IX
IV Biosynthesis of Secondary Metabolites in Plants
9
Secondary Metabolites in Plants: General Introduction ..................................... 143
9.1
Role of Secondary Metabolites for Plant Development ....................................................... 144
9.2
Regulation of the Biosynthesis of Secondary Metabolites .................................................. 145
9.3
General Mechanisms for Biosynthesis ......................................................................................... 147
References ............................................................................................................................................... 151
10
Terpenes and Terpenoids .......................................................................................................... 153
10.1
Introduction .......................................................................................................................................... 154
10.2
Monoterpenes (From MEP Pathway, C10, e.g. Menthol, Camphor and Thujone) ....... 157
10.3
Diterpene (From MEP Pathway, C20, e.g. Salvinorin A and Ryanodine) ......................... 161
10.4
Tetraterpene (From MEP Pathway, C40) ...................................................................................... 162
10.5
Sesquiterpenes (From MVA Pathway, C15, e.g. Valerenic Acid,
Anisatin and Tutin) .............................................................................................................................. 163
10.6
Sterols and Triterpene (From MVA Pathway, C30) ................................................................... 165
References ............................................................................................................................................... 168
11
Phenylpropanoids ......................................................................................................................... 171
11.1
Shikimate Pathway (Phenylalanine, Tyrosine and Tryptophan) ........................................ 172
11.2
Phenylpropanoids (Derived from Phenylalanine) .................................................................. 174
References ............................................................................................................................................... 177
12
Alkaloids .............................................................................................................................................. 179
12.1
Introduction .......................................................................................................................................... 181
12.2
Terpenoid Indole Alkaloids (Derived from Tryptophan, e.g. Ibogaine, Reserpine,
Strychnine, Physostigmine, Dimethyltryptamine, Psilocybin and Ergotamine) ......... 181
12.3
Benzylisoquinoline Alkaloids (Derived from Tyrosine,
e.g. Morphine and Curare) ............................................................................................................... 186
12.4
Phenethylamine Alkaloids (Derived from Tyrosine, e.g. Mescaline) ................................ 189
12.5
Phenylethylamine (Derived from Phenylalanine, e.g. Ephedrine) ................................... 189
12.6
Alkaloids from Condensation of Tyrosine and Phenylalanine ........................................... 190
12.6.1 Amaryllidaceae (Norbelladine) ......................................................................................................... 190
12.6.2 Phenylethylisoquinoline Alkaloids .................................................................................................. 191
12.7
Pyridine Alkaloids (e.g. Nicotine), Pyrrolidine Alkaloids (e.g. Hygrine)
and Tropane Alkaloids (e.g. Atropine, Scopolamine and Cocaine)
All Derived from Ornithine and Arginine ................................................................................... 191
12.8
Pyrrolizidine Alkaloids (Derived from Spermidine and Putrescine) ................................ 194
12.9
Purine Alkaloids (Derived from Xanthosine, e.g. Caffeine) ................................................. 195
12.10 Piperidine Alkaloids (e.g. Lobeline), Quinolizidine Alkaloids (e.g. Cytisine)
and Indolizidine Alkaloids (All Derived from Lysine) ............................................................. 196
12.11 Steroidal Alkaloids (From Steroids Derived from the MVA Pathway) .............................. 197
Contents
IV Biosynthesis of Secondary Metabolites in Plants
9
Secondary Metabolites in Plants: General Introduction ..................................... 143
9.1
Role of Secondary Metabolites for Plant Development ....................................................... 144
9.2
Regulation of the Biosynthesis of Secondary Metabolites .................................................. 145
9.3
General Mechanisms for Biosynthesis ......................................................................................... 147
References ............................................................................................................................................... 151
10
Terpenes and Terpenoids .......................................................................................................... 153
10.1
Introduction .......................................................................................................................................... 154
10.2
Monoterpenes (From MEP Pathway, C10, e.g. Menthol, Camphor and Thujone) ....... 157
10.3
Diterpene (From MEP Pathway, C20, e.g. Salvinorin A and Ryanodine) ......................... 161
10.4
Tetraterpene (From MEP Pathway, C40) ...................................................................................... 162
10.5
Sesquiterpenes (From MVA Pathway, C15, e.g. Valerenic Acid,
Anisatin and Tutin) .............................................................................................................................. 163
10.6
Sterols and Triterpene (From MVA Pathway, C30) ................................................................... 165
References ............................................................................................................................................... 168
11
Phenylpropanoids ......................................................................................................................... 171
11.1
Shikimate Pathway (Phenylalanine, Tyrosine and Tryptophan) ........................................ 172
11.2
Phenylpropanoids (Derived from Phenylalanine) .................................................................. 174
References ............................................................................................................................................... 177
12
Alkaloids .............................................................................................................................................. 179
12.1
Introduction .......................................................................................................................................... 181
12.2
Terpenoid Indole Alkaloids (Derived from Tryptophan, e.g. Ibogaine, Reserpine,
Strychnine, Physostigmine, Dimethyltryptamine, Psilocybin and Ergotamine) ......... 181
12.3
Benzylisoquinoline Alkaloids (Derived from Tyrosine,
e.g. Morphine and Curare) ............................................................................................................... 186
12.4
Phenethylamine Alkaloids (Derived from Tyrosine, e.g. Mescaline) ................................ 189
12.5
Phenylethylamine (Derived from Phenylalanine, e.g. Ephedrine) ................................... 189
12.6
Alkaloids from Condensation of Tyrosine and Phenylalanine ........................................... 190
12.6.1 Amaryllidaceae (Norbelladine) ......................................................................................................... 190
12.6.2 Phenylethylisoquinoline Alkaloids .................................................................................................. 191
12.7
Pyridine Alkaloids (e.g. Nicotine), Pyrrolidine Alkaloids (e.g. Hygrine)
and Tropane Alkaloids (e.g. Atropine, Scopolamine and Cocaine)
All Derived from Ornithine and Arginine ................................................................................... 191
12.8
Pyrrolizidine Alkaloids (Derived from Spermidine and Putrescine) ................................ 194
12.9
Purine Alkaloids (Derived from Xanthosine, e.g. Caffeine) ................................................. 195
12.10 Piperidine Alkaloids (e.g. Lobeline), Quinolizidine Alkaloids (e.g. Cytisine)
and Indolizidine Alkaloids (All Derived from Lysine) ............................................................. 196
12.11 Steroidal Alkaloids (From Steroids Derived from the MVA Pathway) .............................. 197
Contents