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Alkaloid Chemistry in Biosynthesis, Models and Other Methodological Considerations and Basic Techniques Used

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Elsevier AMS Prelims-N52736 Job code: ASLA 17-2-2007 12:35p.m. Page:xi Trimsize:165×240MM List of Figures 1 Contemporary scheme of morphine. 2 2 Some alkaloids isolated by pharmaceutists Pierre Joseph Pelletier and Joseph Beinamé Caventou during 1817–1821. 3 3 Schemes of taxol, vinblastine, vincristine and vincamine 5 4 An example of a true alkaloid 11 5 An example of protoalkaloids 11 6 An example of a pseudoalkaloid 12 7 The raw extraction of quinolizidine alkaloids 13 8 l-tryptophan with its aromatic side chain 15 9 The devil’s-pepper genus, Rauwolfia serpentina 15 10 l-phenylalanine is a precursor 17 11 l-ornithine is an important precursor 19 12 l-tyrosine, with its aromatic side chain 19 13 l-anthranilic acid is a precursor 23 14 l-histidine is a precursor 24 15 l-ornithine and l-nicotinic acids are precursors 26 16 l-lysine is a precursor 31 17 (a) Structure of seed testa of the Washington lupine (b) Alkaloidal Lupinus polyphyllus Lindl. 32 18 Jervine, cyclopamine and protoveratrine structures. 49 19 Basic alkaloids of mushrooms. 55 20 Ergotamine and LSD 56 21 Secondary metabolism blocks 65 22 Pyruvate derivation and acetyl CoA synthesis 66 23 General scheme of alkaloid synthesis 68 24 l-lysine-derived nuclei 69 25 Nuclei and skeletons of izidine alkaloids 70 26 The source and forms of the pyrrolidine ring 70 27 l-histidine and the nuclei of imidazole and manzamine alkaloids. 70 28 The nuclei produced by anthranilic acid in alkaloids 71 29 The nucleus of alkaloids derived from nicotinic acid 72 30 l-phenylanine-derived nuclei in alkaloid biosynthesis 72 31 Nuclei supplied to alkaloids by l-tyrosine in the synthesizing process 73 32 The l-tryptophan-supplied nucleus during synthesis 74 33 Synthesis of alkaloids from ornithine 75 34 Synthesis pathway of the pyrrolizidine alkaloids 76 35 Synthesis of hordeine and mescaline 77 Font Used:Times Margins:Top:18mm Gutter:20mm Font Size:11/13 Text Width:125mm Depth:43 Lines Elsevier AMS Prelims-N52736 Job code: ASLA 17-2-2007 12:35p.m. Page:xii Trimsize:165×240MM xii List of Figures 36 Synthesis pathway of kreysigine and colchicine 77 37 Emetine and cephaeline synthesis pathway 78 38 Galanthamine synthesis pathway 79 39 Psilocybin and serotonin synthesis pathway 80 40 Scheme of elaeagnine, harman and harmine synthesis pathway 80 41 Pattern of the ajmalicine, tabersonine and catharanthine pathway 82 42 Diagram of the vindoline, vinblastine and vincristine pathway 82 43 Diagram of the strychnine and brucine pathway 83 44 Diagram of the quinine, quinidine and cinchonine synthesis pathway 84 45 Diagram of the eserine synthesis pathway 84 46 Diagram of the ergotamine synthesis pathway 85 47 Scheme of nicotine and nornicotine synthesis pathway 86 48 Diagram of anatabine, anabasine and ricinine synthesis pathway 86 49 Diagram of the pelletierine, lobelanine and piperine synthesis pathway 87 50 Diagram of the swansonine and castanospermine synthesis pathway 88 51 Diagram of the lupinine, sparteine, lupanine and cytisine synthesis pathway. 89 52 Structural development of piperidine alkaloids. 96 53 Structural development of indolizidine alkaloids. 97 54 Structural development of quinolizidine alkaloids. 99 55 Structural development of pyrrolizidine alkaloids. 102 56 Structural development of pyrrolidine alkaloids. 104 57 Structural development of tropane alkaloids. 105 58 Structural development of imidazole alkaloids. 106 59 Structural development of quinazoline alkaloid vasicine. 107 60 Structural development of acridone alkaloids. 108 61 Structural development of pyridine alkaloids. 109 62 Structural development of sesquiterpene pyridine alkaloids. 111 63 Structural development of phenyl and phenylpropyl alkaloids. 112 64 Structural development of simple indole alkaloids. 113 65 Structural development of carboline alkaloids. 114 66 Structural development of corynanthe alkaloids. 115 67 Structural development of iboga alkaloids. 116 68 Structural development of aspidosperma alkaloids. 117 69 Structural development of quinoline alkaloids. 118 70 Structural development of pyrroloindole alkaloids. 119 71 Structural development of ergot alkaloids. 120 72 Structural development of manzamine alkaloids. 121 73. Chemical explanation for alkaloid biogenesis in organisms. 123 74 Chemical model of indole alkaloid formation in Catharanthus roseus. 124 75 The biochemical model for indole alkaloid formation in Catharanthus roseus. 126 76 Molecular biology model of Claviceps purpurea alkaloids. 127 77 Three basic hypotheses on the biological nature of alkaloids. 143 78 Rutaecarpine, an alkaloid from Evodia rutaecarpa. 145 79 Effects of foliar application of lupine extracts. 