DOCSLIB.ORG

Natural Products in Chemical Biology Natural Products in Chemical Biology

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Natural Products in Chemical Biology Natural Products in Chemical Biology NATURAL PRODUCTS IN CHEMICAL BIOLOGY NATURAL PRODUCTS IN CHEMICAL BIOLOGY Edited by NATANYA CIVJAN A JOHN WILEY & SONS, INC., PUBLICATION Copyright © 2012 by John Wiley & Sons, Inc. All rights reserved Published by John Wiley & Sons, Inc., Hoboken, New Jersey Published simultaneously in Canada No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, recording, scanning, or otherwise, except as permitted under Section 107 or 108 of the 1976 United States Copyright Act, without either the prior written permission of the Publisher, or authorization through payment of the appropriate per-copy fee to the Copyright Clearance Center, Inc., 222 Rosewood Drive, Danvers, MA 01923, (978) 750-8400, fax (978) 750-4470, or on the web at www.copyright.com.Requests to the Publisher for permission should be addressed to the Permissions Department, John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030, (201) 748-6011, fax (201) 748-6008, or online at http://www.wiley.com/go/permission. Limit of Liability/Disclaimer of Warranty: While the publisher and author have used their best efforts in preparing this book, they make no representations or warranties with respect to the accuracy or completeness of the contents of this book and specifically disclaim any implied warranties of merchantability or fitness for a particular purpose. No warranty may be created or extended by sales representatives or written sales materials. The advice and strategies contained herein may not be suitable for your situation. You should consult with a professional where appropriate. Neither the publisher nor author shall be liable for any loss of profit or any other commercial damages, including but not limited to special, incidental, consequential, or other damages. For general information on our other products and services or for technical support, please contact our Customer Care Department within the United States at (800) 762-2974, outside the United States at (317) 572-3993 or fax (317) 572-4002. Wiley also publishes its books in a variety of electronic formats. Some content that appears in print may not be available in electronic formats. For more information about Wiley products, visit our web site at www.wiley.com. Library of Congress Cataloging-in-Publication Data: Natural products in chemical biology / edited by Natanya Civjan. p. cm. Includes bibliographical references and index. ISBN 978-1-118-10117-9 (hardback) 1. Biological products. 2. Natural products. 3. Biochemistry. I. Civjan, Natanya. QH345.N3466 2012 572–dc23 2011049643 Printed in the United States of America 10987654321 CONTENTS Preface vii Contributors ix PART I CHEMICAL DIVERSITY OF NATURAL PRODUCTS 1 1 Plant Natural Products 3 A. Leslie Gunatilaka 2 Marine Natural Products 31 Nobuhiro Fusetani 3 Microbial Natural Products 65 Sergio Sanchez, Silvia Guzm´an-Trampe, Mariana Avalos,´ Beatriz Ruiz, Romina Rodr´ıguez-Sanoja, and Manuel Jim´enez-Estrada PART II BIOSYNTHESIS OF NATURAL PRODUCTS 109 4 Nonribosomal Peptides 111 Georg Schoenafinger and Mohamed A. Marahiel 5 Plant Terpenoids 127 Christopher I. Keeling and J¨org Bohlmann v vi CONTENTS 6 Polyketides in Fungi 143 Thomas J. Simpson and Russell J. Cox 7 Modular Polyketide Synthases 163 Tonia J. Buchholz, Jeffrey D. Kittendorf, and David H. Sherman 8 Polyketide Polyethers 189 Alison M. Hill 9 Alkaloids 209 Sarah E. O’Connor 10 Cofactors 239 Ilka Haase, Markus Fischer, Adelbert Bacher, Wolfgang Eisenreich, and Felix Rohdich 11 Antibiotics 269 Sergey B. Zotchev PART III NATURAL PRODUCTS IN MEDICINE 287 12 Pharmaceuticals: Natural Products and Natural Product Models 289 Sheo B. Singh 13 