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https://www.readbyqxmd.com/read/28933078/-advance-in-biosynthesis-of-terpenoid-indole-alkaloids-and-its-regulation-in-catharanthus-roseus
#1
Xue-Jun Kuang, Cai-Xia Wang, Li-Qiu Zou, Xiao-Xuan Zhu, Chao Sun
Catharanthus roseus can produce a variety of terpenoid indole alkaloids (TIA), most of which exhibit strong pharmacological activities. Hence, biosynthesis and regulation of TIA have received recent attention. 3α (S)-strictosidine is an important node in TIA biosynthesis, which is a condensation product of secologanin and tryptamine. The former is produced in iridoid pathway, and the latter is produced in indole pathway. Vindoline and catharanthine, which are produced respectively by 3α (S)-strictosidine via multi-step enzymatic reaction, can form α-3, 4-anhydrovinblastine by the condensation reaction...
November 2016: Zhongguo Zhong Yao za Zhi, Zhongguo Zhongyao Zazhi, China Journal of Chinese Materia Medica
https://www.readbyqxmd.com/read/28932467/crystal-structure-and-dft-study-of-e-n-2-1h-indol-3-yl-eth-yl-1-anthracen-9-yl-methanimine
#2
Md Serajul Haque Faizi, Necmi Dege, Sergey Malinkin, Tetyana Yu Sliva
The title compound, C25H20N2, (I), was synthesized from the condensation reaction of anthracene-9-carbaldehyde and tryptamine in dry ethanol. The indole ring system (r.m.s. deviation = 0.016 Å) makes a dihedral angle of 63.56 (8)° with the anthracene ring (r.m.s. deviation = 0.023 Å). There is a short intra-molecular C-H⋯N inter-action present, and a C-H⋯π inter-action involving the two ring systems. In the crystal, the indole H atom forms an inter-molecular N-H⋯π inter-action, linking mol-ecules to form chains along the b-axis direction...
September 1, 2017: Acta Crystallographica. Section E, Crystallographic Communications
https://www.readbyqxmd.com/read/28930453/ab-initio-qm-mm-modelling-of-the-rate-limiting-proton-transfer-step-in-the-deamination-of-tryptamine-by-aromatic-amine-dehydrogenase
#3
Kara Elizabeth Ranaghan, William G Morris, Laura Masgrau, Kittusamy Senthilkumar, Linus O Johannissen, Nigel S Scrutton, Jeremy N Harvey, Frederick R Manby, Adrian J Mulholland
Aromatic amine dehydrogenase (AADH) and related enzymes are at the heart of debates on the roles of quantum tunnelling and protein dynamics in catalysis. The reaction of tryptamine in AADH involves significant quantum tunnelling in the rate-limiting proton transfer step, shown e.g. by large H/D primary kinetic isotope effects (KIEs), with unusual temperature dependence. We apply correlated ab initio combined quantum mechanics/molecular mechanics (QM/MM) methods, at levels up to local coupled cluster theory (LCCSD(T)/(aug)-cc-pVTZ), to calculate accurate potential energy surfaces for this reaction, which are necessary for quantitative analysis of tunnelling contributions and reaction dynamics...
September 20, 2017: Journal of Physical Chemistry. B
https://www.readbyqxmd.com/read/28926757/mn-ii-based-t1-and-t2-potential-mri-contrast-agent-appended-with-tryptamine-recognition-moiety-for-a%C3%AE-plaques
#4
Neeraj Rastogi, Nidhi Tyagi, Ovender Singh, B S Hemanth Kumar, Udai P Singh, Kaushik Ghosh, Raja Roy
We report the synthesis and characterization of manganese(II) complexes having pentadentate ligands L1 (2,6-bis(1-(2-phenyl-2-(pyridin-2-yl)hydrazono)ethyl)pyridine), L2 (methyl 2,6-bis((E)-1-(2-phenyl-2-(pyridin-2yl)hydrazono)ethyl)isonicotinate), L3 (N-(2-(1H-indol-3-yl)ethyl)-2,6-bis((E)-1-(2-phenyl-2-(pyridin2yl)hydrazono)ethyl)isonicotiamide) and their application as dual contrast agents for simultaneous T1 and T2 weighted magnetic resonance imaging. Single crystal analysis of all the complexes [Mn(II)L1, Mn(II)L2 and Mn(II)L3] confirm the formation of novel seven-coordinate manganese complexes with an inner sphere water and perchlorate ion...
