1. komponenta

Lecture type	Total
Lectures	30
Laboratory exercises	30

* Load is given in academic hour (1 academic hour = 45 minutes)

PURPOSE:
The purpose of the course is to present chemistry of natural compounds involved in secondary metabolism of living beings. In the framework of this course, students will be introduced with the structures, chemical reactions and biological activity of representatives of natural compounds.

THE CONTENTS OF THE COURSE:
1. Lipids. Triglycerides and fatty acids (saturated and unsaturated). The reactions of fatty acids. Phospholipids.
2. Non-glicerides (sphingolipids, steroids, wax). Biomembranes, complex lipids (lipoproteins, glycolipids).
3. Prostaglandins and related compounds. Nomenclature and synthesis. Prostacyclins, thromboxanes, leukotrienes, epoxyeicosatrienoic acid.
4. Steroids: structure and function. Cholesterol. Bile salts. Steroid hormones.
5. Terpenes: isoprene rule. Biosynthesis of terpenoids. Determination of the structure of terpenoids. Monoterpenoids. Sesquiterpenoids. Diterpenoids. Triterpenoids. Polyterpenoids.
6. Vitamins: water-soluble vitamins, fat-soluble vitamins.
7. 1st test.
8. Alkaloids. Structural characteristics, physical properties and functions. Extraction and isolation. Classification of the alkaloids according to chemical structure. Tropane, quinoline, isoquinoline, indole, purine alkaloids.
9. Phenols, natural dyes and pigments I: Flavonoids. Classification, biogenesis, natural source, isolation and separation, total synthesis. Anthocyanidins. Leukoanthocyanines and leukoanthocyanidins. Tannins. Naphthoquinones. Coumarins.
10. Phenols, natural dyes and pigments II: Flavonoids, Quinonoids, polyenes, carotenoids.
11. Plant hormones: auxins, gibberellins, cytokinins, brassinosteroids, ethylene, abscisic acid, jasmonic acid.
12. Insect growth regulators: pheromones and allelochemicals. The hormones of the endocrine glands: brain hormones and juvenile hormones: sesquiterepenes, juvenile. Secretions of exocrine glands: pheromones (sex, aggregation, alarm, epideictic, trail. Total synthesis of pheromones. Pyrethrins and synthetic pyrethroids analogues.
13. Marine natural products: terpenoids, sesquiterpenes, diterpenes, carotenoids, sterols, phenols, halogenated compounds, adenochromes, marine toxins, bioluminescence.
14. 2nd test.

DEVELOPMENT OF GENERAL AND SPECIFIC COMPETENCIES OF STUDENTS:
Knowledge of different classes of natural compounds, their structural characteristics, basic chemical reactions and bioactive properties of natural compounds as secondary metabolites.

STUDENTS' OBLIGATIONS:
It is mandatory to participate in lectures and laboratory practices, as well as in colloquia organized during classes to evaluate knowledge.

REQUIREMENTS FOR OBTAINING A SIGNATURE:
Regular attendance at lectures and completed laboratory exercises.

TEACHING METHODS:
Lectures and laboratory exercises

METHOD OF EXAMINATION OF KNOWLEDGE AND EXAMINATION:
Knowledge test through two colloquia, written and oral exam.

METHOD OF MONITORING THE QUALITY AND PERFORMANCE OF COURSES:
Student survey

METHODOLOGICAL PREREQUISITES:
Passed exam from the courses: Organic Chemistry I and II, Chemistry of Natural and Synthetic Polymers and Biochemistry

PROGRAM LEARNING OUTCOMES:
1. To apply more complex chemical principles that continue the basic knowledge of chemistry acquired in undergraduate study
2. To apply ideas within scientific research work
3. To connect basic facts, concepts, chemical principles and theories related to advanced areas of chemistry and chemical technologies
4. To integrate the knowledge needed to process complex ideas
5. To use advanced laboratory procedures and instrumentation within chemical synthesis and analysis

