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  • Retention Indices for Frequently Reported Compounds of Plant Essential Oils
    Retention Indices for Frequently Reported Compounds of Plant Essential Oils V. I. Babushok,a) P. J. Linstrom, and I. G. Zenkevichb) National Institute of Standards and Technology, Gaithersburg, Maryland 20899, USA (Received 1 August 2011; accepted 27 September 2011; published online 29 November 2011) Gas chromatographic retention indices were evaluated for 505 frequently reported plant essential oil components using a large retention index database. Retention data are presented for three types of commonly used stationary phases: dimethyl silicone (nonpolar), dimethyl sili- cone with 5% phenyl groups (slightly polar), and polyethylene glycol (polar) stationary phases. The evaluations are based on the treatment of multiple measurements with the number of data records ranging from about 5 to 800 per compound. Data analysis was limited to temperature programmed conditions. The data reported include the average and median values of retention index with standard deviations and confidence intervals. VC 2011 by the U.S. Secretary of Commerce on behalf of the United States. All rights reserved. [doi:10.1063/1.3653552] Key words: essential oils; gas chromatography; Kova´ts indices; linear indices; retention indices; identification; flavor; olfaction. CONTENTS 1. Introduction The practical applications of plant essential oils are very 1. Introduction................................ 1 diverse. They are used for the production of food, drugs, per- fumes, aromatherapy, and many other applications.1–4 The 2. Retention Indices ........................... 2 need for identification of essential oil components ranges 3. Retention Data Presentation and Discussion . 2 from product quality control to basic research. The identifi- 4. Summary.................................. 45 cation of unknown compounds remains a complex problem, in spite of great progress made in analytical techniques over 5.
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  • Régulation De L'inflammation Par Les Lipides Bioactifs : Interactions Biosynthétiques Et Fonctionnelles Entre Les Endocannabinoïdes Et Les Éicosanoïdes
    Régulation de l'inflammation par les lipides bioactifs : interactions biosynthétiques et fonctionnelles entre les endocannabinoïdes et les éicosanoïdes Thèse Caroline Turcotte Doctorat en microbiologie-immunologie Philosophiæ doctor (Ph. D.) Québec, Canada © Caroline Turcotte, 2019 Régulation de l’inflammation par les lipides bioactifs : interactions biosynthétiques et fonctionnelles entre les endocannabinoïdes et les éicosanoïdes Thèse Caroline Turcotte Sous la direction de : Nicolas Flamand, directeur de recherche Marie-Renée Blanchet, codirectrice de recherche Résumé Les maladies inflammatoires chroniques sont un fardeau de santé important à travers le monde. Les traitements actuellement disponibles soulagent la douleur et l’inflammation, mais leurs effets secondaires rendent leur utilisation à long terme risquée. À la lumière de cette problématique, la communauté scientifique s’intéresse au potentiel d’anti-inflammatoires naturels comme les endocannabinoïdes. Les endocannabinoïdes sont des lipides endogènes qui activent les récepteurs cannabinoïdes (CB1 et CB2). Ils régulent ainsi divers processus physiologiques tels l’appétit, l’adipogénèse et la nociception. Les deux endocannabinoïdes les mieux caractérisés, le 2-AG et l’AEA, peuvent également moduler l’inflammation en activant le récepteur CB2 à la surface des cellules immunitaires. Les souris déficientes pour le récepteur CB2 présentent un phénotype inflammatoire exacerbé, suggérant que ce récepteur est anti-inflammatoire. Cependant, le rôle des endocannabinoïdes dans l’inflammation est beaucoup plus complexe puisqu’ils peuvent être métabolisés en une grande variété de médiateurs lipidiques de l’inflammation. Leur voie de dégradation principale est leur hydrolyse en acide arachidonique (AA), qui sert de précurseur à la biosynthèse d’éicosanoïdes pro-inflammatoires comme le leucotriène B4 et la prostaglandine E2. Ils peuvent également être métabolisés directement par certaines enzymes impliquées dans la synthèse d’éicosanoïdes, pour générer des médiateurs comme les prostaglandines-glycérol (PG-G).
