Medicinal Natural Products: A Biosynthetic Approach, 3rd Edition

by Paul M. Dewick (Univ. of Nottingham, UK)

• ISBN13: 9780470742792
• ISBN10: 0470742798
• Format: eBook
• Copyright: 2009-01-01
• Publisher: Wiley

Summary

Medicinal Natural Products, Third Edition, provides a comprehensive and balanced introduction to natural products from a biosynthetic perspective, focusing on the metabolic sequences leading to various classes of natural products. The book builds upon fundamental chemical principles and guides the reader through a wealth of diverse natural metabolites with particular emphasis on those used in medicine: sources, production methods, use as drugs, semi-synthetic derivatives and synthetic analogues, and modes of action are all extensively covered.Rapid advances have been made in the last decade in gene isolation and genetic engineering, leading to the elaboration of many biosynthetic pathways. Medicinal Natural Products has been extended and fully updated in this new edition to reflect and explain these new developments and other advances in the field. It retains the user-friendly style and highly acclaimed features of previous editions: a comprehensive treatment of plant, microbial, and animal natural products in one volume extensive use of chemical schemes with annotated mechanistic explanations cross-referencing to emphasize links and similarities boxed topics giving further details of medicinal materials, covering sources, production methods, use as drugs, semi-synthetic derivatives and synthetic analogues, and modes of actionMedicinal Natural Products, Third Edition, is an invaluable textbook for students of pharmacy, pharmacognosy, medicinal chemistry, biochemistry and natural products synthesis.

Table of Contents

About This Book, And How To Use It

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

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

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

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

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

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

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

Carbohydrates

Monosaccharides

Oligosaccharides

Polysaccharides

Aminosugars and Aminoglycosides

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

Further Reading

Index

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