Index

Abietic acid 156 Adenylate cyclase 193,194, 197 Acetaldehyde 87, 116 Adenylosuccinate lyase 200 Acetate 36-38,40,43,48,60,61, 72, Adhota vasica 141 117,125,138,141,146,150,158, Adrenaline 190, 197 161, 189 Adrenergic system 185, 189-192 Acetoacetic acid 14, 35-37,60,61 Agglutination 202 Acetonedicarboxylic acid 13, 35, 60 Agmatine 21, 22 Acetylcholine (see Choline, acetyl) coumaroyl- 23 Acids 3, 28, 167 Agonists 186 Aconite 156 Agroclavine 128,129,131,172 Aconitine 156, 157 Aizoaceae 108 Aconitum 155, 157 Ajmalicine 121-123 Acridine 1 37, 139 Ajmaline 114, 117, 119, 121-123, 198 Acridone 139, 140 Alanine 20, 38, 49 Actinidia polygama 154 f3-Alanine 49 Actinidine 154, 155 Alcohol dehydrogenase 198 Addiction 194 Alcoholism 87 Adenine 147 Aldehydes 13,21,23,76,115,167, Adenocarpine 47 169 Adenocarpus Aldol condensation 12 foliosus 37, 47 Alfalfa 28 viscosus 47 Allantoic acid 148 Adenosine 193,195 Allantoin 148 monophosphate, cyclic 193, 195, Alpiniginine 86 197 Amanita 23, 25 triphosphate 197 Amaranthin 150 S-Adenosylmethionine 15,40, 106, Amaranthus 150 148 Amaryllidaceae 105 212 Index

Amides 23,26,28,40,167,174 100 Amidines 22 Arthrobacter 173 Amine oxidase 14, 60, 78, 189, 191 colchovorum 176 Amines 20, 167, 191 oxtdans 174, 175 Amino acids 12,15,20,45,46,69,73, Arthropods 3 149, 167, 196 Arundo donax 30 a-Aminoadipic acid 50 Ascorbic acid 198 2-Aminobenzoylacetic acid 138, 141 Aspartic acid 43, 48-50, 141 'Y-Aminobutyric acid 69, 194, 195 imino- 49 2-Amino-3-methylenepentanoic acid Aspergillus 146 fumigatus 131 3-Aminomethylindole 30 ochraceus 1 77 5-Aminopentanal 37, 70 versicolor 175 Ammodendron karelinii 72 Asptdosperma 11 3, 125, 126 Ammonia 7, 38 pyricollum 127 Ammonium 161 Aspidospermine 120, 127 Ammothamnus lehmannii 71 Astrocaria phyllantoides 47 a-Amylase 202 Astrocasine 47 Anabasine 17,18,42,43,46,47,70, Atisine 156, 157 169 ATPase 196, 198 Anagyrine 72, 73 Atropa 5,58 Analogy 4 belladonna 58, 62, 64 Anatabine 43,46 Atropine (see Hyoscyamine) Androcymbine 109 Autumnaline 110, 111 Androcymbium methanthiodes 109 Auxins 7,48, 115, 123, 161 Angustifoline 67, 72 Azaquinones 174 Anhalamine 77 Anhalonidine 77 Anhalonium lewinti" 25 Bacteria 3, 8, 49, 50, 141, 174, 200 Animals 3,30,51, 162, 166, 194 halophilic 198 Annona squamosa 79 Banana 25, 26 Annuloline 26, 110, 111 Baptifoline 68 Antagonists 186 Baptista 67, 72 Anthranilic acid 131,137,142,145, Barley 23, 25, 30 156 Batrachotoxinin A 162, 196 Aphids 69 Beans 17,38,115 Apocynaceae 3, 113, 11 7, 123, 125, Beets 23, 149 158 sugar 21 Apomorphine 191 Belladine 106, 107 Aporphines 91, 100, 170 Benzoic acid 63 127 m-hydroxy- 63 Arabinoside 40 Benzophenanthridines 83, 198,200 Arborine 141 Benzoxazoles 148 Areca catechu 68 Benzoxazolinone 148, 149 Arecaidine 168, 169 6-methoxy- 148 -N-oxide 168 2, 77,92, 176 Arecoline 168,187,195 bis- 79, 176 Argemone 99 Berberastine 79, 82 Arginine 21, 22, 62, 69, 161 Berberine 2,3,78,81,82,177, Aristolochia sipho 100 197-200 Index 213

Berbine 170 Carbostyrils 169, 171 Beta vulgaris 23 Carcinogens 168, 199 Betacyanidin 149, 150 Carica papaya 39 Betacyanins 149 Carotenoids 198 Betaine 23, 24, 28, 46 Carpaine 39 Betalains 149 Casimiroa edulis 15 1 Betalamic acid 149, 150 Casimiroine 138 Betaxanthins 149 Cassaine 196 Betel nut 168 Cassia speetabilis 39 Betonicine 28 Castor bean 40 195 Catecholamines 87,194,197 Biosynthesis 12 Catechol-O-methyltransferase 189, Boldine 92 202 Boraginaceae 144 Catha edulis 40 Bound forms 6, 47, 98 Catharanthine 120, 123, 126,202 Brain 115, 169, 192-195 Catharanthus 11 3, 123 Brownine 156 roseus 6,7,121-123 Bryophytes 3 Catheduline 40 Bryozoans 3 Cathenamine 119-122 Bufotalin 162 Cations 187,190,195 Bufotenine 29,167,195 Cats 168, 171 Bulbocapnine 92 Ceanothine B 24 Butterflies 67, 147, 172 Ceanothus 24 Buxus 158, 159, 162 Cell culture 7,25,48,64,101, 115, 121,123 Cellulose 202 Cacti 25, 76 Cephaeline 85, 86 Cadaverine 14, 17, 21, 22, 36, 37, 46, Cephalotaxine A 87 69, 70, 72, 145 Cephalotaxus 86 Caffeic acid 106 Cerebrosides 193 Caffeine 3, 147, 148, 172, 176, 195, Ceveratum 159, 161 196, 199, 200, 202 Chanoclavine-I 128, 129, 131 Calcium 7,194, 196, 197 Chelerythrine 82, 84 Calmodulin 194 83, 84 Calycanthine 116 Chelidonium malus 5, 64, 81, 83 Calyeanthus floridus 116 Chimonanthine' 114, 116 Camellia sinensis 148 Chimonanthus fragrans 116 Camptotheea aeuminata 127 p-Chlorophenylalanine 131 Camptothecin 127, 199 Chlorophyll 7,195 Canary grass 29 Chloroplasts 70, 197, 198 Candicine 25, 27 Cholesterol 158,159,161,163,202 Cannabis sativa 23 Choline 23,24,46 Capsaicinoids 28 acetyl- 23, 24, 185-189 Caracurine-VII 124-126 phosphoryl- 23, 24 Caranine 106 Cholinergic system 185, 197 N-Carbamylputrescine 22 Cholinesterase 186, 188 Carbinolamine 13 Cieer arietinum 23 p-Carboline 115 Cinchona 123, 124, 169, 198 Carbon dioxide 18, 42, 45, 46, 72,92, sueeiruba 124 93,95,98,167 Cinchona mine 124 214 Index