Natural Products as Anticancer Agents 325 DavidG.I.KingstonandDavidJ.Newman 14 Plant-Derived Natural Products Research in Drug Discovery 351 Kuo-Hsiung Lee, Hideji Itokawa, Toshiyuki Akiyama, and Susan L. Morris-Natschke Index 389 PREFACE Natural products have long been of interest to the fields of chemistry, biology, and medicine, because of their immense molecular diversity, biological activities, and medicinal properties. Interdisciplinary studies have yielded further insights into the ecological significance, biological roles, and therapeutic potential of these important molecules. Containing carefully selected reprints from the award-winning Wiley Ency- clopedia of Chemical Biology as well as new contributions, this book features a collection of chapters on topics in natural products research. The chapters cover the diversity of natural products in plants, marine invertebrates, and microbes, the biosynthetic pathways of some major classes of natural products, and the role of natural products in drug discovery and medicine. Written by prominent scholars, this book will be of interest to advanced students and researchers, both in academia and industry, entering the field of chemical biology or related fields such as biochemistry, medicine, and pharma- ceutical sciences. Natanya Civjan vii CONTRIBUTORS Toshiyuki Akiyama, Natural Products Research Laboratories, School of Phar- macy, University of North Carolina, Chapel Hill, North Carolina Mariana Avalos,´ Instituto de Investigaciones Biomedicas,´ Universidad Nacional Autonoma´ de Mexico,´ Mexico´ Adelbert Bacher, Institute of Biochemistry, Department Chemie, Technische Universitat¨ Munchen,¨ Munchen,¨ Germany Jorg¨ Bohlmann, Michael Smith Laboratories and Departments of Botany and Forest Sciences, University of British Columbia, British Columbia, Canada Tonia J. Buchholz, Life Sciences Institute, University of Michigan, Ann Arbor, Michigan Russell J. Cox, School of Chemistry, University of Bristol, Bristol, United Kingdom Wolfgang Eisenreich, Institute of Biochemistry, Department Chemie, Technische Universitat¨ Munchen,¨ Munchen,¨ Germany Markus Fischer, Institute of Food Chemistry, University of Hamburg, Hamburg, Germany Nobuhiro Fusetani, Hokkaido University, Hakodate, Japan A. Leslie Gunatilaka, Southwest Center for Natural Products Research, Univer- sity of Arizona, Tucson, Arizona Silvia Guzman-Trampe,´ Instituto de Investigaciones Biomedicas,´ Universidad Nacional Autonoma´ de Mexico,´ Mexico´ Ilka Haase, Institute of Food Chemistry, University of Hamburg, Hamburg, Germany ix x CONTRIBUTORS Alison M. Hill, School of Biosciences, University of Exeter, United Kingdom Hideji Itokawa, Natural Products Research Laboratories, School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina Manuel Jimenez-Estrada,´ Instituto de Qu´ımica, Universidad Nacional Autonoma´ de, Mexico´ Christopher I. Keeling, Michael Smith Laboratories, University of British Columbia, British Columbia, Canada David G. I. Kingston, Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg, Virginia Jeffrey D. Kittendorf, University of Michigan, Ann Arbor, Michigan Kuo-Hsiung Lee, Natural Products Research Laboratories, School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina Mohamed A. Marahiel, Philipps-University of Marburg, FB Chemie/Biochemie, Marburg, Germany Susan L. Morris-Natschke, Natural Products Research Laboratories, School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina David J. Newman, Natural Products Branch, Developmental Therapeutics Pro- gram, Division of Cancer Treatment and Diagnosis, National Cancer Institute, Frederick, Maryland Sarah E. O’Connor, John Innes Centre, Norwich Research Park, Colney, Nor- wich Romina Rodr´ıguez-Sanoja, Instituto de Investigaciones Biomedicas,´ Universi- dad Nacional Autonoma´ de Mexico,´ Mexico´ Felix Rohdich, Institute of Biochemistry, Department Chemie, Technische Universitat¨ Munchen,¨ Munchen,¨ Germany Beatriz Ruiz, Instituto de Investigaciones Biomedicas,´ Universidad Nacional Autonoma´ de Mexico,´ Mexico´ Georg Schoenafinger, Philipps-University of Marburg, FB Chemie/Biochemie, Marburg, Germany Sergio Sanchez, Instituto de Investigaciones Biomedicas,´ Universidad Nacional Autonoma´ de Mexico,´ Mexico´ David H. Sherman, University of Michigan, Ann Arbor, Michigan Thomas J. Simpson, School of Chemistry, University of Bristol, Bristol, United Kingdom Sheo B. Singh, Merck Research Laboratories, Rahway, New Jersey Sergey B. Zotchev, Department of Biotechnology, Norwegian University of Science and Technology, Norway PART I CHEMICAL DIVERSITY OF NATURAL PRODUCTS 1 PLANT NATURAL PRODUCTS A. Leslie Gunatilaka Southwest Center for Natural Products Research, University of Arizona, Tucson, Arizona Plants contain numerous natural products (secondary metabolites) that may not partic- ipate directly in their growth and development but play an important role in ecological interactions with other organisms. Despite immense chemical diversity, which orig- inates from simple carbohydrates produced because of photosynthesis, plant natural products are formed from only a few biosynthetic building blocks that consist of acetate, mevalonate, and shikimate. These basic building blocks undergo a variety of biosynthetic transformations and combinations that lead to numerous classes of plant natural products including, but not limited to, carbohydrates, fatty acids and their esters, aromatic polyketides (phenols and quinones), terpenoids and steroids, phenyl propanoids (lignans and lignin, coumarins, flavonoids, and isoflavonoids), and alkaloids. Summarized in this chapter are representative members of these important classes of plant natural products with special emphasis on their chemical diversity. The chapter concludes
Load more

Recommended publications
  • 2354 Metabolism and Ecology of Purine Alkaloids Ana Luisa Anaya 1
    [Frontiers in Bioscience 11, 2354-2370, September 1, 2006] Metabolism and Ecology of Purine Alkaloids Ana Luisa Anaya 1, Rocio Cruz-Ortega 1 and George R. Waller 2 1Departamento de Ecologia Funcional, Instituto de Ecologia, Universidad Nacional Autonoma de Mexico. Mexico DF 04510, 2Department of Biochemistry and Molecular Biology, Oklahoma State University. Stillwater, OK 74078, USA TABLE OF CONTENTS 1. Abstract 2. Introduction 3. Classification of alkaloids 4. The importance of purine in natural compounds 5. Purine alkaloids 5.1. Distribution of purine alkaloids in plants 5.2. Metabolism of purine alkaloids 6. Biosynthesis of caffeine 6.1. Purine ring methylation 6.2. Cultured cells 7. Catabolism of caffeine 8. Caffeine-free and low caffeine varieties of coffee 8.1. Patents 9. Ecological role of alkaloids 9.1. Herbivory 9.2. Allelopathy 9.2.1. Mechanism of action of caffeine and other purine alkaloids in plants 10. Perspective 11. Acknowledgements 12. References 1. ABSTRACT 2. INTRODUCTION In this review, the biosynthesis, catabolism, Alkaloids are one of the most diverse groups of ecological significance, and modes of action of purine secondary metabolites found in living organisms. They alkaloids particularly, caffeine, theobromine and have many distinct types of structure, metabolic pathways, theophylline in plants are discussed. In the biosynthesis of and ecological and pharmacological activities. Many caffeine, progress has been made in enzymology, the amino alkaloids have been used in medicine for centuries, and acid sequence of the enzymes, and in the genes encoding some are still important drugs. Alkaloids have, therefore, N-methyltransferases. In addition, caffeine-deficient plants been prominent in many scientific fields for years, and have been produced.
