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Shruti Shukla, Jong Suk Lee, Vivek K Bajpai, Shivraj Hariram Nile, Yun Suk Huh, Young-Kyu Han, Myunghee Kim
Meju, a cooked and fermented soy bean based food product, is used as a major ingredient in Korean traditional fermented foods such as Doenjang. We developed a novel type of Meju using single and combined extracts of Allium sativum (garlic clove), Nelumbo nucifera (lotus leaves), and Ginkgo biloba (ginkgo leaves) at 1% and 10% concentrations to improve the safety of Meju-based fermented products. Biogenic amines (BAs) in protein-rich fermented food products pose considerable toxical risks. The objective of this study was to investigate the effects of adding selected plant extracts in Meju samples during fermentation...
April 10, 2018: Food and Chemical Toxicology
Dandan Chen, Chunhuan Tian, Xiangyi Li, Zihan Li, Zhida Han, Chun Zhai, Ying Quan, Rongjing Cui, Genhua Zhang
A nanoporous platinum-yttrium alloy (NP-PtY) was fabricated by dealloying ribbons of a PtYAl alloy. Owing to the high porosity and the synergistic effect of Y in the Pt backbone, the NP-PtY exhibits superior structural stability, reproducibility and electrocatalytic activity. An electrochemical sensor was developed for the highly sensitive and selective detection of dopamine (DA) based on the use of a glassy carbon electrode modified with NP-PtY alloy and graphene. The sensor, best operated at 0.16 V vs. SCE, has a linear range covering the 0...
January 10, 2018: Mikrochimica Acta
Elena L Paley, George Perry
Transgenic mice used for Alzheimer's disease (AD) preclinical experiments do not recapitulate the human disease. In our models, the dietary tryptophan metabolite tryptamine produced by human gut microbiome induces tryptophanyl-tRNA synthetase (TrpRS) deficiency with consequent neurodegeneration in cells and mice. Dietary supplements, antibiotics and certain drugs increase tryptamine content in vivo. TrpRS catalyzes tryptophan attachment to tRNAtrp at initial step of protein biosynthesis. Tryptamine that easily crosses the blood-brain barrier induces vasculopathies, neurodegeneration and cell death via TrpRS competitive inhibition...
March 26, 2018: Nutrients
Andrej Ščavničar, Irena Rogelj, Drago Kočar, Sevim Kӧse, Matevž Pompe
A new method for determination of underivatized biogenic amines in cheese based on ion exchange chromatographycoupled with tandem mass spectrometric detection was proposed. The method was applied to the analysis of 10 biogenic amines (trimethylamine, putrescine, cadaverine, histamine, 2-phenylethylamine, spermine, spermidine, tryptamine, agmatine, and tyramine) in different types of cheese. The amines were extracted only with water without any additional derivatization step or sample cleanup. This is a great advantage in terms of simplicity of sample pretreatment procedure compared with other currently existing methods in the literature...
March 23, 2018: Journal of AOAC International
Landon M Klein, Nicholas V Cozzi, Paul F Daley, Simon D Brandt, Adam L Halberstadt
Substantial effort has been devoted toward understanding the psychopharmacological effects of tryptamine hallucinogens, which are thought to be mediated by activation of 5-HT2A and 5-HT1A receptors. Recently, several psychoactive tryptamines based on the N,N-diallyltryptamine (DALT) scaffold have been encountered as recreational drugs. Despite the apparent widespread use of DALT derivatives in humans, little is known about their pharmacological properties. We compared the binding affinities of DALT and its 2-phenyl-, 4-acetoxy-, 4-hydroxy-, 5-methoxy-, 5-methoxy-2-methyl-, 5-fluoro-, 5-fluoro-2-methyl-, 5-bromo-, and 7-ethyl-derivatives at 45 receptor and transporter binding sites...
February 27, 2018: Neuropharmacology
Markus R Meyer
This summarizing and descriptive review article is an update on previously published reviews. It covers English-written and PubMed-listed review articles and original studies published between May 2016 and November 2017 on the toxicokinetics of new psychoactive substances (NPS). Compounds covered include stimulants and entactogens, synthetic cannabinoids, tryptamines, phenethylamine and phencyclidine-like drugs, benzodiazepines, and opioids. First, an overview and discussion is provided on selected review articles followed by an overview and discussion on selected original studies...
February 24, 2018: Handbook of Experimental Pharmacology
Jing Gao, Kang Xu, Hongnan Liu, Gang Liu, Miaomiao Bai, Can Peng, Tiejun Li, Yulong Yin
The gut microbiota influences the health of the host, especially with regard to gut immune homeostasis and the intestinal immune response. In addition to serving as a nutrient enhancer, L-tryptophan (Trp) plays crucial roles in the balance between intestinal immune tolerance and gut microbiota maintenance. Recent discoveries have underscored that changes in the microbiota modulate the host immune system by modulating Trp metabolism. Moreover, Trp, endogenous Trp metabolites (kynurenines, serotonin, and melatonin), and bacterial Trp metabolites (indole, indolic acid, skatole, and tryptamine) have profound effects on gut microbial composition, microbial metabolism, the host's immune system, the host-microbiome interface, and host immune system-intestinal microbiota interactions...
