Contents

Grow Taller 4 Idiots

How to Grow Taller

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1 ABOUT THIS BOOK, AND HOW TO USE IT 1

The Subject 1

The Aim 1

The Approach 2

The Topics 2

Be Selective 2

To Learn, or to Understand? 3

Conventions Regarding Acids, Bases, and Ions 3

Nomenclature 3

Some Common Abbreviations 4

Further Reading 4

2 SECONDARY METABOLISM: THE BUILDING BLOCKS AND CONSTRUCTION

MECHANISMS 7

Primary and Secondary Metabolism 7

The Building Blocks 8

The Construction Mechanisms 12

Alkylation Reactions: Nucleophilic Substitution 12

Alkylation Reactions: Electrophilic Addition 13

Wagner-Meerwein Rearrangements 15

Aldol and Claisen Reactions 15

Schiff Base Formation and the Mannich Reaction 18

Transamination 20

Decarboxylation Reactions 20

Oxidation and Reduction Reactions 24

Dehydrogenases 24

Oxidases 25

Mono-oxygenases 25

Dioxygenases 27

Amine Oxidases 28

Baeyer-Villiger Oxidations 28

Phenolic Oxidative Coupling 28

Glycosylation Reactions 29

Some Vitamins Associated with the Construction Mechanisms 30

Vitamin Bj, Vitamin B2, Vitamin B5, Vitamin B6, Vitamin Bj2, Vitamin H

Further Reading 33

3 THE ACETATE PATHWAY: FATTY ACIDS AND POLYKETIDES 35

Saturated Fatty Acids 36

Unsaturated Fatty Acids 40

Fixed Oils and Fats, Evening Primrose Oil

Acetylenic Fatty Acids 47

Branched-Chain Fatty Acids 48

Echinacea

Prostaglandins 51

Prostaglandins, Isoprostanes Thromboxanes 58

Thromboxanes

Leukotrienes 58

Leukotrienes

Aromatic Polyketides 60

Cyclization: Simple Phenols 61

Structural Modifications: Anthraquinones 63

Senna, Cascara, Frangula, Allied Drugs, Hypericum/St John's Wort

C-Alkylation Reactions 72

Mycophenolic Acid, Khellin and Cromoglicate

Phenolic Oxidative Coupling 76

Griseofulvin

Oxidative Cleavage of Aromatic Rings 78

Starter Groups Other Than Acetate 79

Poison Ivy and Poison Oak, Aflatoxins, Cannabis, Tetracyclines, Anthracycline Antibiotics

Macrolides and Polyethers 92

Extender Groups other than Malonate 92

Macrolide Antibiotics, Avermectins, Polyene Antifungals, Tacrolimus and Sirolimus, Ansa Macrolides

Cyclization Through Diels-Alder Reactions 111

Mevastatin and other Statins

Genetic Manipulation of the Acetate Pathway 114

Further Reading 117

4 THE SHIKIMATE PATHWAY: AROMATIC AMINO ACIDS AND

PHENYLPROPANOIDS 121

Aromatic Amino Acids and Simple Benzoic Acids 121

Folic Acid (Vitamin B9), Chloramphenicol

Cinnamic Acids 130

Lignans and Lignin 132

Podophyllum

Phenylpropenes 135

Volatile Oils Containing Principally Aromatic Compounds

Benzoic Acids from C6C3 Compounds 141

Coumarins 142

Dicoumarol and Warfarin, Psoralens

Styrylpyrones 147

Kava

Flavonoids and Stilbenes 149

Flavonolignans 151

Silybum marianum

Isoflavonoids 154

Phyto-oestrogens, Derris and Lonchocarpus Terpenoid Quinones 158

Vitamin E, Vitamin K

Further Reading 164

5 THE MEVALONATE AND DEOXYXYLULOSE PHOSPHATE PATHWAYS:

TERPENOIDS AND STEROIDS 167

Hemiterpenes (C5) 172

Monoterpenes (C10) 172

Volatile Oils Containing Principally Terpenoid Compounds Irregular Monoterpenes 186

Pyrethrins

Iridoids (C10) 187

Valerian

Sesquiterpenes (C15) 191

Feverfew, Chamomile and Matricaria, Artemisia annua and Artemisinin, Gossypol, Trichothecenes

Diterpenes (C20) 203

Taxus brevifolia and Taxol (Paclitaxel), Ginkgo biloba, Forskolin

Sesterterpenes (C25) 212

Triterpenes (C30) 212

Triterpenoid Saponins 219

Liquorice, Quillaia, Ginseng

Modified Triterpenoids 225

Tetraterpenes (C40) 226

Vitamin A

Higher Terpenoids 231

Steroids 232

Stereochemistry 232

Cholesterol 233

Cholesterol

Steroidal Saponins 237

Dioscorea, Fenugreek, Sisal, Sarsaparilla, Yucca

Cardioactive Glycosides 241

Digitalis purpurea, Digitalis lanata, Strophanthus, Convallaria, Squill, Toxic Plants