    [Show full text]
  • Title Total Biosynthesis of Opiates by Stepwise Fermentation Using
    Total biosynthesis of opiates by stepwise fermentation using Title engineered Escherichia coli. Nakagawa, Akira; Matsumura, Eitaro; Koyanagi, Takashi; Katayama, Takane; Kawano, Noriaki; Yoshimatsu, Kayo; Author(s) Yamamoto, Kenji; Kumagai, Hidehiko; Sato, Fumihiko; Minami, Hiromichi Citation Nature communications (2016), 7 Issue Date 2016-02-05 URL http://hdl.handle.net/2433/204378 This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in the credit line; Right if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/ Type Journal Article Textversion publisher Kyoto University ARTICLE Received 30 Oct 2015 | Accepted 7 Dec 2015 | Published 5 Feb 2016 DOI: 10.1038/ncomms10390 OPEN Total biosynthesis of opiates by stepwise fermentation using engineered Escherichia coli Akira Nakagawa1, Eitaro Matsumura1, Takashi Koyanagi1, Takane Katayama2, Noriaki Kawano3, Kayo Yoshimatsu3, Kenji Yamamoto1, Hidehiko Kumagai1, Fumihiko Sato4 & Hiromichi Minami1 Opiates such as morphine and codeine are mainly obtained by extraction from opium poppies. Fermentative opiate production in microbes has also been investigated, and complete biosynthesis of opiates from a simple carbon source has recently been accom- plished in yeast. Here we demonstrate that Escherichia coli serves as an efficient, robust and flexible platform for total opiate synthesis. Thebaine, the most important raw material in opioid preparations, is produced by stepwise culture of four engineered strains at yields of 2.1 mg l À 1 from glycerol, corresponding to a 300-fold increase from recently developed yeast systems.
    [Show full text]
  • Pharmacokinetic Interactions Between Herbal Medicines and Drugs: Their Mechanisms and Clinical Relevance
    life Review Pharmacokinetic Interactions between Herbal Medicines and Drugs: Their Mechanisms and Clinical Relevance Laura Rombolà 1 , Damiana Scuteri 1,2 , Straface Marilisa 1, Chizuko Watanabe 3, Luigi Antonio Morrone 1, Giacinto Bagetta 1,2,* and Maria Tiziana Corasaniti 4 1 Preclinical and Translational Pharmacology, Department of Pharmacy, Health and Nutritional Sciences, Section of Preclinical and Translational Pharmacology, University of Calabria, 87036 Rende, Italy; [email protected] (L.R.); [email protected] (D.S.); [email protected] (S.M.); [email protected] (L.A.M.) 2 Pharmacotechnology Documentation and Transfer Unit, Preclinical and Translational Pharmacology, Department of Pharmacy, Health and Nutritional Sciences, University of Calabria, 87036 Rende, Italy 3 Department of Physiology and Anatomy, Tohoku Pharmaceutical University, 981-8558 Sendai, Japan; [email protected] 4 School of Hospital Pharmacy, University “Magna Graecia” of Catanzaro and Department of Health Sciences, University “Magna Graecia” of Catanzaro, 88100 Catanzaro, Italy; [email protected] * Correspondence: [email protected]; Tel.: +39-0984-493462 Received: 28 May 2020; Accepted: 30 June 2020; Published: 4 July 2020 Abstract: The therapeutic efficacy of a drug or its unexpected unwanted side effects may depend on the concurrent use of a medicinal plant. In particular, constituents in the medicinal plant extracts may influence drug bioavailability, metabolism and half-life, leading to drug toxicity or failure to obtain a therapeutic response. This narrative review focuses on clinical studies improving knowledge on the ability of selected herbal medicines to influence the pharmacokinetics of co-administered drugs. Moreover, in vitro studies are useful to anticipate potential herbal medicine-drug interactions.
    [Show full text]
  • “Biosynthesis of Morphine in Mammals”
    “Biosynthesis of Morphine in Mammals” D i s s e r t a t i o n zur Erlangung des akademischen Grades Doctor rerum naturalium (Dr. rer. nat.) vorgelegt der Naturwissenschaftlichen Fakultät I Biowissenschaften der Martin-Luther-Universität Halle-Wittenberg von Frau Nadja Grobe geb. am 21.08.1981 in Querfurt Gutachter /in 1. 2. 3. Halle (Saale), Table of Contents I INTRODUCTION ........................................................................................................1 II MATERIAL & METHODS ........................................................................................ 10 1 Animal Tissue ....................................................................................................... 10 2 Chemicals and Enzymes ....................................................................................... 10 3 Bacteria and Vectors ............................................................................................ 10 4 Instruments ........................................................................................................... 11 5 Synthesis ................................................................................................................ 12 5.1 Preparation of DOPAL from Epinephrine (according to DUNCAN 1975) ................. 12 5.2 Synthesis of (R)-Norlaudanosoline*HBr ................................................................. 12 5.3 Synthesis of [7D]-Salutaridinol and [7D]-epi-Salutaridinol ..................................... 13 6 Application Experiments .....................................................................................
