Chemistry of Natural Organic Compounds and Foods

A.Y. 2021/2022
Overall hours
Learning objectives
The educational goal of integrated teaching is to provide basic notions related to organic substances of natural origin and foods with health properties. The first module, concerning natural substances, provides a description of the most important classes of substances, which are framed on the basis of the main biogenetic pathways and their own chemical reactivity. The second module, concerning foods, takes into consideration the composition of the main foods, emphasizing the characteristics and biological activity of the most interesting components.
Expected learning outcomes
At the end of the course, the students will know the composition of different foods, especially with regards to the most significant components from a health point of view, also considering the possible transformations induced by technological treatments and conservation. They will also know some issues related to quality and safety, in particular with regard to the possible presence of contaminants, the possible alterations, the main sophistications and the correct use of food additives. Students will also become familiar with the chemical structures of the main classes of natural substances and the chemical mechanisms constituting the basis of their biosynthesis. The laboratory tutorials have the objective to provide the students with the necessary familiarity on the main techniques of extraction, purification and analysis, in order to enable them to independently undertake studies and applications in wide interdisciplinary contexts, both in research and professional fields.
Course syllabus and organization

Single session

Lesson period
First semester
More specific information on the delivery modes of training activities for academic year 2021/22 will be provided over the coming months, based on the evolution of the public health situation
Prerequisites for admission
The integrated course is aimed at students who have passed the exams of General and Inorganic Chemistry and of Organic Chemistry.
The course requires the student to already have knowledge of the characteristics of organic and biological molecules. Previous Laboratory experiences, even if not necessary, will allow the student to better face the exercises of 1 CFU.
Assessment methods and Criteria
The exam consists of a written test aimed at ascertaining the student's knowledge both on the theoretical aspects of the subject and on the practical aspects dealt with during the laboratory exercises. The exam consists of exercises and open questions (for a total of three). The duration of the test is 1 hour and 30 minutes. Successful completion involves the acquisition of 10 points per exercise / open question. During the exam the correctness of expression of the candidate and of the chemical language will be evaluated. Furthermore, the ability to connect between the various topics covered in the course will be evaluated. The test covers all the topics of the course including those treated in the laboratory. Useful material to take the exam is the calculator.
Chemistry or natural organic compounds
Course syllabus
TOPIC n.1 (1 CFU) Main reaction mechanisms involved in hte synthesis of secondary metabolites: alkylation, transposition, condensation, redox reactions, oxidative coupling in phenols, glycosylation reactions. Carbohydrates. Definition and classification.Monosaccharides. Aldoses e chetoses, configuration, D and L series. Emiacetalic cyclic structures, Fischer projections, Haworth formulae, conformation of pyranosides. Mutarotation. Main monosaccharides: glucose, fructose, ribose. Reactions of monosaccharides: formation of esters and ethers, oxydation e riduction, reactions with amines. Formation of O- and N- glycosides. Examples of pharmacologically relevant glucosides. Hydrolysis of glucosides. Vitamine C, aminosugars.
Disaccharides. Structure and property of the main disaccharides: maltose, cellobiose, lactose, saccharose. Sweeteners. Structrure and function of the main polisaccharides: starch, cellulose, glycogen, gums, cyclodextrins.
TOPIC n.2 (1 CFU) The biogenetic pathways of acetate: fatty acids and polyketides. Lipids. Definition and classification. Fatty acids and triacylglicerols. Preparation of natural soaps. Micelle formation. Synthetic detergents. Phospholipids: structure and biological importance. Prostaglandins and steroids. Poliketides: biological activity. Examples of biosynthesis: emodin, hypericin, usnic acid, griseofulvin. Sinthessi of aromatic poliketides, simple phenols, antraquinones. Tetracyclines. Macrolide antibiotics.
