C9521 - METABOLITI SECONDARI: STRATEGIE BIOSINTETICHE

Learning outcomes

At the end of the course, the student will have in-depth chemical knowledge of the various classes of secondary metabolites, with particular reference to compounds of plant origin. Students will also acquire knowledge of the biosynthesis of the main secondary metabolites, which is useful for recognizing the biosynthetic pathway(s) involved in the production of the main secondary metabolites. Students will be able to recognize the building blocks that constitute the structures of secondary metabolites. Through laboratory exercises, students will acquire knowledge of extraction methods from complex matrices and metabolite characterization methods, as well as designing simple synthetic steps starting from building blocks.

Course contents

,between primary and secondary metabolites Definition of the characteristics and functions of secondary metabolites: Definition of the main building blocks used in the biosynthesis of secondary natural products Identification of the main biosynthetic building blocks: in particular C1, C2, C5, C6C3, C6C2N, C4N, C5N, and indole C2N Description of the reactions through which the building blocks are assembled in nature, divided according to the chemical mechanism, including alkylation reactions, Wagner-Meerwein rearrangements, aldol condensation, Claisen condensation, Dieckmann condensation, crossed Claisen condensation, hydrolysis and decarboxylation of beta-keto esters, formation of Schiff bases and Mannich reactions, transaminations, decarboxylations, oxidation and reduction reactions, phenolic oxidative coupling, and glycosylations Descriptions of the main enzymatic reactions involved in secondary metabolism Detailed description of: Mevalonate pathway: characteristics, linear and cyclic terpenes, terpenoids and steroids, cardiac glycosides, phytosterols, hormones. Biosynthesis of the main compounds from DMAPP and IPP. Acetate pathway: biosynthesis of saturated and unsaturated fatty acids, triglycerides, phospholipids, polyacetylenes, prostaglandins, thromboxanes, leukotrienes, aromatic polyketides, phenolic, naphthalene, and anthraquinone derivatives, anthrones, dianthrones, and sennosides, aflatoxins and cannabinoids, macrolide antibiotics, and tetracyclines. Shikimate pathway: shikimic acid and its derivatives, metabolites from chorismic acid, anthralic acid, phenylalanine, tyrosine, tryptophan, cinnamic acids, lignans and lignin, phenylpropanes, coumarins, furanocoumarins, Flavonoids, chalcones and stilbenes, chloramphenicol. Alkaloids: general notes. Alkaloids from ornithine, lysine, nicotinic acid, tyrosine, tryptophan, anthralic acid, and histidine. Description of established semisynthetic processes for obtaining bioactive metabolites of interest to the pharmaceutical, food, and cosmetic industries. Laboratory exercises on extraction techniques from complex matrices, characterization using basic instrumental techniques. Simple synthetic steps to improve the chemical characteristics of secondary metabolites.

Readings/Bibliography

To facilitate study, students will have access to all presentations shown during class and other supporting materials via the virtual platform. S

ome suggested textbooks are:

W.H. Brown, "Organic Chemistry," Edises, 3rd ed., 2005 (or later)

P. M. Dewick, "Chemistry, Biosynthesis, and Bioactivity of Natural Substances," Piccin

A. Bruni (ed.), "Pharmaceutical Biology," Pearson, 2014 Other suggested textbooks will be discussed in class.

Teaching methods

Classroom lectures Group activities and in-class presentations Laboratory exercises

Assessment methods

Learning will be assessed through an oral exam consisting of three parts: - general aspects of secondary metabolites, aspects related to biosynthetic processes, in-depth analysis of stereochemistry and the main reactions involved in biosynthetic processes, description of semi-synthetic processes - description of the biosynthetic steps, starting with the building blocks for obtaining a secondary metabolite described during the course - presentation of a group project (2-3 people) by presenting a fact sheet on a secondary metabolite (about ten molecules are indicated as starting points for group work), describing its source, possible therapeutic/nutritional/cosmetic uses, potential toxicity, design of its biosynthesis, and finally recent literature on its subject - evaluation of the laboratory report.

For students with learning disabilities or temporary or permanent disabilities: please contact the relevant University Office in advance. ([https://site.unibo.it/studenti-con-disabilita-e-dsa/it]). It will be the student's responsibility to propose any adjustments to the affected students, which must be submitted to the instructor for approval at least 15 days in advance, who will evaluate their suitability also in relation to the educational objectives of the course.

Teaching tools

Le lezioni si svolgono mediante videoproiezione di diapositive, condivisione di articoli recenti.

Il materiale (presentazioni e articoli) verrà messo a disposizione per il download da Virtuale.

Le esercitazioni di laboratorio si svolgono in laboratori attrezzati a posto singolo.

Office hours

See the website of Susanna Guernelli