Comprehensive Natural Products II: Chemistry and Biology: Enzymes and Enzyme Mechanisms

1 CONAP_Contents_all_volumes......Page 1
Progress in Structure Elucidation......Page 13
Complexity of the Multicomponent Pheromone......Page 14
Progress in Unraveling the Stereochemical Aspects of Chemical Ecology......Page 15
Dual Roles of Semiochemicals as Pheromones and Kairomones......Page 16
New Trends in Mammalian Chemical Ecology......Page 17
References......Page 18
Plant Hormones......Page 20
Introduction......Page 23
Introduction......Page 24
Amino acid conjugates......Page 25
Ester conjugates......Page 26
Biosynthesis and Metabolism......Page 27
Indole-3-acetonitrile pathway......Page 28
Indole-3-acetaldehyde pathway......Page 29
Indole-3-acetaldoxime pathway......Page 30
Tryptamine pathway......Page 31
IAA synthase......Page 32
Transcriptional responses to auxin stimuli......Page 33
Introduction......Page 35
Fungal gibberellins......Page 36
Isolation and characterization......Page 37
Biosynthesis in plants......Page 38
Regulation of gibberellin levels in plants......Page 41
Biosynthesis in fungi......Page 42
Effects on shoot elongation......Page 43
Other effects......Page 44
GID1, the cytosolic gibberellin receptor......Page 45
DELLA protein, a key regulator of GA signaling......Page 47
Structures......Page 48
Cytokinin biosynthesis in higher plants......Page 51
Activation step of cytokinin biosynthesis......Page 53
trans-Hydroxylation of iP nucleotide for tZ biosynthesis......Page 54
O-glucosylation and O-xylosylation......Page 56
Degradation of cytokinins......Page 57
Translocation......Page 58
Control of shoot meristem activity......Page 59
Regulation of root formation......Page 60
Interactions between macronutrients and cytokinins......Page 61
Cytokinin receptor as a histidine protein kinase (His-kinase)......Page 62
Phosphotransfer proteins......Page 63
Introduction......Page 64
Isolation and analysis......Page 65
Physicochemical properties......Page 66
Functional groups essential for the activities......Page 69
Active conformation......Page 70
Biosynthesis in plants......Page 71
Biosynthesis in fungi......Page 73
Modification of the ring moiety......Page 74
Stomatal closure......Page 76
Receptors of ABA and ABA-related genes and proteins......Page 77
Introduction......Page 78
Analysis......Page 79
Structure-activity relationship......Page 81
Campestanol-dependent pathway......Page 83
Biosynthesis from 28-norcastasterone......Page 85
Physiology......Page 86
Signal transduction......Page 87
Introduction......Page 88
Chemical structure......Page 89
Synthesis of methyl epi-jasmonate......Page 90
Synthesis of OPDA, OPC-8:0, and related compounds......Page 92
Synthesis of tuberonic acid, 12-hydroxyjasmonic acid, and beta-glucopyranosyl derivatives......Page 93
Biosynthetic pathway in plants......Page 94
Responses to biotic and abiotic stresses......Page 95
Effect of jasmonates on developmental processes......Page 96
Signaling......Page 97
Biosynthesis......Page 98
Posttranslational regulation of ACC synthase......Page 99
Ethylene receptors......Page 100
EIN3......Page 101
Systemins......Page 102
AtPep1......Page 103
Phytosulfokine......Page 104
MCLV3 and CLE Peptides......Page 105
Remarks......Page 106
Strigolactones as rhizosphere signaling molecules......Page 107
A novel shoot branching inhibitor suggested by genetic studies......Page 108
Biological Activity......Page 109
Biosynthesis and Its Regulation......Page 110
References......Page 111
Introduction......Page 137
Moulting Hormone......Page 138
Biosynthesis......Page 140
Storage Products......Page 141
Inactivation......Page 143
Crustaceans and Other Phyla......Page 145
Structure Determination......Page 146
Ecdysteroids in Mammals......Page 147
Mammalian Hormones in Arthropods......Page 148