September 5, 2017: Journal of Inorganic Biochemistry
https://www.readbyqxmd.com/read/28880094/enantiospecific-synthesis-of-%C3%AE-substituted-tryptamines
#5
Heather N Rubin, Kinney Van Hecke, Jonathan J Mills, Jennifer Cockrell, Jeremy B Morgan
Functionalized tryptamines are targets of interest for development as small molecule therapeutics. The ring opening of aziridines with indoles is a powerful method for tryptamine synthesis where isomer formation can be controlled. 3,5-Dinitrobenzoyl (DNB)-protected aziridines undergo regioselective, enantiospecific ring opening to produce β-substituted tryptamines for a series of indoles. Attack at the more substituted aziridine carbon occurs in an SN2-like fashion to generate DNB-tryptamine products as synthetic precursors...
September 7, 2017: Organic Letters
https://www.readbyqxmd.com/read/28873563/application-of-3-5-bis-trifluoromethyl-phenyl-isothiocyanate-for-the-determination-of-selected-biogenic-amines-by-lc-tandem-mass-spectrometry-and-19-f-nmr
#6
Aneta Jastrzębska, Anna Piasta, Marek Krzemiński, Edward Szłyk
3,5-Bis-(trifluoromethyl)phenyl isothiocyanate, was used as a convenient reagent for the derivatization of histamine, tyramine, tryptamine and 2-phenylethylamine, which eliminates the purification step. The obtained derivatives were determined by liquid chromatography-tandem mass spectrometry (LC-MS/MS). Additionally, the total amount of these amines was determined by (19)F nuclear magnetic resonance analysis. The procedures were optimized and validated for linearity, limit of detection and quantification, intra- and inter-day precision and recovery resulting in good reproducibility and accuracy...
January 15, 2018: Food Chemistry
https://www.readbyqxmd.com/read/28873546/reduction-of-biogenic-amines-in-sufu-by-ethanol-addition-during-ripening-stage
#7
Shuang Qiu, Ying Wang, Yongqiang Cheng, Yan Liu, Madhav P Yadav, Lijun Yin
The aim of this study was to investigate the content of biogenic amines (BAs) in different types of sufu samples obtained from different producers, and the effect of ethanol in reducing BA levels during sufu ripening. The results showed that different manufacturing processes altered the distribution of BAs in commercial sufu. Putrescine, cadaverine, histamine, and tryptamine were the main and common BAs in red, white and grey sufu. The contents of putrescine, cadaverine, tryptamine, β-phenylethylamine and tyramine in the grey sufu of all producer brands were significantly (p<0...
January 15, 2018: Food Chemistry
https://www.readbyqxmd.com/read/28872251/room-temperature-synthesis-and-binding-studies-of-solution-processable-histamine-imprinted-microspheres
#8
Edwin F Romano, Clovia I Holdsworth, Joselito P Quirino, Regina C So
Accurate quantification of histamine levels in food and in biological samples is important for monitoring the quality of food products and for the detection of pathophysiological conditions. In this study, solution processable histamine-imprinted microspheres were synthesized at 30°C via dilute free radical phototochemical polymerization technique using ethylene glycol dimethacrylate (EGDMA) as the crosslinker and methacrylic acid (MAA) as the monomer. The processability of the resulting polymer is dictated by the monomer feed concentration (eg, 4 wt% 80:20 EGDMA:MAA formulation) and solvent (acetonitrile)...
September 5, 2017: Journal of Molecular Recognition: JMR
https://www.readbyqxmd.com/read/28870224/psychoactive-substances-as-a-last-resort-a-qualitative-study-of-self-treatment-of-migraine-and-cluster-headaches
#9
Martin Andersson, Mari Persson, Anette Kjellgren
BACKGROUND: Treatment resistant cluster headache and migraine patients are exploring alternative treatments online. The aim of this study was to improve comprehension regarding the use of non-established or alternative pharmacological treatments used by sufferers of cluster headaches and migraines. METHODS: A qualitative thematic analysis of the users' own accounts presented in online forum discussions were conducted. The forum boards https://shroomery.org/ , http://bluelight...
September 5, 2017: Harm Reduction Journal
https://www.readbyqxmd.com/read/28860561/short-chain-fatty-acids-enhance-aryl-hydrocarbon-ah-responsiveness-in-mouse-colonocytes-and-caco-2-human-colon-cancer-cells
#10
Un-Ho Jin, Yating Cheng, Hyejin Park, Laurie A Davidson, Evelyn S Callaway, Robert S Chapkin, Arul Jayaraman, Andrew Asante, Clinton Allred, Evelyn A Weaver, Stephen Safe
Aryl hydrocarbon receptor (AhR) ligands are important for gastrointestinal health and play a role in gut inflammation and the induction of T regulatory cells, and the short chain fatty acids (SCFAs) butyrate, propionate and acetate also induce similar protective responses. Initial studies with butyrate demonstrated that this compound significantly increased expression of Ah-responsive genes such as Cyp1a1/CYP1A1 in YAMC mouse colonocytes and Caco-2 human colon cancer cell lines. Butyrate synergistically enhanced AhR ligand-induced Cyp1a1/CYP1A1 in these cells with comparable enhancement being observed for 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) and also microbiota-derived AhR ligands tryptamine, indole and 1,4-dihydroxy-2-naphthoic acid (DHNA)...
