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Lecturer(s)
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Šebela Marek, prof. Mgr. Dr.
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Course content
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1. Difference between primary and secondary metabolism. Natural substances and a brief history of their study. Methods of studying secondary metabolism. Isolation and use of secondary metabolites. Computer simulation of metabolism. Precursor identification. Cycles of nitrogen, sulfur, and phosphorus in nature; key enzymes. 2. Non-proteinogenic amino acids, their occurrence and biological role. Derivatives and homologs of common amino acids. Opines. Lathyrogens. Unusual aromatic, heterocyclic, and sulfur-containing amino acids. Taurine. Betaines. Biogenic amines, their biosynthesis, degradation, and the enzymes involved. Aminoaldehydes. Physiological functions of amines and polyamines. Protoalkaloids. 3. Biologically active peptides. Peptide hormones and peptides affecting blood pressure. Peptide toxins of insects and microorganisms. Peptide antibiotics, classification and mode of action. Biosynthesis by multienzyme systems and novel methods of chemical synthesis. 4. Alkaloids. Occurrence and characteristics. Methods of alkaloid isolation and study. Alkaloidogenic reactions. Biosynthesis and classification of alkaloids. Overview of individual alkaloid groups. Uses of alkaloids in medicine and physiology. Natural hallucinogens. Psychotropic substances of mushrooms, ergot, cacti, poppy, coca leaves, and Indian hemp. 5. Biosynthesis of aromatic compounds. The shikimate pathway and its metabolites. Metabolic networks of cinnamic acids. Metabolites of the polyketide (acetogenin) pathway. Combination of the shikimate and polyketide pathways. Polyketide antibiotics. Polyacetylenes and their bactericidal and fungicidal properties. Furanocoumarins. 6. Glycosides. Characteristics and isolation. Sugar components and aglycones. Cyanogenic glycosides, glucosinolates, phenolic and coumarin glycosides. Natural pigments. Flavonoids. Anthocyanins and catechins. Naphthoquinone and anthraquinone pigments. Betalains. Indigoid and carotenoid pigments. 7. Terpenoids. The mevalonate pathway. Biosynthesis of acyclic and cyclic representatives of various terpene groups. Essential oils and resin acids. Pyrethrins, azulenes, gibberellins. Steroids. Phytosterols and zoosterols. Cardiac steroids. Steroidal saponins. Steroidal alkaloids. Polyterpenes. 8. Natural substances in medicine. Antihypercholesterolemic agents. Treatment of malaria. Stimulant substances of medicinal plants. Constituents of ginkgo, ginseng, schisandra, echinacea, milk thistle, and others. Carcinogens and antineoplastic agents. Aflatoxins, safrole, capsaicin, carcinogenic fungal metabolites. Natural cytostatics. Bioluminescent substances, luciferins. 9. Flavor and fragrance compounds, receptors involved in perception. Relationship between chemical structure and odor, detection limits, the Maillard reaction. Natural and artificial sweeteners. Bitter compounds. Chemical communication in insects. Sex, marking, alarm, and aggregation pheromones. Allomones. Mechanisms of biochemical defense in plants. Phytoalexins (isoflavonoids, terpenoids). 10. Foreign substances (xenobiotics). Xenobiochemistry and pharmacology. Toxicology. Natural toxic substances. Pesticides. Xenobiotics in food. Naturally occurring toxic food constituents. Contamination during storage and processing. Products of food degradation by microorganisms. Food additives. Preservatives. Substances modifying appearance, properties, aroma, and taste. Fate of xenobiotics in the organism. Main pathways of distribution and biotransformation.
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Learning activities and teaching methods
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Lecture
- Attendace
- 26 hours per semester
- Preparation for the Exam
- 50 hours per semester
- Semestral Work
- 10 hours per semester
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Learning outcomes
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Students become familiar with the principles of secondary metabolism, basic methods of studying natural substances, and gain an overview of natural peptides, alkaloids, dyes, terpenoids, etc.
163 Students will gain knowledge of the biochemistry of natural substances such as alkaloids and terpenoids and will become familiar with the basic principles of secondary metabolism and its regulation.
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Prerequisites
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To understand the material, advanced orientation in the topics taught in the KBC/BCH Fundamentals of Biochemistry course is necessary.
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Assessment methods and criteria
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Written exam, Seminar Work
Students must submit a short seminar paper on a chosen topic (AI use is allowed) and master the taught content of the subject in the exam. There are 8 questions to be answered within a period of 1 hour; 24 points is a maximum. Evaluation: 24 - 22 p. A (1) 21 - 19 p. B (1-2) 18 - 16 p. C (2) 15 - 14 p. D (2-3) 13 - 12 p. E (3)
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Recommended literature
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Carocho, M.; Heleno, S.A.; Barros, L.; Eds. (2023). Natural Secondary Metabolites: From Nature, Through Science, to Industry.
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Crozier, A., Clifford, M. N., Ashihara, H. (Eds.). (2006). Plant secondary metabolites, Occurrence, Structure and Role in the Human Diet. Oxford.
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Fattorusso, E. and Taglialatela-Scafati, O. (Eds.). (2008). Modern Alkaloids. Structure, Isolation, Synthesis and Biology. Weinheim.
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Fett-Neto, A.G. (Ed.). (2022). Plant secondary metabolism engineering : methods and protocols. New York.
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Heldt, H.W. (2005). Plant Biochemistry. Burlington.
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Hesse, M. (2002). Alkaloids. Nature's Curse or Blessing. Weinheim.
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Ioannides, C. (Ed.). (2002). Enzyme Systems that Metabolise Drugs and Other Xenobiotics. Chichester.
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Lagana, P. et al. (2017). Chemistry and Hygiene of Food Additives. Cham.
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Macholán, L. (1998). Sekundární metabolity. Brno.
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Mann, J. (2001). Secondary Metabolism. New York.
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Seigler, D.S. (2002). Plant Secondary Metabolism. Norwell, MA, USA.
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Verpoorte, R., Alfermann, A.W. (Eds.). (2000). Metabolic Engineering of Plant Secondary Metabolism. Doordrecht.
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Vodrážka, Z. (1993). Biochemie 3. Praha.
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