    [Show full text]
  • WO 2015/095882 Al 25 June 2015 (25.06.2015) W P O P C T
    (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2015/095882 Al 25 June 2015 (25.06.2015) W P O P C T (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every C12Q 1/68 (2006.0 1) C12Q 1/70 (2006.0 1) kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, (21) International Application Number: BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, PCT/US20 14/07 1963 DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (22) International Filing Date: HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, 22 December 2014 (22. 12.2014) KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, (25) Filing Language: English PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, (26) Publication Language: English SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (30) Priority Data: 61/ 19,663 20 December 201 3 (20. 12.20 13) US (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, (71) Applicant: THE REGENTS OF THE UNIVERSITY GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, OF CALIFORNIA [US/US]; 1111 Franklin Street, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, Twelfth Floor, Oakland, CA 94607-5200 (US).
    [Show full text]
  • EARTH Title Description ENTITIES ATTRIBUTES DYNAMIC ASPECTS
    EARTH Title Description ENTITIES ATTRIBUTES DYNAMIC ASPECTS DIMENSIONS ACCESSORY TERMS <EFFECTS AND SINGLE EVENTS> <STRUCTURE AND MORPHOLOGY> ACTIVITIES COMPOSITION CONDITIONS GENERAL TERMS IMMATERIAL ENTITIES MATERIAL ENTITIES PROCESSES PROPERTIES TIME <ABIOTIC ENVIRONMENT PROCESSES> <BIOECOLOGICAL PROCESSES> <COGNITIVE PROCESSES> <COMPLEX> <MENTAL CONSTRUCTS> <PHYSICAL AND CHEMICAL PROCESSES> <PHYSICAL OPERATIONS> <POLICY ACTIVITIES> <PROCESSES OF COMPLEX SYSTEMS (BY GENERAL TYPE)> <PROCESSES RELATED TO MATERIALS AND PRODUCTS> <PRODUCTIVE SECTORS> <SOCIAL AND CULTURAL ACTIVITIES> <SOCIAL, CULTURAL AND POLICY PROCESSES> INDUSTRY LIVING ENTITIES NON LIVING ENTITIES <ABSTRACT CONCEPTS AND PRINCIPLES> <DISPOSAL AND RESTORATION> <KNOWLEDGE SYSTEMS> <MANIPULATION, PRODUCTION, CONSUMPTION> <MEASURES> <METHODS AND TECHNIQUES> <PARAMETERS, CRITERIA AND FACTORS> <REPRESENTATION AND ELABORATION SYSTEMS> ARTIFICIAL ENTITIES BIOECOLOGICAL ENTITIES DATA NATURAL ENTITIES NATURAL SPACES BY GENERAL TYPES SOCIAL ENTITIES <ABIOTIC ENVIRONMENT> <BUILT ENVIRONMENT> <EARTH CONSTITUENTS AND MATERIALS> <MATERIALS AND PRODUCTS> <OPEN SPACES, CULTURAL LANDSCAPES> <PARTS> <PHYSICAL AND CHEMICAL CONSTITUENTS> <WHOLE> EQUIPMENT AND TECHNOLOGICAL SYSTEMS symbiotic organisms technological systems <ATMOSPHERE ENVIRONMENT> <ECOSYSTEM ABIOTIC COMPONENTS> <EXTRATERRESTRIAL ENVIRONMENT> <GEOGRAPHICAL REGIONS AND CLIMATIC ZONES> <TERRESTRIAL ENVIRONMENT> <WATER ENVIRONMENT> <CONTINENTAL WATER ENVIRONMENT> <OCEANIC WATER ENVIRONMENT> <TERRESTRIAL AREAS AND LANDFORMS> geological
    [Show full text]
  • Coptis Japonica</Emphasis>