Cinchonidine 169, 171 Crotolaria spectabitis 144 Cinchonine 169, 171 Croton 94 Cinnamic acid 37,47, 106, 109, 110, /lavens 100 138 linearis 94, 100 hydroxy- 28, 106 sparsifolius 94 Citric acid 13, 60, 197 Crotonosine 94, 100 Claviceps 113,127 Cryptolepsis buchanani 40 purpurea 4, 131 82 Clavicipitic acid 128 Cularines 87 Clavines 127,131 Cultures 5, 7, 18,48, 64, 80, 87, 95, Clinia miniata 198 101, 115, 123, 130, 138, 148, 158, Cocaine 59-61, 63, 168, 188, 191, 160,194,200 196, 198 Cunninghamella blakesleeana 176 Cochlearin 63 Curare 123, 125, 187 Coclaurine 77, 80, 92, 94, 95 Cuscohygrine 35, 36 N-methyl- 80, 92 Cyanide 49 95,96,98, 100, 101, 167, fj-Cyanoalanine 49 171,177 3-Cyano-4-methoxypyridine 42 -methyl ether 95 Cycloartenol 162 95, 96, 100, 101 Cyclohexadienone 93,95 14-hydroxy- 176 Cycloheximide 48, 194, 200 Coffea arabica 148 Cyclomicrophyllin A 162 Coffee 148 Cyclopeptine 139 Colchiceine 198, 199, 202 Cyphomandra 60 Colchicine 1, 109, 110, 176, 200, 201 Cytisine 67-69, 72, 73 Colchicum 109 N-methyl- 72, 73 autumnale 110 Cytisus 67 Compositae 138, 144 laburnum 73 Conarrhimine 163 Cytochrome 167, 198 Conessine 177 Cytokinesis 202 Conhydrine 38, 39 Cytokinins 148, 161 'Y-Coniceine 38 Coniine 2, 38 Conium maculatum 38 Darnascenine 137 Conjugation 167 Daphniphyllum teijsmanni 158 Consolida 155 Datura 5, 6, 58, 62 Convolvulaceae 127 ceratocaula 62 Corn 148 ferox 62 Cornaceae 155 innoxia 60, 62, 64 Corydaline 82 metel 60, 63, 64 Corydalis ochotensis 87 meteloides 62 Corynantheidine 172 stramonium 60, 62-64 Corynantheine 117,119,124,125 Decarboxylases 20,25,28,30,37,69, Corynoxeine 125 128, 1)1 Cotinine 169, 170 Degradation 4, 8, 30, 42, 46, 48, 98 -methonium ion 170 1,2-Dehydroanabasine 46 p-Coumaric acid 74· Dehydrolupanine 73 Cournaroylagmatine 23 Dehydrosparteine 73 Crataegus monogyna 20 Delpheline 156, 157 Crinamine 106, 107 Delphinium 1) 5, 1) 8 Crinine 108 ajacis 1 5 6 Index 215

brownii 156 3,5-Dimethoxy-4-hydroxyphenethyl- elatum 156 amine 26,77 Demecolcine 110 Dimethylallyl pyrophosphate 22, 128 Demethoxyalstonidine 16 Dimethylallyltryptophan 128, 131 Demethylation 5,25,42,44,94,98, Dimethylamine 168 100,167-169,171-174,176 3-Dimethylaminomethylindole (see Demethylcotinine 169, 170 Gramine) Dendrobine 155 L- 3-Dimethylamino-3-phenylpropanoic Dendrobium nobile 155 acid 156 21-Deoxyajmaline 123 Dimethylbenzanthracene 199 Deoxyribonucleic acid 199, 200 6,8-Dimethylergoline 127 -polymerase 199, 200 N-Dimethyltryptamine 29 Desacetylisoipecoside 85 Dioscorea hispida 40 Detoxication 8, 73 Dioscorine 40 Diaboline 125, 126 Dipterin 29 Diamine oxidase 14,23,35,37,44, Diterpenoids 155, 196 46,69, 70, 167, 198 Dogs 167, 171, 173 Diamines 14 Dolichothele sphaerica 150 1,4-Diaminobutane (see Putrescine) Dolichotheline 150,151 1,5-Diaminopentane (see Cadaverine) 25-27, 76, 78, 81, 82, 85, 1,5-Diaminopimelic a,cid 50 87,88,92, 191, 193, 194 Dibenzazonine 98 Dropsy 196 Dibenzocyclooctane 99 Duboisia 58, 64 Dibenzopyrrocolines 87 myoporoides 4 Dicentra spectabilis 81 2,4-Dichlorophenoxyacetic acid 48, 123 Echinops ritro 138 Dicotyledons 3, 23 Echinorine 138 Dictamnine 140 Echitamine 122 Dictamnus albus 139 Ecology 5, 8, 68, 161 Dideoxynorlaudanosolinecarboxylic Edulinine 139, 140 acid 87 Ellipticine 172, 176, 198, 199 Dienol-benzene rearrangement 94 9-hydroxy- 176, 198 Digitoxin 196 9-methoxy- 176 Dihydroxyacetone phosphate 21,49 Elymoclavine 128, 129, 131, 172 2,6-Dihydroxy-N-methylmyosmine Embryos 7, 23, 25 175 Emetine 85, 86, 198, 200 2,3-DihydroxY-3-methylpentanoic acid Endorphins 192 146 Enkephalins 192-194 3,4-Dihydroxyphenethylamine (see Enzymes 16, 18, 20, 25, 64, 73, 74, Dopamine) 106,121,138, 148, 160, 164, 3,4-Dihydroxyphenylacetaldehyde 87 173-175,182,183,186, 194, 197 3,4-Dihydroxyphenylacetic acid 25, Ephedra gerardiana 27 87 Ephedrine 27,168,191 3,4-Dihydroxyphenylalanine 25-27, Epistephanine 80 76,78,79,88,97,101,149 Equisetum 3 3,4-Dihydroxyphenylpyruvic acid 78 Ergocornine 200 2,6-Dihydroxypseudooxynicotine 175 Ergocristine 4 3,4-Dihydroxypyridine 38 Ergoline 128 3,4-DimethoxY-5-hydroxymethyl- Ergometrine 130 26, 76 Ergonovine 130 216 Index

