foods or to reduce their levels once formed need to be considered as alternatives. Such approaches to limit microbial growth may include hydrostatic pressures, irradiation, controlled atmosphere packaging, or the use of food additives. Histamine may potentially be degraded by the use of bacterial amine oxidase or amine-negative bacteria. Only some will be cost-effective and practical for use in subsistence populations. PMID:21535566

  18. Comparison of γ-Aminobutyric Acid and Biogenic Amine Content of Different types of Ewe’s Milk Cheese Produced in Sardinia, Italy

    PubMed Central

    Porcu, Arianna; Ru, Antonio; Salaris, Margherita; Franco, Mario A.; De Santis, Enrico P.L.

    2015-01-01

    The bioactive compounds γ-aminobutyric acid (GABA) and biogenic amines (BA), together with protein-free amino acids, were measured by high-performance liquid chromatography in ewe’s milk cheeses produced in Sardinia with different technological traits. The study included three types of cheese: Pecorino Sardo PDO, Pecorino and Casu Marzu. Farmhouse Casu Marzu and Pecorino showed GABA content (maximum levels: 1001.3 and 378.1 mg 100 g–1 respectively) that had never been found so high in cheese before, suggesting that these types of cheese present ideal conditions to produce GABA. These two types of cheese also showed high levels of BA (their total maximum levels were 1035.7 and 288.0 mg 100 g–1 respectively). Pearson correlation analysis detected significant correlation between GABA and the main BA present in the cheeses (tyramine, cadaverine and putrescine), suggesting that the factors affecting the production of GABA are the same as those influencing BA formation. PMID:27800396

  19. Factors Influencing Biogenic Amines Accumulation in Dairy Products

    PubMed Central

    Linares, Daniel M.; del Río, Beatriz; Ladero, Victor; Martínez, Noelia; Fernández, María; Martín, María Cruz; Álvarez, Miguel A.

    2012-01-01

    Fermented foods are among the food products more often complained of having caused episodes of biogenic amines (BA) poisoning. Concerning milk-based fermented foods, cheese is the main product likely to contain potentially harmful levels of BA, specially tyramine, histamine, and putrescine. Prompted by the increasing awareness of the risks related to dietary uptake of high biogenic amine loads, in this review we report all those elaboration and processing technological aspects affecting BA biosynthesis and accumulation in dairy foods. Improved knowledge of the factors involved in the synthesis and accumulation of BA should lead to a reduction in their incidence in milk products. Synthesis of BA is possible only when three conditions converge: (i) availability of the substrate amino acids; (ii) presence of microorganisms with the appropriate catabolic pathway activated; and (iii) environmental conditions favorable to the decarboxylation activity. These conditions depend on several factors such as milk treatment (pasteurization), use of starter cultures, NaCl concentration, time, and temperature of ripening and preservation, pH, temperature, or post-ripening technological processes, which will be discussed in this chapter. PMID:22783233

  20. Protective effect of resveratrol on fluoride induced alteration in protein and nucleic acid metabolism, DNA damage and biogenic amines in rat brain.

    PubMed

    Pal, Sudipta; Sarkar, Chaitali

    2014-09-01

    Fluoride, a well-established environmental carcinogen, has been found to cause various neurodegenerative diseases in human. Sub-acute exposure to fluoride at a dose of 20mg/kgb.w./day for 30 days caused significant alteration in pro-oxidant/anti-oxidant status of brain tissue as reflected by perturbation of reduced glutathione content, increased lipid peroxidation, protein carbonylation, nitric oxide and free hydroxyl radical production and decreased activities of antioxidant enzymes. Decreased proteolytic and transaminase enzymes' activities, protein and nucleic acid contents and associated DNA damage were observed in the brain of fluoride intoxicated rats. The neurotransmitters dopamine (DA), norepinephrine (NE) and serotonin level was also significantly altered after fluoride exposure. Protective effect of resveratrol on fluoride-induced metabolic and oxidative dysfunctions was evaluated. Resveratrol was found to inhibit changes in metabolic activities restoring antioxidant status, biogenic amine level and structural organization of the brain. Our findings indicated that resveratrol imparted antioxidative role in ameliorating fluoride-induced metabolic and oxidative stress in different regions of the brain.

  1. Biogenic amine accumulation in silver carp sausage inoculated with Lactobacillus plantarum plus Saccharomyces cerevisiae.

    PubMed

    Nie, Xiaohua; Zhang, Qilin; Lin, Shengli

    2014-06-15

    The effect of an amine-negative mixed starter culture (Lactobacillus plantarum ZY40 plus Saccharomyces cerevisiae JM19) on biogenic amine accumulation in fermented silver carp sausage was studied. Microbial counts, pH, titratable acid and free amino acids were also determined. Putrescine, cadaverine and tyramine were the main amines formed during sausage fermentation. The contents of putrescine and cadaverine were greatly reduced by the addition of L. plantarum ZY40 plus S. cerevisiae JM19, whereas tyramine accumulation was enhanced as compared to the control batch. Histamine and spermidine were not affected by the mixed starter culture, and their levels varied slightly throughout the fermentation. Besides, no positive correction between pH, free amino acid content and biogenic amine accumulation were found.

  2. Characterization of the Production of Biogenic Amines and Gamma-Aminobutyric Acid in the Soybean Pastes Fermented by Aspergillus oryzae and Lactobacillus brevis.

    PubMed

    Kim, Nam Yeun; Ji, Geun Eog

    2015-04-01

    The production of gamma-aminobutyric acid (GABA) using GABA-producing lactic acid bacteria (LAB) has been considered to be an attractive strategy. However, some LAB may produce biogenic amines (BA), which may be of concern from the safety viewpoint. The aim of the present study was to characterize the production of GABA and BA in the soybean pastes fermented by Aspergillus oryzae (A. oryzae) FMB S46471 and GABA-producing Lactobacillus brevis (L. brevis) GABA 100. After a ripening period of 90 days, the levels of BA (putrescine, cadaverine, histamine, and tyramine) and GABA in the fermented soybean were assessed by highperformance liquid chromatography. The soybean pastes fermented by A. oryzae and L. brevis showed a range of 7,130-11,592 mg/kg for GABA, 178-305 mg/kg for tyramine, 139-163 mg/kg for putrescine, 7.4-10.8 mg/kg for histamine, and 7.1-7.9 mg/kg for cadaverine, whereas the soybean pastes fermented by A. oryzae only showed a range of 30-1,671 mg/kg for GABA, 0.8-189 mg/kg for tyramine, 1.3-85 mg/kg for putrescine, up to 3.6 mg/kg for histamine, and 0.2-2.4 mg/kg for cadaverine. The results showed that the production of GABA was accompanied by the increase in the production of BA, even though the production levels of histamine and cadaverine were very low. This is the first study to simultaneously characterize the production of BA and GABA in GABA-enriched fermented soybean pastes, and warrants further study to minimize the production of BA while optimizing the production of GABA.

  3. Novel starter cultures to inhibit biogenic amines accumulation during fish sauce fermentation.

    PubMed

    Zaman, Muhammad Zukhrufuz; Abu Bakar, Fatimah; Jinap, S; Bakar, Jamilah

    2011-01-31

    Bacteria with amine oxidase activity have become a particular interest to reduce biogenic amines concentration in food products such as meat and fish sausages. However, little information is available regarding the application of these bacteria in fish sauce. Hence, our study was aimed to investigate the effect of such starter cultures in reducing biogenic amines accumulation during fish sauce fermentation. Staphylococcus carnosus FS19 and Bacillus amyloliquefaciens FS05 isolated from fish sauce which possess amine oxidase activity were used as starter cultures in this study. Fermentation was held for 120 days at 35 °C. The pH value increased in all samples, while salt concentration remained constant throughout fermentation. Aerobic bacteria count was significantly lower (p < 0.05) in the control than in inoculated samples as a result of starter cultures addition. However, it decreased during fermentation due to the growth inhibition by high salt concentration. Proteolytic bacterial count decreased during fermentation with no significant difference (p > 0.05) among samples. These bacteria hydrolyzed protein in anchovy to produce free amino acid precursors for amines formation by decarboxylase bacteria. The presence of biogenic amines producing bacteria in this study was considered to be indigenous from raw material or contamination during fermentation, since our cultures were negative histamine producers. Amino acid histidine, arginine, lysine and tyrosine concentration decreased at different rates during fermentation as they were converted into their respective amines. In general, biogenic amines concentration namely histamine, putrescine, cadaverine and tyramine increased throughout fermentation. However, their concentrations were markedly higher (p < 0.05) in the control (without starter cultures) as compared to the samples treated with starter cultures. Histamine concentration was reduced by 27.7% and 15.4% by Staphylococcus carnosus FS19 and Bacillus

  4. The Potential of the Yeast Debaryomyces hansenii H525 to Degrade Biogenic Amines in Food

    PubMed Central

    Bäumlisberger, Mathias; Moellecken, Urs; König, Helmut; Claus, Harald

    2015-01-01

    Twenty-six yeasts from different genera were investigated for their ability to metabolize biogenic amines. About half of the yeast strains produced one or more different biogenic amines, but some strains of Debaryomyces hansenii and Yarrowia lipolytica were also able to degrade such compounds. The most effective strain D. hanseniii H525 metabolized a broad spectrum of biogenic amines by growing and resting cells. Degradation of biogenic amines by this yeast isolate could be attributed to a peroxisomal amine oxidase activity. Strain H525 may be useful as a starter culture to reduce biogenic amines in fermented food. PMID:27682120

  5. The Potential of the Yeast Debaryomyces hansenii H525 to Degrade Biogenic Amines in Food

    PubMed Central

    Bäumlisberger, Mathias; Moellecken, Urs; König, Helmut; Claus, Harald

    2015-01-01

    Twenty-six yeasts from different genera were investigated for their ability to metabolize biogenic amines. About half of the yeast strains produced one or more different biogenic amines, but some strains of Debaryomyces hansenii and Yarrowia lipolytica were also able to degrade such compounds. The most effective strain D. hanseniii H525 metabolized a broad spectrum of biogenic amines by growing and resting cells. Degradation of biogenic amines by this yeast isolate could be attributed to a peroxisomal amine oxidase activity. Strain H525 may be useful as a starter culture to reduce biogenic amines in fermented food.

  6. Biogenic amines in fish: roles in intoxication, spoilage, and nitrosamine formation--a review.

    PubMed

    Al Bulushi, Ismail; Poole, Susan; Deeth, Hilton C; Dykes, Gary A

    2009-04-01

    Biogenic amines are non-volatile amines formed by decarboxylation of amino acids. Although many biogenic amines have been found in fish, only histamine, cadaverine, and putrescine have been found to be significant in fish safety and quality determination. Despite a widely reported association between histamine and scombroid food poisoning, histamine alone appears to be insufficient to cause food toxicity. Putrescine and cadaverine have been suggested to potentiate histamine toxicity. With respect to spoilage on the other hand, only cadaverine has been found to be a useful index of the initial stage of fish decomposition. The relationship between biogenic amines, sensory evaluation, and trimethylamine during spoilage are influenced by bacterial composition and free amino acid content. A mesophilic bacterial count of log 6-7 cfu/g has been found to be associated with 5 mg histamine/100 g fish, the Food and Drug Administration (FDA) maximum allowable histamine level. In vitro studies have shown the involvement of cadaverine and putrescine in the formation of nitrosamines, nitrosopiperidine (NPIP), and nitrosopyrrolidine (NPYR), respectively. In addition, impure salt, high temperature, and low pH enhance nitrosamine formation, whereas pure sodium chloride inhibits their formation. Understanding the relationships between biogenic amines and their involvement in the formation of nitrosamines could explain the mechanism of scombroid poisoning and assure the safety of many fish products.

  7. Optimization of cationic amino starch synthesis using biogenic amines.

    PubMed

    Anthony, Renil John; Sims, Ronald C

    2013-11-01

    Harvesting microalgae presents a challenge in selecting the most economical method for low cost algal bioproducts. Previous studies have shown coagulation-flocculation to be the most efficient method for large scale microalgae harvesting. This study focused on modifying native potato starch with biogenic amines and optimizing the reaction parameters. Such modification rendered the starch cationic, with an ability to destabilize microalgae suspensions or colloids. The effect of time, temperature, and reactant concentrations on the zeta potential of the cationic amino starch was studied. Biogenic amines including putrescine, histamine, cadaverine, and tyramine were selected for study based on the number of nitrogen groups in their structure. Zeta potential for histamine cationic amino starch was significantly higher (+9.0±2.0 mV) at lower reaction temperatures, regardless of the amine to starch ratio and reaction time intervals. Putrescine, cadaverine, and tyramine cationic amino starches exhibited significantly higher zeta potential values (13.76±3.60, 6.81±1.64, and 5.68±1.60 mV, respectively) with amine to starch ratio higher than reaction stoichiometry, irrespective of reaction temperature or time intervals. This optimization study has presented a basis for designing reaction conditions for the synthesis of cationic amino starch from an inhomogeneous mix of biogenic amines derived from waste sources.

  8. Biogenic amines determination in some traditional cheeses in West Azerbaijan province of Iran

    PubMed Central

    Razavi Rohani, Seyed Mehdi; Aliakbarlu, Javad; Ehsani, Ali; Hassanzadazar, Hassan

    2013-01-01

    Biogenic amines (BA) are nitrogenous compounds that possess biological activity. The source of production is the microbial decarboxylation of amino acids. This compounds are found in various types of cheese. The aim of this work was to evaluate the BA content of some traditional cheeses in West Azerbaijan province Iran. For this purpose, 70 samples of Koopeh, 10 samples of Lighvan and 5 samples of Red Salmas cheeses were obtained from local supermarkets of different cities of West Azerbaijan province. After preparation of samples, biogenic amines content was evaluated by modified HPLC method. The presence of histamine, cadaverine, putrescine and tyramine in tested cheeses were observed. Total amount of biogenic amines was highest in Red Salmas cheese with 1426.91 ppm. It followed by Lighvan cheese and Koopeh cheese with 1008.98 and 517.71 ppm, respectively. Putrescine, cadaverine, histamine and tyramine were detected in Koopeh cheese at levels up to 156.09, 282.34, 70.80, 8.48 ppm respectively. These amines were detected also in Lighvan cheese at levels up to 277.53, 342.74, 37.58, 351.12 ppm and in Red Salmas cheese samples at levels up to 438.03, 701.05, 105.21, 182.62 ppm, respectively. Large amounts of biogenic amines can indicate non hygienic conditions and contamination of used milk for cheese production. PMID:25653782

  9. Technological Factors Affecting Biogenic Amine Content in Foods: A Review

    PubMed Central

    Gardini, Fausto; Özogul, Yesim; Suzzi, Giovanna; Tabanelli, Giulia; Özogul, Fatih

    2016-01-01

    Biogenic amines (BAs) are molecules, which can be present in foods and, due to their toxicity, can cause adverse effects on the consumers. BAs are generally produced by microbial decarboxylation of amino acids in food products. The most significant BAs occurring in foods are histamine, tyramine, putrescine, cadaverine, tryptamine, 2-phenylethylamine, spermine, spermidine, and agmatine. The importance of preventing the excessive accumulation of BAs in foods is related to their impact on human health and food quality. Quality criteria in connection with the presence of BAs in food and food products are necessary from a toxicological point of view. This is particularly important in fermented foods in which the massive microbial proliferation required for obtaining specific products is often relater with BAs accumulation. In this review, up-to-date information and recent discoveries about technological factors affecting BA content in foods are reviewed. Specifically, BA forming-microorganism and decarboxylation activity, genetic and metabolic organization of decarboxylases, risk associated to BAs (histamine, tyramine toxicity, and other BAs), environmental factors influencing BA formation (temperature, salt concentration, and pH). In addition, the technological factors for controlling BA production (use of starter culture, technological additives, effects of packaging, other non-thermal treatments, metabolizing BA by microorganisms, effects of pressure treatments on BA formation and antimicrobial substances) are addressed. PMID:27570519

  10. Technological Factors Affecting Biogenic Amine Content in Foods: A Review.

    PubMed

    Gardini, Fausto; Özogul, Yesim; Suzzi, Giovanna; Tabanelli, Giulia; Özogul, Fatih

    2016-01-01

    Biogenic amines (BAs) are molecules, which can be present in foods and, due to their toxicity, can cause adverse effects on the consumers. BAs are generally produced by microbial decarboxylation of amino acids in food products. The most significant BAs occurring in foods are histamine, tyramine, putrescine, cadaverine, tryptamine, 2-phenylethylamine, spermine, spermidine, and agmatine. The importance of preventing the excessive accumulation of BAs in foods is related to their impact on human health and food quality. Quality criteria in connection with the presence of BAs in food and food products are necessary from a toxicological point of view. This is particularly important in fermented foods in which the massive microbial proliferation required for obtaining specific products is often relater with BAs accumulation. In this review, up-to-date information and recent discoveries about technological factors affecting BA content in foods are reviewed. Specifically, BA forming-microorganism and decarboxylation activity, genetic and metabolic organization of decarboxylases, risk associated to BAs (histamine, tyramine toxicity, and other BAs), environmental factors influencing BA formation (temperature, salt concentration, and pH). In addition, the technological factors for controlling BA production (use of starter culture, technological additives, effects of packaging, other non-thermal treatments, metabolizing BA by microorganisms, effects of pressure treatments on BA formation and antimicrobial substances) are addressed. PMID:27570519

  11. Pulmonary extraction of biogenic amines during septic shock

    SciTech Connect

    Kerstein, M.D.; Kohler, J.; Gould, S.; Moseley, P.

    1982-10-01

    The effect of live Escherichia coli on the pulmonary extraction of the biogenic amines /sup 14/C 5-hydroxytryptamine, (5-HT) and /sup 3/H-epinephrine was investigated. The labeled isotopes were injected into a central venous catheter and collected from an aortic catheter. One hundred per cent of the labeled epinephrine was recovered in the control and septic state. Only 32.8 +/- 3.6% SEM of the 5-hydroxytryptamine was recovered before sepsis and 42.5 +/- 4.9% SEM after sepsis. During sepsis, mean arterial pressure fell to 58 mm Hg from 121 mm Hg. Pulmonary shunt increased from .7 +/- .05 SEM to .33 +/- .09 SEM.

  12. Biogenic amines and acute thermal stress in the rat

    NASA Technical Reports Server (NTRS)

    Williams, B. A.; Moberg, G. P.

    1975-01-01

    A study is summarized which demonstrates that depletion of the biogenic amines 5-hydroxytryptamine (5-HT) or norepinephrine (NE) alters the normal thermoregulatory responses to acute temperature stress. Specifically, NE depletion caused a significant depression in equilibrium rectal temperature at 22 C and a greater depression in rectal temperature than controls in response to cold (6 C) stress; NE depletion also resulted in a significantly higher rectal temperature response to acute heat (38 C) stress. Depletion of 5-HT had less severe effects. It remains unclear whether the primary site of action of these agents is central or peripheral.

  13. Studies of levels of biogenic amines in meat samples in relation to the content of additives.

    PubMed

    Jastrzębska, Aneta; Kowalska, Sylwia; Szłyk, Edward

    2016-01-01

    The impact of meat additives on the concentration of biogenic amines and the quality of meat was studied. Fresh white and red meat samples were fortified with the following food additives: citric and lactic acids, disodium diphosphate, sodium nitrite, sodium metabisulphite, potassium sorbate, sodium chloride, ascorbic acid, α-tocopherol, propyl 3,4,5-trihydroxybenzoate (propyl gallate) and butylated hydroxyanisole. The content of spermine, spermidine, putrescine, cadaverine, histamine, tyramine, tryptamine and 2-phenylethylamine was determined by capillary isotachophoretic methods in meat samples (fresh and fortified) during four days of storage at 4°C. The results were applied to estimate the impact of the tested additives on the formation of biogenic amines in white and red meat. For all tested meats, sodium nitrite, sodium chloride and disodium diphosphate showed the best inhibition. However, cadaverine and putrescine were characterised by the biggest changes in concentration during the storage time of all the additives. Based on the presented data for the content of biogenic amines in meat samples analysed as a function of storage time and additives, we suggest that cadaverine and putrescine have a significant impact on meat quality. PMID:26515667

  14. Studies of levels of biogenic amines in meat samples in relation to the content of additives.

    PubMed

    Jastrzębska, Aneta; Kowalska, Sylwia; Szłyk, Edward

    2016-01-01

    The impact of meat additives on the concentration of biogenic amines and the quality of meat was studied. Fresh white and red meat samples were fortified with the following food additives: citric and lactic acids, disodium diphosphate, sodium nitrite, sodium metabisulphite, potassium sorbate, sodium chloride, ascorbic acid, α-tocopherol, propyl 3,4,5-trihydroxybenzoate (propyl gallate) and butylated hydroxyanisole. The content of spermine, spermidine, putrescine, cadaverine, histamine, tyramine, tryptamine and 2-phenylethylamine was determined by capillary isotachophoretic methods in meat samples (fresh and fortified) during four days of storage at 4°C. The results were applied to estimate the impact of the tested additives on the formation of biogenic amines in white and red meat. For all tested meats, sodium nitrite, sodium chloride and disodium diphosphate showed the best inhibition. However, cadaverine and putrescine were characterised by the biggest changes in concentration during the storage time of all the additives. Based on the presented data for the content of biogenic amines in meat samples analysed as a function of storage time and additives, we suggest that cadaverine and putrescine have a significant impact on meat quality.

  15. Distribution and function of biogenic amines in the heart of Nautilus pompilius L. (Cephalopoda, Tetrabranchiata).

    PubMed

    Springer, Jochen; Ruth, Peter; Beuerlein, Knut; Palus, Sandra; Schipp, Rudolf; Westermann, Bettina

    2005-06-01

    Biogenic amines (serotonin and catecholamines), play an important role in the control of the blood flow not only in vertebrates, but also in invertebrates such as cephalopods. In contrast to the well investigated hearts of the a 'modern', coleoid cephalopods, the innervation of the heart of the archaic Nautilus pompilius L. has not been studied in detail. In this study the distribution and effects of biogenic amines in the Nautilus heart were investigated. Serotonin and catecholamines were visualised by the glyxoylic acid induced fluorescence. High performance liquid chromatotography analysis was performed to discriminate between the catecholamines, which showed a high content of noradrenaline in the 4 auricles, the aorta and the ventricle, whereas the ventricle showed a high dopamine content. Adrenaline was found at a very low concentration in the ventricle. Serotonin and dopamine were also immunohistochemically localised to larger nerves and throughout the heart, respectively. In organ bath experiments, the auricles showed little spontaneous activity. After adding serotonin, they displayed rhythmical contractions, which were accelerated dose-dependently by noradrenaline. In summary, these data suggest an important role for biogenic amines in the control of the heart of Nautilus pompilius L., with serotonin possibly stimulating excitatory nerve fibres, whereas noradrenaline is likely to influence the muscle contraction itself.

  16. Genome Sequence Analysis of the Biogenic Amine-Degrading Strain Lactobacillus casei 5b

    PubMed Central

    Ladero, Victor; Herrero-Fresno, Ana; Martinez, Noelia; del Río, Beatriz; Linares, Daniel M.; Fernández, María; Martín, María Cruz

    2014-01-01

    We here report a 3.02-Mbp annotated draft assembly of the Lactobacillus casei 5b genome. The sequence of this biogenic amine-degrading dairy isolate may help identify the mechanisms involved in the catabolism of biogenic amines and perhaps shed light on ways to reduce the presence of these toxic compounds in food. PMID:24435875

  17. Biogenic amines, amino acids and microflora changes in Indian mackerel (Rastrellinger kanagurta) stored at ambient (25-29 °C) and ice temperature (0 °C).

    PubMed

    Chong, Cheong Yew; Abu Bakar, Fatimah; Rahman, Russly Abdul; Bakar, Jamilah; Zaman, Muhammad Zukhrufuz

    2014-06-01

    Biogenic amines formation in Indian mackerel of tropical region was investigated during storage at ambient (25-29 °C) and ice temperature (0 °C) in relation with changes of amino acids content and amines forming bacteria. All amines increased significantly during storage at two temperatures except for spermidine and spermine. Histamine concentration of 363.5 ppm was detected after 16 h stored at ambient temperature. Aerobic plate count of fish stored at ambient temperature reached 6.98 log CFU g(-1) after 16 h, close to the upper limit (7 log CFU g(-1)) suggested by International Commission on the Microbiological Specifications for Foods (ICMSF). However, proper icing procedure retarded the formation of histamine effectively, resulting only 8.31 ppm after 16 days of ice storage. Aerobic plate count of 5.99 and 7.72 log CFU g(-1) were recorded for fish stored in ice after 16 days and ambient temperature after 20 h, respectively. Histamine exhibited high correlation with histidine (r(2) = -0.963, P < 0.01) as well as cadaverine with lysine (r(2) = -0.750, P < 0.05). However, tyramine-tyrosine demonstrated a weaker relationship (r(2) = -0.138, P > 0.05). As storage time progressed, the amines forming bacteria grew significantly except for that stored in ice. PMID:24876644

  18. Diurnal patterns in brain biogenic amines of rats exposed to 60-Hz electric fields

    SciTech Connect

    Vasquez, B.J.; Anderson, L.E.; Lowery, C.I.; Adey, W.R.

    1988-01-01

    Levels of brain neurotransmitters and their metabolites, as well as concentrations of enzymes associated with their synthesis and metabolism, fluctuate during the day in patterns defined as circadian. The present study examined these rhythms in albino rats exposed to 60-Hz electric fields. Thirty-six animals were exposed to a 39 kV/m field for 4 weeks, 20 h/day, in a parallel-plate electrode system. A group of 36 sham animals was similarly handled and housed in a nonenergized exposure system. On the sampling day, animals were sacrificed at 4-h intervals throughout the 24-h day. Brains were removed, dissected, and kept frozen until chemically analyzed. The levels of biogenic amines and their acidic metabolites in the striatum, hypothalamus, and hippocampus were determined by high-performance liquid chromatography with electrochemical detection (HPLC-ECD) methods. Repeated exposure to 60-Hz electric fields produced significant alterations in the diurnal rhythms of several biogenic amines: dihydroxyphenylacetic acid (DOPAC, the primary metabolite of dopamine in the rat) in the striatum, and norepinephrine, dopamine, and 5-hydroxyindoleacetic acid (5-HIAA; serotonin metabolite) in the hypothalamus. Levels of serotonin in the striatum and hypothalamus showed clear circadian patterns that was not affected by the field. No diurnal or field-related changes were observed in the hippocampal amines.

  19. Biogenic amines at a low level of evolution: Production, functions and regulation in the unicellular Tetrahymena.

    PubMed

    Csaba, György

    2015-06-01

    The unicellular eukaryote Tetrahymena synthesize, store and secrete biogenic amines (histamine, serotonin, epinephrine, dopamine, melatonin) and also can take up amines from the milieu. It also has (G-protein-coupled) receptors (binding sites) for these amines as well, as second messengers. The factors infuencing the mentioned processes are shown. For certain amines the genes and the coded enzymes are demonstrated. The amines influence phagocytosis, cell division, ciliary regeneration, glucose metabolism and chemotaxis. There are interhormone actions between the amines, and between the amines and other hormones produced by Tetrahymena. The critical review discusses the role of amines in the early stages of evolution and compares this to their functions in mammals. It tries to give answer how and why biogenic amines were selected to hormones, and why new functions formed for them in higher ranked animals, preserving also the ancient ones.

  20. Effect of biogenic amines on phagocytosis in Tetrahymena thermophila.

    PubMed

    Quiñones-Maldonado, V; Renaud, F L

    1987-11-01

    Stimulation of phagocytosis by serotonin and catecholamines in Tetrahymena grown in proteose-peptone medium proved to be concentration dependent, the optimal concentrations being approximately 0.1 to 1.0 microM. The serotonergic antagonists, spiperone, and metergoline, also stimulated the process, whereas the beta- and alpha-adrenergic antagonists, propranolol, alprenolol, and ergocryptine, had no effect or inhibited phagocytosis. A wide variety of derivatives of the biogenic amines had no effect on phagocytosis, demonstrating the specificity of recognition mechanism for neurohormones in Tetrahymena. Such hormones act by at least two independent mechanisms, one for adrenergic agonists, another for dopamine. Presumably, recognition mechanisms for hormones in protozoa resemble in some respects those in multicellular organisms, therefore bespeaking a common origin.

  1. Biogenic amine production by Lactococcus lactis subsp. cremoris strains in the model system of Dutch-type cheese.

    PubMed

    Flasarová, Radka; Pachlová, Vendula; Buňková, Leona; Menšíková, Anna; Georgová, Nikola; Dráb, Vladimír; Buňka, František

    2016-03-01

    The aim of this study was to compare the biogenic amine production of two starter strains of Lactococcus lactis subsp. cremoris (strains from the Culture Collection of Dairy Microorganisms - CCDM 824 and CCDM 946) with decarboxylase positive activity in a model system of Dutch-type cheese during a 90-day ripening period at 10°C. During ripening, biogenic amine and free amino acid content, microbiological characteristics and proximate chemical properties were observed. By the end of the ripening period, the putrescine content in both samples with the addition of the biogenic amine producing strain almost evened out and the concentration of putrescine was >800mg/kg. The amount of tyramine in the cheeses with the addition of the strain of CCDM 824 approached the limit of 400mg/kg by the end of ripening. In the cheeses with the addition of the strain of CCDM 946 it even exceeded 500mg/kg. In the control samples, the amount of biogenic amines was insignificant.

  2. Validation of an HPLC Analytical Method for Determination of Biogenic Amines in Agricultural Products and Monitoring of Biogenic Amines in Korean Fermented Agricultural Products.

    PubMed

    Yoon, Hyeock; Park, Jung Hyuck; Choi, Ari; Hwang, Han-Joon; Mah, Jae-Hyung

    2015-09-01

    An HPLC analytical method was validated for the quantitative determination of biogenic amines in agricultural products. Four agricultural foods, including apple juice, Juk, corn oil and peanut butter, were selected as food matrices based on their water and fat contents (i.e., non-fatty liquid, non-fatty solid, fatty liquid and fatty solid, respectively). The precision, accuracy, recovery, limit of detection (LOD) and quantification (LOQ) were determined to test the validity of an HPLC procedure for the determination of biogenic amines, including tryptamine, β-phenylethylamine, putrescine, cadaverine, histamine, tyramine, spermidine and spermine, in each matrix. The LODs and LOQs for the biogenic amines were within the range of 0.01~0.10 mg/kg and 0.02~0.31 mg/kg, respectively. The relative standard deviation (RSD) of intraday for biogenic amine concentrations ranged from 1.86 to 5.95%, whereas the RSD of interday ranged from 2.08 to 5.96%. Of the matrices spiked with biogenic amines, corn oil with tyramine and Juk with putrescine exhibited the least accuracy of 84.85% and recovery rate of 89.63%, respectively, at the lowest concentration (10 mg/kg). Therefore, the validation results fulfilled AOAC criteria and recommendations. Subsequently, the method was applied to the analysis of biogenic amines in fermented agricultural products for a total dietary survey in Korea. Although the results revealed that Korean traditional soy sauce and Doenjang contained relatively high levels of histamine, the amounts are of no concern if these fermented agricultural products serve as condiments. PMID:26483889

  3. Study on biogenic amines in various dry salted fish consumed in China

    NASA Astrophysics Data System (ADS)

    Wu, Yanyan; Chen, Yufeng; Li, Laihao; Yang, Xianqing; Yang, Shaoling; Lin, Wanling; Zhao, Yongqiang; Deng, Jianchao

    2016-08-01

    This study was carried out to investigate the biogenic amines (BAs), physicochemical property and microorganisms in dry salted fish, a traditional aquatic food consumed in China. Forty three samples of dry salted fish were gathered from retail and wholesale markets and manufacturers, which had been produced in various regions in China. Cadaverine (CAD) and putrescine (PUT) were quantitatively the most common biogenic amines. About 14% of the samples exceeded the histamine content standards established by the FDA and/or EU. The highest histamine content was found in Silver pomfret ( Pampus argenteus) (347.79 mg kg-1). Five of forty three samples exceeded the acceptable content of TYR (100 mg kg-1), and 23.26% of dried-salted fish contained high contents of biogenic amines (above 600 mg kg-1). In addition, species, regions, pickling processes and drying methods made the physicochemical property, microorganisms and biogenic amines in dry salted fish to be different to some extents. The total plate count (TPC) was much higher than that of total halophilic bacteria in all samples. The biogenic amines, physicochemical property and microbiological counts exhibited large variations among samples. Furthermore, no significant correlation between biogenic amines and physicochemical property and TPC was observed. This study indicated that dry salted fish may still present healthy risk for BAs, depending on the processing methods, storage conditions among others.

  4. Determination of biogenic amines in beer and wine by capillary electrophoresis-tandem mass spectrometry.

    PubMed

    Daniel, Daniela; Dos Santos, Vagner Bezerra; Vidal, Denis Tadeu Rajh; do Lago, Claudimir Lucio

    2015-10-16

    A capillary electrophoresis-tandem mass spectrometry (CE-MS/MS) method for the simultaneous assessment of nine biogenic amines (spermine, spermidine, putrescine, cadaverine, histamine, phenylethylamine, tryptamine, tyramine, and urocanic acid) in commercial samples of beer and wine is introduced. The samples were submitted to a simple clean-up step with poly(vinylpolypyrrolidone) followed by filtration. Electrophoretic separation in a polyvinyl alcohol (PVA)-coated capillary using 0.5 mol L(-1) acetic acid (pH 2.5) as background electrolyte and detection by electrospray-tandem mass spectrometry was employed. The range of the correlation coefficients of the calibration curves of the analyzed compounds was 0.996-0.999, and the limits of detection and limits of quantification were in the range of 1-2 μg L(-1) and 3-8 μg L(-1), respectively. The recovery values for samples spiked at three concentration levels (0.2, 0.5, and 1.0 mg L(-1)) ranged from 87 to 113% with standard deviation not greater than 5.8%. The use of a PVA-coated silica capillary allows suppressing the electroosmotic flow and, consequently, increasing of the separation efficiency. The method was successfully used to determine biogenic amines in commercial samples of beer and wine.

  5. Determination of biogenic amines in beer and wine by capillary electrophoresis-tandem mass spectrometry.

    PubMed

    Daniel, Daniela; Dos Santos, Vagner Bezerra; Vidal, Denis Tadeu Rajh; do Lago, Claudimir Lucio

    2015-10-16

    A capillary electrophoresis-tandem mass spectrometry (CE-MS/MS) method for the simultaneous assessment of nine biogenic amines (spermine, spermidine, putrescine, cadaverine, histamine, phenylethylamine, tryptamine, tyramine, and urocanic acid) in commercial samples of beer and wine is introduced. The samples were submitted to a simple clean-up step with poly(vinylpolypyrrolidone) followed by filtration. Electrophoretic separation in a polyvinyl alcohol (PVA)-coated capillary using 0.5 mol L(-1) acetic acid (pH 2.5) as background electrolyte and detection by electrospray-tandem mass spectrometry was employed. The range of the correlation coefficients of the calibration curves of the analyzed compounds was 0.996-0.999, and the limits of detection and limits of quantification were in the range of 1-2 μg L(-1) and 3-8 μg L(-1), respectively. The recovery values for samples spiked at three concentration levels (0.2, 0.5, and 1.0 mg L(-1)) ranged from 87 to 113% with standard deviation not greater than 5.8%. The use of a PVA-coated silica capillary allows suppressing the electroosmotic flow and, consequently, increasing of the separation efficiency. The method was successfully used to determine biogenic amines in commercial samples of beer and wine. PMID:26362807

  6. Levels of biogenic amines in retail market fermented meat products.

    PubMed

    Papavergou, Ekaterini J; Savvaidis, Ioannis N; Ambrosiadis, Ioannis A

    2012-12-15

    The qualitative and quantitative profile of biogenic amines (BA) in 50 samples of dry fermented sausages sold in Greek retail markets were determined by HPLC. Putrescine, cadaverine, tryptamine, β-phenylethylamine spermidine, spermine were analysed by UV detection after pre-column derivatization with benzoyl chloride, whereas tyramine and histamine were analysed by fluorescence detection after post-column derivatization with o-phthaldialdehyde (OPA). With the exception of spermidine and spermine a wide variation of BA levels was observed among the samples. Of the BA examined, tyramine, putrescine, histamine and cadaverine showed high concentrations ranging from: 0 to 510 mg/kg (median: 197.7 mg/kg), 0 to 505 mg/kg (median: 96.5mg/kg), 0 to 515 mg/kg (median: 7.0mg/kg) and 0 to 690 mg/kg (median: 3.6 mg/kg), respectively. The histamine content of 28% of the samples exceeded the toxicity limit of 100mg/kg set for histamine in some fish species. Levels of tryptamine and β-phenyl-ethylamine never exceeded 50 and 29 mg/kg, respectively. Results of the present study suggest that the amounts of BA in dry fermented sausages, sold in Greek retail markets, may pose a potential health risk for sensitive individuals or for those undergoing classical monoamine oxidase inhibiting (MAOI) drug therapy.

  7. High content of biogenic amines in Pecorino cheeses.

    PubMed

    Schirone, Maria; Tofalo, Rosanna; Fasoli, Giuseppe; Perpetuini, Giorgia; Corsetti, Aldo; Manetta, Anna Chiara; Ciarrocchi, Aurora; Suzzi, Giovanna

    2013-05-01

    Pecorino refers to Italian cheeses made exclusively from raw or pasteurized ewes' milk, characterized by a high content of fat matter and it is mainly produced in the Middle and South of Italy by traditional procedures. The autochthonous microbiota plays an important role in the organoleptic traits of Pecorino cheese and it can influence biogenic amines (BA) content. The aim of this study was to characterize from microbiological and chemical point of view 12 randomly purchased commercial cheeses produced in Abruzzo region. Moreover, the BA content and the bacteria showing a decarboxylating activity were detected. For this purpose, a real-time quantitative PCR (qPCR) was applied to evaluate histamine and tyramine-producers. The samples were well differentiated for microbial groups composition, such as aerobic mesophilic bacteria, Enterobacteriaceae, coagulase-negative staphylococci, yeasts, enterococci, mesophilic and thermophilic lactobacilli. Pathogens such as Salmonella spp., Listeria monocytogenes and Escherichia coli O157:H7 were absent in all samples. In most samples the content of BA resulted to be high, with prevalence of histamine and tyramine. In particular, total BA content reached 5861 mg/kg in Pecorino di Fossa cheese. The qPCR method resulted to be very useful to understand the role of autochthonous Pecorino cheese microbiota on BA accumulation in many different products. In fact, since the ability of microorganisms to decarboxylate aminoacids is highly variable being in most cases strain-specific, the detection of bacteria possessing this activity is important to estimate the risk of BA cheese content.

  8. Differential behavioral responses of two plant-parasitic nematodes to biogenic amines

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Hatching and infective juvenile (J2) behavior in two species of plant-parasitic nematodes, Heterodera glycines and Meloidogyne incognita, were affected by in vitro treatment with the biogenic amines dopamine, octopamine, and serotonin. While the overall responses of each species to amine exposures w...

  9. Determination of aliphatic low-molecular-weight and biogenic amines by capillary zone electrophoresis.

    PubMed

    Fekete, Agnes; Lahaniatis, Majlinda; Lintelmann, Jutta; Schmitt-Kopplin, Philippe

    2008-01-01

    Low-molecular-weight (LMW) aliphatic amines play a key role in the global nitrogen cycle, are involved in nutrient transfer, and act as buffer in the ecosystem. They are widely used as intermediates in chemical synthesis and were shown to cause occupational asthma. Biogenic amines occur in all living organisms and have an effect on the cell growth, although at high concentrations they can be toxic; some are used as cancer markers in health protection or as spoilage markers in foods. Their identification and quantification from different matrices such as human tissues or foods is of high importance. The electrophoretic separation of amines is possible as cations as a result of their high basicity; their detection, however, is more difficult because these amines contain no chromophore group. Indirect ultraviolet (UV) detection is the first presented possibility and widely used for the separation of nonderivatized amines. Otherwise, derivatization of the amines is necessary to directly detect them with laser-induced fluorescence (LIF) detection. Other detection modes such as pulse amperometric, chemiluminescence, or mass spectrometry have been also used for the determination of LMW and biogenic amines, but not on a routine basis. In this chapter, three capillary electrophoretic methods with indirect UV and LIF detection for determination of LMW aliphatic and biogenic amines are described.

  10. Recent trends in the determination of biogenic amines in fermented beverages - A review.

    PubMed

    Ordóñez, José Luis; Troncoso, Ana Maria; García-Parrilla, Maria Del Carmen; Callejón, Raquel Maria

    2016-10-01

    Biogenic amines (BA) are generally considered as a food hazard, even though there is not a threshold for these biomolecules in the European legislation, except for histamine in fishery products. These compounds are formed during the storage and processing of certain foods through microbiological activity, and when present in high concentrations, could have toxicological effects, causing health problems in consumers, especially to sensitive persons. This fact, in addition to the economical concern involved, makes it necessary to control the amounts of biogenic amines in foods. For all these reasons, literature on biogenic amines in different food products, especially in fermented beverages, is extensive. This review provides an overview of the most recent trends in the determination of biogenic amines in fermented beverages focusing on novelty, improvement and optimization of analytical methods. Hence, the different sample treatment procedures (including derivatization), the most important analytical techniques and the most frequent applications are described and discussed. Although biogenic amines have been determined in wine and other fermented beverages for decades, new advancements and technical possibilities have allowed to increase the accuracy and sensitivity of analytical methods, in order to overcome the challenges posed by the complex matrices and their high intrinsic variability. Thus, the different purposes of BA determination (food safety, production process or food microbiology research) and the most widely employed analytical techniques have been reviewed. PMID:27639140

  11. Changes in biogenic amines in mature and germinating legume seeds and their behavior during cooking.

    PubMed

    Shalaby, A R

    2000-02-01

    Ungerminated legume seeds (broad bean, chick pea and lupine) were contained all tested biogenic amines. Tryptamine (TRY) was the main biogenic amine detected, and its concentration considerably increased during the germination. beta-Phenylethylamine (PHE) was detected in small amounts and its concentration slowly increased during germination. The concentration of tyramine (TYR) showed a fluctuation pattern of changes during germination in all tested legumes. The concentrations of cadaverine (CAD) and putrescine (PUT) increased during the germination period in all tested grains. However, histamine (HIS) showed a fluctuated pattern of changes in both broad bean and lupine, and a gradual increase in chick pea. Spermidine (SPD) and spermine (SPM) contents of broad bean and chick pea showed a fluctuation pattern of change, while, a decrement trend of change was recorded for lupine along the germination period. By cooking, legume samples became free of biogenic amines which appeared in the boiling water. Heat treatment seems to have little effect on the concentration of biogenic amines in legume sprouts. The amounts of biogenic amines detected in the boiling water are less than the initial amounts of the sprouts (expected amounts).

  12. Safety assessment of the biogenic amines in fermented soya beans and fermented bean curd.

    PubMed

    Yang, Juan; Ding, Xiaowen; Qin, Yingrui; Zeng, Yitao

    2014-08-01

    To evaluate the safety of biogenic amines, high performance liquid chromatography (HPLC) was used to evaluate the levels of biogenic amines in fermented soya beans and fermented bean curd. In fermented soya beans, the total biogenic amines content was in a relatively safe range in many samples, although the concentration of histamine, tyramine, and β-phenethylamine was high enough in some samples to cause a possible safety threat, and 8 of the 30 samples were deemed unsafe. In fermented bean curd, the total biogenic amines content was more than 900 mg/kg in 19 white sufu amples, a level that has been determined to pose a safety hazard; putrescine was the only one detected in all samples and also had the highest concentration, which made samples a safety hazard; the content of tryptamine, β-phenethylamine, tyramine, and histamine had reached the level of threat to human health in some white and green sufu samples, and that may imply another potential safety risk; and 25 of the 33 samples were unsafe. In conclusion, the content of biogenic amines in all fermented soya bean products should be studied and appropriate limits determined to ensure the safety of eating these foods.

  13. Biogenic Amines Degradation by Lactobacillus plantarum: Toward a Potential Application in Wine

    PubMed Central

    Capozzi, Vittorio; Russo, Pasquale; Ladero, Victor; Fernández, María; Fiocco, Daniela; Alvarez, Miguel A.; Grieco, Francesco; Spano, Giuseppe

    2012-01-01

    Biogenic amines (BA) in wine represent a toxicological risk for the health of the consumer, with several trade implications. In this study 26 strains of Lactobacillus plantarum were analyzed for their ability to degrade BA commonly found during wine fermentation. Two strains of L. plantarum were selected in reason of their ability to degrade putrescine and tyramine. The degradation was assessed in vitro, both in presence of the BA and in presence of the specific chemical precursor and of producer bacteria. The two L. plantarum biotypes were found capable to work synergically. In addition, the survival in wine-like medium and the aptitude to degrade malic acid after alcoholic fermentation of the selected L. plantarum strains was analyzed. Our results suggest the potential application of wine L. plantarum strains to design malolactic starter cultures able to degrade BA in wine. PMID:22485114

  14. Circadian rhythmicity in the stimulation of bioluminescence by biogenic amines and MAO inhibitors in Gonyaulax polyedra

    NASA Astrophysics Data System (ADS)

    Balzer, Ivonne; Hardeland, Rüdiger

    1991-12-01

    In the dinoflagellate Gonyaulax polyedra bioluminescence was investigated in constant darkness. Light emission was stimulated considerably and specifically by the biogenic smines epinephrine, 5-methoxytryptamine, and kynuramine. Various analogues and motabolites of these substances, such as norepinephrine, isoproterenol, phenylephrine, synephrine, metanephrine isoproterenol, phenylephrine, synephrine, metanephrine dopamine, 3,4-dihydroxymandelic and 3-methoxy hydroxymandelic acids, serotonin, N-acetylserotonin, melatonin, 5-hydroxytryptophol, 5-methoxytryptophol, kynurenine, 4-hydroxyquinoline, 3-hydroxyanthrani ic, and quinolinic acids were much less effective. Strong enhancement of bioluminescence, in the range of those obtained with the three stimulatory biogenic amines was also observed after administration of several compeunds acting as MAO inhibitors in mammalian systems, in particular, pargyline, amitriptyline, p-benzoquinone, tranylcypromine, harmaline, and noreleagnine. The responsiveness of cells towards epinephrine, 5-methoxytryptamine, kynuramine, amitriptyline, p-benzoquinone, and noreleagnine varied considerably within the circadian cycle, with the highest stimulations obtained during subjective night. These rhythms can be only partially explained by periodic bioluminescence capacity, and seem to comprise a cyclicity in the sensitivity of cells to the compounds mentioned.

  15. Determination of biogenic amines by high-performance liquid chromatography (HPLC-DAD) in probiotic cow's and goat's fermented milks and acceptance

    PubMed Central

    Costa, Marion P; Balthazar, Celso F; Rodrigues, Bruna L; Lazaro, Cesar A; Silva, Adriana C O; Cruz, Adriano G; Conte Junior, Carlos A

    2015-01-01

    This study evaluated the presence of biogenic amines in fermented cow's and goat's milks containing probiotic bacteria, during the first 10 days of chilled storage (4 ± 2°C), when the probiotic strains are most viable. The overall acceptance of both fermented milks, produced using the same starter culture and probiotics, was tested. In both products, the initially high levels of tyramine (560 mg kg−1 means for both fermented milks), the predominant biogenic amine, increased during the storage period, which may be considered this amine as a quality index for fermented milks. The other principal biogenic amines (putrescine, cadaverine, histamine, and spermidine) were produced on days 1–5 of storage, and thereafter decreased. At the end of the 10th day, these amines, respectively, showed values of fermented cow's milk 20.26, 29.09, 17.97, and 82.07 mg kg−1; and values of fermented goat's milk 22.92, 29.09, 34.85, and 53.85 mg kg−1, in fermented cow's and goat's milk. Fermented cow's milk was well accepted compared to fermented goat's milk. The results suggested that the content of biogenic amines may be a criterion for selecting lactic acid bacteria used to produce fermented milks. PMID:25987991

  16. Inhibitory Effects of Spices on Biogenic Amine Accumulation during Fish Sauce Fermentation.

    PubMed

    Zhou, Xuxia; Qiu, Mengting; Zhao, Dandan; Lu, Fei; Ding, Yuting

    2016-04-01

    The presence of high levels of biogenic amines is detrimental to the quality and safety of fish sauce. This study investigated the effects of ethanol extracts of spices, including garlic, ginger, cinnamon, and star anise extracts, in reducing the accumulation of biogenic amines during fish sauce fermentation. The concentrations of biogenic amines, which include histamine, putrescine, tyramine, and spermidine, all increased during fish sauce fermentation. When compared with the samples without spices, the garlic and star anise extracts significantly reduced these increases. The greatest inhibitory effect was observed for the garlic ethanolic extracts. When compared with controls, the histamine, putrescine, tyramine, and spermidine contents and the overall biogenic amine levels of the garlic extract-treated samples were reduced by 30.49%, 17.65%, 26.03%, 37.20%, and 27.17%, respectively. The garlic, cinnamon, and star anise extracts showed significant inhibitory effects on aerobic bacteria counts. Furthermore, the garlic and star anise extracts showed antimicrobial activity against amine producers. These findings may be helpful for enhancing the safety of fish sauce.

  17. Inhibitory Effects of Spices on Biogenic Amine Accumulation during Fish Sauce Fermentation.

    PubMed

    Zhou, Xuxia; Qiu, Mengting; Zhao, Dandan; Lu, Fei; Ding, Yuting

    2016-04-01

    The presence of high levels of biogenic amines is detrimental to the quality and safety of fish sauce. This study investigated the effects of ethanol extracts of spices, including garlic, ginger, cinnamon, and star anise extracts, in reducing the accumulation of biogenic amines during fish sauce fermentation. The concentrations of biogenic amines, which include histamine, putrescine, tyramine, and spermidine, all increased during fish sauce fermentation. When compared with the samples without spices, the garlic and star anise extracts significantly reduced these increases. The greatest inhibitory effect was observed for the garlic ethanolic extracts. When compared with controls, the histamine, putrescine, tyramine, and spermidine contents and the overall biogenic amine levels of the garlic extract-treated samples were reduced by 30.49%, 17.65%, 26.03%, 37.20%, and 27.17%, respectively. The garlic, cinnamon, and star anise extracts showed significant inhibitory effects on aerobic bacteria counts. Furthermore, the garlic and star anise extracts showed antimicrobial activity against amine producers. These findings may be helpful for enhancing the safety of fish sauce. PMID:26953496

  18. Quality Changes and Biogenic Amines Accumulation of Black Carp (Mylopharyngodon piceus) Fillets Stored at Different Temperatures.

    PubMed

    Fan, Hongbing; Liu, Xiaochang; Hong, Hui; Shen, Song; Xu, Qian; Feng, Ligeng; Luo, Yongkang

    2016-04-01

    Postmortem quality changes of black carp (Mylopharyngodon piceus) fillets stored at 20, 4, and 0°C (in ice) were determined in terms of pH value, K value, total volatile basic nitrogen, free amino acids, biogenic amines, drip loss, electrical conductivity (EC), sensory score, and microbial growth. The results showed that black carp fillets could maintain a good quality for 2, 9, and 12 days when stored at 20, 4, and 0°C, respectively. Pseudomonads, Aeromonas, and Enterobacteriaceae were the main spoilage bacteria in black carp. Tryptamine, 2-phenylethylamine, putrescine, cadaverine, and tyramine increased significantly (P < 0.05) during storage at the three temperatures, but not spermidine and spermine, among which tyramine and putrescine were the main biogenic amines in black carp fillets. A significantly higher concentration of histamine (132.05 mg/kg on the third day) was detected in the samples stored at 20°C (P < 0.01) than at 4 and 0°C (0.62 to 3.28 mg/kg) throughout storage, indicating storage of samples at 20°C favored the formation of histamine. The accumulations of tyramine, cadaverine, and histamine were highly correlated with the productions of tyrosine, lysine, and histidine, respectively. Correlations between EC and sensory, physical, chemical, and microbial parameters at the three storage temperatures showed that EC could be used as a better quality indicator to assess the overall quality of fish stored at 4 and 0°C (low temperature) than at 20°C. PMID:27052869

  19. Structure, Function, and Evolution of Biogenic Amine-binding Proteins in Soft Ticks

    SciTech Connect

    Mans, Ben J.; Ribeiro, Jose M.C.; Andersen, John F.

    2008-08-19

    Two highly abundant lipocalins, monomine and monotonin, have been isolated from the salivary gland of the soft tick Argas monolakensis and shown to bind histamine and 5-hydroxytryptamine (5-HT), respectively. The crystal structures of monomine and a paralog of monotonin were determined in the presence of ligands to compare the determinants of ligand binding. Both the structures and binding measurements indicate that the proteins have a single binding site rather than the two sites previously described for the female-specific histamine-binding protein (FS-HBP), the histamine-binding lipocalin of the tick Rhipicephalus appendiculatus. The binding sites of monomine and monotonin are similar to the lower, low affinity site of FS-HBP. The interaction of the protein with the aliphatic amine group of the ligand is very similar for the all of the proteins, whereas specificity is determined by interactions with the aromatic portion of the ligand. Interestingly, protein interaction with the imidazole ring of histamine differs significantly between the low affinity binding site of FS-HBP and monomine, suggesting that histamine binding has evolved independently in the two lineages. From the conserved features of these proteins, a tick lipocalin biogenic amine-binding motif could be derived that was used to predict biogenic amine-binding function in other tick lipocalins. Heterologous expression of genes from salivary gland libraries led to the discovery of biogenic amine-binding proteins in soft (Ornithodoros) and hard (Ixodes) tick genera. The data generated were used to reconstruct the most probable evolutionary pathway for the evolution of biogenic amine-binding in tick lipocalins.

  20. Bacteria isolated from Korean black raspberry vinegar with low biogenic amine production in wine.

    PubMed

    Song, Nho-Eul; Cho, Hyoun-Suk; Baik, Sang-Ho

    2016-01-01

    A high concentration of histamine, one of the biogenic amines (BAs) usually found in fermented foods, can cause undesirable physiological side effects in sensitive humans. The objective of this study is to isolate indigenous Acetobacter strains from naturally fermented Bokbunja vinegar in Korea with reduced histamine production during starter fermentation. Further, we examined its physiological and biochemical properties, including BA synthesis. The obtained strain MBA-77, identified as Acetobacter aceti by 16S rDNA homology and biochemical analysis and named A. aceti MBA-77. A. aceti MBA-77 showed optimal acidity % production at pH 5; the optimal temperature was 25°C. When we prepared and examined the BAs synthesis spectrum during the fermentation process, Bokbunja wine fermented with Saccharomyces cerevisiae showed that the histamine concentration increased from 2.72 of Bokbunja extract to 5.29mg/L and cadaverine and dopamine was decreased to 2.6 and 10.12mg/L, respectively. Bokbunja vinegar prepared by A. aceti MBA-77 as the starter, the histamine concentration of the vinegar preparation step was decreased up to 3.66mg/L from 5.29mg/L in the wine preparation step. To our knowledge, this is the first report to demonstrate acetic acid bacteria isolated from Bokbunja seed vinegar with low spectrum BA and would be useful for wellbeing vinegar preparation.

  1. Effects of condensation products of biogenic amines on human platelet function

    SciTech Connect

    Given, M.B.

    1983-01-01

    Condensation products (CP) are formed by the reaction of biogenic amines with aldehydes and alpha-keto acids. The purpose of this investigation was to examine the effects of CP on platelet function in vitro. The effect of CP on platelet aggregation was examined. Epinephrine-induced aggregation was inhibited, suggesting CP antagonistic activity on the platelet alpha/sub 2/-adrenergic receptors. Adenosine-diphosphate (ADP), collagen and arachidonic acid induced aggregation was inhibited only at high concentrations. Inhibition of epinephrine and ADP aggregation was reversible, suggesting CP are competitive inhibitors of these agonists. Binding affinities for the platelet alpha/sub 2/-adrenergic receptor were determined using (/sup 3/H)-yohimbine, a specific alpha/sup 2/-receptor antagonist. The order of potency for CP inhibition of (/sup 3/H)-yohimbine binding paralleled that determined for inhibition of epinephrine-induced aggregation. Platelet uptake of serotonin (5-HT) was competitively inhibited by CP, with the exception of salsolinol, which appears to be stimulatory. Release of 5-HT from platelets was induced by CP, with betacarbolines being more potent than tetrahydroisoquinolines. Evidence suggests that CP cause release by displacement of 5-HT from intraplatelet storage sites since this effect can be inhibited by imipramine, thus preventing accumulation of CP by platelets.

  2. Bacteria isolated from Korean black raspberry vinegar with low biogenic amine production in wine.

    PubMed

    Song, Nho-Eul; Cho, Hyoun-Suk; Baik, Sang-Ho

    2016-01-01

    A high concentration of histamine, one of the biogenic amines (BAs) usually found in fermented foods, can cause undesirable physiological side effects in sensitive humans. The objective of this study is to isolate indigenous Acetobacter strains from naturally fermented Bokbunja vinegar in Korea with reduced histamine production during starter fermentation. Further, we examined its physiological and biochemical properties, including BA synthesis. The obtained strain MBA-77, identified as Acetobacter aceti by 16S rDNA homology and biochemical analysis and named A. aceti MBA-77. A. aceti MBA-77 showed optimal acidity % production at pH 5; the optimal temperature was 25°C. When we prepared and examined the BAs synthesis spectrum during the fermentation process, Bokbunja wine fermented with Saccharomyces cerevisiae showed that the histamine concentration increased from 2.72 of Bokbunja extract to 5.29mg/L and cadaverine and dopamine was decreased to 2.6 and 10.12mg/L, respectively. Bokbunja vinegar prepared by A. aceti MBA-77 as the starter, the histamine concentration of the vinegar preparation step was decreased up to 3.66mg/L from 5.29mg/L in the wine preparation step. To our knowledge, this is the first report to demonstrate acetic acid bacteria isolated from Bokbunja seed vinegar with low spectrum BA and would be useful for wellbeing vinegar preparation. PMID:26991285

  3. Biogenic Amine Degradation by Bacillus Species Isolated from Traditional Fermented Soybean Food and Detection of Decarboxylase-Related Genes.

    PubMed

    Eom, Jeong Seon; Seo, Bo Young; Choi, Hye Sun

    2015-09-01

    Biogenic amines in some food products present considerable toxicological risks as potential human carcinogens when consumed in excess concentrations. In this study, we investigated the degradation of the biogenic amines histamine and tyramine and the presence of genes encoding histidine and tyrosine decarboxylases and amine oxidase in Bacillus species isolated from fermented soybean food. No expression of histidine and tyrosine decarboxylase genes (hdc and tydc) were detected in the Bacillus species isolated (B. subtilis HJ0-6, B. subtilis D'J53-4, and B. idriensis RD13-10), although substantial levels of amine oxidase gene (yobN) expression were observed. We also found that the three selected strains, as non-biogenic amineproducing bacteria, were significantly able to degrade the biogenic amines histamine and tyramine. These results indicated that the selected Bacillus species could be used as a starter culture for the control of biogenic amine accumulation and degradation in food. Our study findings also provided the basis for the development of potential biological control agents against these biogenic amines for use in the food preservation and food safety sectors.

  4. Biogenic amine – surfactant interactions at the air-water interface.

    PubMed

    Penfold, J; Thomas, R K; Li, P X

    2015-07-01

    The strong interaction between polyamines and anionic surfactants results in pronounced adsorption at the air-water interface and can lead to the formation of layered surface structures. The transition from monolayer adsorption to more complex surface structures depends upon solution pH, and the structure and molecular weight of the polyamine. The effects of manipulating the polyamine molecular weight and structure on the adsorption of the anionic surfactant sodium dodecyl sulphate at the air-water interface are investigated using neutron reflectivity and surface tension, for the biogenic amines putrescine, spermidine and spermine. The results show how changing the number of amine groups and the spacing between the amine groups impacts upon the surface adsorption. At lower pH, 3-7, and for the higher molecular weight polyamines, spermidine and spermine, ordered multilayer structures are observed. For putrescine at all pH and for spermidine and spermine at high pH, monolayer adsorption with enhanced surfactant adsorption compared to the pure surfactant is observed. The data for the biogenic amines, when compared with similar data for the polyamines ethylenediamine, diethylenetriamine and triethylenetetramine, indicate that the spacing between amines groups is more optimal for the formation of ordered surface multilayer structures.

  5. [Automated pre-column derivatization with o-phthaldialdehyde (OPA)> A new RP-HPLC method for the determination of biogenic amines in food].

    PubMed

    Petridis, K D; Steinhart, H

    1995-09-01

    A simple, selective and highly sensitive HPLC method for the routine determination of the biogenic amines in food is presented. Sample preparation is based on a rapid amine extraction using 10% trichloroacetic acid and a cation exchange column for extract purification. For the RP-HPLC analysis OPA/2-mercaptoethanol is used for the pre-column derivatisation, followed by fluorescence detection (Ex 345 nm, Em 440 nm). The effects of several factors are discussed. A separation of 15 biogenic amines is achieved within 70 min. The recoveries for histamine, tyramine, putrescine, cadaverine, tryptamine and beta-phenylethylamine are higher than 95%. The detection limits lie between 0.1-0.5 pMol/injection (20 microliters), depending on the amine and a good linearity is achieved in the range from 0.5-500 pMol (r > 0.99). The method has been applied for the determination of biogenic amines in swiss cheese, salami, milk, beer and wine, the repeatability is very good.

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

    PubMed

    Sun, Xiuhua; Yang, Xiurong; Wang, Erkang

    2003-07-11

    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.

  7. Biogenic amine levels, reproduction and social dominance in the queenless ant Streblognathus peetersi

    NASA Astrophysics Data System (ADS)

    Cuvillier-Hot, Virginie; Lenoir, Alain

    2006-03-01

    Social harmony often relies on ritualised dominance interactions between society members, particularly in queenless ant societies, where colony members do not have developmentally predetermined castes but have to fight for their status in the reproductive and work hierarchy. In this behavioural plasticity, their social organisation resembles more that of vertebrates than that of the “classic” social insects. The present study investigates the neurochemistry of the queenless ant species, Streblognathus peetersi, to better understand the neural basis of the high behavioural plasticity observed in queenless ants. We report measurements of brain biogenic amines [octopamine, dopamine, serotonin] of S. peetersi ants; they reveal a new set of biogenic amine influences on social organisation with no common features with other “primitively organised societies” (bumble bees) and some common features with “highly eusocial” species (honey bees). This similarity to honey bees may either confirm the heritage of queenless species from their probably highly eusocial ancestors or highlight independent patterns of biogenic amine influences on the social organisation of these highly derived species.

  8. Occurrence of biogenic amines in beers produced with malted organic Emmer wheat (Triticum dicoccum).

    PubMed

    Mozzon, Massimo; Boselli, Emanuele; Obiedziński, Mieczysław W; Frega, Natale G

    2015-01-01

    Because several groups of microorganisms are able to decarboxylate amino acids, the presence of biogenic amines (BA) can be seen as an index of the microbiological quality of the brewing process. BAs were quantified for the first time in the intermediate products and craft beers produced with malted organic Emmer wheat (Triticum dicoccum) in a small size brewery in order to assess the possible presence of critical control points related to biological hazard in the brewing process. BA levels in beers produced exclusively from malted organic Emmer wheat were between 15.4 and 25.2 mg l(-1) in the samples of light beer (Lt) and between 8.9 and 15.3 mg l(-1) in double malt beers (DM) ready for consumption (the beers stored for 90 days at 1-2°C). Cadaverine and tyramine were the main BAs in the Lt and DM beers, respectively. Increased concentrations of BAs seemed to be more related to the heat treatment of the processing product during mashing and wort boiling, rather than to the fermentation process. Much lower concentrations were found in finished beers obtained from 50% malted organic Emmer wheat and 50% malted barley (up to 3.2 mg l(-1)) or from 30% malted Emmer wheat (up to 8.3 mg l(-1)). Thus, Emmer wheat malt can be a useful alternative to wheat and spelt for the production of beer with a limited content of BA, if the processing technology is kept under control.

  9. Cuticle Integrity and Biogenic Amine Synthesis in Caenorhabditis elegans Require the Cofactor Tetrahydrobiopterin (BH4)

    PubMed Central

    Loer, Curtis M.; Calvo, Ana C.; Watschinger, Katrin; Werner-Felmayer, Gabriele; O’Rourke, Delia; Stroud, Dave; Tong, Amy; Gotenstein, Jennifer R.; Chisholm, Andrew D.; Hodgkin, Jonathan; Werner, Ernst R.; Martinez, Aurora

    2015-01-01

    Tetrahydrobiopterin (BH4) is the natural cofactor of several enzymes widely distributed among eukaryotes, including aromatic amino acid hydroxylases (AAAHs), nitric oxide synthases (NOSs), and alkylglycerol monooxygenase (AGMO). We show here that the nematode Caenorhabditis elegans, which has three AAAH genes and one AGMO gene, contains BH4 and has genes that function in BH4 synthesis and regeneration. Knockout mutants for putative BH4 synthetic enzyme genes lack the predicted enzymatic activities, synthesize no BH4, and have indistinguishable behavioral and neurotransmitter phenotypes, including serotonin and dopamine deficiency. The BH4 regeneration enzymes are not required for steady-state levels of biogenic amines, but become rate limiting in conditions of reduced BH4 synthesis. BH4-deficient mutants also have a fragile cuticle and are generally hypersensitive to exogenous agents, a phenotype that is not due to AAAH deficiency, but rather to dysfunction in the lipid metabolic enzyme AGMO, which is expressed in the epidermis. Loss of AGMO or BH4 synthesis also specifically alters the sensitivity of C. elegans to bacterial pathogens, revealing a cuticular function for AGMO-dependent lipid metabolism in host–pathogen interactions. PMID:25808955

  10. Impact of biogenic amine molecular weight and structure on surfactant adsorption at the air-water interface.

    PubMed

    Penfold, Jeffrey; Thomas, Robert K; Li, Peixun

    2016-02-01

    The oligoamines, such as ethylenediamine to pentaethylenetetramine, and the aliphatic biogenic amines, such as putrescine, spermidine and spermine, strongly interact with anionic surfactants, such as sodium dodecylsulfate, SDS. It has been shown that this results in pronounced surfactant adsorption at the air-water interface and the transition from monolayer to multilayer adsorption which depends upon solution pH and oligoamine structure. In the neutron reflectivity, NR, and surface tension, ST, results presented here the role of the oligoamine structure on the adsorption of SDS is investigated more fully using a range of different biogenic amines. The effect of the extent of the intra-molecular spacing between amine groups on the adsorption has been extended by comparing results for cadavarine with putrescine and ethylenediamine. The impact of more complex biogenic amine structures on the adsorption has been investigated with the aromatic phenethylamine, and the heterocyclic amines histamine and melamine. The results provide an important insight into how surfactant adsorption at interfaces can be manipulated by the addition of biogenic amines, and into the role of solution pH and oligoamine structure in modifying the interaction between the surfactant and oligoamine. The results impact greatly upon potential applications and in understanding some of the important biological functions of biogenic amines.

  11. The role of brain biogenic amines in the control of pituitary-adrenocortical activity

    NASA Technical Reports Server (NTRS)

    Maickel, R. P.

    1975-01-01

    It was found that pretreatment of animals with desmethyl imipramine antagonized the reserpine-induced sedation without preventing the decline in brain amines or the hypersecretion of adrenocorticotropic hormone (ACTH). The antagonism of reserpine-induced ACTH hypersecretion by the monoamine oxidose (MAO) inhibitor pargyline (MO 911, N-methyl-N-benzyl-2-propynylamine) was studied. Evidence is presented that this antagonism is related to the level of brain biogenic amines maintained during the course of action of the drug. Pretreatment with MAO inhibitors does not affect the ACTH hypersecretion evoked by exposure to cold or chlorpromazine, lending further support to the hypothesis that reserpine-induced ACTH hypersecretion is related to brain amine changes.

  12. Grape yield to soil N-NO3- ratio can explain the different levels of biogenic amines in wine from two vineyards in the AOC Rioja (Spain)

    NASA Astrophysics Data System (ADS)

    Pérez-Álvarez, Eva Pilar; Garde-Cerdán, Teresa; Santamaría, Pilar; García-Escudero, Enrique; Peregrina, Fernando

    2014-05-01

    Plant N status may affect the grape amino acid concentration, which act as precursors in the formation of biogenic amines in wine. Biogenic amines have negative effects on human health and so they reduce the wine quality. The objective of this study was to analyze, at bloom (when the vine N demand peaks) if both the available soil N and the N concentration in the leaf could explain the amino acid concentration in the must as well as the biogenic amines in wines from AOC Rioja. Two plots with cv. Tempranillo (Vitis vinifera L.) vines grafted on R-110 rootstock were chosen: "La Grajera" (2,998 plants ha-1) and "Nájera" (2,849 plants ha-1), both plots with a traditional soil tillage management system and classified according to the American Soil Taxonomy as Typic Haloxerepts and Oxyaquic Xerorthent, respectively. Both soils had a pH higher than 7, a silty loam texture and organic matter values lower than 2%. The climatic conditions were described as semiarid Mediterranean according to the UNESCO aridity index. In each vineyard, three non-adjacent experimental plots with 3 rows of 30 vines each, were set out. No fertilizer was applied during the project. Each plot was sampled in 2009, 2010 and 2011 seasons at bloom, analyzing the available soil N-NO3- at 0-15 and 15-45 cm depth and expressing the results in kg ha-1 by means of the bulk density of soil and the coarse elements content. Also at bloom, 30 leaves per experimental plot were collected and their N concentration was analyzed. At harvest, 200 berries were taken from each plot and the amino acid content in the musts was determined by HPLC. In addition, 100 kg of grapes from each plot were taken in order to elaborate wine according to the AOC Rioja common winemaking practices. When the winemaking process was finished, the concentration of biogenic amines in the wine (histamine, methylamine, ethylamine, tyramine, putrescine, cadeverine, phenylethylamine and isoamylamine) was determined by HPLC. Our results showed

  13. Effect of added proteinases and level of starter culture on the formation of biogenic amines in raw milk Manchego cheese.

