KBC/SMEX Secondary Metabolites and Xenobiochemistry

Lecturer: Marek Šebela
Lecture: 2 hours/week
Credits: 4
Winter semester
Form of course completion: exam

Introduction. Elucidation of terminology: primary and secondary metabolism. Methods for the study of secondary metabolism. Methods of analysis of amino acids and betaines. Isolation and use of secondary metabolites. Computer simulation of metabolism. Utilization of nitrogen by plants. Nitrate uptake and assimilation, its reduction to ammonium ions. Nitrate reductase and nitrite reductase. Production of ammonia (ammonium ions). Major metabolic routes for the assimilation of ammonia and redistribution of nitrogen in amino acids. Utilization of sulphur by plants. Sulphate uptake and assimilation. Biosynthesis of cysteine and methionine. Significance of S-adenosylmethionine: biosynthesis and function of ethylene. Nonproteinogenous amino acids. Naturally occurring derivatives and homologs of common amino acids. Opines. Lathyrogens. Anomalous aromatic, heterocyclic and sulphur-containing amino acids. Betaines. Physiological functions and metabolism of quarternary amines and tertiary sulfonium compounds. Betaine aldehyde dehydrogenase and its properties. Biogenic amines. Classification of amines (mono-, di- a polyamines). Biosynthesis of putrescine, cadaverine, agmatine, spermidine and spermine. Reactions of aminotransferases. Reactions of Cu-amine oxidases and FAD-polyamine oxidases. Polyamine conjugates with cinnamic acids. Aminoaldehydes and reaction of aminoaldehyde dehydrogenase. Study of polyamine metabolism. Physiological functions of amines and polyamines. Biologically active peptides. Peptide toxins. Peptide antibiotics. Biosynthesis via multienzyme systems and new approaches of chemical synthesis. Alkaloids. Occurence and properties. Methods for the isolation and study of alkaloids. Biosynthesis and classification of alkaloids. An overview of individual alkaloid groups. Application of alkaloids in medicine (including alternative health practices) and physiology. Natural halucinogens. Psychotropic compounds in mushrooms, ergot, cacti, poppy, coca leaves and Indian hemp. Biosynthesis of aromatic compounds. Metabolic routes of biosynthesis of histidine, phenylalanine, tyrosine and tryptophan. Shikimic acid pathway and its metabolites. Metabolic networks of cinnamic acids. Metabolites of polyketide (acetogenin) pathway. Combinations of the shikimic acid and polyketide pathways. Polyketide antibiotics. Polyacetylens. Biosynthesis of amino acids with branched carbon chain. Glycosides. Characterization and isolation. Sugar moieties and aglycons. Cyanogenic glycosides, glucosinolates, phenolic and coumaric glycosides. Natural dyes. Flavonoids. Anthocyans and catechins. Naphthoquinone and anthraquinone dyes. Indigoic and carotenoic dyes. Terpenoids. Terpenes and terpenic alkaloids. Biosynthesis of acyclic and cyclic representatives of various groups of terpenes. Pyrethrins, azulenes, gibberelins. Steroids. Phytosterols and zoosterols. Steroid cardiacs. Steroid saponins. Steroid alkaloids. Sapogenins of oleanic and ursane type. Flavourings and odorants. Natural and artificial sweeteners. Bitter compounds. Relationship between chemical structure and odor of compounds, limits of detection, Maillard´s reaction. Chemical communication of animals. Sexual, marking, alarm and aggregation pheromones. Lucipherins, kairomones and antifídants. Chemistry of active and passive defense in nature. Allomones, insect pigments (pteridins, ommochromes, melanins). Phytoalexins (isoflavonoids, terpenoids). Lignin, suberin and callose. Lectins. Natural compounds in medicine. Medicaments, stimulants and narcotics. Stimulation compounds from medicinal plants. Tea and coffee. Cancerogenes and antineoplasic compounds. Mechanism of the effect of antibiotics. Biochemistry of exogenous compounds. Exogenous compounds (xenobiotics). Xenobiochemistry and pharmacology. Toxicology. Natural toxic compounds. Pesticides. Exogenous compounds in food. Natural toxic components of food. Contamination during storage and processing. Products of microbial degradation of food.