Insect Hydrocarbons: Biology, Biochemistry, and Chemical Ecology

Half-title......Page 3
Title......Page 5
Copyright......Page 6
Contents......Page 7
Contributors......Page 9
Foreword......Page 11
Acknowledgments......Page 13
Part I Chemistry, Biochemistry, and Physiology......Page 15
1 Introduction: history and overview of insect hydrocarbons......Page 17
References......Page 25
Types of hydrocarbons......Page 33
Unsaturated hydrocarbons......Page 34
Methyl-branched alkanes......Page 36
Characterization of hydrocarbons......Page 38
Mass spectral fragmentation patterns......Page 39
Positions of double bonds......Page 42
Distribution of hydrocarbons on the cuticle......Page 43
References......Page 44
Site of cuticular hydrocarbon biosynthesis......Page 49
Biosynthetic pathways for hydrocarbons......Page 50
Chain length specificity......Page 51
Methyl-branched hydrocarbon biosynthesis......Page 54
Methyl-branched fatty acids......Page 56
Ecdysteroid regulation of hydrocarbon production in the housefly......Page 57
Metabolism of cuticular hydrocarbons......Page 58
Developmental regulation of hydrocarbon synthesis and deposition......Page 59
References......Page 61
4 Molecular biology and genetics of hydrocarbon production......Page 67
Desaturases......Page 68
Role of Desat1......Page 69
Role of Desat2......Page 70
Expression of desat1 and desat2 in the Tai strain......Page 73
Role of DesatF......Page 75
Elongases......Page 76
Elongases involved in male 7-T/7-P ratio......Page 77
Elongases involved in female long HC synthesis......Page 79
cis-vaccenyl acetate (cVA) biosynthesis......Page 80
Evolution of HC synthesis enzymes in Drosophila......Page 81
Second desaturation......Page 82
References......Page 83
5 Site of synthesis, mechanism of transport and selective deposition of hydrocarbons......Page 89
Transport of hydrocarbons with lipophorin......Page 90
Social insects, hydrocarbon transport and deposition......Page 93
Role of endocrine and physiological factors in regulation of biosynthesis and transport in social insects......Page 95
Site of synthesis......Page 96
Role of various glands in hydrocarbon production and storage......Page 97
Role of the postpharyngeal gland in ants......Page 98
References......Page 104
Is cuticular permeability important? Cuticular and respiratory water-loss......Page 114
Correlations between cuticular lipids and water-loss rates......Page 116
Experimental tests of the phase transition model......Page 118
Lipid composition and physical properties: size doesn’t matter (much)......Page 120
Theoretical consideration of the transition phenomenon......Page 123
Are cuticular lipids the entire story? Melanization and water-loss......Page 126
References......Page 129
7 Chemical taxonomy with hydrocarbons......Page 135
Chemotaxonomy and sex pheromones......Page 136
Pheromone polymorphism in d. elegans......Page 137
D. mojavensis cluster......Page 138
Pheromone polymorphism in the adiastola subgroup......Page 139
Coleoptera (Table 7.3)......Page 140
Other taxa......Page 143
Urban pests......Page 144
Nematocera (Diptera) suborder......Page 150
Diptera – Brachycera Suborder (Table 7.5)......Page 152
Hymenoptera......Page 154
Coleoptera......Page 155
Dictyoptera......Page 156
Social Hymenopterans......Page 157
Isoptera......Page 158
Chemotaxonomy, phylogeny and speciation......Page 159
Conclusion......Page 161
References......Page 162
8 Chemical synthesis of insect cuticular hydrocarbons......Page 177
Preamble: convenient methods of purification of synthesized cuticular hydrocarbons......Page 179
Methods of synthesizing various classes of cuticular hydrocarbons......Page 181
References......Page 195
Secondary alcohols......Page 201
Secondary alcohol esters......Page 202
Methyl-branched alcohols......Page 203
Ethers......Page 204
Epoxy derivatives of di-alkenes......Page 205
Ketones as glandular lipids......Page 206
Keto-alcohols, keto-aldehydes and keto-wax esters......Page 207
Protective water barrier......Page 208
Ketones and secondary alcohols......Page 209
Methyl-branched ketones (German cockroach pheromone)......Page 210
References......Page 211
Part II Chemical Communication......Page 219
10 Perception and olfaction of cuticular compounds......Page 221
Tip-recording method for electrophysiological study of chemosensory sensilla......Page 222
Functional searching for the ant CHC sensillum by electrophysiological method......Page 223
Perireceptor events and role of lipophilic ligand-carrier proteins......Page 224
Ligand binding of lipophilic ligand carrier proteins......Page 227
Chemoreception of cuticular hydrocarbons and aggressive behavior expression......Page 228
References......Page 231
11 Nestmate recognition in social insects and the role of hydrocarbons......Page 236
Social parasites......Page 238
Correlative evidence and removal-and-replacement experiments......Page 240
Direct evidence for cuticular hydrocarbons......Page 241
