PHARMACOGNOSY 3

Specific Foundation / Core

Understanding by the students of the substances belonging to groups of alkaloids and their derivatives. In order to achieve these objectives, the physical, chemical and biological properties of these substances are presented, as well as their chemical classification, their biosynthesis and medicinal plants containing them. It will also discussed uses of medicinal plants whose main active ingredients belong in these categories of natural products. Moreover, in the laboratory work the students will know and will analyze herbal medicines included in the European Pharmacopoeia 5, using the appropriate analytical methods (microscopic and phytochemical). Skills: Familiarity and in depth knowledge of phytochemical groups of alkaloids and their derivatives, as well as of herbal medicines containing them.

ALKALOIDS AND RELATED COMPOUNDS Natural products derived biosynthetically from amino acids (non-alkaloids) Papain, Ficin, Bromelain, Abrin and Ricin. Lectins, Mushroom Poisoning—Amatoxins. Phallotoxins, Antamanin, Phallolysin. Enzymatic toxins from snake venom. Neurotoxins, Cardiotoxins. Toxins of Viscum album L. ALKALOIDS. Introduction, chemical structures of alkaloids. Biosynthesis. Detection. Extraction. Isolation. Pharmacological activities. Medical uses. Alkaloids derived from lysine and ornithin. Mannich-type reaction and aldol condensation, Schiff Base reaction. Tropane alkaloids. Structures, biosynthesis of tropane nucleus, biosynthesis of the tropic acid, Medicinal plants: Atropa belladonna L., Datura stramonium L., Hyoscyamus niger. Solanaceae: Industrial sources of tropane alkaloids: Plants (Datura sanguinea, D. metel, Hyoscyamus muticus, Duboisia myoporoides, D. leichhardtii) Alkaloids of Erythroxylaceae: Cocaine. Pyrrolizidine alkaloids. Structures. Biosynthesis. Toxicity in animals and human. Plants containing pyrrolizidine alkaloids: Borago officinalis, Symphytum officinale, Tussilago farfara, Eupatorium cannabinum, Senecio vulgaris. Quinolizidine alkaloids. Cytisus scoparius. Sparteine, Laburnus anagyroides, Lupinus spp. Indolizidine alkaloids. (-)–Swainsonine, (+)–Castanospermine. Piperidine alkaloids. Lobelia inflata. Punica granatum. Piperidine Amides and Piperidine Alkaloids not from the Metabolism of Lysine. Piper nigrum L. (piperine), Conium maculatum coniine, N-methylconiine, conhydrine, conhydrinone. Toxicity. Nicotinic acid derivatives. Nicotiana tabacum. Nicotine, anatabine, quinolinic acid. Areca catechu L. Alkaloids derived from phenylalanine and tyrosine. Isoquinoline alkaloids. Simple tetrahydroisoquinolines. Lophophora williamsii (Peyotl). Phenylethylamines. Ephedra spp. Ephedrine, Catha edulis. Benzyltetrahydroisoquinolines alkaloids. Biosynthesis. Papaverine. Benzylisoquinolines. Curare of Menispermaceae and Loganiaceae. Pharmacological properties. Medical uses. Erythrina alkaloids. Aporfinoids. Apomorphine. Boldin and isoboldin from Peunus boldus. Protoberberines and their derivatives. Hydrastis canadensis (berberine), Fumaria officinalis, Chelidonium majius. Biosynthesis of benzophenanthrines (chelidonine, sanguinarine) from stylopine. Sanguinara canadensis. Eschscholtzia californica. Papaver roeas. Morphinanes. Papaver somniferum. Opium. Morphine. Codeine, Noscapine, Papaverine (pharmacological activity). Extraction and isolation of opium alkaloids. Medical uses, Contraindications and side effects. (Codethriline, Pholcodine, Dihydrocodeine, N-allyl-normorphine (nalorphine), N-cyclopropylmethyl-14-hydroxynordihydromorphinone (nalthrexone), N-allyl-14-hydroxynordihydromorphinone (naloxone). Heroine. Phenylethylisoquinolines. Colchicum autumnale (colchicine) Alkaloids of Amaryllidaceae (galanthamine). Isoquinoline-monoterpenic alkaloids. Cephaelis spp. (Ipeca). Alkaloids derived from tryptophan. Simple amines and carbolines. Indolines derived from cyclization of tryptophan. Ergolines. Indole-monoterpenic alkaloids. β-Carbolines – Hallucinogens of C. America, Agaricaceae (psilocin, psilocybin) Myristicaceae of S. America – Mimosaceae of S. America – Malpighiaceae of S. America – Peganum harmala L.. Alkaloids derived from 5-hydroxytryptophan. Physostigma venenosum (Physostigmatis semen or Calabar semen). Ergot alkaloids (Claviceps purpurea). Indole-monoterpenic alkaloids. Biosynthesis – strictosidine. Corynantheanes, Strychnanes, alkaloids of Catharanthus, Cinchona alkaloids (Loganiaceae, Rubiaceae, Apocynaceae). Alkaloids derived from anthranilic acid (quinolines, acridines, quinazolines) Alkaloids derived from histidine – Imidazoles. Alkaloids derived from terpene metabolism. Mono- and sesquiterpene alkaloids. Diterpene alkaloids, Aconitum spp., Ranunculaceae alkaloids. Steroidal alkaloids - Apocynaceae, Liliaceae, Solanaceae. Alkaloids of different chemical structures (spermine, spermidine, macrocyclic peptides, maytansinoids). Purines (caffeine, theophylline, theobromine). LABORATORY WORK: Microscopic and Phytochemical control of herbal drugs containing alkaloids. Microscopic control: Folia Hyoscyami, Folia Belladonnae, Folia Stramonii, Radix Ipecacuanhae, Rhizoma Hydrastis, Semen Colae, Cortex Cinchonae, Semen Colchici, Herba Chelidonii, Herba Lobelia, Folia Jaborantii, Folia Boldi Phytochemical control: Hyoscyamus niger: qualitative and quantitative control, Isolation of caffeine from leaves of Camelia sinensis, Radix Ipecacuanha: qualitative and quantitative determination of emetine and cephaeline, qualitative and quantitative determination of quinine and quinidine.

12-08-2013