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x
Contents
Disaccharides of Pharmaceutical Importance 49
Sucrose 49
Lactose 53
Maltose 55
Trehalose 59
Trisaccharides 60
Gentianose 60
Tetrasaccharides 61
Stachyose 61
Polysaccharides 62
Classifi cation and Nomenclature of Polysaccharides 62
Polysaccharides of Pharmaceutical Importance 63
Starch 63
Chapter 3 Glycosides 73
Introduction 73
Classifi cation of Glycosides 74
Qualitative Chemical Tests for Glycosides 80
Isolation of Glycosides 81
Structural Determination of Glycosides 82
Glycosides of Pharmaceutical Importance 83
Salicin 83
Ruberythric acid 84
Arbutin 86
Sinigrin 88
Amygdalin 89
Chapter 4 Amino Acids, Peptides and Proteins 93
Amino Acids 93
Nomenclature of Amino Acids 94
Qualitative Chemical Tests for Amino Acids 94
Classifi cation of Amino Acids 95
Isolation and Separation of Amino Acids from Proteins 96
Synthesis of Amino Acids 97
General Physical and Chemical Properties of Amino Acids 102
Peptides 110
Classifi cation of Peptides 111
Synthesis of Peptides 111
General Principles of Peptide Synthesis 112
General Methods of Peptide Synthesis 115
Structure of Peptides 117
N-Terminal (Amino-end) degradation 118
C-Terminal (Carboxyl-end) degradation 120
Proteins 122
Biological Functions 122
Classifi cation of Proteins 122
Contents
xi
Qualitative Chemical Tests for Proteins 124
Structure of Proteins 125
Proteins of Pharmaceutical Importance 132
Glutathione 132
Oxytocin 135
Thyroxine 138
Insulin 142
Chapter 5 Alkaloids 149
Introduction 149
Nomenclature of Alkaloids 150
Classifi cation of Alkaloids 150
Qualitative Chemical Tests for Alkaloids 158
Isolation or Production of Alkaloids 159
Determination of Molecular Structure of Alkaloids: General Methods 160
Molecular Formula Determination 160
Hydrolysis 160
Determination of Unsaturation 160
Functional Group Determination 160
Degradation of Alkaloids 164
Physical Methods in Conjunction with Chemical Methods 169
Synthesis 170
Alkaloids of Pharmaceutical Importance 170
Atropine 172
Morphine 177
Quinine 186
Papaverine 194
Emetine 199
Ephedrine 205
Ergotamine 207
Reserpine 214
Strychnine 222
Colchicine 232
Piperine 238
Nicotine 240
Chapter 6 Steroids and Hormones 249
Steroids 249
Nomenclature of Steroids 251
Stereochemistry 253
Qualitative Chemical Tests for Steroids 254
Sterols 254
Cholesterol 255
Lanosterol 256
Stigmasterol 257
Ergosterol 257
xii
Contents
Miscellaneous Sterols 258
Structural Elucidation of Cholesterol 258
Bile acids 268
5 β-Cholanic Acid 270
5
α-Cholanic Acid 271
Functions of Bile Acids 271
Saponins and Sapogenins 272
Steroidal Saponins 272
Synthesis of Diosgenin 274
Pentacyclic Triterpenoid Saponins 276
Steroidal Alkaloids 277
Cardiac Steroids or Cardiotonic Glycosides 278
Hormones 282
Classifi cation 283
Sex Hormones 283
Biosynthesis of Sex Steroid Hormones 284
Androgens (Male Sex Hormones) 285
Biological Activities of Androgens 285
Therapeutic Uses of Anabolic Androgenic Steroids 286
Androgens of Pharmaceutical Importance 286
Androgesterone 286
Dehydroepiandrosterone 288
Testosterone 289
Methyl Testosterone 292
Fluoxymesterone 292
SAR of Androgens 293
Oestrogens 295
Isolation of Oestrogens 296
Biological Activities of Oestrogens 296
Metabolism of Oestrogens 297
Therapeutic Uses of Oestrogens 297
Classifi cation of Oestrogens 298
Oestrogens of Pharmaceutical Importance 300
Oestrone 300
Oestriol 301
Oestradiol 303
17 α-Ethinyloestradiol 305
Chemical Relationship Between Oestrone, Oestriol and Oestradiol 306
Nonsteroidal Oestrogens or Artifi cial Hormones 308
Stilboesterol 308
Hexoestrol 310
Dienoestrol 310
Benzoestrol 312
Structure–Activity Relationship (SAR) of Oestrogens 313
Corpus Luteum Hormones or Gestogens or Progestins 315
Metabolism of Progesterone 316
Contents
xiii
Biological Activities of Progestins 316
Therapeutic Uses of Progestins 316
Classifi cation of Progesterones 317
Progestins of Pharmaceutical Importance 318
Progesterone 318
Progesterone derivatives 322
Structure–Activity Relationship (SAR) of Progesterones 324
Hormonal Contraceptives 326
Oral Contraceptives 326
Corticosteroids (Adrenal Cortical Hormones) 327
