Pharmacognosy 2 - Theory

Data

Official data in SubjectManager for the following academic year: 2024-2025

Topic

Pharmacognosy covers general aspects of medicinal plants (such as industrial applications, research, cultivation and cultivars, gene technology, critical evaluation of holistic medicine and homeopathy, possibilities of phytotherapy) and discusses the chemical composition and other qualitative characteristics, as well as the most important areas of usage and pharmacology of herbal drugs and drug fractions such as oils and essential oils. Based on their previous pharmacobotanic knowledge students become acquainted with medicinal plants and drugs that are used in pharmacotherapy (especially in phytotherapy) both in Hungary and abroad. Students are required to recognize the most important tea drugs and drugs with strong physiological effect that are traded and/or imported in Hungary. In the frame of practices students obtain experience in drug analysis and identification methods and the ability to solve daily arising problems, with special emphasis on gathering information from literature, databases and the internet.

Course objective and role in the curriculum: students should become familiar with the general, phytochemical and pharmacological features of drugs applied in pharmaco- and phythotherapy.

Lectures

• 1. General characterization of alkaloids and their main groups. Purin-containing drugs - Horváth Györgyi
• 2. General characterization of alkaloids and their main groups. Purin-containing drugs - Horváth Györgyi
• 3. Drugs containing ornithine, lysine and phenylalanine-derived alkaloids - Horváth Györgyi
• 4. Drugs containing ornithine, lysine and phenylalanine-derived alkaloids - Horváth Györgyi
• 5. Drugs containing tryptophan and histidine alkaloids - Horváth Györgyi
• 6. Drugs containing tryptophan and histidine alkaloids - Horváth Györgyi
• 7. General characterization of phenoloids and their main groups - Horváth Györgyi
• 8. General characterization of phenoloids and their main groups - Horváth Györgyi
• 9. Drugs containing flavonoids - Horváth Györgyi
• 10. Drugs containing flavonoids - Horváth Györgyi
• 11. Drugs containing coumarins. Drugs containing phenylpropanoids and terpenophenols - Horváth Györgyi
• 12. Drugs containing coumarins. Drugs containing phenylpropanoids and terpenophenols - Horváth Györgyi
• 13. Drugs containing anthranoids and naphthoquinone derivatives - Horváth Györgyi
• 14. Drugs containing anthranoids and naphthoquinone derivatives - Horváth Györgyi
• 15. Midterm written exam - Horváth Györgyi
• 16. Midterm written exam - Horváth Györgyi
• 17. Drugs containing polyphenols - Horváth Györgyi
• 18. Drugs containing polyphenols - Horváth Györgyi
• 19. Poisonous plants - Farkas Ágnes
• 20. Poisonous plants - Farkas Ágnes
• 21. Phytochemical and biological screening of herbs (medicinal plants) - Horváth Györgyi
• 22. Phytochemical and biological screening of herbs (medicinal plants) - Horváth Györgyi
• 23. Medicinal plant research in the XXI. century: Plant-origin antiviral compounds - Horváth Györgyi
• 24. Medicinal plant research in the XXI. century: Plant-origin antiviral compounds - Horváth Györgyi
• 25. Medicinal plant research in the XXI. century: Phytoestrogens - Horváth Györgyi
• 26. Medicinal plant research in the XXI. century: Phytoestrogens - Horváth Györgyi
• 27. Medicinal plant research in the XXI. century: Plant-origin antidiabetic compounds - Horváth Györgyi
• 28. Medicinal plant research in the XXI. century: Plant-origin antidiabetic compounds - Horváth Györgyi

Practices

Seminars

Reading material

Obligatory literature

Literature developed by the Department

1. Györgyi Horváth: Drug reactions in Pharmacognosy, teaching supplement for the pharmacognosy practices, University of Pécs, Department of Pharmacognosy, Pécs, 2011.

2. Györgyi Horváth, Péter Molnár, Tímea Bencsik: Pharmacognosy 2, digital learning material, 2014.

Course materials will be available on Neptun.

