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Leandro S A Pereira, Fernanda L C Lisboa, José Coelho Neto, Frederico N Valladão, Marcelo M Sena
Several new psychoactive substances (NPS) have reached the illegal drug market in recent years, and ecstasy-like tablets are one of the forms affected by this change. Cathinones and tryptamines have increasingly been found in ecstasy-like seized samples as well as other amphetamine type stimulants. A presumptive method for identifying different drugs in seized ecstasy tablets (n=92) using ATR-FTIR (attenuated total reflectance - Fourier transform infrared spectroscopy) and PLS-DA (partial least squares discriminant analysis) was developed...
May 9, 2018: Forensic Science International
Erika N Bentz, Rosana Maria Lobayan, Henar Martinez, Pilar Redondo, Antonio Largo
A computational kinetics study of the antioxidant activity of tryptamine toward HO● and HOO● radicals in water at 298 K has been carried out. Density functional methods have been employed for the quantum chemical calculations and conventional transition state theory was used for rate constants evaluation. Different mechanisms have been considered: radical adduct formation (RAF), single electron transfer (SET), and hydrogen atom transfer (HAT). For the reaction of tryptamine with the hydroxyl radical nearly all channels are diffusion controlled, and the overall rate constant is very high, 6...
May 18, 2018: Journal of Physical Chemistry. B
Kun Liu, Hua-Jie Jiang, Na Li, Hui Li, Jing Wang, Zheng-Zhu Zhang, Jie Yu
The chiral Co(III)-complex-templated Brønsted acids were found to be efficient bifunctional phase-transfer catalysts for the highly enantioselective bromocyclization of protected tryptamines with readily available N-bromosuccinimide (NBS) under an air atmosphere. The 3-bromohexahydropyrrolo[2,3-b]indoles, which are key building blocks of cyclotryptamine alkaloids, were thus obtained in up to 95% yield and 93.5:6.5 er.
May 17, 2018: Journal of Organic Chemistry
Gianpiero Cera, Matteo Lanzi, Davide Balestri, Nicola Della Ca', Raimondo Maggi, Franca Bigi, Max Malacria, Giovanni Maestri
The combination of a Pd(0) complex with benzoic acid converts propargylic tryptamines to the corresponding tetrahydro-β-carbolines. The method uses unprotected indoles and affords the desired products with ample functional group tolerance. Detailed modeling studies reveal a close synergy between the organic and metal catalysts, which enables sequential alkyne isomerization, indole C-H activation, and eventual C-C reductive elimination to afford the target heterocycles.
May 16, 2018: Organic Letters
Daniela Torres, Iliana Benavidez, Florencia Donadio, Elias Mongiardini, Susana Rosas, Stijn Spaepen, Jozef Vanderleyden, Aleš Pěnčík, Ondřej Novák, Miroslav Strnad, Jitka Frébortová, Fabricio Cassán
Bacterial metabolism of phytohormones includes several processes such as biosynthesis, catabolism, conjugation, hydrolysis and homeostatic regulation. However, only biosynthesis and occasionally catabolism are studied in depth in microorganisms. In this work, we evaluated and reconsidered IAA metabolism in B. japonicum E109, one of the most widely used strains for soybean inoculation around the world. The genomic analysis of the strain showed the presence of several genes responsible for IAA biosynthesis, mainly via indole-3-acetonitrile (IAN), indole-3-acetamide (IAM) and tryptamine (TAM) pathways...
May 8, 2018: Research in Microbiology
Supitchaya Iamsaard, Farzad Seidi, Naruphorn Dararatana, Daniel Crespy
Previous couplings of corrosion inhibitors to redox-responsive polymers via covalent bonding suffer from several drawbacks. It is presented here novel redox-responsive polymer-corrosion inhibitor conjugates that contain self-immolative linkers in their side chains. Very fast redox-induced release of tryptamine, a drug and a corrosion inhibitor, is observed after applying a reductive trigger.
May 11, 2018: Macromolecular Rapid Communications
Jon G Dean
N,N -dimethyltryptamine (DMT) is a powerful serotonergic psychedelic whose exogenous administration elicits striking psychedelic effects in humans. Studies have identified DMT and analogous compounds (e.g., 5-hydroxy-DMT, 5-methoxy-DMT) alongside of an enzyme capable of synthesizing DMT endogenously from tryptamine, indolethylamine- N -methyltransferase (INMT), in human and several other mammalian tissues. Subsequently, multiple hypotheses for the physiological role of endogenous DMT have emerged, from proposed immunomodulatory functions to an emphasis on the overlap between the mental states generated by exogenous DMT and naturally occurring altered states of consciousness; e...
