Medicinal Natural Products: A Biosynthetic Approach, 3rd Edition

The Subject.

The Aim.

The Approach.

The Topics.

The Figures.

Further Reading.

What to Study.

What to Learn.

Nomenclature.

Conventions Regarding Acids, Bases, and Ions.

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.

Dehydrogenases.

Oxidases.

Monooxygenases.

Dioxygenases.

Amine Oxidases.

Baeyer-Villiger Monooxygenases.

Some Vitamins Associated with the Construction Mechanisms.

Elucidating Biosynthetic Pathways.

Further Reading.

3. THE ACETATE PATHWAY: FATTY ACIDS AND POLYKETIDES.

Fatty Acid Synthase: Saturated Fatty Acids.

Unsaturated Fatty Acids.

Uncommon Fatty Acids.

Prostaglandins.

Thromboxanes.

Leukotrienes.

Polyketide Synthases: Generalities.

Polyketide Synthases: Macrolides.

Macrolide Antibiotics, Erythromycins, Oleandomycin and Spiramycin, Tylosin, Avermectins, Polyene Antifungals, Tacrolimus and Sirolimus, Rifamycins.

Polyketide Synthases: Linear Polyketides and Polyethers.

Diels-Alder Cyclizations.

Polyketide Synthases: Aromatics.

Senna, Hypericum / St John?s Wort, Mycophenolic acid, Khellin and Cromoglicate, Griseofulvin.

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

Further Reading.

4. THE SHIKIMATE PATHWAY: AROMATIC AMINO ACIDS AND PHENYLPROPANOIDS.

Aromatic Amino Acids and Simple Benzoic Acids.

Phenylpropanoids.

Cinnamic Acids and Esters.

Lignans and Lignin.

Phenylpropenes.

Benzoic Acids from C6C3 Compounds.

Coumarins.

Aromatic Polyketides.

Styrylpyrones, Diarylheptanoids.

Flavonoids and Stilbenes.

Flavonolignans.

Isoflavonoids.

Terpenoid Quinones.

Further Reading.

5. THE MEVALONATE AND METHYLERYTHRITOL PHOSPHATE PATHWAYS: TERPENOIDS AND STEROIDS.

Mevalonic Acid and Methylerythritol Phosphate.

Hemiterpenes.

Monoterpenes.

Irregular Monoterpenes.

Iridoids.

Sesquiterpenes.

Artemisinin, Gossypol, Trichothecenes.

Diterpenes.

Sesterterpenes.

Triterpenes.

Steroids.

Stereochemistry and Nomenclature.

Cholesterol.

Phytosterols.

Vitamin D.

Steroidal Saponins.

Cardioactive Glycosides.

Bile Acids.

Adrenocortical Hormones/Corticosteroids.

Semi-Synthesis of Corticosteroids.

Progestogens.

Oestrogens.

Androgens.

Tetraterpenes.

Higher Terpenoids.

Further Reading.

6. ALKALOIDS.

Alkaloids Derived from Ornithine.

Alkaloids Derived from Lysine.

Alkaloids Derived from Nicotinic Acid.

Alkaloids Derived from Tyrosine.

Phenylethylamines and Simple Tetrahydroisoquinoline Alkaloids.

Modified Benzyltetrahydroisoquinoline Alkaloids.

Phenethylisoquinoline Alkaloids.

Terpenoid Tetrahydroisoquinoline Alkaloids.

Amaryllidaceae Alkaloids.

Alkaloids Derived from Tryptophan.

Simple Indole Alkaloids.

Simple - Carboline Alkaloids.

Terpenoid Indole Alkaloids.

Quinoline Alkaloids.

Pyrroloindole Alkaloids.

Ergot Alkaloids.

Alkaloids Derived from Anthranilic Acid.

Alkaloids Derived From Histidine.

Alkaloids Derived by Amination Reactions.

Acetate-Derived Alkaloids.

Phenylalanine-Derived Alkaloids.

Terpenoid Alkaloids.

Steroidal Alkaloids.

Purine Alkaloids.

Further Reading.

7. PEPTIDES, PROTEINS, AND OTHER AMINO ACID DERIVATIVES.

Peptides and Proteins.

Ribosomal Peptide Biosynthesis.

Peptide Hormones.

Thyroid Hormones.

Hypothalamic Hormones.

Hormone, Growth Hormone-releasing Hormone/Factor, Somatostatin.

Anterior Pituitory Hormones.

Posterior Pituitory Hormones.

Pancreatic Hormones.

Interferons.

Opioid Peptides.

Ribosomal Peptide Toxins.

Death Cap (Amanita phalloides), Ricin, Botulinum Toxin, Conotoxins, Snake Venoms, Gila Monster Venom.

Enzymes.

Nonribosomal Peptide Biosynthesis.

Bacitracins, Capreomycin, Polymyxins, Daptomycin, Cyclosporins, Vancomycin and Teicoplanin, Bleomycin, Streptogramins, Dactinomycin, Cycloserine.

Modified Peptides: Penicillins, Cephalosporins and Other ?-Lactams.

Cyanogenic Glycosides.

Glucosinolates.

Cysteine Sulphoxides.

Further Reading.

8. CARBOHYDRATES.

Monosaccharides.

Oligosaccharides.

Polysaccharides.

Aminosugars and Aminoglycosides.

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

Further Reading.

Index.