Medicinal Natural Products A Biosynthetic Approach

by Dewick, Paul M.

• ISBN13: 9780470741689
• ISBN10: 0470741686
• Edition: 3rd
• Format: Hardcover
• Copyright: 2009-03-09
• 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.

Author Biography

"The enthusiasm and communication skills of Paul Dewick are evident in his organization and writing...Medicinal Natural Products is a reference treasured and highly recommended by this reviewer." American Journal of Pharmaceutical Education

Table of Contents

About this book, and how to use it	p. 1
The subject	p. 1
The aim	p. 1
The approach	p. 2
The topics	p. 2
The figures	p. 2
Further reading	p. 3
What to study	p. 3
What to learn	p. 3
Nomenclature	p. 3
Conventions regarding acids, bases, and ions	p. 4
Some common abbreviations	p. 4
Further reading	p. 5
Secondary metabolism: the building blocks and construction mechanisms	p. 7
Primary and secondary metabolism	p. 7
The building blocks	p. 8
The construction mechanisms	p. 11
Alkylation reactions: nucleophilic substitution	p. 12
Alkylation reactions: electrophilic addition	p. 12
Wagner-Meerwein rearrangements	p. 15
Aldol and Claisen reactions	p. 15
Imine formation and the Mannich reaction	p. 18
Amino acids and transamination	p. 20
Decarboxylation reactions	p. 22
Oxidation and reduction reactions	p. 24
Dehydrogenases	p. 24
Oxidases	p. 26
Monooxygenases	p. 26
Dioxygenases	p. 26
Amine oxidases	p. 27
Baeyer-Villiger monooxygenases	p. 27
Phenolic oxidative coupling	p. 28
Halogenation reactions	p. 28
Glycosylation reactions	p. 31
Elucidating biosynthetic pathways	p. 34
Further reading	p. 38
The acetate pathway: fatty acids and polyketides	p. 39
Fatty acid synthase: saturated fatty acids	p. 39
Unsaturated fatty acids	p. 44
Uncommon fatty acids	p. 53
Prostaglandins	p. 58
Thromboxanes	p. 64
Leukotrienes	p. 64
Polyketide synthases: generalities	p. 66
Polyketide synthases: macrolides	p. 68
Polyketide synthases: linear polyketides and polyethers	p. 90
Diels-Alder cyclizations	p. 96
Polyketide synthases: aromatics	p. 96
Cyclizations	p. 99
Post-polyketide synthase modifications	p. 103
Starter groups	p. 116
Further reading	p. 131
The shikimate pathway: aromatic amino acids and phenylpropanoids	p. 137
Aromatic amino acids and simple benzoic acids	p. 137
Phenylpropanoids	p. 148
Cinnamic acids and esters	p. 148
Lignans and lignin	p. 152
Phenylpropenes	p. 156
Benzoic acids from C6C3 compounds	p. 157
Coumarins	p. 161
Aromatic polyketides	p. 166
Styrylpyrones, diarylheptanoids	p. 166
Flavonoids and stilbenes	p. 167
Flavonolignans	p. 173
Isoflavonoids	p. 174
Terpenoid quinones	p. 178
Further reading	p. 184
The mevalonate and methylerythritol phosphate pathways: terpenoids and steroids	p. 187
Mevalonic acid and methylerythritol phosphate	p. 188
Hemiterpenes (C5)	p. 192
Monoterpenes (C10)	p. 193
Irregular monoterpenes	p. 204
Iridoids (C10)	p. 206
Sesquiterpenes (C15)	p. 210
Diterpenes (C20)	p. 223
Sesterterpenes (C25)	p. 234
Triterpenes (C30)	p. 234
Triterpenoid saponins	p. 242
Steroids	p. 247
Stereochemistry and nomenclature	p. 247
Cholesterol	p. 248
Phytosterols	p. 251
Vitamin D	p. 256
Steroidal saponins	p. 259
Cardioactive glycosides	p. 265
Bile acids	p. 275
Adrenocortical hormones/corticosteroids	p. 277
Semi-synthesis of corticosteroids	p. 277
Progestogens	p. 287
Oestrogens	p. 290
Androgens	p. 296
Tetraterpenes (C40)	p. 298
Higher terpenoids	p. 306
Further reading	p. 306
Alkaloids	p. 311
Alkaloids derived from ornithine	p. 311
Polyamines	p. 311
Pyrrolidine and tropane alkaloids	p. 312
Pyrrolizidine alkaloids	p. 324
Alkaloids derived from lysine	p. 326
Piperidine alkaloids	p. 326
Quinolizidine alkaloids	p. 328
Indolizidine alkaloids	p. 330
Alkaloids derived from nicotinic acid	p. 331
Pyridine alkaloids	p. 331
Alkaloids derived from tyrosine	p. 336
Phenylethylamines and simple tetrahydroisoquinoline alkaloids	p. 336
Modified benzyltetrahydroisoquinoline alkaloids	p. 346
Phenethylisoquinoline alkaloids	p. 359
Terpenoid tetrahydroisoquinoline alkaloids	p. 363
Amaryllidaceae alkaloids	p. 365
Alkaloids derived from tryptophan	p. 366
Simple indole alkaloids	p. 366
Simple ß-carboline alkaloids	p. 369
Terpenoid indole alkaloids	p. 369
Quinoline alkaloids	p. 380
Pyrroloindole alkaloids	p. 385
Ergot alkaloids	p. 387
Alkaloids derived from anthranilic acid	p. 395
Quinazoline alkaloids	p. 395
Quinoline and acridine alkaloids	p. 396
Alkaloids derived from histidine	p. 398
Imidazole alkaloids	p. 398
Alkaloids derived by amination reactions	p. 400
Acetate-derived alkaloids	p. 401
Phenylalanine-derived alkaloids	p. 401
Terpenoid alkaloids	p. 406
Steroidal alkaloids	p. 406
Purine alkaloids	p. 413
Caffeine	p. 413
Saxitoxin and tetrodotoxin	p. 416
Further reading	p. 417
Peptides, proteins, and other amino acid derivatives	p. 421
Peptides and proteins	p. 421
Ribosomal peptide biosynthesis	p. 422
Peptide hormones	p. 426
Thyroid hormones	p. 426
Hypothalamic hormones	p. 427
Anterior pituitary hormones	p. 429
Posterior pituitary hormones	p. 430
Pancreatic hormones	p. 432
Interferons	p. 433
Opioid peptides	p. 434
Ribosomal peptide toxins	p. 434
Enzymes	p. 438
Non-ribosomal peptide biosynthesis	p. 438
Modified peptides: penicillins, cephalosporins, and other ß-lactams	p. 458
Penicillins	p. 458
Cephalosporins	p. 465
Other ß-lactams	p. 469
Cyanogenic glycosides	p. 476
Glucosinolates	p. 477
Cysteine sulfoxides	p. 480
Further reading	p. 481
Carbohydrates	p. 485
Monosaccharides	p. 485
Oligosaccharides	p. 490
Polysaccharides	p. 493
Aminosugars and aminoglycosides	p. 498
Further reading	p. 507
Index	p. 509
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