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1：Medicinal Natural Products 2ed
CONTENTS
1 ABOUT THIS BOOK, AND HOW TO USE IT
The Subject
The Aim
The Approach
The Topics
Be Selective
To Learn, or to Understand?
Conventions Regarding Acids, Bases, and Ions
Nomenclature
Some Common Abbreviations
Further Reading
2 SECONDARY METABOLISM: THE BUILDING BLOCKS AND CONSTRUCTION
MECHANISMS
Primary and Secondary Metabolism
The Building Blocks
The Construction Mechanisms
Alkylation Reactions: Nucleophilic Substitution
Alkylation Reactions: Electrophilic Addition
Wagner–Meerwein Rearrangements
Aldol and Claisen Reactions
Schiff Base Formation and the Mannich Reaction
Transamination
Decarboxylation Reactions
Oxidation and Reduction Reactions
Dehydrogenases
Oxidases
Mono-oxygenases
Dioxygenases
Amine Oxidases
Baeyer–Villiger Oxidations
Phenolic Oxidative Coupling
Glycosylation Reactions
Some Vitamins Associated with the Construction Mechanisms
Vitamin B1 , Vitamin B2 , Vitamin B5 , Vitamin B6 , Vitamin B12 , Vitamin H
Further Reading
3 THE ACETATE PATHWAY: FATTY ACIDS AND POLYKETIDES
Saturated Fatty Acids
Unsaturated Fatty Acids
Fixed Oils and Fats, Evening Primrose Oil
Acetylenic Fatty Acids
Branched-Chain Fatty Acids
Echinacea
viii CONTENTS
Prostaglandins
Prostaglandins, Isoprostanes
Thromboxanes
Thromboxanes
Leukotrienes
Leukotrienes
Aromatic Polyketides
Cyclization: Simple Phenols
Structural Modifications: Anthraquinones
Senna, Cascara, Frangula, Allied Drugs, Hypericum/St John’s Wort
C-Alkylation Reactions
Mycophenolic Acid, Khellin and Cromoglicate
Phenolic Oxidative Coupling
Griseofulvin
Oxidative Cleavage of Aromatic Rings
Starter Groups Other Than Acetate
Poison Ivy and Poison Oak, Aflatoxins, Cannabis, Tetracyclines, Anthracycline
Antibiotics
Macrolides and Polyethers
Extender Groups other than Malonate
Macrolide Antibiotics, Avermectins, Polyene Antifungals, Tacrolimus and Sirolimus,
Ansa Macrolides
Cyclization Through Diels–Alder Reactions
Mevastatin and other Statins
Genetic Manipulation of the Acetate Pathway
Further Reading
4 THE SHIKIMATE PATHWAY: AROMATIC AMINO ACIDS AND
PHENYLPROPANOIDS
Aromatic Amino Acids and Simple Benzoic Acids
Folic Acid (Vitamin B9 ), Chloramphenicol
Cinnamic Acids
Lignans and Lignin
Podophyllum
Phenylpropenes
Volatile Oils Containing Principally Aromatic Compounds
Benzoic Acids from C6C3 Compounds
Coumarins
Dicoumarol and Warfarin, Psoralens
Styrylpyrones
Kava
Flavonoids and Stilbenes
Flavonolignans
Silybum marianum
Isoflavonoids
Phyto-oestrogens, Derris and Lonchocarpus
Terpenoid Quinones
Vitamin E, Vitamin K
Further Reading
CONTENTS ix
5 THE MEVALONATE AND DEOXYXYLULOSE PHOSPHATE PATHWAYS:
TERPENOIDS AND STEROIDS 167
Hemiterpenes (C5)
Monoterpenes (C10)
Volatile Oils Containing Principally Terpenoid Compounds
Irregular Monoterpenes
Pyrethrins
Iridoids (C10)
Valerian
Sesquiterpenes (C15)
Feverfew, Chamomile and Matricaria, Artemisia annua and Artemisinin, Gossypol,
Trichothecenes
Diterpenes (C20)
Taxus brevifolia and Taxol (Paclitaxel), Ginkgo biloba, Forskolin
Sesterterpenes (C25)
Triterpenes (C30)
Triterpenoid Saponins
Liquorice, Quillaia, Ginseng
Modified Triterpenoids
Tetraterpenes (C40)
Vitamin A
Higher Terpenoids
Steroids
Stereochemistry
Cholesterol
Cholesterol
Steroidal Saponins
Dioscorea, Fenugreek, Sisal, Sarsaparilla, Yucca
Cardioactive Glycosides
Digitalis purpurea, Digitalis lanata, Strophanthus, Convallaria, Squill, Toxic Plants