    Plant Cell Reports (1988) 7:1-4 Plant Cell Reports © Springer-Verlag 1988 Alternative final steps in berberine biosynthesis in Coptisjaponica cell cultures E. Galneder 1 M. Rueffer 1, G. Wanner 1, 2, M. Tabata 1, 3, and M. H. Zenk 1 1 Lehrstuhl tar Pharmazeutische Biologie der Universitfit Mfinchen, Karlstrasse 29, D-8000 Mt~nchen 2, Federal Republic of Germany 2 Botanisches Institut der Universitfit Miinchen, Menzinger Strasse 67, D-8000 Manchen 19, Federal Republic of Germany 3 Faculty of Pharmaceutical Sciences, Kyoto University, Kyoto 606, Japan Received October 30, 1987 - Communicated by K. Hahlbrock ABSTRACT oxidase (STOX) reported from our laboratory (Amann et al., 1984) in that the Coptis enzyme dehydrogenated In Coptis japonica cell cultures an alternative path- only (S)-canadine while other tetrahydroprotober- way has been discovered which leads from (S)-tetra- berines were reported to be inactive. In further hydrocolumbamine via (S)-canadine to berberine. The contrast to the STOX enzyme, their enzyme did not two enzymes involved have been partially purified. produce hydrogen peroxide but rather H20 as one of (S)-Tetrahydrocolumbamine is stereospecifically the reaction products. Our analysis of the Coptis transformed into (S)-canadine under formation of the system reported here led to the surprising result methylenedioxy bridge in ring A. This new enzyme was that the terminal two steps in the biosynthesis of named (S)-canad/ne synthase. (S)-Canadine in turn is berberine in 8erberis and Coptis are biochemically stereospecifically dehydrogenated to berberine by an completely different while similar at the cytological oxidase, (S)-canadine oxidase (COX), which was level.
    [Show full text]
  • Discovery and Protein Engineering of Baeyer-Villiger Monooxygenases
    Discovery and Protein Engineering of Baeyer-Villiger monooxygenases Inauguraldissertation zur Erlangung des akademischen Grades eines Doktors der Naturwissenschaften (Dr. rer. nat.) der Mathematisch-Naturwissenschaftlichen Fakultät der Ernst-Moritz-Arndt-Universität Greifswald vorgelegt von Andy Beier geboren am 11.10.1988 in Parchim Greifswald, den 02.08.2017 I Dekan: Prof. Dr. Werner Weitschies 1. Gutachter: Prof. Dr. Uwe T. Bornscheuer 2. Gutachter: Prof. Dr. Marko Mihovilovic Tag der Promotion: 24.10.2017 II We need to learn to want what we have, not to have what we want, in order to get stable and steady happiness. - The Dalai Lama - III List of abbreviations % Percent MPS Methyl phenyl sulfide % (v/v) % volume per volume MPSO Methyl phenyl sulfoxide % (w/v) % weight per volume MPSO2 Methyl phenyl sulfone °C Degrees Celsius MTS Methyl p-tolyl sulfide µM µmol/L MTSO Methyl p-tolyl sulfoxide aa Amino acids MTSO2 Methyl p-tolyl sulfone + AGE Agarose gel electrophoresis NAD Nicotinamide adenine dinucleotide, oxidized aq. dest. Distilled water NADH Nicotinamide adenine dinucleotide, reduced + BLAST Basic Local Alignment Search NADP Nicotinamide adenine dinucleotide Tool phosphate, oxidized bp Base pair(s) NADPH Nicotinamide adenine dinucleotide phosphate, reduced BVMO Baeyer-Villiger monooxyge- OD600 Optical density at 600 nm nase CHMO Cyclohexanone monooxyge- PAGE Polyacrylamide gel electrophoresis nase Da Dalton PAMO Phenylacetone monooxygenase DMF Dimethyl formamide PCR Polymerase chain reaction DMSO Dimethyl sulfoxide PDB Protein Data Bank DMSO2 Dimethyl sulfone rpm Revolutions per minute DNA Desoxyribonucleic acid rv Reverse dNTP Desoxynucleoside triphosphate SDS Sodium dodecyl sulfate E. coli Escherichia coli SOC Super Optimal broth with Catabolite repression ee Enantiomeric excess TAE TRIS-Acetate-EDTA FAD Flavin adenine dinucleotide TB Terrific broth Fig.
