OVERVIEW

The main classes of secondary metabolites present in herbal drugs of pharmaceutical interest are described in a systematic way with notes on the main routes of metabolism in the higher plants.

LEARNING OUTCOMES

Aim of the course is to provide the basic information for the knowledge of the major chemical classes of plant secondary metabolites of pharmaceutical interest and their biosynthesis in relation to the  different herbal drugs from which they can be obtained.

AIMS AND LEARNING OUTCOMES

Aim of the course is to provide the basic information for the knowledge of the major chemical classes of plant secondary metabolites of pharmaceutical interest and their biosynthesis in relation to the various herbal drugs from which they can be obtained.

PREREQUISITES

The student must possess the basic knowledge of animal biology, organic chemistry and pharmacognosy.

Teaching methods

The course consists of lectures, which explains the different subjects on the basis of illustrated educational materials (slides) that is provided to the students at the beginning of the course, through aulaweb. Students are invited to download the material from the beginning of the course, in order have a track on which to insert notes, comments etc. Learning tests are foreseen.

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SYLLABUS/CONTENT

CBV1a_Introduction -hystorical outline – current uses of herbal drugs – advantages of the use of the pure active compound - plant compounds as a starting point for hemisynthesis - plant compounds used as molecular models - plant compounds used as pharmacological probes – plant compounds for new drugs - the research of bioactive compounds: the rationale. CBV1b_plant secondary metabolites: definition and functions-hormesis and xenohormesis- PAINS. CBV1c_The building blocks and construction mechanisms of secondary metabolites - the chemical classes of bioactive compounds – the main biosynthetic reactions. CBV1d_ the “omic” sciences: metabolomics, fluxomic. CBV1e_Plant sources of the bioactive compounds used in therapy: breeding, harvest, drying, stabilization, quality control. Legislative outline about the cultivation, harvesting and first processing of medicinal plants. Economic observatory of the medicinal plant sector. The sector plan. CBV1f_Traditional medicines, ecopharmacognosy, biopiracy, the sites of the biosynthesis of the secondary metabolites. Extraction and structural characterization of bioactive plant compounds. CBVg_Plant biotechnologies.

CBV2_Carbohydrates: monosaccharides, oligosaccharides, polysaccharides, aminosugars, aminoglycosides.

CBV3_The acetate patway. Fatty acids - prostaglandins, phytoprostanes - acetylenic fatty acids.

CBV4a_. Amino acids - Cyanogenic glycosides and glucosinolates. CBV4b_Seaweed iodine amino acids – Peptides, peptide antibiotics, fungal peptide toxins – Proteolytic enzymes- Lectins.

CBV5a_ Introduction to the Alkaloids – Overview of the main steps in alkaloid biosynthesis - Alkaloids Derived from Ornithine: pyrrolidine and tropane alkaloids, CBV5b_pyrrolizidine alkaloids - Alkaloids derived from lysine: piperidine alkaloids, quinolizidine alkaloids, indolizidine alkaloids. CBV5c_Alkaloids derived from nicotinic acid: pyridine alkaloids - Alkaloids derived from tyrosine: phenylethylamines and simple tetrahydroisoquinoline alkaloids, betalains. CBV5d_benzyltetrahydroisoquinoline alkaloids, curare. CBV5e_modified benzyltetrahydroisoquinoline alkaloids, CBV5f_phenethylisoquinoline alkaloids, terpenoid tetrahydroisoquinoline alkaloids, Amaryllidaceae alkaloids - Alkaloids derived from tryptophan: simple indole alkaloids, simple β-carboline alkaloids, terpenoid indole alkaloids, CBV5g_quinoline alkaloids, pyrroloindole alkaloids, CBV5h_Ergot alkaloids - Alkaloids derived from anthranilic acid: quinazoline alkaloids, quinoline and acridine alkaloid - Alkaloids derived from histidine: imidazole alkaloids - Alkaloids derived by amination reactions: acetate-derived alkaloids, phenylalanine-derived alkaloids, terpenoid alkaloids.

CBV6_Purine compounds – Benzoxazinones

CBV7a_Benzoic acids and Simple phenols – Phenilpropenes – Styrylpyrones – Lignans. CBV7b_Coumarins – Aflatoxins – Chromones – Flavonoids – Tannins. CBV7c_Phloroglucinols – Naphthoquinones and other aromatic polyketides – Anthraquinones – Tetracyclines - Macrolides and Polyethers – Statins.

CBV8a_Introduction to isoprenoids – The mevalonate and deoxyxylulose phosphate pathways _ classes of isoprenoids: Monoterpenes, Sesquiterpenes, Diterpenes, Sesterterpenes, Tritepenes, Higher terpenoids. CBV8b_Essential oils, Rosin and Oleoresins – Iridoids. CBV8c_Triterpenoids, Saponins and Steroids. CBV8d_Tetraterpenes – Mixed Isoprenoids.

RECOMMENDED READING/BIBLIOGRAPHY

Berger S., Sicker D. 2009. Classics in Spectroscopy. Isolation and Structure Elucidation of Natural Products. Weinheim (Germany): Wiley-Vch.

Dewick P.M. 2013. Chimica, Biosintesi, e Bioattività delle Sostanze Naturali. Padova: Piccin.

Samuelsson G. 2003. Farmacognosia. Farmaci di origine naturale. Roma: EMSI.

Exam Board

ANGELA BISIO (President)

PAOLO GIORDANI (President)

MARCO MILANESE

Teaching methods

The course consists of lectures, which explains the different subjects on the basis of illustrated educational materials (slides) that is provided to the students at the beginning of the course, through aulaweb. Students are invited to download the material from the beginning of the course, in order have a track on which to insert notes, comments etc. Learning tests are foreseen.

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Exam description

The examination starts with a written test consisting of six open-ended questions, 5 points each, covering all the issues described in the file found on Aulaweb: "Topics covered in the course of BIOACTIVE CONSTITUENTS OF PLANT DRUGS".

Available time: one hour.

The score of each response will be calculated using the following methods: 1) Learning: 3 points; 2) communication skills: 1.5 points; 3) judgment: 1.5 points.

The list of questions is listed in the file found on Aulaweb: "Examination Questions of BIOACTIVE CONSTITUENTS OF PLANT DRUGS".

The result obtained in the written test is then discussed with the student and the examination may continue orally.

The examination is passed only if a score ≥18 was achieved.

The obtained score will be averaged with the one obtained in Plant Biology to give the final vote of the two integrated courses. The two tests must be done on the same day, and both have to be overcome with a ≥18 score.

The possibility of subsequent examination dates is given only in very exceptional cases and this possibility will be discussed with the commission in the exam calendar official date anyway.

Assessment methods

The exam questions are conceived so that the student can provide schematic answers, not more than 10-15 lines, that indicate the plant source, the chemical classes of its main constituents, their biosynthesis and the structural formulas of the main compounds.

The list of exam questions on Aulaweb allows the student to have both a personal assessment and a complete final preparation for the written test.