Manual phytochemistry alkaloids

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Text of Manual phytochemistry alkaloids

  • 2010

    Al Azhar University Faculty of Pharmacy Department of Pharmacognosy

    Dr. Mazen A. El-Sakka

    PHYTOCHEMISTRY (3) ALKALOIDS

    Third Edition 2010

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    Contents Generalities of Alkaloids ...................................................................................... 7

    Definition ................................................................................................................... 7

    Classification ............................................................................................................ 8

    Distribution ............................................................................................................... 8

    Functions of alkaloids in plants ......................................................................... 9

    Nomenclature........................................................................................................... 9

    Prefixes and suffixes: .......................................................................................... 10

    Basicity ..................................................................................................................... 10

    Factors that may influence the degree of basicity .......................... 10

    Physical properties ............................................................................................... 12

    Chemical Properties ............................................................................................. 13

    Extraction, purification and separation ........................................................ 18

    Selection of alkalis ............................................................................................... 19

    Selection of solvents ........................................................................................... 20

    Quantitative analysis .......................................................................................... 21

    Pharmacological activity of Alkaloids............................................................ 22

    ALKALOIDS DERIVED FROM ORNITHINE .................................................... 23

    Structure of Tropane Alkaloids ................................................................... 23

    Pyrrolidine and Tropane Alkaloids ............................................................. 25

    Characterization of alkaloids containing tropane alkaloids .............. 29

    Official Solanaceae Containing Tropane Alkaloids ................................... 29

    Atropa belladonma ....................................................................................... 29

    Drugs in Pharmacy .......................................................................................... 32

    Hyoscyamus niger ........................................................................................ 33

    Solanaceae that are Industrial Sources of Tropane Alkaloids ............ 34

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    Hyoscyamus muticus .................................................................................. 34

    Datura metel .................................................................................................. 34

    Datura stramonium ..................................................................................... 34

    ALKALOIDS CONTAINING ERYTHROXYLACEAE ........................................ 36

    Erythroxylum coca ....................................................................................... 36

    History .................................................................................................................. 36

    Addiction terms ................................................................................................. 37

    Conversion to Crack .................................................................................... 41

    Pyrrolizidine alkaloids ......................................................................................... 42

    Drugs Containing Pyrrolizidine alkaloids ..................................................... 44

    Borago officinalis .......................................................................................... 44

    Symphytum officinalis ................................................................................ 45

    Tussilago farfara ........................................................................................... 46

    Quinolizidine Alkaloids ........................................................................................ 47

    Lupinus spp. .................................................................................................... 47

    ALKALOIDS DERIVED FROM LYSINE ............................................................ 48

    Lobelia inflate ................................................................................................ 49

    Biosynthesis of Lobeline ................................................................................ 49

    Punica granatum........................................................................................... 50

    Piperidine Amides :Piperaceae ......................................................................... 52

    Piper nigrum ................................................................................................... 52

    Alkaloids Derived from Nicotinic Acid ........................................................... 53

    PYRIDINE ALKALOIDS .................................................................................... 53

    Biosynthesis of Nicotinic acid ...................................................................... 54

    Vitamin B3 ...................................................................................................... 55

    Tobacco ............................................................................................................ 56

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    Facts about Nicotine ........................................................................................ 57

    ALKALOIDS DERIVED FROM PHENYALANINE & TYROSINE ................. 58

    Phenylethylamines and Simple Tetrahydroisoquinoline Alkaloids 58

    Simple Tetrahydroisoquinolines ..................................................................... 69

    Lophophora williamsii ................................................................................. 69

    Benzyltetrahydroisoqunolines ......................................................................... 70

    Biosynthesis........................................................................................................ 70

    Modified Benzyltetrahydroisoquinoline Alkaloids ..................................... 71

    Papaver somniferum ................................................................................... 73

    Opiates/Opioids Chemistry & Mechanism of Action ................................ 77

    Antidote ................................................................................................................ 80

    Chelidonium majus ...................................................................................... 82

    Isolation of Opium Ingredients ....................................................................... 84

    Isoquinoline Alkaloids (Phenethylisoquinolines) ...................................... 85

    Colchicum autumnale ................................................................................. 85

    Terpenoid Tetrahydroisoquinoline Alkaloids .............................................. 86

    Amaryllidaceae Alkaloids ................................................................................... 87

    ALKALOIDS DERIVED FROM TRYPTOPHAN ................................................ 88

    Simple Indole Alkaloids ...................................................................................... 89

    Hordeum vulgare .......................................................................................... 89

    Simple -Carboline Alkaloids ........................................................................... 90

    Peganum harmala ........................................................................................ 90

    Terpenoid Indole Alkaloids ............................................................................... 92

    Rauwolfia serpentine................................................................................... 92

    Catharanthus roseus ................................................................................... 95

    Strychnos nux-vomica ................................................................................ 97

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    Quinoline Alkaloids .............................................................................................. 98

    Pyrroloindole Alkaloids ....................................................................................... 99

    Physostigma venenosum ........................................................................... 99

    Ergot Alkaloids .................................................................................................... 102

    Claviceps purpurea ................................................................................... 102

    ALKALOIDS DERIVED FROM ANTHRANILIC ACID ................................ 106

    Quinazoline Alkaloids ....................................................................................... 106

    Quinoline and Acridine Alkaloids ................................................................. 106

    ALKALOIDS D