Ergot 4, 113, 127, 191, 195 Galanthamine 107, 189 Ergotamine 4, 130 Galanthine 106, 107 Erysopine 99 Galega officinalis 22 Erythraline 99 Galegine 22 Erythratine 99 Ganglia 185, 187 Erythrina 99, 187 Gangliosides 185, 195, 202 Erythrinans 99 Garrya 1)5, 156 Erythroxylum 6, 58, 59 Garryine 157 coca 35,59 Geissoschizine 119-121, 123, 125 Escherichia coli 174 Gelsemine 121, 125 Eschscholtzia 99 Genetics 4,5, 17,43,68,72,100,160, Eschscholtzidine 99 195 Eserine (see Physostigmine) Genista 67 Esters 58, 156, 168 aetnensis 68, 73 Ethanol 87, 115 Gentianine 155 Ethanolamine 20,24, 156 Geography 3 Ethylamine 20 Geraniol 85,117,118,122,124 Etiolation 7 10-hydroxy- 122 Euphorbiaceae 16,41,42, 117 Germination 196 Evodia rutaecarpa 142 Gibberellins 7,48, 64, 158, 202 Evolution 8, 16 Glaucoma 196 Evoxine 140 Glaucopsyche Iygdamus 67 Gleditsia triacanthos 148 Glochidicine 1)1 Fagales 3 Glochidion philippicum 15 1 Fagara 96 Glucose 197 y-Fagarine 140 Glucosides 38,40,85, 118, 119, 127, Ferns 3 139,149,161, 176 Fish 3 p-Glucuronides 167-169, 171, 172 Flavinantine 100 Glutamic acid 23, 43, 46, 60, 69, 150, Flavines 123, 168 195 Flavinine 100 Glyceraldehyde 49 Floramultine 111 -3-phosphate 49,50 Flowering 6, 7,20, 23,47,63,64, 123 Glycerol 43, 48-50 5-Fluorotryptophan 131 Glycine 13, 21, 23, 24, 30, 60, 148, Formaldehyde 23, 169, 172 1)6, 193, 195 Formate 27,41,48,81, 142 Glycogen 197 Formylkynurenine 51 Glycolic acid 46 Frangulanine 196 Glycolysis 197 Free radicals 15 Glycoproteins 194 Frog 162 Glycosomia arborea 141 Fumaric acid 175 Glyoxylate cycle 48 Fungi 3,8,21,23,29,50,51,113,127, Glyoxylic acid 176 129, 148, 161, 162, 176, 177 Goebel/ia pachycarpa 69, 73 Funtumia 1)8, 159 Grafting 5, 6, 62, 68, 131, 138 Funtumidine 177 Graminae 148 Funtumine 177 Gramine 30 Furans 139 Grantianic acid 145 Furoquinolines 139 Graveoline 138 Index 217

Growth factors 7, 23, 30,48, 63, 64, Horses 173 101, 123, 160 Horsetails 3 Guanine 147 Humans 87, 115, 167-172 Guanosine triphosphate 201 Hyaluronic acid 188 Guinea pig 168 Hydrastine 81, 82 Guvacine 195 Hydrastis canadensis 81 Gymnosperms 3,23 a-Hydroxyalanine 130 a-Hydroxyaminobutyric acid 130 3-Hydroxyanthranilic acid 51, 138, Haemanthamine 106-109 148 Haemanthidine 109 Hydroxycinnamic acids 28, 106 Hallucinogens 4, 29, 116, 168, 195 Hydroxylation 20,25,27, 122, 128- Halosaline 37 131,159,166,168,169,172,173, Haloxylon salicornicum 37 175-177, 198 Harmala 192 Hydroxylupanine 71, 72, 176 Harmaline 115, 116, 172, 192, 196- 4-Hydroxylysine 37, 69 198 6-Hydroxy-N-methylmyosmine 175 8-hydroxy- 115 p-Hydroxyphenethanolamine (see Harman 115,116,195 Octopamine) Harmine 115, 116, 195 p-Hydroxyphenylacetaldehyde 168 Hedera helix 84 4-Hydroxyphenylpyruvic acid 92 Heimia salicifolia 73 5-Hydroxypipecolic acid 37, 38 Heliotridine-N-oxide 145 3P-Hydroxy-5a-pregn-16-en-20-one Heliotrine 197 160 Helminthosporium sacchari 21 Hydroxyproline 28, 60 Hemicholinium 186 6-Hydroxypseudooxynicotine 175 Hemiterpenoids 154 4-Hydroxytryptamine 29 Herbivores 8 5-Hydroxytryptamine (see Serotonin) Hernandia nymphaefolia 42 a-Hydroxyvaline 130 (see , diacetyl) Hygric acid 28 Heteroxanthine 147, 148 Hygrine 35, 36, 60 Histamine 3, 30, 31, 150, 151, 168, Hyoscine (see Scopolamine) 202 Hyoscyamine 4, 58-64, 168, 174, 188 Histidine 30,31,69, 131, 150, 189 4,7-dehydro- 62 Holamine 161 6-hydroxy- 62, 64 Holaphyllarnine 161, 163 -N-oxide 62 Holaphylline 161, 163 Hyoscyamus 58 Holarrhena 158, 159, 161 floribunda 161, 162 Iboga 125, 126 Holarrhimine 163 114,120,126 Homaporphines 111 Icajin 125 Homocysteine 40 Imidazole 30, 150, 189 Homolycorine 108, 109 -glycerophosphate 150 Homology 3 Imidazoleacrylic acid 30, 31 Homostachydrine 28 Immunoglobulin 200 Hordatines 22 Indicaxanthin 150 Hordenine 4, 25, 27, 168 Indole 2, 18, 113, 142, 149, 172, 176 Hordeum vulgare 4, 6, 25 Indole-3-acetic acid 8, 28, 30, 64, 114, Hormones 28, 30, 177, 194 123, 167 218 Index