Structures......Page 149
Biosynthesis and Degradation......Page 150
JH in Arthropods......Page 153
Phytojuvenoids......Page 154
Eicosanoids......Page 155
Conclusion......Page 157
References......Page 158
Pheromones of Terrestrial Invertebrates......Page 162
Endocrinology......Page 163
Neurophysiology......Page 164
Isolation and Structure Elucidation......Page 165
Aromatic Compounds......Page 168
Nitrogen-Containing Aromatic Compounds......Page 170
Mixtures of Hydrocarbons Acting as Pheromones......Page 172
Female Lepidopteran Sex Pheromones......Page 173
C5-units......Page 177
C8-units......Page 178
C10-units......Page 179
C11-units......Page 180
C13-units......Page 181
C14-units......Page 182
C16-units......Page 183
C17-units......Page 184
C19-units......Page 185
C21-units......Page 187
C23-units......Page 189
C27-units......Page 190
C31-units......Page 191
Terpenes......Page 192
Monoterpenes......Page 198
Sesquiterpenes......Page 201
Norterpenes......Page 203
Homoterpenes......Page 204
Propanogenins and Related Compounds......Page 205
Mixed Structures......Page 209
Other Structures......Page 214
References......Page 216
Pheromones in Vertebrates......Page 233
Biological Activity of Pheromones: Defining Principles......Page 234
Primer on Chemistry Issues......Page 236
Identifying a Pheromone......Page 237
Pheromones in Ancient Vertebrates......Page 238
Male sex pheromone: Chemistry......Page 239
Migratory pheromone: Biology......Page 240
Migratory pheromone: Chemistry......Page 241
Pheromones in Advanced (Teleost) Fishes......Page 242
Female sex pheromone: Chemistry......Page 243
Female sex pheromone: Chemistry......Page 244
Male sex pheromone: Chemistry......Page 245
Male and female sex pheromones: Biology......Page 246
Male and female sex pheromones: Chemistry......Page 247
Male sex pheromones: Biology......Page 248
Male sex pheromone: Chemistry......Page 249
Male sex pheromone: Chemistry......Page 250
Female sex pheromone: Chemistry......Page 252
Pheromones in Birds......Page 253
Pheromones in Mammals......Page 254
Female sex pheromone: Biology......Page 256
Male-derived priming pheromone: Biology......Page 257
Male-derived priming pheromone: Chemistry......Page 259
Female-derived puberty inhibiting pheromone: Chemistry......Page 260
Male pig (boar) pheromone: Chemistry......Page 261
Asian Elephant......Page 262
Male sex pheromone: Biology......Page 263
Humans......Page 264
Overview......Page 265
References......Page 266
Brown Algae......Page 271
Green Algae......Page 274
Sea Urchin......Page 276
Coral......Page 277
Abalone......Page 279
Polychaete Worm......Page 281
Sea Hare......Page 282
Crab......Page 283
Sea Anemone......Page 284
Summary and Future Prospects......Page 285
References......Page 286
Cell-to-Cell Communications among Microorganisms......Page 290
Introduction......Page 291
Introduction......Page 292
General Properties of gamma-Butyrolactones in Streptomyces......Page 293
A-factor homologues in Actinomycetes......Page 295
AfsA as the key enzyme for A-factor biosynthesis......Page 296
Properties of ArpA......Page 298
Crystallography of CprB, an ArpA homologue......Page 299
Properties of AdpA......Page 300
AdpA regulon......Page 301
Introduction......Page 302
Antibiotics as Signal Molecules......Page 303
Role of Ferrioxamines......Page 304
Introduction......Page 305
Sex pheromones of E. faecalis......Page 306
Competence- and sporulation-stimulating factors of Bacillus subtilis......Page 308
Inducer peptide pheromones of class II bacteriocins......Page 309
Competence-stimulating peptides of streptococci......Page 310
Bacteriocin-like peptides encoded by streptococcal genomes......Page 313
Nisin and subtilin......Page 314
Cytolysin......Page 315
Autoinducer peptides in staphylococci......Page 316
