Selected Topics in the Chemistry of Natural Products

Contents......Page 8
Preface......Page 10
Acknowledgments......Page 12
Contributors......Page 14
1.1 INTRODUCTION......Page 22
1.2 HUMAN MEDICINAL AGENTS FROM PLANTS......Page 23
1.3 RECENT PROGRESS IN THE CHEMISTRY OF NATURAL PRODUCTS3,4,5......Page 25
1.4 THE CLASSIFICATION OF NATURAL PRODUCTS......Page 26
1.5 IDENTIFICATION OF NATURAL PRODUCTS BY CHROMATOGRAPHIC AND SPECTROSCOPIC METHODS......Page 29
REFERENCES......Page 30
2.1 INTRODUCTION......Page 32
2.2 PLANT NATURAL COMPOUNDS AND DRUG DISCOVERY......Page 33
2.3 EXAMPLES OF NATURALLY OCCURRING DRUGS OBTAINED FROM PLANTS......Page 36
2.4 EXAMPLES OF SEMISYNTHETIC DRUGS BASED ON LEAD COMPOUNDS FROM PLANTS......Page 42
2.5 PLANT-DERIVED COMPOUNDS USED AS “BIOCHEMICAL TOOLS”/“PHARMACOLOGICAL PROBES”......Page 49
2.6 STRATEGIES FOR MEDICINAL PLANT CONSERVATION......Page 53
2.7 BIOTECHNOLOGY / DIRECTED BIOSYNTHESIS ASPECTS......Page 55
2.8 FUTURE PROSPECTS......Page 58
REFERENCES......Page 60
3.1 CANNABIS PLANT HISTORY......Page 70
3.2.1 Biogenesis......Page 73
3.2.2 Cannabinoid Substances from Cannabis sativa L......Page 76
3.2.3 Non Cannabinoid Constituents of Cannabis sativa L......Page 77
3.3.1 Central (CB1) and Peripheral (CB2) Cannabinoid Receptors......Page 78
3.3.2 GPR55 Receptor......Page 79
3.4 ENDOCANNABINOIDS......Page 80
3.5 THE ENDOCANNABINOID CONGENERS......Page 84
REFERENCES......Page 87
4.1.1 Definitions......Page 98
4.1.2 Glossary......Page 99
4.1.3 Historical and New Horizons......Page 100
4.1.4.2 Terpenoids......Page 101
4.2.1.1 Extraction and Fractionation......Page 107
4.2.1.2 Instrumental Analyses......Page 108
4.3 NATURAL PRODUCTS AS TRACERS......Page 110
4.3.1.1 Tocopherols......Page 111
4.3.1.2 Biomass Burning......Page 115
4.3.1.3 Saccharides......Page 119
4.3.1.4 Photochemistry......Page 121
4.3.1.6 Natural Products in Fossils and Amber......Page 123
4.3.1.7 Hydrothermal Petroleum/Bitumen......Page 124
4.4 PROGNOSIS......Page 131
REFERENCES......Page 133
5.1.1 Dinoflagellates......Page 148
5.1.2 Porifera......Page 149
5.1.3 Cnidaria......Page 151
5.1.4 Mollusca......Page 152
5.1.5 Echinodermata......Page 154
5.2.1 Tetrodotoxin (TTX)......Page 156
5.2.2 Saxitoxin (STX)......Page 158
5.2.3 Ciguatoxin (CTX)......Page 159
5.2.4 Maitotoxin......Page 160
5.2.5 Okadaic acid (OA)......Page 161
5.2.6 Metabolites of Cyanobacteria......Page 162
5.2.7 Palytoxin (PTX)......Page 164
5.2.8 Conotoxins......Page 165
5.2.9 Ziconotide......Page 166
5.2.10 Sponge, Soft Coral and Tunicate Toxins......Page 167
REFERENCES......Page 169
6.1 INTRODUCTION......Page 176
6.2 OLFACTORIAL PROPERTIES OF CHIRAL OXYGENATED MONOTERPENES......Page 178
6.3 CHIRAL- GC DETERMINATION OF ENANTIOMERIC COMPOSITION OF OXYGENATED MONOTERPENES......Page 179
6.4.1 Piperitone......Page 184
6.4.2 Pulegone......Page 185
6.4.3 Menthone and Isomenthone......Page 186
6.4.4 Verbenone......Page 187
6.4.6 Fenchone......Page 188
6.4.7 Camphor......Page 189
6.4.8 cis- and trans-Piperitone Oxide......Page 190
6.4.10 Linalool......Page 191
6.4.12 Citronellol......Page 192
6.4.14 α-Terpineol......Page 193