Indolenine 116 Latex 5,97,98 Inocybe 23 Laudanidine 93, 96 Inositides 188 15, 77,96 Insects 69, 161, 169 Laudanosoline 97 Insulin 202 Laurifoline 96, 97 Intestine 171 Leaves 5,6,42,47,62,63,131,138, Ion transport 116, 185, 188, 195-197 141, 156 Ipecacuanha 84, 200 Leguminosae 17,29,67,73,144 Ipomoea violacea 1 31 Lettuce 196 Irediamine A 199 Leucana glauca 37 Iridoids 154 Leucine 20, 21, 130 Iriodial 154 Leurocristine 123 Iron 38 Light 7,47,63, 100, 123, 160, 161 Isrnine 108 Lignin 25 Isoamylamine 20, 21 Liliaceae 109, 158 Isobutylamine 20, 21 Linearisine 101 Isocorydine 79 Lipase 197 Isoleucine 62, 146 Lipids 196 Isonicotinic acid 174 Liriodendron tulipifera 100 Isopenniclavine 129 Lithium 7 Isopentenyl pyrophosphate 128 Litsea glutinosa 79 Isopentylamine 20 Liver 167-172, 199 Isopelletierine 14, 36, 37 Lobelia 37 Isoquinoline 2, 26, 76, 170 37, 188 1-benzyl- 77 Loganiaceae 117, 124 Isosetoclavine 129 Loganic acid 122 Isositsirikine 121 Loganin 117,118,122,124 Isothebaine 91-93, 95 Lolium multiflorum 26, 110 Isovaleric acid 150 Lophocerine 77 Lopbopbora williamsit' 25 Lophophorine 77 Jaconine 145 Lupanine 68,69, 71-73, 175 Jerveratrum 159, 161 hydroxy- 71-73, 175 Julocrotine 24 Lupine 5,7,17,47,67 ] ulocroton montevidensis 24 Lupinine 67,69-72 4-hydroxycinnamoyl- 74 piperidyl- 71 a-Keto-8-aminovaleric acid 64 Lupinus 6, 67 3-Keto-2-methylvaleric acid 62 albus 73 5-Ketooctanal 38 angustifolius 69, 71-73 5-Ketooctylamine 38 arboreus 72 Kinetin 7,25,40 luteus 70-72, 74 Kreysigia multiflora 111 Lycoctonine 156, 157 Kurchi 158, 159 Lycopersicon esculentum 159 glandulosum 7 Laburnum anagyroides 73 pimpinellifolium 159 Laccase 16,97,176 Lycopodium 3, 37 Lactic dehydrogenase 198 Lycorenine 108, 109 Lanosterol 162 Lycorine 3, 106, 107, 198, 200 Lasiocarpine 197, 200 Lyfoline 73 Index 219

Lysergic acid 16,24, 114, 127-131, Methylation 15, 16, 20, 23, 25, 29, 39, 172, 176, 195, 199,200 44, 79, 92, 94, 106, 122, 148, 156, Lysergic aldehyde 129 167,168,170,173 Lysergol 129, 130 3-Methylbutanal 77 Lysine 13,21,22,28, 36, 37,42,46, 2-Methylbutyric acid 62 48, 69, 71, 74, 141 1-Methyl-3-carboxamido-6-pyridone Lythraceae 37, 73 42 3-Methylcholanthrene 173 N-Methylcoclaurine 80,92 Mackinlaya 141 N-Methylconiine 39 Macleaya microcarpa 81 1-Methyl-3-cyano-2-pyridone 42 Macrantaline 91 I-Methyl-3-cyano-4-pyridone 41,42 Magnesium 190,201 1-Methyl-3-cyano-6-pyridone 42 Magnocurarine 77 N-Methylcytisine 72 Magnoflorine 92, 97 Methylenetetrahydrofolic acid 115 Maleamic acid 175 N-Methyl-2-hydroxypyrrolidine 35 Maleic acid 175 N-Methylisopelletierine 37 Malic acid 48, 49 8-N-Methylornithine 44, 60 Mallotus repandus 42 N-Methyl-A I-piperideinium chloride Malonic acid 37,43,48 18 Mammals 87, 115, 166, 169 4-Methylproline 154 Mandragora 58 N-Methylputrescine 35, 36, 44, 60 Manganese 7, 62 N-Methylpyridinium 167 Matridine 73 Methylpyrroline 61, 154, 155 68-71, 73 N-Methyltryptamine 29, 114, 142 -N-oxide 73 N-Methyltyramine 4,25,27 Mavacurin 122 7-Methylxanthine (see Heteroxanthine) Maytansine 202 1-Methylxanthosine 148 92 7-Methylxanthosine 148 Medicago sativa 28 Mevalonic acid 16,131,146,154-156, Membranes 47, 182, 191, 194, 195, 158 197, 202 Mice 168, 169, 173, 194 Menispermaceae 91,92 Microorganisms 8,68, 166, 173, 174, Mescaline 1,25, 167, 191, 195,200, 198 (see also Bacteria, Fungi) 202 Microscopy, electron 5 N-acetyl- 168 Microsomes 167-169,171,172,197, Mesembrine 108 198, 200 Metabolic grid 17, 41 Microtubules 201, 202 Meteloidine 62, 63 cortical 202 Methionine 15,23-27, 30,40,44, 77, Millipedes 3 81, 138, 139, 142, 148, 150, 156 Mimosa pudica 37 5-Methoxy-3,4-dihydroxyphenethyl• Mimoside 38 amine 26 Mimosine 37, 38, 174, 198, 199 3-Methoxy-4-hydroxyphenethylamine Mitochondria 197 26 Mitosis 200-203 Methyl groups 15,20,23,27,40,41, Molluscs 69 46,81 Monkeys 173 Methylamine 14,21,23,60, 170 Monocotyledons 3, 23 y-Methylaminobutyraldehyde 44 Monocrotalic acid 145 3-Methylaminomethylindole 30 Monocrotaline 145 O-Methylandrocymbine 109, 110 Montanine 107 220 Index