Gelatinase biosynthesis-activating pheromone in E. faecalis......Page 318
Cyclic AIPs in other Gram-positive bacteria......Page 320
Isoprenylated Peptide as a Competence Pheromone of B. subtilis......Page 321
N-Acylhomoserine Lactones as Autoinducers of Quorum Sensing......Page 322
Vibrio fischeri and Vibrio harveyi......Page 324
Pseudomonas aeruginosa......Page 327
Serratia species......Page 328
Burkholderia species......Page 329
Agrobacterium tumefaciens and Chromobacterium violaceum......Page 330
Other Types of Autoinducers......Page 331
Autoinducer-2......Page 332
PQS......Page 333
Cholerae autoinducer-1......Page 334
Stigmolone......Page 335
Aryl-HSL in Rhodopseudomonas palustris......Page 336
References......Page 337
Introduction......Page 345
Alkaloids......Page 346
Cyanogenic glycosides......Page 349
Glucosinolates......Page 350
Hormone analogues: Phytojuvenile hormones and phytoecdysteroids......Page 352
Cardenolides......Page 353
Iridoid glycosides......Page 355
Defense proteins......Page 356
Lectins......Page 357
Enzymatic activation of precursors, compartmentation, and synergism of defense factors......Page 358
Plant tissues specialized in defense and localization of defensive substances......Page 359
Induction of defense substance......Page 360
Attracting carnivorous natural enemies by using herbivore-induced plant volatiles......Page 361
Tritrophic interactions of plant-spider mite-carnivorous natural enemy......Page 362
HIPVs affect neighboring plant’s indirect defense......Page 363
Insect factors affecting the production of HIPVs......Page 364
Signaling pathways involved in the production of HIPVs in plants......Page 365
Introduction......Page 367
Constitutive Chemical Defense......Page 368
Phytoalexins......Page 371
Chemical Defenses of Plants......Page 376
Polyketides......Page 377
Nonribosomal Peptides......Page 379
Terpenoids......Page 380
References......Page 382
Introduction......Page 392
Alveolata......Page 393
Cnidaria......Page 395
Nemertini......Page 396
Mollusca......Page 397
Annelida: Clitellata: Oligochaeta......Page 398
Arthropoda: Onychophora......Page 399
Arthropoda: Crustacea, Isopoda......Page 400
Arthropoda: Chelicerata, Acari (Mites)......Page 401
Arthropoda: Chelicerata, Opiliones......Page 403
Arthropoda: Chelicerata, Pedipalpi......Page 405
Arthropoda: Chelicerata, Araneae......Page 406
Arthropoda: Myriapoda: Opisthogoneata (Centipedes)......Page 407
Arthropoda: Myriapoda: Progoneata: Diplopoda (Millipedes) and Symphyla......Page 408
Acknowledgments......Page 411
References......Page 412
Introduction......Page 416
Insecticidal Metabolites of Bacteria......Page 417
Insecticidal Metabolites of Fungi......Page 419
Mycotoxins......Page 424
Ochratoxins, Fumonisins, Zearalenone, and Ergot Alkaloids......Page 426
Miscellaneous Mycotoxins......Page 429
Aflatoxins......Page 433
Biosynthesis of aflatoxins......Page 435
Regulatory mechanism of aflatoxin production......Page 439
Regulation of aflatoxin production and contamination......Page 440
Trichothecenes......Page 442
A common pathway of trichothecene biosynthesis: From FPP to ITdiol......Page 445
Type A trichothecenes......Page 446
Type B trichothecenes......Page 447
Pathway, transport, and regulatory genes for the biosynthesis of Fusarium trichothecenes in the Tri5 gene cluster......Page 450
Pathway genes for the biosynthesis of Fusarium trichothecenes in the Tri1-Tri16 two-gene cluster......Page 452
Summary and perspectives......Page 453
References......Page 454
Introduction......Page 461
Bioassays......Page 462
Microassay......Page 463
Monoterpenes......Page 464
Sesquiterpenes......Page 465
Sesquiterpene lactones......Page 468
Eremophilanolides......Page 470
Clerodanes......Page 471
Ryanoids......Page 477
Diterpenoid alkaloids......Page 478