Notes

Recommended literature

1. Evans W.C.: Trease and Evans Pharmacognosy, Saunders, London-New York, 2000

2. Aronson J.K. (ed.): Meyler?s Side Effects of Herbal Medicines, Elsevier, Amsterdam-Oxford-Tokyo, 2009

3. Barnes J., Anderson L.A., Phillipson J.D.: Herbal Medicines, 2nd edition, Pharmaceutical Press, London-Chicago, 2002

4. ESCOP Monographs, The Scientific Foundation for Herbal Medicinal Products, 2nd edition, Thieme, United Kingdom-Stuttgart-USA, 2003

5. Poole C.F., Poole S.K.: Chromatography Today, Elsevier, Amsterdam-Oxford-New York-Tokyo, 1991

Conditions for acceptance of the semester

One written exam (min. 60%) based on lectures is compulsory. In the case of failed result, there is one possibility to rewrite it. There is no possibility to take oral exam if somebody receives failed practice result. Oral exam: 2 topics. Before oral exam, there is a drug identification entrance exam. If somebody failed the entrance exam, student cannot continue the oral exam. Result of oral exam includes: entrance exam, oral communication, lecture written exam, practice result.

If somebody writes the 4 drug reports with min. fullfill 90% (4 x 90%)during the semester, will receive rid of the drug entrance exam in Pharmacognosy 2. oral exam.

Mid-term exams

One written exam (min. 60%) based on lectures is compulsory. In the case of failed result, there is one possibility to rewrite it. There is no possibility to take oral exam if somebody receives failed practice result. Oral exam: 2 topics. Before oral exam, there is a drug identification entrance exam. If somebody failed the entrance exam, student cannot continue the oral exam. Result of oral exam includes: entrance exam, oral communication, lecture written exam, practice result.

If somebody writes the 4 drug reports with min. fullfill 90% (4 x 90%)during the semester, will receive rid of the drug entrance exam in Pharmacognosy 2. oral exam.

Making up for missed classes

There is possibility to make up for the missed lectures.

Exam topics/questions

The criterion of admission to the exam is the successful completion of the practice carried out in paralell (midsemester grade with the result different from ?failed?).

Exam questions:

I. General part. Phytochemistry.

1. Carbohydrate synthesis during photosynthesis: the Calvin-cycle; structure and role of phosphoenolpyruvate (PEP) and malic acid; C4 and CAM type plants. Synthesis, role and usage of di- and polysaccharides [sucrose, maltose, starch (amylose, amylopectin), cellulose]. Pectins, mannans, gummi arabicum, heteropolysaccharides: occurrence, medicinal usage.

2. Biological functions and classes of lipids. Building blocks of phosphoglycerides: L-?-phosphatidic acid, cholamine, choline, serine, inositol. Structure of cephalin, lecithine, phosphatidyl serine and phosphatidyl inositol. General characterisation of sphingosine, sphingo- and glycolipids. Physical and chemical characteristics of fats and oils. Biosynthesis of fatty acids. Structure of important saturated and unsaturated fatty acids occurring in plants.

3. Arachidonic acid, prostaglandins: discovery, occurrence, chemical structure, biological effects, medical usage. Structure of ricinoleic acid, ricinine and ricin; occurrence, biological and medicinal importance. Oils of animal origin: chemical structure of the most important compounds in cod-liver oil, medicinal usage. Structure and utilisation of waxes. Polyacetylenes: synthesis, features, occurrence in plants, biological role.

4. Isoprenoid compounds. Isoprene rule; modes of linking of isoprene units; occurrence, biological role, medicinal application; natural and artificial polyisoprenes. General features of terpenes; occurrence; precursors of biosynthesis [mevalonic acid (MVA), isopentenyl pyrophosphate (IPP)]; main steps of biosynthesis. Classification of terpenes. Chemical structure of linear and cyclic monoterpenes with a few examples; occurrence, biological role, medicinal usage.

5. Iridoids, pyrethroids, sesquiterpenes: chemical structure; occurrence in plants, biological role, application in medicine. Diterpenes, triterpenes. Chemical structure, occurrence and biological significance of phytol and squalene. Occurrence, biological role and medicinal usage of triterpenoid saponins.

6. Proteinogenic amino acids: structural formula and chemical name of alanine, arginine, aspartic acid, asparagine, cysteine, glycine, glutamic acid, glutamine, histidine, leucine, isoleucine, lysine, methionine, phenylalanine, proline, hydroxyproline, serine, threonine, tryptophan, tyrosine, valine.

7. Important amino acid reactions a.) Basic reaction of transamination; b.) reductive desamination → formation of ?-amino acids from ?-keto acids (?-oxo acids); c.) formation of glutamine from glutamic acid; d.) decarboxylation; e.) oxidative desamination; f.) formation of asparagine from aspartic acid. Breakdown of xanthine, caffeine and other purine-derived effective substances: formation of ureids, glycolic acid, glyoxylic acid and carbamide. Allantoin, as the most well-known plant ureid.

