MASARYKOVA UNIVERZITA Pedagogická fakulta Katedra fyziky, chemie a odborného vzdělávání Introduction to Alkaloids Bakalářská práce Brno 2017 Vedoucí práce: Autor práce: Mgr. Jiří Šibor, Ph.D. Aleš Bárta Prohlášení: „Prohlašuji, že jsem bakalářskou práci vypracoval samostatně, s využitím pouze citovaných pramenů, dalších informací a zdrojů v souladu s Disciplinárním řádem pro studenty Pedagogické fakulty Masarykovy univerzity a se zákonem č. 121/2000 Sb., o právu autorském, o právech souvisejících s právem autorským a o změně některých zákonů (autorský zákon), ve znění pozdějších předpisů.“ V Brně dne: 28.3.2017 ………………….. Aleš Bárta 2 Acknowledgement: I would like to thank to Mgr. Jiří Šibor, Ph.D. not only for the help he provided me with but also for his endless patience during our sessions which helped me complete this bachelor thesis. 3 Obsah INTRODUCTION AND GOALS .............................................................................................. 6 WORKING APPROACH .......................................................................................................... 7 1 ALKALOIDS – CHARACTERISTICS ................................................................................. 8 1.1 HISTORY OF ALKALOID CHEMISTRY ................................................................................ 11 1.2 SIGNIFICANCE OF ALKALOID FORMATION FOR THE PRODUCER ORGANISM .................... 11 1.3 APPLICATIONS ................................................................................................................... 11 2 PHENYLETHYLAMINE DERIVATIVES ........................................................................ 13 2.1 MESCALINE ....................................................................................................................... 13 2.2 EPHEDRINE AND NORPSEUDOEPHEDRINE ......................................................................... 14 3 PYRIDINE AND PIPERIDINE DERIVATIVES ............................................................... 16 3.1 NICOTINE .......................................................................................................................... 16 3.1.1 NICOTINE ISOLATION ..................................................................................................... 17 3.2 CONIINE ............................................................................................................................ 18 4 PYRROLIDINE DERIVATIVES ........................................................................................ 20 4.1 HYGRINE ........................................................................................................................... 20 4.2 CUSCOHYGRINE ................................................................................................................ 21 5 TROPANE DERIVATIVES ................................................................................................. 22 5.1 ATROPINE GROUP .......................................................................................................... 23 5.1.1 ATROPINE ....................................................................................................................... 23 5.1.2 HYOSCYAMINE ............................................................................................................... 24 5.1.3 SCOPOLAMINE ................................................................................................................ 25 5.2 PSEUDOTROPINE GROUP ............................................................................................. 25 5.2.1 ECGONINE ...................................................................................................................... 26 5.2.2 PSEUDOECGONINE .......................................................................................................... 26 5.2.3 COCAINE ........................................................................................................................ 27 6 INDOLE DERIVATVES ....................................................................................................... 29 6.1 SIMPLE-STRUCTURED COMPOUNDS .................................................................................. 29 6.1.1 GRAMINE ........................................................................................................................ 29 6.1.2 BUFOTENINE .................................................................................................................. 30 6.1.3 PSILOCYBINE .................................................................................................................. 31 6.2 COMPLEX-STRUCTURED COMPOUNDS .............................................................................. 33 6.2.1 YOHIMBINE .................................................................................................................... 33 6.2.2 PHYSOSTIGMINE ............................................................................................................. 33 6.2.3 RESERPINE ..................................................................................................................... 34 6.2.4 STRYCHNINE .................................................................................................................. 35 6.3 LYSERGIC ACID ................................................................................................................. 36 7 QUINOLINE DERIVATIVES.............................................................................................. 38 7.1 QUININE ............................................................................................................................ 38 7.2 QUNIDINE .......................................................................................................................... 39 8 ISOQUINOLINE DERIVATIVES ....................................................................................... 40 8.1.1 PAPAVERINE ................................................................................................................... 41 8.1.2 LAUDANOSINE ............................................................................................................... 41 8.1.3 HYDRASTINE .................................................................................................................. 42 8.1.4 RETICULINE .................................................................................................................... 43 4 8.2 MORPHINE GROUP ............................................................................................................. 43 8.2.1 MORPHINE ...................................................................................................................... 44 8.2.2 CODEINE......................................................................................................................... 45 8.2.3 THEBAINE ....................................................................................................................... 46 8.3 OTHER ISOQUINOLINE DERIVATIVES................................................................................. 46 8.3.1 BERBERINE ..................................................................................................................... 46 8.3.2 TUBOCURARINE ............................................................................................................. 47 9 PYRROLIZIDINE DERIVATIVES .................................................................................... 48 9.1 MONOCROTALINE ............................................................................................................. 49 10 QUINOLIZIDINE DERIVATIVES ................................................................................... 50 10.1 LUPININE ......................................................................................................................... 50 10.2 EMETINE .......................................................................................................................... 51 10.3 (-)-SPARTEINE ................................................................................................................. 52 11 IMIDAZOLE DERIVATIVES .......................................................................................... 53 11.1 PILOCARPINE ................................................................................................................... 53 11.2 MUSCARINE .................................................................................................................... 54 12 PURINE DERIVATIVES ................................................................................................... 55 12.1 XANTHINE ....................................................................................................................... 55 12.2 THEOPHYLLINE ............................................................................................................... 56 12.3 THEOBROMINE ................................................................................................................ 56 12.4 CAFFEINE ........................................................................................................................ 58 12.5 CAFFEINE MICROSUBLUMATION ..................................................................................... 60 13 STEROIDAL ALKALOIDS ............................................................................................... 61 13.1 SOLANIDINE ...................................................................................................................