Molecular Biology, Medicinal Chemistry and Computer Science for Pharmaceutical Applications

Activity type

Discipline chimiche

SSD

CHIM/06

Year

2nd year

Semester

2nd semester

CFU

6

Hours distribution

48 classroom hours

Lecturers

GIANCARLO FABRIZI

Activity type

Discipline chimiche

SSD

CHIM/10

Year

2nd year

Semester

1st semester

CFU

6

Hours distribution

48 classroom hours

Lecturers

CINZIA INGALLINA

The course aims to provide a general overview of the chemistry of food and natural products. The student-based learning objectives include knowledge on primary and secondary metabolism (in vivo presence, structure, biosynthesis, properties, and applications), the chemical composition of food (macro- and micronutrients and secondary metabolites), the impact of chemical compounds on food properties, and the main transformation processes during processing and storage.

By the end of the teaching, the student will be able to:

Knowledge and understanding
• Understand the basic chemical composition of foods, including the role of macronutrients, micronutrients, dietary fibre, proteins, lipids, carbohydrates, vitamins, and mineral salts in nutrition and human well-being.
• Comprehend the main chemical transformations of foods during processing and preservation (oxidation, enzymatic and non-enzymatic browning, protein denaturation, lipid degradation).
• Know the main natural compounds present in foods and plants (amino acids, lipids, carbohydrates, terpenes, flavonoids) and their general chemical properties.
• Understand the fundamental chemical reactions involving the most common functional groups in foods and natural compounds (oxidation, reduction, addition, condensation).
• Understanding the fundamental reactions of cellular metabolism
• Understanding the role of cofactors in enzymatic reactions
• Understanding and knowledge of the main biogenetic pathways
• Structural and chemical knowledge of the main classes of natural molecules

Ability to apply knowledge and understanding
• Analyse and describe the chemical composition of common foods, assessing their nutritional properties and potential effects on health.
• Interpret chemical and chemico-physical data related to foods, such as composition, nutrient content, organoleptic properties or quality analysis.
• Link basic organic chemistry principles to the transformations that occur in foods during production, preservation, and cooking.

Autonomy of judgement
• Critically evaluate scientific information on foods and natural compounds, distinguishing between evidence-based knowledge and unverified information.
• Be able to propose simple, reasoned assessments on the impact of specific foods and nutrients on well-being, in accordance with acquired knowledge.

Communication skills
• Clearly and coherently present concepts and data related to the chemistry of foods and natural compounds.
• Prepare brief reports or presentations on agreed topics, summarising scientific information and analytical data.

Learning skills
• Independently deepen understanding of concepts in food chemistry and natural compounds, developing a critical and systematic approach to scientific study.
• Be able to integrate knowledge of chemistry and nutrition with practical observations on major common foods.

Students must have basic knowledge of:
General chemistry: structure of matter, chemical bonds, fundamental chemical reactions.
Basic organic chemistry: main functional groups, elementary reactions of hydrocarbons, alcohols, aldehydes, ketones, carboxylic acids, and derivatives. Organic stereochemistry: definition of conformational and configurational stereoisomers. Chirotopic and achirotopic stereogenic elements. Prostereisomerism.

Module: CHEMISTRY OF FOOD
GENERAL SECTION

I. Review of basic organic chemistry: functional groups, with particular attention to the reactivity of carbonyl compounds, carboxylic acids, and their derivatives.
2. Organic reactions of the main metabolic pathways.
A. Kinetic and thermodynamic aspects, stereochemical aspects, role of cofactors and prosthetic groups (hemoglobin, biotin, FAD/FADH2, ATP, ADP, NAD+ and NADP+ (NADH and NADPH), PLP).
B. Alkylation, rearrangement, aldol and retro-aldol reactions, Claysen-type reactions, formation of imines and enamines, carboxylation and decarboxylation, elimination reactions, transamination reactions, oxidation and reduction reactions, glycosylation reactions.
3. Biomolecules. Amino acids: structure and acid-base properties; chemical synthesis of polypeptides, protein structure (notes). Carbohydrates: structure, chemical and stereochemical properties, D/L convention, major 5-, 5-, and 6-carbon monosaccharides, the cyclic structure of D-(+)-glucose, mutarotation, polysaccharides (notes)
4. Lipids. Classification, triglycerides, saponification and reduction reactions, phospholipids, fat-soluble vitamins, eicosanoids, terpenes, steroids (cholesterol).
5. Nucleic acids. Structure.

