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Tryptamines

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https://www.readbyqxmd.com/read/29925228/access-to-3a-benzoylmethyl-pyrrolidino-2-3-b-indolines-via-cuii-catalyzed-radical-annulation-c3-functionalization-sequence
#1
Xiaofeng Chen, Jinbao Fan, Guangyao Zeng, Jinjin Ma, Chenxi Wang, Yajing Wang, Yingjun Zhou, Xu Deng
A CuII-catalyzed radical annulation/C3-functionalization cascade of tryptamine derivatives with aryl ethylene is reported. The mild catalytic conditions enables the facile construction of 3a-benzoylmethylpyrrolidino[2,3-b]indolines with excellent chemo- and regio-selectivities. Remarkably, this novel method utilizes earth-abundant and inexpensive cupric salt as the catalyst and air as the co-oxidant, rendering the process highly environmentally friendly and atom-economic. Presumably, the reaction proceeds through CuII-initiated formation of pyrrolidino[2,3-b]indolines radical intermediate I, which is successively trapped by aryl ethylene and O2 to form the product...
June 21, 2018: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/29902441/gut-microbiota-produced-tryptamine-activates-an-epithelial-g-protein-coupled-receptor-to-increase-colonic-secretion
#2
Yogesh Bhattarai, Brianna B Williams, Eric J Battaglioli, Weston R Whitaker, Lisa Till, Madhusudan Grover, David R Linden, Yasutada Akiba, Karunya K Kandimalla, Nicholas C Zachos, Jonathan D Kaunitz, Justin L Sonnenburg, Michael A Fischbach, Gianrico Farrugia, Purna C Kashyap
Tryptamine, a tryptophan-derived monoamine similar to 5-hydroxytryptamine (5-HT), is produced by gut bacteria and is abundant in human and rodent feces. However, the physiologic effect of tryptamine in the gastrointestinal (GI) tract remains unknown. Here, we show that the biological effects of tryptamine are mediated through the 5-HT4 receptor (5-HT4 R), a G-protein-coupled receptor (GPCR) uniquely expressed in the colonic epithelium. Tryptamine increases both ionic flux across the colonic epithelium and fluid secretion in colonoids from germ-free (GF) and humanized (ex-GF colonized with human stool) mice, consistent with increased intestinal secretion...
June 13, 2018: Cell Host & Microbe
https://www.readbyqxmd.com/read/29902430/a-microbial-drugstore-for-motility
#3
John F Cryan, Gerard Clarke, Timothy G Dinan, Harriet Schellekens
While there is growing appreciation that the microbiome regulates gut-brain signaling, the underlying mechanisms remain elusive. In this issue of Cell Host & Microbe, Bhattarai et al. (2018) identify bacteria-derived tryptamine as a ligand for the gut-epithelium-expressed GPCR 5-HT4 receptor, thereby functioning as a regulator of gastrointestinal motility.
June 13, 2018: Cell Host & Microbe
https://www.readbyqxmd.com/read/29902071/anti-inflammatory-effects-of-melatonin-a-mechanistic-review
#4
Seyed Mohammad Nabavi, Seyed Fazel Nabavi, Antoni Sureda, Janbo Xiao, Ahmad Reza Dehpour, Samira Shirooie, Ana Sanches Silva, Alessandra Baldi, Haroon Khan, Maria Daglia
N-acetyl-5-methoxy-tryptamine (melatonin) is a natural substance produced both by plants, as a secondary metabolite, and animals, by the pineal gland and other tissues. In humans, melatonin participates in numerous functions including the regulation of mood, sleep, reproduction, promotion of immunomodulation, antioxidant defense and as an anti-inflammatory agent. The anti-inflammatory activity of melatonin could yield beneficial effects on intake, particularly against the chronic inflammation which underlies many chronic diseases...
June 14, 2018: Critical Reviews in Food Science and Nutrition
https://www.readbyqxmd.com/read/29892159/covalent-adduction-of-endogenous-and-food-derived-quinones-to-a-protein-its-biological-significance
#5
REVIEW
Yoji Kato, Naoko Suga
There are many chemically reactive compounds, including quinone, in living systems and also food. Even after the ingestion of food polyphenols, quinones derived from catechol moieties could form endogenously in the body. Dopaquinone, dopamine quinone, estrogen-derived quinones, tryptamine-4,5-dione, and ubiquinone are examples of an endogenous quinone. These indicate that quinone is ubiquitously formed or present in living systems and food. Quinones can induce a variety of hazardous effects and also could have beneficial physiological effects...
May 2018: Journal of Clinical Biochemistry and Nutrition
https://www.readbyqxmd.com/read/29883400/melatonin-a-multifunctional-factor-in-plants
#6
REVIEW
Jibiao Fan, Yan Xie, Zaichao Zhang, Liang Chen
Melatonin ( N -acetyl-5-methoxy-tryptamine) is a universal molecule that is present in animals and plants. It has been detected in different kinds of plants and organs in different levels. Melatonin in plants shares the same initial biosynthesis compound with auxin, and therefore functions as indole-3-acetic acid like hormones. Moreover, melatonin is involved in regulating plant growth and development, protecting plants against biotic and abiotic stresses, such as salt, drought, cold, heat and heavy metal stresses...