8. Specific amino acids: chemical structure of ?-amino-butyric acid (GABA), ?-amino-butyric acid (BABA) and ?-alanine; formation, significance in plants; chemical transformation. Occurrence and significance of canavanine. Structure, occurrence and biological effect of L-dihydroxy-phenylalanine (L-DOPA). Occurrence of alkyl- and allyl-derivatives of cysteine; chemical structure and occurrence of diallyl-sulfide and diallyl-disulfide. Occurrence of propenyl-cysteine.

9. Peptids, proteins. Classification of proteins based on solubility relations. Biological and biochemical role of enzymes, classification according to their functions. Occurrence and medicinal usage of some enzymes (papain, bromealin, ficin). The place and main steps of plant protein biosynthesis. Occurrence and biological role of stored proteins. Features, occurrence, biological role and application of lectins (phytohemagglutinins), toxic (ricin) and other plant proteins.

10. Alkaloids I. Definition and general characteristics of alkaloids; natural occurrence. Structure of the most important amino acids in their biosynthesis (ornithine, lysine, phenylalanine, tyrosine, tryptophan, histidine). Structure of N-containing heterocyclic compounds, characteristic for alkaloids (pyrrole, pyrrolidine, pyridine, piperidine, indole, quinoline, isoquinoline, pyrimidine, imidazole, purine, sterane structure). Phenylethylamine-type alkaloids: ephedrine as a protoalkaloid. Mescaline as a protoalkaloid. Occurrence, biological features, application.

11. Alkaloids II. Alkaloids containing pyridine, pyrrolidine, piperidine cycle: chemical formula and name, biological effect of nicotine and coniine. Occurrence of other alkaloids with pyperidine cycle (piperine, lobeline). Tropane alkaloids ? Alkaloids with a condensed pyrrolidine- and piperidine cycle. Structure of nortropane, tropane, tropine (3?-hydroxi-tropane) and tropic acid. Atropine, hyosciamine, scopolamine ? structure, occurrence, biological effect, application in medicine and elsewhere.

12. Alkaloids III. Structure of pseudotropine (3 ?-hydroxi-tropane), ecgonine and cocaine; occurrence and biological effects of cocaine. Structural comparison of novocaine (non-alkaloid) and cocaine, focusing on the atom group responsible for biological effect. Alkaloids with quinoline structure. Structure, occurrence, biological effects and application of quinine.

13. Alkaloids IV. Opium alkaloids: Structure, biological effect and usage of papaverine as an isoquinoline structure alkaloid. Structure of morphine; biological effect, medical usage. Structure, biological effects and medical application of some important morphine derivatives [codeine, tebaine, ethylmorphine (dionine), heroin]. LSD as the most important representative of ergot alkaloids: chemical structure, biological effects. Biological effects and medical application of further important ergot alkaloids.

14. Alkaloids V. Purine alkaloids: tautomeric lactam-lactim equilibrium of xanthine; structure of theophylline, theobromine and caffeine; occurrence, biological effects, usage. Sterane alkaloids (pseudoalkaloids): chemical structure of tomatidine and solanidin; occurrence in plants; usage. Occurrence of protoalkaloids with a special structure (colchicine, aristolochic acid) and colouring agents containing quaternary nitrogen. The most important alkaloid-containing plant families.

15. Phenoloids I. Structure of amino acids in their biogenesis (phenylalanine, tyrosine). Structure of ?-phenyl-propionic acid, trans (E)-cinnamic acid, cis (Z)-cinnamic acid (allo-cinnamic acid), para-coumaric acid, caffeic acid and chlorogenic acid (the ester of caffeic acid and quinic acid). The hydroquinone ? para-benzoquinone transformation. Quinone derivatives and their significance in plant biochemistry. Phenol-carboxylic acids of benzoic acid origin (protocatechuic acid, vanillic acid, gallic acid): structure, occurrence in plants, significance in biology and medicine.

16. Phenoloids II. Structure and occurrence of salicin in plants. Chemical structure of salicylic alcohol, salicylic acid, acetylsalicylic acid (Aspirin) and its Ca-salt (Kalmopyrin); their significance in pharmacy. Structure of anise alcohol and anise aldehyde; occurrence in plants. Structure of some unsaturated phenol alcohols. Trans (E)-cinnamic alcohol and its derivatives: para-coumaryl alcohol, coniferyl alcohol, sinapyl alcohol. Features of lignins, lignans, flavonolignans: occurrence, biological and medicinal importance.