Morning glory 4, 131 5'-hydroxy- 170 Morphinandienones 95 6-hydroxy- 173-175 Morphinans 91 -l'-N-oxide 45,46,169,174 Morphine 78, 91, 95-98, 100, 101, Nicotinic acid 8, 39, 40, 42, 46, 48, 50 167,171,177,186,192-194,203 -N-arabinoside 40 diacetyl- 172 esters 40 6-glucuronide 171 N-methyl- (see Trigonelline) N-oxide 172 nucleotide 40, 50, 51 quinone 172 Nicotyrine 43, 170 3-sulfate 171 Nigel/a 137 Mosses 3 damascena 138 Moths 147,172 Nitidine 83 Munitagine 99 Nitrates 7, 45 Muramine 86 Nitrilase 174 Muscarine 23, 24, 187 Nitriles 42, 174 Muscles 186, 187, 196, 202 Nitrophenanthrenes 100 Mushrooms (see Fungi) Nocardia 176 Myosmine 43, 46 Noradrenaline 3,26,27,74,83, 100, 110, 185, 189, 193, 197, 202 Noragroclavine 172 NAD 42,73 Norbelladine 105-108 NADP ,39,121,123,167,171 O-methyl- 107 193 Norepinephrine (see Noradrenaline) Narciclasine 108, 200 Norhygrine 36 Narcissidine 106 Norhyosciamine4 Narcissus tazetta 199 Norlaudanosoline 78, 79, 87, 93, 95, Narcotine 4, 81, 82, 170 96, 170 Necic acids 144, 146 -I-carboxylic acid 78 Necines 144 dimethyl ether 93, 96 Nematodes 8 98, 167 Nerine bowdenii 106 Nornicotine 5,43-45,167,169,170 Nerolidol 156, 157 Noroxomaritidine 108 Nerve gas 188 Norpluviine 106, 107 Nervous system 184, 196 Norprotosinomenine 77,92,99 adrenergic 185, 189-192 Norsinoacutine 100 autonomic 185 Nucleic acids 148, 182, 184, 198-200 central 184 transcription of 182, 199 cholinergic 185-189, 197 Nucleotides 148, 200 Nettle 23, 30 Nuphar lutcum 155 Nicotiana 6, 18, 42 Nupharamine 155 glauca 46, 49 Nupharidine 155 glutinosa 45, 46 Nutrition 7, 130 rustica 43 sylvestris 48 tabacum 46 Ochotensimine 87 Nicotianine 40 Octopamine 26 Nicotinamide 40,41,50 Oligomycin 198 1-methyl- 51 Onions 200,203 Nicotine 2,4, 5,7, 15, 18,42, 167, Ontogeny 5, 6, 63, 68, 69, 73, 97 169,170,173-175,177,186-188, Ophiocarpine 82 191, 198 Opiate receptor 171,192-194 Index 221

Opium 18 Peptides 24, 128, 130, 192, 196, 198 Opuntia ficus-indica 149 Periwinkles 123 Orientaline 92-94 Peroxidase 16, 78, 80, 97, 129 Orientalinol 95 Peyote 25, 26 91 Phalaris 29 Ornithine 13,21,28,36,42,43,45, Pharmacology 182 60-62, 64, 141, 144, 145 Phaseolus 30 decarboxylation of 21,45, 202 vulgaris 95,115 Ouabain 196 Phenanthrene 155 Ourouparia gambir 16 Phenanthroindolizidines 36, 200 Ovules 6,23 Phenanthroquinolizidines 200 Oxidases 128, 174 Phenobarbital 171 diamine 14,23,25, 37,44,46,69, Phenolate radicals 15, 93, 105, 106 70, 167, 198 Phenob 5, 15, 167, 202 monoamine 23, 116, 167, 189, 191 Phenylacetaldehyde 92 Oxidation 16,79,80,95, 128, 166, Phenylalanine 13,25-28,37,62,63, 168, 173 74,106,108-110,130, 139, 141, N-Oxides 2,98, 146, 167, 171 156, 158, 193 Oxindoles 124 -ammonia lyase 200 Oxotremorine 187 Phenylcyclopeptine 24 Oxydemethoxyalstonidine 16 Phenylethylamine 25,27, 191 Oxynitidine 83 Phenylketonuria 87 Oxysanguinarine 16, 83, 84 Phenyllactic acid 63 Phenylpyruvic acid 88 Pheromones 147, 172 P-450 131,172,173,198 Phosphatase 188,197,198 Panda oleosa 24 Phosphate 131 Pandamine 24 Phosphatidylserine 196 Pandanales 3 Phosphodiesterase 197 Panicum miliaceum 25 Phosphoglycerides 193 Papaver 6, 86,91,94 Phospholipids 23, 24 bracteatum 86,91,97,100, 101 Phosphoribosyl pyrophosphate 51 dubium 92 Phosphorylase 197 orientale 91, 92, 95 Photoperiod 7,47,63,100 pseudo-orientale 91 Photophosphorylation 198 somniferum 4,78,79,81,91-93,95, Phthalide-isoquinoline 81 97, 100, 101 Phyllobates aurotaenia 162 Papaveraceae 83,87,91,92 Phyllocladene 156 77,79,170,176,197 Physostigma 6 Parkinsonism 88 venenosum 114 Parsley 40 Physostigmine 114, 186, 188, 189 Passiflora edulis 115 Phytochrome 7 Pavine 100 Picraline 117, 121, 122 Peas 17,23,39,40,46,158,200 Pilocarpine 150,168,187,198 Peganine (see Vasicine) Pilocarpus 150 Peganum harmala 115 Pilocereine 77 Penicillium 139 Pinidine 39 concavo-rugulosum 1 31 Pinus jeffreyit' 39 roquefortit' 1 31, 1 76 Pipecolic acid 28, 37, 69 Penniclavine 128,129,131 Piper nigrum 154 Pepper 28 Piperideine 14,37,46,47,70,71 222 Index