May 21, 2018: International Journal of Molecular Sciences
https://www.readbyqxmd.com/read/29867206/thiazole-amides-a-novel-class-of-algaecides-against-freshwater-harmful-algae
#7
Ying Wang, Qisheng Liu, Zhigang Wei, Na Liu, Yajuan Li, Duo Li, Zhong Jin, Xiaohua Xu
Currently, harmful algal blooms are being one of ever-increasing global environmental problems. Much attention has been paid to the use of natural products as the selective algaecides due to their low toxicity, high selectivity and eco-friendly properties. In the present study, the thiazole alkaloid (1), originally isolated from Thermoactino-myces strain TM-64, was shown to exhibit potent algicidal activity against three typically harmful cyanobacterial algae, S. obliqnus, M. aeruginosa, and C. pyrenoidosa...
June 4, 2018: Scientific Reports
https://www.readbyqxmd.com/read/29852524/asymmetric-synthesis-of-r-1-alkyl-substituted-tetrahydro-%C3%A3-carbolines-catalyzed-by-strictosidine-synthases
#8
Desiree Pressnitz, Eva-Maria Fischereder, Jakob Pletz, Christina Kofler, Lucas Hammerer, Katharina Hiebler, Horst Lechner, Nina Richter, Elisabeth Eger, Wolfgang Kroutil
Stereoselective methods for the synthesis of tetrahydro-ß-carbolines are of significant interest due to the broad spectrum of biological activity of the target molecules. In the plant kingdom strictosidine synthases catalyze the C-C coupling via a Pictet-Spengler reaction of tryptamine and secologanin to exclusively form the (S)-configured tetrahydro-ß-carboline (S)-strictosidine. Investigating the biocatalytic Pictet-Spengler reaction of tryptamine with small-molecular-weight aliphatic aldehydes revealed that the strictosidine synthases gave unexpectedly access to the (R)-configured product...
May 31, 2018: Angewandte Chemie
https://www.readbyqxmd.com/read/29797912/-the-effect-of-paraplegic-triple-needling-combined-with-rehabilitation-training-on-psychological-and-daily-living-ability-of-patients-with-spinal-cord-injury
#9
Yinjie Cui, Xiaojuan Song, Qian Wang, Wenchun Wang, Anren Zhang
OBJECTIVE: To compare the effects of "paraplegic triple needling" and conventional needling on psychological and daily living ability of patients with spinal cord injury. METHODS: A total of 50 patients with spinal cord injury were randomized into an observation group and a control group, 25 cases in each one. Rehabilitation training was applied in the two groups. In the observation group, on the basis of rehabilitation training, "paraplegic triple needling" was added, namely, puncturing the governor vessel (GV) and back- shu points respectively in the upper and lower segments of the injury plane and locating the key muscle movement points of the lower extremities by the peripheral nerve electrical stimulation device...
May 12, 2018: Zhongguo Zhen Jiu, Chinese Acupuncture & Moxibustion
https://www.readbyqxmd.com/read/29777946/screening-method-for-rapid-classification-of-psychoactive-substances-in-illicit-tablets-using-mid-infrared-spectroscopy-and-pls-da
#10
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
https://www.readbyqxmd.com/read/29775059/intrinsic-antioxidant-potential-of-the-aminoindole-structure-a-computational-kinetics-study-of-tryptamine
#11
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
https://www.readbyqxmd.com/read/29771519/enantioselective-bromocyclization-of-tryptamines-induced-by-chiral-co-iii-complexes-templated-br%C3%A3-nsted-acids-under-an-air-atmosphere
#12
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
https://www.readbyqxmd.com/read/29767990/synthesis-of-carbolines-via-palladium-carboxylic-acid-joint-catalysis
#13
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
https://www.readbyqxmd.com/read/29751062/new-insights-into-auxin-metabolism-in-bradyrhizobium-japonicum
#14
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
https://www.readbyqxmd.com/read/29748982/redox-responsive-polymer-with-self-immolative-linkers-for-the-release-of-payloads
#15
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
https://www.readbyqxmd.com/read/29740267/indolethylamine-n-methyltransferase-polymorphisms-genetic-and-biochemical-approaches-for-study-of-endogenous-n-n-dimethyltryptamine
#16
REVIEW
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
https://www.readbyqxmd.com/read/29738463/determination-of-biogenic-amines-in-seawater-using-capillary-electrophoresis-with-capacitively-coupled-contactless-conductivity-detection
#17
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
https://www.readbyqxmd.com/read/29737077/-determination-of-5-hydroxytryptamine-adrenalin-and-noradrenalin-in-human-plasma-by-pre-column-derivatization-hplc-ms-ms
#18
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
https://www.readbyqxmd.com/read/29735983/resistance-of-rice-to-insect-pests-mediated-by-suppression-of-serotonin-biosynthesis
#19
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
https://www.readbyqxmd.com/read/29734371/heterologous-expression-of-zjomt-from-zoysia-japonica-in-escherichia-coli-confers-aluminum-resistance-through-melatonin-production
#20
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
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