2018: Frontiers in Neuroscience
Elbaleeq A Gubartallah, Ahmad Makahleh, Joselito P Quirino, Bahruddin Saad
A rapid and green analytical method based on capillary electrophoresis with capacitively coupled contactless conductivity detection (C⁴D) for the determination of eight environmental pollutants, the biogenic amines (putrescine, cadaverine, spermidine, spermine, tyramine, 2-phenylamine, histamine and tryptamine), is described. The separation was achieved under normal polarity mode at 24 °C and 25 kV with a hydrodynamic injection (50 mbar for 5 s) and using a bare fused-silica capillary (95 cm length × 50 µm i...
May 8, 2018: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Jin Xiang, Qin Yu, Mao-Zhi Liang, Yong-Ping Qin, Feng Nan
OBJECTIVE: To establish a method for the determination of 5-hydroxy tryptamine (5-HT),adrenalin (AD) and noradrenalin (NA) in human plasma using pre-column derivatization HPLC-MS/MS. Methods Derivatives of the plasma samples were produced with dansyl chloride under pH 10.5,and then extracted and enriched with ethyl acetate. The detected chemicals were separated using Ultimate C₁₈ (50 mm×4.6 mm,5 μm) with acetonitrile-water-formic acid=95∶5∶0.05 ( V∶V∶V ) at 0.2 mL/min. The HPLC-MS//MS system was operated under a multiple reaction monitoring mode (MRM) using the electrospray ionization technique in positive mode...
March 2018: Sichuan da Xue Xue Bao. Yi Xue Ban, Journal of Sichuan University. Medical Science Edition
Hai-Ping Lu, Ting Luo, Hao-Wei Fu, Long Wang, Yuan-Yuan Tan, Jian-Zhong Huang, Qing Wang, Gong-Yin Ye, Angharad M R Gatehouse, Yong-Gen Lou, Qing-Yao Shu
Rice is one of the world's most important foods, but its production suffers from insect pests, causing losses of billions of dollars, and extensive use of environmentally damaging pesticides for their control1,2 . However, the molecular mechanisms of insect resistance remain elusive. Although a few resistance genes for planthopper have been cloned, no rice germplasm is resistant to stem borers. Here, we report that biosynthesis of serotonin, a neurotransmitter in mammals 3 , is induced by insect infestation in rice, and its suppression confers resistance to planthoppers and stem borers, the two most destructive pests of rice 2 ...
May 7, 2018: Nature Plants
Hongsong Luo, Chunyan He, Liebao Han
Melatonin is a molecule that can enhance the resistance of plants to abiotic stress. It can alleviate the damage of heavy metal ions, and other chemical substances, changes in temperature and humidity, oxidative stress in higher plants, and enhance resistance of plants to abiotic stress. The transformation of N-Acetyl-5-hydroxy tryptamin into melatonin requires the involvement of methyltransferase. In this study, a methyltransferase gene ZjOMT has been cloned from Zoysia japonica. The gene was induced by aluminum (Al) stress in the leaves and roots of Zoysia japonica, and was up-regulated by 20...
2018: PloS One
Justin Anglin, Reza Beheshti Zavareh, Philipp N Sander, Daniel Haldar, Edouard Mullarky, Lewis C Cantley, Alec C Kimmelman, Costas A Lyssiotis, Luke L Lairson
Pancreatic ductal adenocarcinoma (PDAC) is a lethal malignancy that is extremely refractory to the therapeutic approaches that have been evaluated to date. Recently, it has been demonstrated that PDAC tumors are dependent upon a metabolic pathway involving aspartate aminotransferase 1, also known as glutamate-oxaloacetate transaminase 1 (GOT1), for the maintenance of redox homeostasis and sustained proliferation. As such, small molecule inhibitors targeting this metabolic pathway may provide a novel therapeutic approach for the treatment of this devastating disease...
April 27, 2018: Bioorganic & Medicinal Chemistry Letters
Fereshteh Zarghampour, Yadollah Yamini, Mahroo Baharfar, Mohammad Faraji
In the present research, an on-chip electromembrane extraction coupled with high performance liquid chromatography was developed for monitoring the trace levels of biogenic amines (BAs), including histamine, tryptamine, putrescine, cadaverine and spermidine in food samples. A porous polypropylene sheet membrane impregnated with an organic solvent was placed between the two parts of the chip device to separate the channels. Two platinum electrodes were mounted at the bottom of these channels, which were connected to a power supply, providing the electrical driving force for migration of ionized analytes from the sample solution through the porous sheet membrane into the acceptor phase...