Piperidine 2, 14, 36, 42, 46, 70 2,6-dihydroxy- 38, 174, 175 Pisum sativum 46 nucleotide cycle 41,43,50 Pituitary 194 Pyridones 16,37,41,83,169, 174 Platydesmine 140 Pyridoxal 168, 198 Platynecine 145 Pyrindicin 39 Ploidy 5,48, 64, 123 Pyrone 16 Pluviine 108, 109 Pyrrole 35 Podophyllotoxin 201 Pyrrolidine 2, 14, 35, 42, 59 Pollen 23 ~ I-Pyrroline 14, 44 Polyamines 22 -5-carboxylic acid 44, 64 Polyamine oxidase 23 Pyrrolinium 35, 36 Polyporus anceps 176 N-methyl- 44,45, 60 Polysaccharides 98, 188 Pyrrolizidine 144, 172, 198, 199 Poppy 5, 78, 95 Pyruvic acid 23, 77 Potassium 7,22,193,196 kinase 198 Potatoes 160 Pregnane 158 Pregnenolone 7, 161-163 Quebrachamine 126 Prephenic acid 117 Quinacrine 188, 199 Pretazettine 108 Quinazoline 137, 141 Proapoporphines 94 Quinazolones 3, 141 Procaine 188, 196 Quinidine 170,171,195,198 Progesterone 161, 163 Quinine 124,170,171,196,199,200 Proline 28,60, 130, 150 oxidase 169 4-methyl- 154 Quinoline 2, 137, 164, 198 Propionate 43,48 2,4-dihydroxy- 138-140 Prostaglandins 193, 194 Quinolinic acid 40, 42, 48, 49 Protein 21,131,184,193 Quinolizidine 67, 199 synthesis of 7, 23, 26, 28, 46, 48, Quinuclidine 169 182, 194, 200 Protoalkaloids 20 Protoberberine 81,83,88 Rabbits 168, 169, 172, 173 Protocatechuic aldehyde 106 Races, chemical 4 81,82,86, 101 Ranunculaceae 155 Protosinomenine 81, 93 Rats 87,115,168-172,199,200 Protostephanine 98 Rauwolfia 113, 123 Pseudoconhydrine 39 verticillata 122 Pseudomonas 141, 174 Receptors 183 lupanii 175 glucocorticoid 194 putida 176 muscarinic 187 Pseudo morphine 97 nicotinic 187 Psilocin 195 opiate 192 Psilocybin 29 serotonin 195 Puffer fish 3 Regulation 18, 23, 130, 139 Punicum granatum 37 Reserpine 119, 121, 123, 172, 191, Purine 2, 147, 197 195, 197, 199, 200 Putrescine 14, 21, 36,43-45, 60, 145 77-79, 81-84, 86, 92,93, N-methyl- 35,44,45, 60 95-97,99,101. 170, 176 N-methyl transferase 44 Retronecine 145, 146 Pyrans 139 Rhoeadine 86 Pyridine 2, 8, 39, 168 Ribonuclease 200 Index 223

Ribonucleic acid 148, 199, 200 Sedum polymerase 199 acre 4 Ribose 149, 168 sarmentosum 37 Ribosomes 23, 200 Seeds 6,8,30,47,68,98,131,138, Ricinine 1, 7,40,48, 174 196 Ricininic acid 41 Sempervirine 119, 122, 189 Ricinoleic acid 130 Senecic acid 145 Ricinus communis 7, 40 Senecio 144, 145 Rivea corymbosa 131 douglasit' 146 Roemerine 92, 94 Seneciphyllic acid 145, 146 Roots 5,40,42,44,47,62,123,138, Seneciphylline 146 156, 158, 160, 203 Senescence 6, 42, 63 Roquefortine 131 Serine 21,24, 37, 38,49, 156, 174, Rubiaceae 84,117,123,124 189 Rubidium 196 phosphatidyl- 196 Rubijervine 161 Serinol 21 Ruta Serotonin 29,191,194,195 angustifolia 138 Serpentine 114 graveolens 139 Sesquiterpenoids 40 Rutaecarpine 1, 114, 142 Setoc1avine 128, 129 Rutaceae 40, 96, 138, 139, 142 Sheep 68 Rye 131 Shikimic acid 137, 138 Rye grass 26 Sinoacutine 95, 100 Sino me nine 95 Sinomenium acutum 95 Skimmia japonica 1 39 Salamander 3, 162 Skimmianine 140 Salicales 3 Sky tan thine 154, 155 Salsolinol 87, 170, 198 Skytanthus acutus 154 Salutaridine 91, 95, 96, 176 Snakes 187 95-97 Sodium 196, 197 Salvia officinalis 177 Soladulcine 160 Samandarine 162 Solanidine 159, 161 Sanguinaria canadensis 16 Solanine 176 Sanguinarine 2,5, 16,83, 84, 196 Solanaceae 3, 58, 158, 177 Santiaguine 37,47 Solanum 158, 159, 189 Sarothamnus scoparius 69 aviculare 158 Sarpagine 122 dulcamara 160 Sceletium strictum 117 laciniatum 160 Schiff bases 184 tuberosum 158 Scopolamine 4,58-60,62-64, 188 viarum 160 Scopolia 58 Solasodine 158-160, 177 Scopoline 58 Sophocarpine 73 Scoulerine 81-84 Sophora Secoalkaloids 125, 126 alopecuroides 73 Secologanic acid 122 secundifolia 69 Secologanin 85, 117, 122 tetraptera 69 Securinega suffruticosa 37 Sophoramine 73 Securinine 37 Sophoridine 68, 73 Sedamine 4, 37 Sorbus aucuparia 20 Sedridine 4 Soy bean 23 224 Index