17. Phenoloids III. Coumarins. Chemical structure of coumarin, coumaric acid, aesculin, dicoumarol and furanocoumarins; occurrence in plants; biological and medicinal significance. Flavonoids: Structure of ?- and ?-pyran, ?- and ?-pyrone and coumarin (?-pyrone condensed with benzol). Structure of chromane, chromene, chromone, flavan, flavene, flavon, flavonol (3-hydroxi-flavon) and quercetin. Structure, occurrence and isolation of rutin (vitamin P).

18. Phenoloids IV. Anthocyanins, anthocyanidins, flavylium salts. Structure of flavylium chloride; some derivatives substituted with OH-groups. The pH dependence of the colour of flavylium salts; explanation of their behaviour as indicators. Occurrence in plants, biological effects and medical significance of anthocyanin colouring agents. Tannins. Classification of tannins. Structure of gallic acid, pyrogallol, meta-digallic acid, penta-meta-digalloyl-?-D-glucose. Occurrence, features and application of tannins.

19. Phenoloids V. Quinones and terpenophenols. Structure of juglone, anthraquinone (9,10-anthraquinone) and anthrone. Biological effect, features and usage of juglone. Occurrence and medicinal significance of plant effective substances with anthraquinone and anthrone (naphtho-dianthrone) structure. Terpenophenols (cannabinoids). Occurrence and biological effect of THC; effective substances of hop and their structure.

II. Drugs

1. Drugs containing carbohydrates: Mel depuratum, Manna, Pulpa tamarindorum, Rosae pseudo-fructus, Solani amylum, Tritici amylum, Maydis amylum, Oryzae amylum, Lana gossypii, Agar, Acaciae gummi (Gummi arabicum), Tragacantha, Helianthus tuberosus

2. Drugs containing mucilage-like carbohydrates: Lichen islandicus, Althaeae radix, Althaeae folium, Malvae sylvestris folium et flos, Salep tuber, Graminis rhizoma, Cyamopsidis tetragonolobae semen, Farfarae folium et flos, Lini semen, Cydoniae semen

3. Carbohydrate-containing drugs stimulating non-specific immune reactions: Echinaceae radix, Eupatorii herba, Arnicae flos, Visci stipes, Calendulae flos, Tiliae flos, Foenugraeci semen

4. Drugs containing polar, non-polar fats, oils and waxes of plant origin: Lecitin, Ricini oleum virginale, Helianthi annui oleum raffinatum, Lini oleum virginale, Soiae oleum raffinatum, Carthami oleum raffinatum, Brassicae napae oleum, Arachidis oleum raffinatum, Butyrum cacao, Jojoba, Cera carnauba

5. Drugs containing essential oil: Menthae piperitae folium, Lavandulae flos, Basilici herba, Orthosiphonis folium, Melissae folium, Thymi herba, Serpylli herba, Origani herba, Majoranae herba, Saturejae herba, Hyssopi herba, Salviae officinalis folium, Rosmarini folium, Rosae petalum, Juniperi pseudo-fructus, Camphor, Eucalypti folium, Carvi fructus, Coriandri fructus, Aurantii amari epicarpium et mesocarpium, Cardamomi fructus, Myrrha

6. Essential oils: Anisi aetheroleum, Aurantii amari floris aetheroleum, Aurantii dulcis aetheroleum, Carvi aetheroleum, Caryophylli floris aetheroleum, Cinnamomi zeylanici corticis aetheroleum, Citronellae aetheroleum, Coriandri aetheroleum, Eucalypti aetheroleum, Foeniculi amari fructus aetheroleum, Juniperi aetheroleum, Lavandulae aetheroleum, Limonis aetheroleum, Matricariae aetheroleum, Melaleucae aetheroleum, Menthae piperitae aetheroleum, Myristicae fragrantis aetheroleum, Pini silvestris aetheroleum, Rosmarini aetheroleum, Salviae sclareae aetheroleum, Thymi aetheroleum

7. Drugs containing iridoids: Plantaginis lanceolatae folium, Euphrasiae herba, Lamii albi herba, Harpagophyti radix, Agni casti fructus, Verbenae herba, Valerianae radix, Gentianae radix, Menyanthidis trifoliatae folium, Centaurii herba, Oleae folium

8. Drugs containing sesquiterpenes: Chamomillae romanae flos, Millefolii herba, Matricariae flos, Tanaceti parthenii herba, Cynarae folium, Absinthii herba, Cardui benedicti herba, Inulae radix, Arnicae flos, Bardanae radix, Cichorii radix et herba, Taraxaci radix et herba, Pyrethri flos