    PubMed

    Fernández-García, E; Tomillo, J; Núñez, M

    1999-11-15

    The influence of two proteinases (Bacillus subtilis neutral proteinase and Micrococcus sp. cysteine proteinase) and two starter culture levels (0.1% and 1%) on biogenic amine formation has been studied in raw ewes' milk Manchego cheese. Amino acid decarboxylating micro-organisms were determined on tyrosine enriched selective media. Biogenic amines were analysed by capillary electrophoresis in citrate buffer at pH 3.6. Addition of proteinases and level of starter culture did not influence the population of micro-organisms with amino acid decarboxylating activity, which represented on average 1% of the bacterial population in 30-day-old cheeses. Tyramine and histamine were detected in all batches of cheese from day 30. Concentrations of tyramine and histamine were higher in cheeses made from milk with neutral proteinase (up to 356 and 284 mg kg(-1), respectively, after 90 days) than in cheeses made from milk with cysteine proteinase (up to 269 and 189 mg kg(-1), respectively) or with no proteinase added (up to 305 and 226 mg kg(-1), respectively). Formation of tyramine and histamine was also favoured in cheeses made with 1% starter culture with respect to cheeses made with only 0.1% starter culture, probably due to the higher pH values of the former cheeses. After 90 days of ripening, concentrations of 10-20 mg kg(-1) phenylethylamine were observed in 9 of the 12 batches, and levels < 10 mg kg(-1) tryptamine were only detected in 3 batches, with no significant relationship between the concentration of these amines and proteinase addition or level of starter culture. PMID:10733250

  14. Structural basis for action by diverse antidepressants on biogenic amine transporters.

    PubMed

    Wang, Hui; Goehring, April; Wang, Kevin H; Penmatsa, Aravind; Ressler, Ryan; Gouaux, Eric

    2013-11-01

    The biogenic amine transporters (BATs) regulate endogenous neurotransmitter concentrations and are targets for a broad range of therapeutic agents including selective serotonin reuptake inhibitors (SSRIs), serotonin-noradrenaline reuptake inhibitors (SNRIs) and tricyclic antidepressants (TCAs). Because eukaryotic BATs are recalcitrant to crystallographic analysis, our understanding of the mechanism of these inhibitors and antidepressants is limited. LeuT is a bacterial homologue of BATs and has proven to be a valuable paradigm for understanding relationships between their structure and function. However, because only approximately 25% of the amino acid sequence of LeuT is in common with that of BATs, and as LeuT is a promiscuous amino acid transporter, it does not recapitulate the pharmacological properties of BATs. Indeed, SSRIs and TCAs bind in the extracellular vestibule of LeuT and act as non-competitive inhibitors of transport. By contrast, multiple studies demonstrate that both TCAs and SSRIs are competitive inhibitors for eukaryotic BATs and bind to the primary binding pocket. Here we engineered LeuT to harbour human BAT-like pharmacology by mutating key residues around the primary binding pocket. The final LeuBAT mutant binds the SSRI sertraline with a binding constant of 18 nM and displays high-affinity binding to a range of SSRIs, SNRIs and a TCA. We determined 12 crystal structures of LeuBAT in complex with four classes of antidepressants. The chemically diverse inhibitors have a remarkably similar mode of binding in which they straddle transmembrane helix (TM) 3, wedge between TM3/TM8 and TM1/TM6, and lock the transporter in a sodium- and chloride-bound outward-facing open conformation. Together, these studies define common and simple principles for the action of SSRIs, SNRIs and TCAs on BATs.

  15. Biogenic amines content in Spanish and French natural ciders: application of qPCR for quantitative detection of biogenic amine-producers.

    PubMed

    Ladero, Victor; Coton, Monika; Fernández, María; Buron, Nicolas; Martín, M Cruz; Guichard, Hugues; Coton, Emmanuel; Alvarez, Miguel A

    2011-05-01

    Biogenic amines (BA) are low molecular weight nitrogenous bases commonly found in fermented foods and beverages and their consumption can induce undesirable reactions. In this work, the BA content in natural cider from Spain and France was determined. Samples from commercially available cider or obtained during the elaboration process were analyzed. A different profile and BA concentration was observed depending on cider origin. qPCR tools developed for the quantitative detection of BA producers from cheese and wine were tested in the cider samples. A good connection between the BA content and the presence of BA-producing microorganisms was observed. Based on these tools, BA-producing bacteria were isolated from the analyzed cider samples, including new potential histamine- and putrescine-producing Lactobacillus paracollinoides strains. PMID:21356464

  16. Developmental expression analysis and immunolocalization of a biogenic amine receptor in Schistosoma mansoni.

    PubMed

    El-Shehabi, Fouad; Vermeire, Jon J; Yoshino, Timothy P; Ribeiro, Paula

    2009-05-01

    A Schistosoma mansoni G-protein coupled receptor (SmGPCR) was previously cloned and shown to be activated by the biogenic amine, histamine. Here we report a first investigation of the receptor's subunit organization, tissue distribution and expression levels in different stages of the parasite. A polyclonal antibody was produced in rabbits against the recombinant third intracellular loop (il3) of SmGPCR. Western blot studies of the native receptor and recombinant protein expressed in HEK293 cells showed that SmGPCR exists both as a monomer (65 kDa) and an apparent dimer of approximately 130 kDa These species were verified by immunoprecipitation of SmGPCR from S. mansoni extracts, using antibody that was covalently attached to agarose beads. Further investigation determined that the SmGPCR dimer was resistant to treatment with various detergents, 4 M urea and 0.1 M DTT but could be made to dissociate at acidic pH, suggesting the dimer is non-covalent in nature. Confocal immunofluorescence studies revealed significant SmGPCR immunoreactivity in sporocysts, schistosomula and adult worms but not miracidia. SmGPCR was found to be most widely expressed in the schistosomula, particularly the tegument, the subtegumental musculature and the acetabulum. In the adult stage we detected SmGPCR immunofluorescence mainly in the tubercles of male worms and, to a lesser extent, the body wall musculature. Localization in sporocysts was mainly confined to the tegument and cells within parenchymal matrices. A real-time quantitative reverse-transcription PCR analysis revealed that SmGPCR is upregulated at the mRNA level in the parasitic stages compared to the free-living miracidium and cercariae, and it is particularly elevated during early sporocyst and schistosomula development. The results identify SmGPCR as an important parasite receptor with potential functions in muscle and the tegument of S. mansoni. PMID:19545530

  17. Occurrence of biogenic amines in beers produced with malted organic Emmer wheat (Triticum dicoccum).

    PubMed

    Mozzon, Massimo; Boselli, Emanuele; Obiedziński, Mieczysław W; Frega, Natale G

    2015-01-01

    Because several groups of microorganisms are able to decarboxylate amino acids, the presence of biogenic amines (BA) can be seen as an index of the microbiological quality of the brewing process. BAs were quantified for the first time in the intermediate products and craft beers produced with malted organic Emmer wheat (Triticum dicoccum) in a small size brewery in order to assess the possible presence of critical control points related to biological hazard in the brewing process. BA levels in beers produced exclusively from malted organic Emmer wheat were between 15.4 and 25.2 mg l(-1) in the samples of light beer (Lt) and between 8.9 and 15.3 mg l(-1) in double malt beers (DM) ready for consumption (the beers stored for 90 days at 1-2°C). Cadaverine and tyramine were the main BAs in the Lt and DM beers, respectively. Increased concentrations of BAs seemed to be more related to the heat treatment of the processing product during mashing and wort boiling, rather than to the fermentation process. Much lower concentrations were found in finished beers obtained from 50% malted organic Emmer wheat and 50% malted barley (up to 3.2 mg l(-1)) or from 30% malted Emmer wheat (up to 8.3 mg l(-1)). Thus, Emmer wheat malt can be a useful alternative to wheat and spelt for the production of beer with a limited content of BA, if the processing technology is kept under control. PMID:25654207

  18. Developmental expression analysis and immunolocalization of a biogenic amine receptor in Schistosoma mansoni

    PubMed Central

    El-Shehabi, Fouad; Vermeire, Jon J.; Yoshino, Timothy P.; Ribeiro, Paula

    2013-01-01

    A Schistosoma mansoni G-protein coupled receptor (SmGPCR) was previously cloned and shown to be activated by the biogenic amine, histamine. Here we report a first investigation of the receptor’s subunit organization, tissue distribution and expression levels in different stages of the parasite. A polyclonal antibody was produced in rabbits against the recombinant third intracellular loop (il3) of SmGPCR. Western blot studies of the native receptor and recombinant protein expressed in HEK293 cells showed that SmGPCR exists both as a monomer (65 kDa) and an apparent dimer of ≈130 kDa These species were verified by immunoprecipitation of SmGPCR from S. mansoni extracts, using antibody that was covalently attached to agarose beads. Further investigation determined that the SmGPCR dimer was resistant to treatment with various detergents, 4 M urea and 0.1 M DTT but could be made to dissociate at acidic pH, suggesting the dimer is non-covalent in nature. Confocal immunofluorescence studies revealed significant SmGPCR immunoreactivity in sporocysts, schistosomula and adult worms but not miracidia. SmGPCR was found to be most widely expressed in the schistosomula, particularly the tegument, the subtegumental musculature and the acetabulum. In the adult stage we detected SmGPCR immunofluorescence mainly in the tubercles of male worms and, to a lesser extent, the body wall musculature. Localization in sporocysts was mainly confined to the tegument and cells within parenchymal matrices. A realtime quantitative reverse-transcription PCR analysis revealed that SmGPCR is upregulated at the mRNA level in the parasitic stages compared to the free-living miracidium and cercariae, and it is particularly elevated during early sporocyst and schistosomula development. The results identify SmGPCR as an important parasite receptor with potential functions in muscle and the tegument of S. mansoni. PMID:19545530

  19. Hypobaric hypoxia modulates brain biogenic amines and disturbs sleep architecture.

    PubMed

    Ray, Koushik; Dutta, Arkadeb; Panjwani, Usha; Thakur, Lalan; Anand, J P; Kumar, Sanjeev

    2011-01-01

    Sojourners to high altitude experience poor-quality of sleep due to hypobaric hypoxia (HH). Brain neurotransmitters are the key regulators of sleep wakefulness. Scientific literature has limited information on the role of brain neurotransmitters involved in sleep disturbance in HH. The present study aimed to investigate the time dependent changes in neurotransmitter levels and enzymes involved in the biosynthesis of brain neurotransmitters in frontal cortex, brain stem, cerebellum, pons and medulla and the effect of these alterations on sleep architecture in HH. Thirty adult Sprague-Dawley rats, body weight of 230-250 g were exposed to simulated altitude ∼7620 m, 282 mm Hg, partial pressure of O(2) 59 mm Hg for 7 and 14 days continuously in an animal decompression chamber. After 7 and 14 days of HH, brain nor-epinephrine and dopamine levels were significantly increased in frontal cortex, brain stem, cerebellum and pons and medulla whereas serotonin level was significantly reduced in frontal cortex and pons and medulla after 14 days of HH. Tyrosine hydroxylase level in locus coeruleus (LC) was significantly increased whereas Choline Acetyl Transferase and Glutamic Acid Decarboxylase (GAD) levels were significantly reduced in laterodorsal-tegmentum and pedunculopontine-tegmentum after 7 days of HH. GAD was also reduced in LC after 7 days HH. Alteration in these neurotransmitters and enzyme levels was accompanied with reduction in quality and quantity of sleep. There was a significant increase in sleep latency, rapid eye movement (REM) latency, duration of active awake, quiet awake, quiet sleep and a significant decrease in duration of REM sleep and deep sleep on day 7 and 14 of HH. It was concluded that HH alters the expression of enzymes linked to sleep neurotransmitter synthesis pathway and subsequent loss of homeostasis at neurotransmitter level disrupts the sleep pattern in hypobaric hypoxia.

  20. Concentrations of biogenic amines in fish, squid and octopus and their changes during storage.

    PubMed

    Hu, Yue; Huang, Zhiyong; Li, Jian; Yang, Hong

    2012-12-15

    The concentrations of seven biogenic amines (BA) were simultaneously determined in 74 samples of fish, squid and octopus, by the method of HPLC coupled with pre-column derivatisation. The relationship between the formation of BA in aquatic products and the growth of microbial flora during storage was also investigated. Results showed that putrescine, cadaverine, histamine and tyramine were the dominant BA in the studied samples, but the concentrations of histamine and tyramine were mostly less than 50 and 100 mgkg(-1), respectively. Freezing can effectively prevent the formation of BA, but the levels of putrescine, cadaverine, histamine and tyramine significantly increased (p<0.05) during storage at 4 and 25°C. The growth of mesophilic or psychrophilic bacteria in blue scad and octopus strongly and positively correlated with the formation of amines (such as putrescine, cadaverine, histamine and tyramine) during storage, except for histamine in octopus.

  1. Polyvinyl alcohol electrospun nanofibers containing Ag nanoparticles used as sensors for the detection of biogenic amines.

    PubMed

    Marega, Carla; Maculan, Jenny; Andrea Rizzi, Gian; Saini, Roberta; Cavaliere, Emanuele; Gavioli, Luca; Cattelan, Mattia; Giallongo, Giuseppe; Marigo, Antonio; Granozzi, Gaetano

    2015-02-20

    Polyvinyl alcohol (PVA) electrospun nanofibers containing Ag nanoparticles (NPs) have been deposited on glass substrates. The aim of the work was to test the feasibility of this approach for the detection of biogenic amines by using either the Ag localized surface plasmon resonance quenching caused by the adsorption of amines on Ag NPs or by detecting the amines by surface enhanced Raman spectroscopy (SERS) after adsorption, from the gas phase, on the metal NPs. Two different approaches have been adopted. In the first one an ethanol/water solution containing AgNO3 was used directly in the electrospinning apparatus. In this way, a simple heat treatment of the nanofibers mat was sufficient to obtain the formation of Ag NPs inside the nanofibers and a partial cross-link of PVA. In the second procedure, the Ag NPs were deposited on PVA nanofibers by using the supersonic cluster beam deposition method, so that a beam of pure Ag NPs of controlled size was obtained. Exposure of the PVA mat to the beam produced a uniform distribution of the NPs on the nanofibers surface. Ethylendiamine vapors and volatile amines released from fresh shrimp meat were chemisorbed on the nanofibers mats. A SERS spectrum characterized by a diagnostic Ag-N stretching vibration at 230 cm(-1) was obtained. The results allow to compare the two different approaches in the detection of ammines.

  2. Polyvinyl alcohol electrospun nanofibers containing Ag nanoparticles used as sensors for the detection of biogenic amines

    NASA Astrophysics Data System (ADS)

    Marega, Carla; Maculan, Jenny; Rizzi, Gian Andrea; Saini, Roberta; Cavaliere, Emanuele; Gavioli, Luca; Cattelan, Mattia; Giallongo, Giuseppe; Marigo, Antonio; Granozzi, Gaetano

    2015-02-01

    Polyvinyl alcohol (PVA) electrospun nanofibers containing Ag nanoparticles (NPs) have been deposited on glass substrates. The aim of the work was to test the feasibility of this approach for the detection of biogenic amines by using either the Ag localized surface plasmon resonance quenching caused by the adsorption of amines on Ag NPs or by detecting the amines by surface enhanced Raman spectroscopy (SERS) after adsorption, from the gas phase, on the metal NPs. Two different approaches have been adopted. In the first one an ethanol/water solution containing AgNO3 was used directly in the electrospinning apparatus. In this way, a simple heat treatment of the nanofibers mat was sufficient to obtain the formation of Ag NPs inside the nanofibers and a partial cross-link of PVA. In the second procedure, the Ag NPs were deposited on PVA nanofibers by using the supersonic cluster beam deposition method, so that a beam of pure Ag NPs of controlled size was obtained. Exposure of the PVA mat to the beam produced a uniform distribution of the NPs on the nanofibers surface. Ethylendiamine vapors and volatile amines released from fresh shrimp meat were chemisorbed on the nanofibers mats. A SERS spectrum characterized by a diagnostic Ag-N stretching vibration at 230 cm-1 was obtained. The results allow to compare the two different approaches in the detection of ammines.

  3. Isolation of compound and CNS depressant activities of Mikania scandens Willd with special emphasis to brain biogenic amines in mice.

    PubMed

    Pal, Dilipkumar; Mazumder, Upal Kanti

    2014-12-01

    Mikania scandens, a twining herb that grows as a weed in India and Bangladesh is used as vegetables and is a good source of vitamin A, C, B complex, mikanin, sesquiterpenes, betasitosterin, stigmasterol and friedelin. The present communication reports CNS depressant activities with special emphasis to brain biogenic amines in mice. Ethanol extract of leaves of M. scandens (EEMS) was prepared by Soxhalation and analyzed chemically. EEMS potentiated sleeping time induced by pentobarbitone, diazepam and meprobamate and showed significant reduction in the number of writhes and stretches. EEMS caused significant protection against pentylene tetrazole-induced convulsion and increased catecholamines and brain amino acids level significantly. Results showed that EEMS produced good CNS depressant effects in mice. PMID:25651612

  4. Anionic surfactant - Biogenic amine interactions: The role of surfactant headgroup geometry.

    PubMed

    Penfold, Jeffrey; Thomas, Robert K; Li, Peixun

    2016-03-15

    Oligoamines and biogenic amines (naturally occurring oligoamines) are small flexible polycations. They interact strongly with anionic surfactants such as sodium dodecyl sulfate, SDS. This results in enhanced adsorption and the formation of layered structures and the formation of layered structures at the air-water interface which depends on surfactant concentration and solution pH. The effect of changing the surfactant headgroup geometry on that interaction and subsequent adsorption is reported here. Neutron reflectivity, NR, results for the surface adsorption of the anionic surfactant sodium diethylene glycol monododecyl ether sulfate, SLES, with the biogenic amine, spermine, are presented, and contrasted with previous data for SDS/spermine mixtures. The enhancement in the adsorption of the surfactant at the air-water interface where monolayer adsorption occurs is similar for both surfactants. However the regions of surfactant concentration and solution pH where surface multilayer adsorption occurs is less extensive for the SLES/spermine mixtures, and occurs only at low pH. The results show how changing the headgroup geometry by the introduction of the ethylene oxide linker group between the alkyl chain and sulfate headgroup modifies the polyamine - surfactant interaction. The increased steric constraint from the polyethylene oxide group disrupts the conditions for surface multilayer formation at the higher pH values. This has important consequences for applications where the modification or manipulation of the surface properties are required. PMID:26724704

  5. Validation of a Fluorescence Sensor Microtiterplate for Biogenic Amines in Meat and Cheese.

    PubMed

    Khairy, Gasser M; Azab, Hassan A; El-Korashy, Sabry A; Steiner, Mark-Steven; Duerkop, Axel

    2016-09-01

    An optical sensor microtiterplate for quantitative analysis of the total content of biogenic amines (TAC) in meat and cheese was developed and validated for the first time. In the plate, a chameleon dye (Py-1) is embedded in a polymeric cocktail which is deposited on the bottom of the wells in a common microtiterplate. On reaction with biogenic amines (BAs), the fluorescence of Py-1 at 620 nm rapidly delivers a precise TAC. After 10 min incubation at 25 °C the determination of the TAC in various (real) samples is possible in high-throughput with a standard microplate reader. The optimized fluorescence method was validated for linearity, sensitivity, accuracy, precision (intraday and inter day repeatability) and recovery using histamine (HIS) as a representative BA. The sensor microtiterplate was successfully applied to quantitatively analyze the TAC in 10 real samples of cheese and meat obtained from various Egyptian markets. The TAC of these real samples obtained by the sensor microtiterplate was validated against the contents of BAs obtained by GC-MS at various times of storage. The data of the sensor microtiterplate agreed well with those of GC-MS. This demonstrates that the sensor microtiterplate is a reliable screening tool for the degradation status of food samples.

  6. Biogenic amine content, histamine-forming bacteria, and adulteration of pork in tuna sausage products.

    PubMed

    Kung, Hsien-Feng; Tsai, Yung-Hsiang; Chang, Shih-Chih; Hong, Tang-Yao

    2012-10-01

    Twenty-five tuna sausage products were purchased from retail markets in Taiwan. The rates of occurrence of biogenic amines, histamine-forming bacteria, and adulteration by pork and poultry were determined. The average content of various biogenic amines in all tested samples was less than 2.0 mg/100 g (<0.05 to 1.85 mg/100 g). Thirteen histamine-producing bacterial strains isolated from tested samples produced 12.1 to 1,261 ppm of histamine in Trypticase soy broth supplemented with 1.0% L-histidine. Among them, Raoultella ornithinolytica (one strain), Enterobacter aerogenes (one strain), and Staphylococcus pasteuri (two strains) were identified as prolific histamine formers. PCR assay revealed that the adulteration rates were 80% (20 of 25) and 4% (1 of 25) for pork and poultry, respectively, in tuna sausage. The fish species in the tuna sausage samples were identified as Thunnus albacares for 22 samples (88%), Thunnus alalunga for 1 sample (4%), and Thunnus thynnus for 1 sample (4%), whereas the remaining sample was identified as Makaira nigricans (blue marlin). PMID:23043830

  7. Succinylated Octopamine Ascarosides and a New Pathway of Biogenic Amine Metabolism in Caenorhabditis elegans*

    PubMed Central

    Artyukhin, Alexander B.; Yim, Joshua J.; Srinivasan, Jagan; Izrayelit, Yevgeniy; Bose, Neelanjan; von Reuss, Stephan H.; Jo, Yeara; Jordan, James M.; Baugh, L. Ryan; Cheong, Micheong; Sternberg, Paul W.; Avery, Leon; Schroeder, Frank C.

    2013-01-01

    The ascarosides, small-molecule signals derived from combinatorial assembly of primary metabolism-derived building blocks, play a central role in Caenorhabditis elegans biology and regulate many aspects of development and behavior in this model organism as well as in other nematodes. Using HPLC-MS/MS-based targeted metabolomics, we identified novel ascarosides incorporating a side chain derived from succinylation of the neurotransmitter octopamine. These compounds, named osas#2, osas#9, and osas#10, are produced predominantly by L1 larvae, where they serve as part of a dispersal signal, whereas these ascarosides are largely absent from the metabolomes of other life stages. Investigating the biogenesis of these octopamine-derived ascarosides, we found that succinylation represents a previously unrecognized pathway of biogenic amine metabolism. At physiological concentrations, the neurotransmitters serotonin, dopamine, and octopamine are converted to a large extent into the corresponding succinates, in addition to the previously described acetates. Chemically, bimodal deactivation of biogenic amines via acetylation and succinylation parallels posttranslational modification of proteins via acetylation and succinylation of l-lysine. Our results reveal a small-molecule connection between neurotransmitter signaling and interorganismal regulation of behavior and suggest that ascaroside biosynthesis is based in part on co-option of degradative biochemical pathways. PMID:23689506

  8. Poly(dimethylsiloxane) microchip for precolumn reaction and micellar electrokinetic chromatography of biogenic amines.

    PubMed

    Ro, Kyung Won; Lim, Kwanseop; Kim, Ho; Hahn, Jong Hoon

    2002-04-01

    We have demonstrated that precolumn derivatization and capillary electrophoresis separation on a poly(dimethylsiloxane) (PDMS) microchip can be realized as efficient as those on glass microchips. In an optimized condition of micellar electrokinetic chromatography (MEKC), using 25 mM sodium borate buffer (pH 10.0) with 25 mM sodium dodecyl sulfate (SDS) and 5% v/v methanol, the electroosmotic flow in an oxidized PDMS microchip is stabilized within 3% for days. By employing a fluorometric derivatization with o-phthaldialdehyde (OPA) in an optimally designed reaction chamber, four most important biogenic amines occurring in foods, histamine, tyramine, putrescine, and tryptamine, are quantitatively determined in less than 1 min at the levels applicable to real samples. The migration behaviors of anionic OPA-derivatized biogenic amines under the MEKC conditions are analyzed, and it has been found that under our separation conditions, the electrophoretic mobility of the SDS micelles is significantly greater than those of the anions in the aqueous phase. The channel manifold in a PDMS substrate is fabricated using replica molding against a thick photoresist, SU-8, pattern generated by photolithography. The plate with the microchannel pattern is strongly, irreversibly bonded to another PDMS plate by using a new bonding technique, which employs surface oxidation by corona discharge generated from a cheap, handy source, Tesla coil.

  9. Validation of a Fluorescence Sensor Microtiterplate for Biogenic Amines in Meat and Cheese.

    PubMed

    Khairy, Gasser M; Azab, Hassan A; El-Korashy, Sabry A; Steiner, Mark-Steven; Duerkop, Axel

    2016-09-01

    An optical sensor microtiterplate for quantitative analysis of the total content of biogenic amines (TAC) in meat and cheese was developed and validated for the first time. In the plate, a chameleon dye (Py-1) is embedded in a polymeric cocktail which is deposited on the bottom of the wells in a common microtiterplate. On reaction with biogenic amines (BAs), the fluorescence of Py-1 at 620 nm rapidly delivers a precise TAC. After 10 min incubation at 25 °C the determination of the TAC in various (real) samples is possible in high-throughput with a standard microplate reader. The optimized fluorescence method was validated for linearity, sensitivity, accuracy, precision (intraday and inter day repeatability) and recovery using histamine (HIS) as a representative BA. The sensor microtiterplate was successfully applied to quantitatively analyze the TAC in 10 real samples of cheese and meat obtained from various Egyptian markets. The TAC of these real samples obtained by the sensor microtiterplate was validated against the contents of BAs obtained by GC-MS at various times of storage. The data of the sensor microtiterplate agreed well with those of GC-MS. This demonstrates that the sensor microtiterplate is a reliable screening tool for the degradation status of food samples. PMID:27481500

  10. Queen regulates biogenic amine level and nestmate recognition in workers of the fire ant, Solenopsis invicta

    NASA Astrophysics Data System (ADS)

    Vander Meer, Robert K.; Preston, Catherine A.; Hefetz, Abraham

    2008-12-01

    Nestmate recognition is a critical element in social insect organization, providing a means to maintain territoriality and close the colony to parasites and predators. Ants detect the colony chemical label via their antennae and respond to the label mismatch of an intruder with aggressive behavior. In the fire ant, Solenopsis invicta, worker ability to recognize conspecific nonnestmates decreases if the colony queen is removed, such that they do not recognize conspecific nonnestmates as different. Here, we tested the hypothesis that the presence of the colony queen influences the concentration of octopamine, a neuromodulator, in worker ants, which in turn has an effect on nestmate recognition acuity in workers. We demonstrate that queenless workers exhibit reduced brain octopamine levels and reduced discriminatory acuteness; however, feeding queenless workers octopamine restored both. Dopamine levels are influenced by honeybee queen pheromones; however, levels of this biogenic amine were unchanged in our experiments. This is the first demonstration of a link between the presence of the colony queen, a worker biogenic amine, and conspecific nestmate recognition, a powerful expression of colony cohesion and territoriality.

  11. Queen regulates biogenic amine level and nestmate recognition in workers of the fire ant, Solenopsis invicta.

    PubMed

    Vander Meer, Robert K; Preston, Catherine A; Hefetz, Abraham

    2008-12-01

    Nestmate recognition is a critical element in social insect organization, providing a means to maintain territoriality and close the colony to parasites and predators. Ants detect the colony chemical label via their antennae and respond to the label mismatch of an intruder with aggressive behavior. In the fire ant, Solenopsis invicta, worker ability to recognize conspecific nonnestmates decreases if the colony queen is removed, such that they do not recognize conspecific nonnestmates as different. Here, we tested the hypothesis that the presence of the colony queen influences the concentration of octopamine, a neuromodulator, in worker ants, which in turn has an effect on nestmate recognition acuity in workers. We demonstrate that queenless workers exhibit reduced brain octopamine levels and reduced discriminatory acuteness; however, feeding queenless workers octopamine restored both. Dopamine levels are influenced by honeybee queen pheromones; however, levels of this biogenic amine were unchanged in our experiments. This is the first demonstration of a link between the presence of the colony queen, a worker biogenic amine, and conspecific nestmate recognition, a powerful expression of colony cohesion and territoriality. PMID:18704354

  12. Biogenic amine content, histamine-forming bacteria, and adulteration of pork in tuna sausage products.

    PubMed

    Kung, Hsien-Feng; Tsai, Yung-Hsiang; Chang, Shih-Chih; Hong, Tang-Yao

    2012-10-01

    Twenty-five tuna sausage products were purchased from retail markets in Taiwan. The rates of occurrence of biogenic amines, histamine-forming bacteria, and adulteration by pork and poultry were determined. The average content of various biogenic amines in all tested samples was less than 2.0 mg/100 g (<0.05 to 1.85 mg/100 g). Thirteen histamine-producing bacterial strains isolated from tested samples produced 12.1 to 1,261 ppm of histamine in Trypticase soy broth supplemented with 1.0% L-histidine. Among them, Raoultella ornithinolytica (one strain), Enterobacter aerogenes (one strain), and Staphylococcus pasteuri (two strains) were identified as prolific histamine formers. PCR assay revealed that the adulteration rates were 80% (20 of 25) and 4% (1 of 25) for pork and poultry, respectively, in tuna sausage. The fish species in the tuna sausage samples were identified as Thunnus albacares for 22 samples (88%), Thunnus alalunga for 1 sample (4%), and Thunnus thynnus for 1 sample (4%), whereas the remaining sample was identified as Makaira nigricans (blue marlin).

  13. Influence of various cooking methods on the concentrations of volatile N-nitrosamines and biogenic amines in dry-cured sausages.

    PubMed

    Li, Ling; Wang, Peng; Xu, Xinglian; Zhou, Guanghong

    2012-05-01

    N-nitrosamines, biogenic amines, and residual nitrites are harmful substances and are often present in cured meats. The effects of different cooking methods (boiling, pan-frying, deep-frying, and microwave) were investigated on their contents in dry-cured sausage. The various N-nitrosamines were isolated by a steam distillation method and analyzed by gas chromatography mass spectrometry (GC-MS). The biogenic amines were determined after extraction with perchloric acid as dansyl derivatives by high-performance liquid chromatography (HPLC) method. The results showed that initial dry-cured raw sausage contained 5.31 μg/kg of total N-nitrosamines. Cooking by deep-frying or pan-frying resulted in products having the highest (P < 0.05) contents, compared with boiling or microwave treatments, which were not different from the raw. Although frying increased the content of N-nitrosodimethylamine (NDMA), N-nitrosodiethylamine (NDEA), and N-nitrosopyrrolidine (NPYR), it decreased the contents of histamine and cadaverine. Boiling and microwave treatments decreased the total biogenic amines significantly (P < 0.05). Residual nitrite was significantly reduced by cooking treatments. The results suggest that boiling and microwave treatments were more suitable methods for cured meat.

  14. Adsorption of pesticidal compounds bearing a single carboxyl functional group and biogenic amines by humic fraction-immobilized silica gel.

    PubMed

    Chen, Cheng-Sheng; Chen, Shushi

    2013-04-17

    Fractions collected from humic acids under acidic and basic conditions were immobilized on silica gel and used as adsorbents for a variety of agricultural pesticide compounds bearing a single carboxyl functional group and biogenic amines in acetonitrile. Among these compounds examined under the same conditions, the percentage of adsorption varies considerably from 0 to almost 100%. The percentage is found to be highly related to the structure of the analyte and the type of functional group attached to it. The adsorption, better performed on adsorbent immobilized with the fraction collected under acidic conditions, is believed to result from the reversible interaction between the functional moieties of the analyte and humic acids (e.g., amino or carboxyl group of analyte vs carboxyl group of humic acids, etc.) as no adsorption is observed under the same conditions for analytes that are derivatives of alcohol, amide, and ester. Given the nature of the analyte, the time needed to reach the maximum percent of adsorption decreases as the amount of adsorbent is increased. Also, the longer the time that has elapsed, the higher the percentage of analyte adsorbed, thus indicating that the adsorption process is surface-oriented. Factors such as the acidic or basic origin of the additive in the liquid phase of the matrix also affect the percentage of analyte adsorbed. PMID:23521499

  15. The fight and flight responses of crickets depleted of biogenic amines.

    PubMed

    Stevenson, P A; Hofmann, H A; Schoch, K; Schildberger, K

    2000-05-01

    Aggressive and escape behaviors were analysed in crickets (Orthoptera) treated with either reserpine, a nonspecific depleter of biogenic amines, or the synthesis inhibitors alpha-methyltryptophan (AMTP) and alpha-methyl-p-tyrosine (AMT) to specifically deplete serotonin, respectively dopamine and octopamine. Standard immunocytochemical techniques were used to verify depletion from central nervous tissue, and determine the effective dosages. Reserpinized crickets became exceedingly lethargic and had severely depressed escape responses. However, they were still able to express all the major elements of the escalating sequences of stereotype motor performances that typifies normal aggressive behavior in the cricket. AMT and AMTP treatment had opposing influences on escape behavior, being enhanced by serotonin depletion, but depressed by dopamine/octopamine depletion. AMTP-induced serotonin depletion had no influence on aggressive or submissive behaviors. AMT-treated crickets could normally only be brought to fight by coaxing. Though capable of expressing aggressive behavior per se, agonistic encounters between AMT-treated crickets were shorter, and rarely involved actual physical interactions. Hence, although amines seem to have similar actions on escape behavior in insects and crustaceans, the aminergic control of aggression seems to be fundamentally different in these arthropods groups. We conclude that amines are not in principle required for the initiation and operation of the motor circuits underlying aggression in the cricket. However, octopamine and/or dopamine seem necessary for establishing a level of excitability sufficient for aggressive behavior to become overt in response to appropriate natural releasing stimuli.

  16. Evaluation of Biogenic Amines Levels, and Biochemical and Microbiological Characterization of Italian-type Salami Sold in Rio de Janeiro, Brazil

    PubMed Central

    dos Santos, Luiz Felipe Lopes; Mársico, Eliane Teixeira; Lázaro, César Aquiles; Teixeira, Rose; Doro, Laís

    2015-01-01

    The objective of the present study was to evaluate the levels of biogenic amines (cadaverine, putrescine, tyramine, histamine, spermidine and spermine) by high performance liquid chromatography (HPLC) and the physicochemical (moisture, lipids, proteins, pH, water activity and fixed mineral residue) and microbiological (lactic acid bacteria and aerobic heterotrophic mesophilic bacteria count) characteristics of six Italian-type salami brands sold in the city of Niteroi (Rio de Janeiro, Brazil). The salami showed lactic acid bacteria count from 5.7 to 8.6 CFU•mL-1, and heterotrophic mesophilic bacteria count from 5.8 to 8.7 CFU•mL-1. Three brands showed moisture contents above 35% and one brand had protein content below 25%. The mean values obtained for the amines were: 197.43, 143.29, 73.02, 4.52, 90.66 and 36.17 mg•kg-1 for tyramine, putrescine, cadaverine, spermidine, histamine, and spermine respectively. Two brands presented histamine contents above the legal limit established in 100 mg•kg-1. We concluded that the evaluated salami presented a wide variation in the count of the bacterial groups with a predominance of lactic acid bacteria. The moisture contents indicate insufficient drying before commercialization and protein content had values below the minimum limit determined by the Brazilian legislation. Finally, the levels of biogenic amines found could cause adverse reactions in susceptible consumers, depending of the amount and frequency of intake of these products. PMID:27800400

  17. Extraction of carboxylic acids by amine extractants

    SciTech Connect

    Tamada, Janet Ayako; King, C.J.

    1989-01-01

    This work examines the chemistry of solvent extraction by long-chain amines for recovery of carboxylic acids from dilute aqueous solution. Long-chain amines act as complexing agents with the acid, which facilitates distribution of the acid into the organic phase. The complexation is reversible, allowing for recovery of the acid from the organic phase and regeneration of the extractant. Batch extraction experiments were performed to study the complexation of acetic, lactic, succinic, malonic, fumaric, and maleic acids with Alamine 336, an aliphatic, tertiary amine extractant, dissolved in various diluents. Results were interpreted by a ''chemical'' model, in which stoichiometric ratios of acid and amine molecules are assumed to form complexes in the solvent phase. From fitting of the extraction data, the stoichiometry of complexes formed and the corresponding equilibrium constants were obtained. The results of the model were combined with infrared spectroscopic experiments and results of past studies to analyze the chemical interactions that are responsible for extraction behavior. The information from the equilibrium studies was used to develop guidelines for large-scale staged extraction and regeneration schemes. A novel scheme, in which the diluent composition is shifted between extraction and regeneration, was developed which could achieve both high solute recovery and high product concentration. 169 refs., 57 figs., 15 tabs.

  18. Flight initiation and maintenance deficits in flies with genetically altered biogenic amine levels.

    PubMed

    Brembs, Björn; Christiansen, Frauke; Pflüger, Hans Joachim; Duch, Carsten

    2007-10-10

    Insect flight is one of the fastest, most intense and most energy-demanding motor behaviors. It is modulated on multiple levels by the biogenic amine octopamine. Within the CNS, octopamine acts directly on the flight central pattern generator, and it affects motivational states. In the periphery, octopamine sensitizes sensory receptors, alters muscle contraction kinetics, and enhances flight muscle glycolysis. This study addresses the roles for octopamine and its precursor tyramine in flight behavior by genetic and pharmacological manipulation in Drosophila. Octopamine is not the natural signal for flight initiation because flies lacking octopamine [tyramine-beta-hydroxylase (TbetaH) null mutants] can fly. However, they show profound differences with respect to flight initiation and flight maintenance compared with wild-type controls. The morphology, kinematics, and development of the flight machinery are not impaired in TbetaH mutants because wing-beat frequencies and amplitudes, flight muscle structure, and overall dendritic structure of flight motoneurons are unaffected in TbetaH mutants. Accordingly, the flight behavior phenotypes can be rescued acutely in adult flies. Flight deficits are rescued by substituting octopamine but also by blocking the receptors for tyramine, which is enriched in TbetaH mutants. Conversely, ablating all neurons containing octopamine or tyramine phenocopies TbetaH mutants. Therefore, both octopamine and tyramine systems are simultaneously involved in regulating flight initiation and maintenance. Different sets of rescue experiments indicate different sites of action for both amines. These findings are consistent with a complex system of multiple amines orchestrating the control of motor behaviors on multiple levels rather than single amines eliciting single behaviors.

  19. Flight initiation and maintenance deficits in flies with genetically altered biogenic amine levels.

    PubMed

    Brembs, Björn; Christiansen, Frauke; Pflüger, Hans Joachim; Duch, Carsten

    2007-10-10

    Insect flight is one of the fastest, most intense and most energy-demanding motor behaviors. It is modulated on multiple levels by the biogenic amine octopamine. Within the CNS, octopamine acts directly on the flight central pattern generator, and it affects motivational states. In the periphery, octopamine sensitizes sensory receptors, alters muscle contraction kinetics, and enhances flight muscle glycolysis. This study addresses the roles for octopamine and its precursor tyramine in flight behavior by genetic and pharmacological manipulation in Drosophila. Octopamine is not the natural signal for flight initiation because flies lacking octopamine [tyramine-beta-hydroxylase (TbetaH) null mutants] can fly. However, they show profound differences with respect to flight initiation and flight maintenance compared with wild-type controls. The morphology, kinematics, and development of the flight machinery are not impaired in TbetaH mutants because wing-beat frequencies and amplitudes, flight muscle structure, and overall dendritic structure of flight motoneurons are unaffected in TbetaH mutants. Accordingly, the flight behavior phenotypes can be rescued acutely in adult flies. Flight deficits are rescued by substituting octopamine but also by blocking the receptors for tyramine, which is enriched in TbetaH mutants. Conversely, ablating all neurons containing octopamine or tyramine phenocopies TbetaH mutants. Therefore, both octopamine and tyramine systems are simultaneously involved in regulating flight initiation and maintenance. Different sets of rescue experiments indicate different sites of action for both amines. These findings are consistent with a complex system of multiple amines orchestrating the control of motor behaviors on multiple levels rather than single amines eliciting single behaviors. PMID:17928454

  20. Metabolites of Microbial Origin with an Impact on Health: Ochratoxin A and Biogenic Amines.

    PubMed

    Russo, Pasquale; Capozzi, Vittorio; Spano, Giuseppe; Corbo, Maria R; Sinigaglia, Milena; Bevilacqua, Antonio

    2016-01-01

    Safety and quality are significant challenges for food; namely, safety represents a big threat all over the world and is one of the most important goal to be achieved in both Western Society and Developing Countries. Wine safety mainly relies upon some metabolites and many of them are of microbial origin. The main goal of this review is a focus on two kinds of compounds (biogenic amines and mycotoxins, mainly Ochratoxin A) for their deleterious effects on health. For each class of compounds, we will focus on two different traits: (a) synthesis of the compounds in wine, with a brief description of the most important microorganisms and factors leading this phenomenon; (b) prevention and/or correction strategies and new trends. In addition, there is a focus on a recent predictive tool able to predict toxin contamination of grape, in order to perform some prevention approaches and achieve safe wine. PMID:27092133

  1. Aggression, impulsivity, plasma sex hormones, and biogenic amine turnover in a forensic population of rapists.

    PubMed

    Giotakos, Orestis; Markianos, Manolis; Vaidakis, Nikos; Christodoulou, George N

    2003-01-01

    The aim of the present study was to assess androgen plasma levels and biogenic amine metabolites in a sex-offender group as well as to investigate the relationship between the biological findings and the impulsive, aggressive, and suicidal profile of the offenders. Fifty-seven males convicted for rape and 25 normal males comprised the study sample. We found that although both testosterone levels and aggression-impulsivity scores were higher in the group of rapists, testosterone levels were not associated with the aggression and impulsivity scores. Nevertheless, aggression-impulsivity scores were clearly associated with luteinizing hormone levels. This association may indicate a hyperactive hypothalamic-pituitary-gonadal axis, possibly the result of a reduced serotonergic activity.

  2. Comparative analysis of the in vitro cytotoxicity of the dietary biogenic amines tyramine and histamine.

    PubMed

    Linares, Daniel M; del Rio, Beatriz; Redruello, Begoña; Ladero, Victor; Martin, M Cruz; Fernandez, Maria; Ruas-Madiedo, Patricia; Alvarez, Miguel A

    2016-04-15

    Tyramine and histamine, the most toxic biogenic amines (BA), are often found in high concentrations in certain foods. Prompted by the limited knowledge of BA toxicity, and increasing awareness of the risks associated with high intakes of dietary BA, the in vitro cytotoxicity of tyramine and histamine was investigated. Tyramine and histamine were toxic for HT29 intestinal cell cultures at concentrations commonly found in BA-rich food, as determined by real-time cell analysis. Surprisingly, tyramine had a stronger and more rapid cytotoxic effect than histamine. Their mode of action was also different, while tyramine caused cell necrosis, histamine induced apoptosis. To avoid health risks, the BA content of foods should be reduced and legal limits established for tyramine. PMID:26617000

  3. Metabolites of Microbial Origin with an Impact on Health: Ochratoxin A and Biogenic Amines

    PubMed Central

    Russo, Pasquale; Capozzi, Vittorio; Spano, Giuseppe; Corbo, Maria R.; Sinigaglia, Milena; Bevilacqua, Antonio

    2016-01-01

    Safety and quality are significant challenges for food; namely, safety represents a big threat all over the world and is one of the most important goal to be achieved in both Western Society and Developing Countries. Wine safety mainly relies upon some metabolites and many of them are of microbial origin. The main goal of this review is a focus on two kinds of compounds (biogenic amines and mycotoxins, mainly Ochratoxin A) for their deleterious effects on health. For each class of compounds, we will focus on two different traits: (a) synthesis of the compounds in wine, with a brief description of the most important microorganisms and factors leading this phenomenon; (b) prevention and/or correction strategies and new trends. In addition, there is a focus on a recent predictive tool able to predict toxin contamination of grape, in order to perform some prevention approaches and achieve safe wine. PMID:27092133

  4. Comparative analysis of the in vitro cytotoxicity of the dietary biogenic amines tyramine and histamine.

    PubMed

    Linares, Daniel M; del Rio, Beatriz; Redruello, Begoña; Ladero, Victor; Martin, M Cruz; Fernandez, Maria; Ruas-Madiedo, Patricia; Alvarez, Miguel A

    2016-04-15

    Tyramine and histamine, the most toxic biogenic amines (BA), are often found in high concentrations in certain foods. Prompted by the limited knowledge of BA toxicity, and increasing awareness of the risks associated with high intakes of dietary BA, the in vitro cytotoxicity of tyramine and histamine was investigated. Tyramine and histamine were toxic for HT29 intestinal cell cultures at concentrations commonly found in BA-rich food, as determined by real-time cell analysis. Surprisingly, tyramine had a stronger and more rapid cytotoxic effect than histamine. Their mode of action was also different, while tyramine caused cell necrosis, histamine induced apoptosis. To avoid health risks, the BA content of foods should be reduced and legal limits established for tyramine.

  5. A potential link among biogenic amines-based pesticides, learning and memory, and colony collapse disorder: a unique hypothesis.

    PubMed

    Farooqui, Tahira

    2013-01-01

    Pesticides are substances that have been widely used throughout the world to kill, repel, or control organisms such as certain forms of plants or animals considered as pests. Depending on their type, dose, and persistence in the environment, they can have impact even on non-target species such as beneficial insects (honeybees) in different ways, including reduction in their survival rate and interference with their reproduction process. Honeybee Apis mellifera is a major pollinator and has substantial economical and ecological values. Colony collapse disorder (CCD) is a mysterious phenomenon in which adult honeybee workers suddenly abandon from their hives, leaving behind food, brood, and queen. It is lately drawing a lot of attention due to pollination crisis as well as global agriculture and medical demands. If the problem of CCD is not resolved soon enough, this could have a major impact on food industry affecting world's economy a big time. Causes of CCD are not known. In this overview, I discuss CCD, biogenic amines-based-pesticides (neonicotinoids and formamidines), and their disruptive effects on biogenic amine signaling causing olfactory dysfunction in honeybees. According to my hypothesis, chronic exposure of biogenic amines-based-pesticides to honeybee foragers in hives and agricultural fields can disrupt neural cholinergic and octopaminergic signaling. Abnormality in biogenic amines-mediated neuronal signaling impairs their olfactory learning and memory, therefore foragers do not return to their hive - a possible cause of CCD. This overview is an attempt to discuss a hypothetical link among biogenic amines-based pesticides, olfactory learning and memory, and CCD.

  6. A potential link among biogenic amines-based pesticides, learning and memory, and colony collapse disorder: a unique hypothesis.

    PubMed

    Farooqui, Tahira

    2013-01-01

    Pesticides are substances that have been widely used throughout the world to kill, repel, or control organisms such as certain forms of plants or animals considered as pests. Depending on their type, dose, and persistence in the environment, they can have impact even on non-target species such as beneficial insects (honeybees) in different ways, including reduction in their survival rate and interference with their reproduction process. Honeybee Apis mellifera is a major pollinator and has substantial economical and ecological values. Colony collapse disorder (CCD) is a mysterious phenomenon in which adult honeybee workers suddenly abandon from their hives, leaving behind food, brood, and queen. It is lately drawing a lot of attention due to pollination crisis as well as global agriculture and medical demands. If the problem of CCD is not resolved soon enough, this could have a major impact on food industry affecting world's economy a big time. Causes of CCD are not known. In this overview, I discuss CCD, biogenic amines-based-pesticides (neonicotinoids and formamidines), and their disruptive effects on biogenic amine signaling causing olfactory dysfunction in honeybees. According to my hypothesis, chronic exposure of biogenic amines-based-pesticides to honeybee foragers in hives and agricultural fields can disrupt neural cholinergic and octopaminergic signaling. Abnormality in biogenic amines-mediated neuronal signaling impairs their olfactory learning and memory, therefore foragers do not return to their hive - a possible cause of CCD. This overview is an attempt to discuss a hypothetical link among biogenic amines-based pesticides, olfactory learning and memory, and CCD. PMID:23059446

  7. Analysis of biogenic amines in wines by salting-out assisted liquid-liquid extraction and high-performance liquid chromatography with fluorimetric detection.

    PubMed

    Ramos, Rui Miguel; Valente, Inês Maria; Rodrigues, José António

    2014-06-01

    Biogenic amines are nitrogenous organic compounds of low molecular weight that are either formed or metabolized in cells of living organisms and can be found in several food products, being produced mainly by amino acid decarboxylation. When ingested in high concentrations they can induce several health problems in humans. In alcoholic beverages, and especially in wine, they are formed during the vinification process as a result of the action of microorganisms. In this work it is proposed a new methodology for the determination of biogenic amines in wines, which includes a sample preparation approach based on salting-out assisted liquid-liquid extraction, the use of dansyl chloride for the derivatization and chromatographic separation by high-performance liquid chromatography with fluorimetric detection. The salting-out effect is used to promote phase separation between water and a water-miscible organic solvent, while improving the extraction of organic or inorganic species. Several extraction parameters were optimized, such as the dansyl chloride concentration, pH and the effects caused by the order in which the extraction and derivatization were performed. Extraction of amines, and consequent detection, depends on the presence of dansyl chloride in solution prior to extraction. The results showed the possibility to simultaneously perform the extraction and the derivatization, making sample preparation easier and less time-consuming. The methodology was successfully applied to the determination of biogenic amines in five wines (white, red and rosé). This method has the potential to be a good alternative to existing methods since it is cheaper, easier and simplifies the sample preparation step.

  8. Effect of hyperglycemia on biogenic amines, beta-endorphin and insulin of the rat brain.

    PubMed

    Kolta, M G; Williams, B B

    1984-12-01

    Three experiments were designed to study the changes in brain biogenic amines, beta-endorphin and insulin in response to hyperglycemia in adult male rats. In all three experiments, animals were decapitated 10 minutes post injection (IP) of either 2.5 ml of 40% glucose or 0.9% saline. In the first experiment brain DA, NE, 5-HT and 5-HIAA were measured using fluorometric method. Plasma glucose, insulin (RIA) and corticosterone (CPB) were also determined. In addition to these measurements, brain beta-endorphin was determined (RIA) in the second experiment and brain insulin (RIA) in the third experiment. In all three experiments the hyperglycemic groups showed a significant increase in plasma insulin, brain NE and 5-HT and a significant decrease in brain 5-HIAA and no significant change in plasma corticosterone, brain DA, beta-endorphin and insulin. The results obtained in these experiments suggest that high levels of glucose may have an inhibitory effect on the metabolism of NE and 5-HT resulting in increases in the level of both amines. They also suggest that brain insulin is independent of the pancreatic one since high blood glucose did not influence the central level.

  9. The Impact of Carvacrol on Ammonia and Biogenic Amine Production by Common Foodborne Pathogens.

    PubMed

    Özogul, Fatih; Kaçar, Çiğdem; Kuley, Esmeray

    2015-12-01

    The impact of carvacrol at different levels (0.1%, 0.5%, and 1%) on ammonia (AMN) and biogenic amines (BAs) production by 8 common foodborne pathogens (FBPs) (Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, Enterococcus faecalis, Pseudomonas aeruginosa, Listeria monocytogenes, Aeromonas hydrophila, and Salmonella Paratyphi A) was studied using a rapid high-performance liquid chromatography method. Significant differences among bacteria (P < 0.05) in AMN and BA production were observed using a tyrosine decarboxylase broth. Tyramine, dopamine, agmatine, spermine, and putrescine were the main amines produced by the bacteria. Tyramine production by P. aeruginosa was the highest (967 mg/L), whereas K. pneumoniae was the poorest tyramine producer (6.42 mg/L). AMN and BA production varied significantly depending on carvacrol levels and the specific bacterial strains. Tyramine production for all bacterial strains was significantly suppressed by addition of carvacrol at levels of 0.5% and 1%, but not 0.1%. Consequently, the effect of carvacrol on BA and AMN formation by FBP was dependent on bacterial strain as well as carvacrol level. PMID:26580308

  10. Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes

    PubMed Central

    Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.

    2014-01-01

    Rationale Synthetic hallucinogenic tryptamines, especially those originally described by Alexander Shulgin, continue to be abused in the United States. The range of subjective experiences produced by different tryptamines suggests that multiple neurochemical mechanisms are involved in their actions, in addition to the established role of agonist activity at serotonin-2A (5-HT2A) receptors. Objectives This study evaluated the interaction of a series of synthetic tryptamines with biogenic amine neurotransmitter transporters and with serotonin (5-HT) receptor subtypes implicated in psychedelic effects. Methods Neurotransmitter transporter activity was determined in rat brain synaptosomes. Receptor activity was determined using calcium mobilization and DiscoveRx PathHunter® assays in HEK293, Gα16-CHO, and CHOk1 cells transfected with human receptors. Results Twenty-one tryptamines were analyzed in transporter uptake and release assays, and 5-HT2A, serotonin 1A (5-HT1A), and 5-HT2A β-arrestin functional assays. Eight of the compounds were found to have 5-HT-releasing activity. Thirteen compounds were found to be 5-HT uptake inhibitors or were inactive. All tryptamines were 5-HT2A agonists with a range of potencies and efficacies, but only a few compounds were 5-HT1A agonists. Most tryptamines recruited β-arrestin through 5-HT2A activation. Conclusions All psychoactive tryptamines are 5-HT2A agonists, but 5-HT transporter (SERT) activity may contribute significantly to the pharmacology of certain compounds. The in vitro transporter data confirm structure-activity trends for releasers and uptake inhibitors whereby releasers tend to be structurally smaller compounds. Interestingly, two tertiary amines were found to be selective substrates at SERT, which dispels the notion that 5-HT-releasing activity is limited only to primary or secondary amines. PMID:24800892

  11. 40 CFR 721.6140 - Dialkyldithiophosphoric acid, aliphatic amine salt.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ..., aliphatic amine salt. 721.6140 Section 721.6140 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.6140 Dialkyldithiophosphoric acid, aliphatic amine salt. (a) Chemical... as a dialkyldithiophosphoric acid, aliphatic amine salt (P-90-1839) is subject to reporting...

  12. 40 CFR 721.6140 - Dialkyldithiophosphoric acid, aliphatic amine salt.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ..., aliphatic amine salt. 721.6140 Section 721.6140 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.6140 Dialkyldithiophosphoric acid, aliphatic amine salt. (a) Chemical... as a dialkyldithiophosphoric acid, aliphatic amine salt (P-90-1839) is subject to reporting...

  13. 40 CFR 721.6140 - Dialkyldithiophosphoric acid, aliphatic amine salt.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ..., aliphatic amine salt. 721.6140 Section 721.6140 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.6140 Dialkyldithiophosphoric acid, aliphatic amine salt. (a) Chemical... as a dialkyldithiophosphoric acid, aliphatic amine salt (P-90-1839) is subject to reporting...

  14. 40 CFR 721.6140 - Dialkyldithiophosphoric acid, aliphatic amine salt.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ..., aliphatic amine salt. 721.6140 Section 721.6140 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.6140 Dialkyldithiophosphoric acid, aliphatic amine salt. (a) Chemical... as a dialkyldithiophosphoric acid, aliphatic amine salt (P-90-1839) is subject to reporting...

  15. 40 CFR 721.6140 - Dialkyldithiophosphoric acid, aliphatic amine salt.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ..., aliphatic amine salt. 721.6140 Section 721.6140 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.6140 Dialkyldithiophosphoric acid, aliphatic amine salt. (a) Chemical... as a dialkyldithiophosphoric acid, aliphatic amine salt (P-90-1839) is subject to reporting...

  16. Heterogeneous uptake of amines by citric acid and humic acid.

    PubMed

    Liu, Yongchun; Ma, Qingxin; He, Hong

    2012-10-16

    Heterogeneous uptake of methylamine (MA), dimethylamine (DMA), and trimethylamine (TMA) onto citric acid and humic acid was investigated using a Knudsen cell reactor coupled to a quadrupole mass spectrometer at 298 K. Acid-base reactions between amines and carboxylic acids were confirmed. The observed uptake coefficients of MA, DMA, and TMA on citric acid at 298 K were measured to be 7.31 ± 1.13 × 10(-3), 6.65 ± 0.49 × 10(-3), and 5.82 ± 0.68 × 10(-3), respectively, and showed independence of sample mass. The observed uptake coefficients of MA, DMA, and TMA on humic acid at 298 K increased linearly with sample mass, and the true uptake coefficients of MA, DMA, and TMA were measured to be 1.26 ± 0.07 × 10(-5), 7.33 ± 0.40 × 10(-6), and 4.75 ± 0.15 × 10(-6), respectively. Citric acid, having stronger acidity, showed a higher reactivity than humic acid for a given amine; while the steric effect of amines was found to govern the reactivity between amines and citric acid or humic acid.

  17. Application of tea polyphenols in combination with 6-gingerol on shrimp paste of during storage: biogenic amines formation and quality determination.

    PubMed

    Cai, Luyun; Liu, Shucheng; Sun, Lijun; Wang, Yaling; Ji, Hongwu; Li, Jianrong

    2015-01-01

    Tea polyphenols (TP) have shown antioxidant activity and antimicrobial properties in the food industry. Assessment of anti-oxidation potential of 6-gingerol (GR) has also been verified. As little is known about the use of tea polyphenols either individually or in combination with 6-gingerol in shrimp paste, we aimed to investigate the effect of tea polyphenols combined with 6-gingerol on the biogenic amines inhibition and quality of shrimp paste stored at 25°C for 160 days. The shrimp paste samples were assigned into four groups: (1) control; (2) tea polyphenols treatment (0.3%); (3) 6-gingerol treatment (0.3%); (4) tea polyphenols (0.15%) + 6-gingerol (0.15%). Samples with no addition were used as control. The results indicate that treatment with tea polyphenols + 6-gingerol (TPGR) maintained paste appearance, inhibited oxidation of protein and lipids, and reduced microorganism counts compared to control treatment. The efficiency was superior to that of tea polyphenols or 6-gingerol treatment. Furthermore, shrimp paste treated with TPGR also exhibited significantly higher inhibition of biogenic amines. Total amino acids determination proved the efficacy of TPGR by maintaining the more amino acids of shrimp paste during ambient temperature storage. Our study suggests that TPGR might be a promising candidate for fermented foods due to its synergistic effect to maintain products quality and extending their shelf-life.

  18. Application of tea polyphenols in combination with 6-gingerol on shrimp paste of during storage: biogenic amines formation and quality determination

    PubMed Central

    Cai, Luyun; Liu, Shucheng; Sun, Lijun; Wang, Yaling; Ji, Hongwu; Li, Jianrong

    2015-01-01

    Tea polyphenols (TP) have shown antioxidant activity and antimicrobial properties in the food industry. Assessment of anti-oxidation potential of 6-gingerol (GR) has also been verified. As little is known about the use of tea polyphenols either individually or in combination with 6-gingerol in shrimp paste, we aimed to investigate the effect of tea polyphenols combined with 6-gingerol on the biogenic amines inhibition and quality of shrimp paste stored at 25°C for 160 days. The shrimp paste samples were assigned into four groups: (1) control; (2) tea polyphenols treatment (0.3%); (3) 6-gingerol treatment (0.3%); (4) tea polyphenols (0.15%) + 6-gingerol (0.15%). Samples with no addition were used as control. The results indicate that treatment with tea polyphenols + 6-gingerol (TPGR) maintained paste appearance, inhibited oxidation of protein and lipids, and reduced microorganism counts compared to control treatment. The efficiency was superior to that of tea polyphenols or 6-gingerol treatment. Furthermore, shrimp paste treated with TPGR also exhibited significantly higher inhibition of biogenic amines. Total amino acids determination proved the efficacy of TPGR by maintaining the more amino acids of shrimp paste during ambient temperature storage. Our study suggests that TPGR might be a promising candidate for fermented foods due to its synergistic effect to maintain products quality and extending their shelf-life. PMID:26441911

  19. Biogenic amine formation and nitrite reactions in meat batter as affected by high-pressure processing and chilled storage.

    PubMed

    Ruiz-Capillas, C; Aller-Guiote, P; Carballo, J; Colmenero, F Jiménez

    2006-12-27

    Changes in biogenic amine formation and nitrite depletion in meat batters as affected by pressure-temperature combinations (300 MPa/30 min/7, 20, and 40 degrees C), cooking process (70 degrees C/30 min), and storage (54 days/2 degrees C) were studied. Changes in residual nitrite concentration in raw meat batters were conditioned by the temperature and not by the pressure applied. Cooking process decreased (P < 0.05) the residual nitrite concentration in all samples. High-pressure processing and cooking treatment increased (P < 0.05) the nitrate content. Whereas protein-bound nitrite concentration decreased with pressure processing, no effect was observed with the heating process of meat batters. High-pressure processing conditions had no effect on the rate of residual nitrite loss throughout the storage. The application of high pressure decreased (P < 0.05) the concentration of some biogenic amines (tyramine, agmatine, and spermine). Irrespective of the high processing conditions, generally, throughout storage biogenic amine levels did not change or increased, although quantitatively this effect was not very important.

  20. Binding to extracellular matrix proteins and formation of biogenic amines by food-associated coagulase-negative staphylococci.

    PubMed

    Seitter, Marion; Geng, Bettina; Hertel, Christian

    2011-02-28

    In connection with a study on the DNA microarray based detection of genes involved in safety and technologically relevant properties (Seitter (née Resch) et al., 2011), food-associated coagulase-negative staphylococci (CNS) were investigated phenotypically with regard to their ability to bind to the extracellular matrix proteins (ECM) and to produce biogenic amines. The properties have been shown to be involved in the colonization of injured tissue and invasion into host cells as well as in pharmacologic effects on humans, respectively. The CNS exhibited a low, but nevertheless clearly measurable ECM binding capacity, except for strains of Staphylococcus equorum and Staphylococcus succinus, which show a comparable or even higher binding to fibrinogen and fibronectin than that of the control strain Staphylococcus aureus Cowan. Formation of biogenic amines could be often detected in S. carnosus, S. condimenti and S. strains, but rarely in S. equorum and not in S. succinus and S. xylosus strains. Mostly, 2-phenylethylamine, tyramine and tryptamine were formed by resting cells in amounts < 25 mg/l, whereas growing cells formed high amounts (> 100 mg/l) of 2-phenylethylamine and putrescine. This study confirmed the need of consideration of ECM binding and biogenic amine formation in the safety assessment of CNS used in the production of fermented foods.

  1. In situ derivatization hollow fibre liquid-phase microextraction for the determination of biogenic amines in food samples.

    PubMed

    Saaid, Mardiana; Saad, Bahruddin; Ali, Abdussalam Salhin Mohamed; Saleh, Muhammad Idiris; Basheer, Chanbasha; Lee, Hian Kee

    2009-07-01

    Hollow fibre liquid-phase microextraction with in situ derivatization using dansyl chloride has been successfully developed for the high-performance liquid chromatography-ultraviolet (HPLC-UV) determination of the biogenic amines (tryptamine, putrescine, cadaverine, histamine, tyramine, spermidine) in food samples. Parameters affecting the performance of the in situ derivatization process such as type of extraction solvent, temperature, extraction time, stirring speed and salt addition were studied and optimized. Under the optimized conditions (extraction solvent, dihexyl ether; acceptor phase, 0.1M HCl; extraction time, 30 min; extraction temperature, 26 degrees C; without addition of salt), enrichment factors varying from 47 to 456 were achieved. Good linearity of the analytes was obtained over a concentration range of 0.1-5 microg mL(-1) (with correlation coefficients of 0.9901-0.9974). The limits of detection and quantification based on a signal-to-noise ratio of 3-10, ranged from 0.0075 to 0.030 microg mL(-1) and 0.03 to 0.10 microg mL(-1), respectively. The relative standard deviations based on the peak areas for six replicate analysis of water spiked with 0.5 microg mL(-1) of each biogenic amine were lower than 7.5%. The method was successfully applied to shrimp sauce and tomato ketchup samples, offering an interesting alternative to liquid-liquid extraction and solid phase extraction for the analysis of biogenic amines in food samples. PMID:19481215

  2. Biofilm-Forming Capacity in Biogenic Amine-Producing Bacteria Isolated from Dairy Products.

    PubMed

    Diaz, Maria; Ladero, Victor; Del Rio, Beatriz; Redruello, Begoña; Fernández, María; Martin, M Cruz; Alvarez, Miguel A

    2016-01-01

    Biofilms on the surface of food industry equipment are reservoirs of potentially food-contaminating bacteria-both spoilage and pathogenic. However, the capacity of biogenic amine (BA)-producers to form biofilms has remained largely unexamined. BAs are low molecular weight, biologically active compounds that in food can reach concentrations high enough to be a toxicological hazard. Fermented foods, especially some types of cheese, accumulate the highest BA concentrations of all. The present work examines the biofilm-forming capacity of 56 BA-producing strains belonging to three genera and 10 species (12 Enterococcus faecalis, 6 Enterococcus faecium, 6 Enterococcus durans, 1 Enterococcus hirae, 12 Lactococcus lactis, 7 Lactobacillus vaginalis, 2 Lactobacillus curvatus, 2 Lactobacillus brevis, 1 Lactobacillus reuteri, and 7 Lactobacillus parabuchneri), all isolated from dairy products. Strains of all the tested species - except for L. vaginalis-were able to produce biofilms on polystyrene and adhered to stainless steel. However, the biomass produced in biofilms was strain-dependent. These results suggest that biofilms may provide a route via which fermented foods can become contaminated by BA-producing microorganisms. PMID:27242675

  3. Biogenic amines and the effect of short term lithium administration on open field activity in rats.

    PubMed

    Smith, D F

    1975-01-01

    Experiments were performed to examine whether the effects of short-term lithium administration on cerebral biogenic amine metabolism might be related to its action on open field activity. Rats received intragastric injections of lithium chloride (1.5 mEq/kg) twice daily for 5 days. This lead to a decrease in exploratory behavior in the open field. Administration of imipramine, which blocks the efffects of short-term lithium administration on norepinephrine turnover and uptake in the brain, failed to influence the effect of lithium on exploratory activity. Parachlorophenylalanine, which inhibits cerebral serotonin synthesis and depletes brain catecholamines, prevented the behavioral effect of lithium. Injection of pargyline, which inhibits cerebral monoamine oxidase activity, counteracted the effect of lithium on exploratory behavior and also influenced the emotionality of the animals in the open field. The findings are consistent with the hypothesis that cerebral monoamine levels and monoamine oxidase activity play a role in the effect of short-term lithium administration on open field activity in rats.

  4. Vaginal biogenic amines: biomarkers of bacterial vaginosis or precursors to vaginal dysbiosis?

    PubMed Central

    Nelson, Tiffanie M.; Borgogna, Joanna-Lynn C.; Brotman, Rebecca M.; Ravel, Jacques; Walk, Seth T.; Yeoman, Carl J.

    2015-01-01

    Bacterial vaginosis (BV) is the most common vaginal disorder among reproductive age women. One clinical indicator of BV is a “fishy” odor. This odor has been associated with increases in several biogenic amines (BAs) that may serve as important biomarkers. Within the vagina, BA production has been linked to various vaginal taxa, yet their genetic capability to synthesize BAs is unknown. Using a bioinformatics approach, we show that relatively few vaginal taxa are predicted to be capable of producing BAs. Many of these taxa (Dialister, Prevotella, Parvimonas, Megasphaera, Peptostreptococcus, and Veillonella spp.) are more abundant in the vaginal microbial community state type (CST) IV, which is depleted in lactobacilli. Several of the major Lactobacillus species (L. crispatus, L. jensenii, and L. gasseri) were identified as possessing gene sequences for proteins predicted to be capable of putrescine production. Finally, we show in a small cross sectional study of 37 women that the BAs putrescine, cadaverine and tyramine are significantly higher in CST IV over CSTs I and III. These data support the hypothesis that BA production is conducted by few vaginal taxa and may be important to the outgrowth of BV-associated (vaginal dysbiosis) vaginal bacteria. PMID:26483694

  5. Biogenic amines and collective organization in a superorganism: neuromodulation of social behavior in ants.

    PubMed

    Kamhi, J Frances; Traniello, James F A

    2013-01-01

    The ecological dominance of ants has to a great extent been achieved through their collective action and complex social organization. Ants provide diverse model systems to examine the neural underpinnings of individual behavior and group action that contribute to their evolutionary success. Core elements of ant colony structure such as reproductive and ergonomic division of labor, task specialization, and social integration are beginning to be understood in terms of cellular neuroanatomy and neurochemistry. In this review we discuss the neuroethology of colony organization by focusing on the role of biogenic amines in the control of social behavior in ants. We examine the role of neuromodulation in significant sociobiological characteristics of ants, including reproductive hierarchies, colony foundation, social food flow, nestmate recognition, territoriality, and size- and age-related sensory perception and task performance as well as the involvement of monoamines in collective intelligence, the ultimate key to the global dominance of these remarkable superorganisms. We conclude by suggesting future directions for the analysis of the aminergic regulation of behavior and social complexity in ants. PMID:24281765

  6. Methods of biological fluids sample preparation - biogenic amines, methylxanthines, water-soluble vitamins.

    PubMed

    Płonka, Joanna

    2015-01-01

    In recent years demands on the amount of information that can be obtained from the analysis of a single sample have increased. For time and economic reasons it is necessary to examine at the same time larger number of compounds, and compounds from different groups. This can best be seen in such areas as clinical analysis. In many diseases, the best results for patients are obtained when treatment fits the individual characteristics of the patient. Dosage monitoring is important at the beginning of therapy and in the full process of treatment. In the treatment of many diseases biogenic amines (dopamine, serotonin) and methylxanthines (theophylline, theobromine, caffeine) play an important role. They are used as drugs separately or in combination with others to support and strengthen the action of other drugs - for example, the combination of caffeine and paracetamol. Vitamin supplementation may be also an integral part of the treatment process. Specification of complete sample preparation parameters for extraction of the above compounds from biological matrices has been reviewed. Particular attention was given to the preparation stage and extraction methods. This review provides universal guidance on establishing a common procedures across laboratories to facilitate the preparation and analysis of all discussed compounds. PMID:25381720

  7. Biofilm-Forming Capacity in Biogenic Amine-Producing Bacteria Isolated from Dairy Products

    PubMed Central

    Diaz, Maria; Ladero, Victor; del Rio, Beatriz; Redruello, Begoña; Fernández, María; Martin, M. Cruz; Alvarez, Miguel A.

    2016-01-01

    Biofilms on the surface of food industry equipment are reservoirs of potentially food-contaminating bacteria—both spoilage and pathogenic. However, the capacity of biogenic amine (BA)-producers to form biofilms has remained largely unexamined. BAs are low molecular weight, biologically active compounds that in food can reach concentrations high enough to be a toxicological hazard. Fermented foods, especially some types of cheese, accumulate the highest BA concentrations of all. The present work examines the biofilm-forming capacity of 56 BA-producing strains belonging to three genera and 10 species (12 Enterococcus faecalis, 6 Enterococcus faecium, 6 Enterococcus durans, 1 Enterococcus hirae, 12 Lactococcus lactis, 7 Lactobacillus vaginalis, 2 Lactobacillus curvatus, 2 Lactobacillus brevis, 1 Lactobacillus reuteri, and 7 Lactobacillus parabuchneri), all isolated from dairy products. Strains of all the tested species - except for L. vaginalis—were able to produce biofilms on polystyrene and adhered to stainless steel. However, the biomass produced in biofilms was strain-dependent. These results suggest that biofilms may provide a route via which fermented foods can become contaminated by BA-producing microorganisms. PMID:27242675

  8. Biofilm-Forming Capacity in Biogenic Amine-Producing Bacteria Isolated from Dairy Products.

    PubMed

    Diaz, Maria; Ladero, Victor; Del Rio, Beatriz; Redruello, Begoña; Fernández, María; Martin, M Cruz; Alvarez, Miguel A

    2016-01-01

    Biofilms on the surface of food industry equipment are reservoirs of potentially food-contaminating bacteria-both spoilage and pathogenic. However, the capacity of biogenic amine (BA)-producers to form biofilms has remained largely unexamined. BAs are low molecular weight, biologically active compounds that in food can reach concentrations high enough to be a toxicological hazard. Fermented foods, especially some types of cheese, accumulate the highest BA concentrations of all. The present work examines the biofilm-forming capacity of 56 BA-producing strains belonging to three genera and 10 species (12 Enterococcus faecalis, 6 Enterococcus faecium, 6 Enterococcus durans, 1 Enterococcus hirae, 12 Lactococcus lactis, 7 Lactobacillus vaginalis, 2 Lactobacillus curvatus, 2 Lactobacillus brevis, 1 Lactobacillus reuteri, and 7 Lactobacillus parabuchneri), all isolated from dairy products. Strains of all the tested species - except for L. vaginalis-were able to produce biofilms on polystyrene and adhered to stainless steel. However, the biomass produced in biofilms was strain-dependent. These results suggest that biofilms may provide a route via which fermented foods can become contaminated by BA-producing microorganisms.

