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Chemistry of natural products / Sujata V. Bhat, Bhimsen A. Nagasampagi, Meenaskshi Sivakumar. — Berlin ; New York : New Delhi : Springer ; Narosa, c2006.—(54.57/B575) |
Contents
Contents
General Introduction 1
CHAPTER 1: STEROIDS 15
1.1 Introduction 15
1.2 Nomenclature and Stereochemistry 15
1.3 Biogenesis 21
1.4 Physical Methods of Characterization 24
1.5 Sterols 28
1.6 Cholesterol 29
1.7 Other C-27 Sterols 44
1.8 C-28 Sterols-Ergosterol 44
1.9 C-29 Sterols 46
1.10 C-30 Sterols 47
1.11 Vitamin D Group 49
1.12 Bile Acids 50
1.13 Bile Alcohols 57
1.14 Sex Hormones 58
1.15 Estrogens 58
1.16 Estrone 61
1.17 Estradiol 70
1.18 Estriol 71
1.19 Equine Estrogens 72
1.20 Synthetic Estrogen Analogues 73
1.21 Gestogens- Progesterone 74
1.22 Oral Contraceptives 81
1.23 Commercial Significance of 16-Dehydropregnenolone Acetate (16-DPA， 1.259)， 82
1.24 Androgens 82
1.25 Testosterone 85
1.26 Dehydroepiandrosterone 89
1.27 Androsterone 90
1.28 Anabolic Steroids 91
1.29 Adrenocortical Hormones 91
1.30 Cortisone 93
1.31 Cortisol 98
1.32 Aldosterone 99
1.33 Steroids from Plants 102
1.34 Cardiac Glycosides 103
1.35 Cardenolides 103
1.36 Bufadienolides 106
1.37 Sapogenins 108
1.38 Steroidal Alkaloids 110
1.39. Steroids from Insects 114
CHAPTER 2: TERPENOIDS 115
2.1 Introduction 115
2.2 Classification 115
2.3 Biosynthesis 116
2.4 Occurrence 120
2.5 Isolation and Separation Techniques 125
2.6 Chromatographic Methods 127
2.7 Structure Elucidation 131
2.8 Monoterpenoids 139
2.9 Sesquiterpenoids 155
2.10 DiterPenoids 182
2.11 Triterpenoids 196
2.12 Carotenes 200
CHAPTER 3 FATTY LIPIDS AND PROSTAGLANDINS
Section A: Fatty Lipids 206
3.1 Introduction 206
3.2 Occurrence of Triacylglycerols 206
3.3 Fatty Acids 207
3.4 Waxes 210
3.5 Identification and Extraction of Lipids 210
3.6 Reactions of Fatty Acids 211
3.7 Commercial uses of Oils， Fats and Waxes 212
3.8 Soaps and Micelle 212
3.9 Biosynthesis of Fatty Acids and Triglycerides 213
3.10 Membrane Lipids 213
3.11 Plasma Membranes 219
3.12 Large Ring Lactones 220
Section B: Prostaglandins 221
3.13 Introduction 221
3.14 Occurrence 221
3.15 Isolation 222
3.16 Biogenesis and Metabolism 222
3.17 Clinical Significance 223
3.18 Nomenclature and Stereochemistry 224
3.19 Structure Elucidation 227
3.20 Total Synthesis 229
CHAPTER 4 ALKALOIDS
4.1 Introduction 237
4.2 Occurrence 238
4.3 Function of Alkaloids in Plants 241
4.4 Classification 241
4.5 Nomenclature 242
4.6 Pharmaceutical Applications 242
4.7 Isolation 244
4.8 Qualitative Tests and General Properties 244
4.9 General Methods of Structure Determination 245
4.10 Benzylisoquinoline and Related Alkaloids 252
4.11 Morphine 258
4.12 Quinoline Alkaloids 264
4.13 Indole Alkaloids 268
4.14 Reserpine 269
4.15 Ergot Alkaloids 276
4.16 Strychnine 281
4.17 The Diterpene Alkaloids 284
4.18 Pyridine Alkaloids of Tobacco 291
4.19.Tropane Alkaloids 292
4.20 Alkaloid Amines (Psuedoalkaloids) 301
4.21 Adrenaline (Epinephrine) 304
4.22 Piperine 306
4.23 Colchicine 308
4.24 Purine Bases 311
CHAPTER 5: AMINO ACIDS， PROTEINS AND BIOCONVERSIONS
5.1 Introduction 317
5.2 α-Amino Acids 318
5.3 Laboratory Synthesis of or-Amino Acids 325
5.4 Industrial Production of Amino Acids 327
5.5 Reactions of or-Amino Acids 330
5.6 Polypeptides 333
5.7 Functions of Peptides 335
5.8 Proteins 338
5.9 Primary Structure of Peptides 339
5.10 Secondary， Tertiary and Quaternary Structures of Proteins 343
5.11 Enzymes 348
5.12 Immunoglobulins and Plasma Proteins 369
5.13 Structural Proteins 372
5.14 Laboratory Synthesis of Polypeptides 379
5.15 Biosynthesis
5.16 Production of Organic Chemicals Through Fermentation 389
CHAPTER 6: NUCLEIC ACIDS
6.1 Introduction 394
6.2 Basic Structure 394
6.3 Deoxyribonucleic Acids (DNA) 398
6.4 Reactions of Nucleic Acid Bases 405
6.5 Mutations 407
6.6 DNA Replication 410