    [Show full text]
  • The Phytochemistry of Cherokee Aromatic Medicinal Plants
    medicines Review The Phytochemistry of Cherokee Aromatic Medicinal Plants William N. Setzer 1,2 1 Department of Chemistry, University of Alabama in Huntsville, Huntsville, AL 35899, USA; [email protected]; Tel.: +1-256-824-6519 2 Aromatic Plant Research Center, 230 N 1200 E, Suite 102, Lehi, UT 84043, USA Received: 25 October 2018; Accepted: 8 November 2018; Published: 12 November 2018 Abstract: Background: Native Americans have had a rich ethnobotanical heritage for treating diseases, ailments, and injuries. Cherokee traditional medicine has provided numerous aromatic and medicinal plants that not only were used by the Cherokee people, but were also adopted for use by European settlers in North America. Methods: The aim of this review was to examine the Cherokee ethnobotanical literature and the published phytochemical investigations on Cherokee medicinal plants and to correlate phytochemical constituents with traditional uses and biological activities. Results: Several Cherokee medicinal plants are still in use today as herbal medicines, including, for example, yarrow (Achillea millefolium), black cohosh (Cimicifuga racemosa), American ginseng (Panax quinquefolius), and blue skullcap (Scutellaria lateriflora). This review presents a summary of the traditional uses, phytochemical constituents, and biological activities of Cherokee aromatic and medicinal plants. Conclusions: The list is not complete, however, as there is still much work needed in phytochemical investigation and pharmacological evaluation of many traditional herbal medicines. Keywords: Cherokee; Native American; traditional herbal medicine; chemical constituents; pharmacology 1. Introduction Natural products have been an important source of medicinal agents throughout history and modern medicine continues to rely on traditional knowledge for treatment of human maladies [1]. Traditional medicines such as Traditional Chinese Medicine [2], Ayurvedic [3], and medicinal plants from Latin America [4] have proven to be rich resources of biologically active compounds and potential new drugs.
    [Show full text]
  • Effects of the Putative Antipsychotic Alstonine on Glutamate Uptake in Acute Hippocampal Slices ⇑ Ana P
    Neurochemistry International 61 (2012) 1144–1150 Contents lists available at SciVerse ScienceDirect Neurochemistry International journal homepage: www.elsevier.com/locate/nci Effects of the putative antipsychotic alstonine on glutamate uptake in acute hippocampal slices ⇑ Ana P. Herrmann a,b, , Paula Lunardi b, Luísa Klaus Pilz a, Ana C. Tramontina b, Viviane M. Linck a,b, Christopher O. Okunji c, Carlos A. Gonçalves b, Elaine Elisabetsky a,b a Laboratório de Etnofarmacologia, Departamento de Farmacologia, Instituto de Ciências Básicas da Saúde, Universidade Federal do Rio Grande do Sul, Rua Sarmento Leite, 500, 90050-170 Porto Alegre, RS, Brazil b Programa de Pós-graduação em Ciências Biológicas: Bioquímica, Instituto de Ciências Básicas da Saúde, Universidade Federal do Rio Grande do Sul, Rua Ramiro Barcelos, 2600, 90035-000 Porto Alegre, RS, Brazil c International Centre for Ethnomedicine and Drug Development (InterCEDD), Nsukka, Enugu State, Nigeria article info abstract Article history: A dysfunctional glutamatergic system is thought to be central to the negative symptoms and cognitive Received 8 March 2012 deficits recognized as determinant to the poor quality of life of people with schizophrenia. Modulating Received in revised form 13 August 2012 glutamate uptake has, thus, been suggested as a novel target for antipsychotics. Alstonine is an indole Accepted 15 August 2012 alkaloid sharing with atypical antipsychotics the profile in animal models relevant to schizophrenia, Available online 25 August 2012 though divergent in its mechanism of action. The aim of this study was to evaluate the effects of alstonine on glutamate uptake. Additionally, the effects on glutathione content and extracellular S100B levels were Keywords: assessed.
