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Index
Preface
Contents
I: Basics and History of Plant Secondary Metabolites
1: Plant Secondary Metabolites and Their General Function in Plants
1.1 General Classification of Secondary Metabolites (Details in Part IV)
1.2 Overview of Classes of Secondary Metabolites (Details in Part IV)
1.3 Overview of the Function of Secondary Metabolites in Plants (Details in Part IV)
1.3.1 Adaptation to a Life on Land
1.3.2 Attraction (or Deterrent) of Pollinators and Seed Dispersers
Box 1.1 Toxic Honey
Box 1.2 Did Humans Save the Avocado from Extinction?
1.3.3 Defence Against Herbivores, Pathogens and Other Pests
1.3.4 Plant-to-Plant Communication
1.3.5 Constitutive versus Induced Expression
1.3.6 Counterstrategies of the Attacker and Use of Plant-Derived Secondary Metabolites by Other Animals
Box 1.3 Defensive Halitosis
1.3.7 Avoidance of Auto-Toxicity and Premature Toxin Release
References
2: Historical and Current Perspective
2.1 History of Medical Use
2.2 History of Recreational Use
Box 2.1 The Poppy Goddess
References
II: Drugs and Their Human Receptors
3: GPCRs
3.1 G-Protein-Coupled Receptors
Box 3.1 Catecholamine
3.2 Trimeric G-Proteins
Box 3.2 Small G-proteins or small GTPases
Box 3.3 MAP kinases
3.3 GS, Golf and Gi Targeting Adenylyl Cyclase
3.4 Gq Targeting Phospholipase C
3.5 Signal Termination
References
4: Ion Channels
4.1 Channels and Transporters
4.2 Membrane Potential and Electrochemical Gradient
4.3 Voltage-Gated Ion Channels
4.3.1 Voltage-Gated K+-Channels
4.3.2 Voltage-Gated Na+-Channels
4.3.3 Voltage-Gated Ca2+-Channels
4.3.4 Neuromuscular Junction
4.3.5 VOCs and Neurotransmitter Release
4.4 Extracellular Ligand-Operated Channels: Neurotransmitter Receptors
4.5 TRP Channels
References
5: GPCRs as Targets for Plant-Derived Drugs
5.1 Muscarinic Acetylcholine Receptors (MAchR): Muscarine, Atropine and Physostigmine
Box 5.1 Allosteric Regulator
5.2 Adrenergic Receptors: Reserpine and Ephedrine
5.3 Adenosine Receptors: Caffeine
Box 5.2 Drug Tolerance and Dependence
5.4 Cannabinoid Receptors: Cannabis and Cannabinoids
5.5 Dopamine Receptors: Neuroleptics and Cocaine
5.6 5HT2A Receptors: Psilocybin, Mescaline and Dimethyltryptamine
Box 5.3 Schizophrenia
5.7 Opioid Receptors: Morphine, Heroin and Salvinorin A
References
6: Ion Channels as Targets for Plant-Derived Drugs
6.1 Neurotoxin Binding Sites on Voltage-Gated Ion Channels
6.2 Nicotinic Acetylcholine Receptor (NAchR): Nicotine
6.3 GABAA Receptors: Muscimol, Valerenic Acid, Thujone and Benzamidines
6.4 Glycine Receptor: Strychnine and Tutin
6.5 Glutamate Receptors: Ibotenic Acid, Kainate and Ketamine
6.6 TRPV and TRPM8: Heat and Cold, Capsaicin and Menthol
References
III: Plant-Derived Drugs: Their Function in Plants and Potential Biotechnological Use
7: Plant-Derived Drugs Affecting GPRCs
7.1 Muscarinic Acetylcholine Receptors: Atropine, Muscarine and Scopolamine
7.2 Adrenergic Receptors: Ephedrine and Reserpine
7.3 Adenosine Receptors: Caffeine
Box 7.1 Effect of Caffeine on Spiders
7.4 Cannabinoid Receptors: Phytocannabinoids
Box 7.2 Short History of Hemp Usage
7.5 Dopamine Receptors: Cocaine and L-DOPA
7.6 5HT2A Receptors: Ergotamine and Mescaline