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  • National Center for Toxicological Research
    National Center for Toxicological Research Annual Report Research Accomplishments and Plans FY 2015 – FY 2016 Page 0 of 193 Table of Contents Preface – William Slikker, Jr., Ph.D. ................................................................................... 3 NCTR Vision ......................................................................................................................... 7 NCTR Mission ...................................................................................................................... 7 NCTR Strategic Plan ............................................................................................................ 7 NCTR Organizational Structure .......................................................................................... 8 NCTR Location and Facilities .............................................................................................. 9 NCTR Advances Research Through Outreach and Collaboration ................................... 10 NCTR Global Outreach and Training Activities ............................................................... 12 Global Summit on Regulatory Science .................................................................................................12 Training Activities .................................................................................................................................14 NCTR Scientists – Leaders in the Research Community .................................................. 15 Science Advisory Board ...................................................................................................
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  • Studies on the Pharmacology of Conopharyngine, an Indole Alkaloid of the Voacanga Series
    Br. J. Pharmac. Chemother. (1967), 30, 173-185. STUDIES ON THE PHARMACOLOGY OF CONOPHARYNGINE, AN INDOLE ALKALOID OF THE VOACANGA SERIES BY P. R. CARROLL AND G. A. STARMER From the Department of Pharmacology, University of Sydney, New South Wales, Australia (Received January 17, 1967) Conopharyngine, the major alkaloid present in the leaves of Tabernaemontana (Conopharyngia) pachysiphon var. cumminsi (Stapf) H. Huber was isolated and identified by Thomas & Starmer (1963). The same alkaloid has also been found in the stem bark of a Nigerian variety of the same species by Patel & Poisson (1966) and in the stem bark of Conopharyngia durissima by Renner, Prins & Stoll (1959). Conopharyn- gine is an indole alkaloid of the voacanga type, being 18-carbomethoxy-12,13- dimethoxyibogamine (Fig. 1) and is thus closely related to voacangine and coronaridine. Me.0OC Fig. 1. Conopharyngine (18-carbomethoxy-12,13-dimethoxyibogamine). Some confusion exists in that an alkaloid with an entirely different structure, but also named conopharyngine, was isolated from a cultivated variety of Conopharyngia pachysiphon by Dickel, Lucas & Macphillamy (1959). This compound was shown to be the 3-D-9-glucoside of 55-20a-amino-3 8-hydroxypregnene, and was reported to possess marked hypotensive properties. The presence of steroid alkaloids in the Tabernaemontaneae was hitherto unknown and it was suggested by Raffauf & Flagler (1960) and Bisset (1961) that the plant material was open to further botanical confir- mation. The roots of the conopharyngia species are used in West Africa to treat fever (Kennedy, 1936), including that of malaria (Watt & Breyer-Brandwijk, 1962). The only report on the pharmacology of conopharyngine is that of Zetler (1964), who included it in a study of some of the effects of 23 natural and semi-synthetic alkaloids 174 P.
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  • TAAR1 Activation Modulates Monoaminergic Neurotransmission, Preventing Hyperdopaminergic and Hypoglutamatergic Activity
    TAAR1 activation modulates monoaminergic neurotransmission, preventing hyperdopaminergic and hypoglutamatergic activity Florent G. Revela, Jean-Luc Moreaua, Raul R. Gainetdinovb, Amyaouch Bradaiac, Tatyana D. Sotnikovab, Roland Morya, Sean Durkina, Katrin Groebke Zbindend, Roger Norcrossd, Claas A. Meyere, Veit Metzlera, Sylvie Chaboza, Laurence Ozmena, Gerhard Trubea, Bruno Pouzeta, Bernhard Bettlerf, Marc G. Carong, Joseph G. Wettsteina, and Marius C. Hoenera,1 aNeuroscience Research, dDiscovery Chemistry, and eDiscovery Technologies, Pharmaceuticals Division, F. Hoffmann-La Roche Ltd., CH-4070 Basel, Switzerland; bDepartment of Neuroscience and Brain Technologies, Italian Institute of Technology, 16163 Genoa, Italy; cNeuroservice, Domaine de Saint-Hilaire, 13593 Aix-en-Provence, France; fDepartment of Biomedicine, Institute of Physiology, Pharmazentrum, University of Basel, CH-4056 Basel, Switzerland; and gDepartment of Cell Biology, Duke University Medical Center, Durham, NC 27710 Edited by Richard D. Palmiter, University of Washington, Seattle, WA, and approved March 31, 2011 (received for review February 24, 2011) The trace amine-associated receptor 1 (TAAR1), activated by en- sitive to the locomotor-stimulating effect of d-amphetamine dogenous metabolites of amino acids like the trace amines and show elevated striatal release of dopamine (DA), noradren- p-tyramine and β-phenylethylamine, has proven to be an impor- aline (NA), and serotonin [5-hydroxytryptamine (5-HT)] after a d-amphetamine challenge (10, 12). Furthermore, the spontaneous tant modulator of the dopaminergic system and is considered −/− firing rate of the VTA DA neurons is augmented in Taar1 mice, a promising target for the treatment of neuropsychiatric disorders. fi To decipher the brain functions of TAAR1, a selective TAAR1 ago- and only in WT mice does pTyr decrease this ring rate (10).