April 23, 2018: Journal of Chromatography. A
Ümran Çiçek, Kader Tokatli
This study aims to evaluate biogenic amine levels of bez sucuks (BS) produced with different meat:fat ratios. For this, three BS groups were manufactured with meat:fat ratios of 90:10 (BS10), 80:20 (BS20), and 70:30 (BS30). The pH and water activity values and biogenic amine amounts of sucuk samples were determined during processing and storage periods and the pH values of the initial mixtures of BS samples were in the range 5.51-5.74, decreasing to 4.72-4.94 by the 14th day. The water activity values of BS samples showed significant decreases as a result of the drying stage and reached to range 0...
February 2018: Korean Journal for Food Science of Animal Resources
Piotr Konopelski, Marcin Ufnal
Increasing evidence proves the pivotal role of gut microbiota in mammals' homeostasis. Gut bacterial metabolites may exert local effects on the intestines, and may enter the circulation, affecting the functions of virtually all organs. Indoles represent a wide group of gut bacteria-derived compounds produced from tryptophan, an essential amino acid and the precursor of endogenous synthesis of tryptamine, serotonin and melatonin. Recently, it has been suggested that gut microbiota and their metabolites, including indoles, may be involved in the etiology of cardiovascular, metabolic, and psychiatric diseases...
April 27, 2018: Current Drug Metabolism
Beatriz González, Jennifer Vázquez, Paul J Cullen, Albert Mas, Gemma Beltran, María-Jesús Torija
Yeasts secrete a large diversity of compounds during alcoholic fermentation, which affect growth rates and developmental processes, like filamentous growth. Several compounds are produced during aromatic amino acid metabolism, including aromatic alcohols, serotonin, melatonin, and tryptamine. We evaluated the effects of these compounds on growth parameters in 16 different wine yeasts, including non- Saccharomyces wine strains, for which the effects of these compounds have not been well-defined. Serotonin, tryptamine, and tryptophol negatively influenced yeast growth, whereas phenylethanol and tyrosol specifically affected non- Saccharomyces strains...
2018: Frontiers in Microbiology
Smitha Krishnan, Yufang Ding, Nima Saedi, Maria Choi, Gautham V Sridharan, David H Sherr, Martin L Yarmush, Robert C Alaniz, Arul Jayaraman, Kyongbum Lee
The gut microbiota plays a significant role in the progression of fatty liver disease; however, the mediators and their mechanisms remain to be elucidated. Comparing metabolite profile differences between germ-free and conventionally raised mice against differences between mice fed a low- and high-fat diet (HFD), we identified tryptamine and indole-3-acetate (I3A) as metabolites that depend on the microbiota and are depleted under a HFD. Both metabolites reduced fatty-acid- and LPS-stimulated production of pro-inflammatory cytokines in macrophages and inhibited the migration of cells toward a chemokine, with I3A exhibiting greater potency...
April 24, 2018: Cell Reports
Denglang Zou, Yurong Du, Jianyuan Kuang, Shihao Sun, Jianbin Ma, Renwang Jiang
This study presents an efficient strategy based on pH-zone-refining counter-current chromatography with a hydrophilic organic/salt-containing two-phase system composed of acetonitrile, sodium chloride and water for preparative separation of polar alkaloids from natural products. Acetonitrile-sodium chloride-water system provides a wider range of polarity for polar alkaloids than classical aqueous two-phase systems. It gets rid of the effect of free hydrogen ion, strong ionic strength, hold low viscosity and the sharp retainer border could be formed easily...
April 10, 2018: Journal of Chromatography. A
Guang-Lei Ma, Juan Xiong, Ezzat E A Osman, Ting Huang, Guo-Xun Yang, Jin-Feng Hu
Two previously undescribed chimonanthine-type [sinodamines A and B] and five related known dimeric tryptamine-derived alkaloids were isolated and characterized from the leaves of the endangered ornamental plant Sinocalycanthus chinensis under the guidance of LC-MS detection and dereplication analyses, along with conventional isolation procedures. Their structures were established on the basis of spectroscopic methods and chemical transformations. Sinodamine A can be regarded as the naturally occurring N-oxide derivative of its pseudo-mesomer sinodamine B...
April 14, 2018: Phytochemistry
Katalin Peto, Norbert Nemeth, Anita Mester, Zsuzsanna Magyar, Souleiman Ghanem, Viktoria Somogyi, Bence Tanczos, Adam Deak, Laszlo Bidiga, Ede Frecska, Balazs Nemes
BACKGROUND: Micro-rheological relations of renal ischemia-reperfusion (I/R) have not been completely elucidated yet. Concerning anti-inflammatory agents, it is supposed that sigma-1 receptor agonist N,N-dimethyl-tryptamin (DMT) can be useful to reduce I/R injury. OBJECTIVE: To investigate the micro-rheological and metabolic parameters, and the effects of DMT in renal I/R in rats. METHODS: In anesthetized rats from median laparotomy both kidneys were exposed...
April 13, 2018: Clinical Hemorheology and Microcirculation
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