  9. Effects of packaging, mineral oil coating, and storage time on biogenic amine levels and internal quality of eggs.

    PubMed

    Figueiredo, T C; Assis, D C S; Menezes, L D M; Oliveira, D D; Lima, A L; Souza, M R; Heneine, L G D; Cançado, S V

    2014-12-01

    This study was carried out with the aim of evaluating the effects of mineral oil application on eggshells and the use of plastic packages with lids on the physical-chemical and microbiological quality and biogenic amine contents of eggs stored under refrigeration for up to 125 d. A total of 1,920 eggs from 46-wk-old Hyline W36 laying hens were randomly distributed into 4 groups soon after classification: (i) 480 eggs were stored in pulp carton tray packages; (ii) 480 eggs were stored in plastic packages with lids; (iii) 480 eggs were stored in carton packages after the application of mineral oil; and (iv) 480 eggs were stored in plastic packages with lids after the application of mineral oil. The internal quality was measured by Haugh units, by the counts of mesophilic and psychrotrophic microorganisms, by the most probable number of total and thermal-tolerant coliforms, by the counts of molds and yeasts, by the analysis of Salmonella spp. and Staphylococcus spp., and by the levels of biogenic amines in the egg yolk and albumen. The application of mineral oil to the eggshell resulted in higher Haugh unit values throughout storage, and the use of plastic packages altered the internal quality. The application of mineral oil and the use of packaging had no effects on the microbiological and biogenic amine results. Microbiological analyses showed the absence of Salmonella spp., Staphylococcus aureus, thermal-tolerant coliforms, and fungi. However, the highest counts of mesophilic (1.1 × 10(7) cfu/g) and psychrotrophic (6.7 × 10(7) cfu/g) microorganisms were recorded. The highest values of biogenic amines detected and quantified were putrescine (2.38 mg/kg) and cadaverine (7.27 mg/kg) in the egg yolk and putrescine (1.95 mg/kg), cadaverine (2.83 mg/kg), and phenylethylamine (2.57 mg/kg) in the albumen. Despite these results, the biogenic amine levels recorded were considered low and would not be harmful to consumer health. PMID:25306463

  10. Characterization of selected Spanish table wine samples according to their biogenic amine content from liquid chromatographic determination.

    PubMed

    Romero, Roberto; Sánchez-Viñas, Mercedes; Gázquez, Domingo; Bagur, M Gracia

    2002-07-31

    Pattern recognition techniques, such as principal component analysis, cluster analysis, and linear discriminant analysis, have been applied to samples of red, white, and rosé wines to determine whether some biogenic amines could be considered as chemical descriptors. Eight amines (tryptamine, phenylethylamine, putrescine, cadaverine, histamine, tyramine, spermidine, and spermine) were determined by RP-HPLC, after derivatization with dabsyl chloride. However, only putrescine, cadaverine, histamine, tyramine, spermidine, and spermine were found in the wines analyzed. From the association between variables obtained by principal component analysis and clustering and from the relationship found by linear discriminant analysis, it can be deduced that the amines generated during malolactic fermentation (putrescine, histamine, and tyramine) could be used as chemical descriptors to characterize table wine samples.

  11. Effects of pH, temperature and NaCl concentration on the growth kinetics, proteolytic activity and biogenic amine production of Enterococcus faecalis.

    PubMed

    Gardin, F; Martuscelli, M; Caruso, M C; Galgano, F; Crudele, M A; Favati, F; Guerzoni, M E; Suzzi, G

    2001-02-28

    In this work, the combined effects of temperature, pH and NaCl concentration on the growth dynamics of Enterococcus faecalis EF37, its proteolytic activity and its production of biogenic amines have been studied. The effects of the selected variables have been analysed using a Central Composite Design. The production of biogenic amines, under the adopted conditions, was found to be mainly dependent on the extent of growth of E. faecalis. Its proteolytic activity was not a limiting factor for the final amine production, because in the system studied (skim milk) an excess of precursors was guaranteed. Quantitatively, the most important biogenic amine produced was 2-phenylethylamine but substantial amounts of tyramine were detected in all the samples. This work confirms that the main biological feature influencing the biogenic amine formation is the extent of growth of microorganisms, like E. faecalis, characterised by decarboxylase activity. In the traditional and artisanal cheeses produced using raw milk, enterococci usually reach levels of 10(7) cells/g. With this perspective, it is important that the presence of biogenic amines due to the activities of these microorganisms is maintained within safe levels, without affecting the positive effects of enterococci on the final organoleptic characteristics of the cheese.

  12. Quantifying amine permeation sources with acid neutralization: calibrations and amines measured in coastal and continental atmospheres

    NASA Astrophysics Data System (ADS)

    Freshour, N. A.; Carlson, K. K.; Melka, Y. A.; Hinz, S.; Panta, B.; Hanson, D. R.

    2014-04-01

    An acid titration method for quantifying amine permeation rates was used to calibrate an Ambient pressure Proton transfer Mass Spectrometer (AmPMS) that monitors ambient amine compounds. The method involves capturing amines entrained in a N2 flow by bubbling it through an acidified solution (~ 10-5 M HCl), and the amines are quantified via changes in solution pH with time. Home-made permeation tubes had permeation rates (typically tens of pmol s-1) that depended on the type of amine and tubing and on temperature. Calibrations of AmPMS yielded sensitivities for ammonia, methyl amine, dimethyl amine, and trimethyl amine that are close to the sensitivity assuming a gas-kinetic, ion-molecule rate coefficient. The permeation tubes were also designed to deliver a reproducible amount of amine to a flow reactor where nucleation with sulfuric acid was studied. The high proton affinity compound dimethyl sulfoxide (DMSO), linked to oceanic environments, was also studied and AmPMS is highly sensitive to it. AmPMS was deployed recently in two field campaigns and mixing ratios are reported for ammonia, alkyl amines, and DMSO and correlations between these species and with particle formation events are discussed.

  13. Sex hormones and biogenic amine turnover of sex offenders in relation to their temperament and character dimensions.

    PubMed

    Giotakos, Orestis; Markianos, Manolis; Vaidakis, Nikos; Christodoulou, George N

    2004-07-15

    Relationships between Cloninger's temperament and character dimensions and plasma sex hormone levels and biogenic amine turnover were studied in male prison inmates convicted of rape (n=61) or child molestation (n=24) and normal male controls (n=25). The participants completed the Temperament and Character Inventory (TCI), which includes the temperament dimensions Novelty Seeking, Harm Avoidance, Reward Dependence and Persistence as well as the character dimensions Self-Directedness, Cooperativeness and Self-Transcendence. Plasma levels of testosterone, dihydrotestosterone, sex hormone binding globulin, luteinizing hormone (LH) and follicle-stimulating hormone were estimated in plasma samples and 5-hydroxyindoleacetic acid (5-HIAA), homovanillic acid (HVA), and 3-methoxy-4-hydroxyphenylglycol (MHPG) in urine samples. Both sex offender groups had higher Novelty, Seeking and lower Reward Dependence, Self-Directedness and Cooperativeness scores compared with the controls. Plasma levels of testosterone and dihydrotestosterone were significantly higher in rapists than in controls. Novelty Seeking scores were positively correlated with LH levels in rapists, and with testosterone levels in child molesters. Harm Avoidance scores were negatively correlated with 5-HIAA levels in rapists and with HVA levels in child molesters. In rapists, the calculated free androgen index showed a negative correlation with 5-HIAA. For the sex offender sample as a whole, the subgroup with high testosterone levels had higher Harm Avoidance scores, the subgroup with low HVA levels had lower Cooperativeness scores, and the subgroups with high 5HIAA or MHPG levels had lower Persistence scores. The results indicate that Novelty Seeking behavior in the group of rapists is associated with a hyperactive hypothalamic-pituitary-gonadal axis. In addition, low serotonin turnover and low dopamine turnover seem to be associated with a passive-avoidant behavioral style in rapists and child molesters

  14. Roles of biogenic amines in regulating bioluminescence in the Australian glowworm Arachnocampa flava.

    PubMed

    Rigby, Lisa M; Merritt, David J

    2011-10-01

    The glowworm Arachnocampa flava is a carnivorous fly larva (Diptera) that uses light to attract prey into its web. The light organ is derived from cells of the Malpighian tubules, representing a bioluminescence system that is unique to the genus. Bioluminescence is modulated through the night although light levels change quite slowly compared with the flashing of the better-known fireflies (Coleoptera). The existing model for the neural regulation of bioluminescence in Arachnocampa, based on use of anaesthetics and ligations, is that bioluminescence is actively repressed during the non-glowing phase and the repression is partially released during the bioluminescence phase. The effect of the anaesthetic, carbon dioxide, on the isolated light organ from the present study indicates that the repression is at least partially mediated at the light organ itself rather than less directly through the central nervous system. Blocking of neural signals from the central nervous system through ligation leads to uncontrolled release of bioluminescence but light is emitted at relatively low levels compared with under anaesthesia. Candidate biogenic amines were introduced by several methods: feeding prey items injected with test solution, injecting the whole larva, injecting a ligated section containing the light organ or bathing the isolated light organ in test solution. Using these methods, dopamine, serotonin and tyramine do not affect bioluminescence output. Exposure to elevated levels of octopamine via feeding, injection or bathing of the isolated light organ indicates that it is involved in the regulation of repression. Administration of the octopamine antagonists phentolamine or mianserin results in very high bioluminescence output levels, similar to the effect of anaesthetics, but only mianserin acts directly on the light organ.

  15. A biogenic source of oxalic acid and glyoxal in marine boundary layer

    NASA Astrophysics Data System (ADS)

    Facchini, C.; Rinaldi, M.; Ceburnis, D.; O'Dowd, C.; Sciare, J.; Burrows, J. P.

    2011-12-01

    We present the results of oxalic acid aerosol measurements samples performed at Mace Head (Ireland, 53°20'N, 9°54'W) and Amsterdam Island (Indian Ocean, 37°48'S, 77°34'E), supporting the existence of a biogenic source of oxalic acid over the oceans. Aerosol oxalic acid was detected in clean marine air masses in concentrations ranging from 2.7 to 39 ng m-3, at Mace Head, and from 0.31 to 17 ng m-3, at Amsterdam Island. In both hemispheres, oxalic acid concentration showed a clear seasonal trend, with maxima in spring-summer and minima in the fall-winter period, in analogy with other marine biogenic aerosol components (e.g., MSA and amines). Oxalic acid was distributed along the whole aerosol size spectrum, with the major contribution given by the 1.0-2.0 μm size range, and by the lower accumulation mode (0.25-0.5 μm). Given the observed size distributions, marine aerosol oxalic acid can be assumed as the result of the combination of different formation processes, among which in-cloud oxidation of gaseous precursors [1] and photochemical degradation of biogenic unsaturated fatty acids [2] are likely the most important. Among aerosol oxalic acid precursors, glyoxal is the most likely candidate in the marine boundary layer, as a source of glyoxal over the oceans has recently been discovered by satellite observations [3] and confirmed by in situ measurements [4]. In support of this hypothesis, SCIAMACHY satellite retrieved glyoxal column concentrations, over the two sampling sites, resulted characterized by a clear seasonal trend, resembling the aerosol oxalic acid one. [1] Warneck, Atmospheric Environment, 37, 2423-2427, 2003. [2] Kawamura & Sakaguchi, J. Geophys. Res., 104, D3, 3501-3509, 1999. [3] Fu et al., J. Geophys. Res., 113, D15303, doi:10.1029/2007JD009505, 2008 [4] Sinreich et al., Atmos. Chem. Phys. Discuss., 10, 15075-15107, 2010.

  16. Exposure to static electric fields leads to changes in biogenic amine levels in the brains of Drosophila

    PubMed Central

    Newland, Philip L.; Al Ghamdi, Mesfer S.; Sharkh, Suleiman; Aonuma, Hitoshi; Jackson, Christopher W.

    2015-01-01

    Natural and anthropogenic static electric fields are commonly found in the environment and can have both beneficial and harmful effects on many animals. Here, we asked how the fruitfly responds to these fields and what the consequences of exposure are on the levels of biogenic amines in the brain. When given a choice in a Y-tube bioassay Drosophila avoided electric fields, and the greater the field strength the more likely Drosophila were to avoid it. By comparing wild-type flies, flies with wings surgically removed and vestigial winged flies we found that the presence of intact wings was necessary to produce avoidance behaviour. We also show that Coulomb forces produced by electric fields physically lift excised wings, with the smaller wings of males being raised by lower field strengths than larger female wings. An analysis of neurochemical changes in the brains showed that a suite of changes in biogenic amine levels occurs following chronic exposure. Taken together we conclude that physical movements of the wings are used by Drosophila in generating avoidance behaviour and are accompanied by changes in the levels of amines in the brain, which in turn impact on behaviour. PMID:26224706

  17. Effect of Novel Starter Culture on Reduction of Biogenic Amines, Quality Improvement, and Sensory Properties of Doenjang, a Traditional Korean Soybean Fermented Sauce Variety.

    PubMed

    Shukla, Shruti; Lee, Jong Suk; Park, Hae-Kyong; Yoo, Jung-Ah; Hong, Sung-Yong; Kim, Jong-Kyu; Kim, Myunghee

    2015-08-01

    To select appropriate microorganisms as starter cultures for the reliable and reproducible fermentation of soybean fermented products of Korean Doenjang, various ratios of fungi (Aspergillus oryzae J, Mucor racemosus 15, M. racemosus 42) combined with Bacillus subtilis TKSP 24 were selected as either single, double, or multiple Meju strains for commercial mass production of Doenjang, followed by analysis of sensory characteristics. In the sensory evaluation, Doenjang BAM15-1 and BAM42-1, which were fermented with multiple strains (1:1:1), showed the highest sensory scores as compared to control. Based on sensory characteristics, 6 Doenjang samples were subjected to quantitative determination of amino acids, free sugars, and organic acids (volatile and nonvolatile) contents, followed by determination of biogenic amines. Total sweet taste amino acid contents were highest in BAM15-1 and BAM42-1 samples (333.7 and 295.8 mg/100 g, respectively) and similar that of control (391.1 mg/100 g). Samples BAM15-1 and BAM42-1 showed the relatively high volatile and nonvolatile organic acid contents (154.24, 192.26, and 71.31, 82.42 mg/100 g, respectively). In addition, BAM15-1 and BAM42-1 showed negligible biogenic amine formation, ranging from 0.00 to 1.02 and 0.00 to 3.92 mg/100 g, respectively. These findings indicate that determination of food components along with sensory and quality attributes using multiple microbial Meju strains as a starter culture may provide substantial results on improved quality fermented Doenjang products.

  18. Biogenic amine depletion causes chronic muscular pain and tactile allodynia accompanied by depression: A putative animal model of fibromyalgia.

    PubMed

    Nagakura, Yukinori; Oe, Tomoya; Aoki, Toshiaki; Matsuoka, Nobuya

    2009-11-01

    Fibromyalgia is a prevalent and burdensome disorder characterized by chronic widespread pain and complex comorbid symptoms. To develop better treatments for pain-centered fibromyalgia symptoms, there is still a need for animal models which mimic the features of fibromyalgia patients. In the present study, we have established a fibromyalgia animal model by utilizing a never-before-published pharmacological effect of reserpine. Repeated administration of reserpine (1mg/kg s.c., once daily, for three consecutive days) causes a significant decrease in the muscle pressure threshold and tactile allodynia, which are sustained for 1week or more in both male and female rats. This treatment regimen decreases the amount of biogenic amines (dopamine, norepinephrine, and 5-hydroxytryptamine) in the spinal cord, thalamus, and prefrontal cortex, which are deeply involved in pain signal processing. It also significantly increases immobility time in the forced swim test, which is indicative of depression, a common comorbid symptom of fibromyalgia. Pregabalin, duloxetine, and pramipexole significantly attenuated the reserpine-induced decrease in muscle pressure threshold, but diclofenac did not. The validity of the use of this reserpinized animal as a fibromyalgia model is demonstrated from three different aspects, i.e., face validity (manifestation of chronic pain and comorbid symptoms), construct validity (dysfunction of biogenic amine-mediated central nervous system pain control is involved), and predictive validity (similar responses to treatments used in fibromyalgia patients). This animal model is expected to contribute to the better understanding of fibromyalgia pathophysiology and the evaluation of drugs, especially those which would activate biogenic amine system.

  19. Mastitis Modifies the Biogenic Amines Profile in Human Milk, with Significant Changes in the Presence of Histamine, Putrescine and Spermine.

    PubMed

    Perez, Marta; Ladero, Victor; Redruello, Begoña; Del Rio, Beatriz; Fernandez, Leonides; Rodriguez, Juan Miguel; Martín, M Cruz; Fernandez, María; Alvarez, Miguel A

    2016-01-01

    Biogenic amines (BAs) are low molecular weight nitrogenous organic compounds with different biological activities. Putrescine, spermidine and spermine are essential for the development of the gut and immune system of newborns, and are all found in human milk. Little is known, however, about the role of histamine, tyramine or cadaverine in breast milk. Nor is it known whether mastitis alters the BA composition of milk. The BA profile of human milk, and the influence of mastitis on BA concentrations, were therefore investigated. Putrescine, spermidine and spermine were the main BAs detected. In mastitis-affected milk, the concentrations of putrescine, spermine and histamine were higher. PMID:27584695

  20. Mastitis Modifies the Biogenic Amines Profile in Human Milk, with Significant Changes in the Presence of Histamine, Putrescine and Spermine.

    PubMed

    Perez, Marta; Ladero, Victor; Redruello, Begoña; Del Rio, Beatriz; Fernandez, Leonides; Rodriguez, Juan Miguel; Martín, M Cruz; Fernandez, María; Alvarez, Miguel A

    2016-01-01

    Biogenic amines (BAs) are low molecular weight nitrogenous organic compounds with different biological activities. Putrescine, spermidine and spermine are essential for the development of the gut and immune system of newborns, and are all found in human milk. Little is known, however, about the role of histamine, tyramine or cadaverine in breast milk. Nor is it known whether mastitis alters the BA composition of milk. The BA profile of human milk, and the influence of mastitis on BA concentrations, were therefore investigated. Putrescine, spermidine and spermine were the main BAs detected. In mastitis-affected milk, the concentrations of putrescine, spermine and histamine were higher.

  1. Mastitis Modifies the Biogenic Amines Profile in Human Milk, with Significant Changes in the Presence of Histamine, Putrescine and Spermine

    PubMed Central

    Perez, Marta; Ladero, Victor; Redruello, Begoña; del Rio, Beatriz; Fernandez, Leonides; Rodriguez, Juan Miguel; Martín, Mª Cruz; Fernandez, María; Alvarez, Miguel A.

    2016-01-01

    Biogenic amines (BAs) are low molecular weight nitrogenous organic compounds with different biological activities. Putrescine, spermidine and spermine are essential for the development of the gut and immune system of newborns, and are all found in human milk. Little is known, however, about the role of histamine, tyramine or cadaverine in breast milk. Nor is it known whether mastitis alters the BA composition of milk. The BA profile of human milk, and the influence of mastitis on BA concentrations, were therefore investigated. Putrescine, spermidine and spermine were the main BAs detected. In mastitis-affected milk, the concentrations of putrescine, spermine and histamine were higher. PMID:27584695

  2. Structure and ligand-binding properties of the biogenic amine-binding protein from the saliva of a blood-feeding insect vector of Trypanosoma cruzi

    SciTech Connect

    Xu, Xueqing; Chang, Bianca W.; Ribeiro, Jose M. C.; Andersen, John F.

    2013-01-01

    Biogenic amine-binding proteins mediate the anti-inflammatory and antihemostatic activities of blood-feeding insect saliva. The structure of the amine-binding protein from R. prolixus reveals the interaction of biogenic amine ligands with the protein. Proteins that bind small-molecule mediators of inflammation and hemostasis are essential for blood-feeding by arthropod vectors of infectious disease. In ticks and triatomine insects, the lipocalin protein family is greatly expanded and members have been shown to bind biogenic amines, eicosanoids and ADP. These compounds are potent mediators of platelet activation, inflammation and vascular tone. In this paper, the structure of the amine-binding protein (ABP) from Rhodnius prolixus, a vector of the trypanosome that causes Chagas disease, is described. ABP binds the biogenic amines serotonin and norepinephrine with high affinity. A complex with tryptamine shows the presence of a binding site for a single ligand molecule in the central cavity of the β-barrel structure. The cavity contains significant additional volume, suggesting that this protein may have evolved from the related nitrophorin proteins, which bind a much larger heme ligand in the central cavity.

  3. Brewing effect on levels of biogenic amines in different coffee samples as determined by LC-UV.

    PubMed

    Restuccia, Donatella; Spizzirri, U Gianfranco; Parisi, Ortensia I; Cirillo, Giuseppe; Picci, Nevio

    2015-05-15

    Eight biogenic amines (spermine, spermidine, putrescine, histamine, tyramine, phenylethylamine, cadaverine and serotonin) were determined by LC-UV after derivatization with dansyl-chloride in both ground coffee and coffee beverages obtained by different methods. In ground coffee, the most relevant amine was PUT, followed by SPD, HIS, TYR, CAD, SPM, PHE, and SER, with the total BAs content decreasing as the roasting degree increased. In coffee brews, the order was PUT, SPM, TYR, CAD, SPD, PHE, HIS, and SER, but at a very low level in comparison with the amount of BAs determined in roasted ground coffee. Beverages prepared by espresso, capsule, and pod machines had the lowest BAs contents, as a result of the thermal and physical stress imposed on ground coffee by these methods, while mocha contained the highest BAs amounts owing to lower pressure and longer brewing time.

  4. Brewing effect on levels of biogenic amines in different coffee samples as determined by LC-UV.

    PubMed

    Restuccia, Donatella; Spizzirri, U Gianfranco; Parisi, Ortensia I; Cirillo, Giuseppe; Picci, Nevio

    2015-05-15

    Eight biogenic amines (spermine, spermidine, putrescine, histamine, tyramine, phenylethylamine, cadaverine and serotonin) were determined by LC-UV after derivatization with dansyl-chloride in both ground coffee and coffee beverages obtained by different methods. In ground coffee, the most relevant amine was PUT, followed by SPD, HIS, TYR, CAD, SPM, PHE, and SER, with the total BAs content decreasing as the roasting degree increased. In coffee brews, the order was PUT, SPM, TYR, CAD, SPD, PHE, HIS, and SER, but at a very low level in comparison with the amount of BAs determined in roasted ground coffee. Beverages prepared by espresso, capsule, and pod machines had the lowest BAs contents, as a result of the thermal and physical stress imposed on ground coffee by these methods, while mocha contained the highest BAs amounts owing to lower pressure and longer brewing time. PMID:25577063

  5. Turnover of Biogenic Amines in the Hypothalamus of Rats during Pyrogen Fever

    NASA Technical Reports Server (NTRS)

    Penn, P. E.; Williams, B. A.

    1979-01-01

    Many pharmacological studies have implicated the biogenic amines in the hypothalamus as playing a role in the production of fever, but few investigations of endogenous neurochemicals have been made during fever. Turnover rates of transmitters utilizing radioactive precursors may be one of the most accurate measurements of activity in brain regions. The present study was designed to measure the turnover of 5-hydroxytryptamine (5-HT) norepinephrine (NE) and dopamine (DA) in the hypothalamus of rats during pyrogen fever. Salmonella typhosa (Wyeth, 8 units) was previously found in our laboratory to produce a significant hyperthermia in most rats by 2.5 hours. This pyrogen (N = l2) or saline control (N = 8) was injected intraperitoneally and the rats killed 2.75 hours later. Rectal temperatures (Tr) were monitored continuously with thermocouples taped to the tail and recorded automatically every 3 minutes. Half of each group received an injection of radioactive precursors, (3)H-tryptophan (0.5 mCi) and (3)H-tryptophan (1.0 mCi), via an indwelling jugular catheter 60 minutes before killing, and the other half at 90 minutes. The rats were killed by near freezing in liquid nitrogen and the brains dissected in the cold. Turnover was measured by the method of Lane (Life Sci 21, 1101, 1977). At the time of killing most of the pyrogen group showed a significant (p < .02) increase (mean +/- s.e.m.) in Tr above pre injection levels (0.75 +/- 0.13 C, N = 10). The saline group showed no change (-0.025 +/- 0.16, N = 8), and the difference between groups was also significant. No significant differences were found in the levels of the amines between the pyrogen and saline groups. A significant difference was found in the specific activity of NE between the 60 minute pyrogen and saline groups (4.41 +/- 0.41 vs 2.6 +/- 0.51 dpm/pmole) but no change in turnover. This suggests an increased accumulation of (3)H-NE in the pyrogen group, but no change in utilization. An increased turnover

  6. Formation of biogenic amines and growth of spoilage-related microorganisms in pork stored under different packaging conditions applying PCA.

    PubMed

    Li, Miaoyun; Tian, Lu; Zhao, Gaiming; Zhang, Qiuhui; Gao, Xiaoping; Huang, Xianqing; Sun, Lingxia

    2014-02-01

    The objective of this study was to investigate the evolution of biogenic amines and spoilage-related microorganisms of chilled pork stored at 5 °C under various atmospheric conditions. The experimental packaging systems were pallet packaging, vacuum packaging (VP) and modified atmosphere packaging methods (MAP, 40%O2+40%CO2+20%N2), respectively. The results showed that about 74.26% of the variability could be explained by two first principal components analyzed by PCA in the pallet packaging, while in the vacuum and modified atmosphere packagings were about 85.21% and 79.14%, respectively. PC1 differentiated the indicators from packaging conditions. All the five microbial indicators and partial biogenic amines, gathering together, had high values at the positive side of PC1. Putrescine and cadaverine could reflect the spoilage evolution of fresh pork except for those in the pallet. Therefore, putrescine and cadaverine could be used as the spoilage indicators of chilled pork, of which the contents might reflect the spoilage degree. PMID:24200579

  7. Evolution of biogenic amine concentrations in foods through their induced chemiluminescence inactivation of layered double hydroxide nanosheet colloids.

    PubMed

    Wang, Zhihua; Liu, Fang; Lu, Chao

    2014-10-15

    Turn-on/off fluorescence and visual sensors through hydrogen bonding recognition have been clearly established in the literature. There is apparently no good reason to disregard hydrogen bonding-induced inactivation of chemiluminescence (CL). In this work, serving as novel CL catalyst and CL resonance energy transfer acceptor (CRET), layered double hydroxide (LDH) nanosheet colloids can induce a significant increase in the CL intensity of bis(2,4,6-trichlorophenyl) oxalate (TCPO)-H2O2 system. On the other hand, biogenic amines can selectively inhibit the CL intensity of the LDH nanosheet-TCPO-H2O2 system as a result of inactivation of photoluminescence LDH nanosheets through the displacement of O-H ⋯ O bonding by O-H ⋯ N bonding. In addition, histamine is used as a common indicator of food spoilage, and it is found that the CL intensity is linear with histamine concentration in the range of 0.1-100 µM, and the detection limit for histamine (S/N=3) is 3.2 nM. The proposed method has been successfully applied to trace histamine evolution of spoiled fish and pork meat samples, displaying a time-dependent increase in the biogenic amines levels in such samples. PMID:24813913

  8. Formation of biogenic amines and growth of spoilage-related microorganisms in pork stored under different packaging conditions applying PCA.

    PubMed

    Li, Miaoyun; Tian, Lu; Zhao, Gaiming; Zhang, Qiuhui; Gao, Xiaoping; Huang, Xianqing; Sun, Lingxia

    2014-02-01

    The objective of this study was to investigate the evolution of biogenic amines and spoilage-related microorganisms of chilled pork stored at 5 °C under various atmospheric conditions. The experimental packaging systems were pallet packaging, vacuum packaging (VP) and modified atmosphere packaging methods (MAP, 40%O2+40%CO2+20%N2), respectively. The results showed that about 74.26% of the variability could be explained by two first principal components analyzed by PCA in the pallet packaging, while in the vacuum and modified atmosphere packagings were about 85.21% and 79.14%, respectively. PC1 differentiated the indicators from packaging conditions. All the five microbial indicators and partial biogenic amines, gathering together, had high values at the positive side of PC1. Putrescine and cadaverine could reflect the spoilage evolution of fresh pork except for those in the pallet. Therefore, putrescine and cadaverine could be used as the spoilage indicators of chilled pork, of which the contents might reflect the spoilage degree.

  9. Production of biogenic amines "in vitro" in relation to the growth phase by Enterobacteriaceae species isolated from traditional sausages.

    PubMed

    Lorenzo, José M; Cachaldora, Aida; Fonseca, Sonia; Gómez, María; Franco, Inmaculada; Carballo, Javier

    2010-11-01

    Histidine, lysine, ornithine and tyrosine decarboxylase activities were tested in 79 strains of Enterobacteriaceae (41 of Hafnia alvei, 17 of Serratia liquefaciens, 5 of Enterobacter cloacae, 4 of Citrobacter braakii, 2 of Proteus vulgaris, 2 of Proteus mirabilis, 2 of Providencia stuartii, 2 of Klebsiella terrigena, 1 of Rahnella aquatilis, 1 of Salmonella arizonae, 1 of Citrobacter youngae and 1 of Escherichia coli) isolated from Botillo, a Spanish traditional sausage. In general, the strains were positive for all four activities, with the exception of two strains of H. alvei and the E. coli strain, which did not display histidine decarboxylase activity. The strains of P. mirabilis and P. stuartii did not exhibit any of the four activities tested. Accumulation of putrescine and cadaverine was studied throughout growth of the 75 strains that displayed ornithine and lysine decarboxylase activities. Biogenic amines were produced particularly in the exponential phase, with maximum accumulation occurring after between 12 to 72 h, depending on the biogenic amine and microbial species considered. Maximum accumulation of putrescine varied greatly between species and within the same species, and ranged from 18 mg/l in the R. aquatilis strain to 7325 mg/l in a H. alvei strain. Maximum accumulation of cadaverine varied less than that of putrescine, and ranged from 30 mg/l in the R. aquatilis strain to 1935 mg/l in a S. liquefaciens strain. PMID:20673614

  10. Histamine-producing bacteria in blue scad (Decapterus maruadsi) and their abilities to produce histamine and other biogenic amines.

    PubMed

    Hu, Yue; Huang, Zhiyong; Chen, Xia

    2014-08-01

    Using decarboxylation medium and 16S rDNA sequence analysis, histamine-producing bacteria (HPB) in blue scad (Decapterus maruadsi) were isolated and identified, and the histamine-producing abilities of the isolated HPB were determined. Nine mesophilic strains (H1-H9) isolated from the muscle of blue scad were identified as the genera of HPB, including Arthrobacter bergeri (H1), Pseudomonas sp. (H2, H5 and H6), Psychrobacter sp. (H3), Shewanella baltica (H4 and H7), and Aeromonas salmonicida (H8 and H9), respectively. Results showed that most of the HPB strains were weak on histamine formation (13.0-20.4 mg/l), except for the H8 strain with the ability of producing 115 mg of histamine/l in trypticase soy broth containing 1.0 % L-histidine. As the strongest HPB in blue scad, bacterial strain H8 also presented a strong ability to produce other biogenic amines, such as putrescine, cadaverine, spermidine, spermine, tyramine and tryptamine. Therefore, the H8 strain identified as the genus of A. salmonicida was the dominant mesophilic HPB strain for producing histamine and other biogenic amines in blue scad at room temperature. PMID:24668182

  11. Acid-catalyzed dehydrogenation of amine-boranes

    DOEpatents

    Stephens, Frances Helen; Baker, Ralph Thomas

    2010-01-12

    A method of dehydrogenating an amine-borane using an acid-catalyzed reaction. The method generates hydrogen and produces a solid polymeric [R.sup.1R.sup.2B--NR.sup.3R.sup.4].sub.n product. The method of dehydrogenating amine-boranes may be used to generate H.sub.2 for portable power sources.

  12. Amine permeation sources characterized with acid neutralization and sensitivities of an amine mass spectrometer

    NASA Astrophysics Data System (ADS)

    Freshour, N. A.; Carlson, K. K.; Melka, Y. A.; Hinz, S.; Panta, B.; Hanson, D. R.

    2014-10-01

    An acid titration method for quantifying amine permeation rates was used to calibrate an Ambient pressure Proton transfer Mass Spectrometer (AmPMS) that monitors ambient amine compounds. The method involves capturing amines entrained in a N2 flow by bubbling it through an acidified solution (~10-5 M HCl), and the amines are quantified via changes in solution pH with time. Home-made permeation tubes had permeation rates (typically tens of pmol s-1) that depended on the type of amine and tubing and on temperature. Calibrations of AmPMS yielded sensitivities for ammonia, methylamine, dimethylamine, and trimethylamine that are close to the sensitivity assuming a gas-kinetic, ion-molecule rate coefficient. The permeation tubes were also designed to deliver a reproducible amount of amine to a flow reactor where nucleation with sulfuric acid was studied. The high proton affinity compound dimethyl sulfoxide (DMSO), linked to oceanic environments, was also studied and AmPMS is highly sensitive to it. AmPMS was deployed recently in two field campaigns and, using these sensitivities, mixing ratios for ammonia and the alkyl amines are derived from the signals. Correlations between these species and with particle formation events are discussed.

  13. Regulatory roles of biogenic amines and juvenile hormone in the reproductive behavior of the western tarnished plant bug (Lygus hesperus).

    PubMed

    Brent, Colin S; Miyasaki, Katelyn; Vuong, Connor; Miranda, Brittany; Steele, Bronwen; Brent, Kristoffer G; Nath, Rachna

    2016-02-01

    Mating induces behavioral and physiological changes in the plant bug Lygus hesperus Knight (Hemiptera: Miridae). After receiving seminal products, which include the systemic regulator juvenile hormone (JH), females enter a post-mating period lasting several days during which they enhance their oviposition rate and lose interest in remating. To elucidate the regulation of these behavioral changes in L. hesperus, biogenic amines were quantified in the heads of females at 5 min, 1 h and 24 h after copulation and compared to levels in virgins using high-performance liquid chromatography coupled with electrochemical detection. Mating significantly increased dopamine (DA) after 1 and 24 h, and decreased octopamine (OA) after 5 min and 1 h. Serotonin did not change with mating, but tyramine was significantly reduced after 5 min. While injection of amines into virgin females did not influence sexual receptivity, OA caused a decrease in oviposition during the 24 h following injection. Topical application of the JH analog methoprene to virgins caused an increase in DA, and a decline in mating propensity, but did not influence other amines or the oviposition rate. The results suggest the decline in OA observed immediately after mating may promote egg laying, and that male-derived JH may induce an increase in DA that could account for the post-mating loss of sexual receptivity.

  14. Basic biogenic aerosol precursors: Agricultural source attribution of volatile amines revised

    NASA Astrophysics Data System (ADS)

    Kuhn, U.; Sintermann, J.; Spirig, C.; Jocher, M.; Ammann, C.; Neftel, A.

    2011-08-01

    Despite recent evidence on an important role of volatile amines in the nucleation of particulate matter, very scarce information is available on their atmospheric abundance and source distribution. Previous measurements in animal housings had identified livestock husbandry as the main amine source, with trimethylamine (TMA) being the key component. This has led to the assumption that the agricultural sources for amines are similar as for ammonia, emitted throughout the cascade of animal excretion, storage and application in the field. In this study, we present the first micrometeorological flux measurements as well as dynamic enclosure experiments showing that the amine source strength from stored slurry is negligible, implying significant consequences for the global amine emission inventory. In the case of cattle, amine production is attributed to the animal's rumination activity and exhalation is suggested to be an important emission pathway, similar to the greenhouse gas methane. Fodder like hay and silage also emits volatile amines, potentially assigning these alkaloid compounds a key function in enhancing particle formation in remote areas.

  15. Formation of biogenic amines in raw milk Hispánico cheese manufactured with proteinases and different levels of starter culture.

    PubMed

    Fernandez-García, E; Tomillo, J; Nuñez, M

    2000-11-01

    Two proteinases, a neutral proteinase from Bacillus subtilis and a cysteine proteinase from Micrococcus sp., were used to accelerate the ripening process of raw cow's milk Hispánico cheese, a semihard variety. Two levels (0.1% and 1%) of a commercial starter culture containing Lactococcus lactis subsp. lactis and L. lactis subsp. cremoris were added for cheese manufacture. The influence of both factors, proteinase addition and level of starter culture, on the growth of amino acid-decarboxylating microorganisms and on the formation of biogenic amines during cheese ripening was investigated in duplicate experiments. The population of tyrosine decarboxylase-positive bacteria, which represented less than 1% of the total bacterial population in most cheese samples, and tyrosine decarboxylase-positive lactobacilli was not influenced by proteinase addition or level of starter culture. Tyramine was detected in all batches of cheese from day 30. Its concentration was significantly (P < 0.05) influenced by proteinase addition but not by the level of starter culture and increased with cheese age. After 90 days of ripening, 103 to 191 mg/kg of tyramine was found in the different cheese batches. Histamine was not detected until day 60 in cheese with neutral proteinase and 1% starter culture and until day 90 in the rest of the cheeses. The concentration of this amine did not exceed 20 mg/kg in any of the batches investigated. Phenylethylamine and tryptamine were not found in any of the samples.

  16. The effect of beta-endorphin on biogenic amines, insulin, and glucagon levels in the hepatic portal circulation of normal and pancreatectomized dogs.

    PubMed

    Hussain, M N; Kikuchi, K; Cukerman, E; Sirek, A; Sirek, O V

    1986-08-01

    The effect of peak concentrations of beta-endorphin on hepatic portal and peripheral levels of plasma catecholamines, free serotonin, glucose, insulin, and glucagon was studied in trained, conscious, normal adult dogs fitted with an indwelling portal catheter. An injection of synthetic human beta-endorphin (20 micrograms/kg BW) into a cephalic vein produced a significant rise in the portal concentration of dopamine, norepinephrine, and epinephrine. The rise was accompanied by a reduction of portal free serotonin levels. The changes were not seen in the peripheral circulation. No appreciable changes in plasma insulin, glucagon, and glucose concentrations were noticed either in the hepatic portal or in the peripheral circulation. The response of the biogenic amines to beta-endorphin was abolished by pretreatment with Naltrexone (1 mg/kg BW). A dose of somatostatin antiserum given before beta-endorphin did not alter the biogenic amine response to the opioid peptide. When beta-endorphin was administered to pancreatectomized dogs devoid of exogenous and endogenous insulin supply, the biogenic amine response remained virtually the same as in normal intact dogs. It is concluded that in the dog a pulse of beta-endorphin causes profound alterations of splanchnic biogenic amine concentrations that are independent of the ambient levels of insulin, somatostatin, and pancreatic glucagon.

  17. Effects of plant polyphenols and a-tocopherol on lipid oxidation, microbiological characteristics, and biogenic amines formation in dry-cured bacons

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Effects of plant polyphenols (tea polyphenol, grape seed extract, and gingerol) and a-tocopherol on physicochemical parameters, microbiological counts, and biogenic amines were determined in dry-cured bacons at the end of ripening. Results showed that plant polyphenols and a-tocopherol significantly...

  18. Genome Sequence Analysis of the Biogenic Amine-Producing Strain Lactococcus lactis subsp. cremoris CECT 8666 (Formerly GE2-14)

    PubMed Central

    del Rio, Beatriz; Linares, Daniel M.; Fernandez, Maria; Mayo, Baltasar; Martin, M. Cruz; Alvarez, Miguel A.

    2014-01-01

    We here report a 2,801,031-bp annotated draft assembly for the Lactococcus lactis subsp. cremoris GE2-14 genome. This dairy strain produces the biogenic amine putrescine. This sequence may help identify the mechanisms regulating putrescine biosynthesis and throw light on ways to reduce its presence in fermented foods. PMID:25342694

  19. Amine Reactivity with Nanoclusters of Sulfuric Acid and Ammonia

    NASA Astrophysics Data System (ADS)

    Johnston, M. V.; Bzdek, B. R.; DePalma, J.

    2011-12-01

    Alkyl amines have emerged as key species in new particle formation and growth. This interest is reinforced by ambient measurements of amines (e.g. Smith et al., 2010) and enhanced levels of nitrogen (e.g. Bzdek et al., 2011) during growth of newly formed particles. An important mechanism of amine uptake is aminium salt formation, either by substituting for ammonium ions that already exist in the particle or by opening new channels for salt formation that are not favorable with ammonia. This presentation will focus on recent experimental and computational work in our group to study amine uptake into charged nanoclusters of sulfuric acid and ammonia. In the experimental work, clusters are produced by electrospray of an ammonium sulfate solution and then drawn into a Fourier transform ion cyclotron resonance mass spectrometer where a specific cluster is isolated and exposed to amine vapor. We find that amine reactivity is dependent on the size, composition and charge of the isolated cluster. For small clusters of either polarity, all ammonium ions reside on the surface and amine substitution occurs with near unit reaction probability. As the cluster size increases, an ammonium ion can be encapsulated in the center of the cluster, which provides a steric hindrance to amine substitution. Negatively charged clusters are more likely to be acidic than positively charged clusters. For acidic clusters, incoming amine molecules first substitute for preexisting ammonium ions and then add to the cluster until a "neutralized" aminium bisulfate composition is reached. Computational studies of these clusters provide fundamental insight into the thermodynamics and kinetics of amine uptake.

  20. Effect of delayed icing on biogenic amines formation and bacterial contribution of iced common carp (Cyprinus carpio).

    PubMed

    Hosseini, Seyed Vali; Hamzeh, Ali; Moslemi, Mehran; Lashkan, Aria Babakhani; Iglesias, Antonio; Feás, Xesús

    2013-12-12

    The variation of six biogenic amines (BAs) and total viable count (TVC) in common carp (Cyprinus carpio) stored in ice with 0, 4 and 8 h delay before icing was evaluated in a period of 4 days. Delayed icing led to significant (p < 0.05) increases in TVC throughout the period of storage and showed a good correlation with BAs content. The obtained data showed that putrescine and cadaverine were predominant in all samples and it was indicated that they could be proper indicators to determine the carp quality. Spermidine and spermine increased slightly toward the end of storage and the levels of dangerous BAs (histamine and tyramine) were under the limit over the period. As a result, it is indicated that delaying time affects on formation of BAs and the effect in samples with 8 h delay was significantly (p < 0.05) more than those with 0 and 4 h delay.

  1. The effect of treating method of pithed pheasant on the content of biogenic amines in the meat during the course of storage.

    PubMed

    Hutarova, Z; Vecerek, V; Steinhauserova, I; Marsalek, P; Borilova, G; Forejtek, P

    2013-08-01

    The study monitored the effect of various methods of treating pheasant carcasses after killing on the hygienic quality of the venison. Pithed pheasants treated by evisceration (n = 60), drawing (n = 60), or left untreated (n = 60) were stored for a period of 21 d at temperatures of 0, 7, and 15°C. For determination of biogenic amines, samples of breast and thigh muscles were taken on d 1, 7, 14, and 21 after killing of the pheasants. Biogenic amines were separated by reverse-phase liquid chromatography and consequently detected by tandem mass spectrometry. The sum of determined biogenic amine concentrations (cadaverine, putrescine, histamine, tyramine, tryptamine, phenylethylamine) was compared with the value of the index for meat of high hygienic quality (5 mg/kg). At a storage temperature of 0°C, the sum of biogenic amine concentrations did not exceed the value of 5 mg/kg in either breast or thigh muscle at any time during the storage period in untreated and drawn pheasants, and for a period of 14 d in eviscerated pheasants. At a storage temperature of 7°C, values lower than the limit of 5 mg/kg were recorded throughout the storage period in untreated pheasants, for a period of 14 d of storage in drawn pheasants, and for a period of just 7 d of storage in eviscerated birds. At the highest storage temperature (15°C), a value of 5 mg/kg was exceeded in eviscerated and untreated pheasants during the course of the first week of storage, and in drawn pheasants after the first week of storage. Our results indicate that the most suitable method of treatment to ensure high hygienic quality of the meat (assessed according to concentration of biogenic amines) for the longest period during the storage of pithed pheasants is to leave the pheasant carcasses untreated, followed by the drawing, with the least suitable method being the widely recommended method of evisceration.

  2. Effects of ultraviolet light on biogenic amines and other quality indicators of chicken meat during refrigerated storage.

    PubMed

    Lázaro, C A; Conte-Júnior, C A; Monteiro, M L G; Canto, A C V S; Costa-Lima, B R C; Mano, S B; Franco, R M

    2014-09-01

    Radiation from UV-C has been demonstrated as a potential surface decontamination method in addition to several advantages over regular sanitation methods. However, UV-C radiation possibly affects the physicochemical properties of meat products. To determine the optimum exposure time for bacterial reduction, 39 chicken breasts, inoculated with a pool of Salmonella spp., were submitted to 3 levels of UV-C intensities (0.62, 1.13, and 1.95 mW/cm²) for up to 120 s. After the optimum exposure time of 90 s was determined, changes in the biogenic amines, total aerobic mesophilic bacteria, Enterobacteriaceae, lipid oxidation, pH, and instrumental color were evaluated in 84 chicken breasts that were irradiated (0.62, 1.13, and 1.95 mW/cm²) and stored at 4°C for 9 d. The groups treated with UV-C radiation exhibited an increase in tyramine, cadaverine, and putrescine contents (P < 0.05). The highest UV-C intensity (1.95 mW/cm²) promoted a decrease in the initial bacterial load, and extended the lag phase and the shelf life. The groups irradiated with 1.13 and 1.95 mW/cm² exhibited a more stable b* value than the other groups; similar trends for L*, a*, pH, and TBA reactive substance values were observed among all groups. The UV-C light was demonstrated to be an efficient alternative technology to improve the bacteriological quality of chicken meat without negatively affecting the physical and chemical parameters of chicken breast meat. Nonetheless, the increases on the biogenic amines content should be considered as an effect of the UV processing and not as an indicator of bacterial growth. PMID:24974390

  3. The sugar model: catalysis by amines and amino acid products

    NASA Technical Reports Server (NTRS)

    Weber, A. L.

    2001-01-01

    Ammonia and amines (including amino acids) were shown to catalyze the formation of sugars from formaldehyde and glycolaldehyde, and the subsequent conversion of sugars to carbonylcontaining products under the conditions studied (pH 5.5 and 50 degrees C). Sterically unhindered primary amines were better catalysts than ammonia, secondary amines, and sterically hindered primary amines (i.e. alpha-aminoisobutyric acid). Reactions catalyzed by primary amines initially consumed formaldehyde and glycolaldehyde about 15-20 times faster than an uncatalyzed control reaction. The amine-catalyzed reactions yielded aldotriose (glyceraldehyde), ketotriose (dihydroxyacetone), aldotetroses (erythrose and threose), ketotetrose (erythrulose), pyruvaldehyde, acetaldehyde, glyoxal, pyruvate, glyoxylate, and several unindentified carbonyl products. The concentrations of the carbonyl products, except pyruvate and ketotetrose, initially increased and then declined during the reaction, indicating their ultimate conversion to other products (like larger sugars or pyruvate). The uncatalyzed control reaction yielded no pyruvate or glyoxylate, and only trace amounts of pyruvaldehyde, acetaldehyde and glyoxal. In the presence of 15 mM catalytic primary amine, such as alanine, the rates of triose and pyruvaldehyde of synthesis were about 15-times and 1200-times faster, respectively, than the uncatalyzed reaction. Since previous studies established that alanine is synthesized from glycolaldehyde and formaldehyde via pyruvaldehyde as its direct precursor, the demonstration that the alanine catalyzes the conversion of glycolaldehyde and formaldehyde to pyruvaldehyde indicates that this synthetic pathway is capable of autocatalysis. The relevance of this synthetic process, named the Sugar Model, to the origin of life is discussed.

  4. 40 CFR 721.3620 - Fatty acid amine condensate, polycarboxylic acid salts.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Fatty acid amine condensate, polycarboxylic acid salts. 721.3620 Section 721.3620 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.3620 Fatty acid amine condensate, polycarboxylic acid salts....

  5. 40 CFR 721.3620 - Fatty acid amine condensate, polycarboxylic acid salts.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Fatty acid amine condensate, polycarboxylic acid salts. 721.3620 Section 721.3620 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.3620 Fatty acid amine condensate, polycarboxylic acid salts....

  6. 40 CFR 721.3620 - Fatty acid amine condensate, polycarboxylic acid salts.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Fatty acid amine condensate, polycarboxylic acid salts. 721.3620 Section 721.3620 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.3620 Fatty acid amine condensate, polycarboxylic acid salts....

  7. 40 CFR 721.3620 - Fatty acid amine condensate, polycarboxylic acid salts.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Fatty acid amine condensate, polycarboxylic acid salts. 721.3620 Section 721.3620 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.3620 Fatty acid amine condensate, polycarboxylic acid salts....

  8. 40 CFR 721.3620 - Fatty acid amine condensate, polycarboxylic acid salts.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Fatty acid amine condensate, polycarboxylic acid salts. 721.3620 Section 721.3620 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... Specific Chemical Substances § 721.3620 Fatty acid amine condensate, polycarboxylic acid salts....

  9. Effect of a single neonatal oxytocin treatment (hormonal imprinting) on the biogenic amine level of the adult rat brain: could oxytocin-induced labor cause pervasive developmental diseases?

    PubMed

    Hashemi, F; Tekes, Kornélia; Laufer, R; Szegi, P; Tóthfalusi, L; Csaba, G

    2013-10-01

    Perinatal single-hormone treatment causes hormonal imprinting with lifelong consequences in receptor-binding capacity, hormone production as well as in social and sexual behavior. In the present experiments, newborn rats were treated with a single dose of oxytocin, and the levels of biogenic amines and their metabolites were studied in 8 different brain regions and in the sera when the male and female animals were 4 months old. Both dopaminergic and serotonergic neurotransmission was found to be significantly influenced. The levels of 3,4-dihydroxyphenylacetic acid, homovanillic acid, and 5-hydroxyindole acetic acid metabolites decreased in the hypothalamus and striatum. Dopamine, serotonin, norepinephrine, and 5-hydroxytryptophol levels were hardly altered, and there was no difference in the epinephrine levels. The results show that dopamine and serotonin metabolism of hypothalamus and striatum are deeply and lifelong influenced by a single neonatal oxytocin treatment Oxytocin imprinting resulted in decreased dopamine turnover in the hypothalamus and decreased serotonin turnover in the hypothalamus, medulla oblongata, and striatum of females. As the disturbance of brain dopamine and serotonin system has an important role in the development of pervasive developmental diseases (eg, autism) and neuropsychiatric disorders (eg, schizophrenia), the growing number of oxytocin-induced labor as a causal factor, cannot be omitted. PMID:23548412

  10. Determination of selected biogenic amines in Acacia rigidula plant materials and dietary supplements using LC-MS/MS methods.

    PubMed

    Pawar, Rahul S; Grundel, Erich; Fardin-Kia, Ali Reza; Rader, Jeanne I

    2014-01-01

    Extracts of Acacia rigidula leaves are used in weight-loss products sold in vitamin shops and over the internet with little or no published data about their potential biological effects. In our chemical investigations on authenticated A. rigidula plant material, we established a rapid and sensitive LC-MS/MS method for the quantitative determination of several phenethylamine, tyramine and tryptamine derivatives. Stable isotopically labeled compounds were used as internal standards for quantitative analysis. We found total calculated contents of 6 biogenic amines in A. rigidula leaf of 18.6 and 32.9μg/g. The content of selected amines in 21 dietary supplements labeled as containing A. rigidula was determined by a second LC-MS/MS method. Our study revealed significant differences in the amine profiles of authenticated plant materials and dietary supplements. β-Methylphenethylamine, a non-natural compound, was found in 9 of the 21 dietary supplement products. β-Methylphenethylamine was found at levels of 960-60,500μg/g while phenethylamine was found at levels of 710-171,620μg/g. β-Methylphenethylamine is a positional isomer of amphetamine and our results showed that it can be misidentified as amphetamine during LC-MS analysis. An independent GC-MS analysis was used to confirm the presence of β-methylphenethylamine and the absence of amphetamine in dietary supplements labeled as containing A. rigidula. This study demonstrates that confirmations by independent analytical methods are essential to verify findings of unusual or unexpected compounds in dietary supplements.

  11. Two Dimensional Polyamides Prepared From Unsaturated Carboxylic Acids And Amines.

    DOEpatents

    McDonald, William F.; Huang, Zhi Heng; Wright, Stacy C.; Danzig, Morris; Taylor, Andrew C.

    2002-07-17

    A polyamide and a process for preparing the polyamide are disclosed. The process comprises reacting in a reaction mixture a monomer selected from unsaturated carboxylic acids, esters of unsaturated carboxylic acids, anhydrides of unsaturated carboxylic acids, and mixtures thereof, and a first amine to form an intermediate reaction product in the reaction mixture, wherein the first amine is selected from RR.sub.1 NH, RNH.sub.2, RR.sub.1 NH.sub.2.sup.+, RNH.sub.3.sup.+ and mixtures thereof, wherein R and R.sub.1 can be the same or different and each contain between about 1 and 50 carbon atoms and are optionally substituted with heteroatoms oxygen, nitrogen, sulfur, and phosphorus and combinations thereof, and reacting the intermediate reaction product and a second amine to form a polyamide, wherein the second amine is selected from R.sub.2 R.sub.3 NH, R.sub.2 NH.sub.2, R.sub.2 R.sub.3 NH.sub.2.sup.+, R.sub.2 NH.sub.3.sup.+ and mixtures thereof wherein R.sub.2 and R.sub.3 can be the same or different and each contain between about 1 and 50 carbon atoms and are optionally substituted with heteroatoms oxygen, nitrogen, sulfur, and phosphorus and combinations thereof, wherein multiple of the R, R.sub.1, R.sub.2, and R.sub.3 are in vertically aligned spaced relationship along a backbone formed by the polyamide. In one version of the invention, the monomer is selected from maleic anhydride, maleic acid esters, and mixtures thereof. In another version of the invention, the first amine is an alkylamine, such as tetradecylamine, and the second amine is a polyalkylene polyamine, such as pentaethylenehexamine. In yet another version of the invention, the first amine and the second amine are olefinic or acetylenic amines, such as the reaction products of an alkyldiamine and an acetylenic carboxylic acid. The first amine and the second amine may be the same or different depending on the desired polyamide polymer structure.

  12. Effect of spermidine and its metabolites on the activity of pea seedlings diamine oxidase and the problems of biosensing of biogenic amines with this enzyme.

    PubMed

    Kivirand, K; Sõmerik, H; Oldekop, M-L; Rebane, R; Rinken, T

    2016-01-01

    Spermidine is one of the several biogenic amines, produced during the microbial decarboxylation of proteins. Individual biogenic amines in the formed mixtures are frequently analyzed with oxygen sensor based biosensors, as their content serves as a good biomarker for the determination of food quality. In these biosensors, diamine oxidase from pea seedlings (PSAO), catalyzing the oxidation of various biogenic amines by dissolved oxygen is commonly used for the bio-recognition of amines. However, in the presence of spermidine and/or its metabolite 1,3-diaminopropane, the activity of PSAO and the sensitivity of PSAO-based biosensors decrease due to inhibition. The inhibition constant of soluble spermidine, acting as an inhibiting substrate toward PSAO, was found to be (40±15) mM in freshly prepared solution and (0.28±0.05) mM in solution, incubated 30 days at room temperature. The inhibition constant of 1,3-diaminopropane, acting as a competitive inhibitor, was (0.43±0.12) mM as determined through the oxidation reaction of cadaverine. The metabolic half-life of soluble spermidine was 7 days at room temperature and 186 days at 4 °C. The kinetic measurements were carried out with an oxygen sensor; the composition of the solution of degraded spermidine was analyzed with MS.

  13. High-performance liquid chromatographic analysis of biogenic amines in pharmaceutical products containing Citrus aurantium.

    PubMed

    Viana, Carine; Zemolin, Gabriela M; Lima, Fernanda O; de Carvalho, Leandro M; Bottoli, Carla B G; Limberger, Renata Pereira

    2013-01-01

    A reverse-phase (RP)-HPLC method is reported for determining L-tyrosine, p-octopamine, synephrine, tyramine and hordenine as chemical markers of the species Citrus aurantium in raw material, dry extracts and phytotherapeutic herbal formulations. Using RP-HPLC with diode array detection (DAD) and gradient elution, the amines were determined in 12 different products from different Brazilian states labelled as containing C. aurantium. The presence of the amines was confirmed by mass spectrometry using electrospray ionisation (ESI-MS/MS). This RP-HPLC method allowed the separation of the amines from complex mixtures containing caffeine, ephedrine, salicin and other raw materials (e.g. Garcinia camboja, Phaseolus vulgaris, Caralluma fimbriata, Cassia nomane, Ephedra sp. and Cordia ecalyculata). The method proved useful and selective for inspecting herbal medicines containing p-synephrine and structural analogues. The herbal products analysed had a p-synephrine content ranging from 0.005 to 4.0% (w/w). PMID:23574611

  14. Dissolving Carboxylic Acids and Primary Amines on the Overhead Projector

    ERIC Educational Resources Information Center

    Solomon, Sally D.; Rutkowsky, Susan A.

    2010-01-01

    Liquid carboxylic acids (or primary amines) with limited solubility in water are dissolved by addition of aqueous sodium hydroxide (or hydrochloric acid) on the stage of an overhead projector using simple glassware and very small quantities of chemicals. This effective and colorful demonstration can be used to accompany discussions of the…

  15. Biogenic amine profile in unripe Arabica coffee beans processed according to dry and wet methods.

    PubMed

    Dias, Eduardo C; Pereira, Rosemary G F A; Borém, Flávio M; Mendes, Eulália; de Lima, Renato R; Fernandes, José O; Casal, Susana

    2012-04-25

    Immature coffee fruit processing contributes to a high amount of defective beans, which determines a significant amount of low-quality coffee sold in the Brazilian internal market. Unripe bean processing was tested, taking the levels of bioactive amines as criteria for evaluating the extent of fermentation and establishing the differences between processing methods. The beans were processed by the dry method after being mechanically depulped immediately after harvest or after a 12 h resting period in a dry pile or immersed in water. Seven bioactive amines were quantified: putrescine, spermine, spermidine, serotonin, cadaverine, histamine, and tyramine, with global amounts ranging from 71.8 to 80.3 mg/kg. The levels of spermine and spermidine were lower in the unripe depulped coffee than in the natural coffee. The specific conditions of dry and wet processing also influenced cadaverine levels, and histamine was reduced in unripe depulped coffee. A resting period of 12 h does not induce significant alteration on the beans and can be improved if performed in water. These results confirm that peeling immature coffee can decrease fermentation processes while providing more uniform drying, thus reducing the number of defects and potentially increasing beverage quality. PMID:22429054

  16. Ion-pair assisted extraction followed by (1)H NMR determination of biogenic amines in food and biological matrices.

    PubMed

    Chatzimitakos, T; Exarchou, V; Ordoudi, S A; Fiamegos, Y; Stalikas, C

    2016-07-01

    A selective method for the extraction and determination of six biogenic amines (BAs) by NMR is presented. Briefly, BAs are extracted into an organic solvent via the use of an ion pairing agent, followed by a back extraction in D2O in order to acquire the (1)H NMR spectra. The method is studied with respect to the critical experimental parameters and is successfully applied to selected food substrates (dark chocolate, banana, gouda cheese) and biological samples (urine and blood plasma) signifying its potential as an alternative tool for BAs determination. Accurate and precise results are consistently achieved with all matrixes studied. The calculated limits of detection and limits of quantitation were found to be in the ranges 0.05-0.13μg/mL and 0.14-0.38μg/mL, respectively, for biological samples while for food samples they were in the ranges 2.25-6.25μg/g and 6.75-18.7μg/g, respectively. PMID:26920317

  17. Separation of Key Biogenic Amines by Capillary Electrophoresis and Determination of Possible Indicators of Sport Fatigue in Athlete's Urine.

    PubMed

    He, Lili; Ren, Jie; Shi, Zhihao; Xu, Zhongqi

    2016-09-01

    This article aims to build up a simple, rapid and accurate capillary zone electrophoresis (CZE) method for the separation of biogenic amines (BAs). Here, 10 key BAs (phenethylamine, histamine, tryptamine, tyramine, 5-hydroxytryptamine, octopamine, dopamine, norepinephrine, epinephrine and carnosine) owning significant functions were chosen for method development. The baseline separation and identification of 10 standards of the mixture by CZE were eventually achieved in 150.0 mmol/L phosphate buffer (Na2HPO4-NaH2PO4) containing 1.0 mmol/L borax at a pH of 6.1. The addition of borax was found effective for improving the isomeric separation of octopamine and dopamine. The proposed method allowed the limits of detections of BAs to be in the range of 0.2-1.2 µmol/L at UV detection (200 nm); the relative standard deviation of the migration time and the peak area were in the ranges 0.08-0.12 and 2.74-4.63% (n = 5), respectively. Formaldehyde (a possible antiseptic in urine) and five main matrices in urine were studied for the identification of BAs. Finally, profiling of BAs in actual urine from athletes was carried out. Currently, only phenethylamine, norepinephrine and carnosine were designated by spiking the standards. In addition, their variation in athletes' urine has been checked at different states of sport fatigue with the goal of obtaining possible indicators of sport fatigue. PMID:27139740

  18. Biogenic amine production by the wine Lactobacillus brevis IOEB 9809 in systems that partially mimic the gastrointestinal tract stress

    PubMed Central

    2012-01-01

    Background Ingestion of fermented foods containing high levels of biogenic amines (BA) can be deleterious to human health. Less obvious is the threat posed by BA producing organisms contained within the food which, in principle, could form BA after ingestion even if the food product itself does not initially contain high BA levels. In this work we have investigated the production of tyramine and putrescine by Lactobacillus brevis IOEB 9809, of wine origin, under simulated gastrointestinal tract (GIT) conditions. Results An in vitro model that simulates the normal physiological conditions in the human digestive tract, as well as Caco-2 epithelial human cell lines, was used to challenge L. brevis IOEB 9809, which produced both tyramine and putrescine under all conditions tested. In the presence of BA precursors and under mild gastric stress, a correlation between enhancement of bacterial survival and a synchronous transcriptional activation of the tyramine and putrescine biosynthetic pathways was detected. High levels of both BA were observed after exposure of the bacterium to Caco-2 cells. Conclusions L. brevis IOEB 9809 can produce tyramine and putrescine under simulated human digestive tract conditions. The results indicate that BA production may be a mechanism that increases bacterial survival under gastric stress. PMID:23113922

  19. Separation of Key Biogenic Amines by Capillary Electrophoresis and Determination of Possible Indicators of Sport Fatigue in Athlete's Urine.

    PubMed

    He, Lili; Ren, Jie; Shi, Zhihao; Xu, Zhongqi

    2016-09-01

    This article aims to build up a simple, rapid and accurate capillary zone electrophoresis (CZE) method for the separation of biogenic amines (BAs). Here, 10 key BAs (phenethylamine, histamine, tryptamine, tyramine, 5-hydroxytryptamine, octopamine, dopamine, norepinephrine, epinephrine and carnosine) owning significant functions were chosen for method development. The baseline separation and identification of 10 standards of the mixture by CZE were eventually achieved in 150.0 mmol/L phosphate buffer (Na2HPO4-NaH2PO4) containing 1.0 mmol/L borax at a pH of 6.1. The addition of borax was found effective for improving the isomeric separation of octopamine and dopamine. The proposed method allowed the limits of detections of BAs to be in the range of 0.2-1.2 µmol/L at UV detection (200 nm); the relative standard deviation of the migration time and the peak area were in the ranges 0.08-0.12 and 2.74-4.63% (n = 5), respectively. Formaldehyde (a possible antiseptic in urine) and five main matrices in urine were studied for the identification of BAs. Finally, profiling of BAs in actual urine from athletes was carried out. Currently, only phenethylamine, norepinephrine and carnosine were designated by spiking the standards. In addition, their variation in athletes' urine has been checked at different states of sport fatigue with the goal of obtaining possible indicators of sport fatigue.

  20. Determination of biogenic amines in wines by pre-column derivatization and high-performance liquid chromatography coupled to mass spectrometry.

    PubMed

    García-Villar, Natividad; Hernández-Cassou, Santiago; Saurina, Javier

    2009-09-01

    A new HPLC method for determining biogenic amines in wines is developed. This method is based on pre-column amine derivatization, further separation of derivatives and on-line hyphenation of HPLC to atmospheric pressure chemical ionization mass spectrometry (APCI-MS). Biogenic amines have been derivatized with 1,2-naphthoquinone-4-sulfonate at 65 degrees C and pH 9.2 for 5 min. The separation of derivatives has been accomplished in a C(18) analytical column using an elution gradient based on increasing the percentage of methanol. Derivatives have been ionized in positive mode and detected by selected ion monitoring. The operating conditions of the APCI-MS system (voltages, temperatures and gases) have been thoroughly optimized to obtain the maximum sensitivity for all analytes. In the selected conditions, APCI-MS spectra display little fragmentation and good signal-to-noise ratio. Depending on the amine characteristics, the main spectral peaks are due to mono- and di-derivative products. Figures of merit of the method have been established under the selected conditions using red wine samples. Recoveries ranging from 94% to 106% have been obtained which prove excellent accuracy of the method in the determination of histamine, putrescine, cadaverine, tryptamine, phenylethylamine, tyramine and serotonin in red wines. The proposed method has been applied to the analysis of commercial wines from different Spanish regions.

  1. 40 CFR 721.5465 - Amine salt of organic acid (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Amine salt of organic acid (generic... Substances § 721.5465 Amine salt of organic acid (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as amine salt of organic acid...

  2. 40 CFR 721.5465 - Amine salt of organic acid (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Amine salt of organic acid (generic... Substances § 721.5465 Amine salt of organic acid (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as amine salt of organic acid...

  3. 40 CFR 721.5465 - Amine salt of organic acid (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Amine salt of organic acid (generic... Substances § 721.5465 Amine salt of organic acid (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as amine salt of organic acid...

  4. 40 CFR 721.5465 - Amine salt of organic acid (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Amine salt of organic acid (generic... Substances § 721.5465 Amine salt of organic acid (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as amine salt of organic acid...

  5. 40 CFR 721.5465 - Amine salt of organic acid (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Amine salt of organic acid (generic... Substances § 721.5465 Amine salt of organic acid (generic). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as amine salt of organic acid...

  6. 40 CFR 721.3625 - Fatty acid amine salt (generic name).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Fatty acid amine salt (generic name... Substances § 721.3625 Fatty acid amine salt (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as fatty acid amine salt (PMN...

  7. 40 CFR 721.3625 - Fatty acid amine salt (generic name).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Fatty acid amine salt (generic name... Substances § 721.3625 Fatty acid amine salt (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as fatty acid amine salt (PMN...

  8. 40 CFR 721.3625 - Fatty acid amine salt (generic name).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Fatty acid amine salt (generic name... Substances § 721.3625 Fatty acid amine salt (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as fatty acid amine salt (PMN...

  9. 40 CFR 721.3625 - Fatty acid amine salt (generic name).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Fatty acid amine salt (generic name... Substances § 721.3625 Fatty acid amine salt (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as fatty acid amine salt (PMN...

  10. 40 CFR 721.3625 - Fatty acid amine salt (generic name).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Fatty acid amine salt (generic name... Substances § 721.3625 Fatty acid amine salt (generic name). (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as fatty acid amine salt (PMN...

  11. A new test procedure for biogenic sulfuric acid corrosion of concrete

    PubMed

    Vincke; Verstichel; Monteny; Verstraete

    1999-01-01

    A new test method is described for biogenic sulfuric acid corrosion of concrete, more specifically in sewer conditions. The aim of the new test method is the development of an accelerated and reproducible procedure for monitoring the resistance of different types of concrete with regard to biogenic sulfuric acid corrosion. This experimental procedure reflects worst case conditions by providing besides H2S, also an enrichment of thiobacilli and biologically produced sulfur. By simulating the cyclic processes occurring in sewer pipes, significant differences between concrete mixtures could be detected after 51 days. Concrete modified by a styrene-acrylic ester polymer demonstrated a higher resistance against biogenic sulfuric acid attack. PMID:11068828

  12. A new test procedure for biogenic sulfuric acid corrosion of concrete

    PubMed

    Vincke; Verstichel; Monteny; Verstraete

    1999-01-01

    A new test method is described for biogenic sulfuric acid corrosion of concrete, more specifically in sewer conditions. The aim of the new test method is the development of an accelerated and reproducible procedure for monitoring the resistance of different types of concrete with regard to biogenic sulfuric acid corrosion. This experimental procedure reflects worst case conditions by providing besides H2S, also an enrichment of thiobacilli and biologically produced sulfur. By simulating the cyclic processes occurring in sewer pipes, significant differences between concrete mixtures could be detected after 51 days. Concrete modified by a styrene-acrylic ester polymer demonstrated a higher resistance against biogenic sulfuric acid attack.

