OVERVIEW

The main classes of secondary metabolites present in plant drugs of pharmaceutical interest are systematically described, with references to the main metabolic pathways in higher plants

AIMS AND CONTENT

LEARNING OUTCOMES

Aim of the course is to know the major chemical classes of plant secondary metabolites of pharmaceutical interest.

AIMS AND LEARNING OUTCOMES

The course aims to provide basic information on the main chemical classes of plant secondary metabolites of pharmaceutical interest and their biosynthesis in relation to the various plant 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 Team-Based Learning methodology is applied in the course. Illustrated teaching materials (slides) are provided to students at the beginning of the lessons through Aulaweb. Students are encouraged to download the materials from the start of the course, so they have a reference during the lessons for adding notes, comments, etc. Learning assessments are included.

Any Student with documented Specific Learning Disorders (SLD), or with any special needs, shall reach out to the Lecturer(s) and to the dedicated SLD Representative in the Department (Prof. Luca Raiteri, Luca.Raiteri@unige.it ) before class begins, in order to liaise and arrange the specific learning methods and ensure proper achievement of the learning aims and outcomes. IMPORTANT: any request for compensatory tools and adaptations in the learning assessments MUST be done within 10 working days before the date of the learning assessment according to the instructions that can be found at https://unige.it/disabilita-dsa/comunicazioni

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 the construction mechanisms of secondary metabolites, the chemical classes of bioactive compounds, the main biosynthetic reactions. CBV1d_Metabolomics, fluxomic and systems biology. CBV1e_Traditional medicines, ecopharmacognosy, access to biome and biopiracy. Legislative outline about the cultivation, harvesting and first processing of medicinal plants. Economic observatory of the medicinal plant sector. The sector plans. Plant sources of the bioactive compounds used in therapy: breeding, harvest, drying. CBV1f_ Plant sources of the bioactive compounds used in therapy: stabilization, quality control. The sites of the biosynthesis of the secondary metabolites. Extraction of bioactive plant compounds. CBV1g_Plant biotechnologies.

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

CBV3_The acetate pathway. Fatty acids, prostaglandins, phytoprostanes, acetylenic fatty acids.

CBV4a_Amino acids. Cyanogenic glycosides, 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. CBV5b_Alkaloids derived from ornithine: pyrrolidine, tropane, pyrrolizidine alkaloids. CBV5c_Alkaloids derived from lysine: piperidine, quinolizidine, indolizidine alkaloids. Alkaloids derived from nicotinic acid: pyridine alkaloids. CBV5d_Alkaloids derived from tyrosine, part 1: phenylethylamines, simple tetrahydroisoquinoline alkaloids, betalains, benzyltetrahydroisoquinoline alkaloids, curare. CBV5e_Alkaloids derived from tyrosine, part 2: modified benzyltetrahydroisoquinoline, phenethylisoquinoline, terpenoid tetrahydroisoquinoline alkaloids, Amaryllidaceae alkaloids. CBV5f_Alkaloids derived from tryptophan, part 1: simple indole alkaloids, simple β-carboline alkaloids, terpenoid indole alkaloids. CBV5g_Alkaloids derived from tryptophan, part 2: quinoline, pyrroloindole, Ergot alkaloids. CBV5h_Alkaloids derived from anthranilic acid: quinazoline, quinoline, acridine alkaloids. Alkaloids derived from histidine: imidazole alkaloids. Alkaloids derived by amination reactions: acetate-derived, phenylalanine-derived, 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.

TEACHERS AND EXAM BOARD

LESSONS

LESSONS START

The earliest possible date after the start of the course lessons

Class schedule

The timetable for this course is available here: Portale EasyAcademy

EXAMS

EXAM DESCRIPTION

The exam takes place in person in a dedicated classroom. Each student has access to a personal computer, through which they access the exam session via “Aulaweb exams” The exam consists of a quiz covering all the topics listed in the file available on Aulaweb titled “SCHEDA insegnamento Costituenti bioattivi delle droghe vegetali”.

The quiz comprises 15 questions. For each correct answer, 1 to 2 points, or fractions thereof, are awarded, up to a maximum of 30 points. Students can make only one attempt to complete the quiz and have a total of 16 minutes from the moment they click the AVVIA IL TENTATIVO button. The questions are presented sequentially, and it is not possible to leave questions unanswered (once you move to the next question, you cannot go back). To complete the exam, students must click the TERMINA IL TENTATIVO button and then the INVIA TUTTO E TERMINA button at the bottom before the maximum time expires.

The exam is considered passed only if a score ≥18 is achieved. The grade obtained will be averaged with that obtained in the Plant Biology part to give the final grade of the two integrated courses. The two exams must be taken on the same day, and both must be passed with a grade ≥18.

The possibility of rescheduling the exam is given only in exceptional cases and is discussed on the same day of the exam with the commission.

Any Student with documented Specific Learning Disorders (SLD), or with any special needs, shall reach out to the Lecturer(s) and to the dedicated SLD Representative in the Department (Prof. Luca Raiteri, Luca.Raiteri@unige.it ), in order to benefit from the additional time required by current legislation. VERY IMPORTANT: any request for compensatory tools and adaptations in the exam MUST be done within 10 working days before the date of the exam according to the instructions that can be found at https://unige.it/disabilita-dsa/comunicazioni

ASSESSMENT METHODS

Correctness of the answers to the quiz questions. Total score resulting from the sum of partial scores.

FURTHER INFORMATION

Ask the professor for other information not included in the teaching schedule