145 80 Mechanism of regulation of alkaloid content in plants. 147 Font Used:Times Margins:Top:18mm Gutter:20mm Font Size:11/13 Text Width:125mm Depth:43 Lines Elsevier AMS Prelims-N52736 Job code: ASLA 17-2-2007 12:35p.m. Page:xiii Trimsize:165×240MM List of Figures xiii 81 Alkaloids in the acetylcholine receptor. 151 82 Fagaronine, an alkaloid from Fagara zanthoxyloides Lam. 153 83 Model of haemoglobin. 154 84 Diagram of estrogenic activity of the alkaloids. 155 85 Activity of some alkaloids on Gram-positive and Gram-negative bacteria. 157 86 Some alkaloids from Strychnos species. 160 87 Acute toxicity of berberine and thebaine 163 88 Acute toxicity of some quinolizidine alkaloids 165 89 Acute toxicity of some pyrrolizidine alkaloids 167 90 Some narcotics and their derivatives. 170 91 Model of evolutionary interaction between alkaloids and insects. 179 92 General diagram of alkaloidal applications in clinical practice. 184 93 Sanguinarine, an alkaloid from Sanguinaria canadiensis. 184 94 Nitrogen content in different soils after 1 year from sample preparations. 196 95 Diagram of the links between areas connected to alkaloidal applications produced by biotechnology. 197 96 Diagram of alkaloid production by cell culture. 199 97 Cell-culture techniques in the organogenesis stage. 199 98 A diagram of the accumulation of pyrrolizidine alkaloids in some insect species during various developmental stages. 211 99 The copulation of butterflies. 213 100 The butterfly’s interaction with alkaloidal plants. 213 101 RF of QAs+ individuals in Coronilla varia, Cytisus scoparius, Lotus corniculatus, Lupinus polyphyllus, Meliotus officinalis, Ononis repens, Ornithopus perpusillus, Oxytropis campestris during 1999–2003. 222 102 RF of QAs+ individuals in Astragalus spp. 222 103 RF of QAs+ individuals in Lathyrus spp. 223 104 RF of QAs+ individuals in Medicago spp. 223 105 RF of QAs+ individuals in Trifolium spp. 224 106 RF of QAs+ individuals in Vicia spp. 224 107 MEC of Astragalus species. 225 108 MEC of Coronilla, Cytisus, Lotus, Lupinus, Meliotus, Ononis, Ornithopus, Oxytropis spp. 226 109 MEC of Lathyrus species. 227 110 MEC of Medicago sativa and Medicago lupulina. 228 111 MEC of Trifolium species. 229 112 MEC of Vicia species. 230 Font Used:Times Margins:Top:18mm Gutter:20mm Font Size:11/13 Text Width:125mm Depth:43 Lines Elsevier AMS Prelims-N52736 Job code: ASLA 17-2-2007 12:35p.m. Page:xv Trimsize:165×240MM List of Tables 1 Main types of alkaloids and their chemical groups 7 2 General botanical characteristics of the Dogbane family 14 3 General botanical characteristics of the Aster family 18 4 General botanical characteristics of the Logan family 20 5 General botanical characteristics of the Poppy family 21 6 General botanical characteristics of the Citrus family 23 7 General botanical characteristics of the Nightshade family 26 8 General botanical characteristics of the Borage family 28 9 General botanical characteristics of the Legume family 30 10 Occurrence of some important alkaloids in the nature 33 11 General botanical characteristics of the Monseed family 45 12 General botanical characteristics of the Berberry family 46 13 General botanical characteristics of the Buttercup family 47 14 General botanical characteristics of the Lily family 48 15 General botanical characteristics of the Coffee family 50 16 General botanical characteristics of the Amaryllis family 52 17 General botanical characteristics of the Oleaster family 53 18 General botanical characteristics of the Caltrop family 54 19 Amino acids and their participation in alkaloid synthesis 62 20 Some well-known enzymes and coenzymes active in alkaloid biogenesis 125 21 General characteristics of the methods and techniques of quinolizidine alkaloid analysis 137 22 Enzymes specifically involved in alkaloid biosynthesis 176 23 The most important alkaloids used in modern medicine 183 24 Potential usage of alkaloid-rich and alkaloid-poor Washington lupine (Lupinus polyphyllus Lindl.) in agriculture 191 25 Some alkaloids produced by cell cultures 200 26 Selective Toxicity Coefficients (STC) of some alkaloids and selective toxicity in the ecosystem 208 27 Systematic division and habitat characteristics of the studied legume species 216 28 Quinolizidine alkaloid frequencies in plant populations of Fabaceae in the boreal zone during 1999–2003 220 29 Frequencies of QAs+ in the legume species studied 221 Font Used:Times Margins:Top:18mm Gutter:20mm Font Size:11/13 Text Width:125mm Depth:43 Lines Elsevier AMS Prelims-N52736 Job code: ASLA 17-2-2007 12:35p.m. Page:xvii Trimsize:165×240MM Preface This book is intended to be a presentation of alkaloids from chemical, biological and ecological points of view. It is a text for chemists, biologists and ecologists alike. However, the intended audience of this work is not limited to scientists, teachers and other present and future specialists.