Biological Effects of Glucocorticoids 327
Biosynthesis of the Adrenocorticoids from Cholesterol 328
Therapeutic Uses of Glucocorticoids 329
Classifi cation of Corticosteroids 330
Corticosteroids of Pharmaceutical Importance 333
Cortisone 333
Cortisol (or) Hydrocortisone 334
Aldosterone 337
Prednisolone 338
Dexamethasone 340
SAR of Corticosteroids 341
Chapter 7 Terpenoids 349
Introduction 349
Isolation of Terpenoids 352
Classifi cation of Terpenoids 353
Isoprene Rule and Special Isoprene Rule 361
General Methods for the Elucidation of Structure of Terpenoids 363
Hemiterpenoids 366
Monoterpenoids or Terpenes 367
Acyclic Monoterpenoids 367
Citral 367
Citronellal 371
Citronellol 373
Geraniol 374
Nerol 376
Linalool 377
Myrcene 378
Ocimene 378
Lavundulol 378
Cyclization Reactions of Acyclic Monoterpenoids 379
Monocyclic Monoterpenoids 381
Limonene 381
α -Terpineol 384
1,8-cineol 389
Menthol and Menthone 390
xiv
Contents
Pulegone 392
Carvone 393
Ionones 397
Bicyclic Monoterpenoids 399
α -Pinene 399
Camphor 404
Borneol and Isoborneol 409
Camphene 410
Fenchone 410
Sesquiterpenoids 410
Acyclic Sesquiterpenoids 410
Farnesol 411
Monocyclic Sesquiterpenoids 413
Zingiberene 414
Bicyclic Sesquiterpenoids 417
Cadinene 417
Miscellaneous Sesquiterpenoids 418
Artimisinin 418
Gossypol and related compounds 418
Diterpenoids 419
Phytol 419
Vitamin A 419
Abietic Acid 420
Ginkolides 420
Taxol 420
Triterpenoids 421
Squalene 421
Lanosterol and Euphol 422
Amyrins 422
Tetraterpenoids 422
Polyterpenoids 423
Chapter 8 Flavonoids 427
Introduction 427
Isolation of Flavones 428
Structural Elucidation of Flavones 429
Flavonol 431
Structural Elucidation of Flavonol 432
Quercetin 434
Structural Elucidation of Quercetin 434
Isofl avones 437
Structural Elucidation of Isofl avones 438
Chapter 9 Vitamins 441
Introduction 441
Contents
xv
Nomenclature of Vitamins 442
Classifi cation of Vitamins 443
Sources of Vitamins and Their Defi ciency Diseases 445
Vitamin A 446
Vitamin D 463
Vitamin E (Tocopherols) 474
Vitamin K 490
Vitamin B Complex 503
Vitamin B 1 503
Vitamin B
2 514
Vitamin B
3 526
Vitamin B
5 533
Vitamin B
9 or Vitamin Bc or Folic Acid 540
Vitamin B
6 or Pyridoxine 548
Vitamin B
12 (Cyanocobalamin) 560
Vitamin C (Ascorbic Acid) 571
Vitamin-Like Compounds 588
PABA 588
Choline 588
Carnitine 589
Lipoic Acid or Vitamin Bt 590
Chapter 10 Antibiotics 593
Introduction 593
Historical Background 594
Spectrum of Activity of Chemotherapeutic Agents 594
Classifi cation Based on Mechanism of Action 596
Classifi cation Based on Chemical Structure 597
Penicillins 597
Introduction 597
Nomenclature 598
Production of Penicillins 598
Isolation of Penicillins 599
Chemical Degradation of Penicillins 600
Structural Elucidation of Penicillins 601
Classifi cation 606
Structure–Activity Relationship (SAR) of Penicillins 610
Cephalosporins 611
Introduction 611
Nomenclature 612
Degradation of Cephalosporins 613
Structural Elucidation of Cephalosporins 614
Classifi cation of Cephalosporins 619
Adverse Effects of Cephalosporins 623
Uses of Cephalosporins 623
SAR of Cephalosporins 623
xvi
Contents
Aminoglycoside antibiotics 625
Introduction 625
Production of Streptomycin 625
Isolation of Streptomycin 626
Streptomycin and Dihydrostreptomycin 626
Structural Elucidation of Streptomycin 627
Gentamycins 633
Neomycin 633
Kanamycin 634
Amikacin 635
Tobramycin 635
Netilmicin 636
SAR of Aminoglycoside Antibiotics 636
Tetracyclines 637
Introduction 637
Classifi cation of Tetracyclines 638
Structural Elucidation of Oxytetracycline 640
SAR of Tetracyclines 647
Chloramphenicol or Chloromycetin 649
Introduction 649
Structural Elucidation of Chloramphenicol 650
SAR of Chloramphenicol 653
Polypeptide antibiotics 654
Introduction 654
Bacitracin 654
Polymyxin 655
Lincomycins 655
Chapter 11 Purines, Pyrimidines and Nucleic Acids 659
Introduction 659
Purines 659
Classifi cation of Purines 660
Purine 661
Adenine 664
Guanine 666
Uric Acid 667
Xanthine 673
Methylxanthines 674
Caffeine 675
Theobromine 678
Theophylline 680
Hypoxanthine 682
Relationship Between Uric Acid and Xanthine Bases 683
