Insect Lipids: Chemistry, Biochemistry, and Biology

By David W. Stanley-Samuelson; Dennis R. Nelson | Go to book overview
The German Cockroach Contact Sex Pheromone: Biology, Biochemistry and Endocrine Regulation335
4.1 German Cockroach Contact Sex Pheromone335
4.2 Biosynthesis of the German Cockroach Sex Pheromone336
4.3 Conversion of 3,11-Dimethylnonacosane to Sex Pheromone340
4.4 Endocrine Regulation of Sex Pheromone Production in the German Cockroach340
Acknowledgments341
References341

1 Abstract

Many insect species use cuticular lipid components in chemical communication. Cuticular hydrocarbons and their derivatives serve as close range and contact sex pheromones, aphrodisiacs, anti-aphrodisiacs, aggregation pheromones, kairomones, nestmate recognition cues and function in chemical mimicry. Recent work with several species of insects has led to new insights into how the production of hydrocarbons and their derivatives for use in chemical communication is regulated. The close range and contact sex pheromones of the housefly, Musca domestica, and the German cockroach, Blattella germanica, consist of modified cuticular lipids. In the housefly, the chain length of the synthesized alkenes switch from 27 carbons and longer in immature females, to 23 carbons as the female becomes vitellogenic. This 23-carbon alkene, (Z)-9-tricosene, is the major sex pheromone component of female houseflies. Removal of the ovaries within six hours of emergence prevents sex pheromone production, whereas reimplantation of ovaries or treatment with 20-hydroxyecdysone (20-HE) (all abbreviations defined in Table 1) restores sex pheromone production. Recent work has shown that 20-HE exerts its action by causing a change in the chain length specificity of the elongation reactions and not in the reactions that reductively convert very-long chain acyl-CoAs to hydrocarbons.

The contact sex pheromone of the German cockroach consists of the oxygenated derivatives of 3,11-dimethylnonacosane and 3,11-dimethylheptacosane. The methyl-branched hydrocarbons arise from the insertion of methylmalonyl-CoA, derived from branched-chain amino acids or succinate, in place of malonyl-CoA early in chain synthesis by a microsomal fatty acid synthase (FAS). The methyl-branched fatty acids present in the integument of the insect have the same positional isomers as do the major methyl-branched hydrocarbons. The C29 methyl-branched alkane consists of 3 isomers with 3,7-, 3,9- and 3,11-dimethyl branching patterns. Only the 3,11-dimethylnonacosane is specifically hydroxylated

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Insect Lipids: Chemistry, Biochemistry, and Biology
Table of contents

Table of contents

  • Title Page iii
  • Contributors v
  • Contents ix
  • Preface xi
  • References xiii
  • Lipoproteins and Lipid Transport 1
  • 7: Concluding Remarks 20
  • References 21
  • Structure and Function of Manduca Sexta Hemolymph Lipid Transfer Particle 25
  • Acknowledgments 40
  • The Biological Significance of Prostaglandins and Related Eicosanoids in Insects 45
  • 1: Introduction 46
  • Acknowledgments 88
  • Arachidonate Metabolism in Tick Salivary Glands 99
  • 1: Introduction 100
  • Acknowledgments 129
  • References 130
  • Prostanoids and Fluid Balance in Insects 139
  • Acknowledgments 172
  • Cuticular Hydrocarbons and Chemical Communication 179
  • Acknowledgments 212
  • Cuticular Polar Lipids of Insects 227
  • 1: Introduction 228
  • References 261
  • Methyl-Branched Lipids in Insects 271
  • 8: Concluding Remarks 301
  • Hydrocarbon and Hydrocarbon Derived Sex Pheromones in Insects: Biochemistry and Endocrine Regulation 317
  • 1: Abstract 318
  • Acknowledgments 341
  • Biosynthesis and Endocrine Regulation of Fatty Acid Derived Sex Pheromones in Moths 353
  • 1: Introduction 353
  • 4: Conclusion 379
  • Lipid Biochemistry in Aphids 389
  • 1: Introduction 389
  • 12: Conclusions and Future Directions 423
  • References 424
  • Species Name Index 435
  • Common Name Index 443
  • Subject Index 449
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