SPECIFIC SECTION

6. Biogenetic pathways. The shikimate pathway (chlorismic acid and derivatives) and the mevalonate pathway. Terpenes: classification and biosynthesis of monoterpenes, sesquiterpenes, diterpenes, sesterterpenes, triterpenes, and tetraterpenes.
7. The acetate pathway. Fatty acid biosynthesis: waxes, sterols, sphingolipids, triglycerides (structure, chemical-physical properties), unsaturated fatty acids, branched-chain fatty acids, prostaglandins, thromboxanes, leukotrienes. Polyketides: general description of biosynthesis. Aromatic polyketides, flavonoids, cannabinoids, aflatoxins, tetracyclines, macrolides (ansa macrolides, polyene macrolides).



Module: CHEMISTRY OF FOOD NATURAL COMPOUNDS
The course includes a general part, a specialised part, and an in-depth section. In the general part, introductory concepts related to the chemical composition of food and food safety are covered. The importance of a proper diet for personal well-being and the existence of disorders linked to the intake of specific nutrients are also emphasised. The specialised part deals instead with certain foods, highlighting their chemical composition, potential health benefits provided by specific components, and the analyses carried out to ensure authenticity and quality. The organisation within the various thematic units of the course is deeply interconnected, as discussing foods in the specialised part will refer back to their chemical composition, health properties, or issues related to their consumption described in the general part. In accordance with the depth of study requested by students in class, a division of the various topics into the following approximate hours is planned: point 1 = 24 hours (3 CFU); point 2 = 16 hours (2 CFU); point 3 = 8 hours (1 CFU).

General Part – Micro- and Macronutrients 3 CFU
Water. Structure, Physicochemical properties; hydrogen-bound, general properties and structural functions of water in food, free water, bound water; water activity; drinking water; mineral water, table water; treatment, hardness, analyses.
Micronutrients
Minerals: main elements, trace elements (Na, Ca, K, Cd, Mg, Mn, Fe, I, Se, F), bioavailability and bioaccessibility. Vitamins: Biological Role Requirement, Occurrence, Stability, Degradation. Water-soluble vitamins: vitamine e vitameri, Thiamine (Vitamin B1), Riboflavin (Vitamin B2), Pyridoxine (Pyridoxal, Vitamin B6), Nicotinamide (Niacin), Pantothenic Acid, Biotin, Folic Acid Cyanocobalamin (Vitamin B12), L-Ascorbic Acid (Vitamin C); fat-soluble vitamins; Retinol (Vitamin A), carotenoids, Calciferol (Vitamin D); α-Tocopherol (Vitamin E) Phytomenadione (Vitamin K1 Phylloquinone)
Macronutrients
Carbohydrates. Monosaccharides, Structure and Nomenclature, Configuration, Conformation, Fischer projection, Haworth projection, Physical Properties, Mutarotation, hemiacetal formation, alfa and beta anomers, disaccharides, Oligosaccharides, Structure and Nomenclature, Properties and Reactions, Polysaccharides (glycans). Reducing sugars, glucose, fructose, galactose, galactosemia, glycosidic linkages; inverted sugar; sucrose; lactose; maltose; homoglycans, heteroglycans; starch, amylose; amylopectin, enzymatic degradation of starch; endoplitting; exosplitting; debranching; modified starches, dextrin; cyclodextrin; glycogen; cellulose.
Proteins: General remarks, amino acids, essential amino acids, limiting amino acids, isoelectric point, peptide bond, primary structure; secondary structure; tertiary structure; quaternary structure; amino acid score; protein complementing; biological value; digestibility. Physical Properties Denaturation, Dissociation, chemical reactions, hydrolysis, Chemical and Enzymatic Reactions of Interest to Food Processing, Maillard reaction.
Lipids. Physico-chemical properties; Nomenclature and Classification: Saponification reaction Saponifiable and unsaponifiable Fraction, fatty acids, saturated and unsaturated, monounsaturated (MUFA); diunsaturated (DUFA); polyunsaturated (PUFA); EFA (essential fatty acids); Acylglycerols; Triglycerols; diglycerols, monoglycerols, phospholipids (phosphoglycerols and Sphingoglycerols), Glycolipids; Sphingolipids; Glycolipids; Phosphatidyl Derivatives; wax; Hydrocarbons, Steroids, Cholesterol; carotenoids, Rancidification; hydrolitic, ketonic, oxidative (autoxidation, Photooxidation) Antioxidants.