7.7 Opioid Receptor: Morphine/Opiates and Opioids
Box 7.3 Recipe for Theriac, an ancient universial remedy
References
8: Plant-Derived Drugs Affecting Ion Channels
8.1 Voltage-Gated Ion Channels: Aconitine, Saxitoxin and Ryanodine
8.2 Nicotinic Acetylcholine Receptors: Nicotine, Coniine, Curare and Anatoxin A
Box 8.1 Nicotine and the onset of modern forensics
Box 8.2 Defensive halitosis
8.3 GABAA Receptors: Thujone, Cicutoxin and Anisatin
Box 8.3 La fée verte
8.4 Glycine Receptors: Strychnine and Tutin
Box 8.4 Strychnine and the 1904 Olympics
8.5 Ionotropic Glutamate Receptors: Ibogaine, Kainic and Domoic Acid
8.6 TRPV and TRPM8 Receptors: Capsaicin and Menthol
References
IV: Biosynthesis of Secondary Metabolites in Plants
9: Secondary Metabolites in Plants: General Introduction
9.1 Role of Secondary Metabolites for Plant Development
9.2 Regulation of the Biosynthesis of Secondary Metabolites
9.3 General Mechanisms for Biosynthesis
References
10: Terpenes and Terpenoids
10.1 Introduction
10.2 Monoterpenes (From MEP Pathway, C10, e.g. Menthol, Camphor and Thujone)
Box 10.1 Terpene Synthases (TPS)
Box 10.2 Essential Oils
10.3 Diterpene (From MEP Pathway, C20, e.g. Salvinorin A and Ryanodine)
10.4 Tetraterpene (From MEP Pathway, C40)
10.5 Sesquiterpenes (From MVA Pathway, C15, e.g. Valerenic Acid, Anisatin and Tutin)
10.6 Sterols and Triterpene (From MVA Pathway, C30)
References
11: Phenylpropanoids
11.1 Shikimate Pathway (Phenylalanine, Tyrosine and Tryptophan)
11.2 Phenylpropanoids (Derived from Phenylalanine)
References
12: Alkaloids
12.1 Introduction
12.2 Terpenoid Indole Alkaloids (Derived from Tryptophan, e.g. Ibogaine, Reserpine, Strychnine, Physostigmine, Dimethyltryptamine, Psilocybin and Ergotamine)
12.3 Benzylisoquinoline Alkaloids (Derived from Tyrosine, e.g. Morphine and Curare)
12.4 Phenethylamine Alkaloids (Derived from Tyrosine, e.g. Mescaline)
12.5 Phenylethylamine (Derived from Phenylalanine, e.g. Ephedrine)
12.6 Alkaloids from Condensation of Tyrosine and Phenylalanine
12.6.1 Amaryllidaceae (Norbelladine)
12.6.2 Phenylethylisoquinoline Alkaloids
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
12.8 Pyrrolizidine Alkaloids (Derived from Spermidine and Putrescine)
12.9 Purine Alkaloids (Derived from Xanthosine, e.g. Caffeine)
12.10 Piperidine Alkaloids (e.g. Lobeline), Quinolizidine Alkaloids (e.g. Cytisine) and Indolizidine Alkaloids (All Derived from Lysine)
12.11 Steroidal Alkaloids (From Steroids Derived from the MVA Pathway)
12.12 Terpenoid Alkaloids (Derived from the MEP Pathway, e.g. Aconitine)
12.13 Tropane-Related Alkaloids (Derived from Proline, e.g. Anatoxin A)
12.14 Isoxazole Alkaloids (e.g. Muscimol)
12.15 Muscarine
12.16 Guanidinium Toxins (e.g. Saxitoxin)
12.17 Kainoids
References
13: Minor Groups of Secondary Metabolites
13.1 Quinone
13.2 Polyketide (e.g. Cannabinoids)
13.3 Fatty Acid-Derived Metabolites
13.3.1 Polyacetylenes (e.g. Cicutoxin)
13.3.2 N-Acylethanolamines
13.3.3 Alkylamides, N-acyl amides (e.g. Capsaicin)
13.3.4 Conium Alkaloids (Pseudoalkaloids, e.g. Coniine)
13.4 Non-protein Amino Acids
13.5 Acetylcholine
References
Glossary
Compounds
Side Groups
Reactions
Nomenclature
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