6.4.15 Terpinen-4-ol......Page 194
REFERENCES......Page 195
7.1 INTRODUCTION......Page 210
7.2.2 Stevia rebaudiana bertoni......Page 211
7.3 SWEET PROTEINS......Page 213
7.3.1 Brazzein......Page 214
7.3.2 Thaumatin......Page 217
7.3.3 Safety evaluation of thaumatin (Talin protein)......Page 219
7.3.4 Monellin......Page 220
7.3.5 Curculin......Page 221
7.3.6 Mabinlin......Page 222
7.3.7 Pentadin......Page 223
7.3.8 Miraculin......Page 225
REFERENCES......Page 227
8.2 ALGICIDES......Page 230
8.3.1 Insect Repellents......Page 235
8.3.2 Insecticidal Natural Products......Page 239
8.3.3 Molluscicides......Page 246
8.4.1 Compounds that Induce Resistance to Pathogens in Plants......Page 250
8.4.2 Compounds that Act Directly on Pathogens......Page 251
8.5 VERTEBRATE PESTS......Page 256
8.6.1 The Use of Natural Products inWeed Management......Page 257
8.6.2 Natural Product Herbicides......Page 258
8.6.3 Natural Products as Lead Compounds for Conventional Herbicides......Page 261
8.7 CONCLUSIONS......Page 263
REFERENCES......Page 264
9.1 NATURAL PRODUCTS FROM MICROORGANISMS: CURRENT STATUS......Page 274
9.2 COMPLEXITYOFMYCELIALMICROORGANISMS......Page 276
9.3 MORPHOLOGY OF FILAMENTOUS MICROORGANISMS IN INDUSTRIAL HABITAT......Page 279
9.4 THE UNITY OF LIVING MATTER......Page 282
9.5 MICROBIAL ADHESION: FLOCCULATION AND BIOFILM FORMATION......Page 283
9.6 AERIAL MYCELIUM......Page 286
9.7 QUORUM SENSING......Page 288
9.8 APOPTOSIS......Page 290
9.9 STRINGENT RESPONSE......Page 292
9.10 CELL DIVISION GENES......Page 293
9.11 GENES OF FUNGAL MORPHOLOGY......Page 295
9.12 RECIPES FOR THE FUTURE......Page 297
REFERENCES......Page 299
10.1 INTRODUCTION......Page 306
10.2.1 Coleoptera......Page 308
10.2.3 Diptera......Page 312
10.2.4 Hemiptera......Page 313
10.2.6 Homoptera......Page 314
10.2.7 Hymenoptera......Page 315
10.2.9 Lepidoptera......Page 318
10.2.11 Thysanoptera......Page 328
10.2.14 Some Other Interesting Examples......Page 329
10.3 SYNTHESIS OF PHEROMONES......Page 330
REFERENCES......Page 359
11.1 INTRODUCTION......Page 372
11.2 CELLWALL ANTIBIOTICS......Page 374
11.2.1 Beta-Lactams......Page 376
11.2.3 Cephalosporins......Page 379
11.2.5 Bacitracin......Page 380
11.3 CELL MEMBRANE INHIBITORS......Page 381
11.4 PROTEIN BIOSYNTHESIS INHIBITORS......Page 382
11.4.1 Aminoglycosides......Page 384
11.5.2 Rifampin......Page 386
11.6 FATTY ACID BIOSYNTHESIS INHIBITION......Page 387
11.6.1 Screening for FabH/F Inhibitors......Page 389
11.7 LESSONS LEARNED FROM ANTIBIOTIC DISCOVERY......Page 390
11.8 PROSPECTS OF IDENTIFYING NOVEL ANTIBIOTICS......Page 392
REFERENCES......Page 393
12.1 INTRODUCTION......Page 398
12.2.1 Introduction......Page 400
12.2.2.2 L-DOPA (refer to Structures 1)......Page 401
12.2.2.3 Other phenylpropylamines (refer to Structures 1)......Page 403
12.2.2.4 Ergot alkaloids and derivatives (refer to Structures 2)......Page 404
12.2.2.5 Other dopaminergic compounds (refer to Structures 3)......Page 406
12.2.2.6 PD: Monoamine oxidase inhibitors (refer to Structures 4 and 5)......Page 408
12.3.1 Introduction......Page 411
12.3.2.1 Introduction (refer to Structures 6)......Page 412