Special part - Foodstuff – 2 CFU
Sweeteners: Nutritional/Physiological Properties, Processing Properties; sweetening power; Individual Sugars and Sugar Alcohols: fructose, Maltodextrin, bulk sweeteners; sorbitol, xylitol, maltitol, acesulfame K, aspartame, aspartame-acesulfame, Cyclamic acid, Rebauside A; Stevioside; Saccharine; Sucralose; Sweet protein; Thaumatin; Monellin; Miraculin; Neotame.
Dietary Fibers: Soluble and insoluble fibre, resistant starch; Inulin; Pectine, Alginates, Carrageenans
Antinutritional factors
Cereal and Cereal products
Generality. Composition of the main cereals. World and Italian cereal production. Wheat. Wheat classes. T. aestivum (common wheat) and T. durum (durum wheat). Structure and composition of wheat kernels. Classification of flour: evaluation methods. Pasta and bread. Bakery products (overview). Rice. Rice species. Treatments made to obtain the commercial product.
Vegetable oils and edible fats
Olive oils. Composition and classification. Main analyses are foreseen by the European regulation to determine quality and genuineness.
Seed oils, hydrogenated fats and margarine: generality, production and refining technologies. Effects of technological treatments. Composition of the main seed oils.
Milk and derivatives
Definition. Composition with respect to milk protein and lipid fractions. Defects and alterations. Effect of heat treatments. Regulatory requirements. Milk cream: types and methods of production. Butter. Scheme of burrification processes.

DEEPENING– 1 CFU
Current topics (e.g., novel foods, emerging contaminants in food, organic/biodynamic/GM products) within the scope of food chemistry agreed upon with the students, who, with the knowledge and skills acquired, will be able to deepen their understanding and develop a critical reading. The aprofundamenti will actively involve students through the preparation of presentations.

Module: CHEMISTRY OF FOOD
For general section and biomolecules, an entry-level organic chemistry textbook.
For specific section: Medicinal Natural Products: A Biosynthetic Approach (3rd edition). Paul M. Dewick, John Wiley & Sons LTD.



Module: CHEMISTRY OF FOOD NATURAL COMPOUNDS
Mannina Luisa, Daglia Maria, Ritieni Alberto: la chimica degli Alimenti - Nutrienti e Aspetti Nutraceutici, CEA - Casa Editrice Ambrosiana
Slides

Module: CHEMISTRY OF FOOD
N/D
Module: CHEMISTRY OF FOOD NATURAL COMPOUNDS
- Belitz, H. D.; Grosch, W. ; Schieberle, P. FOOD CHEMISTRY di Springer Nature, 4a Edizione
- Cappelli Patrizia; Vannucchi Vanna: Chimica Degli Alimenti. Conservazione e trasformazioni. Ed. Zanichelli, Bologna, 2005
- P. Cabras, A Martelli - Chimica degli alimenti - Piccin, Padova.
- P. Cabras, C. Tuberoso – Analisi dei prodotti alimentari – Piccin, Padova.

Teaching is carried out through:
• Frontal lessons with multimedia aids.
• Exercises and case study discussions to stimulate the practical application of theoretical content and the development of critical skills.

Attendance at the course is optional.