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  • The Iboga Alkaloids
    The Iboga Alkaloids Catherine Lavaud and Georges Massiot Contents 1 Introduction ................................................................................. 90 2 Biosynthesis ................................................................................. 92 3 Structural Elucidation and Reactivity ...................................................... 93 4 New Molecules .............................................................................. 97 4.1 Monomers ............................................................................. 99 4.1.1 Ibogamine and Coronaridine Derivatives .................................... 99 4.1.2 3-Alkyl- or 3-Oxo-ibogamine/-coronaridine Derivatives . 102 4.1.3 5- and/or 6-Oxo-ibogamine/-coronaridine Derivatives ...................... 104 4.1.4 Rearranged Ibogamine/Coronaridine Alkaloids .. ........................... 105 4.1.5 Catharanthine and Pseudoeburnamonine Derivatives .. .. .. ... .. ... .. .. ... .. 106 4.1.6 Miscellaneous Representatives and Another Enigma . ..................... 107 4.2 Dimers ................................................................................. 108 4.2.1 Bisindoles with an Ibogamine Moiety ....................................... 110 4.2.2 Bisindoles with a Voacangine (10-Methoxy-coronaridine) Moiety ........ 111 4.2.3 Bisindoles with an Isovoacangine (11-Methoxy-coronaridine) Moiety . 111 4.2.4 Bisindoles with an Iboga-Indolenine or Rearranged Moiety ................ 116 4.2.5 Bisindoles with a Chippiine Moiety ... .....................................
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  • 'Gating' Residues Ile199 and Tyr326 in Human Monoamine Oxidase B
    The ‘gating’ residues Ile199 and Tyr326 in human monoamine oxidase B function in substrate and inhibitor recognition Erika M. Milczek1,*, Claudia Binda2, Stefano Rovida2, Andrea Mattevi2 and Dale E. Edmondson1 1 Departments of Chemistry and Biochemistry, Emory University, Atlanta, Georgia, USA 2 Department of Genetics and Microbiology, University of Pavia, Italy Keywords The major structural difference between human monoamine oxidases A dipartite to monopartite cavity conversion; (MAO A) and B (MAO B) is that MAO A has a monopartite substrate inhibitor specificity; monoamine oxidase B; cavity of 550 A˚3 volume and MAO B contains a dipartite cavity struc- mutations of gating residues; structure of ture with volumes of 290 A˚3 (entrance cavity) and 400 A˚3 (substrate methylene blue complex cavity). Ile199 and Tyr326 side chains separate these two cavities in MAO Correspondence B. To probe the function of these gating residues, Ile199Ala and Ile199Ala- D. E. Edmondson, Department of Tyr326Ala mutant forms of MAO B were investigated. Structural data on Biochemistry, Emory University, 1510 the Ile199Ala MAO B mutant show no alterations in active site geometries Clifton Road, Atlanta, GA 30322, USA compared with wild-type enzyme while the Ile199Ala-Tyr326Ala MAO B Fax: +1 404 727 2738 mutant exhibits alterations in residues 100–103 which are part of the loop Tel: +1 404 727 5972 gating the entrance to the active site. Both mutant enzymes exhibit catalytic E-mail: [email protected] properties with increased amine KM but unaltered kcat values. The altered *Present address KM values on mutation are attributed to the influence of the cavity struc- Department of Chemistry, Princeton ture in the binding and subsequent deprotonation of the amine substrate.