2018: Frontiers in Cellular and Infection Microbiology
Xinna Wang, Yawei Liang, Yaqi Wang, Mingqin Fan, Yanni Sun, Jianli Liu, Ning Zhang
We described a simple, rapid, selective and sensitive HPLC method coupled with fluorescence detection (HPLC-FLD) for simultaneous determination of ten kinds of biogenic amines (BAs: tryptamine, 2-phenethylamine, putrescine, cadaverine, histamine, 5-hydroxytryptamine, tyramine, spermidine, dopamine, spermine). BAs and I.S were derivated with dansyl chloride. A fluorescence detection (λex/λem = 340/510 nm) was used. A satisfactory result of method validation was obtained. The assay was shown to be linear over the range of 0...
February 15, 2018: Biomedical Chromatography: BMC
Takumi Abe, Koji Yamada
A concise synthesis of the azepinobisindole alkaloid iheyamine A from an indole-2,3-epoxide equivalent has been achieved. This method features a formal C3 electrophilic reaction of an indole-2,3-epoxide equivalent with tryptamine to form a 3-aminoindoline and a novel In-catalyzed dehydrative Mannich-type reaction of the hemiaminal to give the azepinobisindole core.
February 13, 2018: Organic Letters
Ying Wan, Hai-Qing Wang, Meng-Meng Xu, Guang-Jian Mei, Feng Shi
A Brønsted acid-catalyzed direct C3-arylation of 2-indolylmethanols with tryptamines and tryptophols has been established, leading to a series of potentially bioactive 2,3'-biindole derivatives with a broad substrate scope and generally good yields (38 examples, up to 96% yield). In this process, the reactivity of the C3-position of 2-indolylmethanol is switched from nucleophilic to electrophilic, which can serve as an umpolung strategy in indole chemistry. This protocol not only provides a new strategy for accessing structurally diversified 2,3'-biindolyl frameworks, but also satisfies the requirement of green chemistry...
February 12, 2018: Organic & Biomolecular Chemistry
Leena Mattsson, Jingjing Xu, Claudia Preininger, Bernadette Tse Sum Bui, Karsten Haupt
We developed a competitive fluorescent molecularly imprinted polymer (MIP) assay to detect biogenic amines in fish samples. MIPs synthesized by precipitation polymerization using histamine as template were used in a batch binding assay analogous to competitive fluoroimmunoassays. Introducing a complex sample matrix, such as fish extract, into the assay changes the environment and the binding conditions, therefore the importance of the sample preparation is extensively discussed. Several extraction and purification methods for fish were comprehensively studied, and an optimal clean-up procedure for fish samples using liquid-liquid extraction was developed...
May 1, 2018: Talanta
Weigang He, Jiadong Hu, Pengyan Wang, Le Chen, Kai Ji, Siyu Yang, Yin Li, Zhilong Xie, Weiqing Xie
A highly enantioselective tandem Michael addition of oxindole derived from tryptamine to alkynone is developed by taking advantage of Sc(OTf)3-chiral N,N'-dioxide catalyst. The reaction enables facile preparation of enantioenriched spiro[pyrrolidine-3,3'-oxindole], which provides a novel strategy for the synthesis of monoterpenoid indole alkaloids. As a demonstration, the asymmetric synthesis of strychnos alkaloids [(-)-tubifoline, (-)-tubifolidine, (-)-dehydrotubifoline] is achieved in 10-11 steps.
February 8, 2018: Angewandte Chemie
Rosana M Lobayan, María Celia Pérez Schmit
Serotonin (5-hydroxytryptamine, SER) is a neurotransmitter that affects many different processes within the human body. We studied the conformational space of SER, and explored in depth the significant stereoelectronic features for the structure stabilization and antioxidant activity. Forty-eight equilibrium structures were described at the B3LYP/6-311++G(d,p) level, characterizing four non-previously reported conformers. Electron distributions were analyzed by topological QTAIM (Quantum Theory of atoms in molecules) and natural bond orbital (NBO) studies...
January 31, 2018: Journal of Molecular Graphics & Modelling
Runhui Ke, Zongsu Wei, Christian Bogdal, Recep Kaya Göktaş, Ruiyang Xiao
Biogenic amines (BAs), a class of nitrogenous compounds that are frequently detected in wine, pose adverse effects to humans. However, with the largest red wine consumption in the world, little is known about national profiles correlating BAs in wines to toxicological/health risks in China. In this study, we conducted a nationwide survey of commercially available wines for the occurrence of BAs. Our sampling campaign covered >90% of wine brands (n = 456) in China in a three year span (2014-2016). The target BAs included tryptamine, phenylethylamine, putrescine, cadaverine, histamine, tyramine, spermidine and spermine...