The actual achievement of the expected learning outcomes by the student, in accordance with the teaching objectives, is assessed through the evaluation of the knowledge acquired in the two modules that make up the course:

Module Chemistry of Food (6 CFU): the exam consists of an oral test, during which the student will answer questions related to the general part (basic concepts on the chemical composition of foods, nutrients and their role in the organism) and the specific part (analysis of specific foods, chemical composition, nutritional properties, quality and safety), demonstrating the ability to connect the various sections of the programme.

Chemistry of Natural Compounds Module (6 CFU)
The exam consists of the preparation and presentation of a PPT document on a topic chosen by the student from among those covered in the course. During the presentation, the examining committee will ask the student questions to assess their preparation.
In addition to specific preparation on the exam topics, critical reasoning ability, autonomy in study, and the capacity to integrate knowledge from the two modules to formulate coherent explanations are evaluated.

The overall duration of the oral exam is approximately 20 minutes per module, varying according to the student’s preparation and expressive skills.

The course does not include intermediate assessments; the dates of the final exams are communicated annually to the University Offices and published on Infostud. During the course, students have the opportunity to self-assess through discussion and review of the concepts covered.

The final mark for the course will be calculated as the arithmetic mean of the grades obtained in the two modules. To pass the exam, a minimum of 18/30 must be attained in each module.
To achieve the maximum grade (30/30 with honours), the student must demonstrate an excellent knowledge of all topics, the ability to logically integrate them, and provide coherent explanations across the two modules.

Chemistry of Food (6 CFU): carbohydrates, proteins, lipids, saponification reaction, water activity, mutarotation reaction, furanoses and pyranoses, sweetening power, antioxidants, rancidity, Maillard reaction, caramelisation, caseins, functional foods, dietary fibre, starch gelatinisation, starch structure, caramelisation, difference between starch and cellulose.

Chemistry of Natural Compounds (6 CFU): Role of the amino acid histidine in enzymes. Difference between enantio- and diastereoselective reactions. Reactions with kinetic and thermodynamic control. Mechanism of biotin-mediated decarboxylation.

Module: CHEMISTRY OF FOOD

• Review
  of Organic Chemistry (functional groups)
  • Books: For
    
    a review of organic chemistry and for biomolecules, an introductory organic
    
    chemistry textbook.


• Kinetics
  and Thermodynamics. Stereochemistry.
  • Books: For
    
    a review of organic chemistry and for biomolecules, an introductory organic
    
    chemistry textbook.


• Reazioni
  organiche nelle biotrasformazioni
  • Books: For
    
    a review of organic chemistry and for biomolecules, an introductory organic
    
    chemistry textbook.


• Biomolecules
  • Books: For
    
    a review of organic chemistry and for biomolecules, an introductory organic
    
    chemistry textbook.


• Shikimate
  pathway
  • Books: Medicinal Natural Products: A Biosynthetic
    
    Approach (III edition). Paul M. Dewick, John Wiley & Son LTD


• Mevalonate
  pathway
  • Books: Medicinal Natural Products: A Biosynthetic
    
    Approach (III edition). Paul M. Dewick, John Wiley & Son LTD


• Acetate
  pathway
  • Books: Medicinal Natural Products: A Biosynthetic Approach (III edition). Paul M. Dewick, John Wiley & Son LTD

• General Part - Water 2 hours
  • Books: Food Chemistry - Belitz Chapter 0 and 23, slides


• General Part - Micronutrients 4 hours
  • Books: Food Chemistry - Belitz Chapter 6 and 7, slides


• General Part - Macronutrients - Carbohydrates 10 hours
  • Books: Food Chemistry - Belitz Chapter 4, slides


• General Part - Macronutrients - Lipids 4 hours
  • Books: Food Chemistry - Belitz Chapter 3, slides


• General Part - Macronutrients - Proteins 4 hours
  • Books: Food Chemistry - Belitz Chapter 1, slides


• Special Part - Sweeteners, Dietary Fiber, Antinutritional Factors and Functional Foods - 8 hours
  • Books: Food Chemistry - Belitz Chapter 8.8, slides


• Special Part - Cereals and cereal products, vegetable oils and fats, milk - 8 hours
  • Books: Food Chemistry - Belitz Chapter, slides