The acceptance threshold......Page 244
The referents and gestalt odor......Page 246
The neural mechanism and a new model......Page 247
Synthesis......Page 249
References......Page 251
12 Cuticular hydrocarbon cues in the formation and maintenance of insect social groups......Page 258
References......Page 264
The importance of chemical communication in the regulation of reproduction in social insects......Page 268
Communication of reproductive status in social insects......Page 269
Species with workers having a limited reproductive potential......Page 270
Species with queens and workers having a strong reproductive potential......Page 273
Pure gamergate species......Page 276
Hydrocarbon profiles and egg discrimination......Page 277
Pachycondyla inversa......Page 278
Polistes dominulus......Page 279
Hydrocarbon profiles and social hierarchy......Page 280
Recognition of hydrocarbon profiles relating to fertility......Page 281
Ants......Page 283
Single versus multiple compounds and compound classes......Page 285
Cuticular profiles versus egg profiles......Page 286
Conclusions......Page 287
References......Page 289
14 Chemical deception/mimicry using cuticular hydrocarbons......Page 296
Plant–insect interactions......Page 298
Non-social arthropod interactions......Page 299
Honeybee parasites......Page 303
Myrmecophiles......Page 306
Intraspecific mimicry in insects......Page 310
Artificially mixed social insect colonies......Page 311
Interactions among social insects belonging to different orders......Page 312
Interactions among social insects belonging to different genera......Page 313
Interactions among social insects within the same genus......Page 319
Interaction among social insects within the same species......Page 323
Concluding remarks......Page 324
References......Page 327
15 Behavioral and evolutionary roles of cuticular hydrocarbons in Diptera......Page 339
Drosophilidae......Page 340
D. melanogaster and D. simulans – major CHC components......Page 342
Calliphoridae......Page 344
Glossinidae......Page 345
Male courtship of other males and of immature flies......Page 346
Cucilidae......Page 347
Fitness effects......Page 348
Interspecific variation and evolutionary effects......Page 349
Future prospects......Page 350
References......Page 351
Contact recognition pheromones in spiders......Page 358
Identification of silk and cuticle lipids......Page 359
Contact recognition pheromones and sexual behavior in spiders......Page 363
Contact recognition pheromones and social behavior in spiders......Page 368
Contact recognition pheromones in scorpions......Page 371
Chemosensory experimentation and cuticular compounds of Smeringerus mesaensis......Page 372
Identification and assay of chemical recognition signals in Hadrurus arizonensis......Page 374
Conclusion on the role of the determined mixtures for the two scorpion species......Page 378
Conclusion......Page 379
References......Page 383
17 Hydrocarbons as contact pheromones of longhorned beetles (Coleoptera: Cerambycidae)......Page 389
Contact pheromones in the mating systems of longhorned beetles......Page 392
The use of bioassays to study contact chemoreception of cerambycids......Page 393
Sampling cuticular hydrocarbons......Page 394
Qualitative and quantitative differences in hydrocarbon profiles of the sexes......Page 397
Contact pheromones as single compounds or blends......Page 398
Conclusions......Page 399
References......Page 400
18 Polyene hydrocarbons, epoxides, and related compounds as components of lepidopteran pheromone blends......Page 404
Types of structure and nomenclature......Page 406
Taxonomic distribution of Type II pheromone compounds......Page 430
Analysis and identification of Type II pheromones......Page 432
Biosynthesis of Type II pheromones......Page 434
Chemical synthesis of Type II pheromones......Page 439
Conclusions......Page 446
References......Page 447
Sap beetles......Page 462
First evidence of pheromones and wind tunnel bioassay......Page 463
Pheromone identification......Page 464
Summary of male-specific hydrocarbons......Page 465
Synthesis and spectral properties......Page 467
Laboratory activity of synthetic pheromones......Page 468
Site of pheromone production......Page 470
Pheromone biosynthesis and composition......Page 472
Interactions among species in the field......Page 474
Field trapping parameters......Page 478
Practical uses......Page 479
Protection of Australian stone fruit orchards......Page 480
Flea beetles......Page 481
Other Coleoptera......Page 483
References......Page 484
The ubiquitous occurrence of hydrocarbons and their multifaceted function in insects present the biggest challenge......Page 491
Distribution of hydrocarbons, regulation and transport......Page 493
Perception and integration of complex hydrocarbon mixtures......Page 494
Gene and hormonal regulation of hydrocarbons......Page 495
References......Page 496
Index......Page 500