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.

AIMS AND CONTENT

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.

TEACHING METHODS

The course consists of lectures, which explains the different subjects on the basis of illustrated educational materials (slides) that is entirely 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. 

SYLLABUS/CONTENT

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 pharmacological probes - plant compounds used as molecular models -plant secondary metabolites: definition and functions-hormesis and xenohormesis- PAINS - The building blocks and construction mechanisms of secondary metabolites – the chemical classes of bioactive compounds – the main biosynthetic reactions - Plant sources of the bioactive compounds used in therapy: breeding, harvest, drying, stabilization, quality control - the omic sciences.

Plant biotechnologies.

Extraction and structural characterization of bioactive plant compounds.

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

Fatty acids - prostaglandins, phytoprostanes - acetylenic fatty acids.

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

Alkaloids introduction – Overview of the main steps in alkaloid biosynthesis - Alkaloids Derived from Ornithine: pyrrolidine and tropane alkaloids, pyrrolizidine alkaloids - Alkaloids derived from lysine: piperidine alkaloids, quinolizidine alkaloids, indolizidine alkaloids - Alkaloids derived from nicotinic acid: pyridine alkaloids - Alkaloids derived from tyrosine: phenylethylamines and simple tetrahydroisoquinoline alkaloids, tetrahydroisoquinoline alkaloids, modified benzyltetrahydroisoquinoline alkaloids, phenethylisoquinoline alkaloids, terpenoid tetrahydroisoquinoline alkaloids, Amaryllidaceae alkaloids - Alkaloids derived from tryptophan: simple indole alkaloids, simple β-carboline alkaloids, terpenoid indole alkaloids, quinoline alkaloids, pyrroloindole alkaloids, 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.

Purine compounds – Benzoxazinones

Benzoic acids and Simple phenols – Phenilpropenes – Styrylpyrones – Lignans - Coumarins – Aflatoxins – Chromones – Flavonoids – Tannins - Phloroglucinols – Naphthoquinones and other aromatic polyketides – Anthraquinones – Tetracyclines - Macrolides and Polyethers – Statins.

Introduction to isoprenoids – Monoterpenes – Sesquiterpenes – Diterpenes – Sesterterpenes – Tritepenes –– Higher terpenoids – Essential oils – Rosin and Oleoresins – Iridoids - Saponins – Steroids - 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.

TEACHERS AND EXAM BOARD

Exam Board

ANGELA BISIO (President)

PAOLO GIORDANI (President)

MARCO MILANESE

LESSONS

Class schedule

The timetable for this course is available here: Portale EasyAcademy

EXAMS

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.

Exam schedule