6.7 Sequence Analysis of DNA 412
6.8 Chromosomes and Extra-Chromosomal DNA 413
6.9 Genetic Code 415
6.10 Ribonucleic Acids 416
6.11 Translation 423
6.12 Other Functions of Nucleotides 425
6.13 Viruses 432
6.14 Ribozymes (RNA Enzymes) 433
6.15 Microbial Production of Nucleosides， Nucleotides and Related Com
6.16 Laboratory Synthesis of Nucleic Acid Bases and Nucleosides 436
6.17 Synthesis of Nucleic Acid Sequences 444
6.18 Biosynthesis of Bases and Nucleosides 448
6.19 Recombinant DNA Technology 453
CHAPTER 7: CARBOHYDRATES
7.1 Introduction 458
7.2 Classification 458
7.3 Nomenclature 459
7.4 Monosaccharides 459
7.5 Carboxylic Acids 492
7.6 Deoxysugars 493
7.7 Dihydrosugars 494
7.8 Cyclitols 496
7.9 Aminosugars 496
7.10 Anhydrosugars 497
7.11 Disaccharides 498
7.12 Trisaccharides 506
7.13 Polysaccharides 509
7.14 Mucopolysaccharides 523
7.15 Proteoglycans 525
7.16 Glycoproteins and Glycolipids 525
7.17 Separation of Carbohydrates 526
CHAPTER 8: INSECT AND PLANT GROWTH REGULATORS
Section A: Insect Secretions and Control Agents 536
8.1 Hormones of Endocrine Organs 536
8.2 The Exocrine Secretions 540
8.3 Insect Control with Pyrethrins and Synthetic Analogues 548
8.4 Insect Control with Antifeedants 552
Section B: Plant Growth Regulators 554
8.5 Naturally Occurring Plant Hormones 554
8.6 Gibberellins (GAs) 559
8.7 Cytokinins 567
8.8 Brassinosteroids 570
8.9 Ethylene 576
8.10 Abscisic Acid (ABA) 577
8.11 Jasmonic Acid 581
CHAPTER 9: PHENOLICS， NATURAL DYES AND PIGMENTS
Section A: Flavonoids and Coumarins 585
9.1 Classification 585
9.2 Biogenesis 587
9.3 Occurrence 591
9.4 Isolation and Separation 591
9.5 Separation Techniques 592
9.6 Structure Elucidation 593
9.7 Total Synthesis 599
9.8 Anthocyanidins and Related Phenolic Molecules 602
9.9 Tannins 605
9.10 Simple Phenolic Compounds 610
9.11 Coumarins 613
Section B: Natural Dyes 619
9.12 Introduction 619
9.13 Classification 619
9.14 Flavonoids 620
9.15 Xanthones 622
9.16 Quinonoids 622
9.17 Polyenes 627
9.18 Isolation of Annatto Dye 629
9.19 Organic Nitrogenous Dyes 631
9.20 Chlorophyll 639
9.21 Haemoglobin 647
9.22 Nitrogen Heteocyclic Organic Dyes 651
9.23 Insect Dyes 654
9.24 Mineral Pigments 654
9.25 Application of Dyes 654
9.26 Methods for Preparation of Some Dyes for Commercial Use 655
9.27 Standardization of the Dyes for Improving Colour Fastness 656
9.28 Metallocyanins 660
CHAPTER 10: MARINE NATURAL PRODUCTS
10.1 Introduction 662
10.2 Terpenoids 662
10.3 Carotenoids 669
10.4 Sterols 671
10.5 Moulting Hormones (Ecdysones) 674
10.6 Phloroglucinol Derivatives 674
10.7 Halogenated Compounds 676
10.8 Indole Derivatives 678
10.9 Adenochromes 678
10.10 Marine Toxins 681
10.11 Bioluminescence 681
10.12 Electrophysiological Studies 682
10.13 Cytokinin Activity of Seaweed Extracts 682
CHAPTER 11: ANTIBACTERIALS
11.1 Introduction 684
11.2 Historical Developments 685
11.3 Bacterial Cell 688
11.4 Search for New Antibiotics 690
11.5 Antibiotic Assay 692
11.6 Modes of Antibacterial Action 692
11.7 Modes of Resistance 695
11.8 Classification of Antibacterials 696
11.9 β-Lactams 696
11.10 Tetracyclines Structure 715
11.11 Macrolide Antibiotics 719
11.12 Polyenes 723
11.13 Rifamycins (Ansamycins) 724
11.14 Griseofulvin 727
11.15 Chloramphenicol (Chloromycetin) 729
11.16 Quinolone Antibacterials 733
11.17 Sulfonamides 736
11.18 Anthracyclines 742
11.19 Aminoglycosides 743
11.20 Polypeptide Antibiotics 748
11.21 Polyether Antibiotics 749
11.22 Miscellaneous Antibiotics 750
CHAPTER 12: VITAMINS
12.1 Introduction 756
12.2 Vitamin A 756
12.3 Vitamin D 761
12.4 Vitamin E 761
12.5 Vitamin K 764
12.6 Vitamin B Complex 768
12.7 Vitamin B1 768
12.8 Vitamin B2 772
12.9 Vitamin B6 (Pyridoxine， Adermine) 777
12.10 Vitamin B12 781
12.11 Niacin 783
12.12 Pantothenic Acid 785
12.13 Folic Acid 787
12.14 Vitamin C 788
12.15 Vitamin H 792
Appendix 797
Subject Index 823
