Chemistry of Health Foods and Phytocomplexes
A.Y. 2025/2026
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 part of the program, 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.
Lesson period: First 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
First semester
Course syllabus
Chemistry of health foods:
Organic nutrients, simple sugars, polysaccharides, amino acids, proteins, lipids, minor components, macro and microelements, antinutritional factors, main analytical determinations.
· Thermal stability of the main nutrients and changes induced by production technologies, toxicological consequences.
· Additives: regulations and criteria for use, toxicological issues. Main classes: preservatives, antioxidants, gelling agents, thickeners, emulsifiers, sugar substitutes, colorants, fat substitutes.
· Chemical contamination of foods of natural and/or anthropogenic origin: heavy metals, PAHs, PCBs, polychlorinated dibenzodioxins/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 issues.
· Cereals: composition of wheat, characteristics of the main polysaccharides, preparation of bread and pasta. Other cereals: rice, rye, corn, oats, barley. Pseudocereals.
· Legumes: composition, nutritional characteristics, analytical issues.
· Honey: composition, nutritional characteristics, analytical issues.
· Fruits and vegetables: chemical composition, production technology, health properties.
· Milk: composition, nutritional characteristics, production technology, analytical issues.
Meat: composition, nutritional characteristics, methods of preservation.
· Fish: composition, nutritional characteristics, methods of preservation.
· Eggs: chemical composition, health properties.
· HACCP: principles of the system and food safety
Chemistry of phytocomplexes:
TOPIC n.1 The biogenetic pathway of acetate: saturated and unsaturated fatty acids and polyketides. Triacylglycerols: preparation of natural soaps (with reaction mechanism). Formation of micelles. Anionic, cationic and non-ionic synthetic detergents. Polyketides. Examples of biosynthesis starting from acetyl-CoA: orsellinic acid, emodin, aloe-emodin.
TOPIC n.2 Terpenes: classification and biosynthesis starting from acetyl-CoA via HMG-CoA, MVA, IPP and DMAPP. Monoterpenes, sesquiterpenes, notes on diterpenes, triterpenes and tetraterpenes (carotenoids). Examples of biosynthesis: geraniol, linalool, nerol and their acetates, farnesol, limonene. The biogenetic pathway of shikimic acid: biosynthesis of shikimic acid from D-erythrose-4-P. Phenolic acids: biosynthesis of gallic acid, hydrolysable tannins, structure of ellagic acid, ellagitannins. Biosynthesis of phenylalanine and tyrosine from shikimic acid via chorismic acid. Phenylpropanoids: biosynthesis of cinnamic acids (caffeic acid, ferulic acid, sinapyl acid) from Phe and Tyr. Cinnamic alcohols. Biosynthesis of lignans by oxidative coupling reactions. Chalcones, flavonoids and anthocyanins: structure and biosynthesis. Natural dyes and notes on dyeing chemistry.
TOPIC n.3. Alkaloids. Biological amines (structure of serotonin, dopamine, histamine). Biosynthesis of mescaline. Pyrrolidine alkaloids: biosynthesis of hygrine from arginine via putrescine. Tropane alkaloids: structure of cocaine. Isoquinoline alkaloids: biosynthesis of papaverine via reticulin. Notes on the structure of morphine, codeine and their derivatives. Indole alkaloids: structure of psilocybin. Main conventional and innovative extraction techniques (enzymatic, extractions assisted by microwaves and ultrasound, accelerated extractions with solvents and extraction with supercritical fluids). For each of these techniques, the following will be described: the theoretical foundations, the equipment used and the advantages/disadvantages
TOPIC no. 4: Practical exercises on some extraction, isolation and identification techniques of natural organic substances: a) steam distillation of plant material to obtain essential oils. TLC analysis of essential oils (operating principles). Notes on the use of development reagents. b) Saponification reactions of plant fats. c) solvent extraction.
