PHARMACOGNOSY 2

Specific Foundation / Core

Understanding by the students of the substances belonging to groups of terpenoids and steroids 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 terpenoids and steroids and their derivatives, as well as of herbal medicines containing them.

TERPENOIDS AND STEROIDS AND THEIR DERIVATIVES Introduction. Origin of C5 units. Mevalonic acid pathway and GAP/pyruvate pathway for IPP formation. • Monoterpens: Introduction, chemical structures of monoterpenes. Biosynthesis. • Sesquiterpenes: General structures of sesquiterpenes • Essential oils: Definition, distribution in plants and their functionality. Physical properties. Chemical constitution. Terpenoids and sesquiterpenoids of essential oils. Factors that influenced the diversity of essential oils (chemotypes, influence of the vegetation cycle, environmental factors, etc.). Techniques and methods used to produce essential oils. Quality control of essential oils. Pharmacological properties. Toxicity. Uses. Storage and preservation of essential oils and aromatic plants. Lesions. • Aromatic and medicinal plants.  Apiaceae: Pimpinella anisum L., Foeniculum spp., Anethum graveolens, Carum carvi L., Coriandrum sativum L., Apium graveolens L., Petroselinum crispum (Mill.) A.W.Hill  Asteraceae: Chamomilla recutica (L.), Artemissia vulgaris L., A. absinthum L. and A. dracunculus L.  Lamiaceae: Ocinum basilicum L., Lavandula spp., Origanum majorana L., Melissa officinalis L., Mentha x piperita L., Origanum vulgare L., Rosmarinus officinalis, Satureja montana L., Salvia spp., Thymus vulgaris L. and T. serpyllum L.  Lauraceae: Cinnamomum verum J.Presl (Κεϋλάνης), C. aromaticum Nees (China), C. camphora L., Laurus nobilis L.  Myrtaceae: Syzygium aromaticum, Eucalyptus globulus  Rutaceae: Citrus aurantium L., Aurantium spp., etc. essential oils of Citrus spp. • Oleoresins and related products from Pinus spp.: Turpentine, Juniperus spp. • Iridoids and Seco-iridoids: General structures, Biosynthesis, Extraction Isolation and Identification, Biological and Pharmacological properties. Medicinal plants containing iridoids: Valeriana officinalis, Harpagophytum procumbens, Olea europaea L., Gentiana lutea, Centaurium erythreae, Menyanthes trifoliate, Lamium album L. • Pyrethrines: Structures, Biological properties. Medical uses. Chrysanthemum cinerariafolium. • Cannabinoids: Chemical structures, biosynthesis, quality control of cannabinoids. Cannabis herb. • Sesquiterpenoids. Cnicus benedictus (cnicin), Αrtemisia absinthun L. (artabsin, chamazulene), Matricaria recutica, Chamaemelum nobilis (German Chamomile), Picrotoxin, Picrotin, Artemissia annua, Cantharidine. • Sesquiterpene lactones: chemical structures, biological properties, medical uses. Artemisia annua L. (artemisinin), Arnica montana L., Inula helenicum. Tanacetum parthenium, Sesquiterpene lactones and allergy. • Diterpenes: chemical structures, biosynthesis, medical uses. Taxus spp., Teucrium spp., Stevia rebaudiana. Poisonous plants containing diterpenes (phorbol and ingenol esters): Daphne spp. and Euphorbia spp. Toxicity. Rhpdodendron spp., Ericaceae spp. (Kalmia, Pieris). • Triterpenes and steroids. General chemical structures. Biosynthesis. • Steroid and triterpenoid saponins. Extraction, chromatographic separation, quantitative determination, biological and pharmacological properties. Semi-synthetic production of steroidal hormones. Dioscorea spp., Agave siaalana, Solanum spp. Sterols. • Glycyrrhiza glabra., Aesculus hippocastanum, Ruscus aculeatus, Polygala senega, Hedera helix, Primula veris, Centella asiatica, Calendula officinalis. • Adaptogenic plants: Panax ginseng, Eleutherococcus senticosus • Plants containing saponosides: Quillaia saponaria, Saponaria officinalis, Gypsophila spp. • Cordial glycosides. Chemical structures, biosynthesis, physicochemical properties, quality and quantity control, pharmacological properties, therapeutic indications. • Plants containing cordial glycosides: Digitalis spp., D. purpurea and D. lanata (digoxin, digitoxin, deacetyl-lanatosid C), Urginea matitima, Strophanthus spp, Convallaria majalis, Adonis vernalis, Heleborus niger, Nerium oleander. • Poison Toad, Bufotoxin. • Vitamin D. Biosynthesis, production, properties. Cod Liver Oil. • Vitex agnus-castus L., Urtica dioica L. • Cucurbitacins, boswellic acids, limonoids, quassinoids. • Tetraterpenes (C40), carotenoids. Biosynthesis, properties, uses. • Chemistry of Vitamin A. • Plants containing carotenoids: Capsicum spp., Crocus sativus L. LABORATORY WORK: Microscopic and Phytochemical control of herbal drugs containing terpenes and/or terpene derivatives of the European Pharmacopoeia 5. Microscopic control: Folia Menthae, Folia Melissae, Folia Lavandulae, Folia Salviae, Folia Digitalis, Radix Liquiritiae, Herba Absinthii, Flores Chamomillae, Radix Valerianae, Herba Cannabis, Radix Gentianae, Folia Eucalypti Phytochemical control: Digitalis purpurea: chromatographic control – qualitative and quantitative determination of cordial glycosides. Radix Liquiritiae: chromatographic quality control.

12-08-2013