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  • Regulation of Brain Reward by the Endocannabinoid System: a Critical Review of Behavioral Studies in Animals
    Send Orders for Reprints to [email protected] Current Pharmaceutical Design, 2014, 20, 000-000 1 Regulation of Brain Reward by the Endocannabinoid System: A Critical Review of Behavioral Studies in Animals S. Vlachou2 and G. Panagis1,* 1Laboratory of Behavioral Neuroscience, Department of Psychology, School of Social Sciences, University of Crete, 74100 Rethym- non, Crete, Greece; 2School of Nursing and Human Sciences, Faculty of Science and Health, Dublin City University, Glasnevin, Dub- lin 9, Ireland Abstract: The endocannabinoid system has been implicated in the regulation of a variety of physiological processes, including a crucial involvement in brain reward systems and the regulation of motivational processes. Behavioral studies have shown that cannabinoid re- ward may involve the same brain circuits and similar brain mechanisms with other drugs of abuse, such as nicotine, cocaine, alcohol and heroin, as well as natural rewards, such as food, water and sucrose, although the conditions under which cannabinoids exert their reward- ing effects may be more limited. The purpose of the present review is to briefly describe and evaluate the behavioral and pharmacological research concerning the major components of the endocannabinoid system and reward processes. Special emphasis is placed on data re- ceived from four procedures used to test the effects of the endocannabinoid system on brain reward in animals; namely, the intracranial self-stimulation paradigm, the self-administration procedure, the conditioned place preference procedure and the drug-discrimination pro- cedure. The effects of cannabinoid 1 (CB1) and cannabinoid 2 (CB2) receptor agonists, antagonists and endocannabinoid modulators in these procedures are examined. Further, the involvement of CB1 and CB2 receptors, as well the fatty acid amid hydrolase (FAAH) en- zyme in reward processes is investigated through presentation of respective genetic ablation studies in mice.
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  • Parkinson Disease and Other Movement Disorders
    P1: Trim: 8.375in × 10.875in Top: 0.373in Gutter: 0.664in LWBK915-57 LWW-KodaKimble-educational September 17, 2011 2:31 Parkinson Disease and Other 57 Movement Disorders Michael E. Ernst and Mildred D. Gottwald CORE PRINCIPLES CHAPTER CASES PARKINSON DISEASE 1 Parkinson disease (PD) is a chronic, progressive movement disorder resulting from Case 57-1 (Questions 1, 2) loss of dopamine from the nigrostriatal tracts in the brain, and is characterized by rigidity, bradykinesia, postural disturbances, and tremor. 2 Treatment for PD is aimed at restoring dopamine supply through one, or a Case 57-1 combination, of the following methods: exogenous dopamine in the form of a (Questions 3–18), precursor, levodopa; direct stimulation of dopamine receptors via dopamine Case 57-2 (Questions 1, 2) agonists; and inhibition of metabolic pathways responsible for degradation of levodopa. 3 Therapy for PD is usually delayed until there is a significant effect on quality of life; Case 57-1 (Questions 4, 10) generally younger patients start with dopamine agonists, whereas older patients may start with levodopa. 4 Initial therapy with dopamine agonists is associated with a lower risk of developing Case 57-1 (Questions 4, motor complications than with levodopa, but all patients will eventually require 10–15) levodopa. 5 Advanced PD is characterized by motor fluctuations including a gradual decline in Case 57-1 (Questions on time, and the development of troubling dopaminergic-induced dyskinesias. 15–18), Case 57-2 Dopamine agonists, monoamine oxidase type B (MAO-B) inhibitors, and (Question 1), Case 57-3 catechol-O-methyltransferase (COMT) inhibitors can reduce motor fluctuations; (Questions 1, 2) amantadine can improve dyskinesias.
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  • Comprehensive Review on the Interaction Between Natural Compounds and Brain Receptors: Benefits and Toxicity
    European Journal of Medicinal Chemistry 174 (2019) 87e115 Contents lists available at ScienceDirect European Journal of Medicinal Chemistry journal homepage: http://www.elsevier.com/locate/ejmech Review article Comprehensive review on the interaction between natural compounds and brain receptors: Benefits and toxicity * Ana R. Silva a, Clara Grosso b, , Cristina Delerue-Matos b,Joao~ M. Rocha a, c a Centre of Molecular and Environmental Biology (CBMA), Department of Biology (DB), University of Minho (UM), Campus Gualtar, P-4710-057, Braga, Portugal b REQUIMTE/LAQV, Instituto Superior de Engenharia do Instituto Politecnico do Porto, Rua Dr. Antonio Bernardino de Almeida, 431, P-4249-015, Porto, Portugal c REQUIMTE/LAQV, Grupo de investigaçao~ de Química Organica^ Aplicada (QUINOA), Laboratorio de polifenois alimentares, Departamento de Química e Bioquímica (DQB), Faculdade de Ci^encias da Universidade do Porto (FCUP), Rua do Campo Alegre, s/n, P-4169-007, Porto, Portugal article info abstract Article history: Given their therapeutic activity, natural products have been used in traditional medicines throughout the Received 6 December 2018 centuries. The growing interest of the scientific community in phytopharmaceuticals, and more recently Received in revised form in marine products, has resulted in a significant number of research efforts towards understanding their 10 April 2019 effect in the treatment of neurodegenerative diseases, such as Alzheimer's (AD), Parkinson (PD) and Accepted 11 April 2019 Huntington (HD). Several studies have shown that many of the primary and secondary metabolites of Available online 17 April 2019 plants, marine organisms and others, have high affinities for various brain receptors and may play a crucial role in the treatment of diseases affecting the central nervous system (CNS) in mammalians.