June 1, 2018: Food Chemistry
Cinzia Sanna, Daniela Rigano, Angela Corona, Dario Piano, Carmen Formisano, Domenica Farci, Genni Franzini, Mauro Ballero, Giuseppina Chianese, Enzo Tramontano, Orazio Taglialatela-Scafati, Francesca Esposito
During our search for potential templates of HIV-1 reverse transcriptase (RT) and integrase (IN) dual inhibitors, the methanolic extract obtained from aerial parts of Limonium morisianum was investigated. Repeated bioassay-guided chromatographic purifications led to the isolation of the following secondary metabolites: myricetin, myricetin 3-O-rutinoside, myricetin-3-O-(6″-O-galloyl)-β-d-galactopyranoside, (-)-epigallocatechin 3-O-gallate, tryptamine, ferulic and phloretic acids. The isolated compounds were tested on both HIV-1 RT-associated RNase H and IN activities...
February 4, 2018: Natural Product Research
Shu-Rong Chen, Shih-Wei Wang, Chien-Jung Su, Hao-Chun Hu, Yu-Liang Yang, Chi-Ting Hsieh, Chia-Chi Peng, Fang-Rong Chang, Yuan-Bin Cheng
Three new compounds, tuberazines A-C (1-3), and eleven known compounds (4-14) were obtained from the ethanolic extract of Taiwanese zoanthid Palythoa tuberculosa. Compounds 1-4 are rare marine natural products with a pyrazine moiety, and compound 5 is a tricyclic tryptamine derivative isolated from nature for the first time. The structures of all isolated metabolites were determined by analyzing their IR, Mass, NMR, and UV spectrometric data. The absolute configuration of 1 was confirmed by comparing the trend of experimental electronic circular dichroism (ECD) with calculated ECD spectra...
January 31, 2018: Marine Drugs
Ya Fatou Njie-Mbye, Jenaye Robinson, Leah Mitchell-Bush, Marshalyn Mckoy, Catherine A Opere, Sunny E Ohia, Naj Sharif
PURPOSE: To determine the serotonergic (5HT) receptor subtype mediating the contraction of bovine posterior ciliary arteries (BPCAs) in vitro. METHODS: Longitudinal isometric tension was measured in BPCA strips (4-5 mm) mounted in 25 mL organ baths containing oxygenated Krebs solution at 37°C. Cumulative contractile concentration-response (C-R) curves were generated for various 5-HT agonists to assess their potencies and maximal degrees of contraction. Multiple agonist C-R curves were also constructed in the presence and absence of receptor-selective antagonists to determine antagonist potencies using Schild plots...
January 25, 2018: Journal of Ocular Pharmacology and Therapeutics
Sunny E Ohia, Ya Fatou Njie-Mbye, Jenaye Robinson, Leah Mitchell, Marshalyn Mckoy, Catherine A Opere, Naj A Sharif
PURPOSE: To study the pharmacological profile of the serotonin (5-hydroxytryptamine [5-HT]) receptor subtype mediating contractions in bovine isolated ciliary muscles. METHODS: Ciliary muscle strips were isolated from bovine eyeballs and mounted in organ baths containing aerated (95% O2, 5% CO2) Krebs buffer solution maintained at 37°C. Each muscle strip was attached at 1 end to a Grass Force-displacement Transducer connected to a Polyview Computer System for recording changes in isometric tension...
January 24, 2018: Journal of Ocular Pharmacology and Therapeutics
T M Nelson, J C Borgogna, R D Michalek, D W Roberts, J M Rath, E D Glover, J Ravel, M D Shardell, C J Yeoman, R M Brotman
Cigarette smoking has been associated with both the diagnosis of bacterial vaginosis (BV) and a vaginal microbiota lacking protective Lactobacillus spp. As the mechanism linking smoking with vaginal microbiota and BV is unclear, we sought to compare the vaginal metabolomes of smokers and non-smokers (17 smokers/19 non-smokers). Metabolomic profiles were determined by gas and liquid chromatography mass spectrometry in a cross-sectional study. Analysis of the 16S rRNA gene populations revealed samples clustered into three community state types (CSTs) ---- CST-I (L...
January 16, 2018: Scientific Reports
Marigianna Marinou, Dimitrios Platis, Farid S Ataya, Evangelia Chronopoulou, Dimitrios Vlachakis, Nikolaos E Labrou
In the present study, a structure-based approach was exploited for the in silico design of a nucleotide coenzyme mimetic ligand. The enzyme formate dehydrogenase (FDH) was employed as a model in our study. The biomimetic ligand was designed and synthesized based on a tryptamine/3-aminopropylphosphonic acid bi-substituted 1,3,5-triazine (Trz) scaffold (Tra-Trz-3APP), which potentially mimics the interactions of NAD+ -FDH complex. Molecular docking studies of the biomimetic ligand predicted that it can occupy the same binding site as the natural coenzyme...
February 2, 2018: Journal of Chromatography. A
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