Sparteine 67-73 Tetrahydropapaveroline (see -N-oxide 73 Norlaudanosoline) Spegazzine 198 Tetramethyluric acid 147 Spermidine 22, 23, 200 Tetrodotoxin 196 Spermine 3, 22, 23 91,93,95,96,98,100,101, Sphacelis sorghi 131 176, 177 Spinacea oleracea 30 Theobromine 147,148,173 Spinach 30 Theophylline 147, 148, 172, 196, 197 Squalene 158 Thermopsine 68, 72 Stachydrine 28 Thermopsis rhombi/olia 72 Stephania Thiobinupharidine 155 cepharantha 80 Threonine 69, 146, 150 japonica 80, 98 Tiglic acid 62 Stephanine 100 Tissue culture 6,7,27,48,80,87,95, Steroids 7,16,154,158,176,189, 101,115,123,138, 148, 160 194, 196, 199, 200 Toads 3, 29, 162 Streptomyces Tobacco 5,7,40,42,51,95,174,177 griseoflavus 39 Tomatidenol 160 roseachromogenes 176 Tomatidine 159, 160, 177 Strictosidine 118, 127 Tomatine 7, 158, 160, 176, 197 Strigosine 146 Tomato 158,160 Strychnine 121, 125, 126, 172, 176, Torpedo cali/ornica 188 195 Toxiferine I 123, 125, 126 2-hydroxy-172 Trametes sanguinea 176 -N-oxide 176 Transamination 14,21, 38,64, 70, Strychnos nux-vomica 125 78 Stylopine 81-83, 101 Trewia nudiflora 42 Succinate 43, 48 Triacanthine 147,148 Succindialdehyde 14, 60 Triglycerides 202 Sucrase 198 Trigonelline 39, 40 Sugar cane 21 3,4,5-Trimethoxybenzoic acid 168 Synapse 185, 186 3,4,5-Trimethoxyphenylacetic acid Synaptosomes 192, 197 168 3,4,5-Trimethoxyphenethylamine (see Mescaline) Taxine 156 Trimethyluric acid 148 Taxonomy 3,4, 167 Triterpenoids 158 Taxus 156 Tropane 2, 5, 14, 36, 58, 168, 188 Tazettine 108, 109 Tropic acid 58, 64, 188 Tea 148 Tropine 58, 60, 63, 64 Tembetarine 96, 97 Tropinone 60,63 Terpenoids 16, 39,40,85, 117, 124, 2-carboxyl- 60 127, 154 Tropolones 201,202 Tetrahydroalstonine 121 Trypsin 200 Tetrahydroanabasine 46,47, 70 Tryptamine 29, 30, 114, 115, 118, -dicarboxylic acid 46 123, 125, 167 Tetrahydroberberine 192 N-acetyl- 115 Tetrahydroharman 115 Tryptophan 13,28, 30,50, 51, 114, Tetrahydroisoquinoline 192 116,123,124,127,128,130,138, Tetrahydropalmatine 86 139,142,174,195,198,200 Index 225

Tubocurarine 80, 187, 188, 195, 197, Vincoside 119 198 Vincristine 172 Tubulin 201 Vindoline 7, 114, 119, 123, 126, 176, Turicine 28 202 Tylopbora 36, 111 Vinleurosine 199 asthmatica 111 Viridicatine 139 Tylophorine 111 Viruses 8, 200 Tyramine 25-27,106,110, 191 Viscum album 25 N-methyl- 25, 27 Vitamins 8, 123 -methylpherase 25 Voacanga 126 Tyrosine 13, 25-27, 37, 69, 76, 78, 80, Voacangine 120, 126 81,83, 84,9~97,98, 106, 108-110, 131, 150, 193, 194, 198 Wheat 177 Wieland-Gumlich aldehyde 124 Uleine 127 Worms 3 Urea 148, 176 army- 169 Uric acid 8,147,172,176 Wounding 23, 100 Urine 88, 115 Urocanic acid 30, 31 Urtica 30 Xanthines 147,172,195,197,200, dioica 23 202 Xylem 5

