Medicinal natural products: a biosynthetic approach

1. 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

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

Imine formation and the Mannich reaction

Amino acids and transamination

Decarboxylation reactions

Oxidation and reduction reactions

Dehydrogenases

Oxidases

Monooxygenases

Dioxygenases

Amine oxidases

Baeyer-Villiger monooxygenases

Phenolic oxidative coupling

Halogenation reactions

Glycosylation reactions

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

Polyketide synthases: linear polyketides and polyethers

Diels-Alder cyclizations

Polyketide synthases: aromatics

Cyclizations

Post-polyketide synthase modifications

Starter groups

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 C 6 C 3 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 (C 5 )

Monoterpenes (C 10 )

Irregular monoterpenes

Iridoids (C 10 )

Sesquiterpenes (C 15 )

Diterpenes (C 20 )

Sesterterpenes (C 25 )

Triterpenes (C 30 )

Triterpenoid saponins

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 (C 40 )

Higher terpenoids

Further reading

6. Alkaloids

Alkaloids derived from ornithine

Polyamines

Pyrrolidine and tropane alkaloids

Pyrrolizidine alkaloids

Alkaloids derived from lysine

Piperidine alkaloids

Quinolizidine alkaloids

Indolizidine alkaloids

Alkaloids derived from nicotinic acid

Pyridine alkaloids

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 b-carboline alkaloids

Terpenoid indole alkaloids

Quinoline alkaloids

Pyrroloindole alkaloids

Ergot alkaloids

Alkaloids derived from anthranilic acid

Quinazoline alkaloids

Quinoline and acridine alkaloids

Alkaloids derived from histidine

Imidazole alkaloids

Alkaloids derived by amination reactions

Acetate-derived alkaloids

Phenylalanine-derived alkaloids

Terpenoid alkaloids

Steroidal alkaloids

Purine alkaloids

Caffeine

Saxitoxin and tetrodotoxin

Further reading

7. Peptides, proteins, and other amino acid derivatives

Peptides and proteins

Ribosomal peptide biosynthesis

Peptide hormones

Thyroid hormones

Hypothalamic hormones

Anterior pituitary hormones

Posterior pituitary hormones

Pancreatic hormones

Interferons

Opioid peptides

Ribosomal peptide toxins

Enzymes

Non-ribosomal peptide biosynthesis

Modified peptides: penicillins, cephalosporins, and other b-lactams

Penicillins

Cephalosporins

Other b-lactams

Cyanogenic glycosides

Glucosinolates

Cysteine sulfoxides

Further reading

8. Carbohydrates

Monosaccharides

Oligosaccharides

Polysaccharides

Aminosugars and aminoglycosides

Further reading

Index