Phytosterols
Soya Bean Sterols, Fusidic Acid
Vitamin D
Vitamin D
Bile Acids
Bile Acids
Adrenocortical Hormones/Corticosteroids
Semi-Synthesis of Corticosteroids
Corticosteroid Drugs
Progestogens
Progestogen Drugs
Oestrogens
Oestrogen Drugs, Aromatase Inhibitors, Oestrogen Receptor Antagonists
Androgens
Androgen Drugs
Further Reading
x CONTENTS
6 ALKALOIDS
Alkaloids Derived from Ornithine
Pyrrolidine and Tropane Alkaloids
Belladonna, Stramonium, Hyosycamus, Duboisia, Allied Drugs, Hyoscyamine,
Hyoscine and Atropine, Coca
Pyrrolizidine Alkaloids
Alkaloids Derived from Lysine
Piperidine Alkaloids
Lobelia
Quinolizidine Alkaloids
Indolizidine Alkaloids
Alkaloids Derived from Nicotinic Acid
Pyridine Alkaloids
Vitamin B3 , Tobacco, Areca
Alkaloids Derived from Tyrosine
Phenylethylamines and Simple Tetrahydroisoquinoline Alkaloids
Catecholamines, Areca, Lophophora, Curare
Modified Benzyltetrahydroisoquinoline Alkaloids
Opium
Phenethylisoquinoline Alkaloids
Colchicum
Terpenoid Tetrahydroisoquinoline Alkaloids
Ipecacuanha
Amaryllidaceae Alkaloids
Galanthamine
Alkaloids Derived from Tryptophan
Simple Indole Alkaloids
5-Hydroxytryptamine (Serotonin), Psilocybe
Simple β-Carboline Alkaloids
Terpenoid Indole Alkaloids
Rauwolfia, Catharanthus, Iboga, Nux-vomica, Ellipticine
Quinoline Alkaloids
Cinchona, Camptothecin
Pyrroloindole Alkaloids
Physostigma
Ergot Alkaloids
Ergot, Morning Glories
Alkaloids Derived from Anthranilic Acid
Quinazoline Alkaloids
Quinoline and Acridine Alkaloids
Alkaloids Derived from Histidine
Imidazole Alkaloids
Pilocarpus
Alkaloids Derived by Amination Reactions
Acetate-derived Alkaloids
Conium maculatum
Phenylalanine-derived Alkaloids
Ephedra, Khat
Terpenoid Alkaloids
Aconite
CONTENTS xi
Steroidal Alkaloids
Solanum Alkaloids
Purine Alkaloids
Caffeine, Theobromine, and Theophylline, Coffee, Tea, Cola, Cocoa, Mat´e Tea,
Guarana
Saxitoxin and Tetrodotoxin
Saxitoxin, Tetrodotoxin
Further Reading
7 PEPTIDES, PROTEINS, AND OTHER AMINO ACID DERIVATIVES
Peptides and Proteins
Ribosomal Peptide Biosynthesis
Peptide Hormones
Thyroid Hormones
Thyroxine, Calcitonin
Hypothalamic Hormones
Thyrotrophin-Releasing Hormone, Luteinizing Hormone-Releasing Hormone, Growth
Hormone-Releasing Hormone/Factor, Somatostatin
Anterior Pituitary Hormones
Corticotropin, Growth Hormone, Prolactin, Gonadotrophins
Posterior Pituitary Hormones
Oxytocin, Vasopressin
Pancreatic Hormones
Insulin, Glucagon
Interferons
Interferons
Opioid Peptides
Enzymes
Nonribosomal Peptide Biosynthesis
Peptide Antibiotics
Cycloserine, Polymyxins, Bacitracins, Tyrothricin and Gramicidins, Capreomycin,
Vancomycin and Teicoplanin, Bleomycin, Cyclosporins, Streptogramins,
Dactinomycin
Peptide Toxins
Death Cap (Amanita phalloides), Ricin, Botulinum Toxin, Microcystins, Snake Venoms
Modified Peptides: Penicillins, Cephalosporins, and Other β-Lactams
Penicillins
Penicillins
Cephalosporins
Cephalosporins, Cephamycins, Carbacephems
Other β-Lactams
Clavulanic Acid, Carbapenems, Monobactams
Cyanogenic Glycosides
Glucosinolates
Cysteine Sulphoxides
Garlic
Further Reading
xii CONTENTS
8 CARBOHYDRATES
Monosaccharides
Oligosaccharides
Monosaccharides and Disaccharides, Vitamin C
Polysaccharides
Polysaccharides
Aminosugars
Aminoglycosides
Aminoglycoside Antibiotics, Streptamine-containing Antibiotics,
2-Deoxystreptamine-containing Antibiotics, Acarbose, Lincomycin and Clindamycin
Further Reading
Index