Chemistry of Natural Products
A.Y. 2026/2027
Learning objectives
The course aims at giving a general overview of the chemistry of natural products with emphasis on secondary metabolites, their occurrence, structure, biosynthesis and properties.
Expected learning outcomes
Students will acquire knowledge of the biosynthetic pathways leading to the major classes of natural products, being able to appreciate their relevance in various application fields.
Lesson period: Second semester
Assessment methods: Esame
Assessment result: voto verbalizzato in trentesimi
Single course
This course can be attended as a single course.
Course syllabus and organization
Single session
Responsible
Lesson period
Second semester
Course syllabus
Module 1 (3 credits):
Primary and secondary metabolism and their interconnections in the biosynthesis of natural products. Biosynthetic pathways and the role of enzymatic catalysis. Mechanistic and stereochemical aspects of enzymatic reactions and the role of the main cofactors. C-C bond-forming reactions: aldol condensation, Claisen condensation, alkylation reactions; oxidation and reduction reactions; carboxylation and decarboxylation; methylation and glycosylation reactions. Biosynthetic pathways and methods of investigation in the study of the biosynthesis of natural products. (1 credit)
The acetate pathway: fatty acids, polyketides, polyethers, and macrolides; biosynthesis of aromatic compounds: naphthoquinones and anthraquinones; polyketides from various starters: cannabinoids, tetracyclines, and anthracyclines. (1 CFU)
Shikimate pathway: benzoic acids and aromatic amino acids; phenylpropanoids: cinnamic acids, lignans and lignin, phenylpropenes and coumarins; aromatic polyketides: stilbenes, flavonoids, isoflavonoids, and flavolignans. (1 CFU)
Module 2 (3 CFU):
- The mevalonate and methylerythritol phosphate pathways: terpenoids and steroids (mevalonic acid and methylerythritol phosphate, hemiterpenes (C5), monoterpenes (C10), irregular monoterpenes, iridoids (C10), sesquiterpenes (C15), diterpenes (C20), sesterterpenes (C25), triterpenes (C30), steroids, tetraterpenes (C40)) (1 CFU).
- Alkaloids (ornithine-derived alkaloids, lysine-derived alkaloids, nicotinic acid-derived alkaloids, tyrosine-derived alkaloids, tryptophan-derived alkaloids, anthranilic acid-derived alkaloids, histidine-derived alkaloids, amination-derived alkaloids, purine alkaloids), modified peptides (penicillins, cephalosporins, and other β-lactams) (1 credit).
- Results and implications of chemical studies on natural products, chiral auxiliaries of natural origin; the role of natural products in human health care; organic phytonutrients, vitamins, and antioxidants; natural products as drug precursors: from research to industrialization (1 credit).
Primary and secondary metabolism and their interconnections in the biosynthesis of natural products. Biosynthetic pathways and the role of enzymatic catalysis. Mechanistic and stereochemical aspects of enzymatic reactions and the role of the main cofactors. C-C bond-forming reactions: aldol condensation, Claisen condensation, alkylation reactions; oxidation and reduction reactions; carboxylation and decarboxylation; methylation and glycosylation reactions. Biosynthetic pathways and methods of investigation in the study of the biosynthesis of natural products. (1 credit)
The acetate pathway: fatty acids, polyketides, polyethers, and macrolides; biosynthesis of aromatic compounds: naphthoquinones and anthraquinones; polyketides from various starters: cannabinoids, tetracyclines, and anthracyclines. (1 CFU)
Shikimate pathway: benzoic acids and aromatic amino acids; phenylpropanoids: cinnamic acids, lignans and lignin, phenylpropenes and coumarins; aromatic polyketides: stilbenes, flavonoids, isoflavonoids, and flavolignans. (1 CFU)
Module 2 (3 CFU):
- The mevalonate and methylerythritol phosphate pathways: terpenoids and steroids (mevalonic acid and methylerythritol phosphate, hemiterpenes (C5), monoterpenes (C10), irregular monoterpenes, iridoids (C10), sesquiterpenes (C15), diterpenes (C20), sesterterpenes (C25), triterpenes (C30), steroids, tetraterpenes (C40)) (1 CFU).
- Alkaloids (ornithine-derived alkaloids, lysine-derived alkaloids, nicotinic acid-derived alkaloids, tyrosine-derived alkaloids, tryptophan-derived alkaloids, anthranilic acid-derived alkaloids, histidine-derived alkaloids, amination-derived alkaloids, purine alkaloids), modified peptides (penicillins, cephalosporins, and other β-lactams) (1 credit).
- Results and implications of chemical studies on natural products, chiral auxiliaries of natural origin; the role of natural products in human health care; organic phytonutrients, vitamins, and antioxidants; natural products as drug precursors: from research to industrialization (1 credit).
Prerequisites for admission
Successful attendance requires knowledge of organic chemistry concepts acquired during the undergraduate bachelor program: acidity and basicity; stereochemistry (chirality, absolute configuration, conformations); structure and reactivity of the main functional groups and reaction mechanisms (substitutions, eliminations, additions, radical reactions, condensations, and rearrangements); knowledge of the main classes of biologically relevant organic compounds: sugars, amino acids, peptides. Basic knowledge of the main information that can be obtained through the use of structural analysis techniques of organic compounds, particularly mass spectrometry and nuclear magnetic resonance is recommended. Knowledge of the main metabolic pathways related to energy metabolism (glycolysis, tricarboxylic acids cycle) is desirable but not essential.
Teaching methods
Frontal lessons supported by projected material and explanations on the blackboard.
Teaching Resources
Recommended textbook: P. M. Dewick, Medicinal Natural Products. A Biosynthetic Approach, Third Ed., Wiley, Chichester, 2009
Assessment methods and Criteria
Module 1 (3 credits): Oral exam.
Module 2 (3 credits): Written exam, with the option of supplementing the grade by presenting a thematic analysis in a small group in class (discussion of a recent literature study, chosen in consultation with the instructor, for example, from the ACS Journal of Natural Products).
The grades obtained in both modules contribute equally to the final grade.
For both modules, the evaluation criteria adopted take into account the accuracy of the content presented, the student's proficiency in using specialized vocabulary, the ability to connect different topics, and the critical analysis of the material studied, also considering the interdisciplinary aspects of the course.
Module 2 (3 credits): Written exam, with the option of supplementing the grade by presenting a thematic analysis in a small group in class (discussion of a recent literature study, chosen in consultation with the instructor, for example, from the ACS Journal of Natural Products).
The grades obtained in both modules contribute equally to the final grade.
For both modules, the evaluation criteria adopted take into account the accuracy of the content presented, the student's proficiency in using specialized vocabulary, the ability to connect different topics, and the critical analysis of the material studied, also considering the interdisciplinary aspects of the course.
CHEM-05/A - Organic Chemistry - University credits: 6
Lessons: 48 hours
Professors:
Morelli Carlo, Silvani Alessandra
Shifts:
Professor(s)
Reception:
from Monday to Friday by appointment
Professor's office, Department of Chemistry.