9. Drugs containing diterpenes and triterpenes: Colophonium, Marrubii herba, Ballotae nigrae herba, Taxi baccatae folium, Liquiritiae radix, Quillajae cortex, Verbasci flos, Saponariae albae radix, Primulae radix, Polygalae radix, Pruni africanae cortex, Hederae helicis folium, Betulae folium, Veronicae herba, Ononidis radix, Solidaginis virgaureae herba, Solidagnis herba, Centellae asiaticae herba, Hippocastani semen, Calendulae flos, Avenae herba, Cimicifugae rhizoma

10. Drugs containing adaptogenic triterpenes, sterols and saponins: Ginseng radix, Eleuterococci radix, Urticae radix et folium, Epilobii herba, Cucurbitae semen, Dioscoreae tuber, Trigonellae foenigraeci semen, Rusci rhizoma, Sabalis serratulae fructus

11. Drugs containing bufadienolides, cardenolides: Digitalis purpureae folium, Digitalis lanatae folium, Strophanthi semen, Scillae bulbus, Adonidis herba, Convallariae herba, Nerii folium, Hellebori radix, Leonuri cardiacae herba

12. Drugs containing specific amino acids, amino acid derivatives and amines: Allii sativi bulbus, Allii ursini folium, Allii cepae bulbus, Bursae pastoris herba, Galegae herba, Phaseoli legumen

13. Drugs containing alkaloids of ornithine and lysine origin: Belladonnae radix et folium, Hyoscyami folium, Stramonii folium, Cocae folium, Nicotianae folium, Pulmonariae herba, Symphyti radix, Lobeliae herba, Laburni semen, Sarothamni scoparii herba

14. Drugs containing alkaloids of phenylalanine origin: Capsici fructus, Ephedrae herba, Papaveris fructus sine seminibus, Opium crudum, Chelidonii herba et radix, Fumariae herba, Berberidis radicis cortex, Colchici tuber, Ipecacuanhae radix, Boldi folium, Tubokurarin-curare

15. Drugs containing alkaloids of tryptophan origin: Secale cornutum, Rauwolfiae radix, Vincae minoris herba, Catharanthi herba, Strychni semen, Curare, Cinchonae cortex, Uncariae tomentosae radix, Passiflorae herba, Physostigmae semen

16. Drugs containing purine structure effective substances: Coffeae semen, Theae folium, Cacao semen, Guarana, Mate folium, Colae semen

17. Drugs containing terpenoid alkaloids: Aconiti tuber, Veratri rhizoma et radix, Solani herba

18. Drugs containing cyanogenic glycosides, isothiocyanate derivatives: Amygdalae amarae semen, Lini semen, Sinapis nigrae semen

19. Drugs containing phloroglucin and terpenophenol derivatives: Filicis maris rhizoma, Lupuli flos, Cannabis herba

20. Drugs containing phenol- and phenylpropionic acid derivatives: Cinnamomi cortex, Caryophylli flos, Zingiberis rhizoma, Anisi fructus, Anisi stellati fructus, Foeniculi dulcis fructus, Calami rhizoma, Petroselini fructus, Balsamum peruvianum, Filipendulae ulmariae herba, Salicis cortex, Curcumae xanthorrhizae rhizoma

21. Drugs containing quinone- and anthraquinone derivatives, naphthoquinone- and dianthrone derivatives: Uvae ursi folium, Vitis-idaeae folium, Frangulae cortex, Rhamni purshianae cortex, Rhei radix, Aloe, Juglandis folium, Alkannae radix, Droserae herba, Lawsoniae folium, Sennae folium et fructus, Hyperici herba

22. Drugs containing coumarins, furocoumarins, lignans and flavanolignans: Meliloti herba, Angelicae radix, Ammeos visnagae fructus, Ammi majoris fructus, Levistici radix, Apii fructus, Podophylli rhizoma, Silybi mariani fructus

23. Drugs containing flavonoids: Tiliae flos, Sambuci flos, Equiseti herba, Crataegi folium cum flore, Crataegi fructus, Violae herba cum floris, Ginkgo folium, Stoechados flos, Populi gemma, Propolis, Ribis nigri folium

24. Drugs containing tannins, polyphenols: Galla, Quercus cortex, Ratanhiae radix, Hamamelidis folium, Tormentillae rhizoma, Anserinae herba, Gei radix et rhizoma, Agrimoniae herba, Fragariae folium, Alchemillae herba, Polygoni avicularis herba, Rubi idaei folium, Rubi fruticosi folium, Coryli folium, Myrtilli folium et fructus, Lythri herba

Examiners

• Csikós Eszter
• Farkas Ágnes
• Horváth Györgyi

Instructor / tutor of practices and seminars