  13. Extraction Efficiency of Different Solvents and LC-UV Determination of Biogenic Amines in Tea Leaves and Infusions

    PubMed Central

    Spizzirri, U. Gianfranco; Picci, Nevio

    2016-01-01

    Biogenic amines (BAs), that is, spermine, spermidine, putrescine, histamine, tyramine, β-phenylethylamine, cadaverine, and serotonin, have been determined in several samples of tea leaves, tea infusions, and tea drinks by LC-UV method after derivatization with dansyl chloride. Different extraction solvents have been tested and TCA 5% showed better analytical performances in terms of linearity, recovery percentages, LOD, LOQ, and repeatability than HCl 0.1 M and HClO4 0.1 M and was finally exploited for the quantitative determination of BAs in all samples. In tea leaves total BAs concentration ranged from 2.23 μg g−1 to 11.24 μg g−1 and PUT (1.05–2.25 μg g−1) and SPD (1.01–1.95 μg g−1) were always present, while SER (nd–1.56 μg g−1), HIS (nd–2.44 μg g−1), and SPM (nd–1.64 μg g−1) were detected more rarely. CAD and PHE were determined in few samples at much lower concentrations while none of the samples contained TYR. Tea infusions showed the same trend with total BAs concentrations never exceeding 80.7 μg L−1. Black teas showed higher amounts of BAs than green teas and organic and decaffeinated samples always contained much lower BAs levels than their conventional counterparts. PMID:27555979

  14. Antibiotic resistance, virulence determinants and production of biogenic amines among enterococci from ovine, feline, canine, porcine and human milk

    PubMed Central

    2013-01-01

    Background Recent studies have shown that mammalian milk represents a continuous supply of commensal bacteria, including enterococci. The objectives of this study were to evaluate the presence of enterococci in milk of different species and to screen them for several genetic and phenotypic traits of clinical significance among enterococci. Results Samples were obtained from, at least, nine porcine, canine, ovine, feline and human healthy hosts. Enterococci could be isolated, at a concentration of 1.00 × 102 -1.16 × 103 CFU/ml, from all the porcine samples and, also from 85, 50, 25 and 25% of the human, canine, feline and ovine ones, respectively. They were identified as Enterococcus faecalis, Enterococcus faecium, Enterococcus hirae, Enterococcus casseliflavus and Enterococcus durans. Among the 120 initial enterococcal isolates, 36 were selected on the basis of their different PFGE profiles and further characterized. MLST analysis revealed a wide diversity of STs among the E. faecalis and E. faecium strains, including some frequently associated to hospital infections and novel STs. All the E. faecalis strains possessed some of the potential virulence determinants (cad, ccf, cob, cpd, efaAfs, agg2, gelE, cylA, espfs) assayed while the E. faecium ones only harboured the efaAfm gene. All the tested strains were susceptible to tigecycline, linezolid and vancomycin, and produced tyramine. Their susceptibility to the rest of the antimicrobials and their ability to produce other biogenic amines varied depending on the strain. Enterococci strains isolated from porcine samples showed the widest spectrum of antibiotic resistance. Conclusions Enterococci isolated from milk of different mammals showed a great genetic diversity. The wide distribution of virulence genes and/or antibiotic resistance among the E. faecalis and E. faecium isolates indicates that they can constitute a reservoir of such traits and a risk to animal and human health. PMID:24325647

  15. [Reactivity of the adenylyl cyclase system in rat tissues to biogenic amines and peptide hormones under starvation condition].

    PubMed

    Shpakov, A O; Kuznetsova, L A; Plesneva, S A; Pertseva, M N

    2007-04-01

    Under starvation condition, sensitivity of the adenylyl cyclase system to regulatory action of biogenic amines and peptide hormones in rat tissues are changed. In the myocardium and skeletal muscles, after 2 and 4 days of starvation, the regulatory effects of isoproterenol and relaxin acting via G,-proteins on the adenylyl cyclase activity and the G-protein GTP-binding are significantly increased compared with control. At the same time, regulatory effects ofsomatostatin which are realized via Gi-proteins, on adenylyl cyclase system in the myocardium are decreased. Under prolonged starvation consisting of two consecutive 4-days periods, the effects of hormones acting via Gs-proteins on the adenylyl cyclase activity in muscle tissues are decreased to control value levels. The effects of hormones acting via Gi-proteins are largely reduced. In the brain, intensification of adenylyl cyclase stimulating hormonal effects was late and only observed after a 4-day starvation. Unlike muscle tissues, the increase of adenylyl cyclase stimulating effects in the brain is preserved after two-period starvation. The weakening of adenylyl cyclase inhibiting hormonal signals both in the brain and muscles is observed after a 2-day starvation and then the weakening is intensified. Possible role of glucose level and basal adenylyl cyclase activity in determination of the sensitivity of the adenylyl cyclase system to hormones under study is discussed. It is suggested that one of the key causes of physiological changes in animal organism under starvation involves alteration of hormonal signalling systems sensitivity, in particular that of the adenylyl cyclase system, to hormone regulatory action.

  16. Effect of acute and chronic cholinesterase inhibition on biogenic amines in rat brain.

    PubMed

    Soininen, H; Unni, L; Shillcutt, S

    1990-12-01

    The effects of five cholinesterase inhibitors on forebrain monoamine and their metabolite levels, and on forebrain and plasma cholinesterase (ChE) activity in rat were studied in acute and chronic conditions. Acute tetrahydroaminoacridine (THA) dosing caused lower brain (68%) and higher plasma (90%) ChE inhibition than the other drugs studied and increased levels of brain dihydroxyphenylacetic acid (DOPAC) (236%), homovanillic acid (HVA) (197%) and 5-hydroxyindoleacetic acid (5-HIAA) (130%). Acute physostigmine (PHY) administration caused a 215% increase in brain DOPAC content. Despite high brain ChE inhibition induced by metrifonate (MTF), dichlorvos (DDVP) or naled no changes in brain noradrenaline (NA), dopamine (DA) or serotonin (5-HT) occurred due to treatment with the study drugs in the acute study. In the chronic 10-day study THA or PHY caused no substantial ChE inhibition in brain when measured 18 hours after the last dose, whereas MTF induced 74% ChE inhibition. Long-term treatment with THA or MTF caused no changes in monoamine levels, but PHY treatment resulted in slightly increased 5-HT values. These results suggest that MTF, DDVP and naled seem to act solely by cholinergic mechanisms. However, the central neuropharmacological mechanism of action of THA and PHY may involve changes in cholinergic as well as dopaminergic and serotoninergic systems. PMID:1711162

  17. Mutagenicity and genotoxicity of sorbic acid-amine reaction products.

    PubMed

    Ferrand, C; Marc, F; Fritsch, P; Cassand, P; de Saint Blanquat, G

    2000-11-01

    Sorbic acid (E200) and its salts (potassium and calcium sorbate: E202 and E203) are allowed for use as preservatives in numerous processed foods. Sorbic acid had a conjugated system of double bonds which makes it susceptible to nucleophilic attack, sometimes giving mutagenic products. Under conditions typical of food processing (50-80 degrees C), we analysed the cyclic derivatives resulting from a double addition reaction between sorbic acid and various amines. Mutagenesis studies, involving Ames' test and genotoxicity studies with HeLa cells and plasmid DNA, showed that none of the products studied presented either mutagenic or genotoxic activities.

  18. An in situ derivatization - dispersive liquid-liquid microextraction combined with gas-chromatography - mass spectrometry for determining biogenic amines in home-made fermented alcoholic drinks.

    PubMed

    Płotka-Wasylka, Justyna; Simeonov, Vasil; Namieśnik, Jacek

    2016-07-01

    A novel dispersive liquid-liquid microextraction (DLLME) gas chromatography mass-spectrometry (GC-MS) method was developed for the determination of 13 biogenic amines in home-made wine samples. The method allows to simultaneous extraction and derivatization of the amines providing a simple and fast mode of extract enrichment. During the study, two different procedures were examined. Statistical analysis was performed to choose better procedure, as well as the conditions of derivatization reaction. At least, a mixture of methanol (dispersive solvent; 215μL), chloroform (extractive solvent; 400μL), and isobutyl choloroformate (derivatizing reagent; 90μL) was used as extractive/derivatizing reagent, added to 5mL of sample. The addition of mixture of pyridine and HCl was necessary to eliminate the by-products. The proposed method showed good linearity (correlation coefficients >0.9961), good recoveries (from 77 to 105%), and good intra-day precision (below 13%) and inter-day precision (below 10%). Moreover, detection limits were never over 4.1μg/L. The developed method was successfully applied to the analysis of 17 home-made wine samples not regulated by law. All of the biogenic amines analyzed were found in most of the wines.

  19. Arsenic removal from acidic solutions with biogenic ferric precipitates.

    PubMed

    Ahoranta, Sarita H; Kokko, Marika E; Papirio, Stefano; Özkaya, Bestamin; Puhakka, Jaakko A

    2016-04-01

    Treatment of acidic solution containing 5g/L of Fe(II) and 10mg/L of As(III) was studied in a system consisting of a biological fluidized-bed reactor (FBR) for iron oxidation, and a gravity settler for iron precipitation and separation of the ferric precipitates. At pH 3.0 and FBR retention time of 5.7h, 96-98% of the added Fe(II) precipitated (99.1% of which was jarosite). The highest iron oxidation and precipitation rates were 1070 and 28mg/L/h, respectively, and were achieved at pH 3.0. Subsequently, the effect of pH on arsenic removal through sorption and/or co-precipitation was examined by gradually decreasing solution pH from 3.0 to 1.6 (feed pH). At pH 3.0, 2.4 and 1.6, the highest arsenic removal efficiencies obtained were 99.5%, 80.1% and 7.1%, respectively. As the system had ferric precipitates in excess, decreased arsenic removal was likely due to reduced co-precipitation at pH<2.4. As(III) was partially oxidized to As(V) in the system. In shake flask experiments, As(V) sorbed onto jarosite better than As(III). Moreover, the sorption capacity of biogenic jarosite was significantly higher than that of synthetic jarosite. The developed bioprocess simultaneously and efficiently removes iron and arsenic from acidic solutions, indicating potential for mining wastewater treatment. PMID:26705889

  20. Amine bearing polymeric particles as acid neutralizers for engine oils

    SciTech Connect

    Theodore, A.N.; Chattha, M.S.

    1986-02-04

    This patent describes a lubricating oil composition consisting of a major proportion of a lubricating base oil and about 0.1 to 15 weight percent of an acid neutralizing additive which consists of polymer particles (a) bearing pendant amine groups, and (b) having a diameter of about 500 A and 10,000 A. The amine functional particles are formed by reacting polymer particles bearing pendant epoxide groups with a secondary amine in an amount so as to react essentially all of the epoxide groups on the epoxide bearing polymer particles with the secondary amine. The polymer particles bearing pendant epoxide groups are formed by the free radical addition polymerization of: (a) between about 50 and about 100 weight percent of an ethylenically unsaturated monomers bearing an epoxide group, and (b) 0 up to about 50 weight percent of other monoethylenically unsaturated monomers; in the presence of: (I) a non-polar organic liquid which is a solvent for the polymerizable monomers, but a non-solvent for the resultant polymer, and (II) polymeric dispersion stabilizer containing at least two segments, with one segment being solvated by the non-polar organic liquid and the second segment being of different polarity than the first segment and relatively insoluble in the non-polar organic liquid. The second segment of the stabilizer is chemically attached to the polymerized particle.

  1. [Structural and functional characteristics of the adenylyl cyclase signaling system regulated by biogenic amines and peptide hormones in the muscle of a worm Lumbricus terrestris].

    PubMed

    Shpakov, A O; Shpakova, E A; Kuznetsova, L A; Plesneva, S A; Pertseva, M N

    2008-01-01

    It has been shown for the first time that biogenic amines (catecholamines and tryptophane derivatives) stimulate dose-dependently activity of adenylyl cyclase (AC) and GTP-binding of G-proteins in muscle of the cutaneous-muscle bag of the earthworm Lumbricus terrestris. By efficiency of their stimulating action on the AC activity, biogenic amines can be arranged in the following sequence: octopamine > tyramine > tryptamine = serotonin > dopamine > isoproterenol = adrenalin. The sequence of efficiency of their action on GTP-binding is somewhat different: serotonin > tryptamine > octopamine > dopamine = tyramine > adrenaline > isoproterenol. Sensitivity of AC and G-proteins in the worm muscle to biogenic amines is similar with that in smooth muscle of the molluse Anodonta cygnea (invertebrates), but differs markedly by this parameter from the rat myocardium (vertebrates). It has also been revealed that AC in the worm muscle is regulated by peptide hormones relaxin and somatostatin whose action is comparable with that in the mollusk muscle, but much weaker that the action of these hormones on the rat myocardium AC activity. Use of C-terminal peptides of alpha-subunits of G-proteins of the stimulatory (385-394 Galpha(s)) and inhibitory (346-355 Galpha(i2)) types that disrupt selectively the hormonal signal transduction realized via G(s)- and G(i)-proteins, respectively, allowed establishing that the AC-stimulating effects of relaxin, octopamine, tyramine, and dopamine in the worm muscle are realized via the receptors coupled functionally with G(s)-protein; the AC-inhibiting effect of somatostatin is realized via the receptor coupled with G(i)-protein, whereas serotonin and tryptamine activate both types of G-proteins. PMID:18959208

  2. Formation of histamine and biogenic amines in cold-smoked tuna: an investigation of psychrotolerant bacteria from samples implicated in cases of histamine fish poisoning.

    PubMed

    Emborg, Jette; Dalgaard, Paw

    2006-04-01

    Two outbreaks and a single case of histamine fish poisoning associated with cold-smoked tuna (CST) were reported in Denmark during 2004. The bacteria most likely responsible for histamine formation in CST implicated in histamine fish poisoning was identified for the first time in this study. Product characteristics and profiles of biogenic amines in the implicated products were also recorded. In the single poisoning case, psychrotolerant Morganella morganii-like bacteria most likely was responsible for the histamine production in CST with 2.2% +/- 0.6% NaCl in the water phase (WPS). In outbreak 1, Photobacterium phosphoreum most likely formed the histamine in CST with 1.3% +/- 0.1% WPS. In outbreak 2, which involved 10 persons, the bacteria responsible for histamine formation could not be determined. The measured concentrations of WPS were very low compared with those of randomly collected commercial samples of CST and cold-smoked blue marlin (4.1 to 12.7% WPS). Challenge tests at 5 degrees C with psychrotolerant M. morganii and P. phosphoreum in CST with 4.4% WPS revealed growth and toxic histamine formation by the psychrotolerant M. morganii-like bacteria but not by P. phosphoreum. In a storage trial with naturally contaminated CST containing 6.9% WPS, lactic acid bacteria dominated the microbiota, and no significant histamine formation was observed during the shelf life of about 40 days at 5 degrees C and of about 16 days at 10 degrees C. To prevent toxic histamine formation, CST should be produced with >5% WPS and distributed with a declared 5 degrees C shelf life of 3 to 4 weeks or less.

  3. Novel and sensitive reversed-phase high-pressure liquid chromatography method with electrochemical detection for the simultaneous and fast determination of eight biogenic amines and metabolites in human brain tissue.

    PubMed

    Van Dam, Debby; Vermeiren, Yannick; Aerts, Tony; De Deyn, Peter Paul

    2014-08-01

    A fast and simple RP-HPLC method with electrochemical detection (ECD) and ion pair chromatography was developed, optimized and validated in order to simultaneously determine eight different biogenic amines and metabolites in post-mortem human brain tissue in a single-run analytical approach. The compounds of interest are the indolamine serotonin (5-hydroxytryptamine, 5-HT), the catecholamines dopamine (DA) and (nor)epinephrine ((N)E), as well as their respective metabolites, i.e. 3,4-dihydroxyphenylacetic acid (DOPAC) and homovanillic acid (HVA), 5-hydroxy-3-indoleacetic acid (5-HIAA) and 3-methoxy-4-hydroxyphenylglycol (MHPG). A two-level fractional factorial experimental design was applied to study the effect of five experimental factors (i.e. the ion-pair counter concentration, the level of organic modifier, the pH of the mobile phase, the temperature of the column, and the voltage setting of the detector) on the chromatographic behaviour. The cross effect between the five quantitative factors and the capacity and separation factors of the analytes were then analysed using a Standard Least Squares model. The optimized method was fully validated according to the requirements of SFSTP (Société Française des Sciences et Techniques Pharmaceutiques). Our human brain tissue sample preparation procedure is straightforward and relatively short, which allows samples to be loaded onto the HPLC system within approximately 4h. Additionally, a high sample throughput was achieved after optimization due to a total runtime of maximally 40min per sample. The conditions and settings of the HPLC system were found to be accurate with high intra and inter-assay repeatability, recovery and accuracy rates. The robust analytical method results in very low detection limits and good separation for all of the eight biogenic amines and metabolites in this complex mixture of biological analytes.

  4. Approaches for regeneration of amine-carboxylic acid extracts

    SciTech Connect

    Dai, Y.; King, C.J.

    1995-07-01

    Extraction processes based on reversible chemical complexation can be useful for separation of polar organics from dilute solution. Tertiary amines are effective extractants for the recovery of carboxylic acids from aqueous solution. The regeneration of aminecarboxylic acid extracts is an important step which strongly influences the economic viability of the separation process. Several regeneration methods are critically reviewed, and the factors that affect swing regeneration processes, including temperature-swing, diluent composition-swing and pH-swing with a volatile base are discussed. Interest in this area comes from interest in treatment of waste streams, particularly in petrochemical and fermentation manufacture.

  5. 40 CFR 721.7770 - Alkylphenoxypoly(oxyethylene) sulfuric acid ester, substituted amine salt.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... ester, substituted amine salt. (a) Chemical substance and significant new uses subject to reporting. (1... amine salt (PMN P-92-396) is subject to reporting under this section for the significant new uses... acid ester, substituted amine salt. 721.7770 Section 721.7770 Protection of Environment...

  6. 40 CFR 721.7770 - Alkylphenoxypoly(oxyethylene) sulfuric acid ester, substituted amine salt.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... ester, substituted amine salt. (a) Chemical substance and significant new uses subject to reporting. (1... amine salt (PMN P-92-396) is subject to reporting under this section for the significant new uses... acid ester, substituted amine salt. 721.7770 Section 721.7770 Protection of Environment...

  7. 40 CFR 721.7770 - Alkylphenoxypoly(oxyethylene) sulfuric acid ester, substituted amine salt.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... ester, substituted amine salt. (a) Chemical substance and significant new uses subject to reporting. (1... amine salt (PMN P-92-396) is subject to reporting under this section for the significant new uses... acid ester, substituted amine salt. 721.7770 Section 721.7770 Protection of Environment...

  8. 40 CFR 721.7770 - Alkylphenoxypoly(oxyethylene) sulfuric acid ester, substituted amine salt.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... acid ester, substituted amine salt. 721.7770 Section 721.7770 Protection of Environment ENVIRONMENTAL... ester, substituted amine salt. (a) Chemical substance and significant new uses subject to reporting. (1... amine salt (PMN P-92-396) is subject to reporting under this section for the significant new...

  9. Analytical approach to determining human biogenic amines and their metabolites using eVol microextraction in packed syringe coupled to liquid chromatography mass spectrometry method with hydrophilic interaction chromatography column.

    PubMed

    Konieczna, Lucyna; Roszkowska, Anna; Synakiewicz, Anna; Stachowicz-Stencel, Teresa; Adamkiewicz-Drożyńska, Elżbieta; Bączek, Tomasz

    2016-04-01

    Analysis of biogenic amines (BAs) in different human samples provides insight into the mechanisms of various biological processes, including pathological conditions, and thus may be very important in diagnosing and monitoring several neurological disorders and cancerous tumors. In this work, we developed a simple and fast procedure using a digitally controlled microextraction in packed syringe (MEPS) coupled to liquid chromatography mass spectrometry (LC-MS) method for simultaneous determination of biogenic amines, their precursors and metabolites in human plasma and urine samples. The separation of 12 low molecular weight and hydrophilic molecules with a wide range of polarities was achieved with hydrophilic interaction chromatography (HILIC) column without derivatization step in 12 min. MEPS was implemented using the APS sorbent in semi-automated analytical syringe (eVol(®)) and small volume of urine and plasma samples, 5 0µL and 100 μL, respectively. We evaluated important parameters influencing MEPS efficiency, including stationary phase selection, sample pH and volume, number of extraction cycles, and washing and elution volumes. In optimized MEPS conditions, the analytes were eluted by 3 × 50 μL of methanol with 0.1% formic acid. The chromatographic separation of analytes was performed on XBridge Amide™ BEH analytical column (3.0mm × 100 mm, 3.5 µm) using gradient elution with mobile phase consisting of phase A: 10mM ammonium formate buffer in water pH 3.0 and phase B: 10mM ammonium formate buffer in acetonitrile pH 3.0. The LC-HILIC-MS method was validated and, in optimum conditions, presented good linearity in concentration range within 10-2000 ng/mL for all the analytes with a determination coefficient (r(2)) higher than 0.999 for plasma and urine samples. Method recovery ranged within 87.6-104.3% for plasma samples and 84.2-98.6% for urine samples. The developed method utilizing polar APS sorbent along with polar HILIC column was applied for

  10. Analytical approach to determining human biogenic amines and their metabolites using eVol microextraction in packed syringe coupled to liquid chromatography mass spectrometry method with hydrophilic interaction chromatography column.

    PubMed

    Konieczna, Lucyna; Roszkowska, Anna; Synakiewicz, Anna; Stachowicz-Stencel, Teresa; Adamkiewicz-Drożyńska, Elżbieta; Bączek, Tomasz

    2016-04-01

    Analysis of biogenic amines (BAs) in different human samples provides insight into the mechanisms of various biological processes, including pathological conditions, and thus may be very important in diagnosing and monitoring several neurological disorders and cancerous tumors. In this work, we developed a simple and fast procedure using a digitally controlled microextraction in packed syringe (MEPS) coupled to liquid chromatography mass spectrometry (LC-MS) method for simultaneous determination of biogenic amines, their precursors and metabolites in human plasma and urine samples. The separation of 12 low molecular weight and hydrophilic molecules with a wide range of polarities was achieved with hydrophilic interaction chromatography (HILIC) column without derivatization step in 12 min. MEPS was implemented using the APS sorbent in semi-automated analytical syringe (eVol(®)) and small volume of urine and plasma samples, 5 0µL and 100 μL, respectively. We evaluated important parameters influencing MEPS efficiency, including stationary phase selection, sample pH and volume, number of extraction cycles, and washing and elution volumes. In optimized MEPS conditions, the analytes were eluted by 3 × 50 μL of methanol with 0.1% formic acid. The chromatographic separation of analytes was performed on XBridge Amide™ BEH analytical column (3.0mm × 100 mm, 3.5 µm) using gradient elution with mobile phase consisting of phase A: 10mM ammonium formate buffer in water pH 3.0 and phase B: 10mM ammonium formate buffer in acetonitrile pH 3.0. The LC-HILIC-MS method was validated and, in optimum conditions, presented good linearity in concentration range within 10-2000 ng/mL for all the analytes with a determination coefficient (r(2)) higher than 0.999 for plasma and urine samples. Method recovery ranged within 87.6-104.3% for plasma samples and 84.2-98.6% for urine samples. The developed method utilizing polar APS sorbent along with polar HILIC column was applied for

  11. Effects of on-board and dockside handling on the formation of biogenic amines in mahimahi (Coryphaena hippurus), skipjack tuna (Katsuwonus pelamis), and yellowfin tuna (Thunnus albacares).

    PubMed

    Staruszkiewicz, Walter F; Barnett, James D; Rogers, Patricia L; Benner, Ronald A; Wong, Lynn L; Cook, John

    2004-01-01

    Consumer illnesses by scombroid poisonings have been a continuing problem for many years. The intoxications follow the ingestion of fish such as tuna and mahimahi that have undergone bacterial decomposition, leading to the formation of biogenic amines. Research studies have concluded that histamine is one of the indicators of scombrotoxic fish and that other amines, such as cadaverine, could be involved in the illnesses. Guidance for the handling of fish on board fishing vessels to prevent the production of scombrotoxic fish has been limited by a lack of data addressing changes that occur in fish from the water to delivery at dockside. In this study, the changes in selected biogenic amines were determined in mahimahi and tuna, which were captured and held in seawater at 25 to 35 degrees C for incubation times up to 18 h. The fillets from the treated fish were sectioned by transverse cuts and analyzed for histamine, cadaverine, and putrescine. Results showed that at 26 degrees C, more than 12 h of incubation were required before a histamine concentration of 50 ppm was reached in mahimahi. At 35 degrees C, 50 ppm histamine formed within 9 h. Similar results were found for skipjack and yellowfin tuna. Histamine concentrations exceeded 500 ppm within an additional 3 h of incubation in mahimahi. At both temperatures, an increase in the concentration of cadaverine preceded an increase in histamine levels. Changes in putrescine concentrations in the fish were less pronounced. The study also demonstrated that histidine decarboxylase activity was retained in some frozen samples of fish and could result in further increases in histamine on thawing. PMID:14717363

  12. 40 CFR 721.9620 - Aromatic sulfonic acid compound with amine.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Aromatic sulfonic acid compound with... Specific Chemical Substances § 721.9620 Aromatic sulfonic acid compound with amine. (a) Chemical substance... aromatic sulfonic acid compound with amine (PMN P-93-832) is subject to reporting under this section...

  13. 40 CFR 721.9620 - Aromatic sulfonic acid compound with amine.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Aromatic sulfonic acid compound with... Specific Chemical Substances § 721.9620 Aromatic sulfonic acid compound with amine. (a) Chemical substance... aromatic sulfonic acid compound with amine (PMN P-93-832) is subject to reporting under this section...

  14. 40 CFR 721.9620 - Aromatic sulfonic acid compound with amine.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Aromatic sulfonic acid compound with... Specific Chemical Substances § 721.9620 Aromatic sulfonic acid compound with amine. (a) Chemical substance... aromatic sulfonic acid compound with amine (PMN P-93-832) is subject to reporting under this section...

  15. 40 CFR 721.9620 - Aromatic sulfonic acid compound with amine.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Aromatic sulfonic acid compound with... Specific Chemical Substances § 721.9620 Aromatic sulfonic acid compound with amine. (a) Chemical substance... aromatic sulfonic acid compound with amine (PMN P-93-832) is subject to reporting under this section...

  16. 40 CFR 721.9620 - Aromatic sulfonic acid compound with amine.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Aromatic sulfonic acid compound with... Specific Chemical Substances § 721.9620 Aromatic sulfonic acid compound with amine. (a) Chemical substance... aromatic sulfonic acid compound with amine (PMN P-93-832) is subject to reporting under this section...

  17. In vitro synthesis of biogenic amines by Brochothrix thermosphacta isolates from meat and meat products and the influence of other microorganisms.

    PubMed

    Nowak, Agnieszka; Czyzowska, Agata

    2011-07-01

    Twenty Brochothrix thermosphacta strains tested for biogenic amines (BAs) production, formed histamine (6.6-16.2 mg/kg) and tyramine (18.7-35.4 mg/kg) but neither putrescine nor cadaverine. Six of the twenty strains were also investigated in respect of their influence on the synthesis of BAs by Escherichia coli, Pseudomonas sp., Proteus mirabilis and Lactobacillus sakei. In pure culture Escherichia coli produced all of the studied amines (histamine, tyramine, putrescine and cadaverine) with a total concentration of 167.7 mg/kg, P. mirabilis produced a total of 56.7 mg/kg histamine, tyramine and cadaverine, while Lactobacillus sakei and Pseudomonas sp. produced histamine and tyramine, totaling 37.9 and 35.2 mg/kg respectively. All B. thermosphacta promoted cadaverine production by Escherichia coli which increased by 12-68%, and some of them contributed to the appearance of this amine among the metabolites of Pseudomonas. The presence of B. thermosphacta decreased the potential ability of P. mirabilis to produce BAs.

  18. [Effect of chronic exposure to nitrogen dioxide on biogenic amine levels in the brain of guinea pigs].

    PubMed

    Felińska, W; Szkilnik, R; Stanosek, B; Kamiński, M; Ludyga, K; Brus, R

    1985-01-01

    The experiment was carried out on male guinea pigs exposed to NO2 at a constant concentration of 0.1 ppm 24 h daily for 1, 2.5 and 6 months, or NO2 concentration was increased to 0.5 ppm twice daily, between 7:00 and 8:00 AM and 4:00 and 5:00 PM. After the exposure to NO2 was over the animals were killed by decapitation. The cranium was opened and the brain removed, and afterwards at 0 degrees C the left hemisphere was dissected into discrete areas which were then frozen on dry ice and weighed. The tissues were kept for 2-3 days at -20 degrees C, and afterwards the content of noradrenaline, 5-hydroxytryptamine and 5-hydroxyindole-acetic acid was estimated spectrofluorometrically in examined parts of the brain (thalamus--hypothalamus pons + medulla oblongata hippocampus, cortex frontalis). It was shown that the applied NO2 concentrations brought about slight and nonspecific alterations in the content of the investigated amines in guinea pigs' brain.

  19. Biogenic acids produced on epoxy linings installed in sewer crown and tidal zones.

    PubMed

    Valix, M; Shanmugarajah, K

    2015-09-01

    In this study the biogenic acids generated by microbes on the surface of Bisphenol A epoxy mortar coupons were investigated for up to 30 months. The epoxy coupons were installed in six sewers in three city locations, Sydney, Melbourne and Perth. Coupons were installed in both the crown and the tidal zones of the sewers to capture the effect of location within the pipe on acid production. The coupons were retrieved approximately every 6 months to provide a dynamic analysis of the biogenic acid production. Our results reveal the colonisation of epoxy mortar by the more aggressive acidophilic bacteria occurred within six months to two years of their installation in the sewer pipes. Biogenic acid generation appear to occur homogeneously from the tidal zone to the crown of the sewer pipes. The reduction in the surface pH of the epoxy lining was supported by the successive growth of microbes beginning with fungi followed be neutrophilic and heterotrophic bacteria and finally by the acidophilic bacteria and the corresponding accumulation of organic and sulphuric acids attributed to these organisms. This study also revealed the potential inhibiting effects on the microbes induced by the accumulation of metabolic products on the epoxy surface. The accumulation of organic acids and H2S coincided with the growth and metabolism inhibition of fungi and acidophilic bacteria. These results provide insights into the microbial interaction and biogenic acids production that contribute to lining degradation and corrosion of concrete in sewer pipes.

  20. Biogenic arsenic volatilisation from an acidic wetland soil

    NASA Astrophysics Data System (ADS)

    Ilgen, Gunter; Huang, Jen-How; Lu, Shipeng; Tian, Liyan; Alewell, Christine

    2014-05-01

    Biogenic arsenic (As) volatilisation was budgeted at 26000 t yr-1as the largest input of the global As release into the atmosphere, thereby playing an important role in the biogeochemical cycle of As in the surface environment. In order to quantify As volatilisation from wetland soils and to elucidate the geochemical and microbiological factors governing As volatilisation, a series of incubations with an acidic wetland soil collected in NE-Bavaria in Germany were performed at 15oC for 4 months with addition of NaN3, arsenite (As(III)), FeCl3, NaSO4 and NaOAc with N2 and air in the headspace. Speciation of gaseous As in the headspace using GC-ICP-MS/ ESI-MS coupling showed the predominance of either arsine (AsH3) or trimethylarsine ((CH3)3As) in all treatments during the time course of incubation. Monomethylarsine ((CH3)AsH2) and dimethylarsine ((CH3)2AsH) could be only detected in trace amounts. Arsenic speciation in porewater with HPLC-ICP-MS revealed the predominance of As(III) and methylated As was never detectable. Arsenic volatilisation summed to 2.3 ng As (88% as AsH3) in the control incubations, which accounted for ~0.25 % of the total As storage in the wetland soil. Treatments with 10 mM NaN3 resulted in emission of only 0.03 ng As. In contrast, addition of 10 mM NaOAc stimulated microbial activities in wetland soils and subsequently rose As volatilisation to 8.5 ng As. It could be therefore concluded that As volatilisation from the wetland soils was mainly biological. Spiking 67 μM As(III) increased 10 times of As volatilisation and the proportion of methylated arsines increased to 66%, which is supposed to be caused by the largely enhanced As availability in porewater for microbes (480 ppb, ~65 times higher than those in the controls). Adding 10 mM FeCl3 stimulated microbial Fe(III) reducing activities but suppressed other microbial activities by lowering soil pH from 5 to 3.6, decreasing consequently As volatilisation to 0.3 ng As. The much lower redox

  1. Additive-free decarboxylative coupling of cinnamic acid derivatives in water: synthesis of allyl amines.

    PubMed

    Park, Kyungho; Lee, Sunwoo

    2015-03-01

    The first example of an additive-free decarboxylative coupling of cinnamic acid derivatives with formaldehyde and amines to afford the corresponding allyl amines is reported. This reaction is highly environmentally friendly because it was conducted in H2O and without any additives, releasing only CO2 and H2O as byproducts. This reaction showed a broad substrate scope including cyclic and acyclic amines and high functional group tolerance. Moreover, phenyl dienoic acid participated in this type of decarboxylative coupling reaction.

  2. Role of biogenic amines in the post-mortem migration of Anisakis pegreffii (Nematoda: Anisakidae Dujardin, 1845) larvae into fish fillets.

    PubMed

    Šimat, Vida; Miletić, Jelena; Bogdanović, Tanja; Poljak, Vedran; Mladineo, Ivona

    2015-12-01

    Infective third-stage larvae (L3) of nematode Anisakis spp. have been recognized as one of the major food-borne threats in lightly processed fish products in Europe, particularly in the Mediterranean region. Therefore, the effect of different storage temperatures of fish on larval post-mortem migration from visceral cavity into fillets is an important parameter to take into account when evaluating the risk for consumer safety. The European anchovy (Engraulis encrasicolus) were caught during fishing season, a subsample of fillets was checked for the presence of Anisakis larvae at capture (mean abundance=0.07), and the rest was stored at four different temperatures (-18, 0, 4 and 22°C) in order to count migrating larvae and measure the production of biogenic amines over a period of time. Larvae were identified by morphological features and molecular tools. Post-mortem migration was observed in fillets stored at 0 and 4°C after three and five days, respectively, but not at 22 and -18°C. In case of storage at 22°C for two days, at the onset of putrefaction of the visceral organs, larvae migrated out of the visceral cavity towards the fish surface. Measured pH and biogenic amine profile during storage indicated that certain biochemical conditions trigger larval migration into fillets. Likewise, migration was observed at pH ~6.4 when sensory degradation of the fish was markedly visible. Although larval migration was delayed for approximately four days at a temperature of <4°C the correlation between pH and abundance of A. pegreffii larvae in the fillet was high and statistically significant at both 0 (r=0.998, p<0.01) and 4°C (r=0.946, p<0.05). Out of eight biogenic amines measured, cadaverine and putrescine levels correlated the most with the post-mortem migration at 4°C, while tyramine levels were significant at both temperatures.

  3. Storage of biogenic amines in guinea-pig brain synaptosomes: influence of proton gradient and membrane potential

    PubMed Central

    Affolter, H.; Peyer, M.; Pletscher, A.

    1983-01-01

    1 The effects of K+, NaCN and the ionophores monensin, nonactin and carbonyl-cyanide-p-trifluoro-methoxyphenylhydrazone (FCCP) on the contents of [3H]-5-hydroxytryptamine ([3H]-5-HT), [3H]-dopamine and [3H]-noradrenaline ([3H]-NA) in guinea-pig synaptosomes preloaded with these amines were measured. 2 In the presence of Ca2+, K+ markedly reduced the amine content of the synaptosomes, indicating an acceleration of spontaneous amine release. In the absence of Ca2+, K+ had much less effect. 3 Monensin, nonactin and FCCP caused a release of all the three labelled amines. This release was considerably faster and more marked than that induced by K+ and showed no dependence on Ca2+. The ionophores did not release lactate-dehydrogenase from synaptosomes. 4 NaCN, a blocker of oxidative energy production, did not enhance the spontaneous release of [3H]-5-HT nor did it influence the monensin-induced release of [3H]-5-HT. 5 It is concluded that (a) the intragranular storage of 5-HT, dopamine and NA is dependent on the maintenance of a pH-gradient across the granular membrane as well as on the granular membrane potential; (b) the ionophores cause a non-exocytotic release of granular amines, and (c) blood platelets are partial models for aminergic brain neurones as far as intragranular amine storage is concerned. PMID:6297644

  4. Effects of plant polyphenols and a-tocopherol on lipid oxidation, residual nitrites, biogenic amines, and N-nitrosamines formation during ripening and storage of dry-cured bacon

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Effects of plant polyphenols (green tea polyphenols (GTP) and grape seed extract (GSE) and a-tocopherol on physicochemical parameters, lipid oxidation, residual nitrite, microbiological counts, biogenic amines, and N-nitrosamines were determined in bacons during dry-curing and storage. Results show ...

  5. A Metal and Base-Free Chemoselective Primary Amination of Boronic Acids Using Cyanamidyl/Arylcyanamidyl Radical as Aminating Species: Synthesis and Mechanistic Studies by Density Functional Theory.

    PubMed

    Chatterjee, Nachiketa; Arfeen, Minhajul; Bharatam, Prasad V; Goswami, Avijit

    2016-06-17

    An efficient, metal and base-free, chemoselective synthesis of aryl-, heteroaryl-, and alkyl primary amines from the corresponding boronic acids has been achieved at ambient temperature mediated by [bis(trifluoroacetoxy)iodo]benzene (PIFA) and N-bromosuccinimide (NBS) using cyanamidyl/arylcyanamidyl radicals as the aminating species. The primary amine compounds were initially obtained as their corresponding ammonium trifluoroacetate salts which, on treatment with aq NaOH, provide the free amines. Finally, the primary amines were isolated through column chromatography over silica-gel using hexane-EtOAc solvent system as the eluent. The reactions are sufficiently fast, completing within 1 h. Quantum chemical calculations in combination with experimental observations validate that the ipso amination of substituted boronic acids involves the formation of cyanamidyl/arylcyanamidyl radical, followed by regiospecific interaction of its nitrile-N center with boron atom of the boronic acids, leading to chemoselective primary amination.

  6. 40 CFR 721.1675 - Disulfonic acid rosin amine salt of a benzidine derivative (generic name).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.1675 Disulfonic acid rosin amine salt of a... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Disulfonic acid rosin amine salt of...

  7. 40 CFR 721.1675 - Disulfonic acid rosin amine salt of a benzidine derivative (generic name).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.1675 Disulfonic acid rosin amine salt of a... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Disulfonic acid rosin amine salt of...

  8. 40 CFR 721.1675 - Disulfonic acid rosin amine salt of a benzidine derivative (generic name).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.1675 Disulfonic acid rosin amine salt of a... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Disulfonic acid rosin amine salt of...

  9. 40 CFR 721.1675 - Disulfonic acid rosin amine salt of a benzidine derivative (generic name).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES CONTROL ACT SIGNIFICANT NEW USES OF CHEMICAL SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.1675 Disulfonic acid rosin amine salt of a... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Disulfonic acid rosin amine salt of...

  10. 40 CFR 721.7770 - Alkylphenoxypoly(oxyethylene) sulfuric acid ester, substituted amine salt.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... acid ester, substituted amine salt. 721.7770 Section 721.7770 Protection of Environment ENVIRONMENTAL... ester, substituted amine salt. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified as alkyl phenoxypoly(oxyethylene) sulfuric acid ester,...

  11. Boron-Catalyzed N-Alkylation of Amines using Carboxylic Acids.

    PubMed

    Fu, Ming-Chen; Shang, Rui; Cheng, Wan-Min; Fu, Yao

    2015-07-27

    A boron-based catalyst was found to catalyze the straightforward alkylation of amines with readily available carboxylic acids in the presence of silane as the reducing agent. Various types of primary and secondary amines can be smoothly alkylated with good selectivity and good functional-group compatibility. This metal-free amine alkylation was successfully applied to the synthesis of three commercial medicinal compounds, Butenafine, Cinacalcet. and Piribedil, in a one-pot manner without using any metal catalysts. PMID:26150397

  12. Boron-Catalyzed N-Alkylation of Amines using Carboxylic Acids.

    PubMed

    Fu, Ming-Chen; Shang, Rui; Cheng, Wan-Min; Fu, Yao

    2015-07-27

    A boron-based catalyst was found to catalyze the straightforward alkylation of amines with readily available carboxylic acids in the presence of silane as the reducing agent. Various types of primary and secondary amines can be smoothly alkylated with good selectivity and good functional-group compatibility. This metal-free amine alkylation was successfully applied to the synthesis of three commercial medicinal compounds, Butenafine, Cinacalcet. and Piribedil, in a one-pot manner without using any metal catalysts.

  13. Determination of biogenic amines in wines by ion-pair liquid chromatography and post-column derivatization with 1,2-naphthoquinone-4-sulphonate.

    PubMed

    Hlabangana, Leah; Hernández-Cassou, Santiago; Saurina, Javier

    2006-10-13

    A liquid chromatographic method with post-column derivatization for the determination of biogenic amines in wines is proposed. The method is based on the separation of amines by ion-pair chromatography using sodium heptanesulfonate (SHS) and on-line labeling of analytes with 1,2-naphthoquinone-4-sulfonate. The principal factors influencing the separation (acetonitrile and SHS concentration) have been considered for the optimization of the elution gradient through factorial design and multicriteria decision-making. Figures of merit have been established using red wine samples. Detection limits range from 0.2 to 3 mg L(-1), the peak area run-to-run repeatability from 1.6 to 4.6% and the retention time repeatability lower than 1.2%. Recoveries ranging from 92 and 108% prove the accuracy of the method for determining ethanolamine, ethylamine, histamine and tyramine in commercial red wines. The proposed method has been applied to the analysis of wines from different Spanish regions.

  14. Acid gas absorption in aqueous solutions of mixed amines

    SciTech Connect

    Rinker, E.B.; Ashour, S.S.; Sandall, O.C.

    1996-12-31

    A mass transfer model has been developed to describe the rate of absorption (or desorption) of H{sub 2}S and CO{sub 2} in aqueous blends of a tertiary and a secondary or a primary amine. The model is based on penetration theory, and all significant chemical reactions are incorporated in the model. The reactions are taken to be reversible, with reactions involving only a proton transfer considered to be at equilibrium. The particular amines studied in this research were methyldiethanolamine (MDEA), a tertiary amine, and diethanolamine (DEA), a secondary amine. Key physicochemical data needed in the model, such as diffusion coefficients, kinetic rate constants, and gas solubilities, were measured. Experimental absorption rates of CO{sub 2} and H{sub 2}S were measured in a model gas-liquid contacting device and were compared with model predictions. Experiments were carried out for single amine solutions (both MDEA and DEA) and for amine blends.

  15. Observation of neutral sulfuric acid-amine containing clusters in laboratory and ambient measurements

    SciTech Connect

    Kuang C.; Zhao, J.; Smith, J. N.; Eisele, F. L.; Chen, M.; McMurry, P. H.

    2011-11-02

    Recent ab initio calculations showed that amines can enhance atmospheric sulfuric acid-water nucleation more effectively than ammonia, and this prediction has been substantiated in laboratory measurements. Laboratory studies have also shown that amines can effectively displace ammonia in several types of ammonium clusters. However, the roles of amines in cluster formation and growth at a microscopic molecular scale (from molecular sizes up to 2 nm) have not yet been well understood. Processes that must be understood include the incorporation of amines into sulfuric acid clusters and the formation of organic salts in freshly nucleated particles, which contributes significantly to particle growth rates. We report the first laboratory and ambient measurements of neutral sulfuric acid-amine clusters using the Cluster CIMS, a recently-developed mass spectrometer designed for measuring neutral clusters formed in the atmosphere during nucleation. An experimental technique, which we refer to as Semi-Ambient Signal Amplification (SASA), was employed. Sulfuric acid was added to ambient air, and the concentrations and composition of clusters in this mixture were analyzed by the Cluster CIMS. This experimental approach led to significantly higher cluster concentrations than are normally found in ambient air, thereby increasing signal-to-noise levels and allowing us to study reactions between gas phase species in ambient air and sulfuric acid containing clusters. Mass peaks corresponding to clusters containing four H{sub 2}SO{sub 4} molecules and one amine molecule were clearly observed, with the most abundant sulfuric acid-amine clusters being those containing a C2- or C4-amine (i.e. amines with masses of 45 and 73 amu). Evidence for C3- and C5-amines (i.e. amines with masses of 59 and 87 amu) was also found, but their correlation with sulfuric acid tetramer was not as strong as was observed for the C2- and C4-amines. The formation mechanisms for those sulfuric acid-amine

  16. Boric acid: a highly efficient catalyst for transamidation of carboxamides with amines.

    PubMed

    Nguyen, Thanh Binh; Sorres, Jonathan; Tran, Minh Quan; Ermolenko, Ludmila; Al-Mourabit, Ali

    2012-06-15

    A novel method of transamidation of carboxamides with amines using catalytic amounts of readily available boric acid under solvent-free conditions has been developed. The scope of the methodology has been demonstrated with (i) primary, secondary, and tertiary amides and phthalimide and (ii) aliphatic, aromatic, cyclic, acyclic, primary, and secondary amines.

  17. Polymerized fatty acid amine derivatives useful as friction and wear-reducing additives

    SciTech Connect

    Coupland, K.; Smith, C.R.

    1981-02-10

    A hydrocarbon composition having a major portion of a hydrocarbon preferably a lubricating oil such as mineral oil and at least a friction-reducing amount usually 0.01 to 10 weight percent of an amine or amine derivative of a hydrocarbon-soluble polymerized fatty acid e.g. a dimeramine derived from a dicarboxylic acid containing at least 12 carbon atoms such as 9(10)-carboxy stearic acid has improved antifriction and flue economy properties.

  18. Metal and base free synthesis of primary amines via ipso amination of organoboronic acids mediated by [bis(trifluoroacetoxy)iodo]benzene (PIFA).

    PubMed

    Chatterjee, Nachiketa; Goswami, Avijit

    2015-08-01

    A metal and base free synthesis of primary amines has been developed at ambient temperature through ipso amination of diversely functionalized organoboronic acids, employing a combination of [bis(trifluoroacetoxy)iodo]benzene (PIFA)-N-bromosuccinimide (NBS) and methoxyamine hydrochloride as the aminating reagent. The amines were primarily obtained as their trifluoroacetate salts which on subsequent aqueous alkaline work up provided the corresponding free amines. The combination of PIFA-NBS is found to be the mildest choice compared to the commonly used strong bases (e.g. n-BuLi, Cs2CO3) for activating the aminating agent. The reaction is expected to proceed via activation of the aminating reagent followed by B-N 1,2-aryl migration.

  19. Tandem bis-aza-Michael addition reaction of amines in aqueous medium promoted by polystyrenesulfonic Acid

    EPA Science Inventory

    An efficient and environmentally benign tandem bis-aza-Michael addition of amines catalyzed by polystyrene sulfonic acid (PSSA) is described. This operationally simple high yielding microwave assisted synthetic protocol proceeded in water in the absence of any organic solvent.

  20. Mutagenesis Reveals Structure–Activity Parallels between Human A2A Adenosine Receptors and Biogenic Amine G Protein-Coupled Receptors

    PubMed Central

    Jiang, Qiaoling; Lee, Brian X.; Glashofer, Marc; van Rhee, A. Michiel; Jacobson, Kenneth A.

    2012-01-01

    Structure–affinity relationships for ligand binding at the human A2A adenosine receptor have been probed using site-directed mutagenesis in the transmembrane helical domains (TMs). The mutant receptors were expressed in COS-7 cells and characterized by binding of the radioligands [3H]CGS21680, [3H]NECA, and [3H]XAC. Three residues, at positions essential for ligand binding in other G protein-coupled receptors, were individually mutated. The residue V(3.32) in the A2A receptor that is homologous to the essential aspartate residue of TM3 in the biogenic amine receptors, i.e., V84(3.32), may be substituted with L (present in the A3 receptor) but not with D (in biogenic amine receptors) or A. H250(6.52), homologous to the critical N507 of rat m3 muscarinic acetylcholine receptors, may be substituted with other aromatic residues or with N but not with A (Kim et al. J. Biol. Chem. 1995, 270, 13987–13997). H278(7.43), homologous to the covalent ligand anchor site in rhodopsin, may not be substituted with either A, K, or N. Both V84L(3.32) and H250N(6.52) mutant receptors were highly variable in their effect on ligand competition depending on the structural class of the ligand. Adenosine-5′-uronamide derivatives were more potent at the H250N(6.52) mutant receptor than at wild type receptors. Xanthines tended to be close in potency (H250N(6.52)) or less potent (V84L-(3.32)) than at wild type receptors. The affinity of CGS21680 increased as the pH was lowered to 5.5 in both the wild type and H250N(6.52) mutant receptors. Thus, protonation of H250-(6.52) is not involved in this pH dependence. These data are consistent with a molecular model predicting the proximity of bound agonist ligands to TM3, TM5, TM6, and TM7. PMID:9258366

  1. Changes in Biogenic Amines and ATP-Related Compounds and Their Relation to Other Quality Changes in Common Carp (Cyprinus carpio var. Jian) Stored at 20 and 0°C.

    PubMed

    Zhang, Yuemei; Qin, Na; Luo, Yongkang; Shen, Huixing

    2015-09-01

    Biogenic amines, ATP-related compounds, sensory attributes, total volatile basic nitrogen, microbial flora (total viable bacteria, Pseudomonas, Aeromonas, and H2S-producing bacteria), and free amino acids were determined in common carp (Cyprinus carpio var. Jian) stored at 20 and 0°C. Pseudomonas and H2S-producing bacteria became the dominant bacteria in carp stored at 20 and 0°C, whereas Aeromonas rapidly increased only in carp stored at 0°C. Inosine monophosphate, which is responsible for flavor and freshness, increased to a maximum of 2.37 l mol/g after 12 h at 20°C and to 4.72 l mol/g after 3 days at 0°C. Putrescine and cadaverine were the dominant amines in carp and their concentrations were significantly correlated (P < 0.05) with total volatile basic nitrogen and sensory scores in all samples during the storage. Significant correlations also were observed between histamine and total volatile basic nitrogen and sensory scores only in samples stored at 20°C. Arginine decreased while putrescine increased in all samples. A significant decrease (P < 0.05) in histidine was observed after 24 h of storage, which coincided with an increase in histamine after 36 h in samples stored at 20°C. Hypoxanthine concentrations were significantly correlated with the microbial species (P < 0.01) and sensory scores (P < 0.05) and seems to be a reliable marker for quality of carp fillets stored at 20 and 0°C.

  2. Isomer-sensitive deboronation in reductive aminations of aryl boronic acids

    DOE PAGES

    Jones, Brad Howard; Wheeler, David R.; Wheeler, Jill S.; Miller, Lance Lee; Alam, Todd M.; Spoerke, Erik David

    2015-09-05

    Deboronation is observed during the reductive amination of formylphenylboronic acid (FPBA) to the amine termini and side chains of peptides. This deboronation is sensitive to the isomerism of the boronic acid (BA), with ortho-FPBA yielding complete deboronation in the preparation of an N-terminally-modified dipeptide. The observed behavior is also clearly mediated by the chemical identity of the amine substrate. These results reveal a previously undocumented subtlety of BA functionalization and highlight the importance of thorough spectroscopic characterization in the preparation of peptide and small molecule BAs.

  3. Isomer-sensitive deboronation in reductive aminations of aryl boronic acids

    SciTech Connect

    Jones, Brad Howard; Wheeler, David R.; Wheeler, Jill S.; Miller, Lance Lee; Alam, Todd M.; Spoerke, Erik David

    2015-09-05

    Deboronation is observed during the reductive amination of formylphenylboronic acid (FPBA) to the amine termini and side chains of peptides. This deboronation is sensitive to the isomerism of the boronic acid (BA), with ortho-FPBA yielding complete deboronation in the preparation of an N-terminally-modified dipeptide. The observed behavior is also clearly mediated by the chemical identity of the amine substrate. These results reveal a previously undocumented subtlety of BA functionalization and highlight the importance of thorough spectroscopic characterization in the preparation of peptide and small molecule BAs.

  4. Raman Scattering Sensor for On-Line Monitoring of Amines and Acid Gases

    SciTech Connect

    Uibel, Rory; Smith, Lee

    2010-05-20

    Sulfur and CO2 removal from hydrocarbon streams and power plant effluents are a major problem. The sulfur is normally in the form of H2S. These two acid gases are scrubbed using aqueous amine solutions that are difficult to control with conventional technology. Process Instruments Inc. developed Raman scattering technology for on-line, real-time monitoring of amine streams to improve their efficiency in scrubbing H2S and CO2 from hydrocarbon streams and power plant effluents. Improved control of amine and acid gas concentrations will allow refineries, natural gas processes and power plants to more efficiently scrub Sulfur and CO2, saving energy, time and financial resources.

  5. Formation rates, stability and reactivity of sulfuric acid - amine clusters predicted by computational chemistry

    NASA Astrophysics Data System (ADS)

    Kurtén, Theo; Ortega, Ismael; Kupiainen, Oona; Olenius, Tinja; Loukonen, Ville; Reiman, Heidi; McGrath, Matthew; Vehkamäki, Hanna

    2013-04-01

    Despite the importance of atmospheric particle formation for both climate and air quality, both experiments and non-empirical models using e.g. sulfuric acid, ammonia and water as condensing vapors have so far been unable to reproduce atmospheric observations using realistic trace gas concentrations. Recent experimental and theoretical evidence has shown that this mystery is likely resolved by amines. Combining first-principles evaporation rates for sulfuric acid - dimethylamine clusters with cluster kinetic modeling, we show that even sub-ppt concentrations of amines, together with atmospherically realistic concentrations of sulfuric acid, result in formation rates close to those observed in the atmosphere. Our simulated cluster formation rates are also close to, though somewhat larger than, those measured at the CLOUD experiment in CERN for both sulfuric acid - ammonia and sulfuric acid - dimethylamine systems. A sensitivity analysis indicates that the remaining discrepancy for the sulfuric acid - amine particle formation rates is likely caused by steric hindrances to cluster formation (due to alkyl groups of the amine molecules) rather than by significant errors in the evaporation rates. First-principles molecular dynamic and reaction kinetic modeling shed further light on the microscopic physics and chemistry of sulfuric acid - amine clusters. For example, while the number and type of hydrogen bonds in the clusters typically reach their equilibrium values on a picosecond timescale, and the overall bonding patterns predicted by traditional "static" quantum chemical calculations seem to be stable, the individual atoms participating in the hydrogen bonds continuously change at atmospherically realistic temperatures. From a chemical reactivity perspective, we have also discovered a surprising phenomenon: clustering with sulfuric acid molecules slightly increases the activation energy required for the abstraction of alkyl hydrogens from amine molecules. This implies

  6. Salting-out assisted liquid-liquid extraction for the determination of biogenic amines in fruit juices and alcoholic beverages after derivatization with 1-naphthylisothiocyanate and high performance liquid chromatography.

    PubMed

    Jain, Archana; Gupta, Manju; Verma, Krishna K

    2015-11-27

    A new method for determining biogenic amines in fruit juices and alcoholic beverages is described involving reaction of biogenic amines with 1-naphthylisothiocyanate followed by extraction of 1-naphthylthiourea derivatives with water-miscible organic solvent acetonitrile when solvents phase separation occurred using ammonium sulphate, a process called salting-out assisted liquid-liquid extraction. The extract was analyzed by high-performance liquid chromatography with UV detection at 254nm. The new reagent avoided many of the inconveniences as observed with existing derivatizing agents, such as dansyl chloride and benzoyl chloride, in regard to their inselectivity, instability, adverse effect of excess reagent, and necessity to remove excess reagent. The procedure has been optimized with respect to reaction time and temperature, water-miscible extraction solvent, and salt for solvents phase separation. Use of reagent as dispersed phase in aqueous medium produced derivatives in high yield. A linear calibration was obtained between the amount of biogenic amines in range 1-1000μgL(-1) and peak areas of corresponding thioureas formed; the correlation coefficient was 0.9965, and the limit of detection and limit of quantification found were 1.1μgL(-1) and 3.2μgL(-1), respectively. The pre-concentration method gave an average enrichment factor of 94. The application of the method has been demonstrated in the determination of biogenic amines in commercial samples of fruit juices and alcoholic beverages. In spiking experiments to real samples, the average recovery found by the present method was 94.5% that agreed well with 95.8% obtained by established comparison methods.

  7. Lactic acid bacterial extract as a biogenic mineral growth modifier

    NASA Astrophysics Data System (ADS)

    Borah, Ballav M.; Singh, Atul K.; Ramesh, Aiyagari; Das, Gopal

    2009-04-01

    The formation of minerals and mechanisms by which bacteria could control their formation in natural habitats is now of current interest for material scientists to have an insight of the mechanism of in vivo mineralization, as well as to seek industrial and technological applications. Crystalline uniform structures of calcium and barium minerals formed micron-sized building blocks when synthesized in the presence of an organic matrix consisting of secreted protein extracts from three different lactic acid bacteria (LAB) viz.: Lactobacillus plantarum MTCC 1325, Lactobacillus acidophilus NRRL B4495 and Pediococcus acidilactici CFR K7. LABs are not known to form organic matrix in biological materialization processes. The influence of these bacterial extracts on the crystallization behavior was investigated in details to test the basic coordination behavior of the acidic protein. In this report, varied architecture of the mineral crystals obtained in presence of high molecular weight protein extracts of three different LAB strains has been discussed. The role of native form of high molecular weight bacterial protein extracts in the generation of nucleation centers for crystal growth was clearly established. A model for the formation of organic matrix-cation complex and the subsequent events leading to crystal growth is proposed.

  8. Effects of different freezing treatments on the biogenic amine and quality changes of bighead carp (Aristichthys nobilis) heads during ice storage.

    PubMed

    Hong, Hui; Luo, Yongkang; Zhou, Zhongyun; Bao, Yulong; Lu, Han; Shen, Huixing

    2013-06-01

    The effects of different freezing treatments on the quality changes of bighead carp heads were evaluated in terms of pH value, TBARS, TVB-N, K-value, biogenic amine, total aerobic counts (TACs), drip loss, cooking loss and electrical conductivity (EC) during ice storage. Fish heads were stored at -40°C (T1), -40°C for 12h and then -18°C (T2), -18°C (T3) for 3months prior to ice storage. No significant differences were observed among T1, T2 and T3 for drip loss, cooking loss and EC (p>0.05). T2 showed lower TACs, pH value, TBARS and TVB-N than T3 did. Significant lower value of spermine and spermidine were observed in T1, T2 and T3 than those of control group (fresh) from 9th to 18th day (p<0.05). Drip loss was significantly correlated with TBARS, pH value, TVB-N, and TACs in groups T1, T2 and T3 (p<0.05). PMID:23411270

  9. Effect of Selected Starter Cultures on Physical, Chemical and Microbiological Characteristics and Biogenic Amine Content in Protected Geographical Indication Ciauscolo Salami

    PubMed Central

    Ranucci, David; Loschi, Anna Rita; Miraglia, Dino; Stocchi, Roberta; Rea, Stefano

    2016-01-01

    The aim of the study was to evaluate the biogenic amine (BA) content of Ciauscolo salami made with and without the use of a selected started culture. Two batches of salami were made following the guidelines of the Protected Geographical Indications: with and without adding a commercial starter culture made of Lactobacillus plantarum and Staphylococcus xylosus. Six samples of salami per batch were collected at different ripening times (0, 15, 30, 45 and 60 days) for physical, chemical and microbiological analyses and for the determination of BA content. No differences were recorded for physical, chemical and microbiological analyses except for Staphylococcus spp. count at the time of casing (T0) and total volatile basic nitrogen (TVBN) from 30 days (T2) to the end of the ripening time (60 days, T4). After 60 days of ripening, the use of selected starter culture significantly affected the amount of putrescine (195.15 vs 164.43 mg/100 g in salami without and with starters, respectively), cadaverine (96.95 vs 104.40 mg/100 g in salami without and with starters, respectively), histamine (81.94 vs 69.89 mg/100 g in salami without and with starters, respectively), and spermine (36.88 vs 33.57 mg/100 g in salami without and with starters, respectively). Despite significantly higher values of TVBN, the use of selected starter culture determined no significant effects on the BA content of the products. PMID:27800431

  10. A 4-hydroxy-N'-[(E)-(2-hydroxyphenyl)methylidene]benzohydrazide-based sorbent material for the extraction-HPLC determination of biogenic amines in food samples.

    PubMed

    Tameem, Abdassalam Abdelhafiz; Saad, Bahruddin; Makahleh, Ahmad; Salhin, Abdussalam; Saleh, Muhammad Idiris

    2010-09-15

    A sorbent material based on a newly synthesized hydrazone ligand, 4-hydroxy-N'-[(E)-(2-hydroxyphenyl)methylidene]benzohydrazide was prepared by immobilizing the ligand into a silica sol-gel matrix. The capability of the sorbent material for the extraction of seven biogenic amines (BAs), i.e., tryptamine (TRY), beta-phenylethylamine (PEA), putrescine (PUT), cadaverine (CAD), histamine (HIS), tyramine (TYR), and spermidine (SPD) was studied. Under the adopted conditions, the sorbent showed good selectivity towards PUT, CAD, HIS and SPD (% extraction (%E)>96) while %E for TYR, TRY and PEA were 82.0, 78.9 and 46.4%, respectively. The sorbent could be used up to six extraction cycles for SPD, CAD and PUT and was applied to the determination of food samples ("budu", ketchup, orange juice, soy sauce) that were spiked with 20 mg L(-1) of the BAs. The extracted analytes were derivatized with dansyl chloride before the HPLC determination. With the exception of HIS and TYR in "budu" sample, reasonable recoveries were found for the other analytes in all the tested food samples. PMID:20801345

  11. Effects of different freezing treatments on the biogenic amine and quality changes of bighead carp (Aristichthys nobilis) heads during ice storage.

    PubMed

    Hong, Hui; Luo, Yongkang; Zhou, Zhongyun; Bao, Yulong; Lu, Han; Shen, Huixing

    2013-06-01

    The effects of different freezing treatments on the quality changes of bighead carp heads were evaluated in terms of pH value, TBARS, TVB-N, K-value, biogenic amine, total aerobic counts (TACs), drip loss, cooking loss and electrical conductivity (EC) during ice storage. Fish heads were stored at -40°C (T1), -40°C for 12h and then -18°C (T2), -18°C (T3) for 3months prior to ice storage. No significant differences were observed among T1, T2 and T3 for drip loss, cooking loss and EC (p>0.05). T2 showed lower TACs, pH value, TBARS and TVB-N than T3 did. Significant lower value of spermine and spermidine were observed in T1, T2 and T3 than those of control group (fresh) from 9th to 18th day (p<0.05). Drip loss was significantly correlated with TBARS, pH value, TVB-N, and TACs in groups T1, T2 and T3 (p<0.05).

  12. Photoredox α-Vinylation of α-Amino Acids and N-Aryl Amines

    PubMed Central

    2015-01-01

    A new coupling protocol has been developed that allows the union of vinyl sulfones with photoredox-generated α-amino radicals to provide allylic amines of broad diversity. Direct C–H vinylations of N-aryl tertiary amines, as well as decarboxylative vinylations of N-Boc α-amino acids, proceed in high yield and with excellent olefin geometry control. The utility of this new allyl amine forming reaction has been demonstrated via the syntheses of several natural products and a number of established pharmacophores. PMID:25026314

  13. Flight and walking in locusts-cholinergic co-activation, temporal coupling and its modulation by biogenic amines.

    PubMed

    Rillich, Jan; Stevenson, Paul A; Pflueger, Hans-Joachim

    2013-01-01

    Walking and flying in locusts are exemplary rhythmical behaviors generated by central pattern generators (CPG) that are tuned in intact animals by phasic sensory inputs. Although these two behaviors are mutually exclusive and controlled by independent CPGs, leg movements during flight can be coupled to the flight rhythm. To investigate potential central coupling between the underlying CPGs, we used the muscarinic agonist pilocarpine and the amines octopamine and tyramine to initiate fictive flight and walking in deafferented locust preparations. Our data illustrate that fictive walking is readily evoked by comparatively lower concentrations of pilocarpine, whereas higher concentrations are required to elicit fictive flight. Interestingly, fictive flight did not suppress fictive walking so that the two patterns were produced simultaneously. Frequently, leg motor units were temporally coupled to the flight rhythm, so that each spike in a step cycle volley occurred synchronously with wing motor units firing at flight rhythm frequency. Similarly, tyramine also induced fictive walking and flight, but mostly without any coupling between the two rhythms. Octopamine in contrast readily evoked fictive flight but generally failed to elicit fictive walking. Despite this, numerous leg motor units were recruited, whereby each was temporarily coupled to the flight rhythm. Our results support the notion that the CPGs for walking and flight are largely independent, but that coupling can be entrained by aminergic modulation. We speculate that octopamine biases the whole motor machinery of a locust to flight whereas tyramine primarily promotes walking.

  14. Flight and Walking in Locusts–Cholinergic Co-Activation, Temporal Coupling and Its Modulation by Biogenic Amines

    PubMed Central

    Rillich, Jan; Stevenson, Paul A.; Pflueger, Hans-Joachim

    2013-01-01

    Walking and flying in locusts are exemplary rhythmical behaviors generated by central pattern generators (CPG) that are tuned in intact animals by phasic sensory inputs. Although these two behaviors are mutually exclusive and controlled by independent CPGs, leg movements during flight can be coupled to the flight rhythm. To investigate potential central coupling between the underlying CPGs, we used the muscarinic agonist pilocarpine and the amines octopamine and tyramine to initiate fictive flight and walking in deafferented locust preparations. Our data illustrate that fictive walking is readily evoked by comparatively lower concentrations of pilocarpine, whereas higher concentrations are required to elicit fictive flight. Interestingly, fictive flight did not suppress fictive walking so that the two patterns were produced simultaneously. Frequently, leg motor units were temporally coupled to the flight rhythm, so that each spike in a step cycle volley occurred synchronously with wing motor units firing at flight rhythm frequency. Similarly, tyramine also induced fictive walking and flight, but mostly without any coupling between the two rhythms. Octopamine in contrast readily evoked fictive flight but generally failed to elicit fictive walking. Despite this, numerous leg motor units were recruited, whereby each was temporarily coupled to the flight rhythm. Our results support the notion that the CPGs for walking and flight are largely independent, but that coupling can be entrained by aminergic modulation. We speculate that octopamine biases the whole motor machinery of a locust to flight whereas tyramine primarily promotes walking. PMID:23671643

  15. Rapid simultaneous determination of amines and organic acids in citrus using high-performance liquid chromatography.

    PubMed

    Uckoo, Ram M; Jayaprakasha, Guddadarangavvanahally K; Nelson, Shad D; Patil, Bhimanagouda S

    2011-01-15

    Rapid analytical method for the simultaneous separation and determination of amines and organic acids is a vital interest for quality control of citrus and their products. In the present study, a simultaneous high performance liquid chromatography (HPLC) method for the rapid separation of three amines and two organic acids was developed. Chromatographic separation of compounds was achieved using Xbridge C(18) column at ambient temperature, with an isocratic mobile phase of 3mM phosphoric acid at a flow rate of 1.0 mL min(-1). A photodiode array (PDA) detector was used to monitor the eluent at 223 nm and 254 nm with a total analysis time of 10 min. Extraction of amines and organic acids from citrus juice was optimized. The method was validated by tests of linearity, recovery, precision and ruggedness. The limit of detection (LOD) and limit of quantification (LOQ) for amines and ascorbic acid were determined to be 5 ng and 9.8 ng, respectively. All calibration curves showed good linearity (R(2) ≥ 0.9999) within the test ranges. The recoveries of the amines and organic acids ranged between 84% and 117%. The identity of each peak was confirmed by mass spectral (MS) analysis. The developed method was successfully applied to analyze the content of amines and organic acids in six different species and two varieties of citrus. Results indicate that mandarin and Marrs sweet orange contain high level of amines, while pummelo and Rio Red grapefruit had high content of ascorbic acid (137-251 μg mL(-1)) and citric acid (5-22 mg mL(-1)). Synephrine was the major amine present in Clementine (114 μg mL(-1)) and Marrs sweet orange (85 μg mL(-1)). To the best of our knowledge, this is the first report on simultaneous separation and quantification of amines and organic acids in Marrs sweet orange, Meyer lemon, Nova tangerine, Clementine, Ugli tangelo and Wekiwa tangelo.

  16. Kinetic resolution of acids in acylation reactions in the presence of chiral tertiary amines

    SciTech Connect

    Potapov, V.M.; Dem'yanovich, V.M.; Khlebnikov, V.A.

    1988-07-10

    Asymmetric synthesis has now become an important method for the production of optically active compounds, and its most attractive form is asymmetric catalysis. This work was devoted to an investigation into asymmetric catalysis with chiral tertiary amines in acylation reactions. During the acylation of alcohols and amines by the action of racemic 2-phenylpropionic and 2-methyl-3-phenylpropionic acids in the presence of S-nicotine the initial acids are resolved kinetically. The (R)-2-phenylpropionic acid obtained in this way had an optical purity of 0.5-1.5%.

  17. Microbiological quality and biogenic amines in ready-to-eat grilled chicken fillets under vacuum packing, freezing, and high-dose irradiation.

    PubMed

    Baptista, R F; Lemos, M; Teixeira, C E; Vital, H C; Carneiro, C S; Mársico, E T; Conte Júnior, C A; Mano, S B

    2014-06-01

    The combined effects of cooking, vacuum packing, freezing, and high-dose gamma irradiation in the microbiological conservation and in biogenic amine (BA) contents of ready-to-eat grilled breast chicken fillets are investigated in this work. After seasoning, cooking, and vacuum packing, one-third of the samples were stored at -25°C (T1). The remaining two-thirds were treated with 48 kGy, one-third being stored at -25°C (T2) and the other one-third kept at room temperature (T3). All samples were periodically analyzed to determine growth of heterotrophic aerobic mesophilic bacteria (HAMB) and levels of BA (tyramine, TYM; putrescine, PUT; cadaverine, CAD; spermidine, SPD; histamine, HYM; and spermine, SPM). Variance analysis was performed to determine significant changes in the measured data. Grilling caused HAMB counts in seasoned samples to drop from 5.3 log cfu/g to zero. In addition, no viable HAMB cells were detected in the samples throughout the 12-mo storage time. Regarding the BA analyses, the highest mean levels were measured for SPM and CAD with significantly higher levels (P < 0.05) being determined in nonirradiated samples (T1). Furthermore, significantly lower mean levels for the total content of BA were observed in the irradiated samples. Relative to T1 (7.5 ± 1.5 mg/kg), the figures were 47 ± 23% for T2 and 60 ± 25% for T3, mostly due to loss of CAD by radiolysis. Therefore, it can be concluded that the combination of grilling, vacuum packing, freezing, and high-dose gamma irradiation efficiently eliminated HAMB, while sustaining acceptable levels of BA in ready-to-eat chicken breast fillets throughout the 12 mo of storage at room temperature. PMID:24879707

  18. Impact of Gram-negative bacteria in interaction with a complex microbial consortium on biogenic amine content and sensory characteristics of an uncooked pressed cheese.