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    on Adulteration of Hydrastis canadensis root and rhizome By Michael Tims, PhD Maryland University of Integrative Health, 7750 Montpelier Road, Laurel, MD 20723 Correspondence: e-mail Keywords: Hydrastis canadensis, goldenseal root, adulterant, adulteration Goal: The goal of this bulletin is to provide information and/or updates on issues regarding adulteration of goldenseal (Hydrastis canadensis) root to the international herbal industry and extended natural products community in general. It is intended to present the available data on occurrence of adulteration, the market situa- tion, and consequences for the consumer and the industry. 1 General Information 1.1 Common name: Goldenseal1,2 1.2 Other common names: English: Yellow root, yellow puccoon, ground raspberry, wild curcuma*, Indian dye, eye root, eye balm, Indian paint, jaundice root, Warnera3,4 French: Hydraste du Canada, hydraste, fard inolien, framboise de terre, sceau d’or5 German: Goldsiegelwurzel, Kanadische Gelbwurz, Kanadische Orangenwurzel5 Italian: Idraste, radice gialla6 Goldenseal Hydrastis canadensis Spanish: Hidrastis, hidrastis de Canadá, raíz de oro, scello de Photo ©2016 Steven Foster oro5 1.3 Accepted Latin binomial: Hydrastis canadensis7,8 1.4 Botanical family: Ranunculaceae 1.5 Plant part and form: Whole fresh or dry roots and rhizomes, powdered dry roots and rhizomes, hydroalcoholic and glycerin-water extracts and powdered dry extracts.9,10 Dried whole or powdered roots and rhizomes complying with the United States Pharmacopeia (USP) are required to contain
  • The Iboga Alkaloids

    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 ... .....................................
  • (12) United States Patent (10) Patent No.: US 8,980,319 B2 Park Et Al

    (12) United States Patent (10) Patent No.: US 8,980,319 B2 Park Et Al

    US00898O319B2 (12) United States Patent (10) Patent No.: US 8,980,319 B2 Park et al. (45) Date of Patent: *Mar. 17, 2015 (54) METHODS OF PRODUCING STABILIZED A613 L/445 (2006.01) SOLID DOSAGE PHARMACEUTICAL A613 L/47 (2006.01) COMPOSITIONS CONTAINING A6II 45/06 (2006.01) MORPHINANS A63/67 (2006.01) (52) U.S. Cl. (71) Applicant: Mallinckrodt LLC, Hazelwood, MO CPC ............. A6 IK3I/485 (2013.01); A61 K9/1652 (US) (2013.01); A61 K9/2031 (2013.01); A61 K 9/2081 (2013.01); A61 K9/2086 (2013.01); (72) Inventors: Jae Han Park, Olivette, MO (US); A6IK9/2095 (2013.01); A61 K9/5042 Tiffani Eisenhauer, Columbia, IL (US); (2013.01); A61 K3I/4355 (2013.01); A61 K Spainty,S.Isna Gupta, F11llsborough, 31/4375A6 (2013.01); IK3I/445 gets (2013.01); it' A6 (2013.01); IK3I/47 Stephen Overholt, Middlesex, NJ (US) (2013.01); A61K 45/06 (2013.01); A61 K 9/2013 (2013.01); A61 K9/209 (2013.01); (73) Assignee: Mallinckrodt LLC, Hazelwood, MO A6 IK3I/167 (2013.01) (US) USPC ........... 424/472: 424/465; 424/468; 424/490; c - r - 514/282; 514/289 (*) Notice: Subject to any disclaimer, the term of this (58) Field of Classification Search patent is extended or adjusted under 35 N U.S.C. 154(b)b) by 0 daysyS. Seeone application file for complete search history. This patent is Subject to a terminal dis claimer. (56) References Cited (21) Appl. No.: 14/092.375 U.S. PATENT DOCUMENTS (22) Filed: Nov. 27, 2013 2008, 0026052 A1 ck 1/2008 Schoenhard .................