Pyrimidines 684
Uracil 684
Thymine 686
Cytosine 687
Contents
xvii
5-Methyl Cytosine 688
5-Hydroxy Methyl Cytosine 689
NUCLEIC ACIDS 690
Classifi cation of Nucleic Acids 690
Functions of Nucleic Acids 691
Components of Nucleic Acids 691
Nucleosides 692
Nucleotides 694
Structural Elucidation of Nucleic Acids 696
Internucleotide Bond in RNA 713
Internucleotide Bond in DNA 714
Structure of DNA 715
Structure of RNA 719
Types of RNA 720
Differences Between DNA and RNA 722
Chapter 12 Enzymes 725
Introduction 725
Nomenclature and Classifi cation of Enzymes 726
Oxidoreductase 727
Transferase 727
Hydrolase 728
Lyase 728
Isomerase 728
Ligase 729
Qualitative Chemical Tests for Enzymes 729
Chemical Nature of Enzymes 730
Effi ciency of Enzymes 730
Specifi city of Enzymes 731
Stereospecifi city or Optical Specifi city 731
Reaction Specifi city 732
Substrate Specifi city 732
Theories of Enzyme Action 732
Lock and Key Model 733
Induced Fit Theory 733
Substrate Strain Theory 734
Mechanism of Enzyme Action 734
Coenzymes 735
Enzymatic Catalysis 738
Catalysis by Proximity and Orientation 738
Acid–Base Catalysis 738
Catalysis by Strain 739
Covalent Catalysis 739
Enzyme Inhibition 740
Reversible Inhibition 741
Irreversible Inhibition 743
xviii
Contents
Chapter 13 Lipids 745
Introduction 745
Classifi cation of Lipids 746
Simple Lipids (Fats and Oils) 747
Differences Between Fats and Oils 747
Nomenclature of Fats 748
Extraction of Fats 749
Physical and Chemical Properties of Fats and Oils 749
Analysis of Oils and Fats 751
Fatty Acids 754
Nomenclature of Fatty Acids 754
Classifi cation of Fatty Acids 755
Waxes 757
Common Waxes 757
Compound Lipids/Complex Lipids 758
Lecithins 758
Cephalins 759
Plasmalogens 759
Sphingomyelins 760
Glycolipids, Galactolipids and Cerebrosides 760
Derived Lipids 761
Sterols 762
Cholesterol 762
Lanosterol 762
Stigmasterol 763
Ergosterol 763
Index 765
INTRODUCTION
For thousands of years, natural products (drugs and pharmaceutical substances obtained from
natural origin) have played vital role in treating and preventing human diseases. Humans always
have been interested in naturally occurring compounds from prebiotic, microbial, plant and
animal sources. In earlier period of treatment, naturally obtained ingredients were believed to be
combined with witchcraft or mysticism. Later these treatments were found effective and the results
were documented in the development of early herbal medicine. The science of pharmacognosy (a
branch of pharmaceutical science), which deals with the naturally obtained drugs, developed from
these records to provide an authentic, scientifi c description of the natural products used in treating
and preventing human ailments.
The term Pharmacognosy was coined by a German scientist from two Greek words pharmakon
(means a drug) and gignosco (means to acquire the knowledge of), in the year 1815. Pharmacognosy
is defi ned as the ‘study of the physical, chemical, biochemical and biological properties of medicinal
products obtained from our living environment as well as the search for new drugs from natural
sources’.
Pharmacognosy is an established basic pharmaceutical science, which has changed
considerably from being largely descriptive botanical and mycological fi eld to having more
of chemical and biological focus. It serves as an important linkage between basic biology and
medicinal chemistry. The advent of phytochemistry and pharmacological screening programme
(heart of the drug discovery process from crude extracts) helps the natural products to fi nd
their way into medicine as purifi ed phytochemicals, rather than in the form of conventional
preparations.
Chemistry of Natural Products is a branch of chemistry that deals with the isolation, identifi cation,
structure elucidation and study of the chemical characteristics of chemical substances produced
by living matters. The study of pharmaceutical applications of these natural products led to the
establishment of a new avenue called Pharmaceutical Chemistry of Natural Products.
Introduction to Pharmaceutical
Chemistry of Natural Products
1
CHAPTER