Organic nutrients, simple sugars, polysaccharides, amino acids, proteins, lipids, minor components, macro and microelements, antinutritional factors, main analytical determinations.
· Thermal stability of the main nutrients and changes induced by production technologies, toxicological consequences.
· Additives: regulations and criteria for use, toxicological issues. Main classes: preservatives, antioxidants, gelling agents, thickeners, emulsifiers, sugar substitutes, colorants, fat substitutes.
· Chemical contamination of foods of natural and/or anthropogenic origin: heavy metals, PAHs, PCBs, polychlorinated dibenzodioxins/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 issues.
· Cereals: composition of wheat, characteristics of the main polysaccharides, preparation of bread and pasta. Other cereals: rice, rye, corn, oats, barley. Pseudocereals.
· Legumes: composition, nutritional characteristics, analytical issues.
· Honey: composition, nutritional characteristics, analytical issues.
· Fruits and vegetables: chemical composition, production technology, health properties.
· Milk: composition, nutritional characteristics, production technology, analytical issues.
Meat: composition, nutritional characteristics, methods of preservation.
· Fish: composition, nutritional characteristics, methods of preservation.
· Eggs: chemical composition, health properties.
· HACCP: principles of the system and food safety
Chemistry of phytocomplexes:
TOPIC n.1 The biogenetic pathway of acetate: saturated and unsaturated fatty acids and polyketides. Triacylglycerols: preparation of natural soaps (with reaction mechanism). Formation of micelles. Anionic, cationic and non-ionic synthetic detergents. Polyketides. Examples of biosynthesis starting from acetyl-CoA: orsellinic acid, emodin, aloe-emodin.
TOPIC n.2 Terpenes: classification and biosynthesis starting from acetyl-CoA via HMG-CoA, MVA, IPP and DMAPP. Monoterpenes, sesquiterpenes, notes on diterpenes, triterpenes and tetraterpenes (carotenoids). Examples of biosynthesis: geraniol, linalool, nerol and their acetates, farnesol, limonene. The biogenetic pathway of shikimic acid: biosynthesis of shikimic acid from D-erythrose-4-P. Phenolic acids: biosynthesis of gallic acid, hydrolysable tannins, structure of ellagic acid, ellagitannins. Biosynthesis of phenylalanine and tyrosine from shikimic acid via chorismic acid. Phenylpropanoids: biosynthesis of cinnamic acids (caffeic acid, ferulic acid, sinapyl acid) from Phe and Tyr. Cinnamic alcohols. Biosynthesis of lignans by oxidative coupling reactions. Chalcones, flavonoids and anthocyanins: structure and biosynthesis. Natural dyes and notes on dyeing chemistry.
TOPIC n.3. Alkaloids. Biological amines (structure of serotonin, dopamine, histamine). Biosynthesis of mescaline. Pyrrolidine alkaloids: biosynthesis of hygrine from arginine via putrescine. Tropane alkaloids: structure of cocaine. Isoquinoline alkaloids: biosynthesis of papaverine via reticulin. Notes on the structure of morphine, codeine and their derivatives. Indole alkaloids: structure of psilocybin. Main conventional and innovative extraction techniques (enzymatic, extractions assisted by microwaves and ultrasound, accelerated extractions with solvents and extraction with supercritical fluids). For each of these techniques, the following will be described: the theoretical foundations, the equipment used and the advantages/disadvantages
TOPIC no. 4: Practical exercises on some extraction, isolation and identification techniques of natural organic substances: a) steam distillation of plant material to obtain essential oils. TLC analysis of essential oils (operating principles). Notes on the use of development reagents. b) Saponification reactions of plant fats. c) solvent extraction.
Prerequisites for admission
The integrated teaching is aimed at students who have passed the exams of General and Inorganic Chemistry and Organic Chemistry.
The course requires that the student already has knowledge of the characteristics of organic and biological molecules. Previous laboratory experiences, even if not necessary, will allow the student to better deal with the exercises required for a CFU.