    [Show full text]
  • (12) United States Patent (10) Patent No.: US 9,687,864 B2 Fulton Et Al
    USOO9687864B2 (12) United States Patent (10) Patent No.: US 9,687,864 B2 Fulton et al. (45) Date of Patent: Jun. 27, 2017 (54) SYSTEMAND METHOD FOR ENHANCED 428/25 (2015.01); Y10T 428/31504 (2015.04); ELECTROSTATIC DEPOSITION AND Y10T 428/31507 (2015.04); SURFACE COATINGS (Continued) (58) Field of Classification Search (71) Applicant: Battelle Memorial Institute, USPC .......... 118/620–640; 23.9/690 708; 427/458, Columbus, OH (US) 427/475 4.86 (72) Inventors: John L. Fulton, Richland, WA (US); See application file for complete search history. George S. Deverman, Richland, WA (US); Dean W. Matson, Kennewick, (56) References Cited CA (US); Clement R. Yonker, Kennewick, WA (US); C. Douglas U.S. PATENT DOCUMENTS Taylor, Franklinton, NC (US); James 3,087,860 A 4, 1963 Endicott B. McClain, Raleigh, NC (US); Joseph 3,123,077 A 3, 1964 Alcamo M. Crowley, Cambria, CA (US) (Continued) (73) Assignee: Battelle Memorial Institute, Columbus, OH (US) FOREIGN PATENT DOCUMENTS CA 2589761 12, 2004 (*) Notice: Subject to any disclaimer, the term of this CN 1465410 1, 2004 patent is extended or adjusted under 35 (Continued) U.S.C. 154(b) by 0 days. (21) Appl. No.: 14/310,960 OTHER PUBLICATIONS Abreu Filho et al., “Influence of metal alloy and the profile of (22) Filed: Jun. 20, 2014 coronary stents in patients with multi-vessel coronary disease.” Clinics 66(6):985-989 (2011). (65) Prior Publication Data (Continued) US 2015/OO40827 A1 Feb. 12, 2015 Related U.S. Application Data Primary Examiner — Yewebdar Tadesse (74) Attorney, Agent, or Firm — Lerner, David, (62) Division of application No.
    [Show full text]
  • Fused Tricyclic Dual Inhibitors of Cdk 4/6 and Flt3
    (19) TZZ ¥¥_T (11) EP 2 937 349 A1 (12) EUROPEAN PATENT APPLICATION (43) Date of publication: (51) Int Cl.: 28.10.2015 Bulletin 2015/44 C07D 471/14 (2006.01) C07D 519/00 (2006.01) A61K 31/519 (2006.01) A61P 35/00 (2006.01) (2006.01) (21) Application number: 15161337.9 A61P 35/02 (22) Date of filing: 21.03.2012 (84) Designated Contracting States: • Keegan, Kathleen S. AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Bainbridge Island, WA Washington 98110 (US) GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO • LI, Zhihong PL PT RO RS SE SI SK SM TR Millbrae, CA California 94030 (US) Designated Extension States: • Lively, Sarah E. BA ME San Carlos, CA California 94070 (US) • McGee, Lawrence R. (30) Priority: 23.03.2011 US 201161466841 P Pacifica, CA California 94044 (US) •Ragains,Mark L. (62) Document number(s) of the earlier application(s) in Fort Worth, TX Texas 76109 (US) accordance with Art. 76 EPC: • Wang, Xianghong 12711738.0 / 2 688 887 Dublin, CA California 94568 (US) • Weidner, Margaret F. (71) Applicant: AMGEN INC. Woodinville, WA Washington 98072 (US) Thousand Oaks, CA 91320-1799 (US) • Zhang, Jian Foster City, CA California 94404 (US) (72) Inventors: • Chen, Xiaoqi (74) Representative: Hoffmann Eitle Palo Alto, CA California 94303 (US) Patent- und Rechtsanwälte PartmbB •Dai,Kang Arabellastraße 30 Albany, CA California 94706 (US) 81925 München (DE) • Duquette, Jason A. Millbrae, CA California 94030 (US) Remarks: • Gribble, Michael W., Jr. This application was filed on 12-05-2015 as a San Francisco, CA California 94110 (US) divisional application to the application mentioned • Huard, Justin N.
    [Show full text]