Phytosterols 252

Soya Bean Sterols, Fusidic Acid

Vitamin D 257

Vitamin D

Bile Acids 260

Bile Acids

Adrenocortical Hormones/Corticosteroids 262

Semi-Synthesis of Corticosteroids 264

Corticosteroid Drugs

Progestogens 267

Progestogen Drugs

Oestrogens

Oestrogen Drugs, Aromatase Inhibitors, Oestrogen Receptor Antagonists

Androgens 282

Androgen Drugs

Further Reading 285

6 ALKALOIDS 291

Alkaloids Derived from Ornithine 292

Pyrrolidine and Tropane Alkaloids 292

Belladonna, Stramonium, Hyosycamus, Duboisia, Allied Drugs, Hyoscyamine, Hyoscine and Atropine, Coca

Pyrrolizidine Alkaloids 305

Alkaloids Derived from Lysine 307

Piperidine Alkaloids 307

Lobelia 308

Quinolizidine Alkaloids 309

Indolizidine Alkaloids 310

Alkaloids Derived from Nicotinic Acid 311

Pyridine Alkaloids 311

Vitamin B3, Tobacco, Areca

Alkaloids Derived from Tyrosine 315

Phenylethylamines and Simple Tetrahydroisoquinoline Alkaloids 315

Catecholamines, Areca, Lophophora, Curare

Modified Benzyltetrahydroisoquinoline Alkaloids 327

Opium 329

Phenethylisoquinoline Alkaloids 341

Colchicum

Terpenoid Tetrahydroisoquinoline Alkaloids 343

Ipecacuanha

Amaryllidaceae Alkaloids 345

Galanthamine

Alkaloids Derived from Tryptophan 346

Simple Indole Alkaloids 347

5-Hydroxytryptamine (Serotonin), Psilocybe

Simple ß-Carboline Alkaloids 349

Terpenoid Indole Alkaloids 350

Rauwolfia, Catharanthus, Iboga, Nux-vomica, Ellipticine

Quinoline Alkaloids 359

Cinchona, Camptothecin

Pyrroloindole Alkaloids 365

Physostigma

Ergot Alkaloids 368

Ergot, Morning Glories

Alkaloids Derived from Anthranilic Acid 376

Quinazoline Alkaloids 377

Quinoline and Acridine Alkaloids 377

Alkaloids Derived from Histidine 379

Imidazole Alkaloids 379

Pilocarpus

Alkaloids Derived by Amination Reactions 381

Acetate-derived Alkaloids 381

Conium maculatum

Phenylalanine-derived Alkaloids 382

Ephedra, Khat

Terpenoid Alkaloids 385

Aconite

Steroidal Alkaloids 388

Solanum Alkaloids

Purine Alkaloids 394

Caffeine, Theobromine, and Theophylline, Coffee, Tea, Cola, Cocoa, Maté Tea, Guaraña

Saxitoxin and Tetrodotoxin 396

Saxitoxin, Tetrodotoxin

Further Reading 398

7 PEPTIDES, PROTEINS, AND OTHER AMINO ACID DERIVATIVES 405

Peptides and Proteins 405

Ribosomal Peptide Biosynthesis 407

Peptide Hormones 410

Thyroid Hormones 410

Thyroxine, Calcitonin

Hypothalamic Hormones 411

Thyrotrophin-Releasing Hormone, Luteinizing Hormone-Releasing Hormone, Growth Hormone-Releasing Hormone/Factor, Somatostatin

Anterior Pituitary Hormones 413

Corticotropin, Growth Hormone, Prolactin, Gonadotrophins

Posterior Pituitary Hormones 413

Oxytocin, Vasopressin

Pancreatic Hormones 416

Insulin, Glucagon

Interferons 417

Interferons

Opioid Peptides 417

Enzymes 419

Nonribosomal Peptide Biosynthesis 421

Peptide Antibiotics 423

Cycloserine, Polymyxins, Bacitracins, Tyrothricin and Gramicidins, Capreomycin, Vancomycin and Teicoplanin, Bleomycin, Cyclosporins, Streptogramins, Dactinomycin

Peptide Toxins 433

Death Cap (Amanita phalloides), Ricin, Botulinum Toxin, Microcystins, Snake Venoms Modified Peptides: Penicillins, Cephalosporins, and Other ß-Lactams 422

Penicillins 422

Penicillins

Cephalosporins 444

Cephalosporins, Cephamycins, Carbacephems

Other ß-Lactams 450

Clavulanic Acid, Carbapenems, Monobactams

Cyanogenic Glycosides 455

Glucosinolates 457

Cysteine Sulphoxides 460

Garlic

Further Reading 461

8 CARBOHYDRATES 465

Monosaccharides 465

Oligosaccharides 469

Monosaccharides and Disaccharides, Vitamin C

Polysaccharides 473

Polysaccharides

Aminosugars 477

Aminoglycosides 478

Aminoglycoside Antibiotics, Streptamine-containing Antibiotics, 2-Deoxystreptamine-containing Antibiotics, Acarbose, Lincomycin and Clindamycin

Further Reading 486

Index 487

Medicinal Natural Products. Paul M Dewick Copyright © 2002 John Wiley & Sons, Ltd ISBNs: 0471496405 (Hardback); 0471496413 (paperback); 0470846275 (Electronic)

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