TEACHING UNITS WITH ASSOCIATED LEARNING OUTCOMES AND EVALUATION CRITERIA

Teaching unit
1. Lipids

Learning outcomes:
- know the general structural characteristics and properties of fatty acids, triacylglycerol and wax
- define complex lipids (phospholipids, sphingolipids and glycosphingolipids)
- explain the basics of fatty acid biosynthesis
- know the general structure and biological significance of prostaglandins

Evaluation criteria:
- draw structures of representatives of saturated and unsaturated fatty acids and triglycerides (simple and mixed)
- distinguish the building blocks of complex lipids and their biological significance
- explain the nomenclature of prostaglandins

Teaching unit
2. Steroids

Learning outcomes:
- define the structures and significance of steroid sex hormones and corticoids

Evaluation criteria:
- illustrate with examples steroids such as sex hormones, mineralocorticoids and glucocorticoids

Teaching unit
3. Terpenes

Learning outcomes:
- explain the isoprene rule and classify terpenes according to the number of isoprene units
- explain the biosynthesis of terpenoids

Evaluation criteria:
- determine the type of terpene according to the number of isoprene building units
- list representatives of monocyclic, bicyclic monoterpenes, sesquiterpenes and diterpenes and tetraterpenes

Teaching unit
4. Alkaloids

Learning outcomes:
- define alkaloids with respect to nitrogen content and biosynthetic origin
- know the general physical properties and functions of alkaloids in plants
- define the classification of alkaloids according to chemical structure, pharmacological action and biological origin

Evaluation criteria:
- list the representatives and biological properties of the following groups of alkaloids: protoalkaloids, alkaloids with pyrimidine, piperidine, pyrrolidine, quinoline, isoquinoline and indole rings, tropanic and purine alkaloids

Teaching unit
5. Natural colors and pigments

Learning outcomes
- define the structural characteristics of flavonoids, quinonoids, anthraquinones, anthocyanins, tannins and carotenoids

Evaluation criteria:
- draw the chemical structures of the representatives of the mentioned classes and give an example of total synthesis

Teaching unit
6. Vitamins

Learning outcomes:
- know the division of vitamins, their biological activity and the source of vitamins in nature

Evaluation criteria:
- draw the structures of water- and fat-soluble vitamins
- distinguish biologically active forms of molecules

Teaching unit
7. Natural antibiotics

Learning outcomes:
- classify natural antibiotics according to chemical structure

Evaluation criteria:
- recognize and distinguish the structural characteristics of beta-lactams, tetracyclines, macrolides, polyenes, anthracyclines, aminoglycosides, polypeptide antibiotics

Teaching unit
8. Plant and insect growth regulators

Learning outcomes:
- know the growth regulators and hormones of plants and insects, their biological properties and source

Evaluation criteria:
- define the basic structural characteristics of growth regulators, sex pheromones, plant hormones
- give an example of total pheromone synthesis

1. 1. To apply more complex chemical principles that continue the basic knowledge of chemistry acquired in undergraduate study
2. 2. To analyze the structures of natural compounds and classification into appropriate classes of compounds and to compare the building units of complex natural compounds
3. 3. To apply general physical and biological (pharmacological toxicological and ecological) properties of natural compounds involved in secondary metabolism
4. 4. To interpret the total synthesis for the representatives of the mentioned natural compounds
5. 5. To use advanced laboratory procedures and instrumentation within chemical synthesis and analysis

1. S. V. Bhat, Chemistry of Natural Products, Narosa Publiching House Pvt. Ltd., New Delhi, Indi, 2005.,
2. T. W. Graham Solomons, C. B. Fryhle, Organic Chemistry, John Wiley and Sons, Inc., New York, 2004.,
3. S. H. Pine, Organska kemija (prijevod I. Bregovec, V. Rapić), Školska knjiga, Zagreb, 1994.,
4. L. G. Wade, Organic Chemisty, 6th, Pearson Education, Inc., New Jersey, 2006.,

Izborni kolegij - Regular modul - Applied Organic Chemistry