    PubMed

    Delbès-Paus, Céline; Pochet, Sylvie; Helinck, Sandra; Veisseire, Philippe; Bord, Cécile; Lebecque, Annick; Coton, Monika; Desmasures, Nathalie; Coton, Emmanuel; Irlinger, Françoise; Montel, Marie-Christine

    2012-05-01

    The impact of Gram-negative bacteria on sensory characteristics and production of volatile compounds as well as biogenic amines (BA) in the core of an uncooked pressed type model cheese was investigated in the presence of a defined complex microbial consortium. Eleven strains of Gram-negative bacteria, selected on the basis of their biodiversity and in vitro BA-production ability, were individually tested in a model cheese. Four out of 6 strains of Enterobacteriaceae (Citrobacter freundii UCMA 4217, Klebsiella oxytoca 927, Hafnia alvei B16 and Proteus vulgaris UCMA 3780) reached counts close to 6 log CFU g⁻¹ in the model cheese. In core of cheeses inoculated with Gram-negative bacteria, only slight differences were observed for microbial counts (Enterococcus faecalis or Lactobacillus plantarum count differences below 1 log CFU g⁻¹), acetate concentration (differences below 200 mg kg⁻¹) and texture (greater firmness) in comparison to control cheeses. Cheese core colour, odour and volatile compound composition were not modified. Although ornithine, the precursor of putrescine, was present in all cheeses, putrescine was only detected in cheeses inoculated with H. alvei B16 and never exceeded 2.18 mmol kg⁻¹ cheese dry matter. Cadaverine was only detected in cheeses inoculated with H. alvei B16, K. oxytoca 927, Halomonas venusta 4C1A or Morganella morganii 3A2A but at lower concentrations (<1.05 mmol kg⁻¹ cheese dry matter), although lysine was available. Only insignificant amounts of the detrimental BA histamine and tyramine, as well as isopentylamine, tryptamine or phenylethylamine, were produced in the cheese model by any of the Gram-negative strains, including those which produced these BA at high levels in vitro. PMID:22265286

  19. Microbiological quality and biogenic amines in ready-to-eat grilled chicken fillets under vacuum packing, freezing, and high-dose irradiation.

    PubMed

    Baptista, R F; Lemos, M; Teixeira, C E; Vital, H C; Carneiro, C S; Mársico, E T; Conte Júnior, C A; Mano, S B

    2014-06-01

    The combined effects of cooking, vacuum packing, freezing, and high-dose gamma irradiation in the microbiological conservation and in biogenic amine (BA) contents of ready-to-eat grilled breast chicken fillets are investigated in this work. After seasoning, cooking, and vacuum packing, one-third of the samples were stored at -25°C (T1). The remaining two-thirds were treated with 48 kGy, one-third being stored at -25°C (T2) and the other one-third kept at room temperature (T3). All samples were periodically analyzed to determine growth of heterotrophic aerobic mesophilic bacteria (HAMB) and levels of BA (tyramine, TYM; putrescine, PUT; cadaverine, CAD; spermidine, SPD; histamine, HYM; and spermine, SPM). Variance analysis was performed to determine significant changes in the measured data. Grilling caused HAMB counts in seasoned samples to drop from 5.3 log cfu/g to zero. In addition, no viable HAMB cells were detected in the samples throughout the 12-mo storage time. Regarding the BA analyses, the highest mean levels were measured for SPM and CAD with significantly higher levels (P < 0.05) being determined in nonirradiated samples (T1). Furthermore, significantly lower mean levels for the total content of BA were observed in the irradiated samples. Relative to T1 (7.5 ± 1.5 mg/kg), the figures were 47 ± 23% for T2 and 60 ± 25% for T3, mostly due to loss of CAD by radiolysis. Therefore, it can be concluded that the combination of grilling, vacuum packing, freezing, and high-dose gamma irradiation efficiently eliminated HAMB, while sustaining acceptable levels of BA in ready-to-eat chicken breast fillets throughout the 12 mo of storage at room temperature.

  20. Reductive Amination/Cyclization of Keto Acids Using a Hydrosilane for Selective Production of Lactams versus Cyclic Amines by Switching of the Indium Catalyst.

    PubMed

    Ogiwara, Yohei; Uchiyama, Takuya; Sakai, Norio

    2016-01-26

    Described herein is that the catalytic construction of N-substituted five- and six-membered lactams from keto acids with primary amines by reductive amination, using an indium/silane combination. This relatively benign and safe catalyst/reductant system tolerates the use of a variety of functional groups, especially ones that are reduction-sensitive. A direct switch from synthesizing lactams to synthesizing cyclic amines is achieved by changing the catalyst from In(OAc)3 to InI3. This conversion occurs by further reduction of the lactam using the indium/silane pair.

  1. Antioxidants, Enzyme Inhibitors, and Biogenic Compounds in Grain Extracts of Barleys.

    PubMed

    Maliar, Tibor; Slaba, Gabriela; Nemeček, Peter; Maliarová, Mária; Benková, Michaela; Havrlentová, Michaela; Ondrejovič, Miroslav; Kraic, Ján

    2015-11-01

    The content of biogenic compounds and the biological activities of barley (Hordeum vulgare L.)-grain extracts was evaluated. The sufficiently large and heterogeneous set of barley genotypes (100 accessions) enabled the selection of special genotypes interesting for potential industrial, pharmaceutical, and medicinal applications. Barley genotypes with the highest contents of phenols, phenolic acids, flavonoids, biogenic thiols, and amines, radical-scavenging activity, as well as inhibitory activities of trypsin, thrombin, collagenase, urokinase, and cyclooxygenase were identified.

  2. Antioxidants, Enzyme Inhibitors, and Biogenic Compounds in Grain Extracts of Barleys.

    PubMed

    Maliar, Tibor; Slaba, Gabriela; Nemeček, Peter; Maliarová, Mária; Benková, Michaela; Havrlentová, Michaela; Ondrejovič, Miroslav; Kraic, Ján

    2015-11-01

    The content of biogenic compounds and the biological activities of barley (Hordeum vulgare L.)-grain extracts was evaluated. The sufficiently large and heterogeneous set of barley genotypes (100 accessions) enabled the selection of special genotypes interesting for potential industrial, pharmaceutical, and medicinal applications. Barley genotypes with the highest contents of phenols, phenolic acids, flavonoids, biogenic thiols, and amines, radical-scavenging activity, as well as inhibitory activities of trypsin, thrombin, collagenase, urokinase, and cyclooxygenase were identified. PMID:26567946

  3. Modeling the degradation of Portland cement pastes by biogenic organic acids

    SciTech Connect

    De Windt, Laurent; Devillers, Philippe

    2010-08-15

    Reactive transport models can be used to assess the long-term performance of cement-based materials subjected to biodegradation. A bioleaching test (with Aspergillus niger fungi) applied to ordinary Portland cement pastes during 15 months is modeled with HYTEC. Modeling indicates that the biogenic organic acids (acetic, butyric, lactic and oxalic) strongly accelerate hydrate dissolution by acidic hydrolysis whilst their complexation of aluminum has an effect on the secondary gel stability only. The deepest degradation front corresponds to portlandite dissolution and decalcification of calcium silicate hydrates. A complex pattern of sulfate phases dissolution and precipitation takes place in an intermediate zone. The outermost degraded zone consists of alumina and silica gels. The modeling accurateness of calcium leaching, pH evolution and degradation thickness is consistently enhanced whilst considering increase of diffusivity in the degraded zones. Precipitation of calcium oxalate is predicted by modeling but was hindered in the bioleaching reactor.

  4. 40 CFR 721.9220 - Reaction products of secondary alkyl amines with a substituted benzenesulfonic acid and sulfuric...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Reaction products of secondary alkyl... Reaction products of secondary alkyl amines with a substituted benzenesulfonic acid and sulfuric acid... substances identified generically as reaction products of secondary alkyl amines with a...

  5. 40 CFR 721.9220 - Reaction products of secondary alkyl amines with a substituted benzenesulfonic acid and sulfuric...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Reaction products of secondary alkyl... Reaction products of secondary alkyl amines with a substituted benzenesulfonic acid and sulfuric acid... substances identified generically as reaction products of secondary alkyl amines with a...

  6. 40 CFR 721.9220 - Reaction products of secondary alkyl amines with a substituted benzenesulfonic acid and sulfuric...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Reaction products of secondary alkyl... Reaction products of secondary alkyl amines with a substituted benzenesulfonic acid and sulfuric acid... substances identified generically as reaction products of secondary alkyl amines with a...

  7. 40 CFR 721.9220 - Reaction products of secondary alkyl amines with a substituted benzenesulfonic acid and sulfuric...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Reaction products of secondary alkyl... Reaction products of secondary alkyl amines with a substituted benzenesulfonic acid and sulfuric acid... substances identified generically as reaction products of secondary alkyl amines with a...

  8. 40 CFR 721.9220 - Reaction products of secondary alkyl amines with a substituted benzenesulfonic acid and sulfuric...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Reaction products of secondary alkyl... Reaction products of secondary alkyl amines with a substituted benzenesulfonic acid and sulfuric acid... substances identified generically as reaction products of secondary alkyl amines with a...

  9. Chemical force titrations of amine- and sulfonic acid-modified poly(dimethylsiloxane).

    PubMed

    Wang, Bin; Oleschuk, Richard D; Horton, J Hugh

    2005-02-15

    Chemical force titrations-measurements of the adhesive interaction between a pair of suitably chemically modified atomic force microscopy (AFM) tip and sample surfaces as a function of pH-have been carried out for various combinations of silanol, amine, carboxylic acid, and sulfonic acid functional groups on both tip and sample. The primary surface material studied was poly(dimethylsiloxane) (PDMS). Surface modification was carried out using a plasma oxidation process to form silanol sites; further modification with amine or sulfonic acid sites was carried out by reaction of the silanol sites with the appropriate trialkoxysilane derivative. AFM tips were also modified using trialkoxysilane compounds. In the cases of tip/sample combinations with the same functional group on each, surface pK(1/2) values could be determined. In several "mixed" tip/sample combinations, a peak appeared in the titration curve midway between the surface pK(1/2) values of the tip and sample, consistent with an ionic H-bonding model for the interactions. The amine/sulfonic acid pair showed more complex behavior; the amine-terminated tip/sulfonic acid-terminated PDMS surface force titration curve consisted of two peaks centered at pH 4 and pH 8. Reversing the tip/sample pair resulted in the peak positions being shifted upward by 1.0 pH unit. The peak appearing at lower pH is assigned to electrostatic interactions between the two oppositely charged surfaces, whereas the higher pH peak is believed to arise due to ionic H-bonding interactions. AFM images show the effects on surface patterning of amine- and sulfonic acid-modified PDMS surfaces that have undergone two different oxidation methods (air plasma oxidation and Tesla coil oxidation). The surface morphologies of freshly prepared and 24 h aged air plasma oxidized PDMS are also discussed in this study.

  10. Plant and Soil Emissions of Amines and Amino Acids: A Source of Secondary Aerosol Precursors

    NASA Astrophysics Data System (ADS)

    Jackson, M. L.; Doskey, P. V.; Pypker, T. G.

    2011-12-01

    Ammonia (NH3) is the most abundant alkaline gas in the atmosphere and forms secondary aerosol by neutralizing sulfuric and nitric acids that are released during combustion of fossil fuels. Ammonia is primarily emitted by cropping and livestock operations. However, C2 and C3 amines (pKb 3.3-3.4), which are stronger bases than NH3 (pKb 4.7) have been observed in nuclei mode aerosol that is the precursor to secondary aerosol. Mixtures of amines and amino acids have been identified in diverse environments in aerosol, fog water, cloud water, the soluble fraction of precipitation, and in dew. Glycine (pKb 4.2), serine (pKb 4.8) and alanine (pKb 3.7 and 4.1 for the D and L forms, respectively) are typically the most abundant species. The only reported values of gas-phase glycine, serine and alanine were in marine air and ranged from 6-14 pptv. The origin of atmospheric amines and amino acids has not been fully identified, although sources are likely similar to NH3. Nitrate assimilation in plants forms glycine, serine, and L-alanine, while D-alanine is present in bacterial cell walls. Glycine is converted to serine during C3 plant photorespiration, producing CO2 and NH3. Bacteria metabolize glycine and alanine to methylamine and ethylamine via decarboxylation. Likely sources of amino acids are plants and bacteria, thus concentrations near continental sources are likely greater than those measured in marine air. The overall goal of the research is to examine seasonal variations and relationships between the exchange of CO2, NH3, amines, and amino acids with a corn/soybean rotation in the Midwest Corn Belt. The study presents gaseous profiles of organic amine compounds from various species of vegetation using a mist chamber trapping technique and analysis of the derivatized species by high pressure liquid chromatography with fluorescence detection. Amino acid and amine profiles were obtained for red oak (Quercus rubra), sugar maple (Acer saccharinum), white pine (Pinus

  11. Amine-based systems for carboxylic acid recovery

    SciTech Connect

    King, C.J.

    1992-05-01

    Several carboxylic acids are prominent commercial products, and their number and importance will probably grow. Getting these acids out of aqueous solution is necessary in petrochemical manufacture, fermentation, and the environmentally and economically important recovery from waste streams. In this paper, the authors discuss the methods possible to extract acids such as citric, lactic, and succinic from complex mixtures. Carboxylic acids are also readily made by fermentation and are among the most attractive substances that could be manufactured from biomass. Branches of this cycle lead to acetic, lactic, propionic, and formic acids, among others. Carboxylic acids are promising intermediates in a bioprocessing complex, because the oxygen of the biomass is placed in a form that is useful for further reaction with many other products. Citric acid is manufactured on a large scale by fermentation, and lactic and fumaric acids, among others, were manufactured that way in the past.

  12. Suppressed blinking behavior of thioglycolic acid capped CdTe quantum dot by amine functionalization

    NASA Astrophysics Data System (ADS)

    Mandal, Abhijit; Tamai, Naoto

    2011-12-01

    Prepared water soluble thioglycolic acid capped CdTe quantum dots (QDs) were further surface functionalized by ethylene diamine (EDA). Amine functionalized CdTe QDs demonstrate enhanced luminescence intensity at ensemble measurements and suppressed luminescence intermittency behavior at the single molecule level. A clear decrease in the power law exponent for "on" time behavior is observed in amine modified CdTe QDs. Our results show that surface of CdTe QDs modified by EDA can lead to an important physical mechanism to enhance fluorescence intensity, reduce blinking, and increase photostability.

  13. Qualitative identification of carboxylic acids, boronic acids, and amines using cruciform fluorophores.

    PubMed

    Schwaebel, Thimon; Lirag, Rio Carlo; Davey, Evan A; Lim, Jaebum; Bunz, Uwe H F; Miljanić, Ognjen Š

    2013-01-01

    Molecular cruciforms are X-shaped systems in which two conjugation axes intersect at a central core. If one axis of these molecules is substituted with electron-donors, and the other with electron-acceptors, cruciforms' HOMO will localize along the electron-rich and LUMO along the electron-poor axis. This spatial isolation of cruciforms' frontier molecular orbitals (FMOs) is essential to their use as sensors, since analyte binding to the cruciform invariably changes its HOMO-LUMO gap and the associated optical properties. Using this principle, Bunz and Miljanić groups developed 1,4-distyryl-2,5-bis(arylethynyl)benzene and benzobisoxazole cruciforms, respectively, which act as fluorescent sensors for metal ions, carboxylic acids, boronic acids, phenols, amines, and anions. The emission colors observed when these cruciform are mixed with analytes are highly sensitive to the details of analyte's structure and - because of cruciforms' charge-separated excited states - to the solvent in which emission is observed. Structurally closely related species can be qualitatively distinguished within several analyte classes: (a) carboxylic acids; (b) boronic acids, and (c) metals. Using a hybrid sensing system composed from benzobisoxazole cruciforms and boronic acid additives, we were also able to discern among structurally similar: (d) small organic and inorganic anions, (e) amines, and (f) phenols. The method used for this qualitative distinction is exceedingly simple. Dilute solutions (typically 10(-6) M) of cruciforms in several off-the-shelf solvents are placed in UV/Vis vials. Then, analytes of interest are added, either directly as solids or in concentrated solution. Fluorescence changes occur virtually instantaneously and can be recorded through standard digital photography using a semi-professional digital camera in a dark room. With minimal graphic manipulation, representative cut-outs of emission color photographs can be arranged into panels which permit quick naked

  14. Qualitative identification of carboxylic acids, boronic acids, and amines using cruciform fluorophores.

    PubMed

    Schwaebel, Thimon; Lirag, Rio Carlo; Davey, Evan A; Lim, Jaebum; Bunz, Uwe H F; Miljanić, Ognjen Š

    2013-08-19

    Molecular cruciforms are X-shaped systems in which two conjugation axes intersect at a central core. If one axis of these molecules is substituted with electron-donors, and the other with electron-acceptors, cruciforms' HOMO will localize along the electron-rich and LUMO along the electron-poor axis. This spatial isolation of cruciforms' frontier molecular orbitals (FMOs) is essential to their use as sensors, since analyte binding to the cruciform invariably changes its HOMO-LUMO gap and the associated optical properties. Using this principle, Bunz and Miljanić groups developed 1,4-distyryl-2,5-bis(arylethynyl)benzene and benzobisoxazole cruciforms, respectively, which act as fluorescent sensors for metal ions, carboxylic acids, boronic acids, phenols, amines, and anions. The emission colors observed when these cruciform are mixed with analytes are highly sensitive to the details of analyte's structure and - because of cruciforms' charge-separated excited states - to the solvent in which emission is observed. Structurally closely related species can be qualitatively distinguished within several analyte classes: (a) carboxylic acids; (b) boronic acids, and (c) metals. Using a hybrid sensing system composed from benzobisoxazole cruciforms and boronic acid additives, we were also able to discern among structurally similar: (d) small organic and inorganic anions, (e) amines, and (f) phenols. The method used for this qualitative distinction is exceedingly simple. Dilute solutions (typically 10(-6) M) of cruciforms in several off-the-shelf solvents are placed in UV/Vis vials. Then, analytes of interest are added, either directly as solids or in concentrated solution. Fluorescence changes occur virtually instantaneously and can be recorded through standard digital photography using a semi-professional digital camera in a dark room. With minimal graphic manipulation, representative cut-outs of emission color photographs can be arranged into panels which permit quick naked

  15. A theoretical study of hydrated molecular clusters of amines and dicarboxylic acids

    NASA Astrophysics Data System (ADS)

    Xu, Wen; Zhang, Renyi

    2013-08-01

    Amines and carboxylic acids have been recognized as important precursor species in atmospheric new particle formation. In this study, the interaction between dimethylamine and succinic acid is investigated using Basin Paving Monte Carlo (BPMC) sampling with the classical force field to obtain low energy conformers of dimethylamine and succinic acid hydrated molecular clusters. Geometry optimization and frequency calculations are further performed on the basis of the BPMC results using density functional theory. At standard temperature and pressure, dimethylamine binds to succinic acid with a bonding energy of 14.2 kcal mol-1, smaller than that of dimethylamine with sulfuric acid (21.1 kcal mol-1). Hydration promotes proton transfer from succinic acid to dimethylamine and consequently increases the interaction strength, while proton transfer from sulfuric acid to dimethylamine occurs without hydration. On the other hand, the reactivity of sulfuric acid with dimethylamine decreases with the degree of hydration of sulfuric acid. The free energies of formation for hydrated clusters consisting of dimethylamine and succinic acid reveal that the interaction between amines and dicarboxylic acids likely exerts a synergetic effect on atmospheric aerosol nucleation by formation of aminium carboxylate ion pairs.

  16. Amine Chemistry at Aqueous Interfaces: The Study of Organic Amines in Neutralizing Acidic Gases at an Air/Water Surface Using Vibrational Sum Frequency Spectroscopy

    NASA Astrophysics Data System (ADS)

    McWilliams, L.; Wren, S. N.; Valley, N. A.; Richmond, G.

    2014-12-01

    Small organic bases have been measured in atmospheric samples, with their sources ranging from industrial processing to animal husbandry. These small organic amines are often highly soluble, being found in atmospheric condensed phases such as fogwater and rainwater. Additionally, they display acid-neutralization ability often greater than ammonia, yet little is known regarding their kinetic and thermodynamic properties. This presentation will describe the molecular level details of a model amine system at the vapor/liquid interface in the presence of acidic gas. We find that this amine system shows very unique properties in terms of its bonding, structure, and orientation at aqueous surfaces. The results of our studies using a combination of computation, vibrational sum frequency spectroscopy, and surface tension will report the properties inherent to these atmospherically relevant species at aqueous surfaces.

  17. Mechanism of Boron-Catalyzed N-Alkylation of Amines with Carboxylic Acids.

    PubMed

    Zhang, Qi; Fu, Ming-Chen; Yu, Hai-Zhu; Fu, Yao

    2016-08-01

    Mechanistic study has been carried out on the B(C6F5)3-catalyzed amine alkylation with carboxylic acid. The reaction includes acid-amine condensation and amide reduction steps. In condensation step, the catalyst-free mechanism is found to be more favorable than the B(C6F5)3-catalyzed mechanism, because the automatic formation of the stable B(C6F5)3-amine complex deactivates the catalyst in the latter case. Meanwhile, the catalyst-free condensation is constituted by nucleophilic attack and the indirect H2O-elimination (with acid acting as proton shuttle) steps. After that, the amide reduction undergoes a Lewis acid (B(C6F5)3)-catalyzed mechanism rather than a Brønsted acid (B(C6F5)3-coordinated HCOOH)-catalyzed one. The B(C6F5)3)-catalyzed reduction includes twice silyl-hydride transfer steps, while the first silyl transfer is the rate-determining step of the overall alkylation catalytic cycle. The above condensation-reduction mechanism is supported by control experiments (on both temperature and substrates). Meanwhile, the predicted chemoselectivity is consistent with the predominant formation of the alkylation product (over disilyl acetal product). PMID:27441997

  18. AN EFFICIENT AND CHEMOSELECTIVE CBZ-PROTECTION OF AMINES USING SILICA-SULFURIC ACID AT ROOM TEMPERATURE

    EPA Science Inventory

    A simple, facile, and chemoselective N-benzyloxycarbonylation of amines using silica-sulfuric acid that proceeds under solvent-free conditions at room temperature has been achieved. These reactions are applicable to a wide variety of primary (aliphatic, cyclic) secondary amines, ...

  19. Molecular understanding of sulphuric acid-amine particle nucleation in the atmosphere.

    PubMed

    Almeida, João; Schobesberger, Siegfried; Kürten, Andreas; Ortega, Ismael K; Kupiainen-Määttä, Oona; Praplan, Arnaud P; Adamov, Alexey; Amorim, Antonio; Bianchi, Federico; Breitenlechner, Martin; David, André; Dommen, Josef; Donahue, Neil M; Downard, Andrew; Dunne, Eimear; Duplissy, Jonathan; Ehrhart, Sebastian; Flagan, Richard C; Franchin, Alessandro; Guida, Roberto; Hakala, Jani; Hansel, Armin; Heinritzi, Martin; Henschel, Henning; Jokinen, Tuija; Junninen, Heikki; Kajos, Maija; Kangasluoma, Juha; Keskinen, Helmi; Kupc, Agnieszka; Kurtén, Theo; Kvashin, Alexander N; Laaksonen, Ari; Lehtipalo, Katrianne; Leiminger, Markus; Leppä, Johannes; Loukonen, Ville; Makhmutov, Vladimir; Mathot, Serge; McGrath, Matthew J; Nieminen, Tuomo; Olenius, Tinja; Onnela, Antti; Petäjä, Tuukka; Riccobono, Francesco; Riipinen, Ilona; Rissanen, Matti; Rondo, Linda; Ruuskanen, Taina; Santos, Filipe D; Sarnela, Nina; Schallhart, Simon; Schnitzhofer, Ralf; Seinfeld, John H; Simon, Mario; Sipilä, Mikko; Stozhkov, Yuri; Stratmann, Frank; Tomé, Antonio; Tröstl, Jasmin; Tsagkogeorgas, Georgios; Vaattovaara, Petri; Viisanen, Yrjo; Virtanen, Annele; Vrtala, Aron; Wagner, Paul E; Weingartner, Ernest; Wex, Heike; Williamson, Christina; Wimmer, Daniela; Ye, Penglin; Yli-Juuti, Taina; Carslaw, Kenneth S; Kulmala, Markku; Curtius, Joachim; Baltensperger, Urs; Worsnop, Douglas R; Vehkamäki, Hanna; Kirkby, Jasper

    2013-10-17

    Nucleation of aerosol particles from trace atmospheric vapours is thought to provide up to half of global cloud condensation nuclei. Aerosols can cause a net cooling of climate by scattering sunlight and by leading to smaller but more numerous cloud droplets, which makes clouds brighter and extends their lifetimes. Atmospheric aerosols derived from human activities are thought to have compensated for a large fraction of the warming caused by greenhouse gases. However, despite its importance for climate, atmospheric nucleation is poorly understood. Recently, it has been shown that sulphuric acid and ammonia cannot explain particle formation rates observed in the lower atmosphere. It is thought that amines may enhance nucleation, but until now there has been no direct evidence for amine ternary nucleation under atmospheric conditions. Here we use the CLOUD (Cosmics Leaving OUtdoor Droplets) chamber at CERN and find that dimethylamine above three parts per trillion by volume can enhance particle formation rates more than 1,000-fold compared with ammonia, sufficient to account for the particle formation rates observed in the atmosphere. Molecular analysis of the clusters reveals that the faster nucleation is explained by a base-stabilization mechanism involving acid-amine pairs, which strongly decrease evaporation. The ion-induced contribution is generally small, reflecting the high stability of sulphuric acid-dimethylamine clusters and indicating that galactic cosmic rays exert only a small influence on their formation, except at low overall formation rates. Our experimental measurements are well reproduced by a dynamical model based on quantum chemical calculations of binding energies of molecular clusters, without any fitted parameters. These results show that, in regions of the atmosphere near amine sources, both amines and sulphur dioxide should be considered when assessing the impact of anthropogenic activities on particle formation. PMID:24097350

  20. Molecular understanding of sulphuric acid-amine particle nucleation in the atmosphere.

    PubMed

    Almeida, João; Schobesberger, Siegfried; Kürten, Andreas; Ortega, Ismael K; Kupiainen-Määttä, Oona; Praplan, Arnaud P; Adamov, Alexey; Amorim, Antonio; Bianchi, Federico; Breitenlechner, Martin; David, André; Dommen, Josef; Donahue, Neil M; Downard, Andrew; Dunne, Eimear; Duplissy, Jonathan; Ehrhart, Sebastian; Flagan, Richard C; Franchin, Alessandro; Guida, Roberto; Hakala, Jani; Hansel, Armin; Heinritzi, Martin; Henschel, Henning; Jokinen, Tuija; Junninen, Heikki; Kajos, Maija; Kangasluoma, Juha; Keskinen, Helmi; Kupc, Agnieszka; Kurtén, Theo; Kvashin, Alexander N; Laaksonen, Ari; Lehtipalo, Katrianne; Leiminger, Markus; Leppä, Johannes; Loukonen, Ville; Makhmutov, Vladimir; Mathot, Serge; McGrath, Matthew J; Nieminen, Tuomo; Olenius, Tinja; Onnela, Antti; Petäjä, Tuukka; Riccobono, Francesco; Riipinen, Ilona; Rissanen, Matti; Rondo, Linda; Ruuskanen, Taina; Santos, Filipe D; Sarnela, Nina; Schallhart, Simon; Schnitzhofer, Ralf; Seinfeld, John H; Simon, Mario; Sipilä, Mikko; Stozhkov, Yuri; Stratmann, Frank; Tomé, Antonio; Tröstl, Jasmin; Tsagkogeorgas, Georgios; Vaattovaara, Petri; Viisanen, Yrjo; Virtanen, Annele; Vrtala, Aron; Wagner, Paul E; Weingartner, Ernest; Wex, Heike; Williamson, Christina; Wimmer, Daniela; Ye, Penglin; Yli-Juuti, Taina; Carslaw, Kenneth S; Kulmala, Markku; Curtius, Joachim; Baltensperger, Urs; Worsnop, Douglas R; Vehkamäki, Hanna; Kirkby, Jasper

    2013-10-17

    Nucleation of aerosol particles from trace atmospheric vapours is thought to provide up to half of global cloud condensation nuclei. Aerosols can cause a net cooling of climate by scattering sunlight and by leading to smaller but more numerous cloud droplets, which makes clouds brighter and extends their lifetimes. Atmospheric aerosols derived from human activities are thought to have compensated for a large fraction of the warming caused by greenhouse gases. However, despite its importance for climate, atmospheric nucleation is poorly understood. Recently, it has been shown that sulphuric acid and ammonia cannot explain particle formation rates observed in the lower atmosphere. It is thought that amines may enhance nucleation, but until now there has been no direct evidence for amine ternary nucleation under atmospheric conditions. Here we use the CLOUD (Cosmics Leaving OUtdoor Droplets) chamber at CERN and find that dimethylamine above three parts per trillion by volume can enhance particle formation rates more than 1,000-fold compared with ammonia, sufficient to account for the particle formation rates observed in the atmosphere. Molecular analysis of the clusters reveals that the faster nucleation is explained by a base-stabilization mechanism involving acid-amine pairs, which strongly decrease evaporation. The ion-induced contribution is generally small, reflecting the high stability of sulphuric acid-dimethylamine clusters and indicating that galactic cosmic rays exert only a small influence on their formation, except at low overall formation rates. Our experimental measurements are well reproduced by a dynamical model based on quantum chemical calculations of binding energies of molecular clusters, without any fitted parameters. These results show that, in regions of the atmosphere near amine sources, both amines and sulphur dioxide should be considered when assessing the impact of anthropogenic activities on particle formation.

  1. Studies of the biogenic amine transporters. VI. Characterization of a novel cocaine binding site, identified with [125I]RTI-55, in membranes prepared from whole rat brain minus caudate.

    PubMed

    Rothman, R B; Silverthorn, M L; Baumann, M H; Goodman, C B; Cadet, J L; Matecka, D; Rice, K C; Carroll, F I; Wang, J B; Uhl, G R

    1995-07-01

    Previous studies showed that the cocaine analog [125I]RTI-55 labels dopamine and serotonergic (5-HT) biogenic amine transporters (BATs) with high affinity. Here we characterized [125I]RTI-55 binding to membranes prepared from whole rat brain minus the caudate nuclei. Paroxetine (50 nM) was used to block [125I]RTI-55 binding to 5-HT transporter sites. Initial experiments identified drugs that displaced [125I]RTI-55 binding with moderately low slope factors. Binding surface analysis of the interaction of 3 beta-(4-chlorophenyl)tropan-2 beta-carboxylic acid phenyl ester hydrochloride (RTI-113) and 3 beta-(4-iodophenyl)tropan-2 beta-carboxylic acid phenyl ester hydrochloride (RTI-122) with [125I]RTI-55 binding sites readily resolved two binding sites for [125I]RTI-55 with Kd values of 0.44 nM and 17 nM and Bmax values of 31 and 245 fmol/mg protein. Potent 5-HT and noradrenergic uptake inhibitors had low affinity for both sites. Whereas cocaine, CFT and WIN35,065-2 were 6.0-, 25- and 14-fold selective for the first site, benztropine, PCP and the novel pyrrole, (+-)-(2RS,3aSR,8bRS)-1,2,3,3a,4,8b-hexahydro- 2-benzyl-1-methylindeno-[1,2-b]pyrrole resorcylate [(+-)-HBMP, formerly called (+-)-RTI-4793-14], were moderately selective for the second site. A single binding site with the characteristics of site 1 was resolved using COS cells transiently expressing the cloned rat dopamine transporter. Lesion studies with 6-hydroxydopamine and 5,7-dihydroxytryptamine were conducted to test the hypothesis that site 1 and site 2 are physically distinct. The data showed that these neurotoxins differentially decreased [125I]RTI-55 binding to sites 1 and 2. The differential distribution of sites 1 and 2 in rat brain provides further support for this hypothesis. Viewed collectively, these data show that [125I]RTI-55 labels a novel binding site in rat brain membranes, termed DATsite2, which is not associated with the classic dopamine, serotonin or norepinephrine transporters.

  2. Application of Granulated Blast Furnace Slag in Cement Composites Exposed to Biogenic Acid Attack

    NASA Astrophysics Data System (ADS)

    Kovalcikova, M.; Estokova, A.; Luptakova, A.

    2015-11-01

    The deterioration of cement-based materials used for the civil infrastructure has led to the realization that cement-based materials, such as concrete, must be improved in terms of their properties and durability. Leaching of calcium ions increases the porosity of cement- based materials, consequently resulting in a negative effect on durability since it provides an entry for aggressive harmful ions, causing corrosion of concrete. The use supplementary cementing composite materials have been reported to improve the resistance of concrete to deterioration by aggressive chemicals. The paper is focused on the investigation of the influence of biogenic acid attack on the cement composites affected by bacteria Acidithiobacillus thiooxidans. The concrete specimens with 65 wt. % addition of antimicrobial activated granulated blast furnace slag as durability increasing factor as well as without any addition were studied. The experiments proceeded during 150 days under model laboratory conditions. The pH values and chemical composition of leachates were measured after each 30- day cycle. The calcium and silicon contents in leachates were evaluated using X - ray fluorescence method (XRF). Summarizing the results, the 65% wt. addition of antimicrobial activated granulated blast furnace slag was not confirmed to be more resistant.

  3. Biogenic catalysis in sulphide minerals' weathering processes and acid mine drainage genesis.

    PubMed

    Kušnierová, Mária; Praščáková, Mária; Nowak, Anna K; Gorazda, Katarzyna; Wzorek, Zbigniew

    2014-01-01

    Bioleaching and biogenesis are the main outputs from a large group of environmental processes participating in the natural material cycle, used in raw materials processing. Bio-oxidation reactions are the main basis for bioleaching procedures, often participating in parallel leaching processes. During the leaching processes of polycomponent sulphide substrates, the factor of process selection also plays an important role, being in direct relation to the electric properties and galvanic effect occurring between the individual components of the leaching substrate. This work gives a summary of the results of a research focused on the possibilities of using biotechnological procedures for treatment of Slovak sulphide ores. The object of the research is extraction of valuable metals, undesirable admixtures and degradation of crystal lattice of sulphides for subsequent chemical leaching processing of precious metals. The results of experiments on the existence of biogenic processes in situ on waste dumps from exploitation containing residual sulphides are also presented. The processes result in acid mine drainage water generation. These waters are strongly mineralised (over 48 g/L) and of low pH; that is why they are very caustic. The arsenic content (2.558 mg/L) in outflowing waters from old mines is high and over the limits set by the law. PMID:24445359

  4. A short scalable route to (-)-α-kainic acid using Pt-catalyzed direct allylic amination.

    PubMed

    Zhang, Ming; Watanabe, Kenji; Tsukamoto, Masafumi; Shibuya, Ryozo; Morimoto, Hiroyuki; Ohshima, Takashi

    2015-03-01

    An increased supply of scarce or inaccessible natural products is essential for the development of more sophisticated pharmaceutical agents and biological tools, and thus the development of atom-economical, step-economical and scalable processes to access these natural products is in high demand. Herein we report the development of a short, scalable total synthesis of (-)-α-kainic acid, a useful compound in neuropharmacology that is, however, limited in supply from natural resources. The synthesis features sequential platinum-catalyzed direct allylic aminations and thermal ene-cyclization, enabling the gram-scale synthesis of (-)-α-kainic acid in six steps and 34% overall yield. PMID:25604395

  5. Citric Acid Enhanced Copper Removal by a Novel Multi-amines Decorated Resin

    PubMed Central

    Ling, Chen; Liu, Fuqiang; Pei, Zhiguo; Zhang, Xiaopeng; Wei, Mengmeng; Zhang, Yanhong; Zheng, Lirong; Zhang, Jing; Li, Aimin; Xing, Baoshan

    2015-01-01

    Cu removal by a novel multi-amines decorated resin (PAMD) from wastewater in the absence or presence of citric acid (CA) was examined. Adsorption capacity of Cu onto PAMD markedly increased by 186% to 5.07 mmol/g in the presence of CA, up to 7 times of that onto four commercial resins under the same conditions. Preloaded and kinetic studies demonstrated adsorption of [Cu-CA] complex instead of CA site-bridging and variations of adsorbate species were qualitatively illustrated. The interaction configuration was further studied with ESI-MS, FTIR, XPS and XANES characterizations. The large enhancement of Cu adsorption in Cu-CA bi-solutes systems was attributed to mechanism change from single-site to dual-sites interaction in which cationic or neutral Cu species (Cu2+ and CuHL0) coordinated with neutral amine sites and anionic complex species (CuL− and Cu2L22−) directly interacted with protonated amine sites via electrostatic attraction, and the ratio of the two interactions was approximately 0.5 for the equimolar bi-solutes system. Moreover, commonly coexisting ions in wastewaters had no obvious effect on the superior performance of PAMD. Also, Cu and CA could be recovered completely with HCl. Therefore, PAMD has a great potential to efficiently remove heavy metal ions from wastewaters in the presence of organic acids. PMID:25962970

  6. Studies of the biogenic amine transporters. VII. Characterization of a novel cocaine binding site identified with [125I]RTI-55 in membranes prepared from human, monkey and guinea pig caudate.

    PubMed

    Rothman, R B; Silverthorn, M L; Glowa, J R; Matecka, D; Rice, K C; Carroll, F I; Partilla, J S; Uhl, G R; Vandenbergh, D J; Dersch, C M

    1998-04-01

    [125I]RTI-55 is a cocaine analog with high affinity for dopamine (DA) and serotonin (5-HT) transporters. Quantitative ligand binding studies revealed a novel high affinity [125I]RTI-55 binding site assayed under 5-HT transporter (SERT) conditions which has low affinity for almost all classic biogenic amine transporter ligands, including high affinity 5-HT transporter inhibitors such as paroxetine, but which retains high affinity for cocaine analogs. This site, termed SERT(site2) for its detection under 5-HT transporter conditions (not for an association with the SERT) occurs in monkey caudate, human caudate, and guinea pig caudate membranes, but not in rat caudate membranes. SERT(site2) is distinguished from the DA transporter (DAT) and SERT by several criteria, including a distinct ligand-selectivity profile, the inability to detect SERT(site2) in cells stably expressing the cloned human DAT, and insensitivity to irreversible ligands which inhibit [125I]RTI-55 binding to the DAT and SERT. Perhaps the most striking finding about SERT(site2) is that a wide range of representative antidepressant agents have very low affinity for SERT(site2). The affinity of cocaine for this site is not very different from the concentration cocaine achieves in the brain at pharmacological doses. Viewed collectively with the observation that ligands with high affinity for SERT(site2) are mostly cocaine analogs, these data lead us to speculate that actions of cocaine which differ from those of classic biogenic amine uptake inhibitors may be mediated in part via SERT(site2).

  7. Solid polymer substrates and coated fibers containing 2,4,6-trinitrobenzene motifs as smart labels for the visual detection of biogenic amine vapors.

    PubMed

    Pablos, Jesús L; Vallejos, Saúl; Muñoz, Asunción; Rojo, María J; Serna, Felipe; García, Félix C; García, José M

    2015-06-01

    Attempts to polymerize trinitrobenzene derivatives (TNB) have been fruitless so far. Accordingly, polymers containing TNB have not been exploited in spite of their envisaged potential applications. Here, we describe two ways for preparing polymers with TNB moieties thus overcoming the previously reported polymerization impairments. We also report on the exploitation of the materials, both obtained as tractable transparent films and coated fibers, as smart labels for the visual detection of amine vapors. More precisely, amines in the atmosphere surrounding the sensory materials diffuse into them reacting with the TNB motifs forming highly colored Meisenheimer complexes, giving rise to development of color and to the naked eye sensing phenomenon. This is the case of highly volatile amines, such as trimethylamine, produced in food spoilage, specifically in the deterioration of fish or meat, for which the color development of the smart labels can be used as a visual test for food freshness.

  8. Isotopic analyses of nitrogenous compounds from the Murchison meteorite: ammonia, amines, amino acids, and polar hydrocarbons

    NASA Technical Reports Server (NTRS)

    Pizzarello, S.; Feng, X.; Epstein, S.; Cronin, J. R.

    1994-01-01

    The combined volatile bases (ammonia, aliphatic amines, and possibly other bases), ammonia, amino acids, and polar hydrocarbons were prepared from the Murchison meteorite for isotopic analyses. The volatile bases were obtained by cryogenic transfer after acid-hydrolysis of a hot-water extract and analyzed by combined gas chromatography-mass spectrometry of pentafluoropropionyl derivatives. The aliphatic amines present in this preparation comprise a mixture that includes both primary and secondary isomers through C5 at a total concentration of > or = 100 nmoles g-1. As commonly observed for meteoritic organic compounds, almost all isomers through C5 are present, and the concentrations within homologous series decrease with increasing chain length. Ammonia was chromatographically separated from the other volatile bases and found at a concentration of 1.1-1.3 micromoles g-1 meteorite. The ammonia analyzed includes contributions from ammonium salts and the hydrolysis of extractable organic compounds, e.g., carboxamides. Stable isotope analyses showed the volatile bases to be substantially enriched in the heavier isotopes, relative to comparable terrestrial compounds delta D < or = +1221%; delta 13C = +22%; delta 15N = +93%). Ammonia, per se, was found to have a somewhat lower delta 15N value (+69%) than the total volatile bases; consequently, a higher delta 15N (>93%) can be inferred for the other bases, which include the amines. Solvent-extractable polar hydrocarbons obtained separately were found to be enriched in 15N (delta 15N = +104%). Total amino acids, prepared from a hydrolyzed hot-water extract by cation exchange chromatography, gave a delta 15N of +94%, a value in good agreement with that obtained previously. Nitrogen isotopic data are also given for amino acid fractions separated chromatographically. The delta 15N values of the Murchison soluble organic compounds analyzed to date fall within a rather narrow range (delta 15N = +94 +/- 8%), an observation

  9. Sulfuric Acid Nucleation with NH3, Methyl, Dimethyl, and Trimethyl Amines

    NASA Astrophysics Data System (ADS)

    Hanson, D. R.; Volz, K.; Glasoe, W.; Panta, B.

    2013-12-01

    Nucleation of particles from sulfuric acid, water, and nitrogen base molecules was studied within a cylindrical flow reactor. The particles formed from these vapors were detected with a nano Mobility Particle Sizer coupled to a Diethylene Glycol Ultrafine Condensation Particle Counter. The effects of ammonia and small alkyl amines on particle formation with sulfuric acid vapor were very large. Enhancements of particle numbers by factors of thousands to millions indicates that these species have powerful effects on nucleation of sulfuric acid molecules. Power dependencies for particle numbers on sulfuric acid and nitrogen bases elucidates the chemical content of the critical clusters and this helps to shed light on the nucleation mechanisms. The details of the particle detection efficiencies, information on the extent of particle growth, and independently determined cluster thermodynamics help to verify these results and to extrapolate them to atmospheric conditions.

  10. Enhancing polysaccharide-mediated delivery of nucleic acids through functionalization with secondary and tertiary amines.

    PubMed

    Ghosn, Bilal; Kasturi, Sudhir Pai; Roy, Krishnendu

    2008-01-01

    Chitosan is a polysaccharide that has generated significant interest as a non-viral gene delivery vehicle due to its cationic and biocompatible characteristics. However, transfection efficiency of chitosan is significantly lower compared to other cationic gene delivery agents, e.g. polyethyleneimine (PEI), dendrimers or cationic lipids. This is primarily attributed to its minimal solubility and low buffering capacity at physiological pH leading to poor endosomal escape of the gene carrier and inefficient cytoplasmic decoupling of the complexed nucleic acid. Here we have developed an imidazole acetic acid (IAA)-modified chitosan to introduce secondary and tertiary amines to the polymer in order to improve its endosomal buffering and solubility. The modified polymer was characterized by ninhydrin and (1)H NMR assays for degree of modification, while buffering and solubility were analyzed by acid titration. Nanocomplex formation, studied at various polymer-nucleic acid ratios, showed an increase in particle zeta potential for chitosan-IAA, as well as an increase in the effective diameter. Up to 100-fold increase in transfection efficiency of pDNA was seen for chitosan-IAA as compared to native chitosan, nearly matching that of PEI. In addition, transfection of siRNA by the modified polymers showed efficient gene knockdown equivalent to commercially available siPORT Amines. Collectively, these results demonstrate the potential of the imidazole-grafted chitosan as a biocompatible and effective delivery vehicle for both pDNA and siRNA.

  11. [Stardust Amines

    NASA Technical Reports Server (NTRS)

    Dworkin, Jason P.

    2008-01-01

    We investigated the abundances of amino acids and amines, as well as their enantiomeric composition in water extracts of comet Wild 2 exposed aerogel and aluminum foils returned by Stardust using liquid chromatography with UV fluorescence detection and time of flight-mass spectrometry (LC-FD/ToF-MS). A suite of amino acids and amines including glycine, L-alanine, methylamine (MA), and ethylamine (EA) were identified in the Stardust bulk aerogel. With the exception of MA and EA, all other primary amines detected in comet-exposed aerogels were also present in the aerogel witness tile that was not exposed to Wild 2, suggesting that most amines are terrestrial in origin. The enhanced abundances of MA, EA, and possibly glycine in comet-exposed aerogel compared to controls, coupled with MA to EA ratios (approx.1 to 2) that are distinct from preflight aerogels (approx.7 to lo), suggest that these amines were captured from Wild 2. The presence of cometary amines in Stardust material supports the hypothesis that comets were an important source of prebiotic organics on the early Earth. To better understand their origin, a systematic study of all these species with C, N, and H compound specific isotopic analysis (CSIA) via gas chromatography quadrupole mass spectrometry in with parallel with combustion isotope ratio mass spectrometry (GC-QMS/IRMS) is being conducted. We will discuss our latest C-CSIA measurements and what they indicate about the origin of the amino acids extracted from Stardust samples.

  12. Potential role of stabilized Criegee radicals in sulfuric acid production in a high biogenic VOC environment.

    PubMed

    Kim, Saewung; Guenther, Alex; Lefer, Barry; Flynn, James; Griffin, Robert; Rutter, Andrew P; Gong, Longwen; Cevik, Basak Karakurt

    2015-03-17

    We present field observations made in June 2011 downwind of Dallas-Fort Worth, TX, and evaluate the role of stabilized Criegee radicals (sCIs) in gaseous sulfuric acid (H2SO4) production. Zero-dimensional model calculations show that sCI from biogenic volatile organic compounds composed the majority of the sCIs. The main uncertainty associated with an evaluation of H2SO4 production from the sCI reaction channel is the lack of experimentally determined reaction rates for sCIs formed from isoprene ozonolysis with SO2 along with systematic discrepancies in experimentally derived reaction rates between other sCIs and SO2 and water vapor. In general, the maximum of H2SO4 production from the sCI channel is found in the late afternoon as ozone increases toward the late afternoon. The sCI channel, however, contributes minor H2SO4 production compared with the conventional OH channel in the mid-day. Finally, the production and the loss rates of H2SO4 are compared. The application of the recommended mass accommodation coefficient causes significant overestimation of H2SO4 loss rates compared with H2SO4 production rates. However, the application of a lower experimental value for the mass accommodation coefficient provides good agreement between the loss and production rates of H2SO4. The results suggest that the recommended coefficient for the H2O surface may not be suitable for this relatively dry environment. PMID:25700170

  13. New Particle Formation and Growth from Methanesulfonic Acid, Amines, Water, and Organics

    NASA Astrophysics Data System (ADS)

    Arquero, K. D.; Ezell, M. J.; Finlayson-Pitts, B. J.

    2014-12-01

    Particles in the atmosphere can influence visibility, negatively impact human health, and affect climate. The largest uncertainty in determining global radiative forcing is attributed to atmospheric aerosols. While new particle formation in many locations is correlated with sulfuric acid in air, neither the gas-phase binary nucleation of H2SO4-H2O nor the gas-phase ternary nucleation of H2SO4-NH3-H2O alone can fully explain observations. An additional potential particle source, based on previous studies in this laboratory, is methanesulfonic acid (MSA) with amines and water vapor. However, organics are ubiquitous in the atmosphere, with secondary organic aerosol (SOA) being a major component of particles. Organics could be involved in the initial stages of particle formation by enhancing or inhibiting nucleation from sulfuric acid or MSA, in addition to contributing to their growth to form SOA. Experiments to measure the effects of a series of organics of varying structure on particle formation and growth from MSA, amines, and water were performed in a custom-built small volume aerosol flow tube reactor. Analytical instruments and techniques include a scanning mobility particle sizer to measure particle size distributions, sampling onto a weak cation exchange resin with analysis by ion chromatography to measure amine concentrations, and filter collection and analysis by ultra-high performance liquid chromatography tandem mass spectrometry to measure MSA concentrations. Organics were measured by atmospheric pressure chemical ionization tandem mass spectrometry. The impact of these organics on the initial particle formation as well as growth will be reported. The outcome is an improved understanding of fundamental chemistry of nucleation and growth to ultimately be incorporated into climate models to better predict how particles affect the global climate budget.

  14. Kinetic mechanism and structural requirements of the amine-catalyzed decarboxylation of oxaloacetic acid.

    PubMed

    Thalji, Nabil K; Crowe, William E; Waldrop, Grover L

    2009-01-01

    The kinetic and chemical mechanism of amine-catalyzed decarboxylation of oxaloacetic acid at pH 8.0 has been reevaluated using a new and versatile assay. Amine-catalyzed decarboxylation of oxaloacetic acid proceeds via the formation of an imine intermediate, followed by decarboxylation of the intermediate and hydrolysis to yield pyruvate. The decrease in oxaloacetic acid was coupled to NADH formation by malate dehydrogenase, which allowed the rates of both initial carbinolamine formation (as part of the imination step) and decarboxylation to be determined. By comparing the rates observed for a variety of amines and, in particular, diamines, the structural and electronic requirements for diamine-catalyzed decarboxylation at pH 8.0 were identified. At pH 8.0, monoamines were found to be very poor catalysts, whereas some diamines, most notably ethylenediamine, were excellent catalysts. The results indicate that the second amino group of diamines enhances the rate of imine formation by acting as a proton shuttle during the carbinolamine formation step, which enables diamines to overcome high levels of solvation that would otherwise inhibit carbinolamine, and thus imine, formation. The presence of the second amino group may also enhance the rate of the carbinolamine dehydration step. In contrast to the findings of previous reports, the second amino group participates in the reaction by enhancing the rate of decarboxylation via hydrogen-bonding to the imine nitrogen to either stabilize the negative charge that develops on the imine during decarboxylation or preferentially stabilize the reactive imine over the unreactive enamine tautomer. These results provide insight into the precise catalytic mechanism of several enzymes whose reactions are known to proceed via an imine intermediate.

  15. Enzymatic synthesis of enantiopure alpha- and beta-amino acids by phenylalanine aminomutase-catalysed amination of cinnamic acid derivatives.

    PubMed

    Wu, Bian; Szymanski, Wiktor; Wietzes, Piet; de Wildeman, Stefaan; Poelarends, Gerrit J; Feringa, Ben L; Janssen, Dick B

    2009-01-26

    The phenylalanine aminomutase (PAM) from Taxus chinensis catalyses the conversion of alpha-phenylalanine to beta-phenylalanine, an important step in the biosynthesis of the N-benzoyl phenylisoserinoyl side-chain of the anticancer drug taxol. Mechanistic studies on PAM have suggested that (E)-cinnamic acid is an intermediate in the mutase reaction and that it can be released from the enzyme's active site. Here we describe a novel synthetic strategy that is based on the finding that ring-substituted (E)-cinnamic acids can serve as a substrate in PAM-catalysed ammonia addition reactions for the biocatalytic production of several important beta-amino acids. The enzyme has a broad substrate range and a high enantioselectivity with cinnamic acid derivatives; this allows the synthesis of several non-natural aromatic alpha- and beta-amino acids in excellent enantiomeric excess (ee >99 %). The internal 5-methylene-3,5-dihydroimidazol-4-one (MIO) cofactor is essential for the PAM-catalysed amination reactions. The regioselectivity of amination reactions was influenced by the nature of the ring substituent.

  16. Strong Fluorescent Smart Organogel as a Dual Sensing Material for Volatile Acid and Organic Amine Vapors.

    PubMed

    Xue, Pengchong; Yao, Boqi; Wang, Panpan; Gong, Peng; Zhang, Zhenqi; Lu, Ran

    2015-11-23

    An L-phenylalanine derivative (C12PhBPCP) consisting of a strong emission fluorophore with benzoxazole and cyano groups is designed and synthesized to realize dual responses to volatile acid and organic amine vapors. The photophysical properties and self-assembly of the said derivative in the gel phase are also studied. C12PhBPCP can gelate organic solvents and self-assemble into 1 D nanofibers in the gels. UV/Vis absorption spectral results show H-aggregate formation during gelation, which indicates strong exciton coupling between fluorophores. Both wet gel and xerogel emit strong green fluorescence because the cyano group suppresses fluorescence quenching in the self-assemblies. Moreover, the xerogel film with strong green fluorescence can be used as a dual chemosensor for quantitative detection of volatile acid and organic amine vapors with fast response times and low detection limits owing to its large surface area and amplified fluorescence quenching. The detection limits are 796 ppt and 25 ppb for gaseous aniline and trifluoroacetic acid (TFA), respectively.

  17. PROCESS FOR EXTRACTING NEPTUNIUM AND PLUTONIUM FROM NITRIC ACID SOLUTIONS OF SAME CONTAINING URANYL NITRATE WITH A TERTIARY AMINE

    DOEpatents

    Sheppard, J.C.

    1962-07-31

    A process of selectively extracting plutonium nitrate and neptunium nitrate with an organic solution of a tertiary amine, away from uranyl nitrate present in an aqueous solution in a maximum concentration of 1M is described. The nitric acid concentration is adjusted to about 4M and nitrous acid is added prior to extraction. (AEC)

  18. Trace Amines and the Trace Amine-Associated Receptor 1: Pharmacology, Neurochemistry, and Clinical Implications.

    PubMed

    Pei, Yue; Asif-Malik, Aman; Canales, Juan J

    2016-01-01

    Biogenic amines are a collection of endogenous molecules that play pivotal roles as neurotransmitters and hormones. In addition to the "classical" biogenic amines resulting from decarboxylation of aromatic acids, including dopamine (DA), norepinephrine, epinephrine, serotonin (5-HT), and histamine, other biogenic amines, present at much lower concentrations in the central nervous system (CNS), and hence referred to as "trace" amines (TAs), are now recognized to play significant neurophysiological and behavioral functions. At the turn of the century, the discovery of the trace amine-associated receptor 1 (TAAR1), a phylogenetically conserved G protein-coupled receptor that is responsive to both TAs, such as β-phenylethylamine, octopamine, and tyramine, and structurally-related amphetamines, unveiled mechanisms of action for TAs other than interference with aminergic pathways, laying the foundations for deciphering the functional significance of TAs and its mammalian CNS receptor, TAAR1. Although, its molecular interactions and downstream targets have not been fully elucidated, TAAR1 activation triggers accumulation of intracellular cAMP, modulates PKA and PKC signaling and interferes with the β-arrestin2-dependent pathway via G protein-independent mechanisms. TAAR1 is uniquely positioned to exert direct control over DA and 5-HT neuronal firing and release, which has profound implications for understanding the pathophysiology of, and therefore designing more efficacious therapeutic interventions for, a range of neuropsychiatric disorders that involve aminergic dysregulation, including Parkinson's disease, schizophrenia, mood disorders, and addiction. Indeed, the recent development of novel pharmacological tools targeting TAAR1 has uncovered the remarkable potential of TAAR1-based medications as new generation pharmacotherapies in neuropsychiatry. This review summarizes recent developments in the study of TAs and TAAR1, their intricate neurochemistry and

  19. Trace Amines and the Trace Amine-Associated Receptor 1: Pharmacology, Neurochemistry, and Clinical Implications

    PubMed Central

    Pei, Yue; Asif-Malik, Aman; Canales, Juan J.

    2016-01-01

    Biogenic amines are a collection of endogenous molecules that play pivotal roles as neurotransmitters and hormones. In addition to the “classical” biogenic amines resulting from decarboxylation of aromatic acids, including dopamine (DA), norepinephrine, epinephrine, serotonin (5-HT), and histamine, other biogenic amines, present at much lower concentrations in the central nervous system (CNS), and hence referred to as “trace” amines (TAs), are now recognized to play significant neurophysiological and behavioral functions. At the turn of the century, the discovery of the trace amine-associated receptor 1 (TAAR1), a phylogenetically conserved G protein-coupled receptor that is responsive to both TAs, such as β-phenylethylamine, octopamine, and tyramine, and structurally-related amphetamines, unveiled mechanisms of action for TAs other than interference with aminergic pathways, laying the foundations for deciphering the functional significance of TAs and its mammalian CNS receptor, TAAR1. Although, its molecular interactions and downstream targets have not been fully elucidated, TAAR1 activation triggers accumulation of intracellular cAMP, modulates PKA and PKC signaling and interferes with the β-arrestin2-dependent pathway via G protein-independent mechanisms. TAAR1 is uniquely positioned to exert direct control over DA and 5-HT neuronal firing and release, which has profound implications for understanding the pathophysiology of, and therefore designing more efficacious therapeutic interventions for, a range of neuropsychiatric disorders that involve aminergic dysregulation, including Parkinson's disease, schizophrenia, mood disorders, and addiction. Indeed, the recent development of novel pharmacological tools targeting TAAR1 has uncovered the remarkable potential of TAAR1-based medications as new generation pharmacotherapies in neuropsychiatry. This review summarizes recent developments in the study of TAs and TAAR1, their intricate neurochemistry and

  20. Trace Amines and the Trace Amine-Associated Receptor 1: Pharmacology, Neurochemistry, and Clinical Implications.

    PubMed

    Pei, Yue; Asif-Malik, Aman; Canales, Juan J

    2016-01-01

    Biogenic amines are a collection of endogenous molecules that play pivotal roles as neurotransmitters and hormones. In addition to the "classical" biogenic amines resulting from decarboxylation of aromatic acids, including dopamine (DA), norepinephrine, epinephrine, serotonin (5-HT), and histamine, other biogenic amines, present at much lower concentrations in the central nervous system (CNS), and hence referred to as "trace" amines (TAs), are now recognized to play significant neurophysiological and behavioral functions. At the turn of the century, the discovery of the trace amine-associated receptor 1 (TAAR1), a phylogenetically conserved G protein-coupled receptor that is responsive to both TAs, such as β-phenylethylamine, octopamine, and tyramine, and structurally-related amphetamines, unveiled mechanisms of action for TAs other than interference with aminergic pathways, laying the foundations for deciphering the functional significance of TAs and its mammalian CNS receptor, TAAR1. Although, its molecular interactions and downstream targets have not been fully elucidated, TAAR1 activation triggers accumulation of intracellular cAMP, modulates PKA and PKC signaling and interferes with the β-arrestin2-dependent pathway via G protein-independent mechanisms. TAAR1 is uniquely positioned to exert direct control over DA and 5-HT neuronal firing and release, which has profound implications for understanding the pathophysiology of, and therefore designing more efficacious therapeutic interventions for, a range of neuropsychiatric disorders that involve aminergic dysregulation, including Parkinson's disease, schizophrenia, mood disorders, and addiction. Indeed, the recent development of novel pharmacological tools targeting TAAR1 has uncovered the remarkable potential of TAAR1-based medications as new generation pharmacotherapies in neuropsychiatry. This review summarizes recent developments in the study of TAs and TAAR1, their intricate neurochemistry and

  1. Synthesis of Aminoboronic Acid Derivatives from Amines and Amphoteric Boryl Carbonyl Compounds.

    PubMed

    Diaz, Diego B; Scully, Conor C G; Liew, Sean K; Adachi, Shinya; Trinchera, Piera; St Denis, Jeffrey D; Yudin, Andrei K

    2016-10-01

    Herein, we demonstrate the use of α-boryl aldehydes and acyl boronates in the synthesis of aminoboronic acid derivatives. This work highlights the untapped potential of boron-substituted iminium ions and offers insights into the behavior of N-methyliminodiacetyl (MIDA) boronates during condensation and tautomerization processes. The preparative value of this contribution lies in the demonstration that various amines, including linear and cyclic peptides, can be readily conjugated with boron-containing fragments. A mild deprotection of amino MIDA-boronates enables access to α- and β-aminoboronic acids in high chemical yields. This simple process should be applicable to the synthesis of a wide range of bioactive molecules as well as precursors for cross-coupling reactions. PMID:27584917

  2. Human immunodeficiency virus trans-activator of transcription peptide detection via ribonucleic acid aptamer on aminated diamond biosensor

    NASA Astrophysics Data System (ADS)

    Rahim Ruslinda, A.; Wang, Xianfen; Ishii, Yoko; Ishiyama, Yuichiro; Tanabe, Kyosuke; Kawarada, Hiroshi

    2011-09-01

    The potential of ribonucleic acid (RNA) as both informational and ligand binding molecule have opened a scenario in the development of biosensors. An aminated diamond-based RNA aptasensor is presented for human immunodeficiency virus (HIV) trans-activator of transcription (Tat) peptide protein detection that not only gives a labeled or label-free detection method but also provides a reusable platform for a simple, sensitive, and selective detection of proteins. The immobilized procedure was based on the binding interaction between positively charged amine terminated diamond and the RNA aptamer probe molecules with the negatively charged surface carboxylic compound linker molecule such as terephthalic acid.

  3. Evaluation of two different extraction methods for chromatographic determination of bioactive amines in tomato products.

    PubMed

    Chiacchierini, E; Restuccia, D; Vinci, G

    2006-05-15

    Bioactive amines are organic bases originating from corresponding amino acid which have undergone decarboxylation by putrefactive bacteria or lactic acid bacteria. When formed by microbial enzymatic decarboxylation of amino acids, they are called " biogenic" and can produce detrimental effects on human health. Many techniques have been developed for extraction and/or clean up of bioactive amines in food, including acidic or organic extraction as well as solid phase extraction. This study deals with the comparison of two different extraction methods, homogenizing and matrix solid phase dispersion, for the chromatographic determination of eight non-volatile bioactive amines in tomato-based products (mashed tomato, biological mashed tomato, concentrated tomato pasta and ketchup) very popular in Italian alimentary habits. In both cases, perchloric acid has been used for analytes extraction and the influence of different parameters affecting amine recoveries have been evaluated. After a derivatization step with dansyl-chloride, samples were analyzed for amines quantitative determination using 1,7-diaminoheptane as internal standard on a C(18)-RP-HPLC-UV system. Method performances were tested and good results of linearity, repeatability and recovery were obtained for all the considered amines. The collected data have shown that ketchup contains the highest levels of amines followed by concentrated tomato pasta, biological mashed tomato and common mashed tomato. Moreover, it has been found that in all samples, putrescine is the most abundant amine followed by tyramine, spermidine and tryptamine. PMID:18970603

  4. Structure of six organic acid-base adducts from 6-bromobenzo[d]thiazol-2-amine and acidic compounds

    NASA Astrophysics Data System (ADS)

    Jin, Shouwen; Zhang, Jing; Wang, Daqi; Tao, Lin; Zhou, Mengjian; Shen, Yinyan; Chen, Quan; Lin, Zhanghui; Gao, Xingjun

    2014-05-01

    Six anhydrous organic acid-base adducts of 6-bromobenzo[d]thiazol-2-amine were prepared with organic acids as 2,4,6-trinitrophenol, salicylic acid, 3,5-dinitrobenzoic acid, 3,5-dinitrosalicylic acid, malonic acid and sebacic acid. The compounds 1-6 were characterized by X-ray diffraction analysis, IR, and elemental analysis. The melting points of all the adducts were given. Of the six adducts, 1, 3, 4, and 5 are organic salts, while 2, and 6 are cocrystals. The supramolecular arrangement in the crystals 2-6 is based on the R22(8) synthon. Analysis of the crystal packing of 1-6 suggests that there are strong NH⋯O, OH⋯N, and OH⋯O hydrogen bonds (charge assisted or neutral) between acid and base components in the supramolecular assemblies. When the hydroxyl group is present in the ortho position of the carboxy, the intramolecular S6 synthon is present, as expected. Besides the classical hydrogen bonding interactions, other noncovalent interactions also play important roles in structure extension. Due to the synergetic effect of these weak interactions, compounds 1-6 display 1D-3D framework structure.

  5. 40 CFR 721.10570 - Cyclic amine reaction product with acetophenone and formaldehyde acid salt (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Cyclic amine reaction product with... SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10570 Cyclic amine reaction product... subject to reporting. (1) The chemical substance identified generically as cyclic amine reaction...

  6. 40 CFR 721.10570 - Cyclic amine reaction product with acetophenone and formaldehyde acid salt (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Cyclic amine reaction product with... SUBSTANCES Significant New Uses for Specific Chemical Substances § 721.10570 Cyclic amine reaction product... subject to reporting. (1) The chemical substance identified generically as cyclic amine reaction...

  7. 15N NMR investigation of the covalent binding of reduced TNT amines to soil humic acid, model compounds, and lignocellulose

    USGS Publications Warehouse

    Thorn, K.A.; Kennedy, K.R.

    2002-01-01

    The five major reductive degradation products of TNT-4ADNT (4-amino-2,6-dinitrotoluene), 2ADNT (2-amino-4,6-dinitrotoluene), 2,4DANT (2,4-diamino-6-nitrotoluene), 2,6DANT (2,6-diamino-4-nitrotoluene), and TAT (2,4,6-triaminotoluene)-labeled with 15N in the amine positions, were reacted with the IHSS soil humic acid and analyzed by 15N NMR spectrometry. In the absence of catalysts, all five amines underwent nucleophilic addition reactions with quinone and other carbonyl groups in the soil humic acid to form both heterocyclic and nonheterocyclic condensation products. Imine formation via 1,2-addition of the amines to quinone groups in the soil humic acid was significant with the diamines and TAT but not the monoamines. Horseradish peroxidase (HRP) catalyzed an increase in the incorporation of all five amines into the humic acid. In the case of the diamines and TAT, HRP also shifted the binding away from heterocyclic condensation product toward imine formation. A comparison of quantitative liquid phase with solid-state CP/MAS 15N NMR indicated that the CP experiment underestimated imine and heterocyclic nitrogens in humic acid, even with contact times optimal for observation of these nitrogens. Covalent binding of the mono- and diamines to 4-methylcatechol, the HRP catalyzed condensation of 4ADNT and 2,4DANT to coniferyl alcohol, and the binding of 2,4DANT to lignocellulose with and without birnessite were also examined.

  8. Calcite growth-rate inhibition by fulvic acid and magnesium ion—Possible influence on biogenic calcite formation

    USGS Publications Warehouse

    Reddy, Michael M.

    2012-01-01

    Increases in ocean surface water dissolved carbon dioxide (CO2) concentrations retard biocalcification by reducing calcite supersaturation (Ωc). Reduced calcification rates may influence growth-rate dependent magnesium ion (Mg) incorporation into biogenic calcite modifying the use of calcifying organisms as paleoclimate proxies. Fulvic acid (FA) at biocalcification sites may further reduce calcification rates. Calcite growth-rate inhibition by FA and Mg, two common constituents of seawater and soil water involved in the formation of biogenic calcite, was measured separately and in combination under identical, highly reproducible experimental conditions. Calcite growth rates (pH=8.5 and Ωc=4.5) are reduced by FA (0.5 mg/L) to 47% and by Mg (10−4 M) to 38%, compared to control experiments containing no added growth-rate inhibitor. Humic acid (HA) is twice as effective a calcite growth-rate inhibitor as FA. Calcite growth rate in the presence of both FA (0.5 mg/L) and Mg (10−4 M) is reduced to 5% of the control rate. Mg inhibits calcite growth rates by substitution for calcium ion at the growth site. In contrast, FA inhibits calcite growth rates by binding multiple carboxylate groups on the calcite surface. FA and Mg together have an increased affinity for the calcite growth sites reducing calcite growth rates.

  9. Versatile and sustainable synthesis of cyclic imides from dicarboxylic acids and amines by Nb2O5 as a base-tolerant heterogeneous Lewis acid catalyst.

    PubMed

    Ali, Md Ayub; Siddiki, S M A Hakim; Kon, Kenichi; Hasegawa, Junya; Shimizu, Ken-Ichi

    2014-10-27

    Catalytic condensation of dicarboxylics acid and amines without excess amount of activating reagents is the most atom-efficient but unprecedented synthetic method of cyclic imides. Here we present the first general catalytic method, proceeding selectively and efficiently in the presence of a commercial Nb2 O5 as a reusable and base-tolerant heterogeneous Lewis acid catalyst. The method is effective for the direct synthesis of pharmaceutically or industrially important cyclic imides, such as phensuximide, N-hydroxyphthalimide (NHPI), and unsubstituted cyclic imides from dicarboxylic acid or anhydrides with amines, hydroxylamine, or ammonia.

  10. AMMO-Prot: amine system project 3D-model finder

    PubMed Central

    Navas-Delgado, Ismael; Montañez, Raúl; Pino-Ángeles, Almudena; Moya-García, Aurelio A; Urdiales, José Luis; Sánchez-Jiménez, Francisca; Aldana-Montes, José F

    2008-01-01

    Background Amines are biogenic amino acid derivatives, which play pleiotropic and very important yet complex roles in animal physiology. For many other relevant biomolecules, biochemical and molecular data are being accumulated, which need to be integrated in order to be effective in the advance of biological knowledge in the field. For this purpose, a multidisciplinary group has started an ontology-based system named the Amine System Project (ASP) for which amine-related information is the validation bench. Results In this paper, we describe the Ontology-Based Mediator developed in the Amine System Project () using the infrastructure of Semantic Directories, and how this system has been used to solve a case related to amine metabolism-related protein structures. Conclusions This infrastructure is used to publish and manage not only ontologies and their relationships, but also metadata relating to the resources committed with the ontologies. The system developed is available at . PMID:18460178

  11. Brønsted acid cocatalysis in photocatalytic intramolecular coupling of tertiary amines: efficient synthesis of 2-arylindols.

    PubMed

    Yuan, Xiaoqian; Wu, Xinxin; Dong, Shupeng; Wu, Guibing; Ye, Jinxing

    2016-08-21

    We report herein a highly efficient intramolecular coupling reaction of tertiary amines and ketones (α,β-unsaturated ketones) by using a Brønsted acid as a cocatalyst, affording 2-arylindols in good to excellent yields (up to 92%) under visible light irradiation at room temperature. PMID:27431277

  12. A Neat Trick Using Oxalic Acid Dihydrate and Potassium Permanganate and Other Experiments with Small Organic Amine or Oxygenated Compounds

    ERIC Educational Resources Information Center

    Kelland, Malcolm A.

    2011-01-01

    Solid potassium permanganate (KMnO[subscript 4]) is shown to react in a variety of ways with small organic amines or oxygenated compounds depending on whether they are liquids or solids and whether water is present. In particular, its reaction with solid oxalic acid dihydrate can be initiated by the moisture in one's breath, making an intriguing…

  13. Enantioselective α-alkenylation of aldehydes with boronic acids via the synergistic combination of copper(II) and amine catalysis.