Vacuoles 5, 8,47 Valine 20,21,130 Yeast 50 Vanillylamine 28 Yew 156 Vasicine 141 Yohimbine 117,119,121,122,176, Veratramine 191 191,196 Veratridine 197 Veratrum 158,159, 183, 196 grandiflorum 161 Zapotidine 151 Vesicles 186, 191 Zea mays 148 Vida /aba 71 Zeatin 147, 148 Vinblastine 120, 123, 176, 201, 202 Zizyphin 24 Vinca 123, 200 Zizypbus oenoplia 24 Volume 25 Molecular Biology Advanced Methods in Protein Biochemistry Sequence Determination Editor: S.B.Needleman With contributions by numerous experts and Biophysics 1977.97 figures, 25 tables. XII, 189 pages Editors: A. Kleinzeller, G.F.Springer, ISBN 3-540-08368-5 H. G. Wittmann The determination of protein sequences has become so commonplace that, as more laborato• ries have entered this area of study, the sophisti• cation of the technology has, in fact, progressed to make use of physical properties not previously utilized for this purpose. Earlier manual techni• ques have become automated; current instru• mentation operates at higher parameters and with greater precision than before. Thus the present volume supplements the earlier one in presenting Volume 23: M.Luckner, L.Nover, H.Biihm details 0 the more advanced technologies (optical, Secondary Metabolism and high pressure, X-ray, immunology etc.) being Cell Differentiation used in sequence determination today. 1977.52 figures, 7 tables. VI, l30 pages ISBN 3-540-08081-3 Volume 26: A.S.Brill The volume is based on the concept that the Transition Metals in Biochemistry biosynthesis of secondary natural substances is a 1977.49 figures, 18 tables. VIII, 186 pages widely found characteristic of cell specialization ISBN 3-540-08291-3 in almost all organisms. The central theme together with chapters on coordinated enzyme This monograph is a concise review of the current synthesis and possible effectors of gene expres• state and developments in the field, with sion in this field of metabolism, is the analysis of emphasis upon the application of physical differentiating programs, including the formation methods to the investigation of metal coordina• of enzymes of secondary metabolism. Particular tion. Molecular functions of proteins containing aspects of the formation of secondary natural transition metal ion prosthetic groups are summa• substances in plant cell culture are treated in a rized. Where established by X-ray diffraction, the separate chapter. three-dimensional structures of relevant metal binding sites in proteins are described. Light absorption and electron paramagnetic resonance are treated in depth. Those aspects of the theory Volume 24 are presented which can be directly employed in the quantification and interpretation of experi• Chemical Relaxation in mental data. The monograph provides a basis for closer communication between scientists of diffe• Molecular Biology rent backgrounds with a common interest in the Editors: I. Pecht, RRigler biochemistry of transition metal ions. With contributions by numerous experts 1977.141 figures, 50 tables. XVI, 418 pages ISBN 3-540-08173-9 The purpose of this monograph is to give a repre• sentative cross section of the current research activities dedicated to the analysis of essential steps in biological reactions. This covers the range of the following topics: hydrogen-bond formation, nucleotide base pairing, protein folding, isomerisation of protein and nucleic acid conformations, interactions between protein and proteins, nucleic acid and proteins, enzymes and Springer-Verlag substrates, antibody and hap tens or ionic transport through membranes. A common deno• Berlin minator in these studies is the search for an understanding of the laws that govern the Heidelherg dynamic behaviour of living systems. New York Volume 29: E.Heinz Molecular Biology Mechanics and Energetics of Biochemistry Biological Transport 1978. 35 figures, 3 tables. XV, 159 pages and Biophysics ISBN 3-540-08905-5 Editors: A.Kleinzeller, G.P. Springer, This book presents the interrelations of mecha• H. G. Wittmann nistic models on the one hand and the kinetic and energetic behavior of transport and permeatin processes on the other, using the principles of Volume 27 irreversible thermodynamics. The advantages of each method are compared. The special aim is to Effects of Ionizing Radiation show how to appropriate formulas can be trans• on DNA formed into each other, in order to recognize in Physical, Chemical and Biological Aspects what way the kinetic parameters correspond to those of irreversible thermodynamics. Editors: A.J.Bertinchamps (Coordinating Editor), J.Hiittermann, W.KOhnlein, R Teoule Volume 31 With contribution by numerous experts 1978. 74 figures, 48 tables. XXII, 383 pages Membrane Spectroscopy ISBN 3-540-08542-4 Editor: E. Grell With contribution by numerous experts For the first time, the three essential approaches to research on the effects of ionizing radiation on 1981. 146 figures. XI, 498 pages DNA and its constituents have been described ISBN 3-540-10332-5 together in one book, providing an overall view of The aim ofthe book is to introduce the reader to the fundamental problems involved. A result of the application of spectroscopic methods to the the European study group on "Primary Effects of study of membranes. Each chapter summarizes Radiation on Nucleic Acids", this book contains the experimental and theoretical principles of a the current state of knowledge in this field, and particular technique and the special applications has been written in close collaboration by 27 of that technique to the investigation of authors. membranes. The contributions critically review the current exploitation of the technique by considering the results obtained on membrane Volume 28: A.Levitzki constituents, simple model membranes and on Quantitative Aspects of Allosteric biological membrane systems of a highly complex nature. A common aspect in all the Mechanisms chapters is the intensive search for a detailed 1978. 13 figures, 2 tables. VIII, 106 pages understanding ofthe structures and functions of ISBN 3-540-08696-X biological membranes at a molecular level. This book provides a concise but comprehensive Volume 32 treatment of the basic regulatory phenomena of allostery and cooperativity. It critically evaluates Chemical Recognition in Biology the differences between the allosteric models and Editors: F.Chapeville, A.-L.Haenni their applicability to real situations. For the first With contributions by numerous experts time the analysis of the different allosteric full 1980. 210 figures, 39 tables. IX, 430 pages models is given, and compared with the pure ISBN 3-540-10205-1 thermodynamic approach. The treatment of the subject of allostery in this book is of great value to This volume is a collection of papers presented at enzymologist, receptorologist, pharmacologists the Symposium on Chemical Recognition in and endocrinologists, as it provides the basic Biology organized in Grignon (France) in July rules for the study ofligand-protein and l~d­ 1979 on the occasion of the 80th anniversary of receptor interactions. Fritz Lipmann, one of the most outstanding figures of modem biochemistry. The topics covered in this book extend from precise enzy• matic systems to highly complex cellular orga• Springer-Verlag nisms. Special emphasis is laid on recognition of ligands, enzymic catalysis, enzyme regulation, Berlin nucleic adic-protein interactions, mutagenesis, and protein biosynthesis. The volume concludes Heidelberg with philosophical reflections on molecular biolo• gy, culture and society, and personal recollections New York on Fritz Lipmann.