August 31, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28830759/phencyclidine-like-in%C3%A2-vivo-effects-of-methoxetamine-in-mice-and-rats
#11
Michael D Berquist, William S Hyatt, Jonathan Bauer-Erickson, Brenda M Gannon, Andrew P Norwood, William E Fantegrossi
Methoxetamine (MXE) is a novel drug of abuse that is structurally similar to phencyclidine (PCP). In the present study, rats were trained to discriminate PCP from saline and substitution tests were performed with arylcyclohexylamines PCP, eticyclidine (PCE), tenocyclidine (TCP), and MXE. PCP and PCE engendered PCP-lever selection in all subjects, whereas MXE and TCP produced PCP-lever selection in animals that did not display behavioral disruption. Last, the substituted tryptamine dipropyltryptamine (DPT) produced moderate PCP-lever selection and elicited behavioral disruption in all subjects at the highest dose tested...
August 19, 2017: Neuropharmacology
https://www.readbyqxmd.com/read/28819877/engineering-of-escherichia-coli-for-the-synthesis-of-n-hydroxycinnamoyl-tryptamine-and-serotonin
#12
Su Jin Lee, Geun-Young Sim, Youngshim Lee, Bong-Gyu Kim, Joong-Hoon Ahn
Plants synthesize various phenol amides. Among them, hydroxycinnamoyl (HC) tryptamines and serotonins exhibit antioxidant, anti-inflammatory, and anti-atherogenic activities. We synthesized HC-tryptamines and HC-serotonin from several HCs and either tryptamine or serotonin using Escherichia coli harboring the 4CL (4-coumaroyl CoA ligase) and CaHCTT [hydroxycinnamoyl-coenzyme A:serotonin N-(hydroxycinnamoyl)transferase] genes. E. coli was engineered to synthesize N-cinnamoyl tryptamine from glucose. TDC (tryptophan decarboxylase) and PAL (phenylalanine ammonia lyase) along with 4CL and CaHCTT were introduced into E...
August 17, 2017: Journal of Industrial Microbiology & Biotechnology
https://www.readbyqxmd.com/read/28808798/genetic-engineering-approach-using-early-vinca-alkaloid-biosynthesis-genes-led-to-increased-tryptamine-and-terpenoid-indole-alkaloids-biosynthesis-in-differentiating-cultures-of-catharanthus-roseus
#13
Abhishek Sharma, Priyanka Verma, Archana Mathur, Ajay Kumar Mathur
Catharanthus roseus today occupies the central position in ongoing metabolic engineering efforts in medicinal plants. The entire multi-step biogenetic pathway of its very expensive anticancerous alkaloids vinblastine and vincristine is fairly very well dissected at biochemical and gene levels except the pathway steps leading to biosynthesis of monomeric alkaloid catharanthine and tabersonine. In order to enhance the plant-based productivity of these pharma molecules for the drug industry, cell and tissue cultures of C...
August 14, 2017: Protoplasma
https://www.readbyqxmd.com/read/28806604/chemodiversity-of-tryptamine-derived-alkaloids-in-six-costa-rican-palicourea-species-rubiaceae-palicoureeae
#14
Andreas Berger, Elias Tanuhadi, Lothar Brecker, Johann Schinnerl, Karin Valant-Vetschera
We report 14 harmala and tryptamine-iridoid alkaloids with various tri-, tetra- and pentacyclic cores from leaves and stem bark of six species of the large and complex neotropical genus Palicourea. Among them is the previously undescribed compound deoxostrictosamide which is related to strictosamide, a key intermediate in camptothecin biosynthesis. In addition, we describe the occurrence of 1,2,3,4-tetrahydronorharman-1-one for the first time within Rubiaceae and ophiorine A and B, two alkaloids with an unusual core bearing a betaine function and a zwitterion as new for the genus...