    PubMed

    Stevens, Jason M; MacMillan, David W C

    2013-08-14

    The enantioselective α-alkenylation of aldehydes has been accomplished using boronic acids via the synergistic combination of copper and chiral amine catalysis. The merger of two highly utilized and robust catalytic systems has allowed for the development of a mild and operationally trivial protocol for the direct formation of α-formyl olefins employing common building blocks for organic synthesis. PMID:23889497

  14. CHEMISTRY OF FOG WATER IN CALIFORNIA'S CENTRAL VALLEY: 2. PHOTOCHEMICAL TRANSFORMATIONS OF AMINO ACIDS AND ALKYL AMINES. (R825433)

    EPA Science Inventory

    Although amino compounds are seemingly ubiquitous in atmospheric particles and deposition, little is known of their fate in the troposphere. We report here on the fate of 21 amino acids and alkyl amines in fog waters from Davis, California, illuminated with simulated sunlight ...

  15. Microwave-assisted decarboxylative three-component coupling of a 2-oxoacetic acid, an amine, and an alkyne.

    PubMed

    Feng, Huangdi; Ermolat'ev, Denis S; Song, Gonghua; Van der Eycken, Erik V

    2011-09-16

    A novel and efficient microwave-assisted decarboxylative three-component coupling of a 2-oxoacetic acid, an amine, and an alkyne (OA(2)-coulpling) has been developed. This new multicomponent coupling constitutes an efficient approach for the synthesis of polysubstituted propargylamines in the presence of a catalytic amount of copper(I) catalyst. PMID:21823621

  16. Nanoparticle strategies for cancer therapeutics: Nucleic acids, polyamines, bovine serum amine oxidase and iron oxide nanoparticles (Review).

    PubMed

    Agostinelli, Enzo; Vianello, Fabio; Magliulo, Giuseppe; Thomas, Thresia; Thomas, T J

    2015-01-01

    Nanotechnology for cancer gene therapy is an emerging field. Nucleic acids, polyamine analogues and cytotoxic products of polyamine oxidation, generated in situ by an enzyme-catalyzed reaction, can be developed for nanotechnology-based cancer therapeutics with reduced systemic toxicity and improved therapeutic efficacy. Nucleic acid-based gene therapy approaches depend on the compaction of DNA/RNA to nanoparticles and polyamine analogues are excellent agents for the condensation of nucleic acids to nanoparticles. Polyamines and amine oxidases are found in higher levels in tumours compared to that of normal tissues. Therefore, the metabolism of polyamines spermidine and spermine, and their diamine precursor, putrescine, can be targets for antineoplastic therapy since these naturally occurring alkylamines are essential for normal mammalian cell growth. Intracellular polyamine concentrations are maintained at a cell type-specific set point through the coordinated and highly regulated interplay between biosynthesis, transport, and catabolism. In particular, polyamine catabolism involves copper-containing amine oxidases. Several studies showed an important role of these enzymes in developmental and disease-related processes in animals through the control of polyamine homeostasis in response to normal cellular signals, drug treatment, and environmental and/or cellular stress. The production of toxic aldehydes and reactive oxygen species (ROS), H2O2 in particular, by these oxidases suggests a mechanism by which amine oxidases can be exploited as antineoplastic drug targets. The combination of bovine serum amine oxidase (BSAO) and polyamines prevents tumour growth, particularly well if the enzyme has been conjugated with a biocompatible hydrogel polymer. The findings described herein suggest that enzymatically formed cytotoxic agents activate stress signal transduction pathways, leading to apoptotic cell death. Consequently, superparamagnetic nanoparticles or other

  17. Effects of succinylcholine and related substances administered into the medial preoptic area on the local EEG, body temperature, heart rate, galvanic skin resistance and biogenic amines.

    PubMed

    Rau, M; Desiraju, T

    1985-01-01

    Succinylcholine (Sch) which is a cholinergic neuromuscular blocker has been known to occasionally lead to episodes of malignant hyperthermia in swine and humans. In order to find whether it produces any hyperthermic effects through action on medial preoptic area, experiments were carried on by administering intracerebrally the chemical into the medial preoptic area through an in-dwelling cannula-cum-electrode in the free moving rat. The changes in body temperature and the local EEG were studied. For comparison purpose, the effects of carbachol, atropine and phenylephrine were also studied. Further, in the curarized state of no muscular activity, the effect of SCh on the preoptic area was again tested and also the changes in the other autonomic parameters of heart rate and galvanic skin resistance (GSR) were studied. It was observed that SCh given into preoptic area caused a clear hyperthermic effect. The effect was countered by prior administration of atropine into the site. After SCh the local EEG changed into a high amplitude slow wave format. The heart rate was not altered but the GSR increased by two-fold. Carbachol caused a rise in body temperature, heart rate and also GSR. SCh also caused a reduction in noradrenaline content of the hypothalamus by 23% while no change in dopamine and serotonin occurred. Serotonin increased by 28% in the brainstem with no change in the other amines. Septum showed an increase of noradrenaline and dopamine contents by 40% and 25% respectively. Keeping in view the monoaminergic connections and thermoregulatory role of the preoptic area, one may postulate that SCh could inhibit the warm sensors and the controls of the dual sympathetic mechanism which normally leads to an increase of sudomotor activity and a decrease of vasomotor activity, the inhibition resulting in rise of body temperature.

  18. Fluorescence Turn-on Enantioselective Recognition of both Chiral Acidic Compounds and α-Amino Acids by a Chiral Tetraphenylethylene Macrocycle Amine.

    PubMed

    Feng, Hai-Tao; Zhang, Xing; Zheng, Yan-Song

    2015-08-21

    New chiral tetraphenylethylene (TPE) macrocycles bearing optically pure amine groups were synthesized and found to have a discriminating ability between the two enantiomers of not only chiral acidic compounds but also α-amino acids by enantioselective aggregation and aggregation-induced emission (AIE) effects. NMR spectra, including 2D-NOESY, disclosed that the host-guest interaction of the macrocycle receptor played a key role in addition to the acid-base interactions.

  19. α(δ')-Michael addition of alkyl amines to dimethyl (E)-hex-2-en-4-ynedioate: synthesis of α,β-dehydroamino acid derivatives.

    PubMed

    Chavan, Arjun S; Deng, Jie-Cheng; Chuang, Shih-Ching

    2013-02-27

    The direct nucleophilic addition of alkyl amines to the α(δ')-carbon atom of dimethyl (E)-hex-2-en-4-ynedioate to generate α,β-dehydroamino acid derivatives is reported. Herein, we have studied the reactivity of various primary and secondary alkyl amines in the α-selective nucleophilic conjugate addition to conjugated dimethyl (E)-hex-2-en-4-ynedioate. The reaction with primary alkyl amines gives only the (2E,4E)-stereoisomer, while that with secondary alkyl amines gives the (2E,4E) and (2Z,4E)-stereoisomers of dimethyl (2-alkylamino)-muconic ester.

  20. Regulation of adipose branched-chain amin acid catabolism enzyme expression and cross-adipose amino acid flux in human obesity

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Elevated blood branched-chain amin acids (BCAA)are often assoicated with insulin resistance and type2 diabetes, which might result from a reduced cellular utilization and/or incomplete BCAA oxidation. White adipose tissue (WAT) has become appreciated as a potential player in whole body BCAA metaboli...

  1. Utilization of hydrogen sulfide from acidic gases produced in treatment with amines

    SciTech Connect

    Lunin, A.F.; Hussein, A.H.; Burdeinaya, T.N.

    1994-07-01

    Treatment with amines is the basic method for removing hydrogen sulfide from gases. When such treatment is used, there is a problem in utilizing the acidic regeneration gases, which consist of carbon dioxide, hydrogen sulfide, and C{sub 1}-C{sub 4} hydrocarbons. If the concentration of hydrogen sulfide in these gases is below 20%, it is best removed by direct oxidation by oxygen to form sulfur or sulfur dioxide, over solid or liquid catalysts. Here we are reporting on an investigation of the activity and selectivity of commercial oxide catalysts in this reaction. Commercial catalysts were used in the direct oxidation of gas containing hydrogen sulfide (2-4% hydrogen sulfide, 1-4% C{sub 1}-C{sub 4} hydrocarbons, remainder carbon dioxide) in a laboratory flow unit with a fixed bed of catalyst. The compositions of the feed and the reaction products were determined by gas-liquid chromatography. The oxidation of hydrogen sulfide may proceed with the formation of either sulfur dioxide or sulfur. Catalyst activity was rated on the basis of the total conversion of hydrogen sulfide, the percentage conversions to elemental sulfur and sulfur dioxide, and the selectivity for the formation of elemental sulfur. The catalyst activities were investigated at temperatures of 170-270{degrees}C, space velocity of feed 300 h{sup -1}, hydrogen sulfide concentration 2-4%, and O{sub 2}: H{sub 2}S ratio 1.

  2. Chromate adsorption on acid-treated and amines-modified clay

    NASA Astrophysics Data System (ADS)

    Hajjaji, M.; Beraa, A.

    2015-03-01

    Acid-treated montmorillonite-rich clay and amines (methylamine, morpholine, and aniline)-modified clay adsorbents were investigated and their abilities to remove chromate from aqueous solution were studied. For the later purpose, kinetic studies were carried out under different operating conditions (chromate concentration, adsorbent content, and temperature), and adsorption isotherm measurements were performed. It was found that the kinetic of adsorption was fast and the data followed the pseudo-second rate equation. The rate of adsorption was controlled by the intra-particle diffusion and mass transfer through the liquid film, and the relative importance of these limiting steps depended on the operating conditions. Chromate adsorption was an endothermic process and took place spontaneously by physisorption. The free energy at 25 ≤ T ≤ 40 °C varied from -1.5 to -46 kJ/mol. Adsorption isotherms of Na+-saturated clay (AN), acid-treated clay (AA), and methylamine-clay and morpholine-clay (A-Me, A-Mo) were type V, whereas those of aniline-clay (A-An) were type III. The estimated maximum uptakes were 105, 29, 15, 11, and 10 mmol/kg for A-An, AN, A-Mo, AA, and A-Me, respectively. The mechanism of chromate adsorption was discussed based on the shape of the isotherms. Considering for instance the most efficient absorbent (A-An), the isotherm followed the Freundlich equation and hydrogen chromate (the main stable form at working pH) adsorbed to solid particles once aniline species were entirely desorbed.

  3. Online measurement of biogenic organic acids in the boreal forest using atmospheric pressure chemical ionization mass spectrometry (APCI-MS)

    NASA Astrophysics Data System (ADS)

    Vogel, A. L.; Brüggemann, M.; ńijälä, M.; Ehn, M.; Junninen, H.; Corrigan, A. L.; Petäjä, T.; Worsnop, D. R.; Russell, L. M.; Kulmala, M.; Williams, J.; Hoffmann, T.

    2012-04-01

    Emission of biogenic volatile organic compounds (BVOCs) by vegetation in the boreal forest and their subsequent atmospheric oxidation leads to the formation of secondary organic aerosol (SOA) which has important impacts on climate and human health. Oxidation of BVOCs produces a variety of mostly unidentified species in oxygenated organic aerosol (OOA). Presently aerosol mass spectrometers (AMS) are able to determine quantitative information about the relative oxygen to carbon content of organic aerosols and thereby reveal the photochemical age and volatility of organic aerosol by distinguishing between low volatile oxygenated organic aerosol (LV-OOA), semivolatile oxygenated organic aerosol (SV-OOA) and hydrocarbon like organic aerosol (HOA)[1]. However, the AMS can usually not be used to measure and quantify single organic compounds such as individual biogenic organic marker compounds. Here we show the results of online measurements of gas and particle phase biogenic acids during HUMPPA-COPEC 2010 at Hyytiälä, Finland. This was achieved by coupling a self built miniature Versatile Aerosol Concentration Enrichment System (mVACES) as described by Geller et al. [2] with an Atmospheric Pressure Chemical Ionization Ion Trap Mass Spectrometer (APCI IT MS; Hoffmann et al., [3]). The benefits of the on-line APCI-MS are soft ionization with little fragmentation compared to AMS, high measurement frequency and less sampling artifacts than in the common procedure of taking filter samples, extraction and detection with LC-MS. Furthermore, the ion trap of the instrument allows MS/MS experiments to be performed by isolation of single m/z ratios of selected molecular species. By subsequent addition of energy, the trapped ions form characteristic fragments which enable structural insight on the molecular level. Comparison of APCI-MS data to AMS data, acquired with a C-ToF-AMS [4], revealed a good correlation coefficient for total organics and sulphate. Furthermore, data show

  4. Neuropeptides, amines and amino acids in an elementary insect ganglion: functional and chemical anatomy of the unfused abdominal ganglion.

    PubMed

    Nässel, D R

    1996-01-01

    The insect ventral nerve cord consists of metamerically repeated ganglia subserving the thoracic and abdominal segments. The abdominal ganglia control basic functions such as respiration, circulation, heartbeat, diuresis, hindgut motility, functions of the genitalia and ovipositor and abdominal posture. Some of this control is by efferent innervation of target tissues but hormonal control also is exerted by abdominal neurosecretory cells via release from neurohemal organs or other release sites. The present review summarizes what is known about the distribution of neurotransmitters, monoamines and neuropeptides in the abdominal ganglia of different insect species. Special emphasis is on the unfused abdominal ganglion, since this is the least complex of all central ganglia and therefore may reveal the minimum number of neuroactive compounds utilized in neurotransmission, neuromodulation and neurohormonal control. Both GABA and glutamate are present in both interneurons and motoneurons, whereas biogenic amines such as serotonin, dopamine and histamine are found primarily in interneurons (although some cases of sensory cells and efferent neurons are known). Octopamine can be seen both in interneurons, efferent neurons and neurosecretory cells. A large number (about 20 different main types) of neuropeptides has been indicated in abdominal ganglia. Each peptide has a very specific distribution pattern. Depending on the peptide type, the localization is known to be in interneurons, neurosecretory cells or motoneurons, or combinations of these. The structure and known functions of the different neuropeptides in different insect species are summarized in some detail. Both GABA and glutamate appear to have roles as fast neurotransmitters, whereas amines and neuropeptides seem to have modulatory roles both within the CNS and at peripheral targets. After a comprehensive overview of different substances in studied insect species, the unfused abdominal ganglia from the moth

  5. Significance of Biogenic Amines in Cold-Smoked Fish and Their Relation to Microbiological Characteristics of Products Available in Portuguese Retail Markets.

    PubMed

    da Silva, Manuela V; Gibbs, Paul

    2015-01-01

    Studies on microbial characterization of cold-smoked salmon and salmon trout during cold storage were performed on samples available in the Portuguese market. Samples were also classified microbiologically according to guidelines for ready-to-eat (RTE) products. Further investigations on sample variability and microbial abilities to produce tyramine and histamine were also performed. The coefficient of variation for viable counts of different groups of microorganisms of samples collected at retail market point was high in the first 2 wk of storage, mainly in the Enterobacteriaceae group and aerobic plate count (APC), suggesting that microbiological characteristics of samples were different in numbers, even within the same batch from the same producer. This variation seemed to be decreased when storage and temperature were controlled under lab conditions. The numbers of Enterobacteriaceae were influenced by storage temperature, as indicated by low microbial numbers in samples from controlled refrigeration. Lactic acid bacteria (LAB) and Enterobacteriaceae were predominant in commercial products, a significant percentage of which were tyramine and less histamine producers. These results might be influenced by (1) the technological processes in the early stages of production, (2) contamination during the smoking process, and (3) conditions and temperature fluctuations during cold storage at retail market point of sale. PMID:26167759

  6. Primordial synthesis of amines and amino acids in a 1958 Miller H2S-rich spark discharge experiment.

    PubMed

    Parker, Eric T; Cleaves, Henderson J; Dworkin, Jason P; Glavin, Daniel P; Callahan, Michael; Aubrey, Andrew; Lazcano, Antonio; Bada, Jeffrey L

    2011-04-01

    Archived samples from a previously unreported 1958 Stanley Miller electric discharge experiment containing hydrogen sulfide (H(2)S) were recently discovered and analyzed using high-performance liquid chromatography and time-of-flight mass spectrometry. We report here the detection and quantification of primary amine-containing compounds in the original sample residues, which were produced via spark discharge using a gaseous mixture of H(2)S, CH(4), NH(3), and CO(2). A total of 23 amino acids and 4 amines, including 7 organosulfur compounds, were detected in these samples. The major amino acids with chiral centers are racemic within the accuracy of the measurements, indicating that they are not contaminants introduced during sample storage. This experiment marks the first synthesis of sulfur amino acids from spark discharge experiments designed to imitate primordial environments. The relative yield of some amino acids, in particular the isomers of aminobutyric acid, are the highest ever found in a spark discharge experiment. The simulated primordial conditions used by Miller may serve as a model for early volcanic plume chemistry and provide insight to the possible roles such plumes may have played in abiotic organic synthesis. Additionally, the overall abundances of the synthesized amino acids in the presence of H(2)S are very similar to the abundances found in some carbonaceous meteorites, suggesting that H(2)S may have played an important role in prebiotic reactions in early solar system environments. PMID:21422282

  7. Primordial Synthesis of Amines and Amino Acids in a 1958 Miller H2S-Rich Spark Discharge Experiment

    NASA Technical Reports Server (NTRS)

    Parker, Eric T.; Cleaves, Henderson J.; Dworkin, Jason P.; Glavin, Daniel P.; Callahan, Michael; Aubrey, Andrew; Lazcano, Antonio; Bada, Jeffrey L.

    2011-01-01

    Archived samples from a previously unreported 1958 Stanley Miller electric discharge experiment containing hydrogen sulfide (H2S) were recently discovered and analyzed using high-performance liquid chromatography and time-of-flight mass spectrometry. We report here the detection and quantification of primary amine-containing compounds in the original sample residues, which were produced via spark discharge using a gaseous mixture of H2S, CH4, NH3, and CO2. A total of 23 amino acids and 4 amines, including 7 organosulfur compounds, were detected in these samples. The major amino acids with chiral centers are racemic within the accuracy of the measurements, indicating that they are not contaminants introduced during sample storage. This experiment marks the first synthesis of sulfur amino acids from spark discharge experiments designed to imitate primordia! environments. The relative yield of some amino acids, in particular the isomers of aminobutyric acid, are the highest ever found in a spark discharge experiment. The simulated primordial conditions used by Miller may serve as a model for early volcanic plume chemistry and provide insight to the possible roles such plumes may have played in abiotic organic synthesis. Additionally, the overall abundances of the synthesized amino acids in the presence of H2S are very similar to the abundances found in some carbonaceous meteorites, suggesting that H2S may have played an important role in prebiotic reactions in early solar system environments.

  8. Primordial synthesis of amines and amino acids in a 1958 Miller H2S-rich spark discharge experiment

    PubMed Central

    Parker, Eric T.; Cleaves, Henderson J.; Dworkin, Jason P.; Glavin, Daniel P.; Callahan, Michael; Aubrey, Andrew; Lazcano, Antonio; Bada, Jeffrey L.

    2011-01-01

    Archived samples from a previously unreported 1958 Stanley Miller electric discharge experiment containing hydrogen sulfide (H2S) were recently discovered and analyzed using high-performance liquid chromatography and time-of-flight mass spectrometry. We report here the detection and quantification of primary amine-containing compounds in the original sample residues, which were produced via spark discharge using a gaseous mixture of H2S, CH4, NH3, and CO2. A total of 23 amino acids and 4 amines, including 7 organosulfur compounds, were detected in these samples. The major amino acids with chiral centers are racemic within the accuracy of the measurements, indicating that they are not contaminants introduced during sample storage. This experiment marks the first synthesis of sulfur amino acids from spark discharge experiments designed to imitate primordial environments. The relative yield of some amino acids, in particular the isomers of aminobutyric acid, are the highest ever found in a spark discharge experiment. The simulated primordial conditions used by Miller may serve as a model for early volcanic plume chemistry and provide insight to the possible roles such plumes may have played in abiotic organic synthesis. Additionally, the overall abundances of the synthesized amino acids in the presence of H2S are very similar to the abundances found in some carbonaceous meteorites, suggesting that H2S may have played an important role in prebiotic reactions in early solar system environments. PMID:21422282

  9. Saponification of esters of chiral alpha-amino acids anchored through their amine function on solid support.

    PubMed

    Cantel, Sonia; Desgranges, Stéphane; Martinez, Jean; Fehrentz, Jean-Alain

    2004-06-01

    Anchoring an alpha-amino acid residue by its amine function onto a solid support is an alternative to develop chemistry on its carboxylic function. This strategy can involve the use of amino-acid esters as precursors of the carboxylic function. A complete study on the Wang-resin was performed to determine the non racemizing saponification conditions of anchored alpha-amino esters. The use of LiOH, NaOH, NaOSi(Me)3, various solvents and temperatures were tested for this reaction. After saponification and cleavage from the support, samples were examined through their Marfey's derivatives by reversed phase HPLC to evaluate the percentage of racemization.

  10. Studies of the biogenic amine transporters. IV. Demonstration of a multiplicity of binding sites in rat caudate membranes for the cocaine analog [125I]RTI-55.

    PubMed

    Rothman, R B; Cadet, J L; Akunne, H C; Silverthorn, M L; Baumann, M H; Carroll, F I; Rice, K C; de Costa, B R; Partilla, J S; Wang, J B

    1994-07-01

    The drug 3 beta-[4'-iodophenyl]tropan-2 beta-carboxylic acid methyl ester (RTI-55) is a cocaine congener with high affinity for the dopamine transporter (Kd < 1 nM). The present study characterized [125I]RTI-55 binding to membranes prepared from rat, monkey and human caudates and COS cells transiently expressing the cloned rat dopamine (DA) transporter. Using the method of binding surface analysis, two binding sites were resolved in rat caudate: a high-capacity binding site (site 1, Bmax = 11,900 fmol/mg of protein) and a low-capacity site (site 2, Bmax = 846 fmol/mg of protein). The Kd (or Ki) values of selected drugs at the two sites were as follows: (Ki for high-capacity site and Ki for low-capacity site, respectively): RTI-55 (0.76 and 0.21 nM), 1-[2-diphenyl-methoxy)ethyl]-4-(3-phenylpropyl)piperazine (0.79 and 358 nM), mazindol (37.6 and 631 nM), 2 beta-carbomethoxy-3 beta-(4-fluorophenyl)tropane (45.0 and 540 nM) and cocaine (341 and 129 nM). Nisoxetine, a selective noradrenergic uptake blocker, had low affinity for both sites. Serotonergic uptake blockers had a high degree of selectivity and high affinity for the low-capacity binding site (Ki of citalopram = 0.38 nM; Ki of paroxetine = 0.033 nM). The i.c.v. administration of 5,7-dihydroxytryptamine to rats pretreated with nomifensine (to protect dopaminergic and noradrenergic nerve terminals) selectively decreased the Bmax of site 2, strongly supporting the idea that site 2 is a binding site on the serotonin (5-HT) transporter. This serotonergic lesion also increased the affinity of [125I]RTI-55 for the DA transporter by 10-fold. The ligand selectivity of the caudate 5-HT transporter was different from the [I125]RTI-55 binding site on the 5-HT transporter present in membranes prepared from whole rat brain minus caudate. The [125I]RTI-55 binding to the DA transporter was further resolved into two components, termed sites 1a and 1b, by using human and monkey (Macaca mulatta) caudate membranes but not the

  11. Metallurgical and Biological Activity of Peroxo Complexes of Molybdenum (VI) Containing Organic Acid and Amine Bases

    NASA Astrophysics Data System (ADS)

    Nasrin, Jahanara; Saidul Islam, M.

    This study describes with the preparation, characterization and bioactivity of peroxo complexes [A: MoO(O2)(gly)(Q); B: MoO(O2)(ala)(2-pic)]of Mo(VI)] containing organic acid and amine bases. Both the complexes A and B were characterized by a variety of physicochemical techniques, viz., elemental analyses, molar conductivity, IR, NMR and electronic spectral studies. The analytical data were in good agreement with the proposed emperical formulae of both the complexes. The molar conductance values indicated both the complexes are non-electrolytes in DMF revealing that the anions are covalently bonded in all the cases. The magnetic moment values indicated that both the complexes were dimagnetic in nature suggesting that there were no changes in the oxidation states of the metal ions upon complexation. The electronic spectral data of the complexes A and B showed bands at 315-355 nm region due to the charge transfers band only. The antimicrobial properties of the peroxo complexes of Mo(VI) indicated that both the complexes were stronger antibacterial and antifungal agents. However, the highest antifungal activity was shown in the complex B against A. niger (16 mm) while the complex A of Mo(VI) showed lowest activity (10 mm). The MIC experiment showed that the complex B of Mo(VI) were more potent against all the bacteria tested than the complex A. Results showed that the complex A of Mo(VI) exhibits more toxic to brine shrimp compared to complex B of Mo(VI) indicating the lower values of LC50 for both the exposure 16 and 36 h.

  12. Revealing biogenic sulfuric acid corrosion in sludge digesters: detection of sulfur-oxidizing bacteria within full-scale digesters.

    PubMed

    Huber, B; Drewes, J E; Lin, K C; König, R; Müller, E

    2014-01-01

    Biogenic sulfuric acid corrosion (BSA) is a costly problem affecting both sewerage infrastructure and sludge handling facilities such as digesters. The aim of this study was to verify BSA in full-scale digesters by identifying the microorganisms involved in the concrete corrosion process, that is, sulfate-reducing (SRB) and sulfur-oxidizing bacteria (SOB). To investigate the SRB and SOB communities, digester sludge and biofilm samples were collected. SRB diversity within digester sludge was studied by applying polymerase chain reaction-denaturing gradient gel electrophoresis (PCR-DGGE) targeting the dsrB-gene (dissimilatory sulfite reductase beta subunit). To reveal SOB diversity, cultivation dependent and independent techniques were applied. The SRB diversity studies revealed different uncultured SRB, confirming SRB activity and H2S production. Comparable DGGE profiles were obtained from the different sludges, demonstrating the presence of similar SRB species. By cultivation, three pure SOB strains from the digester headspace were obtained including Acidithiobacillus thiooxidans, Thiomonas intermedia and Thiomonas perometabolis. These organisms were also detected with PCR-DGGE in addition to two new SOB: Thiobacillus thioparus and Paracoccus solventivorans. The SRB and SOB responsible for BSA were identified within five different digesters, demonstrating that BSA is a problem occurring not only in sewer systems but also in sludge digesters. In addition, the presence of different SOB species was successfully associated with the progression of microbial corrosion. PMID:25353947

  13. Revealing biogenic sulfuric acid corrosion in sludge digesters: detection of sulfur-oxidizing bacteria within full-scale digesters.

    PubMed

    Huber, B; Drewes, J E; Lin, K C; König, R; Müller, E

    2014-01-01

    Biogenic sulfuric acid corrosion (BSA) is a costly problem affecting both sewerage infrastructure and sludge handling facilities such as digesters. The aim of this study was to verify BSA in full-scale digesters by identifying the microorganisms involved in the concrete corrosion process, that is, sulfate-reducing (SRB) and sulfur-oxidizing bacteria (SOB). To investigate the SRB and SOB communities, digester sludge and biofilm samples were collected. SRB diversity within digester sludge was studied by applying polymerase chain reaction-denaturing gradient gel electrophoresis (PCR-DGGE) targeting the dsrB-gene (dissimilatory sulfite reductase beta subunit). To reveal SOB diversity, cultivation dependent and independent techniques were applied. The SRB diversity studies revealed different uncultured SRB, confirming SRB activity and H2S production. Comparable DGGE profiles were obtained from the different sludges, demonstrating the presence of similar SRB species. By cultivation, three pure SOB strains from the digester headspace were obtained including Acidithiobacillus thiooxidans, Thiomonas intermedia and Thiomonas perometabolis. These organisms were also detected with PCR-DGGE in addition to two new SOB: Thiobacillus thioparus and Paracoccus solventivorans. The SRB and SOB responsible for BSA were identified within five different digesters, demonstrating that BSA is a problem occurring not only in sewer systems but also in sludge digesters. In addition, the presence of different SOB species was successfully associated with the progression of microbial corrosion.

  14. Sulfonated reduced graphene oxide as a highly efficient catalyst for direct amidation of carboxylic acids with amines using ultrasonic irradiation.

    PubMed

    Mirza-Aghayan, Maryam; Tavana, Mahdieh Molaee; Boukherroub, Rabah

    2016-03-01

    Sulfonated reduced graphene oxide nanosheets (rGO-SO3H) were prepared by grafting sulfonic acid-containing aryl radicals onto chemically reduced graphene oxide (rGO) under sonochemical conditions. rGO-SO3H catalyst was characterized by Fourier-transform infrared (FT-IR) spectroscopy, Raman spectroscopy, scanning electron microscopy (SEM), X-ray diffraction (XRD), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC) and X-ray photoelectron spectroscopy (XPS). rGO-SO3H catalyst was successfully applied as a reusable solid acid catalyst for the direct amidation of carboxylic acids with amines into the corresponding amides under ultrasonic irradiation. The direct sonochemical amidation of carboxylic acid takes place under mild conditions affording in good to high yields (56-95%) the corresponding amides in short reaction times.

  15. Enhanced Photocatalytic Performance of ZnS for Reversible Amination of α-oxo Acids by Hydrothermal Treatment

    NASA Astrophysics Data System (ADS)

    Wang, Wei; Li, Qiliang; Liu, Xiaoyang; Yang, Yanqiang; Su, Wenhui

    2012-08-01

    To understand how life could have originated on early Earth, it is essential to know what biomolecules and metabolic pathways are shared by extant organisms and what organic compounds and their chemical reaction channels were likely to have been primordially available during the initial phase of the formation of prebiotic metabolism. In a previous study, we demonstrated for the first time the reversible amination of α-oxo acids on the surface of photo-illuminated ZnS. The sulfide mineral is a typical component at the periphery of submarine hydrothermal vents which has been frequently argued as a very attractive venue for the origin of life. In this work, in order to simulate more closely the precipitation environments of ZnS in the vent systems, we treated newly-precipitated ZnS with hydrothermal conditions and found that its photocatalytic power was significantly enhanced because the relative crystallinity of the treated sample was markedly increased with increasing temperature. Since the reported experimental conditions are believed to have been prevalent in shallow-water hydrothermal vents of early Earth and the reversible amination of α-oxo acids is a key metabolic pathway in all extant life forms, the results of this work provide a prototypical model of the prebiotic amino acid redox metabolism. The amino acid dehydrogenase-like chemistry on photo-irradiated ZnS surfaces may advance our understanding of the establishment of archaic non-enzymatic metabolic systems.

  16. Enhanced photocatalytic performance of ZnS for reversible amination of α-oxo acids by hydrothermal treatment.

    PubMed

    Wang, Wei; Li, Qiliang; Liu, Xiaoyang; Yang, Yanqiang; Su, Wenhui

    2012-08-01

    To understand how life could have originated on early Earth, it is essential to know what biomolecules and metabolic pathways are shared by extant organisms and what organic compounds and their chemical reaction channels were likely to have been primordially available during the initial phase of the formation of prebiotic metabolism. In a previous study, we demonstrated for the first time the reversible amination of α-oxo acids on the surface of photo-illuminated ZnS. The sulfide mineral is a typical component at the periphery of submarine hydrothermal vents which has been frequently argued as a very attractive venue for the origin of life. In this work, in order to simulate more closely the precipitation environments of ZnS in the vent systems, we treated newly-precipitated ZnS with hydrothermal conditions and found that its photocatalytic power was significantly enhanced because the relative crystallinity of the treated sample was markedly increased with increasing temperature. Since the reported experimental conditions are believed to have been prevalent in shallow-water hydrothermal vents of early Earth and the reversible amination of α-oxo acids is a key metabolic pathway in all extant life forms, the results of this work provide a prototypical model of the prebiotic amino acid redox metabolism. The amino acid dehydrogenase-like chemistry on photo-irradiated ZnS surfaces may advance our understanding of the establishment of archaic non-enzymatic metabolic systems.

  17. Simplified mechanism for new particle formation from methanesulfonic acid, amines, and water via experiments and ab initio calculations

    PubMed Central

    Dawson, Matthew L.; Varner, Mychel E.; Perraud, Véronique; Ezell, Michael J.; Gerber, R. Benny; Finlayson-Pitts, Barbara J.

    2012-01-01

    Airborne particles affect human health and significantly influence visibility and climate. A major fraction of these particles result from the reactions of gaseous precursors to generate low-volatility products such as sulfuric acid and high-molecular weight organics that nucleate to form new particles. Ammonia and, more recently, amines, both of which are ubiquitous in the environment, have also been recognized as important contributors. However, accurately predicting new particle formation in both laboratory systems and in air has been problematic. During the oxidation of organosulfur compounds, gas-phase methanesulfonic acid is formed simultaneously with sulfuric acid, and both are found in particles in coastal regions as well as inland. We show here that: (i) Amines form particles on reaction with methanesulfonic acid, (ii) water vapor is required, and (iii) particle formation can be quantitatively reproduced by a semiempirical kinetics model supported by insights from quantum chemical calculations of likely intermediate clusters. Such an approach may be more broadly applicable in models of outdoor, indoor, and industrial settings where particles are formed, and where accurate modeling is essential for predicting their impact on health, visibility, and climate. PMID:23090988

  18. The Effect of Temperature and Acid Gas Loading on Corrosion Behavior of API 5L X52 Carbon Steel in Amine Unit

    NASA Astrophysics Data System (ADS)

    Javidi, M.; Lalehparvar, M. M.; Ghassemi, A.

    2016-05-01

    The effect of temperature and H2S concentration on amine corrosion of API 5L X52 carbon steel in a CO2-saturated 25 wt.% diethanolamine solution was investigated via electrochemical techniques. It was found that increase in temperature from 25 to 80 °C resulted in severe increase in corrosion rate from 0.88 to 16.24 mpy due to increase in degradation rate of amine. Also, it was concluded that increase in H2S concentration led to increase in corrosion rate because of formation of more heat stable amine salts. The effect of temperature on corrosion rate was more significant than acid gas loading.

  19. Hydrogen bonded supramolecular architectures of organic salts based on 5,7-dimethyl-1,8-naphthyridine-2-amine and acidic compounds

    NASA Astrophysics Data System (ADS)

    Jin, Shouwen; Zhang, Wenbiao; Liu, Li; Gao, Hongfang; Wang, Daqi; Chen, Rongpo; Xu, Xiaolei

    2010-06-01

    Studies concentrating on hydrogen bonding between the base of 5,7-dimethyl-1,8-naphthyridine-2-amine and acidic compounds have led to an increased understanding of the role 5,7-dimethyl-1,8-naphthyridine-2-amine has in binding with acidic compounds. Here anhydrous and hydrated multicomponent crystals of 5,7-dimethyl-1,8-naphthyridine-2-amine have been prepared with oxalic acid, 2,4,6-trinitrophenol, terephthalic acid, and phthalic acid. The four crystalline forms reported are organic salts of which the crystal structures have all been determined by X-ray diffraction. All products were formed in solution and obtained by the slow evaporation technique. The role of weak and strong hydrogen bonding in the crystal packing is ascertained.

  20. Phenylethynyl amine

    NASA Technical Reports Server (NTRS)

    Hergenrother, Paul M. (Inventor); Bryant, Robert G. (Inventor); Jensen, Brian J. (Inventor); Havens, Stephen J. (Inventor)

    1997-01-01

    Four phenylethynyl amine compounds--3 and 4-aminophenoxy-4'-phenylethynylbenzophenone, and 3 and 4-amino-4'-phenylethynylbenzophenone--were readily prepared and were used to endcap imide oligomers. Phenylethynyl-terminated amide acid oligomers and phenylethynyl-terminated imide oligomers with various molecular weights and compositions were prepared and characterized. These oligomers were cured at 300.degree. C. to 400.degree. C. to provide crosslinked polyimides with excellent solvent resistance, high strength and modulus and good high temperature properties. Adhesive panels, composites, films and moldings from these phenylethynyl terminated imide oligomers gave excellent mechanical performance.

  1. Evidence of acid-base interactions between amines and model indoor surfaces by ATR-FTIR spectroscopy

    NASA Astrophysics Data System (ADS)

    Destaillats, Hugo; Singer, Brett C.; Gundel, Lara A.

    Molecular associations of pyridine with cellulose and gypsum, surrogates for common indoor surface materials, were studied using an attenuated total reflection (ATR)-Fourier transform infrared (FTIR) spectrophotometric method. The purpose of this study was to gain insight into the molecular interactions of amines with well-characterized materials that affect their partitioning between indoor air and surfaces. The experimental results suggest the presence of at least two sorptive states for volatile and semivolatile amines, attributed to the chemisorbed species and to a more labile surface state (i.e., physisorbed pyridine). Both exhibited spectroscopic signatures corresponding to aromatic C-H stretching modes (2950-3100 cm -1) in the studied spectral region. Chemisorbed pyridine could be identified by the presence of additional IR signals in the N-H and O-H stretching region of the spectrum (2900-3600 cm -1). During desorption under a stream of N 2, surface enrichment in the chemisorbed species was evidenced by a slower reduction of the absorbance of the broad band at 2900-3600 cm -1 in relation to the total pyridine absorbance change. This spectroscopic evidence for acid-base interactions between amines and surfaces is consistent with the desorption behavior observed in previous work for nicotine from model surfaces.

  2. Eight salts constructed from 4-phenylthiazol-2-amine and carboxylic acid derivatives through combination of strong hydrogen bonding and weak noncovalent interactions

    NASA Astrophysics Data System (ADS)

    Jin, Shouwen; Zhu, Qiaowang; Wei, ShuaiShuai; Wang, Daqi

    2013-10-01

    Eight crystalline organic salts derived from 4-phenylthiazol-2-amine and carboxylic acid derivatives (2-chloronicotinic acid, 3-hydroxy-2-naphthoic acid, p-nitrobenzoic acid, 2-hydroxy-5-(phenyldiazenyl)benzoic acid, 5-nitrosalicylic acid, 5-sulfosalicylic acid, oxalic acid, and L-malic acid) were prepared and characterized by X-ray diffraction analysis, IR, mp, and elemental analysis. In all of the salts except 6, 7, and 8, the 4-phenylthiazol-2-amine and carboxylic acid components are held together by two fused heterosynthons: a R22(7) heterosynthon and a R22(8) heterosynthon. All supramolecular architectures of the organic salts 1-8 involve extensive Nsbnd H⋯O hydrogen bonds as well as other noncovalent interactions. The role of weak and strong noncovalent interactions in the crystal packing is ascertained. The salts displayed 2D/3D framework structure under these weak interactions.

  3. Biogenic gold nanoparticles as fotillas to fire berberine hydrochloride using folic acid as molecular road map.

    PubMed

    Pandey, Sunil; Mewada, Ashmi; Thakur, Mukeshchand; Shah, Ritu; Oza, Goldie; Sharon, Madhuri

    2013-10-01

    Use of biologically modified gold nanoparticles (GNPs) as molecular vehicle to ferry potential anti-cancer drug berberine hydrochloride (BHC) using folic acid (FA) as targeting molecule is reported in this work. A tropical fruit peel, Trapa bispinosa is used to fabricate highly monodispersed GNPs, passivated with essential functional groups which were used as linkers to attach FA and BHC via amide linkage. Flocculation Parameter (FP) of biologically synthesized GNPs was calculated under different salt concentrations which were found to be very ideal under a physiological condition. Various statistical models were used to find drug release profile out of which Higuchi was found to be the most ideal. GNP-FA-BHC complexes were found to be active against folic acid expressing HeLa cells.

  4. Novel Regenerated Solvent Extraction Processes for the Recovery of Carboxylic Acids or Ammonia from Aqueous Solutions Part I. Regeneration of Amine-Carboxylic Acid Extracts

    SciTech Connect

    Poole, L.J.; King, C.J.

    1990-03-01

    Two novel regenerated solvent extraction processes are examined. The first process has the potential to reduce the energy costs inherent in the recovery of low-volatility carboxylic acids from dilute aqueous solutions. The second process has the potential for reducing the energy costs required for separate recovery of ammonia and acid gases (e.g. CO{sub 2} and H{sub 2}S) from industrial sour waters. The recovery of carboxylic acids from dilute aqueous solution can be achieved by extraction with tertiary amines. An approach for regeneration and product recovery from such extracts is to back-extract the carboxylic acid with a water-soluble, volatile tertiary amine, such as trimethylamine. The resulting trimethylammonium carboxylate solution can be concentrated and thermally decomposed, yielding the product acid and the volatile amine for recycle. Experimental work was performed with lactic acid, succinic acid, and fumaric acid. Equilibrium data show near-stoichiometric recovery of the carboxylic acids from an organic solution of Alamine 336 into aqueous solutions of trimethylamine. For fumaric and succinic acids, partial evaporation of the aqueous back extract decomposes the carboxylate and yields the acid product in crystalline form. The decomposition of aqueous solutions of trimethylammonium lactates was not carried out to completion, due to the high water solubility of lactic acid and the tendency of the acid to self-associate. The separate recovery of ammonia and acid gases from sour waters can be achieved by combining steam-stripping of the acid gases with simultaneous removal of ammonia by extraction with a liquid cation exchanger. The use of di-2,4,4-trimethylpentyl phosphinic acid as the liquid cation exchanger is explored in this work. Batch extraction experiments were carried out to measure the equilibrium distribution ratio of ammonia between an aqueous buffer solution and an organic solution of the phosphinic acid (0.2N) in Norpar 12. The concentration

  5. Protection of originality of Tokaji Aszú: amines and organic acids in botrytized wines by high-performance liquid chromatography.

    PubMed

    Kiss, Judit; Sass-Kiss, Agnes

    2005-12-28

    Amine and organic acid composition of Aszú wines from the Tokaj region of Hungary, nonbotrytized Hungarian wines from different regions, and foreign botrytized wines were analyzed by high-performance liquid chromatography. Hungarian and foreign wines (36 Hungarian and seven foreign botrytized wines) were compared in different ways by calculation of ratios of given amine compounds, analyses of variance, principal component, and discriminant analysis. In wines, putrescine and in some samples 3-methyl-butylamine and/or phenyl ethylamine were found in remarkable concentrations, while in botrytized wines four other amines were verified in high concentration. Good separation between Aszú and foreign botrytized wines was found by calculation of the amine component's ratio. The first two principal components of the principal component analysis accounted for 77 and 84% of the total variance in the data of amines and acids, respectively. The component scores of samples grouped according to Aszú, foreign botrytized, and nonbotrytized wines. Linear discriminant analysis was used for differentiation of Aszú, foreign botrytized, and normal wines. Using nine amines and two acids as variables, the correct classification was 97.6%. On the basis of results, an objective evaluation method can be elaborated for quality control in order to protect the authenticity and origin of wine specialties made from botrytized grapes.

  6. Systematic evaluation and optimization of modification reactions of oligonucleotides with amines and carboxylic acids for the synthesis of DNA-encoded chemical libraries.

    PubMed

    Franzini, Raphael M; Samain, Florent; Abd Elrahman, Maaly; Mikutis, Gediminas; Nauer, Angela; Zimmermann, Mauro; Scheuermann, Jörg; Hall, Jonathan; Neri, Dario

    2014-08-20

    DNA-encoded chemical libraries are collections of small molecules, attached to DNA fragments serving as identification barcodes, which can be screened against multiple protein targets, thus facilitating the drug discovery process. The preparation of large DNA-encoded chemical libraries crucially depends on the availability of robust synthetic methods, which enable the efficient conjugation to oligonucleotides of structurally diverse building blocks, sharing a common reactive group. Reactions of DNA derivatives with amines and/or carboxylic acids are particularly attractive for the synthesis of encoded libraries, in view of the very large number of building blocks that are commercially available. However, systematic studies on these reactions in the presence of DNA have not been reported so far. We first investigated conditions for the coupling of primary amines to oligonucleotides, using either a nucleophilic attack on chloroacetamide derivatives or a reductive amination on aldehyde-modified DNA. While both methods could be used for the production of secondary amines, the reductive amination approach was generally associated with higher yields and better purity. In a second endeavor, we optimized conditions for the coupling of a diverse set of 501 carboxylic acids to DNA derivatives, carrying primary and secondary amine functions. The coupling efficiency was generally higher for primary amines, compared to secondary amine substituents, but varied considerably depending on the structure of the acids and on the synthetic methods used. Optimal reaction conditions could be found for certain sets of compounds (with conversions >80%), but multiple reaction schemes are needed when assembling large libraries with highly diverse building blocks. The reactions and experimental conditions presented in this article should facilitate the synthesis of future DNA-encoded chemical libraries, while outlining the synthetic challenges that remain to be overcome.

  7. Separate recovery of copper and zinc from acid mine drainage using biogenic sulfide.

    PubMed

    Sahinkaya, Erkan; Gungor, Murat; Bayrakdar, Alper; Yucesoy, Zeynep; Uyanik, Sinan

    2009-11-15

    Precipitation of metals from acid mine drainage (AMD) using sulfide gives the possibility of selective recovery due to different solubility product of each metal. Using sulfate reducing bacteria to produce sulfide for that purpose is advantageous due to in situ and on-demand sulfide production. In this study, separate precipitation of Cu and Zn was studied using sulfide produced in anaerobic baffled reactor (ABR). ABR fed with ethanol (1340 mg/L chemical oxygen demand (COD)) and sulfate (2000 mg/L) gave a stable performance with 65% sulfate reduction, 85% COD removal and around 320 mg/L sulfide production. Cu was separately precipitated at low pH (pH<2) using sulfide transported from ABR effluent via N(2) gas. Cu precipitation was complete within 45-60 min and Zn did not precipitate during Cu removal. The Cu precipitation rate increased with initial Cu concentration. After selective Cu precipitation, Zn recovery was studied using ABR effluent containing sulfide and alkalinity. Depending on initial sulfide/Zn ratio, removal efficiency varied between 84 and 98%. The low pH of Zn bearing AMD was also increased to neutral values using alkalinity produced by sulfate reducing bacteria in ABR. The mode of particle size distribution of ZnS and CuS precipitates was around 17 and 46 microm, respectively.

  8. Hydrogen-deuterium exchange of aromatic amines and amides using deuterated trifluoroacetic acid

    PubMed Central

    Giles, Richard; Lee, Amy; Jung, Erica; Kang, Aaron; Jung, Kyung Woon

    2014-01-01

    The H-D exchange of aromatic amines and amides, including pharmaceutically relevant compounds such as acetaminophen and diclofenac, was investigated using CF3COOD as both the sole reaction solvent and source of deuterium label. The described method is amenable to efficient deuterium incorporation for a wide variety of substrates possessing both electron-donating and electron-withdrawing substituents. Best results were seen with less basic anilines and highly activated acetanilides, reflecting the likelihood of different mechanistic pathways. PMID:25641994

  9. Amine derivatives of thio-bis-lactone acids in combination with coadditive hydrocarbons are flow improvers for middle distillate fuel oils

    SciTech Connect

    Brois, S.J.; Feldman, N.; Gutierrez, A.

    1981-02-17

    Amine salts, amino acids, amino acid salts bis-amides and imides of oil-soluble thio-bis-(C12-50 alkyl lactone acid), e.g. a secondary hydrogenated tallow amide of dithio-bis-(C16-c24 alkyl lactone carboxylic acid), are useful in combination with a coadditive hydrocarbon such as an amorphous hydrocarbon or a hydrogenated polybutadiene in improving the cold flow properties of distillate hydrocarbon oils.

  10. Determination of acid dissociation constant of 20 coumarin derivatives by capillary electrophoresis using the amine capillary and two different methodologies.

    PubMed

    Nowak, Paweł Mateusz; Woźniakiewicz, Michał; Piwowarska, Monika; Kościelniak, Paweł

    2016-05-13

    In this work capillary electrophoresis has been used to determine acid dissociation constant of 20 structurally diverse coumarin derivatives. For a majority of compounds pKa value has been determined for the first time. The obtained values vary between 4.16-9.10pH unit, pointing to the interesting structure-acidity relationships. The amine permanently coated capillary has been applied for that purpose, because it has turned out to be more effective in pKa determination than the bare silica and other coated capillaries, ensuring good precision and shorter migration times. A traditional methodology relying on measurements in a broad pH range and fitting of a sigmoidal function has been compared to an alternative simplified approach, reported for the first time, where only two electrophoretic mobility values suffice for pKa estimation. The first value corresponds to the partially ionized form and it is measured experimentally, while the second one to the totally ionized form - it is measured experimentally (two-values method) or estimated directly from molecular mass (one-value method). We show that despite a limited measurements number, the alternative approach may be consistent with the traditional methodology, yielding the relatively low pKa deviation. Its reliability has also been confirmed by the analytical predictions, comprising resolution, migration order, migration times and peaks overlapping. Therefore, combination of the amine capillary with the simplified calculation method is an attractive tool for fast and reliable pKa estimation.

  11. Carbonic anhydrase activators: Activation of the β-carbonic anhydrase from Malassezia globosa with amines and amino acids.

    PubMed

    Vullo, Daniela; Del Prete, Sonia; Capasso, Clemente; Supuran, Claudiu T

    2016-03-01

    The β-carbonic anhydrase (CA, EC 4.2.1.1) from the dandruff producing fungus Malassezia globosa, MgCA, was investigated for its activation with amines and amino acids. MgCA was weakly activated by amino acids such as L-/D-His, L-Phe, D-DOPA, D-Trp, L-/D-Tyr and by the amine serotonin (KAs of 12.5-29.3μM) but more effectively activated by d-Phe, l-DOPA, l-Trp, histamine, dopamine, pyridyl-alkylamines, and 4-(2-aminoethyl)-morpholine, with KAs of 5.82-10.9μM. The best activators were l-adrenaline and 1-(2-aminoethyl)piperazine, with activation constants of 0.72-0.81μM. This study may help a better understanding of the activation mechanisms of β-CAs from pathogenic fungi as well as the design of tighter binding ligands for this enzyme which is a drug target for novel types of anti-dandruff agents.

  12. Carbonic anhydrase activators: Activation of the β-carbonic anhydrase from Malassezia globosa with amines and amino acids.

    PubMed

    Vullo, Daniela; Del Prete, Sonia; Capasso, Clemente; Supuran, Claudiu T

    2016-03-01

    The β-carbonic anhydrase (CA, EC 4.2.1.1) from the dandruff producing fungus Malassezia globosa, MgCA, was investigated for its activation with amines and amino acids. MgCA was weakly activated by amino acids such as L-/D-His, L-Phe, D-DOPA, D-Trp, L-/D-Tyr and by the amine serotonin (KAs of 12.5-29.3μM) but more effectively activated by d-Phe, l-DOPA, l-Trp, histamine, dopamine, pyridyl-alkylamines, and 4-(2-aminoethyl)-morpholine, with KAs of 5.82-10.9μM. The best activators were l-adrenaline and 1-(2-aminoethyl)piperazine, with activation constants of 0.72-0.81μM. This study may help a better understanding of the activation mechanisms of β-CAs from pathogenic fungi as well as the design of tighter binding ligands for this enzyme which is a drug target for novel types of anti-dandruff agents. PMID:26856923

  13. Hygroscopicity of Amine Secondary Aerosol - Mixtures of Organic and Inorganic Components

    NASA Astrophysics Data System (ADS)

    Tang, X.; Cocker, D. R.; Purvis-Roberts, K.; Asa-Awuku, A. A.

    2012-12-01

    Aliphatic amines are emitted from both biogenic and anthropogenic sources and contribute to the formation of secondary aerosol in reactions with atmospheric radicals. However, the cloud condensation nuclei (CCN) ability of amine aerosol has not been explored yet. Here, we study the hygroscopicity of aerosol formed from three aliphatic amines (trimethylamine, diethylamine and butylamine) in the UCR environmental chamber. Amines can react with NO3, a dominant night time oxidant in acid-base and/or oxidation reactions. The mass fraction of organic and inorganic components of formed aerosol was measured by Particle-into-Liquid Sampler coupled to dual ion chromatographs (PILS-ICs) and Scanning Mobility Particle Sizer (SMPS). CCN counter was used to measure the water-uptake ability of these particles. Significantly high hygroscopicity (κ>0.3) was observed for aerosols formed from diethylamine and butylamine with NO3 radicals, which comprised >40% inorganic salt. Compared with amines oxidized by hydroxyl radicals, the presence of aminium salts formed in acid-base reactions greatly improved CCN activity of NO3-initiated aerosol. The effect of water vapor on the formation of aminium salts and aerosol hygroscopicity was also studied. Our results will significantly impact the estimation and role of amines in atmospheric chemistry and global climate models.

  14. Ice core sulfur and methanesulfonic acid (MSA) records from southern Greenland document North American and European air pollution and suggest a decline in regional biogenic sulfur emissions.

    NASA Astrophysics Data System (ADS)

    Pasteris, D. R.; McConnell, J. R.; Burkhart, J. F.; Saltzman, E. S.

    2014-12-01

    Sulfate aerosols have an important cooling effect on the Earth because they scatter sunlight back to space and form cloud condensation nuclei. However, understanding of the atmospheric sulfur cycle is incomplete, leading to uncertainty in the assessment of past, present and future climate forcing. Here we use annually resolved observations of sulfur and methanesulfonic acid (MSA) concentration in an array of precisely dated Southern Greenland ice cores to assess the history of sulfur pollution emitted from North America and Europe and the history of biogenic sulfate aerosol derived from the North Atlantic Ocean over the last 250 years. The ice core sulfur time series is found to closely track sulfur concentrations in North American and European precipitation since records began in 1965, and also closely tracks estimated sulfur emissions since 1850 within the air mass source region as determined by back trajectory analysis. However, a decline to near-preindustrial sulfur concentrations in the ice cores after 1995 that is not so extensive in the source region emissions indicates that there has been a change in sulfur cycling over the last 150 years. The ice core MSA time series shows a decline of 60% since the 1860s, and is well correlated with declining sea ice concentrations around Greenland, suggesting that the phytoplankton source of biogenic sulfur has declined due to a loss of marginal sea ice zone habitat. Incorporating the implied decrease in biogenic sulfur in our analysis improves the match between the ice core sulfur record and the source region emissions throughout the last 150 years, and solves the problem of the recent return to near-preindustrial levels in the Greenland ice. These findings indicate that the transport efficiency of sulfur air pollution has been relatively stable through the industrial era and that biogenic sulfur emissions in the region have declined.

  15. Corrosion inhibition of aminated hydroxyl ethyl cellulose on mild steel in acidic condition.

    PubMed

    Sangeetha, Y; Meenakshi, S; Sairam Sundaram, C

    2016-10-01

    Aminated hydroxyethyl cellulose (AHEC) was synthesized, characterized using Fourier Transform Infrared spectroscopy (FTIR) and the corrosion inhibition of AHEC on mild steel in 1M HCl was studied using chemical and electrochemical studies. Results obtained in weight loss method showed that inhibition efficiency increased with increase in concentration of AHEC. The adsorption of the inhibitor on metal surface followed Frumkin isotherm. Polarization studies revealed that the AHEC inhibits through mixed mode. Thermodynamic parameters and activation energy were calculated and discussed. FTIR and X-ray diffraction studies (XRD) confirmed the adsorption of the inhibitor. The surface morphology was studied using Scanning Electron Microscope (SEM) and Atomic Force Microscopy (AFM).

  16. Corrosion inhibition of aminated hydroxyl ethyl cellulose on mild steel in acidic condition.

    PubMed

    Sangeetha, Y; Meenakshi, S; Sairam Sundaram, C

    2016-10-01

    Aminated hydroxyethyl cellulose (AHEC) was synthesized, characterized using Fourier Transform Infrared spectroscopy (FTIR) and the corrosion inhibition of AHEC on mild steel in 1M HCl was studied using chemical and electrochemical studies. Results obtained in weight loss method showed that inhibition efficiency increased with increase in concentration of AHEC. The adsorption of the inhibitor on metal surface followed Frumkin isotherm. Polarization studies revealed that the AHEC inhibits through mixed mode. Thermodynamic parameters and activation energy were calculated and discussed. FTIR and X-ray diffraction studies (XRD) confirmed the adsorption of the inhibitor. The surface morphology was studied using Scanning Electron Microscope (SEM) and Atomic Force Microscopy (AFM). PMID:27312608

  17. The mechanism of action of dipeptidyl aminopeptidase. Inhibition by amino acid derivatives and amines; activation by aromatic compounds.

    PubMed

    Metrione, R M; MacGeorge, N L

    1975-12-01

    A variety of amino acid and peptide amides have been shown to be inhibitors of dipeptidyl aminopeptidase. Among these compounds derivatives of strongly hydrophobic amino acids are the strongest inhibitors (Phe-NH2, Ki = 1.0 +/- 0.2 mM), while amides of basic amino acids were somewhat less effective (Lys-NH2, Ki = 36 +/- 3 mM). Short chain amino acid amides are notably weaker inhibitors (Gly-NH2, Ki = 293 +/- 50 mM). The interaction of the side chains of compounds with the enzyme appears to be at a site other than that at which the side chain of the amino-penultimate residue of the substrate interacts since the specificity of binding is different. Primary amines have been shown to inhibit, e.g., butylamine, Ki = 340 +/- 40 mM, and aromatic compounds have been shown to stimulate activity toward Gly-Gly-NH2 and Gly-Gly-OEt (phenol, 35% stimulation of activity at a 1:1 molar ratio with the substrate). The data suggest that inhibition involves binding at the site occupied by the free alpha-amino group and the N-terminal amino acid.

  18. Pharmacological potential of biogenic amine–polyamine interactions beyond neurotransmission

    PubMed Central

    Sánchez-Jiménez, F; Ruiz-Pérez, M V; Urdiales, J L; Medina, M A

    2013-01-01

    Histamine, serotonin and dopamine are biogenic amines involved in intercellular communication with multiple effects on human pathophysiology. They are products of two highly homologous enzymes, histidine decarboxylase and l-aromatic amino acid decarboxylase, and transmit their signals through different receptors and signal transduction mechanisms. Polyamines derived from ornithine (putrescine, spermidine and spermine) are mainly involved in intracellular effects related to cell proliferation and death mechanisms. This review summarizes structural and functional evidence for interactions between components of all these amine metabolic and signalling networks (decarboxylases, transporters, oxidases, receptors etc.) at cellular and tissue levels, distinct from nervous and neuroendocrine systems, where the crosstalk among these amine-related components can also have important pathophysiological consequences. The discussion highlights aspects that could help to predict and discuss the effects of intervention strategies. Linked Articles This article is part of a themed issue on Histamine Pharmacology Update. To view the other articles in this issue visit http://dx.doi.org/10.1111/bph.2013.170.issue-1 PMID:23347064

  19. One-pot assembly of metal/organic-acid sites on amine-functionalized ligands of MOFs for photocatalytic hydrogen peroxide splitting.

    PubMed

    Qin, Lei; Li, Zhaowen; Hu, Qiong; Xu, Zehai; Guo, Xinwen; Zhang, Guoliang

    2016-06-01

    A one-pot organic-acid-directed post-synthetic modification allows molecular iron/citric acid complexes to be anchored into amine-functionalized MOFs by a simple and rapid liquid spraying method. Amidation between organic acid and -NH2 groups of ligands can lead to more small nanoparticles (NPs) that are well-dispersed into MOFs and exhibit high activity for photocatalytic H2O2 splitting. PMID:27166081

  20. Application of a surface plasmon resonance sensor to analyses of amine compounds with the use of a polymer film and an acid-base reaction.

    PubMed

    Nishimura, Satoshi; Yoshidome, Toshifumi; Tokuda, Tomoyuki; Mitsushio, Masaru; Higo, Morihide

    2002-03-01

    A surface plasmon resonance (SPR) sensor was applied to analyses of some amine compounds (n-butylamine, isobutylamine, aniline, and N,N-dimethylaniline) by using a polymer film and an acid-base reaction in it. Poly(acrylamide) (PAA) was adopted as the polymer film and was immobilized on an Au film to prepare a sensor chip. Pivalic acid was entered into the PAA film as an acid. The PAA film with a thickness of 50 nm gave the highest sensitivity to the SPR sensor. Although water was better concerning the sensitivity for the SPR sensor as the solvent, ethanol was adopted because it dissolves well all of the amine compounds used. The Au film coated with the PAA film gave higher sensitivity for analyses of n-butylamine and isobutylamine, and lower sensitivity for analyses of aniline and N,N-dimethylaniline than an Au film without the PAA film. The PAA film containing pivalic acid gave 4-5 orders of magnitude higher sensitivity to the SPR sensor for analyses of all the amine compounds due to the reaction between pivalic acid and these amine compounds.

  1. The effect of aromatic amines and phenols in the thiyl-induced reactions of polyunsaturated fatty acids

    NASA Astrophysics Data System (ADS)

    Tartaro Bujak, Ivana; Chatgilialoglu, Chryssostomos; Ferreri, Carla; Valgimigli, Luca; Amorati, Riccardo; Mihaljević, Branka

    2016-07-01

    Thiols are well known for their role in cellular redox homeostasis, while aromatic amines and phenols are the best known classes of chain-breaking antioxidants. On the other hand, thiyl radicals are known to catalyse the double bond isomerization in PUFA. We investigated the role and interplay of 2-mercaptoethanol and diphenylamine in the parallel processes of peroxidation and cis-trans isomerization of linoleic acid (LA) during gamma radiolysis, both in solution and micelles. Both compounds, used alone were able to protect LA from oxidation; however pro-oxidant activity and enhanced isomerization was observed when they were used together, depending on the experimental settings. Instead, α-tocopherol protected LA from both oxidation and isomerization in the presence of thiols under any tested settings. The mechanistic scenario is discussed highlighting the role of diphenylaminyl radicals in promoting thiyl-radical-induced cis-trans isomerization in the presence of oxygen.

  2. Phosphotungstic acid encapsulated in the mesocages of amine-functionalized metal-organic frameworks for catalytic oxidative desulfurization.

    PubMed

    Wang, Xu-Sheng; Huang, Yuan-Biao; Lin, Zu-Jin; Cao, Rong

    2014-08-21

    Highly dispersed Keggin-type phosphotungstic acid (H3PW12O40, PTA) encapsulated in the mesocages of amine-functionalized metal-organic frameworks MIL-101(Cr)-NH2 has been prepared by an anion-exchange method. PTA anions (PW12O40(3-)) are stabilized in the mesocages via the electrostatic interaction with amino groups of the MIL-101(Cr)-NH2. The obtained catalyst (denoted PTA@MIL-101(Cr)-NH2) exhibits high catalytic activity in the extractive and catalytic oxidative desulfurization (ECODS) system under mild conditions. Moreover, it can be easily recovered and recycled several times without leaching and loss of activity. PMID:24967570

  3. Poly(2 deoxy 2 methacrylamido glucopyranose) b Poly(methacrylate amine)s: Optimization of Diblock Glycopol ycations for Nucleic Acid Delivery

    PubMed Central

    Li, Haibo; Cortez, Mallory A.; Phillips, Haley R.; Wu, Yaoying; Reineke, Theresa M.

    2013-01-01

    A series of nine poly(2-deoxy-2-methacrylamido glucopyranose)-b-poly(methacrylate amine) diblock copolycations The cationic block was varied in length and in the degree of methyl group substitution (secondary, tertiary, quaternary) on the pendant amine in an effort to optimize the structure and activity for plasmid DNA delivery. Upon a thorough kinetic study of polymerization for each polymer, the glycopolymers were prepared with well-controlled Mn and Ð. The binding and colloidal stability of the polymer-pDNA nanocomplexes at different N/P ratios and in biological media has been investigated using gel electrophoresis and light scattering techniques. The toxicity and transfection efficiency of the polyplexes has been evaluated with Hep G2 (human liver hepatocellular carcinoma) cells; several polymers displayed excellent delivery and toxicity profiles justifying their further development for in vivo gene therapy. PMID:24179703

  4. Poly(2 deoxy 2 methacrylamido glucopyranose) b Poly(methacrylate amine)s: Optimization of Diblock Glycopol ycations for Nucleic Acid Delivery.

    PubMed

    Li, Haibo; Cortez, Mallory A; Phillips, Haley R; Wu, Yaoying; Reineke, Theresa M

    2013-03-19

    A series of nine poly(2-deoxy-2-methacrylamido glucopyranose)-b-poly(methacrylate amine) diblock copolycations The cationic block was varied in length and in the degree of methyl group substitution (secondary, tertiary, quaternary) on the pendant amine in an effort to optimize the structure and activity for plasmid DNA delivery. Upon a thorough kinetic study of polymerization for each polymer, the glycopolymers were prepared with well-controlled Mn and Ð. The binding and colloidal stability of the polymer-pDNA nanocomplexes at different N/P ratios and in biological media has been investigated using gel electrophoresis and light scattering techniques. The toxicity and transfection efficiency of the polyplexes has been evaluated with Hep G2 (human liver hepatocellular carcinoma) cells; several polymers displayed excellent delivery and toxicity profiles justifying their further development for in vivo gene therapy. PMID:24179703

  5. Atom-economic catalytic amide synthesis from amines and carboxylic acids activated in situ with acetylenes

    PubMed Central

    Krause, Thilo; Baader, Sabrina; Erb, Benjamin; Gooßen, Lukas J.

    2016-01-01

    Amide bond-forming reactions are of tremendous significance in synthetic chemistry. Methodological research has, in the past, focused on efficiency and selectivity, and these have reached impressive levels. However, the unacceptable amounts of waste produced have led the ACS GCI Roundtable to label ‘amide bond formation avoiding poor atom economy' as the most pressing target for sustainable synthetic method development. In response to this acute demand, we herein disclose an efficient one-pot amide coupling protocol that is based on simple alkynes as coupling reagents: in the presence of a dichloro[(2,6,10-dodecatriene)-1,12-diyl]ruthenium catalyst, carboxylate salts of primary or secondary amines react with acetylene or ethoxyacetylene to vinyl ester intermediates, which undergo aminolysis to give the corresponding amides along only with volatile acetaldehyde or ethyl acetate, respectively. The new amide synthesis is broadly applicable to the synthesis of structurally diverse amides, including dipeptides. PMID:27282773

  6. Atom-economic catalytic amide synthesis from amines and carboxylic acids activated in situ with acetylenes.

    PubMed

    Krause, Thilo; Baader, Sabrina; Erb, Benjamin; Gooßen, Lukas J

    2016-01-01

    Amide bond-forming reactions are of tremendous significance in synthetic chemistry. Methodological research has, in the past, focused on efficiency and selectivity, and these have reached impressive levels. However, the unacceptable amounts of waste produced have led the ACS GCI Roundtable to label 'amide bond formation avoiding poor atom economy' as the most pressing target for sustainable synthetic method development. In response to this acute demand, we herein disclose an efficient one-pot amide coupling protocol that is based on simple alkynes as coupling reagents: in the presence of a dichloro[(2,6,10-dodecatriene)-1,12-diyl]ruthenium catalyst, carboxylate salts of primary or secondary amines react with acetylene or ethoxyacetylene to vinyl ester intermediates, which undergo aminolysis to give the corresponding amides along only with volatile acetaldehyde or ethyl acetate, respectively. The new amide synthesis is broadly applicable to the synthesis of structurally diverse amides, including dipeptides. PMID:27282773

  7. Synthetic Studies on Tricyclic Diterpenoids: Direct Allylic Amination Reaction of Isopimaric Acid Derivatives.

    PubMed

    Timoshenko, Mariya A; Kharitonov, Yurii V; Shakirov, Makhmut M; Bagryanskaya, Irina Yu; Shults, Elvira E

    2016-02-01

    A selective synthesis of 7- or 14-nitrogen containing tricyclic diterpenoids was completed according to a strategy in which the key step was the catalyzed direct allylic amination of methyl 14α-hydroxy-15,16-dihydroisopimarate with a wide variety of nitrogenated nucleophiles. It was revealed that the selectivity of the reaction depends on the nature of nucleophile. The catalyzed reaction of the mentioned diterpenoid allylic alcohol with 3-nitroaniline, 3-(trifluoromethyl)aniline, and 4-(trifluoromethyl)aniline yield the subsequent 7α-, 7β- and 14αnitrogen-containing diterpenoids. The reaction with 2-nitroaniline, 4-nitro-2-chloroaniline, 4-methoxy-2-nitroaniline, phenylsulfamide, or tert-butyl carbamate proceeds with the formation of 7α-nitrogen-substituted diterpenoids as the main products. PMID:27308214

  8. 40 CFR 721.9595 - Alkyl benzene sulfonic acids and alkyl sulfates, amine salts (generic).

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Alkyl benzene sulfonic acids and alkyl... Significant New Uses for Specific Chemical Substances § 721.9595 Alkyl benzene sulfonic acids and alkyl...) The chemical substances identified generically as alkyl benzene sulfonic acids and alkyl...

  9. 40 CFR 721.9595 - Alkyl benzene sulfonic acids and alkyl sulfates, amine salts (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Alkyl benzene sulfonic acids and alkyl... Significant New Uses for Specific Chemical Substances § 721.9595 Alkyl benzene sulfonic acids and alkyl...) The chemical substances identified generically as alkyl benzene sulfonic acids and alkyl...

  10. 40 CFR 721.9595 - Alkyl benzene sulfonic acids and alkyl sulfates, amine salts (generic).

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Alkyl benzene sulfonic acids and alkyl... Significant New Uses for Specific Chemical Substances § 721.9595 Alkyl benzene sulfonic acids and alkyl...) The chemical substances identified generically as alkyl benzene sulfonic acids and alkyl...

  11. 40 CFR 721.9595 - Alkyl benzene sulfonic acids and alkyl sulfates, amine salts (generic).

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Alkyl benzene sulfonic acids and alkyl... Significant New Uses for Specific Chemical Substances § 721.9595 Alkyl benzene sulfonic acids and alkyl...) The chemical substances identified generically as alkyl benzene sulfonic acids and alkyl...

  12. 40 CFR 721.9595 - Alkyl benzene sulfonic acids and alkyl sulfates, amine salts (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Alkyl benzene sulfonic acids and alkyl... Significant New Uses for Specific Chemical Substances § 721.9595 Alkyl benzene sulfonic acids and alkyl...) The chemical substances identified generically as alkyl benzene sulfonic acids and alkyl...

  13. Observation of new particle formation and measurement of sulfuric acid, ammonia, amines and highly oxidized organic molecules at a rural site in central Germany

    NASA Astrophysics Data System (ADS)

    Kürten, Andreas; Bergen, Anton; Heinritzi, Martin; Leiminger, Markus; Lorenz, Verena; Piel, Felix; Simon, Mario; Sitals, Robert; Wagner, Andrea C.; Curtius, Joachim

    2016-10-01

    The exact mechanisms for new particle formation (NPF) under different boundary layer conditions are not known yet. One important question is whether amines and sulfuric acid lead to efficient NPF in the atmosphere. Furthermore, it is not clear to what extent highly oxidized organic molecules (HOMs) are involved in NPF. We conducted field measurements at a rural site in central Germany in the proximity of three larger dairy farms to investigate whether there is a connection between NPF and the presence of amines and/or ammonia due to the local emissions from the farms. Comprehensive measurements using a nitrate chemical ionization-atmospheric pressure interface time-of-flight (CI-APi-TOF) mass spectrometer, a proton-transfer-reaction mass spectrometer (PTR-MS), particle counters and differential mobility analyzers (DMAs), as well as measurements of trace gases and meteorological parameters, were performed. We demonstrate here that the nitrate CI-APi-TOF is suitable for sensitive measurements of sulfuric acid, amines, a nitrosamine, ammonia, iodic acid and HOMs. NPF was found to correlate with sulfuric acid, while an anti-correlation with RH, amines and ammonia is observed. The anti-correlation between NPF and amines could be due to the efficient uptake of these compounds by nucleating clusters and small particles. Much higher HOM dimer (C19/C20 compounds) concentrations during the night than during the day indicate that these HOMs do not efficiently self-nucleate as no nighttime NPF is observed. Observed iodic acid probably originates from an iodine-containing reservoir substance, but the iodine signals are very likely too low to have a significant effect on NPF.