The course requires that the student already has knowledge of the characteristics of organic and biological molecules. Previous laboratory experiences, even if not necessary, will allow the student to better deal with the exercises required for a CFU.
Teaching methods
Frontal lectures, practical laboratory exercises, classroom exercises. The laboratory exercises are subject to the attendance of a lesson on safety and a test. The articulation of the topics over time will follow the program with the exception of the theoretical part related to the laboratories that will be treated in advance with respect to the practical exercises. As reported in the Manifesto, the food chemistry module will be delivered partly through frontal lectures with slides available on MyAriel, and part of the course will be delivered with an innovative teaching approach.
Teaching Resources
- La chimica e gli alimenti. a cura di L. Mannina, M. Daglia, A. Ritieni. CEA Casa Editrice Ambrosiana (2020)
- Chimica degli Alimenti a cura di P. Cabras e A. Martelli, Piccin Editore, 2004
- P.M. Dewick: Chimica, biosintesi e bioattività delle sostanze naturali- Piccini (Ed. Italiana).
In addition to a college-level organic chemistry fundamentals text, for example:
- W. H. Brown: Introduzione alla Chimica Organica, EdiSES (e relativo eserciziario) J. Mc Murry: Fondamenti di Chimica Organica, ed., Zanichelli
The slides shown in class are available on the MyAriel platform.
- Chimica degli Alimenti a cura di P. Cabras e A. Martelli, Piccin Editore, 2004
- P.M. Dewick: Chimica, biosintesi e bioattività delle sostanze naturali- Piccini (Ed. Italiana).
In addition to a college-level organic chemistry fundamentals text, for example:
- W. H. Brown: Introduzione alla Chimica Organica, EdiSES (e relativo eserciziario) J. Mc Murry: Fondamenti di Chimica Organica, ed., Zanichelli
The slides shown in class are available on the MyAriel platform.
Assessment methods and Criteria
The exam consists of a written test aimed at assessing the student's knowledge of both the theoretical aspects of the subject and the practical aspects covered 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. Correct execution entails the acquisition of 10 points per exercise/open question. During the exam, the candidate's correctness of expression and chemical language will be assessed. Furthermore, the ability to connect the various topics covered in the course will be assessed. The test covers all the topics of the course including those covered in the laboratory. Useful material for taking the exam is the calculator.
For DSA students
In order to take advantage of the facilities provided, it is necessary to have communicated your situation to the Disabled Office of UniMI http://www.unimi.it/studenti/serviziodisabiliedsa.htm. Furthermore, it is suggested to consult with the teacher during attendance or during the preparation phase of the exam in order to receive useful suggestions; in any case it is mandatory to communicate that you intend to use the compensatory/dispensatory tools with sufficient notice (at least 10 days) to the teacher in order to agree on the exam methods, which remain the responsibility of the teacher.
For DSA students
In order to take advantage of the facilities provided, it is necessary to have communicated your situation to the Disabled Office of UniMI http://www.unimi.it/studenti/serviziodisabiliedsa.htm. Furthermore, it is suggested to consult with the teacher during attendance or during the preparation phase of the exam in order to receive useful suggestions; in any case it is mandatory to communicate that you intend to use the compensatory/dispensatory tools with sufficient notice (at least 10 days) to the teacher in order to agree on the exam methods, which remain the responsibility of the teacher.
CHIM/06 - ORGANIC CHEMISTRY - University credits: 4
CHIM/10 - FOOD CHEMISTRY - University credits: 6
CHIM/10 - FOOD CHEMISTRY - University credits: 6
Single bench laboratory practical: 16 hours
Lessons: 72 hours
Lessons: 72 hours
Professors:
Borgonovo Gigliola, Lammi Carmen
Shifts:
Professors:
Borgonovo Gigliola, Lammi Carmen
Turno 1
Professor:
Borgonovo GigliolaTurno 2
Professor:
Borgonovo GigliolaProfessor(s)