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  • NIDA Drug Supply Program Catalog, 25Th Edition
    RESEARCH RESOURCES DRUG SUPPLY PROGRAM CATALOG 25TH EDITION MAY 2016 CHEMISTRY AND PHARMACEUTICS BRANCH DIVISION OF THERAPEUTICS AND MEDICAL CONSEQUENCES NATIONAL INSTITUTE ON DRUG ABUSE NATIONAL INSTITUTES OF HEALTH DEPARTMENT OF HEALTH AND HUMAN SERVICES 6001 EXECUTIVE BOULEVARD ROCKVILLE, MARYLAND 20852 160524 On the cover: CPK rendering of nalfurafine. TABLE OF CONTENTS A. Introduction ................................................................................................1 B. NIDA Drug Supply Program (DSP) Ordering Guidelines ..........................3 C. Drug Request Checklist .............................................................................8 D. Sample DEA Order Form 222 ....................................................................9 E. Supply & Analysis of Standard Solutions of Δ9-THC ..............................10 F. Alternate Sources for Peptides ...............................................................11 G. Instructions for Analytical Services .........................................................12 H. X-Ray Diffraction Analysis of Compounds .............................................13 I. Nicotine Research Cigarettes Drug Supply Program .............................16 J. Ordering Guidelines for Nicotine Research Cigarettes (NRCs)..............18 K. Ordering Guidelines for Marijuana and Marijuana Cigarettes ................21 L. Important Addresses, Telephone & Fax Numbers ..................................24 M. Available Drugs, Compounds, and Dosage Forms ..............................25
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  • Essential Oil Characterization of Thymus Vulgaris from Various Geographical Locations
    foods Article Essential Oil Characterization of Thymus vulgaris from Various Geographical Locations Prabodh Satyal 1,2, Brittney L. Murray 2, Robert L. McFeeters 2 and William N. Setzer 2,* 1 Alchemy Aromatic LLC, 621 Park East Blvd., New Albany, IN 47150, USA; [email protected] 2 Department of Chemistry, University of Alabama in Huntsville, Huntsville, AL 35899, USA; [email protected] (B.L.M.); [email protected] (R.L.M.) * Correspondence: [email protected]; Tel.: +1-256-824-6519 Academic Editor: Angel A. Carbonell-Barrachina Received: 1 September 2016; Accepted: 24 October 2016; Published: 27 October 2016 Abstract: Thyme (Thymus vulgaris L.) is a commonly used flavoring agent and medicinal herb. Several chemotypes of thyme, based on essential oil compositions, have been established, including (1) linalool; (2) borneol; (3) geraniol; (4) sabinene hydrate; (5) thymol; (6) carvacrol, as well as a number of multiple-component chemotypes. In this work, two different T. vulgaris essential oils were obtained from France and two were obtained from Serbia. The chemical compositions were determined using gas chromatography–mass spectrometry. In addition, chiral gas chromatography was used to determine the enantiomeric compositions of several monoterpenoid components. The T. vulgaris oil from Nyons, France was of the linalool chemotype (linalool, 76.2%; linalyl acetate, 14.3%); the oil sample from Jablanicki, Serbia was of the geraniol chemotype (geraniol, 59.8%; geranyl acetate, 16.7%); the sample from Pomoravje District, Serbia was of the sabinene hydrate chemotype (cis-sabinene hydrate, 30.8%; trans-sabinene hydrate, 5.0%); and the essential oil from Richerenches, France was of the thymol chemotype (thymol, 47.1%; p-cymene, 20.1%).
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