  14. Atmospheric amines - Part I. A review

    NASA Astrophysics Data System (ADS)

    Ge, Xinlei; Wexler, Anthony S.; Clegg, Simon L.

    2011-01-01

    Amines are emitted by a wide range of sources and are ubiquitous atmospheric organic bases. Approximately 150 amines and about 30 amino acids have been identified in the atmosphere. We review the present knowledge of atmospherically relevant amines with respect to their sources, fluxes, and dynamics including gas-phase reactions, gas-to-particle conversion and deposition. The health effects of aliphatic and aromatic amines are briefly summarized as well as the atmospheric occurrence and reactivity of amino acids and urea.

  15. Peptidyl prolyl isomerase Pin1-inhibitory activity of D-glutamic and D-aspartic acid derivatives bearing a cyclic aliphatic amine moiety.

    PubMed

    Nakagawa, Hidehiko; Seike, Suguru; Sugimoto, Masatoshi; Ieda, Naoya; Kawaguchi, Mitsuyasu; Suzuki, Takayoshi; Miyata, Naoki

    2015-12-01

    Pin1 is a peptidyl prolyl isomerase that specifically catalyzes cis-trans isomerization of phosphorylated Thr/Ser-Pro peptide bonds in substrate proteins and peptides. Pin1 is involved in many important cellular processes, including cancer progression, so it is a potential target of cancer therapy. We designed and synthesized a novel series of Pin1 inhibitors based on a glutamic acid or aspartic acid scaffold bearing an aromatic moiety to provide a hydrophobic surface and a cyclic aliphatic amine moiety with affinity for the proline-binding site of Pin1. Glutamic acid derivatives bearing cycloalkylamino and phenylthiazole groups showed potent Pin1-inhibitory activity comparable with that of known inhibitor VER-1. The results indicate that steric interaction of the cyclic alkyl amine moiety with binding site residues plays a key role in enhancing Pin1-inhibitory activity.

  16. Palladium-catalyzed C–N and C–O bond formation of N-substituted 4-bromo-7-azaindoles with amides, amines, amino acid esters and phenols

    PubMed Central

    Surasani, Rajendra; Rao, A V Dhanunjaya; Chandrasekhar, K B

    2012-01-01

    Summary Simple and efficient procedures for palladium-catalyzed cross-coupling reactions of N-substituted 4-bromo-7-azaindole (1H-pyrrole[2,3-b]pyridine), with amides, amines, amino acid esters and phenols through C–N and C–O bond formation have been developed. The C–N cross-coupling reaction of amides, amines and amino acid esters takes place rapidly by using the combination of Xantphos, Cs2CO3, dioxane and palladium catalyst precursors Pd(OAc)2/Pd2(dba)3. The combination of Pd(OAc)2, Xantphos, K2CO3 and dioxane was found to be crucial for the C–O cross-coupling reaction. This is the first report on coupling of amides, amino acid esters and phenols with N-protected 4-bromo-7-azaindole derivatives. PMID:23209536

  17. Synthesis, Structural Characterization and Biological Activity of Peroxo Complexes of Zirconium (IV) Containing Organic Acid and Amine Bases

    NASA Astrophysics Data System (ADS)

    Nasrin, Jahanara; Saidul Islam, M.

    The study was extended to isolate the peroxo complexes of Zr (IV) containing organic acid and amine bases. The Zr (IV) complexes have been found to oxidize allyl alcohol and triphenylphosphine as well as triphenylarsine to their respective oxides. The analytical data are in good agreement with the proposed empirical formulae of the present complexes. The complexes display v(C = O) bands at ~1630 cm-1 and v(C-O) bands at ~1412 cm-1 significantly lower than the values of amino acid (~1650 and ~1450 cm-1). These indicate the coordination of amino acid through their carboxylate anion. The broad band observed at about 3217-3350 cm-1 for v (N-H) modes indicate the coordination of amino group through nitrogen atom of amino acid. The metal peroxo grouping gives rise to three IR active vibrational modes. These are predominantly O-O stretching v1, the symmetric M-O stretch v2 and the antisymmetric M-O stretch v3. The magnetic moment values indicated that these complexes were diamagnetic in nature suggesting no changes in their oxidation states of the metal ions upon complexation. These data also consistent with six fold coordination of Zr (IV). The electronic spectral data of the complexes showed bands in the region 230-372 nm due to the charge transfer band only. All the complexes of Zr (IV) did not show any remarkable antibacterial activity. It is interesting to note that these complexes were found to be fully inactive against the three pathogenic fungi A. niger, A. fumigatus and A. flarus. Moreover, all the complexes of Zr (IV) metals showed toxic effect against the brine shrimp.

  18. Bifunctional heterogeneous catalysis of silica-alumina-supported tertiary amines with controlled acid-base interactions for efficient 1,4-addition reactions.

    PubMed

    Motokura, Ken; Tanaka, Satoka; Tada, Mizuki; Iwasawa, Yasuhiro

    2009-10-19

    We report the first tunable bifunctional surface of silica-alumina-supported tertiary amines (SA-NEt(2)) active for catalytic 1,4-addition reactions of nitroalkanes and thiols to electron-deficient alkenes. The 1,4-addition reaction of nitroalkanes to electron-deficient alkenes is one of the most useful carbon-carbon bond-forming reactions and applicable toward a wide range of organic syntheses. The reaction between nitroethane and methyl vinyl ketone scarcely proceeded with either SA or homogeneous amines, and a mixture of SA and amines showed very low catalytic activity. In addition, undesirable side reactions occurred in the case of a strong base like sodium ethoxide employed as a catalytic reagent. Only the present SA-supported amine (SA-NEt(2)) catalyst enabled selective formation of a double-alkylated product without promotions of side reactions such as an intramolecular cyclization reaction. The heterogeneous SA-NEt(2) catalyst was easily recovered from the reaction mixture by simple filtration and reusable with retention of its catalytic activity and selectivity. Furthermore, the SA-NEt(2) catalyst system was applicable to the addition reaction of other nitroalkanes and thiols to various electron-deficient alkenes. The solid-state magic-angle spinning (MAS) NMR spectroscopic analyses, including variable-contact-time (13)C cross-polarization (CP)/MAS NMR spectroscopy, revealed that acid-base interactions between surface acid sites and immobilized amines can be controlled by pretreatment of SA at different temperatures. The catalytic activities for these addition reactions were strongly affected by the surface acid-base interactions.

  19. Kinetics of the reactions of the acid anhydrides with aromatic amines in aprotic solvents. M.S. Thesis. Final Report

    NASA Technical Reports Server (NTRS)

    Sugg, E.; Mason, J. G.

    1983-01-01

    Work has revealed that diamine derivatives of diphenylmethane (IV), diphenyl ether (V), benzophenone (IV), fluorene (VII), and fluorenone (VIII) polymerizations with pyromellitic dianhydride in DMA were dependent on the basicity of the amine compound. The correlation between the basicity of the amine and its reactivity with phthalic anhydride was determined. Basicity measurements were made by potentiometric titration of each amine in an acetonitrile-water solvent system, from which the pKa of the amine could be determined. Reactivity was defined in terms of the second order rate constant derived form spectrophotometric examination of the reaction between each amine and phthalic anhydride in DMA. This reaction was expected to proceed in either one (for a monoamine) or two (for a diamine) stages.

  20. Hexamethyldisilazane as an acylation generator for perfluorocarboxylic acids in quantitative derivatization of primary phenylalkyl amines confirmed by GC/MS and computations.

    PubMed

    Molnár, Borbála; Csámpai, Antal; Molnár-Perl, Ibolya

    2015-01-20

    A novel, selective acylation of primary phenylalkyl amines (PPAAs) using hexamethyldisilazane (HMDS) and perfluorocarboxylic acids (PFCAs) is noted. Couples, like HMDS and trifluoroacetic acid, HMDS and pentafluoropropionic acid, or HMDS and heptafluorobutyric acid trigger PPAAs’ quantitative acylation. Processes’ selectivity was characterized by applying all couples to derivatize benzyl, 2-phenylethyl, 3-phenylpropyl, 4-phenylbutyl amines, and their relevant substituted versions. Aliphatic amines were unreactive. Identification, quantification, proportionality, and stoichiometry in derivatization processes were determined by gas chromatography/mass spectrometry. Reaction conditions were optimized depending on reagents’ molar ratios, solvents, and temperatures applied. The new acylation method, in comparison to the traditional ones, obtained with trifluoroacetic anhydride, heptafluorobutyric anhydride, and N-methyl-bis(trifluoroacetamide), offers numerous advantages. Derivatives, provided by couples, can be directly injected onto the column, avoiding loss of species, saving time, work, and cost in the preparation process. Due to traditional reagents’ excess evaporation by nitrogen drying, the loss of trifluoroacylated species proved to be 65% or less. Regarding heptafluorobutyryl species, their losses varied between 25% and 5%. Unified huge responses, obtained with the HMDS and PFCA couples are attributable to their direct injection onto the column and to fragments sourced from the molecular ions and from their self-chemical ionization ([M]•+, [M+147]+, i.e., [M+(CH3)2–Si═O–Si–(CH3)3]+). The reaction mechanism, due to the HMDS symmetrical structure, acting HMDS as acylation generator for PFCAs, was confirmed by density functional theory (DFT) computation.

  1. Amino Acids from Icy Amines: A Radiation-Chemical Approach to Extraterrestrial Synthesis

    NASA Technical Reports Server (NTRS)

    Dworkin, J. P.; Moore, M. H.

    2010-01-01

    Detections of amino acids in meteorites go back several decades, with at least 100 such compounds being reported for the Murchison meteorite alone. The presence of these extraterrestrial molecules raises questions as to their formation, abundance, thermal stability, racemization, and possible subsequent reactions. Although all of these topics have been studied in laboratories, such work often involves many variables and unknowns. This has led us to seek out model systems with which to uncover reaction products, test chemical predictions, and sited light on underlying reaction mechanisms. This presentation will describe one such study, focusing on amino-acid formation in ices.

  2. Electrochemical technique and copper-promoted transformations: selective hydroxylation and amination of arylboronic acids.

    PubMed

    Qi, Hong-Lin; Chen, Dong-Song; Ye, Jian-Shan; Huang, Jing-Mei

    2013-08-01

    An efficient and selective electrosynthesis of phenols and anilines from arylboronic acids in aqueous ammonia is achieved in an undivided cell. By simply changing the concentration of aqueous ammonia and the anode potential, good yields of phenols and anilines can be obtained chemoselectively with high reaction rates. We propose that anodic oxidation could have played an important role in these transformations. PMID:23808633

  3. Hydrophilic and blue fluorescent N-doped carbon dots from tartaric acid and various alkylol amines under microwave irradiation

    NASA Astrophysics Data System (ADS)

    Xu, Minghan; Xu, Shusheng; Yang, Zhi; Shu, Mengjun; He, Guili; Huang, Da; Zhang, Liling; Li, Li; Cui, Daxiang; Zhang, Yafei

    2015-09-01

    The desired control of particle size, doping element composition, and surface structure of carbon dots (CDs) are vital for understanding the fluorescence mechanism and exploring their potential applications. Herein, nitrogen-doped CDs (N-doped CDs) have been synthesized with tartaric acid and various alkylol amines (monoethanolamine, biethanolamine and triethanolamine) under microwave irradiation. A systematic investigation was performed to characterize the N-doped CDs. It is found that with increasing nitrogen proportion, the fluorescent quantum yield and lifetime of N-doped CDs increases, whereas cell toxicity decreases. In other words, N-doped CDs synthesized by tartaric acid and monoethanolamine have the highest nitrogen content, the highest fluorescent quantum yield, the longest lifetime and the lowest cell toxicity. A corresponding mechanism has been proposed. Moreover, as-synthesized N-doped CDs have been applied for selectively detecting the Fe3+ ion and writing letters as a fluorescent ink.The desired control of particle size, doping element composition, and surface structure of carbon dots (CDs) are vital for understanding the fluorescence mechanism and exploring their potential applications. Herein, nitrogen-doped CDs (N-doped CDs) have been synthesized with tartaric acid and various alkylol amines (monoethanolamine, biethanolamine and triethanolamine) under microwave irradiation. A systematic investigation was performed to characterize the N-doped CDs. It is found that with increasing nitrogen proportion, the fluorescent quantum yield and lifetime of N-doped CDs increases, whereas cell toxicity decreases. In other words, N-doped CDs synthesized by tartaric acid and monoethanolamine have the highest nitrogen content, the highest fluorescent quantum yield, the longest lifetime and the lowest cell toxicity. A corresponding mechanism has been proposed. Moreover, as-synthesized N-doped CDs have been applied for selectively detecting the Fe3+ ion and writing

  4. Extraction of Zr(IV) from hydrochloric acid with tri-octyl amine and Cyanex 921 in kerosene

    NASA Astrophysics Data System (ADS)

    Bhatta, Bhikari Charan; Panda, Nandita; Mishra, Sujata

    2013-09-01

    This article reports the extraction of zirconium (IV) from aqueous HCl solution by tri-octyl amine (TOA), Cyanex 921, and their binary mixture using kerosene as the diluent. The effect of some parameters on the extraction of Zr(IV) was investigated such as equilibration time, aqueous phase acidity, extractant molarity, chloride ion concentration, nature of diluents, and temperature. The extraction of Zr(IV) was found to be 99% from 7.5 M HCl using the mixture of extractants containing 0.1 M TOA and 0.02 M Cyanex 921 in kerosene. Kerosene was found to be the effective diluent for the extraction of Zr(IV) with the binary mixture of TOA and Cyanex 921. The positive enthalpy change and positive entropy change in the binary extraction system show the endothermic process with an increase in entropy. Stripping of Zr(IV) from the loaded organic phase containing the mixture of TOA (0.1 M) and Cyanex 921 (0.02 M) indicates that HNO3 and Na2CO3 are the best stripping agents.

  5. Lipid bilayer permeation of aliphatic amine and carboxylic acid drugs: rates of insertion, translocation and dissociation from MD simulations.

    PubMed

    Oruç, Tuğçe; Küçük, Sami Emre; Sezer, Deniz

    2016-09-21

    Aliphatic amines (AAs) and carboxylic acids (CAs) constitute the two most commonly occurring chemical groups among orally active drugs [Manallack, et al., ChemMedChem, 2013, 8, 242]. Here, we aim to rationalize this observation in terms of molecular properties that are essential for drug bioavailability. To this end, the permeation of the AA drug dyclonine and the CA drug 4-phenylbutyrate through a lipid bilayer is studied with molecular dynamics (MD) simulations. Permeability coefficients for the neutral and ionized forms of these drugs are calculated using the inhomogeneous solubility-diffusion model. To draw conclusions about other AA and CA drugs, the permeability coefficient is expressed as a sum over contributions from drug insertion into, translocation across, and dissociation from the lipid bilayer. Simple but general expressions for each of these separate steps are obtained and validated against the MD simulations of dyclonine and phenylbutyrate. We conclude that the neutral forms of most AA and CA drugs have large permeability coefficients (>1 cm s(-1)), while their ionized forms ensure solubility in aqueous environments. Thus, a physicochemical rationale for the reported abundance of AAs and CAs among drugs is provided.

  6. Synthesis and characterization of secondary nitrosamines from secondary amines using sodium nitrite and p-toluenesulfonic acid.

    PubMed

    Miró Sabaté, Carles; Delalu, Henri

    2015-03-01

    We synthesized nitrosamines (R2N-NO) with R = iPr (1), nPr (2), nBu (3), and hydroxyethyl (4) from the amine using sodium nitrite/p-toluenesulfonic acid in CH2Cl2. The rate of formation of 1-4 increases in the direction iPr

  7. Lipid bilayer permeation of aliphatic amine and carboxylic acid drugs: rates of insertion, translocation and dissociation from MD simulations.

    PubMed

    Oruç, Tuğçe; Küçük, Sami Emre; Sezer, Deniz

    2016-09-21

    Aliphatic amines (AAs) and carboxylic acids (CAs) constitute the two most commonly occurring chemical groups among orally active drugs [Manallack, et al., ChemMedChem, 2013, 8, 242]. Here, we aim to rationalize this observation in terms of molecular properties that are essential for drug bioavailability. To this end, the permeation of the AA drug dyclonine and the CA drug 4-phenylbutyrate through a lipid bilayer is studied with molecular dynamics (MD) simulations. Permeability coefficients for the neutral and ionized forms of these drugs are calculated using the inhomogeneous solubility-diffusion model. To draw conclusions about other AA and CA drugs, the permeability coefficient is expressed as a sum over contributions from drug insertion into, translocation across, and dissociation from the lipid bilayer. Simple but general expressions for each of these separate steps are obtained and validated against the MD simulations of dyclonine and phenylbutyrate. We conclude that the neutral forms of most AA and CA drugs have large permeability coefficients (>1 cm s(-1)), while their ionized forms ensure solubility in aqueous environments. Thus, a physicochemical rationale for the reported abundance of AAs and CAs among drugs is provided. PMID:27539552

  8. Carbonic anhydrase activators: an activation study of the human mitochondrial isoforms VA and VB with amino acids and amines.

    PubMed

    Vullo, Daniela; Nishimori, Isao; Innocenti, Alessio; Scozzafava, Andrea; Supuran, Claudiu T

    2007-03-01

    The mitochondrial isozymes of human carbonic anhydrase (hCA, EC 4.2.1.1), hCA VA and hCA VB, were investigated for activation with a series of amino acids and amines. D-His, L-DOPA, histamine, dopamine, and 4-(2-aminoethyl)morpholine were excellent hCA VA activators, with KAs in the range of 10-130 nM. Good hCA VB activating effects were identified for L-His, D-Phe, D-DOPA, L-Trp, L-Tyr, serotonin, and 2-(2-aminoethyl)-pyridine, with KAs in the range of 44-110 nM. All these activators enhanced kcat, having no effect on KM, favoring thus the rate-determining step in the catalytic cycle, the proton transfer reactions between the active site and environment. The activation pattern of the two mitochondrial isoforms is very different from each other and as compared to those of the cytosolic isoforms hCA I and II. PMID:17174092

  9. Effect of ethanol amine plasmalogens on Fe-induced peroxidation of arachidonic acid in dipalmitoylphosphatidylcholine vesicles.

    PubMed

    Omodeo Salè, M F; Rizzo, A M; Masserini, M

    2000-12-01

    We have investigated the influence of ethanolamine plasmalogens on iron-induced oxidation of arachidonic acid in dipalmitoylphosphatidylcholine (DPPC) vesicles. Lipoperoxidation was induced by the addition of 50 microM FeSO4 and studied above (50 degrees C) and below (15 degrees C) the gel-to liquid transition temperature of the vesicles, at two different pH values (7.4 or 6.4). The extent of peroxidation was measured as thiobarbituric reactive product formed and the influence exerted by ethanolamine plasmalogens (PEPL) in this process was compared to that of dipalmitoylphosphatidylethanolamine (DPPE) and diacylphosphatidylethanolamines (DAPE). The extent of peroxidation of arachidonic acid embedded in DPPC vesicles was similar at the two temperatures and greater at 50 degrees C under acidic conditions. However, the peroxidative process was significantly decreased at 50 degrees C in the presence of PEPL, but not of DPPE or DAPE and the inhibitory effect was enhanced at pH 6.4. The possibility that a different phase distribution of the phospholipids, namely a transition from a lamellar to a hexagonal phase, may play a role in the scavenger effect of ethanolamine plasmalogens is discussed. PMID:11145167

  10. Acid synthesis of luminescent amine-functionalized or erbium-doped silica spheres for biological applications.

    PubMed

    Enrichi, Francesco; Trave, Enrico; Bersani, Marco

    2008-03-01

    In this work we discuss and investigate the morphological and optical properties of luminescent silica spheres which can have interesting applications in bioimaging and biosensing. The spheres are synthesized following an acid route by the hydrolysis and condensation of tetraethylortosilicate (TEOS) and can be functionalized by incorporation of aminopropyl-triethoxysilane (APTES) during the synthesis, inducing a significant luminescence that can be attributed to a recombination mechanism from localized organic defects related to -NH(2) groups. It is shown that the acid synthesis route produces very regular spherical particles, but their diameter vary in the range of 200-4,000 nm. The luminescence properties have been investigated and optimized by variation of the annealing temperature for the functionalized spheres, obtaining the most efficient PL emission after a thermal treatment of 1 h at 600 degrees C in air. Moreover, the possibility to introduce rare earths like erbium in the spheres was also studied and the corresponding Er(3) luminescence emission at 1.53 microm is reported in terms of intensity and lifetime, pointing out that erbium can be easily and efficiently incorporated during the acid synthesis giving high PL intensity with a good lifetime of 3.9 ms.

  11. Oxygen uptake after electron transfer from amines, amino acids and ascorbic acid to triplet flavins in air-saturated aqueous solution.

    PubMed

    Görner, Helmut

    2007-05-25

    The photolysis of lumichrome, riboflavin, flavin mononucleotide (FMN) and flavin adenine dinucleotide (FAD) was studied in air-saturated aqueous solution at room temperature in the presence of appropriate electron donors: ascorbic acid, aromatic amino acids or amines, e.g. ethylenediaminetetraacetate (EDTA). The overall reaction is conversion of oxygen via the hydroperoxyl/superoxide radical into hydrogen peroxide. The quantum yield of oxygen uptake increases with the donor concentration, e.g. up to 0.3 for riboflavin, FMN or FAD in the presence of EDTA or ascorbic acid (0.3-10mM). The formation of H(2)O(2) is initiated by quenching of the acceptor triplet state by the electron donor and subsequent reaction of the semiquinone radical with oxygen. Specific properties of flavins are discussed including the radicals involved and the pH and concentration dependences. The quantum yield of photodegradation is low under air, but substantial under argon, where the major product absorbing in the visible spectral range is the corresponding hydroquinone. PMID:17395476

  12. NMR chemical shifts in amino acids: Effects of environments, electric field, and amine group rotation

    SciTech Connect

    Yoon, Young-Gui; Pfrommer, Bernd G.; Louie, Steven G.; Canning, Andrew

    2002-03-03

    The authors present calculations of NMR chemical shifts in crystalline phases of some representative amino acids such as glycine, alanine, and alanyl-alanine. To get an insight on how different environments affect the chemical shifts, they study the transition from the crystalline phase to completely isolated molecules of glycine. In the crystalline limit, the shifts are dominated by intermolecular hydrogen-bonds. In the molecular limit, however, dipole electric field effects dominate the behavior of the chemical shifts. They show that it is necessary to average the chemical shifts in glycine over geometries. Tensor components are analyzed to get the angle dependent proton chemical shifts, which is a more refined characterization method.

  13. Amine-modified hyaluronic acid-functionalized porous silicon nanoparticles for targeting breast cancer tumors

    NASA Astrophysics Data System (ADS)

    Almeida, Patrick V.; Shahbazi, Mohammad-Ali; Mäkilä, Ermei; Kaasalainen, Martti; Salonen, Jarno; Hirvonen, Jouni; Santos, Hélder A.

    2014-08-01

    Active targeting of nanoparticles to receptor-overexpressing cancer cells has great potential for enhancing the cellular uptake of nanoparticles and for reducing fast clearance of the nanoparticles from the body. Herein, we present a preparation method of a porous silicon (PSi)-based nanodelivery system for breast cancer targeting, by covalently conjugating a synthesized amide-modified hyaluronic acid (HA+) derived polymer on the surface of undecylenic acid-modified thermally hydrocarbonized PSi (UnTHCPSi) nanoparticles. The resulting UnTHCPSi-HA+ nanoparticles showed relatively small size, reduced polydispersibility, high biocompatibility, improved colloidal and human plasma stability, as well as enhanced cellular interactions and internalization. Moreover, we demonstrated that the enhanced cellular association of UnTHCPSi-HA+ relies on the capability of the conjugated HA+ to bind and consequently target CD44 receptors expressed on the surface of breast cancer cells, thus making the HA+-functionalized UnTHCPSi nanoparticles a suitable and promising nanoplatform for the targeting of CD44-overexpressing breast tumors and for drug delivery.Active targeting of nanoparticles to receptor-overexpressing cancer cells has great potential for enhancing the cellular uptake of nanoparticles and for reducing fast clearance of the nanoparticles from the body. Herein, we present a preparation method of a porous silicon (PSi)-based nanodelivery system for breast cancer targeting, by covalently conjugating a synthesized amide-modified hyaluronic acid (HA+) derived polymer on the surface of undecylenic acid-modified thermally hydrocarbonized PSi (UnTHCPSi) nanoparticles. The resulting UnTHCPSi-HA+ nanoparticles showed relatively small size, reduced polydispersibility, high biocompatibility, improved colloidal and human plasma stability, as well as enhanced cellular interactions and internalization. Moreover, we demonstrated that the enhanced cellular association of Un

  14. The role of boronic acids in accelerating condensation reactions of α-effect amines with carbonyls.

    PubMed

    Gillingham, Dennis

    2016-08-10

    A broad palette of bioconjugation reactions are available for chemical biologists, but an area that still requires investigation is high-rate constant reactions. These are indispensable in certain applications, particularly for in vivo labelling. Appropriately positioned boronic acids accelerate normally sluggish Schiff base condensations of α-effect nucleophiles by five orders of magnitude - providing a new entry to the rare set of reactions that have a rate constant above 100 M(-1) s(-1) under physiological conditions. I summarize here a number of recent reports, including work from my own group, and outline a mechanistic picture that explains the differing behaviour of seemingly similar substrate classes.

  15. Synthesis and evaluation of quinazoline amino acid derivatives as mono amine oxidase (MAO) inhibitors.

    PubMed

    Khattab, Sherine Nabil; Haiba, Nesreen Saied; Asal, Ahmed Mosaad; Bekhit, Adnan A; Amer, Adel; Abdel-Rahman, Hamdy M; El-Faham, Ayman

    2015-07-01

    A series of quinazolinone amino acid ester and quinazolinone amino acid hydrazides were prepared under microwave irradiation as well as conventional condition. The microwave irradiation afforded the product in less reaction time, higher yield and purity. The structures of the synthesized compounds were confirmed by IR, NMR, and elemental analysis. The new synthesized compounds were studied for their monoamine oxidase inhibitory activity. They showed more selective inhibitory activity toward MAO-A than MAO-B. Compounds 7, 10, and 15 showed MAO-A inhibition activity (IC50=3.6×10(-9), 2.8×10(-9), 2.1×10(-9) M, respectively) comparable to that of the standard clorgyline (IC50=2.9×10(-9)M). 2-(2-(Benzo[d][1,3]dioxol-5-yl)-4-oxo-1,2-dihydroquinazolin-3(4H)-yl)acetohydrazide 15 showed selective MAO-A inhibition activity (SI=39524) superior to that of the standard clorgyline (SI=33793). The acute toxicity of the synthesized compounds was determined. In addition, computer-assisted simulated docking experiments were performed to rationalize the biological activity. PMID:25922182

  16. Synthesis and evaluation of quinazoline amino acid derivatives as mono amine oxidase (MAO) inhibitors.

    PubMed

    Khattab, Sherine Nabil; Haiba, Nesreen Saied; Asal, Ahmed Mosaad; Bekhit, Adnan A; Amer, Adel; Abdel-Rahman, Hamdy M; El-Faham, Ayman

    2015-07-01

    A series of quinazolinone amino acid ester and quinazolinone amino acid hydrazides were prepared under microwave irradiation as well as conventional condition. The microwave irradiation afforded the product in less reaction time, higher yield and purity. The structures of the synthesized compounds were confirmed by IR, NMR, and elemental analysis. The new synthesized compounds were studied for their monoamine oxidase inhibitory activity. They showed more selective inhibitory activity toward MAO-A than MAO-B. Compounds 7, 10, and 15 showed MAO-A inhibition activity (IC50=3.6×10(-9), 2.8×10(-9), 2.1×10(-9) M, respectively) comparable to that of the standard clorgyline (IC50=2.9×10(-9)M). 2-(2-(Benzo[d][1,3]dioxol-5-yl)-4-oxo-1,2-dihydroquinazolin-3(4H)-yl)acetohydrazide 15 showed selective MAO-A inhibition activity (SI=39524) superior to that of the standard clorgyline (SI=33793). The acute toxicity of the synthesized compounds was determined. In addition, computer-assisted simulated docking experiments were performed to rationalize the biological activity.

  17. Amine-modified hyaluronic acid-functionalized porous silicon nanoparticles for targeting breast cancer tumors.

    PubMed

    Almeida, Patrick V; Shahbazi, Mohammad-Ali; Mäkilä, Ermei; Kaasalainen, Martti; Salonen, Jarno; Hirvonen, Jouni; Santos, Hélder A

    2014-09-01

    Active targeting of nanoparticles to receptor-overexpressing cancer cells has great potential for enhancing the cellular uptake of nanoparticles and for reducing fast clearance of the nanoparticles from the body. Herein, we present a preparation method of a porous silicon (PSi)-based nanodelivery system for breast cancer targeting, by covalently conjugating a synthesized amide-modified hyaluronic acid (HA(+)) derived polymer on the surface of undecylenic acid-modified thermally hydrocarbonized PSi (UnTHCPSi) nanoparticles. The resulting UnTHCPSi-HA(+) nanoparticles showed relatively small size, reduced polydispersibility, high biocompatibility, improved colloidal and human plasma stability, as well as enhanced cellular interactions and internalization. Moreover, we demonstrated that the enhanced cellular association of UnTHCPSi-HA(+) relies on the capability of the conjugated HA(+) to bind and consequently target CD44 receptors expressed on the surface of breast cancer cells, thus making the HA(+)-functionalized UnTHCPSi nanoparticles a suitable and promising nanoplatform for the targeting of CD44-overexpressing breast tumors and for drug delivery.

  18. N-acyl amines of docosahexaenoic acid and other n–3 polyunsatured fatty acids – from fishy endocannabinoids to potential leads

    PubMed Central

    Meijerink, Jocelijn; Balvers, Michiel; Witkamp, Renger

    2013-01-01

    N–3 long-chain polyunsaturated fatty acids (n–3 LC-PUFAs), in particular α-linolenic acid (18:3n-3), eicosapentaenoic acid (EPA; 20:5n-3) and docosahexaenoic acid (DHA; 22:6n-3) are receiving much attention because of their presumed beneficial health effects. To explain these, a variety of mechanisms have been proposed, but their interactions with the endocannabinoid system have received relatively little attention so far. However, it has already been shown some time ago that consumption of n–3 LC-PUFAs not only affects the synthesis of prototypic endocannabinoids like anandamide but also stimulates the formation of specific n–3 LC-PUFA-derived conjugates with ethanolamine, dopamine, serotonin or other amines. Some of these fatty amides show overlapping biological activities with those of typical endocannabinoids, whereas others possess distinct and sometimes largely unknown receptor affinities and other properties. The ethanolamine and dopamine conjugates of DHA have been the most investigated thus far. These mediators may provide promising new leads to the field of inflammatory and neurological disorders and for other pharmacological applications, including their use as carrier molecules for neurotransmitters to target the brain. Furthermore, combinations of n–3 LC-PUFA-derived fatty acid amides, their precursors and FAAH inhibitors offer possibilities to optimise their effects in health and disease. Linked Articles This article is part of a themed section on Cannabinoids. To view the other articles in this section visit http://dx.doi.org/10.1111/bph.2013.169.issue-4 & http://dx.doi.org/10.1111/bph.2012.167.issue-8 PMID:23088259

  19. A Lewis basicity scale in dichloromethane for amines and common nonprotogenic solvents using a zinc(II) Schiff-base complex as reference Lewis acid.

    PubMed

    Oliveri, Ivan Pietro; Maccarrone, Giuseppe; Di Bella, Santo

    2011-11-01

    A consistent, reliable scale of Lewis basicity in dichloromethane for 26 bases, involving amines and nonprotogenic solvents, is presented. A Lewis acidic Zn(II) Schiff-base complex, involving formation of stable 1:1 adducts is used as reference acid. Evaluation of binding constants is achieved from spectrophotometric titrations, by the least-squares nonlinear regression of multiwavelength spectrophotometric data. This Lewis basicity scale represents a unique set of data reflecting the actual Lewis basicity with respect this "real world" Lewis acidic species. The comparison of present Lewis basicity scale with data reported in the literature indicates that while for the involved solvents their relative basicity is scarcely affected by the reference Lewis acid, in contrast for sterically encumbered amines the Lewis basicity seems to be dependent from the reference species. Thus, Lewis basicity is governed by the steric hindrance at the donor atom and involves very different relative basicities than those predicted considering typical reference Lewis acids. This is expected to have a major involvement in the organic synthesis and catalysis, given the sterically encumbered nature of commonly involved Lewis acidic organometallic complexes.

  20. Carbonic anhydrase activators: the first activation study of the human secretory isoform VI with amino acids and amines.

    PubMed

    Nishimori, Isao; Onishi, Saburo; Vullo, Daniela; Innocenti, Alessio; Scozzafava, Andrea; Supuran, Claudiu T

    2007-08-01

    The secretory isozyme of human carbonic anhydrase (hCA, EC 4.2.1.1), hCA VI, has been cloned, expressed, and purified in a bacterial expression system. The kinetic parameters for the CO(2) hydration reaction proved hCA VI to possess a k(cat) of 3.4 x 10(5)s(-1) and k(cat)/K(M) of 4.9 x 10(7)M(-1)s(-1) (at pH 7.5 and 20 degrees C). hCA VI has a significant catalytic activity for the physiological reaction, of the same order of magnitude as the ubiquitous isoform CA I or the transmembrane, tumor-associated isozyme CA IX. A series of amino acids and amines were shown to act as CA VI activators, with variable efficacies. l-His, l-Trp, and dopamine showed weak CA VI activating effects (K(A)s in the range of 21-42 microM), whereas d-His, d-Phe, l-DOPA, l-Trp, serotonin, and some pyridyl-alkylamines were better activators, with K(A)s in the range of 13-19 microM. The best CA VI activators were l-Phe, d-DOPA, l-Tyr, 4-amino-l-Phe, and histamine, with K(A)s in the range of 1.23-9.31 microM. All these activators enhance k(cat), having no effect on K(M), participating thus in the rate determining step in the catalytic cycle, the proton transfer reactions between the enzyme active site and the environment. PMID:17499996

  1. Heavy silicon isotopic composition of silicic acid and biogenic silica in Arctic waters over the Beaufort shelf and the Canada Basin

    NASA Astrophysics Data System (ADS)

    Varela, D. E.; Brzezinski, M. A.; Beucher, C. P.; Jones, J. L.; Giesbrecht, K. E.; Lansard, B.; Mucci, A.

    2016-06-01

    The silicon isotopic composition of silicic acid (δ30Si(OH)4) and biogenic silica (δ30Si-bSiO2) were measured for the first time in marine Arctic waters from the Mackenzie River delta to the deep Canada Basin in the late summer of 2009. In the upper 100 m of the water column, δ30Si(OH)4 signals (+1.82‰ to +3.08‰) were negatively correlated with the relative contribution of Mackenzie River water. The biogenic Si isotope fractionation factor estimated using an open system model, 30ɛ = -0.97 ± 0.17‰, agrees well with laboratory and global-ocean estimates. Nevertheless, the δ30Si dynamics of this region may be better represented by closed system isotope models that yield lower values of 30ɛ, between -0.33‰ and -0.41‰, depending on how the contribution of sea-ice diatoms is incorporated. In the upper 400 m, δ30Si-bSiO2 values were among the heaviest ever measured in marine suspended bSiO2 (+2.03‰ to +3.51‰). A positive correlation between δ30Si-bSiO2 and sea-ice cover implies that heavy signals can result from isotopically heavy sea-ice diatoms introduced to pelagic assemblages. Below the surface bSiO2 production zone, the δ30Si(OH)4 distribution followed that of major water masses. Vertical δ30Si(OH)4 profiles showed a minimum (average of +1.84 ± 0.10‰) in the upper halocline (125-200 m) composed of modified Pacific water and heavier average values (+2.04 ± 0.11‰) in Atlantic water (300-500 m deep). In the Canada Basin Deep Water (below 2000 m), δ30Si(OH)4 averaged +1.88 ± 0.12‰, which represents the most positive value ever measured anywhere in the deep ocean. Since most Si(OH)4 enters the Arctic from shallow depths in the Atlantic Ocean, heavy deep Arctic δ30Si(OH)4 signals likely reflect the influx of relatively heavy intermediate Atlantic waters. A box model simulation of the global marine δ30Si(OH)4 distribution successfully reproduced the observed patterns, with the δ30Si(OH)4 of the simulated deep Arctic Ocean being the

  2. Excited state electron distribution and role of the terminal amine in acidic and basic tryptophan dipeptide fluorescence

    NASA Astrophysics Data System (ADS)

    Eisenberg, Azaria S.; Nathan, Moshe; Juszczak, Laura J.

    2016-08-01

    The results of quantum yield (QY) study of tryptophanyl glutamate (Trp-Glu), tryptophanyl lysine (Trp-Lys) and lysinyl tryptophan (Lys-Trp) dipeptides over the pH range, 1.5-13, show that the charge state of the N-terminal amine, and not the nominal molecular charge determines the QY. When the terminal amine is protonated, QY is low (10-2) for all three dipeptides. As the terminal amine cation is found proximal to the indole ring in Trp-Glu and Trp-Lys conformers but not in those for Lys-Trp, its effect may lie only in the partitioning of energy between nonradiative processes, not on QY reduction. QY is also low when both the N-terminal amine and indole amine are deprotonated. These two low QY states can be distinguished by fluorescence lifetime measurement. Molecular dynamics simulation shows that the Chi 1 conformers persist for tens of nanoseconds such that 100-101 ns lifetimes may be associated with individual Chi 1 conformers. The ground state electron density or isosurface of high QY (0.30) 3-methyindole has a uniform electron density over the indole ring as do the higher QY Trp dipeptide conformers. This validates the association of ground state isosurfaces with QY. Excited state orbitals from calculated high intensity, low energy absorption transitions are typically centered over the indole ring for higher QY dipeptide species and off the ring in lower QY species. Thus excited state orbitals substantiate the earlier finding that the ground state isosurface charge density pattern on the indole ring can be predictive of QY.

  3. A base-mediated self-propagative Lossen rearrangement of hydroxamic acids for the efficient and facile synthesis of aromatic and aliphatic primary amines.

    PubMed

    Ohtsuka, Naoya; Okuno, Moriaki; Hoshino, Yujiro; Honda, Kiyoshi

    2016-10-14

    A variety of aromatic and aliphatic hydroxamic acids were converted to the corresponding primary amines via base-mediated rearrangement. This rearrangement could proceed with less than 1 equiv. of K2CO3 in polar solvents under thermal conditions with no external reagents. This rearrangement has several features including no external activating agents needed for promoting the rearrangement, less than one equivalent of a base is sufficient for the reaction, and a clean reaction in which only carbon dioxide is produced as a by-product. A self-propagating mechanism via an isocyanate intermediate is proposed and elementary reaction steps, namely, chain propagation reactions are supported by experiments. PMID:27605448

  4. Intercalation of the layered solid acid HCa/sub 2/Nb/sub 3/O/sub 10/ by organic amines

    SciTech Connect

    Jacobson, A.J.; Johnson, J.W.; Lewandowski, J.T.

    1987-01-01

    Layered compounds of formula C/sub n/H/sub 2n+1/NH/sub 3/Ca/sub 2/Nb/sub 3/O/sub 10/ are formed by reaction of n-alkylamines with the solid acid HCa/sub 2/Nb/sub 3/O/sub 10/. Other organic bases such as pyridine can also be intercalated. The lattice constants of the new compounds have been determined by powder X-ray diffraction. The unit cells are tetragonal with a axes that are unchanged with variation of the intercalated amine. The c axes lengths (layer spacings) vary systematically with the hydrocarbon chain length of the alkylamine.

  5. A base-mediated self-propagative Lossen rearrangement of hydroxamic acids for the efficient and facile synthesis of aromatic and aliphatic primary amines.

    PubMed

    Ohtsuka, Naoya; Okuno, Moriaki; Hoshino, Yujiro; Honda, Kiyoshi

    2016-10-14

    A variety of aromatic and aliphatic hydroxamic acids were converted to the corresponding primary amines via base-mediated rearrangement. This rearrangement could proceed with less than 1 equiv. of K2CO3 in polar solvents under thermal conditions with no external reagents. This rearrangement has several features including no external activating agents needed for promoting the rearrangement, less than one equivalent of a base is sufficient for the reaction, and a clean reaction in which only carbon dioxide is produced as a by-product. A self-propagating mechanism via an isocyanate intermediate is proposed and elementary reaction steps, namely, chain propagation reactions are supported by experiments.

  6. Biogenic Synthesis, Purification, and Chemical Characterization of Anti-inflammatory Resolvins Derived from Docosapentaenoic Acid (DPAn-6)

    PubMed Central

    Dangi, Bindi; Obeng, Marcus; Nauroth, Julie M.; Teymourlouei, Mah; Needham, Micah; Raman, Krishna; Arterburn, Linda M.

    2009-01-01

    Enzymatically oxygenated derivatives of the ω-3 fatty acids cis-4,7,10,13,16,19-docosahexaenoic acid (DHA) and cis-5,8,11,14,17-eicosapentaenoic acid, known as resolvins, have potent inflammation resolution activity (Serhan, C. N., Clish, C. B., Brannon, J., Colgan, S. P., Chiang, N., and Gronert, K. (2000) J. Exp. Med. 192, 1197–1204; Hong, S., Gronert, K., Devchand, P. R., Moussignac, R., and Serhan, C. N. (2003) J. Biol. Chem. 278, 14677–14687). Our objective was to determine whether similar derivatives are enzymatically synthesized from other C-22 fatty acids and whether these molecules possess inflammation resolution properties. The reaction of DHA, DPAn-3, and DPAn-6 with 5-, 12-, and 15-lipoxygenases produced oxylipins, which were identified and characterized by liquid chromatography coupled with tandem mass-spectrometry. DPAn-6 and DPAn-3 proved to be good substrates for 15-lipoxygenase. 15-Lipoxygenase proved to be the most efficient enzyme of the three tested for conversion of long chain polyunsaturated fatty acids to corresponding oxylipins. Since DPAn-6 is a major component of Martek DHA-S™ oil, we focused our attention on reaction products obtained from the DPAn-6 and 15-lipoxygenase reaction. (17S)-hydroxy-DPAn-6 and (10,17S)-dihydroxy-DPAn-6 were the main products of this reaction. These compounds were purified by preparatory high performance liquid chromatography techniques and further characterized by NMR, UV spectrophotometry, and tandem mass spectrometry. We tested both compounds in two animal models of acute inflammation and demonstrated that both compounds are potent anti-inflammatory agents that are active on local intravenous as well as oral administration. These oxygenated DPAn-6 compounds can thus be categorized as a new class of DPAn-6-derived resolvins. PMID:19324874

  7. [Rh(III)(Cp*)]-catalyzed ortho-selective direct C(sp(2))-H bond amidation/amination of benzoic acids by N-chlorocarbamates and N-chloromorpholines. A versatile synthesis of functionalized anthranilic acids.

    PubMed

    Ng, Fo-Ning; Zhou, Zhongyuan; Yu, Wing-Yiu

    2014-04-01

    A Rh(III) -catalyzed direct ortho-CH amidation/amination of benzoic acids with N-chlorocarbamates/N-chloromorpholines was achieved, giving anthranilic acids in up to 85 % yields with excellent ortho-selectivity and functional-group tolerance. Successful benzoic acid aminations were achieved with carbamates bearing various amide groups including NHCO2 Me, NHCbz, and NHTroc (Cbz=carbobenzyloxy; Troc=trichloroethylchloroformate), as well as secondary amines, such as morpholines, piperizines, and piperidines, furnishing highly functionalized anthranilic acids. A stoichiometric reaction of a cyclometallated rhodium(III) complex of benzo[h]quinoline with a silver salt of N-chlorocarbamate afforded an amido-rhodium(III) complex, which was isolated and structurally characterized by X-ray crystallography. This finding confirmed that the CN bond formation results from the cross-coupling of N-chlorocarbamate with the aryl-rhodium(III) complex. Yet, the mechanistic details regarding the CN bond formation remain unclear; pathways involving 1,2-aryl migration and rhodium(V)- nitrene are plausible. PMID:24596116

  8. X-ray crystallographic, FT-IR and NMR studies as well as anticancer and antibacterial activity of the salt formed between ionophore antibiotic Lasalocid acid and amines

    NASA Astrophysics Data System (ADS)

    Huczyński, Adam; Rutkowski, Jacek; Wietrzyk, Joanna; Stefańska, Joanna; Maj, Ewa; Ratajczak-Sitarz, Małgorzata; Katrusiak, Andrzej; Brzezinski, Bogumil; Bartl, Franz

    2013-01-01

    Two new complexes of the ionophore antibiotic Lasalocid acid (LAS) with phenylamine (PhA) and butylamine (BuA) were synthesized and their molecular structures were studied using single crystal X-ray diffraction and spectroscopic methods. In the solid state both amines are protonated and all NH3+ protons are hydrogen bonded to etheric, hydroxyl and carboxylic oxygen atoms of the LAS anion. In chloroform solutions the structure observed in the crystal of LAS-BuA complex is preserved and an equilibrium between the LAS-PhA complex and dissociated Lasalocid acid and phenylamine is observed. In vitro antimicrobial tests of the complexes showed a significant activity towards some strains of Gram-positive bacteria. For the first time Lasalocid acid and its complexes with amines were tested in vitro for cytotoxic activity against human cancer cell lines: A-549 (lung), MCF-7 (breast), HT-29 (colon) and mouse cancer cell line P-388 (leukemia). We found that LAS and its complexes are strong cytotoxic agents towards all tested cell lines. The cytostatic activity of the compounds studied is greater than that of cisplatin, indicating that Lasalocid and its complexes are promising candidates for new anticancer drugs.

  9. Amines and Ammonia Measured in the Southeastern U.S. Forest during the 2013 SOAS Field Campaign

    NASA Astrophysics Data System (ADS)

    Lee, S.; You, Y.; Sierra-Hernández, M.; Baumann, K.; Fry, J.; Allen, H.; Draper, D. C.; Edgerton, E.

    2013-12-01

    Amines and ammonia play critical roles in new particle formation, via acid-base reactions at the initial stage of aerosol nucleation. Nitrogen base compounds are important for SOA formation, via formation of salts and condensation of amine photo-oxidation products; they also contribute to the formation of brown organic aerosols. Amines and ammonia can change the acidity and physical state of aerosols to further affect SOA yields. During the Southern Oxidant and Aerosol Study (SOAS) campaign in Centerville, Alabama from June 1 to July 15, 2013, amines and ammonia were simultaneously measured with a chemical ionization mass spectrometer (CIMS) by Kent State University [Yu and Lee, 2012: Environ. Chem. 9, 190-201]. The sensitivity of the CIMS was in the range of 5-10 Hz ion signals for 1 pptv of a base compound, which ultimately allows for the fast-time response detection (less than 1 minute) of ammonia and amines at the pptv level. Additionally, ammonia was also detected with another two independent methods, MARGA (Measuring AeRosols and Gases) by Reed College, and chemiluminescence by ARA. Ammonia concentrations measured by CIMS, MARGA and chemiluminescence were at the ppbv and sub-ppbv level. Over the 6 weeks of the SOAS field study, these three ammonia instruments consistently showed very similar time variations and agreed reasonably well. The CIMS also detected various C1 through C6 amines at the pptv and tens pptv level. Trimethylamine (C3 amine) and ammonia showed similar diurnal trends, temperature and wind direction dependences for most days, implying common natural emission sources of these two base compounds at this forest site. On the other hand, methylamine (C1) and dimethylamine (C2) were much lower than trimethylamine and they did not show clear diurnal variations and temperature dependences. During the brief episode of local biomass burning, concentrations of C3 through C6 amines and ammonia increased rapidly, while methylamine and dimethylamine were

  10. Evidence of Two Functionally Distinct Ornithine Decarboxylation Systems in Lactic Acid Bacteria

    PubMed Central

    Romano, Andrea; Trip, Hein; Lonvaud-Funel, Aline; Lolkema, Juke S.

    2012-01-01

    Biogenic amines are low-molecular-weight organic bases whose presence in food can result in health problems. The biosynthesis of biogenic amines in fermented foods mostly proceeds through amino acid decarboxylation carried out by lactic acid bacteria (LAB), but not all systems leading to biogenic amine production by LAB have been thoroughly characterized. Here, putative ornithine decarboxylation pathways consisting of a putative ornithine decarboxylase and an amino acid transporter were identified in LAB by strain collection screening and database searches. The decarboxylases were produced in heterologous hosts and purified and characterized in vitro, whereas transporters were heterologously expressed in Lactococcus lactis and functionally characterized in vivo. Amino acid decarboxylation by whole cells of the original hosts was determined as well. We concluded that two distinct types of ornithine decarboxylation systems exist in LAB. One is composed of an ornithine decarboxylase coupled to an ornithine/putrescine transmembrane exchanger. Their combined activities results in the extracellular release of putrescine. This typical amino acid decarboxylation system is present in only a few LAB strains and may contribute to metabolic energy production and/or pH homeostasis. The second system is widespread among LAB. It is composed of a decarboxylase active on ornithine and l-2,4-diaminobutyric acid (DABA) and a transporter that mediates unidirectional transport of ornithine into the cytoplasm. Diamines that result from this second system are retained within the cytosol. PMID:22247134

  11. Direct high-performance liquid chromatographic separation of the enantiomers of an aromatic amine and four aminoalcohols using polysaccharide chiral stationary phases and acidic additive.

    PubMed

    Caccamese, Salvatore; Bianca, Salvatore; Carter, Guy T

    2007-08-01

    The HPLC enantiomeric separation of N-benzyl-alpha-methyl-benzylamine, phenylalaninol, tryptophanol, 2 (diphenylhydroxymethyl)pyrrolidine, and isoproterenol was accomplished in the normal-phase mode using two polysaccharide-derived chiral stationary phases (CSPs) and various n-hexane/2-propanol mobile phases with acidic (TFA) or basic (DEA) additive. The compounds were separated without any derivatization and separation factor range between 2.09 and 1.09 with resolution factor 3.4 and 0.4, respectively. The best separation of the enantiomers of the amine was achieved on amylose tris (3, 5-dimethylphenylcarbamate) CSP with TFA additive in the mobile phase; in acidic conditions, instead, the best enantioseparation of the aminoalcohols was achieved on cellulose tris (3, 5-dimethylphenilcarbamate). A long equilibration time of the CSP when switching from an undoped mobile phase to a doped one is required to obtain reproducible results. PMID:17568428

  12. The Apoplastic Copper AMINE OXIDASE1 Mediates Jasmonic Acid-Induced Protoxylem Differentiation in Arabidopsis Roots1

    PubMed Central

    Ghuge, Sandip A.; Carucci, Andrea; Rodrigues-Pousada, Renato A.; Tisi, Alessandra; Franchi, Stefano; Tavladoraki, Paraskevi; Cona, Alessandra

    2015-01-01

    Polyamines are involved in key developmental processes and stress responses. Copper amine oxidases oxidize the polyamine putrescine (Put), producing an aldehyde, ammonia, and hydrogen peroxide (H2O2). The Arabidopsis (Arabidopsis thaliana) amine oxidase gene At4g14940 (AtAO1) encodes an apoplastic copper amine oxidase expressed at the early stages of vascular tissue differentiation in roots. Here, its role in root development and xylem differentiation was explored by pharmacological and forward/reverse genetic approaches. Analysis of the AtAO1 expression pattern in roots by a promoter::green fluorescent protein-β-glucuronidase fusion revealed strong gene expression in the protoxylem at the transition, elongation, and maturation zones. Methyl jasmonate (MeJA) induced AtAO1 gene expression in vascular tissues, especially at the transition and elongation zones. Early protoxylem differentiation was observed upon MeJA treatment along with Put level decrease and H2O2 accumulation in wild-type roots, whereas Atao1 loss-of-function mutants were unresponsive to the hormone. The H2O2 scavenger N,N1-dimethylthiourea reversed the MeJA-induced early protoxylem differentiation in wild-type seedlings. Likewise, Put, which had no effect on Atao1 mutants, induced early protoxylem differentiation in the wild type, this event being counteracted by N,N1-dimethylthiourea treatment. Consistently, AtAO1-overexpressing plants showed lower Put levels and early protoxylem differentiation concurrent with H2O2 accumulation in the root zone where the first protoxylem cells with fully developed secondary wall thickenings are found. These results show that the H2O2 produced via AtAO1-driven Put oxidation plays a role in MeJA signaling leading to early protoxylem differentiation in root. PMID:25883242

  13. Impact of primary amine group from aminophospholipids and amino acids on marine phospholipids stability: non-enzymatic browning and lipid oxidation.

    PubMed

    Lu, F S H; Nielsen, N S; Baron, C P; Diehl, B W K; Jacobsen, C

    2013-11-15

    The main objective of this study was to investigate the oxidative stability and non-enzymatic browning reactions of marine PL in the presence or in the absence of primary amine group from aminophospholipids and amino acids. Marine phospholipids liposomal dispersions were prepared from two authentic standards (phosphatidylcholine and phosphatidylethanolamine) and two purified PL from marine sources with and without addition of amino acids (leucine, methionine and lysine). Samples were incubated at 60°C for 0, 2, 4 and 6days. Non-enzymatic browning reactions were investigated through measurement of (i) Strecker derived volatiles, (ii) yellowness index (YI), (iii) hydrophobic and (iv) hydrophilic pyrroles content. The oxidative stability of the samples was assessed through measurement of secondary lipid derived volatile oxidation products. The result showed that the presence of PE and amino acids caused the formation of pyrroles, generated Strecker derived volatiles, decreased the YI development and lowered lipid oxidation. The lower degree of lipid oxidation in liposomal dispersions containing amino acids might be attributed to antioxidative properties of pyrroles or amino acids. PMID:23790862

  14. Concerted Amidation of Activated Esters: Reaction Path and Origins of Selectivity in the Kinetic Resolution of Cyclic Amines via N-Heterocyclic Carbenes and Hydroxamic Acid Cocatalyzed Acyl Transfer

    PubMed Central

    2015-01-01

    The N-heterocyclic carbene and hydroxamic acid cocatalyzed kinetic resolution of cyclic amines generates enantioenriched amines and amides with selectivity factors up to 127. In this report, a quantum mechanical study of the reaction mechanism indicates that the selectivity-determining aminolysis step occurs via a novel concerted pathway in which the hydroxamic acid plays a key role in directing proton transfer from the incoming amine. This modality was found to be general in amide bond formation from a number of activated esters including those generated from HOBt and HOAt, reagents that are broadly used in peptide coupling. For the kinetic resolution, the proposed model accurately predicts the faster reacting enantiomer. A breakdown of the steric and electronic control elements shows that a gearing effect in the transition state is responsible for the observed selectivity. PMID:25050843

  15. Studies of the biogenic amine transporters. V. Demonstration of two binding sites for the cocaine analog [125I]RTI-55 associated with the 5-HT transporter in rat brain membranes.

    PubMed

    Silverthorn, M L; Dersch, C M; Baumann, M H; Cadet, J L; Partilla, J S; Rice, K C; Carroll, F I; Becketts, K M; Brockington, A; Rothman, R B

    1995-04-01

    Earlier work characterized the binding of the high-affinity cocaine analog 3 beta-(4-125iodophenyl)-tropane-2-carboxylic acid methyl ester ([125I]RTI-55) to membranes prepared from rat caudate. That investigation demonstrated that [125I]RTI-55-labeled serotonin (5-HT) transporters in addition to dopamine (DA) transporters and resolved [125I]RTI-55 binding to 5-HT transporters into two distinct components. In the present study, we characterized [125I]RTI-55 binding to membranes prepared from whole rat brain minus caudate. The first series of experiments established that [125I]RTI-55 labels both DA and 5-HT transporters and that 50 nM paroxetine and either 1000 nM 1-[2-(diphenylmethoxy)ethyl]-4-(3-phenylpropyl)homopiperazine (LR1111) or 500 nM (RTI-120) could be used to block [125I]RTI-55 binding to the 5-HT and DA transporters, thereby generating selective assay conditions for the DA and 5-HT transporters, respectively. Selective lesioning of dopaminergic and serotonergic neurons with intracerebroventricular 6-hydroxydopamine and 5,7-dihydroxytryptamine selectively decreased [125I]RTI-55 binding to DA and 5-HT transporters, respectively, thereby confirming the selectivity of the assay conditions. The ligand-selectivity pattern of the whole brain minus caudate 5-HT transporter correlated significantly with that of the caudate 5-HT transporter, although there were some striking differences for selected test agents. Additional experiments resolved [125I]RTI-55 binding to the 5-HT transporter into two components. A ligand-selectivity analysis of the two components failed to identify a highly selective test agent. In summary, the major findings of the present study are that [125I]RTI-55 labels both DA and 5-HT transporters in membranes prepared from whole brain minus caudate, that 50 nM paroxetine and either 1000 nM LR1111 or 500 nM RTI-120 can be used as a blocking agent to generate selective assay conditions for the DA and 5-HT transporters, respectively, and that [125

  16. Influence of Biogenically Produced Fe(II) and Humic Acid Analogs on the Fate of 2,4,6-Trinitrotoluene (TNT)

    NASA Astrophysics Data System (ADS)

    Borch, T.; Gerlach, R.; Cunningham, A. B.; Peyton, B. M.; Apel, W. A.

    2002-12-01

    Pollution of soil and groundwater with explosives, such as TNT, is a well-known environmental problem. Obviously, a precise risk assessment and evaluation of appropriate remediation strategies of TNT require a fundamental understanding of the processes that govern the transformation of TNT in the subsurface. Recently a number of novel Gram positive metal-reducing bacteria were isolated from enrichments of subsurface soils from Cr(VI) contaminated and uncontaminated zones at the US Department of Energy's Hanford site. In contrast to most known metal-reducing bacteria such as Geobacter spp. and Shewanella spp. the isolates were predominantly Gram-positive and 16S rDNA and phospholipid analysis indicated that the isolates predominantly belonged to commonly observed soil bacteria of the genus Cellulomonas. These isolates proved to be capable of Cr(VI), U(VI), dissolved Fe(III), goethite, maghemite, magnetite, hematite, and hydrous ferric oxide (HFO) reduction. Reduced solid phase iron can mediate the degradation of nitroaromatics, halogenated solvents, azo compounds, arsenate, and other important contaminants. Consequently, batch experiments were conducted with Fe(III) minerals (namely, HFO and Magnetite) to investigate the impact of biogenically produced Fe(II) on the fate of TNT. The humic acid analog anthraquinone-2,6-disulfonate (AQDS), can be reduced by Cellulomonas spp. and was included in these studies because of its ability to function as an electron shuttle between the Fe(III) minerals and the bacterial cell during microbial iron reduction. The work to be presented systematically investigates how different factors control the rate and extent of TNT reduction reactions as well as the mechanisms involved. Anaerobic batch studies show the fastest and most complete reduction of TNT in the presence of HFO and the humic analog AQDS. However, we also observe TNT removal by Cellulomonas in the absence of HFO and AQDS with similar TNT reduction rates but with the

  17. Phenylboronic Acid Solid Phase Extraction Cleanup and Isotope Dilution Liquid Chromatography-Tandem Mass Spectrometry for the Determination of Florfenicol Amine in Fish Muscles.

    PubMed

    Sin, Della Wai-Mei; Ho, Clare; Wong, Yiu-Tung

    2015-01-01

    Florfenicol (FFC) residues in foods are regulated as the sum of florfenicol and its metabolites measured as florfenicol amine (FFA). An isotope dilution LC-MS/MS method utilizing phenylboronic acid (PBA) SPE cleanup is established for the accurate determination of FFA in fish muscles (i.e., salmon and tilapia) after acid catalyzed hydrolysis. Comparisons of the PBA SPE cleanup procedure with other cleanup procedures such as mixed-mode cationic (MCX) SPE and solid supported liquid-liquid extraction were performed. Quantification of FFA in fish muscles was accomplished by using matrix-matched calibration with FFA-D3 as the internal standard. The method was validated with FFA fortified fish muscles at three different levels (50, 100, and 200 μg/kg). Conversion of FFC to FFA by acid catalyzed hydrolysis was evaluated and found to be ≥88%. The recoveries of FFA in fish muscles at the three fortification levels ranged from 89 to 106%, and RSDs were ≤9% in all cases. The LOD values in salmon and tilapia muscles were 0.13 and 1.64 μg/kg, respectively. The LOQ values in salmon and tilapia muscles were 0.29 and 4.13 μg/kg, respectively. This method is suitable for the application in routine control of FFC in fishes according to its residue definition.

  18. [Highly selective analysis of biogenic-related compounds utilizing fluorous chemistry].

    PubMed

    Hayama, Tadashi

    2015-01-01

    Perfluoroalkyl-containing compounds are highly fluorous, meaning that they have a remarkable affinity for one another and effectively exclude non-fluorous species. Utilizing this unique property, we have developed a fluorous derivatization with a liquid chromatographic analysis method for highly selective analysis of target analytes. Although most previous methods focused on extremely sensitive detection-oriented derivatization, the fluorous derivatization method involves highly specific separation for analytes. This method includes perfluoroalkylation of analytes with a fluorous reagent, and separation of the derivatives using a perfluoroalkyl-modified stationary phase LC column. The derivatives can be selectively retained on the fluorous-phase LC column, whereas the non-fluorous derivatives are poorly retained under the same separation conditions. The combination of this method with LC-tandem mass spectrometry (MS/MS) is very useful for complex biological sample analysis, because matrix-induced suppression effects, which are a common problem in LC-MS/MS analysis arising from components of a biological endogenous matrix, have not been observed. We have successfully applied this method to precise and accurate LC-MS/MS analysis of some biogenic compounds, such as sialic acids and biogenic amines, in complex biological samples.

  19. Amine-Amine Exchange in Aminium-Methanesulfonate Aerosols

    SciTech Connect

    Dawson, Matthew L.; Varner, Mychel E.; Perraud, Veronique M.; Ezell, Michael J.; Wilson, Jacqueline M.; Zelenyuk, Alla; Gerber, Robert B.; Finlayson-Pitts, Barbara J.

    2014-12-18

    Aerosol particles are ubiquitous in the atmosphere and have been shown to impact the Earth’s climate, reduce visibility, and adversely affect human health. Modeling the evolution of aerosol systems requires an understanding of the species and mechanisms involved in particle growth, including the complex interactions between particle- and gas-phase species. Here we report studies of displacement of amines (methylamine, dimethylamine or trimethylamine) in methanesulfonate salt particles by exposure to a different gas-phase amine, using a single particle mass spectrometer, SPLAT II. The variation of the displacement with the nature of the amine suggests that behavior is dependent on water in or on the particles. Small clusters of methanesulfonic acid with amines are used as a model in quantum chemical calculations to identify key structural elements that are expected to influence water uptake, and hence the efficiency of displacement by gas-phase molecules in the aminium salts. Such molecular-level understanding of the processes affecting the ability of gas-phase amines to displace particle-phase aminium species is important for modeling the growth of particles and their impacts in the atmosphere.

  20. Sub-Antarctic marine aerosol: dominant contributions from biogenic sources

    NASA Astrophysics Data System (ADS)

    Schmale, J.; Schneider, J.; Nemitz, E.; Tang, Y. S.; Dragosits, U.; Blackall, T. D.; Trathan, P. N.; Phillips, G. J.; Sutton, M.; Braban, C. F.

    2013-09-01

    Biogenic influences on the composition and characteristics of aerosol were investigated on Bird Island (54°00' S, 38°03' W) in the South Atlantic during November and December 2010. This remote marine environment is characterised by large seabird and seal colonies. The chemical composition of the submicron particles, measured by an aerosol mass spectrometer (AMS), was 21% non-sea-salt sulfate, 2% nitrate, 8% ammonium, 22% organics and 47% sea salt including sea salt sulfate. A new method to isolate the sea spray signature from the high-resolution AMS data was applied. Generally, the aerosol was found to be less acidic than in other marine environments due to the high availability of ammonia, from local fauna emissions. By positive matrix factorisation five different organic aerosol (OA) profiles could be isolated: an amino acid/amine factor (AA-OA, 18% of OA mass), a methanesulfonic acid OA factor (MSA-OA, 25%), a marine oxygenated OA factor (M-OOA, 41%), a sea spray OA fraction (SS-OA, 7%) and locally produced hydrocarbon-like OA (HOA, 9%). The AA-OA was dominant during the first two weeks of November and found to be related with the hatching of penguins in a nearby colony. This factor, rich in nitrogen (N : C ratio = 0.13), has implications for the biogeochemical cycling of nitrogen in the area as particulate matter is often transported over longer distances than gaseous N-rich compounds. The MSA-OA was mainly transported from more southerly latitudes where phytoplankton bloomed. The bloom was identified as one of three sources for particulate sulfate on Bird Island, next to sea salt sulfate and sulfate transported from South America. M-OOA was the dominant organic factor and found to be similar to marine OA observed at Mace Head, Ireland. An additional OA factor highly correlated with sea spray aerosol was identified (SS-OA). However, based on the available data the type of mixture, internal or external, could not be determined. Potassium was not associated

  1. Sub-Antarctic marine aerosol: significant contributions from biogenic sources

    NASA Astrophysics Data System (ADS)

    Schmale, J.; Schneider, J.; Nemitz, E.; Tang, Y. S.; Dragosits, U.; Blackall, T. D.; Trathan, P. N.; Phillips, G. J.; Sutton, M.; Braban, C. F.

    2013-03-01

    Biogenic influences on the composition and characteristics of aerosol were investigated on Bird Island (54°00' S, 38°03' W) in the South Atlantic during November and December 2010. This remote marine environment is characterised by large seabird and seal colonies. The chemical composition of the submicron particles, measured by an aerosol mass spectrometer (AMS), was 21% non-sea salt sulfate 2% nitrate, 7% ammonium, 22% organics and 47% sea salt including sea salt sulfate. A new method to isolate the sea salt signature from the high-resolution AMS data was applied. Generally, the aerosol was found to be less acidic than in other marine environments due to the high availability of ammonia, from local fauna emissions. By positive matrix factorisation five different organic aerosol (OA) profiles could be isolated: an amino acids/amine factor (AA-OA, 18% of OA mass), a methanesulfonic acid OA factor (MSA-OA, 25%), a marine oxygenated OA factor (M-OOA, 40%), a sea salt OA fraction (SS-OA, 7%) and locally produced hydrocarbon-like OA (HOA, 9%). The AA-OA was dominant during the first two weeks of November and found to be related with the hatching of penguins in a nearby colony. This factor, rich in nitrogen (C : N ratio = 0.13), has implications for the biogeochemical cycling of nitrogen in the area as particulate matter is often transported over longer distances than gaseous N-rich compounds. The MSA-OA was mainly transported from more southerly latitudes where phytoplankton bloomed. The bloom was identified as one of three sources for particulate sulfate on Bird Island, next to sea salt sulfate and sulfate transported from South America. M-OOA was the dominant organic factor and found to be similar to marine OA observed at Mace Head, Ireland. An additional OA factor highly correlated with sea salt aerosol was identified (SS-OA). However, based on the available data the type of mixture, internal or external, could not be determined. Potassium was not associated to sea

  2. Simultaneous efficient adsorption of Pb2+ and MnO4- ions by MCM-41 functionalized with amine and nitrilotriacetic acid anhydride

    NASA Astrophysics Data System (ADS)

    Chen, Feiyun; Hong, Mingzhu; You, Weijie; Li, Chong; Yu, Yan

    2015-12-01

    A novel adsorbent NH2/MCM-41/NTAA, capable of simultaneous adsorption of cations and anions from aqueous solution, was prepared by immobilization of amine and nitrilotriacetic acid anhydride (NTAA) onto MCM-41. The structures and properties before and after surface modification were systematically investigated through X-ray diffraction (XRD), transmission electron microscope (TEM) and scanning electron microscope (SEM), nitrogen adsorption-desorption, and infrared spectroscopy (FTIR), thermogravimetry (TGA) and X-ray photoelectron spectroscopy (XPS). They together confirm that the amine and NTAA group were chemically bonded to the internal surface of the mesoporous. The NH2/MCM-41/NTAA were used to adsorb Pb2+ and MnO4- in an aqueous solution in a batch system, and the maximum adsorption efficiency was found to occur at pH 5.0 and 3.0, respectively. NH2/MCM-41/NTAA exhibit preferable removal of Pb2+ through electrostatic interactions and chelation, whereas it captures MnO4- by means of electrostatic interactions. The experimental data are fitted the Langmuir isotherm model reasonably well, with the maximum adsorption capacity of 147 mg/g for Pb2+ and of 156 mg/g for MnO4-. The adsorption rates of both Pb2+ and MnO4- are found to follow the pseudo-second order kinetics. Furthermore, the NH2/MCM-41/NTAA adsorbent performs good recyclability and reusability for 5 cycles use. This study indicates a potential applicability of NH2/MCM-41/NTAA as new absorbents for effective simultaneous adsorption of hazardous metal ions and anions from wastewater.

  3. Comparing Organic Aerosol Composition from Marine Biogenic Sources to Seawater and to Physical Sea Spray Models

    NASA Astrophysics Data System (ADS)

    Russell, L. M.; Frossard, A. A.; Sanchez, K.; Massoli, P.; Elliott, S.; Burrows, S. M.; Bates, T. S.; Quinn, P.

