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

To know the major chemical classes of plant secondary metabolites of pharmaceutical interest.

AIMS AND LEARNING OUTCOMES

Aim of the course is to provide basic information for the knowledge of the major chemical classes of plant secondary metabolites of pharmaceutical interest and their biosynthesis related 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 comprises online classes (hub Microsoft Teams, https://cedia.unige.it/didattica-a-distanza). The Team based Learning methodology is applied. The illustrated educational materials (slides) 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 insert notes, comments etc. Ongoing 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 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

Exam Board

ANGELA BISIO (President)

GUENDALINA OLIVERO

PAOLO GIORDANI (President Substitute)

VALERIA IOBBI (Substitute)

LESSONS

Class schedule

The timetable for this course is available here: Portale EasyAcademy

EXAMS

EXAM DESCRIPTION

The exam is online (“Aulaweb esami”, https://esami2020.aulaweb.unige.it/) and consists of a quiz, covering all the topics listed in the file on Aulaweb: " SCHEDA insegnamento Costituenti bioattivi delle droghe vegetali".

The quiz is made up of 15 questions. For each correct answer, 1 to 2 points, or fractions thereof, are awarded, up to a maximum of 30 points. The student can only make one attempt to complete the quiz and has a total of 13 minutes from the moment he clicks the start attempt (AVVIA IL TENTATIVO) button. The questions are presented in a sequence and it is not possible to leave pending questions (if you go to the next question you cannot go back). To conclude the test, the student must click on the “end the attempt” button (TERMINA IL TENTATIVO) and then on the “send all and finish” button (INVIA TUTTO E TERMINA) within the maximum time limit.

DSA Students who notified it in good time in good time (two days before the exam date) will benefit from the additional time required by current legislation.

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

ASSESSMENT METHODS

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

Exam schedule