August 11, 2017: Phytochemistry
https://www.readbyqxmd.com/read/28801295/-foshouningshen-decoction-improves-sleeping-via-the-serotonergic-system-in-a-rat-model-of-insomnia
#15
Jie-Cong Huang, Wei Xie, Ning Deng, Wen-Lin Liang, Dong-Rong Hu, Yu Hong, Yang Zhou
OBJECTIVE: To evaluate the sedative and hypnotic effects of Foshouningshen decoction (FSNSD) and study its effects on expressions of 5-hydroxy tryptamine (5-HT) and 5-HT1A receptor (5-HT1AR) in the hippocampus in a rat model of insomnia. METHODS: Male KM mice were divided into control group, estazolam (0.4 mg/kg daily) group, and low-, moderate-, and high-dose FSNSD groups (daily dose of 12, 24, and 48 g/kg, respectively). After corresponding treatments for 1 week, the mice underwent sleep-inducing test with subthreshold and threshold doses of sodium pentobarbital...
August 20, 2017: Nan Fang Yi Ke da Xue Xue Bao, Journal of Southern Medical University
https://www.readbyqxmd.com/read/28799587/unravelling-hydrogen-bonding-interactions-of-tryptamine-water-dimer-from-neutral-to-cation
#16
Zongyuan Liu, Carl O Trindle, Quanli Gu, Wei Wu, Peifeng Su
The neutral and cationic forms of tryptamine-water dimer present a variety of noncovalent interactions. To characterize these interactions, a series of complementary methods, including the quantum theory of atoms in molecules, noncovalent interaction plots, natural bond orbital analysis, and energy decomposition analysis, were used. For the first time, the existence of the three intermolecular H-bonds in the conformer-locked tryptamine-water dimer A-H2O are identified, highlighting a single water's role as one proton donor and two proton acceptors as it binds to tryptamine...
August 11, 2017: Physical Chemistry Chemical Physics: PCCP
https://www.readbyqxmd.com/read/28782205/microbiota-derived-tryptophan-indoles-increase-after-gastric-bypass-surgery-and-reduce-intestinal-permeability-in-vitro-and-in-vivo
#17
M Jennis, C R Cavanaugh, G C Leo, J R Mabus, J Lenhard, P J Hornby
BACKGROUND: The diet and microbiome contribute to metabolic disease in part due to increased intestinal inflammation and permeability. Dietary tryptophan is metabolized by both mammalian and bacterial enzymes. Using in vitro, in vivo models, and clinical data, we tested whether bacterial tryptophan indole derivatives underlie the positive benefits of microbiota on inflammation that is associated with metabolic disease. METHODS: In high-fat diet (HFD)-fed mice intestinal permeability and plasma endotoxin levels were measured after indole-3-propionic acid (IPA; 20 mg kg(-1) p...
August 7, 2017: Neurogastroenterology and Motility: the Official Journal of the European Gastrointestinal Motility Society
https://www.readbyqxmd.com/read/28777688/attitudes-and-beliefs-about-new-psychoactive-substance-use-among-electronic-dance-music-party-attendees
#18
Joseph J Palamar, Patricia Acosta, Charles M Cleland
BACKGROUND: Attitudes and beliefs about drug use have been shown to be robust correlates of use of drugs such as alcohol, marijuana, and cocaine; however, little is known regarding attitudes or beliefs about new psychoactive substances (NPS). We sought to examine attitudes and beliefs about NPS and how they relate to self-reported use in a high-risk population-electronic dance music (EDM) party attendees. METHOD: 1,048 individuals (age 18-40) were surveyed entering EDM parties in New York City in 2016...
August 4, 2017: Substance Use & Misuse
https://www.readbyqxmd.com/read/28777585/reductive-co2-fixation-via-tandem-c-c-and-c-n-bond-formation-synthesis-of-spiro-indolepyrrolidines
#19
Dao-Yong Zhu, Lei Fang, Hui Han, Yazhou Wang, Ji-Bao Xia
We describe herein a tandem C-C and C-N bond-forming reaction in the reductive functionalization of CO2, an abundant and cheap C1 chemical feedstock. This catalytic metal-free CO2 fixation afforded spiro-indolepyrrolidines by dearomatization of tryptamine derivatives with broad scope and good functional group tolerance under mild conditions.
August 4, 2017: Organic Letters
https://www.readbyqxmd.com/read/28763571/enzymatic-synthesis-of-psilocybin
#20
Janis Fricke, Felix Blei, Dirk Hoffmeister
Psilocybin is the psychotropic tryptamine-derived natural product of Psilocybe carpophores, the so-called "magic mushrooms". Although its structure has been known for 60 years, the enzymatic basis of its biosynthesis has remained obscure. We characterized four psilocybin biosynthesis enzymes, namely i) PsiD, which represents a new class of fungal l-tryptophan decarboxylases, ii) PsiK, which catalyzes the phosphotransfer step, iii) the methyltransferase PsiM, catalyzing iterative N-methyl transfer as the terminal biosynthetic step, and iv) PsiH, a monooxygenase...
August 1, 2017: Angewandte Chemie
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