TOPIC n.3 (1 CFU) The mevalonate and methylerytritol-phosphate biogenetic pathways: terpenoids and sterols. Terpenes: classification and biosynthesis, chemical properties. Steroids: structure and stereochemistry of plant and animal sterols, steroidal saponins, phytosterols. Examemples of biosynthesis: tujone, pinene, menthol, thymol. The biogenetic pathway of shikimic acid. Biosynthesis of phenols, poliphenols and phenylpropanoids. Cinnamic acids and their transfomraiton products (estragol, eugenol, anetol, etc). Reactions of oxidative coupling: lignans, neolignans e lignin. Benzoic acids, coumarins and their derivatives. Furanocoumarines: photodynamic activity, biosynthesis of psoralene. Flavonoids and isoflavones. Terpenoid quinones . Natural colorants and elements of tinctorial chemistry.
TOPIC n.4 (1 CFU) Aminoacids. Structure and configuration. Behaviour of aminoacids in solution: acidity and basicity. Isolectric point. Nucleci acids: Composition, structure of nucleosides and nucleotides. Structure nucleic acids. Three dimensional structureof the double helix.
Alkaloids. Biological amines and their activity. Pyrrolidin and tropa alkaloids: hyosciamin, cocaine, atropine. Alkaloids isoquinolinic: reticuline, papaverine, morfine, codeine and berberine. Pyridine alkaloids: biosynthesis of nicotinic acid, nicotine and anabasine. Indole alkaloids: psylocibine, lysergic acid.
TOPIC n.5 (1 CFU ): Laboratory tutorials, dealing with the main extraction, isolation and identification of natural organic substances.
Teaching methods
Lectures, practical laboratory exercises, classroom exercises. Laboratory exercises are subject to the attendance of a safety lesson and a test. The articulation of the themes over time will follow the program with the exception of the theoretical part linked to the workshops which will be treated in advance of the practical exercises.
Teaching Resources
P.M. Dewick: Chimica, biosintesi e bioattività delle sostanze naturali- Piccini (Ed. Italiana).
Organic Chemistry text book at university level, for instance:
W. H. Brown: Introduzione alla Chimica Organica, EdiSES (with exercise text book) J. Mc Murry: Fondamenti di Chimica Organica, ed., Zanichelli
Slides will be available on ARIEL platform.
Chemistry of healthy foods
Course syllabus
· Organic nutrients, simple sugars, polysaccharides, amino acids, proteins, lipids, minor components, macro and microelements, anti-nutritional factors, main analytical determinations.
· Thermal stability of the main nutrients and changes induced by production technologies, toxicological consequences.
· Additives: regulations and use criteria, toxicological problems. Main classes: preservatives, antioxidants, gelling agents, thickeners, emulsifiers, sugar substitutes, dyes, fat substitutes.
· Chemical contamination of foods of natural and / or anthropogenic origin: heavy metals, PAHs, PCBs, polychlorinated dibenzoxoxins / furans, agrochemicals, mycotoxins.
· Lipids: composition, functional properties of polyunsaturated fatty acids, hydrolytic and oxidative rancidity, olive oil, preparation, refining process, main seed oils for food use. Analytical problems.
· Cereals: wheat composition, characteristics of the main polysaccharides, preparation of bread and pasta. Other cereals: rice, rye, corn, oats, barley. Pseudocereals.
· Legumes: composition, nutritional characteristics, analytical problems.
· Honey: composition, nutritional characteristics, analytical problems.
· Fruits and vegetables: chemical composition, production technology, health properties.
· Milk: composition, nutritional characteristics, production technology, analytical problems.
· Meat: composition, nutritional characteristics, conservation methods.
· Fish: composition, nutritional characteristics, conservation methods.
· Eggs: chemical composition, health properties.
· HACCP: principles of the system and food safety
Teaching methods
frontal lessons with slides (slides available on the web-site ARIEL)
Teaching Resources
- La chimica e gli alimenti. edited by L. Mannina, M. Daglia, A. Ritieni. CEA Casa Editrice Ambrosiana (2020).
- Chimica degli alimenti edited by P. Cabras and A. Martelli, Piccin Editore, 2004 (in Italian).
The slides of the lessons, notes, and other scientific papers provided by the teacher are available on the Ariel platform.
Chemistry of healthy foods
CHIM/10 - FOOD CHEMISTRY - University credits: 6
Lessons: 48 hours
Chemistry or natural organic compounds
CHIM/06 - ORGANIC CHEMISTRY - University credits: 5
Single bench laboratory practical: 16 hours
Lessons: 32 hours
Professor: Borgonovo Gigliola
Professor: Borgonovo Gigliola
Turno 1
Professor: Borgonovo Gigliola
Turno 2
Professor: Borgonovo Gigliola