Pentacyclic triterpenes......Page 480
Limonoids......Page 482
Phragmalins......Page 488
Cucurbitacins......Page 492
Glycoalkaloids......Page 493
Lignans......Page 494
Coumarins and Quinones......Page 496
Flavonoids......Page 497
Cardenolides......Page 499
Feeding Deterrence in Higher Animals......Page 500
References......Page 501
Introduction......Page 506
Experimental Methodology......Page 507
Cyanobacteria......Page 508
Terpenes......Page 510
Other Acetate-Derived Metabolites......Page 512
Sponges......Page 513
Alkaloids......Page 514
Terpenes......Page 518
Soft Corals......Page 520
Hydroids......Page 522
Ascidians......Page 524
Bryozoans......Page 526
Sea Hares......Page 527
Sacoglossans......Page 528
Nudibranchs......Page 530
Other Mollusks......Page 534
Worms......Page 535
References......Page 536
Introduction......Page 541
Terpenoids......Page 542
Phenolic compounds......Page 545
Benzoxazinoids......Page 547
Other allelochemicals......Page 548
Introduction......Page 549
Root nodules......Page 550
Germination inducers of phytopathogens......Page 554
Self-Defensive Allelochemicals in Plants......Page 556
Allelochemicals in Aquatic Ecosystems......Page 559
References......Page 560
Introduction......Page 564
Phytochemicals Involved in Oviposition......Page 565
Feeding Attractants and Stimulants......Page 571
Attractants in nursery pollination......Page 581
Attractants in sexual mimicry......Page 582
Attractants in abiotic mimicry......Page 583
Transfer of volatiles from flowers to insects......Page 584
Toxic components......Page 585
Parasitic Wasps......Page 586
Predators......Page 589
Elicitors......Page 590
References......Page 591
Human-Environment Interactions (1): Flavor and Fragrance......Page 596
Outline of the Flavor and Fragrance Industry......Page 597
Materials used in flavor and fragrance production......Page 598
Aroma creation and odor perception characteristics......Page 600
Application of Flavor and Fragrance Products......Page 601
Common Analytical Methods......Page 602
AEDA, CHARM, and odor unit determination......Page 603
Sample Preparation Method......Page 604
Quality Control......Page 605
Aroma Products from Leaves and Allied Plant Materials......Page 606
Aroma Products from Seeds......Page 607
Essential Oils from Peel (Citrus Oil)......Page 608
Aroma Material from Other Botanical Sources......Page 609
Aroma-Active Material from Animals......Page 610
Artificial Fragrance Materials......Page 613
Fruits......Page 614
Alcoholic Beverages......Page 616
Condiments......Page 617
Dairy Products......Page 618
Human Interactions......Page 619
Biological Background of Olfactory Perception......Page 621
Outlook......Page 623
References......Page 624
Human-Environment Interactions - Taste......Page 631
Introduction......Page 632
Natural Products Associated with Sweetness......Page 633
Stevioside......Page 634
Mogroside......Page 635
Pterocaryosides A and B......Page 636
Proteinogenic amino acids......Page 637
Thaumatin......Page 638
Monellin......Page 639
Brazzein......Page 640
Curculin and neoculin......Page 641
Gymnemic acid......Page 642
Hodulcin......Page 643
Brucine......Page 644
Theobromine and theophyllin......Page 645
Solanine......Page 646
Limonoids......Page 647
Lactucin and cynaropicrin......Page 648
Quassin......Page 649
Secoiridoid saponins......Page 650
Amino acids......Page 651
Capsaicin......Page 652
Piperine......Page 653
Isothiocyanates......Page 654
Disulfides......Page 655
Catechins in Green Tea......Page 656
Theaflavins and Thearubigins in Black Tea......Page 657
Anthocyanins in Red Wine......Page 658
Monosodium glutamate......Page 659
Nucleotides......Page 660
Kokumi-inducing natural products......Page 661
Sour Taste Receptors......Page 662
Succinic acid......Page 663
References......Page 664