12.3.2.3 Pilocarpine......Page 413
12.3.3.1 Introduction......Page 414
12.3.3.2 Physostigmine and related compounds (refer to Structures 7)......Page 415
12.3.3.3 Galantamine and other amaryllidaceae alkaloids (refer to Structures 8)......Page 418
12.3.3.4 Huperzine A and analogues (refer to Structures 8 and 9)......Page 419
12.3.3.5 Other alkaloids (refer to Structures 9–13)......Page 421
12.3.3.6 Terpenoids (refer to Structures 13–15)......Page 427
12.3.3.7 Phenolic compounds and others derived from the Shikimic pathway (refer to Structures 15–17)......Page 429
12.3.3.8 AD: Use of nicotinergic compounds (refer to Structures 18)......Page 434
12.3.3.9 AD: Approaches related to improved blood .ow through the brain (refer to Structures 18)......Page 435
12.4 MULTIPLE SCLEROSIS (MS) (refer to Structures 19)......Page 436
12.5 CONCLUSIONS......Page 437
REFERENCES......Page 438
13.1 INTRODUCTION......Page 448
13.2.1 Flourensia cernua......Page 451
13.2.2 Prionosciadium watsoni......Page 453
13.2.3 Maxillaria densa and Epidendrum rigidum......Page 455
13.2.4 Hofmeisteria schaffneri......Page 461
13.3.1 Phoma herbarum......Page 464
13.3.2 Guanomyces polytrhix......Page 473
13.3.3 Malbranchea aurantiaca......Page 477
13.4 CONCLUSIONS......Page 485
REFERENCES......Page 486
14.1 INTRODUCTION......Page 492
14.2 NATURAL PRODUCT-BASED ANTICANCER DRUGS......Page 493
14.3 PLANT-ASSOCIATED FUNGI AS A SOURCE OF BIOACTIVE COMPOUNDS......Page 494
14.4.1 Paclitaxel (Taxol®)......Page 496
14.4.2 Podophyllotoxin......Page 497
14.4.3 Camptothecin......Page 498
14.4.4 Radicicol......Page 499
14.5.1 Globosumones from Chaetomium globosum......Page 501
14.5.2 (+)-Epiepoxydon from Apiospora montagnei......Page 502
14.5.4 Curvularins from a Penicillum sp. and Nectria galligens......Page 503
14.5.6 11-Hydroxycurvularin and Penicillic Acid from Aspergillus sp.......Page 505
14.5.7 Terricyclic Acid A (TCA) from Aspergillus terreus......Page 507
14.5.8 Brefeldin A from Aspergillus clavatus and Paecilomyces sp......Page 508
14.5.9 Rubrofusarin B from Aspergillus niger......Page 509
14.5.11 Peniprequinolone from Penicillium janczewskii......Page 510
14.5.13 Cytoskyrin A from Cytospora sp. CR200......Page 511
14.6 APOPTOTIC AGENTS......Page 512
14.6.1 Hormonemate from Hormonema dematioides......Page 513
14.7.1 Microcarpalide I from an Unidenti.ed Endophytic Fungus......Page 514
14.7.2 Cytochalasins from Rhinocladiella sp......Page 515
14.8 ACKNOWLEDGMENTS......Page 516
REFERENCES......Page 517
15.1 INTRODUCTION......Page 524
15.2.1 Endophytes......Page 525
15.2.2 Mycorrhizae......Page 527
15.2.3 Fungal Morphology and Endophyte Terminology......Page 530
15.2.4 Taxonomy and Molecular Biology......Page 532
15.2.5 Transmission of Endophytes......Page 535
15.2.6 Diversity of Endophytes......Page 536
15.3.1 Gymnosperms and Primitive Plants......Page 538
15.3.2 Secondary Metabolites from Mycorrhizal Fungi......Page 560
15.3.3 Dicotyledonous plant endophyte products......Page 564
15.3.4 Monocotyledonous Plant Endophyte Products......Page 578
15.3.5 Gene Transfer......Page 582
15.4 CONCLUSIONS......Page 584
REFERENCES......Page 585
Index......Page 602