    2015-12-01

    In much of the marine atmosphere, organic components in aerosol particles have many sources other than sea spray that contribute organic constituents. For this reason, physical sea spray models provide an important technique for studying the organic composition of particles from marine biogenic sources. The organic composition of particles produced by two different physical sea spray models were measured in three open ocean seawater types: (i) Coastal California in the northeastern Pacific, which is influenced by wind-driven, large-scale upwelling leading to productive or eutrophic (nutrient-rich) seawater and high chl-a concentrations, (ii) George's Bank in the northwestern Atlantic, which is also influenced by nutrient upwelling and eutrophic seawater with phytoplankton productivity and high chl-a concentrations, and (iii) the Sargasso Sea in the subtropical western Atlantic, which is oligotrophic and nutrient-limited, reflected in low phytoplankton productivity and low chl-a concentrations. Fourier transform infrared spectroscopy provides information about the functional group composition that represents the marine organic fraction more completely than is possible with techniques that measure non-refractory mass (vaporizable at 650°C). After separating biogenic marine particles from those from other sources, the measured compositions of atmospheric marine aerosol particles from three ocean regions is 65±12% hydroxyl, 21±9% alkane, 6±6% amine, and 7±8% carboxylic acid functional groups. The organic composition of atmospheric primary marine (ocean-derived) aerosol particles is nearly identical to model generated primary marine aerosol particles from bubbled seawater. Variability in productive and non-productive seawater may be caused by the presence of surfactants that can stabilize the bubble film and lead to preferential drainage of the more soluble (lower alkane group fraction) organic components without substantial changes in overall group composition

  4. Acidity-promoted cellular uptake and drug release mediated by amine-functionalized block polycarbonates prepared via one-shot ring-opening copolymerization.

    PubMed

    Wang, Hua-Fen; Jia, Hui-Zhen; Chu, Yan-Feng; Feng, Jun; Zhang, Xian-Zheng; Zhuo, Ren-Xi

    2014-04-01

    This paper reports a drug nanovehicle self-assembled from an amine-functionalized block copolymer poly(6,14-dimethyl-1,3,9,11-tetraoxa-6,14-diaza-cyclohexadecane-2,10-dione)-block-poly(1,3-dioxepan-2-one) (PADMC-b-PTeMC), which is prepared by controlable ring-opening block copolymerization attractively in a "one-shot feeding" pathway. The copolymers display high cell-biocompatibility with no apparent cytotoxicities detected in 293T and HeLa cells. Due to their amphiphilic nature, PADMC-b-PTeMC copolymers can self-assemble into nanosized micelles capable of loading anticancer drugs such as camptothecin (CPT) and doxorubicin (DOX). In particular, the outer PADMC shell endows the PADMC-b-PTeMC nanomicelles with pH-dependent control over the micellar morphology, cell uptake efficiency, and the drug release pattern. Confocal inspection reveals the remarkably enhanced cellular internalization of drug loaded micelles by cancerous HeLa cells at relatively lower pH 5.8 simulating the mildly acid microenvironment in tumors. Along with the acidity-triggered volume expansion of micelles, an accelerated CPT release in vitro occurs. The obtained results adumbrate the possibility of completely biodegradable PADMC-b-PTeMC as pH-sensitive drug carriers for tumor chemotherapy.

  5. Tris(2-aminoethyl)amine-based α-branched fatty acid amides - Synthesis of lipids and comparative study of transfection efficiency of their lipid formulations.

    PubMed

    Erdmann, Nicole; Wölk, Christian; Schulze, Ingo; Janich, Christopher; Folz, Manuela; Drescher, Simon; Dittrich, Matthias; Meister, Annette; Vogel, Jürgen; Groth, Thomas; Dobner, Bodo; Langner, Andreas

    2015-10-01

    The synthesis of a new class of cationic lipids, tris(2-aminoethyl)amine-based α-branched fatty acid amides, is described resulting in a series of lipids with specific variations in the lipophilic as well as the hydrophilic part of the lipids. In-vitro structure/transfection relationships were established by application of complexes of these lipids with plasmid DNA (pDNA) to different cell lines. The α-branched fatty acid amide bearing two tetradecyl chains and two lysine molecules (T14diLys) in mixture with the co-lipid 1,2-di-[(9Z)-octadec-9-enoyl]-sn-glycero-3-phosphoethanolamine (DOPE) (1/2, n/n) exhibits effective pDNA transfer in three different cell lines, namely Hep-G2, A549, and COS-7. The presence of 10% serum during lipoplex incubation of the cells did not affect the transfection efficiency. Based on that, detailed investigations of the complexation of pDNA with the lipid formulation T14diLys/DOPE 1/2 (n/n) were carried out with respect to particle size and charge using dynamic light scattering (DLS), ζ-potential measurements, and transmission electron microscopy (TEM). Additionally, the lipoplex uptake was investigated by confocal laser scanning microscopy (CLSM). Overall, lipoplexes prepared from T14diLys/DOPE 1/2 (n/n) offer large potential as lipid-based polynucleotide carriers and further justify advanced examinations.

  6. Photochemistry of biogenic gases

    NASA Technical Reports Server (NTRS)

    Levine, Joel S.

    1989-01-01

    The relationship between the biosphere and the atmosphere is examined, emphasizing the composition and photochemistry and chemistry of the troposphere and stratosphere. The reactions of oxygen, ozone, and hydroxyl are reviewed and the fate of the biogenic gases ammonia, methane, reduced sulfur species, reduced halogen species, carbon monoxide, nitric oxide, nitrous oxide, nitrogen, and carbon dioxide are described. A list is given of the concentration and sources of the various gases.

  7. Accurate determination of aldehydes in amine catalysts or amines by 2,4-dinitrophenylhydrazine derivatization.

    PubMed

    Barman, Bhajendra N

    2014-01-31

    Carbonyl compounds, specifically aldehydes, present in amine catalysts or amines are determined by reversed-phase liquid chromatography using ultraviolet detection of their corresponding 2,4-dinitrophenylhydrazones. The primary focus has been to establish optimum conditions for determining aldehydes accurately because these add exposure concerns when the amine catalysts are used to manufacture polyurethane products. Concentrations of aldehydes determined by this method are found to vary with the pH of the aqueous amine solution and the derivatization time, the latter being problematic when the derivatization reaction proceeds slowly and not to completion in neutral and basic media. Accurate determination of aldehydes in amines through derivatization can be carried out at an effective solution pH of about 2 and with derivatization time of 20min. Hydrochloric acid has been used for neutralization of an amine. For complete derivatization, it is essential to protonate all nitrogen atoms in the amine. An approach for the determination of an adequate amount of acid needed for complete derivatization has been described. Several 0.2M buffer solutions varying in pH from 4 to 8 have also been used to make amine solutions for carrying out derivatization of aldehydes. These solutions have effective pHs of 10 or higher and provide much lower aldehyde concentrations compared to their true values. Mechanisms for the formation of 2,4-dinitrophenylhydrazones in both acidic and basic media are discussed. PMID:24411140

  8. Filtrates & Residues. Acid Pickling with Amines: An Experiment in Applied Chemistry for High School or Freshman Chemistry.

    ERIC Educational Resources Information Center

    Spears, Steven G.; And Others

    1988-01-01

    This article gives a brief description of the process of the removal of corrosion and millscale from the surfaces of ferrous metals by acid pickling. It suggests an experiment to illustrate this process including the procedure and a discussion of the results. (CW)

  9. Inhibitors of the hepatitis C virus NS3 protease with basic amine functionality at the P3-amino acid N-terminus: discovery and optimization of a new series of P2-P4 macrocycles.

    PubMed

    Harper, Steven; Ferrara, Marco; Crescenzi, Benedetta; Pompei, Marco; Palumbi, Maria Cecilia; DiMuzio, Jillian M; Donghi, Monica; Fiore, Fabrizio; Koch, Uwe; Liverton, Nigel J; Pesci, Silvia; Petrocchi, Alessia; Rowley, Michael; Summa, Vincenzo; Gardelli, Cristina

    2009-08-13

    In a follow-up to our recent disclosure of P2-P4 macrocyclic inhibitors of the hepatitis C virus (HCV) NS3 protease (e.g., 1, Chart 1), we report a new but related compound series featuring a basic amine at the N-terminus of the P3-amino acid residue. Replacement of the electroneutral P3-amino acid capping group (which is a feature of almost all tripeptide-like inhibitors of NS3 reported to date) with a basic group is not only tolerated but can result in advantageous cell based potency. Optimization of this new class of P3-amine based inhibitors gave compounds such as 25 and 26 that combine excellent cell based activity with pharmacokinetic properties that are attractive for an antiviral targeting HCV.

  10. Structural and spectroscopic characterizations on the charge-transfer interactions of the second generation poly(propylene amine) dendrimers with iodine and picric acid acceptors

    NASA Astrophysics Data System (ADS)

    El-Sayed, Mohamed Y.; Refat, Moamen S.

    2015-02-01

    Herein, this study was focused to get a knowledge about the intermolecular charge transfer complexes between the second generation of poly(propylene amine) dendrimer (PPD2) with picric acid (PA) and iodine (I2) as π and σ-acceptors. The charge-transfer interaction of the PPD2 electron donor and the PA acceptor has been studied in CHCl3. The resulted data refereed to the formation of the new CT-complex with the general formula [(PPD2)(PA)4]. The 1:4 stoichiometry of the reaction was discussed upon the on elemental analysis and photometric titration. On the other hand, the 1:3½ iodine-PPD2 heptaiodide (I7-) charge-transfer complex has been studied spectrophotometrically in chloroform at room temperature with general formula [(PPD2)]+I7-. The electronic absorption bands of 2I2·I3- (I7-) are observed at 358 and 294 nm. Raman laser spectrum of the brown solid heptaiodide complex has two clearly vibration bands at 155 and 110 cm-1 due to symmetric stretching νs(Isbnd I) outer and inner bonds, respectively. The 1H NMR spectra and differential scanning calorimetry (DSC) data of PPD2 charge-transfer complexes were discussed.

  11. Combining Amine-Reactive Cross-Linkers and Photo-Reactive Amino Acids for 3D-Structure Analysis of Proteins and Protein Complexes.

    PubMed

    Lössl, Philip; Sinz, Andrea

    2016-01-01

    During the last 15 years, the combination of chemical cross-linking and high-resolution mass spectrometry (MS) has matured into an alternative approach for analyzing 3D-structures of proteins and protein complexes. Using the distance constraints imposed by the cross-links, models of the protein or protein complex under investigation can be created. The majority of cross-linking studies are currently conducted with homobifunctional amine-reactive cross-linkers. We extend this "traditional" cross-linking/MS strategy by adding complementary photo-cross-linking data. For this, the diazirine-containing unnatural amino acids photo-leucine and photo-methionine are incorporated into the proteins and cross-link formation is induced by UV-A irradiation. The advantage of the photo-cross-linking strategy is that it is not restricted to lysine residues and that hydrophobic regions in proteins can be targeted, which is advantageous for investigating membrane proteins. We consider the strategy of combining cross-linkers with orthogonal reactivities and distances to be ideally suited for maximizing the amount of structural information that can be gained from a cross-linking experiment.

  12. Dual Catalysis Using Boronic Acid and Chiral Amine: Acyclic Quaternary Carbons via Enantioselective Alkylation of Branched Aldehydes with Allylic Alcohols.

    PubMed

    Mo, Xiaobin; Hall, Dennis G

    2016-08-31

    A ferrocenium boronic acid salt activates allylic alcohols to generate transient carbocations that react with in situ-generated chiral enamines from branched aldehydes. The optimized conditions afford the desired acyclic products embedding a methyl-aryl quaternary carbon center with up to 90% yield and 97:3 enantiomeric ratio, with only water as the byproduct. This noble-metal-free method complements alternative methods that are incompatible with carbon-halogen bonds and other sensitive functional groups. PMID:27518200

  13. Dispersive liquid-liquid microextraction based on amine-functionalized Fe₃O₄ nanoparticles for the determination of phenolic acids in vegetable oils by high-performance liquid chromatography with UV detection.

    PubMed

    Shi, Zhihong; Qiu, Lingna; Zhang, Dan; Sun, Mengyuan; Zhang, Hongyi

    2015-08-01

    A novel dispersive liquid-liquid microextraction method based on amine-functionalized Fe3O4 magnetic nanoparticles was developed for the determination of six phenolic acids in vegetable oils by high-performance liquid chromatography. Amine-functionalized Fe3O4 was synthesized by a one-pot solvothermal reaction between Fe3O4 and 1,6-hexanediamine and characterized by transmission electron microscopy and Fourier transform infrared spectrophotometry. A trace amount of phosphate buffer solution (extractant) was adsorbed on bare Fe3O4-NH2 nanoparticles by hydrophilic interaction to form the "magnetic extractant". Rapid extraction could be achieved while the "magnetic extractant" on amine-functionalized Fe3O4 nanoparticles was dispersed in the sample solution by vortexing. After extraction, the "magnetic extractant" was collected by application of an external magnet. Some important parameters, such as pH and volume of extraction and desorption solvents, the extraction and desorption time needed were carefully investigated and optimized to achieve the best extraction efficiency. Under the optimal conditions, satisfactory extraction recoveries were obtained for the six phenolic acids in the range of 84.2-106.3%. Relative standard deviations for intra- and inter-day precisions were less than 6.3 and 10.0%, respectively. Finally, the established method was successfully applied for the determination of six phenolic acids in eight kinds of vegetable oils. PMID:26109040

  14. Dispersive liquid-liquid microextraction based on amine-functionalized Fe₃O₄ nanoparticles for the determination of phenolic acids in vegetable oils by high-performance liquid chromatography with UV detection.

    PubMed

    Shi, Zhihong; Qiu, Lingna; Zhang, Dan; Sun, Mengyuan; Zhang, Hongyi

    2015-08-01

    A novel dispersive liquid-liquid microextraction method based on amine-functionalized Fe3O4 magnetic nanoparticles was developed for the determination of six phenolic acids in vegetable oils by high-performance liquid chromatography. Amine-functionalized Fe3O4 was synthesized by a one-pot solvothermal reaction between Fe3O4 and 1,6-hexanediamine and characterized by transmission electron microscopy and Fourier transform infrared spectrophotometry. A trace amount of phosphate buffer solution (extractant) was adsorbed on bare Fe3O4-NH2 nanoparticles by hydrophilic interaction to form the "magnetic extractant". Rapid extraction could be achieved while the "magnetic extractant" on amine-functionalized Fe3O4 nanoparticles was dispersed in the sample solution by vortexing. After extraction, the "magnetic extractant" was collected by application of an external magnet. Some important parameters, such as pH and volume of extraction and desorption solvents, the extraction and desorption time needed were carefully investigated and optimized to achieve the best extraction efficiency. Under the optimal conditions, satisfactory extraction recoveries were obtained for the six phenolic acids in the range of 84.2-106.3%. Relative standard deviations for intra- and inter-day precisions were less than 6.3 and 10.0%, respectively. Finally, the established method was successfully applied for the determination of six phenolic acids in eight kinds of vegetable oils.

  15. Studies of a pyridino-crown ether-based chiral stationary phase on the enantioseparation of biogenic chiral aralkylamines and α-amino acid esters by high-performance liquid chromatography.

    PubMed

    Lévai, Sándor; Németh, Tamás; Fődi, Tamás; Kupai, József; Tóth, Tünde; Huszthy, Péter; Balogh, György Tibor

    2015-11-10

    This paper reports the enantioseparation ability of a pyridino-18-crown-6 ether-based chiral stationary phase [(S,S)-CSP-1]. The enantiomeric discrimination of chiral stationary phase (S,S)-CSP-1 was evaluated by HPLC using the mixtures of enantiomers of various protonated primary aralkylamines [1-phenylethylamine hydrogen perchlorate (PEA), 2,3-dihydro-1H-inden-1-amine (1-aminoindan), 2,2'-(1,2-diaminoethane-1,2-diyl) diphenol (HPEN)] and perchlorate salts of α-amino acid esters [alanine benzyl ester (Ala-OBn), phenylalanine benzyl ester (Phe-OBn), phenylalanine methyl ester (Phe-OMe), phenylglycine methyl ester (PhGly-OMe), glutamic acid dibenzyl ester (Glu-diOBn), and valine benzyl ester (Val-OBn)]. The best enantioseparation was achieved in the case of PEA. The high enantioselectivity was rationalized by the strong π-π interaction of the extended π system of the aryl-substituted pyridine unit.

  16. Studies of a pyridino-crown ether-based chiral stationary phase on the enantioseparation of biogenic chiral aralkylamines and α-amino acid esters by high-performance liquid chromatography.

    PubMed

    Lévai, Sándor; Németh, Tamás; Fődi, Tamás; Kupai, József; Tóth, Tünde; Huszthy, Péter; Balogh, György Tibor

    2015-11-10

    This paper reports the enantioseparation ability of a pyridino-18-crown-6 ether-based chiral stationary phase [(S,S)-CSP-1]. The enantiomeric discrimination of chiral stationary phase (S,S)-CSP-1 was evaluated by HPLC using the mixtures of enantiomers of various protonated primary aralkylamines [1-phenylethylamine hydrogen perchlorate (PEA), 2,3-dihydro-1H-inden-1-amine (1-aminoindan), 2,2'-(1,2-diaminoethane-1,2-diyl) diphenol (HPEN)] and perchlorate salts of α-amino acid esters [alanine benzyl ester (Ala-OBn), phenylalanine benzyl ester (Phe-OBn), phenylalanine methyl ester (Phe-OMe), phenylglycine methyl ester (PhGly-OMe), glutamic acid dibenzyl ester (Glu-diOBn), and valine benzyl ester (Val-OBn)]. The best enantioseparation was achieved in the case of PEA. The high enantioselectivity was rationalized by the strong π-π interaction of the extended π system of the aryl-substituted pyridine unit. PMID:26218505

  17. Solvent-extraction and purification of uranium(VI) and molybdenum(VI) by tertiary amines from acid leach solutions

    SciTech Connect

    La Gamma, Ana M.G.; Becquart, Elena T.; Chocron, Mauricio

    2008-07-01

    Considering international interest in the yellow-cake price, Argentina is seeking to exploit new uranium ore bodies and processing plants. A study of similar plants would suggest that solvent- extraction with Alamine 336 is considered the best method for the purification and concentration of uranium present in leaching solutions. In order to study the purification of these leach liquors, solvent-extraction tests under different conditions were performed with simulated solutions which containing molybdenum and molybdenum-uranium mixtures. Preliminary extraction tests carried out on mill acid-leaching liquors are also presented. (authors)

  18. Amine Measurements in Boreal Forest Air

    NASA Astrophysics Data System (ADS)

    Hemmilä, Marja; Hellén, Heidi; Makkonen, Ulla; Hakola, Hannele

    2015-04-01

    Amines are reactive, volatile bases in the air with a general formula of RNH2, R2NH or R3N. Especially small amines can stabilize sulphuric acid clusters and hence affect nucleation. Amines react rapidly with hydroxyl radical (OH˙) thus affecting oxidative capacity of the atmosphere. The amine concentrations are higher in forest air than in urban air (Hellén et al., 2014), but the sources are not known. In order to get more information concerning amine sources, we conducted a measurement campaign in a boreal forest. At SMEAR II station at Hyytiälä, Southern Finland (61°510'N, 24°170'E, 180 m a.s.l.) The measurements cover seven months, from June to December 2014. For sampling and measuring we used MARGA (The instrument for Measuring AeRosols and Gases in Ambient air) which is an on-line ion chromatograph (IC) connected to a sampling system. The IC component of the MARGA system was coupled to an electrospray ionization quadrupole mass spectrometer (MS) to improve sensitivity of amine measurements. This new set-up enabled amine concentration measurements in ambient air both in aerosol and gas phases with a time resolution of only 1 hour. With MARGA-MS we analysed 7 different amines: monomethylamine (MMA), dimethylamine (DMA), trimethylamine (TMA), ethylamine (EA), diethylamine (DEA), propylamine (PA) and butylamine (BA). In preliminary data-analysis we found out, that in June and July most of the measured amines were in gas phase, and particle phase amine concentrations were mostly under detection limits (<1.7 pptv). In June the gaseous amine concentrations were higher than in July. The measured concentrations of gaseous amines followed temperature variation, which could indicate that amines are produced and emitted from the environment or re-emitted from the surfaces as temperature rises after deposition during night-time. All measured amines had similar diurnal variation with maxima during afternoon and minima during night. Results from other months will also

  19. Evaluation of toluene exposure via drinking water on levels of regional brain biogenic monoamines and their metabolites in CD-1 mice

    SciTech Connect

    Hsieh, G.C.; Sharma, R.P.; Parker, R.D.; Coulombe, R.A. Jr. )

    1990-10-01

    Toluene, a potentially neurotoxic substance, is found in trace amounts in groundwater. Adult male CD-1 mice were continuously fed drinking water ad libitum containing 0, 17, 80, and 405 mg/liter toluene. After a 28-day treatment, animals were tested for endogenous levels of the biogenic monoamines norepinephrine (NE), dopamine (DA), and serotonin (5-HT) and their respective metabolites, 3-methoxy-4-hydroxymandelic acid (VMA), 3,4-dihydroxyphenylacetic acid (DOPAC), homovanillic acid (HVA), and 5-hydroxyindoleacetic acid (5-HIAA), in six discrete brain regions. The maximum toluene-induced increases of biogenic amines and their metabolites generally occurred at a toluene concentration of 80 mg/liter. In the hypothalamus, a major NE-containing compartment, the concentrations of NE significantly increased by 51, 63, and 34% in groups dosed with 17, 80, and 405 mg/liter, respectively. Significant increases of NE were also observed in the medulla oblongata and midbrain. Concomitantly, concentrations of VMA increased in various brain regions. Concentrations of DA were significantly higher in the corpus striatum and hypothalamus. Alterations in levels of DA metabolites, DOPAC and HVA, were marginal. Toluene significantly increased concentrations of 5-HT in all dissected brain regions, except cerebellum, and increased the 5-HIAA levels in the hypothalamus, corpus striatum, and cerebral cortex.

  20. Two coordination polymers constructed from a multidentate carboxylic acid ligand with a tertiary amine serve as acid-base catalysts for the synthesis of chloropropene carbonate from CO2 under atmospheric pressure.

    PubMed

    Chen, Chao; Zhang, Jun; Li, Guanghua; Shen, Pan; Jin, Haichao; Zhang, Ning

    2014-10-01

    Two new coordination polymers, [Ni(H2O)(Hpdcd)(H2O)2]·DMF (1) and [Co(H2O)(Hpdcd)(H2O)2]·DMF (2) (H3pdcd = 1-(4-carboxyphenyl)-2,5-dimethyl, 1H-pyrrole-3,4-dicarboxylic acid), which were designed based on a tertiary amine ligand, were synthesized and characterized using multiple spectroscopy techniques, including single-crystal X-ray diffraction. These two 1D linear chains possess the properties of both a Lewis acid and organic base, which was confirmed by temperature programmed desorption of ammonia and on-line mass spectrometry (NH3-TPD-MS), and selective sorption for carbon dioxide. Due to their acid-base properties, the compounds exhibited high catalytic activity, in the absence of co-catalysts, for solvent-free synthesis of chloropropene carbonate from CO2 and epichlorohydrin under atmospheric CO2 pressure. The yields of chloropropene carbonate were 88% and 87% for 1 and 2, respectively, under the optimized conditions. PMID:25113602

  1. The Moon: Biogenic elements

    NASA Technical Reports Server (NTRS)

    Gibson, Everett K., Jr.; Chang, Sherwood

    1992-01-01

    The specific objectives of the organic chemical exploration of the Moon involve the search for molecules of possible biological or prebiological origin. Detailed knowledge of the amount, distribution, and exact structure of organic compounds present on the Moon is extremely important to our understanding of the origin and history of the Moon and to its relationship to the history of the Earth and solar system. Specifically, such knowledge is essential for determining whether life on the Moon exists, ever did exist, or could develop. In the absence of life or organic matter, it is still essential to determine the abundance, distribution, and origin of the biogenic elements (e.g., H, C, O, N, S, P) in order to understand how the planetary environment may have influenced the course of chemical evolution. The history and scope of this effort is presented.

  2. Biogenic Impact on Materials

    NASA Astrophysics Data System (ADS)

    Stephan, Ina; Askew, Peter D.; Gorbushina, Anna A.; Grinda, Manfred; Hertel, Horst; Krumbein, Wolfgang E.; Müller, Rolf-Joachim; Pantke, Michael; Plarre, Rüdiger (Rudy); Schmitt, Guenter; Schwibbert, Karin

    Materials as constituents of products or components of technical systems rarely exist in isolation and many must cope with exposure in the natural world. This chapter describes methods that simulate how a material is influenced through contact with living systems such as microorganisms and arthropods. Both unwanted and desirable interactions are considered. This biogenic impact on materials is intimately associated with the environment to which the material is exposed (Materials-Environment Interaction, Chap. 15). Factors such as moisture, temperature and availability of food sources all have a significant influence on biological systems. Corrosion (Chap. 12) and wear (Chap. 13) can also be induced or enhanced in the presence of microorganisms. Section 14.1 introduces the categories between desired (biodegradation) and undesired (biodeterioration) biological effects on materials. It also introduces the role of biocides for the protection of materials. Section 14.2 describes the testing of wood as a building material especially against microorganisms and insects. Section 14.3 characterizes the test methodologies for two other groups of organic materials, namely polymers (Sect. 14.3.1) and paper and textiles (Sect. 14.3.2). Section 14.4 deals with the susceptibility of inorganic materials such as metals (Sect. 14.4.1), concrete (Sect. 14.4.2) and ceramics (Sect. 14.4.3) to biogenic impact. Section 14.5 treats the testing methodology concerned with the performance of coatings and coating materials. In many of these tests specific strains of organisms are employed. It is vital that these strains retain their ability to utilize/attack the substrate from which they were isolated, even when kept for many years in the laboratory. Section 14.6 therefore considers the importance of maintaining robust and representative test organisms that are as capable of utilizing a substrate as their counterparts in nature such that realistic predictions of performance can be made.

  3. Biogenic inputs to ocean mixing.

    PubMed

    Katija, Kakani

    2012-03-15

    Recent studies have evoked heated debate about whether biologically generated (or biogenic) fluid disturbances affect mixing in the ocean. Estimates of biogenic inputs have shown that their contribution to ocean mixing is of the same order as winds and tides. Although these estimates are intriguing, further study using theoretical, numerical and experimental techniques is required to obtain conclusive evidence of biogenic mixing in the ocean. Biogenic ocean mixing is a complex problem that requires detailed understanding of: (1) marine organism behavior and characteristics (i.e. swimming dynamics, abundance and migratory behavior), (2) mechanisms utilized by swimming animals that have the ability to mix stratified fluids (i.e. turbulence and fluid drift) and (3) knowledge of the physical environment to isolate contributions of marine organisms from other sources of mixing. In addition to summarizing prior work addressing the points above, observations on the effect of animal swimming mode and body morphology on biogenic fluid transport will also be presented. It is argued that to inform the debate on whether biogenic mixing can contribute to ocean mixing, our studies should focus on diel vertical migrators that traverse stratified waters of the upper pycnocline. Based on our understanding of mixing mechanisms, body morphologies, swimming modes and body orientation, combined with our knowledge of vertically migrating populations of animals, it is likely that copepods, krill and some species of gelatinous zooplankton and fish have the potential to be strong sources of biogenic mixing. PMID:22357597

  4. Fermented functional foods based on probiotics and their biogenic metabolites.

    PubMed

    Stanton, Catherine; Ross, R Paul; Fitzgerald, Gerald F; Van Sinderen, Douwe

    2005-04-01

    The claimed health benefits of fermented functional foods are expressed either directly through the interaction of ingested live microorganisms, bacteria or yeast with the host (probiotic effect) or indirectly as a result of ingestion of microbial metabolites produced during the fermentation process (biogenic effect). Although still far from fully understood, several probiotic mechanisms of action have been proposed, including competitive exclusion, competition for nutrients and/or stimulation of an immune response. The biogenic properties of fermented functional foods result from the microbial production of bioactive metabolites such as certain vitamins, bioactive peptides, organic acids or fatty acids during fermentation.

  5. Amine-containing cells of the lung.

    PubMed

    Pack, R J; Widdicombe, J G

    1984-11-01

    In many vertebrates, including mammals, there are amine-containing cells in the walls of the airways and the lungs. Despite a plethora of names for these cells, there is a general agreement about their structure. They occur singly or in groups (NEBs), but the functional distinction between the two types of distribution is uncertain. In spite of ultrastructural similarities, the cells may be physiologically heterogenous. The cells are characterised by their staining characteristics and content of electron-dense-core vesicles, which are believed to contain a biogenic amine. They also have additional cytoplasmic features common to other sensory paraganglia. They may be more numerous in certain species and also in the neonate. The NEBs may be innervated with afferent and/or efferent nerves, though physiological evidence of their innervation is scanty. The most popular hypothesis is that they can be stimulated by hypoxia to release mediators or to induce reflex activity. In the healthy animal, the amine-cells may control local ventilation/perfusion (V/Q) ratios via an action on the pulmonary vasculature. In disease, they may cause pulmonary hypertension. They can also give rise to three forms of tumour. Their full significance has yet to be established. PMID:6083878

  6. Trace amine-associated receptors and their ligands

    PubMed Central

    Zucchi, R; Chiellini, G; Scanlan, T S; Grandy, D K

    2006-01-01

    Classical biogenic amines (adrenaline, noradrenaline, dopamine, serotonin and histamine) interact with specific families of G protein-coupled receptors (GPCRs). The term ‘trace amines' is used when referring to p-tyramine, β-phenylethylamine, tryptamine and octopamine, compounds that are present in mammalian tissues at very low (nanomolar) concentrations. The pharmacological effects of trace amines are usually attributed to their interference with the aminergic pathways, but in 2001 a new gene was identified, that codes for a GPCR responding to p-tyramine and β-phenylethylamine but not to classical biogenic amines. Several closely related genes were subsequently identified and designated as the trace amine-associated receptors (TAARs). Pharmacological investigations in vitro show that many TAAR subtypes may not respond to p-tyramine, β-phenylethylamine, tryptamine or octopamine, suggesting the existence of additional endogenous ligands. A novel endogenous thyroid hormone derivative, 3-iodothyronamine, has been found to interact with TAAR1 and possibly other TAAR subtypes. In vivo, micromolar concentrations of 3-iodothyronamine determine functional effects which are opposite to those produced on a longer time scale by thyroid hormones, including reduction in body temperature and decrease in cardiac contractility. Expression of all TAAR subtypes except TAAR1 has been reported in mouse olfactory epithelium, and several volatile amines were shown to interact with specific TAAR subtypes. In addition, there is evidence that TAAR1 is targeted by amphetamines and other psychotropic agents, while genetic linkage studies show a significant association between the TAAR gene family locus and susceptibility to schizophrenia or bipolar affective disorder. PMID:17088868

  7. Complexation des acides aminés basiques arginine, histidine et lysine avec l'ADN plasmidique en solution aqueuse : participation à la capture de radicaux sous irradiation X à 1,5 keV

    NASA Astrophysics Data System (ADS)

    Tariq Khalil, Talat; Taillefumier, Baptiste; Boulanouar, Omar; Mavon, Christophe; Fromm, Michel

    2016-09-01

    L'environnement chimique de l'ADN en situation biologique est complexe notam-ment en raison de la présence d'histones, protéines nucléaires, associées en quantité approximativement égales à l'ADN pour former la chromatine. Les histones possèdent de nombreux radicaux basiques arginine et lysine chargés positivement et dont la majorité se trouve sur les chaînes émergentes, l'ADN présente quant à lui des charges négatives sur ses groupements phosphates localisés tout au long de la double hélice. Dans cette étude, la complexité de la structure de la chromatine nucléaire est dans un premier temps mimée en solution aqueuse par la formation de complexes entre un ADN plasmidique sonde et les trois acides aminés basiques, Arg, His, Lys, qui, mis à part His, sont protonés au pH physiologique. Ces acides aminés libres en solution sont réputés être des capteurs efficaces de radicaux libres, notamment pour le radical hydroxyle, conférant ainsi un pouvoir protecteur vis-à-vis des effets indirects sur l'ADN en situation d'exposition aux rayonnements ionisants. A concentration fixée, les capacités de capture des acides aminés libres, σ, pour le radical hydroxyle sont typiquement les suivantes σHis ≈σArg > σLys (σLys ≈ 0,1 × σArg). Nous avons mesuré les taux de cassures simple brin par plasmide et par Gray (χ) lors d'expositions de solutions aqueuses de complexes [acide aminé - ADN plasmidique] aux rayons X ultra-mous (1,5 keV). A concentrations égales, les trois acides aminés complexés et présents en large excès ne manifestent pas une capacité de protection de l'ADN proportionnelle à leur capacité de capture libre et en solution ; on trouve en effet des taux de cassures dans l'ordre suivant χHis > χArg > χLys (χLys ≈ 0,01 χArg). Après avoir détaillé le mode opératoire de ces mesures, nous analyserons sur des bases bibliographiques, les modes spécifiques d'interaction des acides aminés basiques avec l'ADN. La sp

  8. The biogenic approach to cognition.

    PubMed

    Lyon, Pamela

    2006-03-01

    After half a century of cognitive revolution we remain far from agreement about what cognition is and what cognition does. It was once thought that these questions could wait until the data were in. Today there is a mountain of data, but no way of making sense of it. The time for tackling the fundamental issues has arrived. The biogenic approach to cognition is introduced not as a solution but as a means of approaching the issues. The traditional, and still predominant, methodological stance in cognitive inquiry is what I call the anthropogenic approach: assume human cognition as the paradigm and work 'down' to a more general explanatory concept. The biogenic approach, on the other hand, starts with the facts of biology as the basis for theorizing and works 'up' to the human case by asking psychological questions as if they were biological questions. Biogenic explanations of cognition are currently clustered around two main frameworks for understanding biology: self-organizing complex systems and autopoiesis. The paper describes the frameworks and infers from them ten empirical principles--the biogenic 'family traits'--that constitute constraints on biogenic theorizing. Because the anthropogenic approach to cognition is not constrained empirically to the same degree, I argue that the biogenic approach is superior for approaching a general theory of cognition as a natural phenomenon.

  9. o-Iodoxybenzoic acid (IBX) as a viable reagent in the manipulation of nitrogen- and sulfur-containing substrates: scope, generality, and mechanism of IBX-mediated amine oxidations and dithiane deprotections.

    PubMed

    Nicolaou, K C; Mathison, Casey J N; Montagnon, Tamsyn

    2004-04-28

    o-Iodoxybenzoic acid (IBX), a highly versatile hypervalent iodine(V) reagent, was found to efficiently mediate the dehydrogenation of amines in addition to facilitating the oxidative cleavage of dithioacetals and dithioketals. Through the development of relevant IBX-based protocols, a plethora of useful synthetic intermediates, including imines, oximes, ketones, and aromatic N-heterocycles, were found to be readily accessible under notably mild conditions. Further investigation of these transformations led to the elucidation of valuable mechanistic details, resulting in the conclusion that they proceed via ionic rather than single electron transfer (SET) pathways.

  10. Evolutionary Conservation of 3-Iodothyronamine as an Agonist at the Trace Amine-Associated Receptor 1

    PubMed Central

    Cöster, Maxi; Biebermann, Heike; Schöneberg, Torsten; Stäubert, Claudia

    2015-01-01

    Objectives The trace amine-associated receptor 1 (Taar1) is a Gs protein-coupled receptor activated by trace amines, such as β-phenylethylamine (β-PEA) and 3-iodothyronamine (T1AM). T1AM is an endogenous biogenic amine and thyroid hormone derivative that exerts several biological functions. However, the physiological relevance of T1AM acting via Taar1 is still under discussion. Therefore, we studied the structural and functional evolution of Taar1 in vertebrates to provide evidence for a conserved Taar1-mediated T1AM function. Study Design We searched public sequence databases to retrieve Taar1 sequence information from vertebrates. We cloned and functionally characterized Taar1 from selected vertebrate species using cAMP assays to determine the evolutionary conservation of T1AM action at Taar1. Results We found intact open reading frames of Taar1 in more than 100 vertebrate species, including mammals, sauropsids and amphibians. Evolutionary conservation analyses of Taar1 protein sequences revealed a high variation in amino acid residues proposed to be involved in agonist binding, especially in rodent Taar1 orthologs. Functional characterization showed that T1AM, β-PEA and p-tyramine (p-Tyr) act as agonists at all tested orthologs, but EC50 values of T1AM at rat Taar1 differed significantly when compared to all other tested vertebrate Taar1. Conclusions The high structural conservation of Taar1 throughout vertebrate evolution highlights the physiological relevance of Taar1, but species-specific differences in T1AM potency at Taar1 orthologs suggest a specialization of rat Taar1 for T1AM recognition. In contrast, β-PEA and p-Tyr potencies were rather conserved throughout all tested Taar1 orthologs. We provide evidence that the observed differences in potency are related to differences in constraint during Taar1 evolution. PMID:26601069

  11. Hydropower's Biogenic Carbon Footprint.

    PubMed

    Scherer, Laura; Pfister, Stephan

    2016-01-01

    Global warming is accelerating and the world urgently needs a shift to clean and renewable energy. Hydropower is currently the largest renewable source of electricity, but its contribution to climate change mitigation is not yet fully understood. Hydroelectric reservoirs are a source of biogenic greenhouse gases and in individual cases can reach the same emission rates as thermal power plants. Little is known about the severity of their emissions at the global scale. Here we show that the carbon footprint of hydropower is far higher than previously assumed, with a global average of 173 kg CO2 and 2.95 kg CH4 emitted per MWh of electricity produced. This results in a combined average carbon footprint of 273 kg CO2e/MWh when using the global warming potential over a time horizon of 100 years (GWP100). Nonetheless, this is still below that of fossil energy sources without the use of carbon capture and sequestration technologies. We identified the dams most promising for capturing methane for use as alternative energy source. The spread among the ~1500 hydropower plants analysed in this study is large and highlights the importance of case-by-case examinations. PMID:27626943

  12. Hydropower's Biogenic Carbon Footprint

    PubMed Central

    Pfister, Stephan

    2016-01-01

    Global warming is accelerating and the world urgently needs a shift to clean and renewable energy. Hydropower is currently the largest renewable source of electricity, but its contribution to climate change mitigation is not yet fully understood. Hydroelectric reservoirs are a source of biogenic greenhouse gases and in individual cases can reach the same emission rates as thermal power plants. Little is known about the severity of their emissions at the global scale. Here we show that the carbon footprint of hydropower is far higher than previously assumed, with a global average of 173 kg CO2 and 2.95 kg CH4 emitted per MWh of electricity produced. This results in a combined average carbon footprint of 273 kg CO2e/MWh when using the global warming potential over a time horizon of 100 years (GWP100). Nonetheless, this is still below that of fossil energy sources without the use of carbon capture and sequestration technologies. We identified the dams most promising for capturing methane for use as alternative energy source. The spread among the ~1500 hydropower plants analysed in this study is large and highlights the importance of case-by-case examinations. PMID:27626943

  13. Hydropower's Biogenic Carbon Footprint.

    PubMed

    Scherer, Laura; Pfister, Stephan

    2016-01-01

    Global warming is accelerating and the world urgently needs a shift to clean and renewable energy. Hydropower is currently the largest renewable source of electricity, but its contribution to climate change mitigation is not yet fully understood. Hydroelectric reservoirs are a source of biogenic greenhouse gases and in individual cases can reach the same emission rates as thermal power plants. Little is known about the severity of their emissions at the global scale. Here we show that the carbon footprint of hydropower is far higher than previously assumed, with a global average of 173 kg CO2 and 2.95 kg CH4 emitted per MWh of electricity produced. This results in a combined average carbon footprint of 273 kg CO2e/MWh when using the global warming potential over a time horizon of 100 years (GWP100). Nonetheless, this is still below that of fossil energy sources without the use of carbon capture and sequestration technologies. We identified the dams most promising for capturing methane for use as alternative energy source. The spread among the ~1500 hydropower plants analysed in this study is large and highlights the importance of case-by-case examinations.

  14. Separation of biogenic and biomass burning submicron aerosol from a boreal forest in Hyytiälä, Finland during HUMPPA-COPEC 2010

    NASA Astrophysics Data System (ADS)

    Corrigan, A.; Russell, L.; Äijälä, M.; Petäjä, T.; Kulmala, M.; Song, W.; Williams, J.

    2012-04-01

    Forests play an important role in the emission of primary and secondary organic aerosol (POA, SOA). Biomass burning is believed to be the largest source of global primary organic carbon (POC), estimated to be 31-45 TgC yr-1 [1]. In addition, biogenic volatile organic compounds (BVOCs) produce a large portion of global SOA, as BVOC emissions are believed to be 10 times greater than anthropogenic VOC emissions [2]. The oxidation of BVOCs produces considerable amounts of SOA, 12-70 TgC yr-1 [3]. In addition, the influence of anthropogenic emissions (i.e. NOx) can substantially enhance biogenic SOA formation [4]. Due to large uncertainties in the role aerosols play in the climate sysyen, there is a need to better understand the chemical composition of organic aerosols derived from forest ecosystems. One approach to better understand the composition and contribution of biogenic derived organic aerosols is to apply Positive Matrix Facotrization (PMF) on a time series dataset [5]. Due to chemical similarity and multi-collinerarity, separation of biogenic and biomass burning aerosol in boreal forests has been problematic in previous work [6]. To investigate the composition and sources of atmospheric aerosol in a biogenically influenced site, submicron particles were collected from July 12 to August 12, 2010 at the boreal forest in Hyytiälä, Finland and analyzed using Fourier transform infrared (FTIR) spectroscopy and aerosol mass spectrometry (AMS). Campaign average organic functional groups from FTIR analysis of submicron aerosol includes alkane (37%), carboxylic acid (28%), organic hydroxyl (15%), non-carboxylic acid carbonyl (15%), and primary amine (5%), with traces of organonitrate and organosulphates. AMS analysis indicates that the aerosol composition was heavily dominated by organics (69%), followed by sulphate (21%), nitrate (6%), and ammonia (4%). Measurements of particle-phase organic functional groups and inorganic ions collected during the HUMPPA-COPEC10

  15. [Bounds of change in unsaturation index of fatty acid composition of phospholipids at adaptation of molluscs to biogenic and abiogenic factors of external medium].

    PubMed

    Chebotareva, M A; Zabelinskiĭ, S A; Shukoliukova, E P; Krivchenko, A I

    2011-01-01

    Comparative study of fatty acid composition of total phospholipids, as well as of phosphatidylcholine and phosphatidylethanolamine from hepatopancreas and leg muscle was performed on several representatives of gasteropods (Gastropoda) molluscs and bivalve (Bivalvia) mussel (Mytilus edulus). The objects of our study were marine litorins (Littorina saxsatilis) adapted to different temperature conditions of White Sea and Barents Sea, freshwater lymnaea (Lymnaea stagnalis) infested by Trematoda and mussels from White Sea and Black Sea. It was shown that depending on the existence conditions of studied tissue or lipid, the maximal change is observed in the percentage of saturated acids (4-83 %), the percentage of unsaturated acids was less expressed (1-14 %) and the changes in unsaturation index (UI) did not exceed 20 % on average. It was supposed that observed quantitative bounds of UI change under the action of different external factors is utmost for maintenance of membrane fluidity necessary for normal vital activity of cell, particularly in studied ectothermic molluscs. PMID:22145319

  16. Amine salts of nitroazoles

    DOEpatents

    Kienyin Lee; Stinecipher, M.M.

    1993-10-26

    Compositions of matter, a method of providing chemical energy by burning said compositions, and methods of making said compositions are described. These compositions are amine salts of nitroazoles. 1 figure.

  17. A general method for N-methylation of amines and nitro compounds with dimethylsulfoxide.

    PubMed

    Jiang, Xue; Wang, Chao; Wei, Yawen; Xue, Dong; Liu, Zhaotie; Xiao, Jianliang

    2014-01-01

    DMSO methylates a broad range of amines in the presence of formic acid, providing a novel, green and practical method for amine methylation. The protocol also allows the one-pot transformation of aromatic nitro compounds into dimethylated amines in the presence of a simple iron catalyst.

  18. Dietary Phenolic Compounds Interfere with the Fate of Hydrogen Peroxide in Human Adipose Tissue but Do Not Directly Inhibit Primary Amine Oxidase Activity

    PubMed Central

    Carpéné, Christian; Hasnaoui, Mounia; Balogh, Balázs; Matyus, Peter; Fernández-Quintela, Alfredo; Rodríguez, Víctor; Mercader, Josep; Portillo, Maria P.

    2016-01-01

    Resveratrol has been reported to inhibit monoamine oxidases (MAO). Many substrates or inhibitors of neuronal MAO interact also with other amine oxidases (AO) in peripheral organs, such as semicarbazide-sensitive AO (SSAO), known as primary amine oxidase, absent in neurones, but abundant in adipocytes. We asked whether phenolic compounds (resveratrol, pterostilbene, quercetin, and caffeic acid) behave as MAO and SSAO inhibitors. AO activity was determined in human adipose tissue. Computational docking and glucose uptake assays were performed in 3D models of human AO proteins and in adipocytes, respectively. Phenolic compounds fully inhibited the fluorescent detection of H2O2 generated during MAO and SSAO activation by tyramine and benzylamine. They also quenched H2O2-induced fluorescence in absence of biological material and were unable to abolish the oxidation of radiolabelled tyramine and benzylamine. Thus, phenolic compounds hampered H2O2 detection but did not block AO activity. Only resveratrol and quercetin partially impaired MAO-dependent [14C]-tyramine oxidation and behaved as MAO inhibitors. Phenolic compounds counteracted the H2O2-dependent benzylamine-stimulated glucose transport. This indicates that various phenolic compounds block downstream effects of H2O2 produced by biogenic or exogenous amine oxidation without directly inhibiting AO. Phenolic compounds remain of interest regarding their capacity to limit oxidative stress rather than inhibiting AO. PMID:26881018

  19. Application of BTEX/amine VLE data at Hanlan Robb Gas Plant

    SciTech Connect

    Hegarty, M.; Hawthorne, D.

    1999-07-01

    The Hanlan Robb Gas Plant has suffered from rapid sulfur plant catalyst deactivation due to fouling of the catalyst beds by aromatics. The aromatics originate in the inlet gas, are absorbed by the circulating amine, and are released to the acid gas stream during amine regeneration. Key factors that affect sulfur catalyst deactivation are the amount of aromatics absorbed in the amine plant and the efficiency of aromatic destruction in the reaction furnace. The criteria and techniques employed at Hanlan Robb for attaining adequate aromatic destruction in the reaction furnace are presented. The GPA has recently sponsored a project to determine aromatic solubility in various amines. These data will be used to develop amine models that will be capable of optimizing the amine plant for minimal aromatic absorption. Solubility measurements by Armines-Ecole des Mines de Paris indicate that the solubility of BTEX in aqueous amines increases substantially as the molar concentration of the amine increases. Predictions of aromatic absorption in the amine plant based on the interim data indicate that there is no strong effect of MDEA concentration on the percentage of BTEX absorbed in the contactor until approximately 45% wt NDEA. Above this concentration, the tendency of the amine to absorb BTEX appears to increase steadily. Operation at high rich amine loadings minimizes the amount of aromatics absorbed. The amine flash drum is not effective in removing BTEX from the rich amine. A rich amine gas stripper requires a significant amount of stripping gas to be effective.

  20. CCN activity of aliphatic amine secondary aerosol

    NASA Astrophysics Data System (ADS)

    Tang, X.; Price, D.; Praske, E.; Vu, D.; Purvis-Roberts, K.; Silva, P. J.; Cocker, D. R., III; Asa-Awuku, A.

    2014-01-01

    Aliphatic amines can form secondary aerosol via oxidation with atmospheric radicals (e.g. hydroxyl radical and nitrate radical). The particle composition can contain both secondary organic aerosol (SOA) and inorganic salts. The fraction of organic to inorganic materials in the particulate phase influences aerosol hygroscopicity and cloud condensation nuclei (CCN) activity. SOA formed from trimethylamine (TMA) and butylamine (BA) reactions with hydroxyl radical (OH) is composed of organic material of low hygroscopicity (single hygroscopicity parameter, κ ≤ 0.25). Secondary aerosol formed from the tertiary aliphatic amine (TMA) with N2O5 (source of nitrate radical, NO3), contains less volatile compounds than the primary aliphatic amine (BA) aerosol. TMA + N2O5 form semi-volatile organics in low RH conditions that have κ ~ 0.20, indicative of slightly soluble organic material. As RH increases, several inorganic amine salts are formed as a result of acid-base reactions. The CCN activity of the humid TMA-N2O5 aerosol obeys Zdanovskii, Stokes, and Robinson (ZSR) ideal mixing rules. Higher CCN activity (κ > 0.3) was also observed for humid BA+N2O5 aerosols compared with dry aerosol (κ ~ 0.2), as a result of the formation of inorganic salts such as NH4NO3 and butylamine nitrate (C4H11N · HNO3). Compared with TMA, BA+N2O5 reactions produce more volatile aerosols. The BA+N2O5 aerosol products under humid experiments were found to be very sensitive to the temperature within the stream-wise continuous flow thermal gradient CCN counter. The CCN counter, when set above a 21 °C temperature difference, evaporates BA+N2O5 aerosol formed at RH ≥ 30%; κ ranges from 0.4 to 0.7 and is dependent on the instrument supersaturation (ss) settings. The aerosol behaves non-ideally, hence simple ZSR rules cannot be applied to the CCN results from the primary aliphatic amine system. Overall, aliphatic amine aerosol systems κ ranges from 0.2 < κ < 0.7. This work indicates that

  1. IMPROVING BIOGENIC EMISSION ESTIMATES WITH SATELLITE IMAGERY

    EPA Science Inventory

    This presentation will review how existing and future applications of satellite imagery can improve the accuracy of biogenic emission estimates. Existing applications of satellite imagery to biogenic emission estimates have focused on characterizing land cover. Vegetation dat...

  2. Dispersant additives derived from lactone modified amido-amine adducts

    SciTech Connect

    Gutierrez, A.; Lundberg, R.D.

    1990-10-16

    This patent describes a lactone modified dispersant additive. It comprises one adduct of a polyolefin of 300 to 10,000 number average molecular weight substituted with at least 0.8 (e.g., from about 1 to 4) dicarboxylic acid producing moieties (preferably acid or anhydride moieties) per polyolefin molecule, an amido-amine or thioamido-amine characterized by being a reaction product of at least a polyamine and an alpha, beta-unsaturated compound.

  3. Biologically active amines in fermented and non-fermented commercial soybean products from the Spanish market.

    PubMed

    Toro-Funes, N; Bosch-Fuste, J; Latorre-Moratalla, M L; Veciana-Nogués, M T; Vidal-Carou, M C

    2015-04-15

    Biologically active amines were determined in commercial soybean products. The antioxidant polyamines were found in both non-fermented and fermented soybean products. Natto and tempeh showed the highest content of polyamines (75-124 and 11-24 mg/kg of spermidine and spermine, respectively). On the other hand, the bacterial-related biogenic amines, tyramine, histamine, tryptamine and β-phenylethylamine, were detected in practically all fermented products with a high variability. The highest contents were found in sufu, tamari and soybean paste. Extremely high tyramine and histamine contents, 1700 and 700 mg/kg, respectively, found in some sufu samples could be unhealthy. However, biogenic amines observed in the other soybean products should not be a risk for healthy consumers. However, individuals who take monoamine and diamine oxidase inhibitors drugs should be strongly recommended to avoid this kind of products in order to suffer no adverse health effects. These biogenic amines were not detected in non-fermented soybean products.

  4. Aromatic amines and cancer.

    PubMed

    Vineis, P; Pirastu, R

    1997-05-01

    Epidemiological evidence on the relation between aromatic amines and cancer risk is reviewed. In particular, cancer risk in humans resulting from exposure to aromatic amines from occupational sources and tobacco smoking is assessed with reference to ecologic, cohort, and case-control studies. Seven arylamines have been classified by the International Agency for Research on Cancer: benzidine-based dyes and MOCA (4,4'-methylene bis 2-choloroaniline) were considered 'probably' carcinogenic, Group 2A, because of a high level of evidence in experimental animals; two occupational chemicals (2-naphthylamine and benzidine), one drug (Chlornaphazine), and two manufacturing processes (manufacture of auramine and magenta) were included in Group 1 on the basis of 'sufficient' evidence of carcinogenicity in humans. Occupational exposures to aromatic amines explain up to 25 percent of bladder cancers in some areas of Western countries; these estimates might be higher in limited areas of developing countries. Aromatic amines contaminate the ambient air as a component of environmental tobacco smoke. There is increasing evidence that the excess of bladder cancer in smokers is attributable to aromatic amines rather than to other contaminants of tobacco smoke such as polycyclic aromatic hydrocarbons (PAH). A modulating role in the risk of bladder cancer associated with exposure to aromatic amines is played by metabolic polymorphisms, such as the N-acetyltransferase genotype, raising important social and ethical issues. The consistent observation of a difference between men and women in bladder cancer risk, after allowing for known risk factors, suggests consideration of gender-related biological determinants for future investigation.

  5. [Modifications of cerebral amine metabolism in psychiatric illness].

    PubMed

    Linkowski, P; Mendlewicz, J

    1980-01-01

    Abnormalities in brain monoamines have been implicated in the pathogenesis of several psychiatric disorders. A brief revue of biochemical studies on indolamines and catecholamines in mental disorders with special emphasis on endogenous depression will be presented. Progress in neurochemistry makes it possible to investigate the biochemical disturbances present in the major psychoses. Recent knowledge in the neuropharmacological mechanism of action of psychotropic drugs have shed some light on the basic understanding of the pharmacological treatment of psychotic disorders. The implication of biogenic amine studies in psychiatry for endocrinological research in mental disorders will also be discussed.

  6. High capacity immobilized amine sorbents

    DOEpatents

    Gray, McMahan L.; Champagne, Kenneth J.; Soong, Yee; Filburn, Thomas

    2007-10-30

    A method is provided for making low-cost CO.sub.2 sorbents that can be used in large-scale gas-solid processes. The improved method entails treating an amine to increase the number of secondary amine groups and impregnating the amine in a porous solid support. The method increases the CO.sub.2 capture capacity and decreases the cost of utilizing an amine-enriched solid sorbent in CO.sub.2 capture systems.

  7. Oxygen uptake upon photolysis of 1,4-benzoquinones and 1,4-naphthoquinones in air-saturated aqueous solution in the presence of formate, amines, ascorbic acid, and alcohols.

    PubMed

    Görner, Helmut

    2007-04-19

    The effects of oxygen in the photoreduction of 1,4-benzoquinone (BQ), 1,4-naphthoquinone (NQ), and a series of derivatives were studied in aqueous solution in the presence of acetonitrile and formate, aliphatic amines, e.g., EDTA or triethylamine, ascorbic acid, and alcohols, e.g., methanol or 2-propanol. The quinone triplet state is quenched, whereby the semiquinone and donor radicals are formed which react subsequently with oxygen. The overall reaction is oxidation of the donors and conversion of oxygen via the hydroperoxyl/superoxide radical into hydrogen peroxide. The quantum yield (Phi-O2) of this oxygen uptake changes in 2-propanol-water (1:10) from <0.01 for BQ to Phi-O2 = 0.5-0.8 for NQ. Generally Phi-O2 increases with increasing donor concentration. The specific properties of quinone structure, the radical equilibria and reactivity, and the concentration dependences are discussed. PMID:17388578

  8. Evaluation of amine inhibitors for suitability as crevice buffering agents. Final report

    SciTech Connect

    Jayaweera, P.; Hettiarachchi, S.

    1994-03-01

    This report describes the results of a research effort to evaluate the suitability of some selected amines and amino acids as a crevice-buffering agents in pressurized water reactor (PWR) steam generators. The amines may be useful for buffering acid crevices, and the amino acids, because they contain both acidic and basic groups, may be useful for acidic and caustic crevices. Five commercially available amines and two amino acids were studied during this research. The study involved (1) the hydrolysis of these commercially available amines and amino acids, including measurement of their kinetics of decomposition, in simulated steam generator bulk water at 290 C, and (2) determination of their thermal stability in a simulated crevice environment. The study showed that, although the high-molecular-weight amines undergo hydrothermal decomposition, they have a better buffering capacity than their low-molecular-weight counterparts at 290 C. The amines provide effective crevice buffering by increasing the pH of the crevice solution by as much as 2.84 and to 4.24 units in the experimental setup used in this program. It was concluded that polyamines provide excellent buffering of the simulated crevice environment at 290 C and morpholine remains the best low-molecular-weight amine investigated. However, detailed volatility studies of the amines were not considered in this work. Such data would be needed before in-plant testing to ensure that the amines can concentrate in steam generator crevices to the levels assumed in this study.

  9. Linking biogenic hydrocarbons to biogenic aerosol in the Borneo rainforest

    NASA Astrophysics Data System (ADS)

    Hamilton, J. F.; Alfarra, M. R.; Robinson, N.; Ward, M. W.; Lewis, A. C.; McFiggans, G. B.; Coe, H.; Allan, J. D.

    2013-11-01

    Emissions of biogenic volatile organic compounds are though to contribute significantly to secondary organic aerosol formation in the tropics, but understanding these transformation processes has proved difficult, due to the complexity of the chemistry involved and very low concentrations. Aerosols from above a Southeast Asian tropical rainforest in Borneo were characterised using liquid chromatography-ion trap mass spectrometry, high-resolution aerosol mass spectrometry and Fourier transform ion cyclotron resonance mass spectrometry (FTICRMS) techniques. Oxygenated compounds were identified in ambient organic aerosol that could be directly traced back to isoprene, monoterpenes and sesquiterpene emissions, by combining field data on chemical structures with mass spectral data generated from synthetically produced products created in a simulation chamber. Eighteen oxygenated species of biogenic origin were identified in the rainforest aerosol from the precursors isoprene, α-pinene, limonene, α-terpinene and β-caryophyllene. The observations provide the unambiguous field detection of monoterpene and sesquiterpene oxidation products in SOA above a pristine tropical rainforest. The presence of 2-methyl tetrol organosulfates and an associated sulfated dimer provides direct evidence that isoprene in the presence of sulfate aerosol can make a contribution to biogenic organic aerosol above tropical forests. High-resolution mass spectrometry indicates that sulfur can also be incorporated into oxidation products arising from monoterpene precursors in tropical aerosol.

  10. Linking biogenic hydrocarbons to biogenic aerosol in the Borneo rainforest

    NASA Astrophysics Data System (ADS)

    Hamilton, J. F.; Alfarra, M. R.; Robinson, N.; Ward, M. W.; Lewis, A. C.; McFiggans, G. B.; Coe, H.; Allan, J. D.

    2013-07-01

    Emissions of biogenic volatile organic compounds are though to contribute significantly to secondary organic aerosol formation in the tropics, but understanding the process of these transformations has proved difficult, due to the complexity of the chemistry involved and very low concentrations. Aerosols from above a South East Asian tropical rainforest in Borneo were characterised using liquid chromatography-ion trap mass spectrometry, high resolution aerosol mass spectrometry and fourier transform ion cyclotron resonance mass spectrometry (FTICRMS) techniques. Oxygenated compounds were identified in ambient organic aerosol that could be directly traced back to isoprene, monoterpenes and sesquiterpene emissions, by combining field data on chemical structures with mass spectral data generated from synthetically produced products created in a simulation chamber. Eighteen oxygenated species of biogenic origin were identified in the rainforest aerosol from the precursors isoprene, α-pinene, limonene, α-terpinene and β-caryophyllene. The observations provide the unambiguous field detection of monoterpene and sesquiterpene oxidation products in SOA above a pristine tropical rainforest. The presence of 2-methyltetrol organosulfates and an associated sulfated dimer provides direct evidence that isoprene in the presence of sulfate aerosol can make a contribution to biogenic organic aerosol above tropical forests. High-resolution mass spectrometry indicates that sulfur can also be incorporated into oxidation products arising from monoterpene precursors in tropical aerosol.

  11. On the Biogenic Origins of Homochirality

    NASA Astrophysics Data System (ADS)

    Sojo, Victor

    2015-06-01

    Homochirality, the single-handedness of optically asymmetric chemical structures, is present in all major biological macromolecules. Terrestrial life's preference for one isomer over its mirror image in D-sugars and L-amino acids has both fascinated and puzzled biochemists for over a century. But the contrasting case of the equally fundamental phospholipids has received less attention. Although the phospholipid glycerol headgroups of archaea and bacteria are both exclusively homochiral, the stereochemistries between the two domains are opposite. Here I argue that the reason for this "dual homochirality" was a simple evolutionary choice at the independent origin of the two synthesizing enzymes. More broadly, this points to a trivial biogenic cause for the evolution of homochirality: the enzymatic processes that produce chiral biomolecules are stereospecific in nature. Once an orientation has been favored, shifting to the opposite is both difficult and unnecessary. Homochirality is thus the simplest and most parsimonious evolutionary case.

  12. Water-soluble primary amine compounds in rural continental precipitation

    NASA Astrophysics Data System (ADS)

    Gorzelska, Krystyna; Galloway, James N.; Watterson, Karen; Keene, William C.

    Procedures for collecting, storing and analysing precipitation samples for organic nitrogen studies were developed. These procedures preserve chemical integrities of the species of interest, allow for up to 3 months storage and quantitative determination of water-soluble primary amine compounds, with the overall error at the 2 nM detection limit of less than 30%. This methodology was applied to study amino compounds in precipitation samples collected over a period of one year in central Virginia. Nitrogen concentrations of 13 amino acids and 3 aliphatic amines were summed to calculate the total amine nitrogen (TAN). The concentration of TAN ranged from below our detection level to 6658 nM, and possibly reflected a seasonal variation in the source strength of the atmospheric amines. Overall, the most commonly occurring amino compounds were methyl amine, ethyl amine, glutamic acid, glycine and serine. On average, the highest overall contribution to the TAN came from arginine, asparagine, glutamine, methyl amine, serine and alanine. However, large qualitative and quantitative variations observed among samples warrant caution in interpretation and application of the averaged values. TAN in Charlottesville precipitation contributed from less than 1 to ca 10% of the ammonium nitrogen level. However, our estimates show that amino compounds may contribute significantly to reduced nitrogen budget in precipitation in remote regions.

  13. Fuel additives derived from amido-amines

    SciTech Connect

    Gutierrez, A.; Lundberg, R.D.

    1993-08-24

    A process is described for producing a dispersant useful as an oil additive which comprises: (a) providing a long chain hydrocarbyl substituted mono- or dicarboxylic acid producing material formed by reacting an olefin polymer of C[sub 2] to C[sub 10] monoolefin having a number average molecular weight of about 300 to 10,000 and at least one of a C[sub 4] to C[sub 10] monounsaturated dicarboxylic acid material and a C[sub 3] to C[sub 10] monounsaturated monocarboxylic acid material, said acid producing material having an average of at least about 0.3 dicarboxylic acid producing moieties, per molecule of said olefin polymer present in the reaction mixture used to form said acid producing material; (b) providing an amido-amine compound having at least one primary amino group prepared by reacting at least one polyamine with at least one alpha, beta-unsaturated compound of the formula: R[sup 1]-(C-R[sup 2])[double bond](C-R[sup 3])-(C[double bond]X)-Y wherein X is sulfur or oxygen, Y is -OR[sup 4],-SR[sup 4], or -NR[sup 4](R[sup 5]), and R[sup 1], R[sup 2], R[sup 3], R[sup 4] and R[sup 5] are the same or different and are hydrogen or substituted or unsubstituted hydrocarbyl; and (c) contacting the said acid producing material with said amido-amine compound under conditions sufficient to effect reaction of at least a portion of the primary amino groups on said amido-amine compound with at least a portion of the acid-producing groups in said acid producing material, to form said dispersant.

  14. Recent achievements in developing the biocatalytic toolbox for chiral amine synthesis.

    PubMed

    Kohls, Hannes; Steffen-Munsberg, Fabian; Höhne, Matthias

    2014-04-01

    Novel enzyme activities and chemoenzymatic reaction concepts have considerably expanded the biocatalytic toolbox for chiral amine synthesis. Creating new activities or extending the scope of existing enzymes by protein engineering is a common trend in biocatalysis and in chiral amine synthesis specifically. For instance, an amine dehydrogenase that allows for the direct asymmetric amination of ketones with ammonia was created by mutagenesis of an l-amino acid dehydrogenase. Another trend in chiral amine chemistry is the development of strategies allowing for the synthesis of secondary amines. For example the smart choice of substrates for amine transaminases provided access to secondary amines by chemoenzymatic reactions. Furthermore novel biocatalysts for the synthesis of secondary amines such as imine reductases and Pictet-Spenglerases have been identified and applied. Recent examples showed that the biocatalytic amine synthesis is emerging from simple model reactions towards industrial scale preparation of pharmaceutical relevant substances, for instance, as shown in the synthesis of a Janus kinase 2 inhibitor using an amine transaminase. A comparison of important process parameters such as turnover number and space-time yield demonstrates that biocatalytic strategies for asymmetric reductive amination are maturing and can already compete with established chemical methods. PMID:24721252

  15. Asymmetric Redox-Annulation of Cyclic Amines

    PubMed Central

    2015-01-01

    Cyclic amines such as 1,2,3,4-tetrahydroisoquinoline undergo regiodivergent annulation reactions with 4-nitrobutyraldehydes. These redox-neutral transformations enable the asymmetric synthesis of highly substituted polycyclic ring systems in just two steps from commercial materials. The utility of this process is illustrated in a rapid synthesis of (−)-protoemetinol. Computational studies provide mechanistic insights and implicate the elimination of acetic acid from an ammonium nitronate intermediate as the rate-determining step. PMID:26348653

  16. The vesicular amine transporter family (SLC18): amine/proton antiporters required for vesicular accumulation and regulated exocytotic secretion of monoamines and acetylcholine.

    PubMed

    Eiden, Lee E; Schäfer, Martin K-H; Weihe, Eberhard; Schütz, Burkhard

    2004-02-01

    The vesicular amine transporters (VATs) are expressed as integral proteins of the lipid bilayer membrane of secretory vesicles in neuronal and endocrine cells. Their function is to allow the transport of acetylcholine (by the vesicular acetylcholine transporter VAChT; SLC18A3) and biogenic amines (by the vesicular monoamine transporters VMAT1 and VMAT2; SLC18A1 and SLC18A2) into secretory vesicles, which then discharge them into the extracellular space by exocytosis. Transport of positively charged amines by members of the SLC18 family in all cases utilizes an electrochemical gradient across the vesicular membrane established by proton pumping into the vesicle via a vacuolar ATPase; the amine is accumulated in the vesicle at the expense of the proton gradient, at a ratio of one translocated amine per two translocated protons. The members of the SLC18 family have become important histochemical markers for chemical coding in neuroendocrine tissues and cells. The structural basis of their remarkable ability to transport positively charged amines against a very large concentration gradient, as well as potential disease association with impaired transporter function and expression, are under intense investigation.

  17. NO3 and OH initiated secondary aerosol formation from aliphatic amines - salt formation and effect of water vapor

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Aliphatic amines enter the atmosphere from a variety of sources, and have been detected existing in gas and particle phases in the atmosphere. Similar to ammonia, amines can form inorganic salt through acid-base reactions. However, the atmospheric behavior of amines with atmospheric oxidants (e.g. n...

  18. Unconventional shallow biogenic gas systems

    USGS Publications Warehouse

    Shurr, G.W.; Ridgley, J.L.

    2002-01-01

    Unconventional shallow biogenic gas falls into two distinct systems that have different attributes. Early-generation systems have blanketlike geometries, and gas generation begins soon after deposition of reservoir and source rocks. Late-generation systems have ringlike geometries, and long time intervals separate deposition of reservoir and source rocks from gas generation. For both types of systems, the gas is dominantly methane and is associated with source rocks that are not thermally mature. Early-generation biogenic gas systems are typified by production from low-permeability Cretaceous rocks in the northern Great Plains of Alberta, Saskatchewan, and Montana. The main area of production is on the southeastern margin of the Alberta basin and the northwestern margin of the Williston basin. The huge volume of Cretaceous rocks has a generalized regional pattern of thick, non-marine, coarse clastics to the west and thinner, finer grained marine lithologies to the east. Reservoir rocks in the lower part tend to be finer grained and have lower porosity and permeability than those in the upper part. Similarly, source beds in the units have higher values of total organic carbon. Patterns of erosion, deposition, deformation, and production in both the upper and lower units are related to the geometry of lineament-bounded basement blocks. Geochemical studies show that gas and coproduced water are in equilibrium and that the fluids are relatively old, namely, as much as 66 Ma. Other examples of early-generation systems include Cretaceous clastic reservoirs on the southwestern margin of Williston basin and chalks on the eastern margin of the Denver basin. Late-generation biogenic gas systems have as an archetype the Devonian Antrim Shale on the northern margin of the Michigan basin. Reservoir rocks are fractured, organic-rich black shales that also serve as source rocks. Although fractures are important for production, the relationships to specific geologic structures are

  19. Amine terminated bisaspartimide polymer

    NASA Technical Reports Server (NTRS)

    Kumar, D. (Inventor); Fohlen, G. M. (Inventor); Parker, J. A. (Inventor)

    1986-01-01

    Novel amine terminated bisaspartimides are prepared by a Michael-type reaction of an aromatic bismalteimide and an aromatic diamine in an aprotic solvent. These bisaspartimides are thermally polymerized to yield tough, resinous polymers cross-lined through -NH- groups. Such polymers are useful in applications requiring materials with resistance to change at elevated temperatures, e.g., as lightweight laminates with graphite cloth, molding material prepregs, adhesives and insulating material.

  20. Effect of Bronsted Acids and Bases, and Lewis Acid (Sn(2+)) on the Regiochemistry of the Reaction of Amines with Trifluoromethyl-β-diketones: Reaction of 3-Aminopyrrole to Selectively Produce Regioisomeric 1H-Pyrrolo[3,2-b]pyridines.

    PubMed

    De Rosa, Michael; Arnold, David; Hartline, Douglas; Truong, Linda; Verner, Roman; Wang, Tianwei; Westin, Christian

    2015-12-18

    Reaction of 3-aminopyrrole (as its salt) with trifluoromethyl-β-diketones gave γ-1H-pyrrolo[3,2-b]pyridines via reaction at the less reactive carbonyl group. The trifluoromethyl group increased the electrophilicity of the adjacent carbonyl group and decreased the basicity of the hydroxyl group of the CF3 amino alcohol formed. This amino alcohol was formed faster, but its subsequent dehydration to the β-enaminone was slow resulting in the preferential formation of the γ-regioisomer. Reaction of 4,4,4-trifluoro-1-phenyl-1,3-butadione with 3-aminopyrrole was carried out using a series of 6 amine buffers. Yields of the α-1H-pyrrolo[3,2-b]pyridine increased as the pKa of the amine buffer decreased. Surprisingly the yield went down at higher pKas. There was a change in mechanism as the reaction mixture became more basic. With strong amines trifluoromethyl-β-diketones were present mainly or completely as the enolate. Under reductive conditions (3-nitropyrrole/Sn/AcOH/trifluoromethyl-β-diketone) the α-1H-pyrrolo[3,2-b]pyridine was the major product as a result of Lewis acid catalysis by Sn(2+). Similar α-regiochemistry was observed when the reaction of the 3-aminopyrrole salt with trifluoromethyl-β-diketones was carried out in the presence of base and tin(II) acetate.