Pheromones of Terrestrial Invertebrates

Francke, Wittko; Schulz, Stefan

doi:10.1016/b978-008045382-8.00095-2

Cited by 38 publications

(27 citation statements)

References 839 publications

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“…17 One of the best-known examples of these naturally produced bioactive hydrocarbons is (Z)-tricos-9-ene which was described as a pheromone in dozens of species including the house fly (Musca domestica), acting in this case as a sex attractant. 18 On the other hand, there are only a few examples of natural occurrence of (Z)-tricos-11-ene (1) with only one example related to chemical communication.…”

Section: Resultsmentioning

confidence: 99%

Identification and Synthesis of the Male-Produced Sex Pheromone of the Soldier BeetleChauliognathus fallax(Coleoptera: Cantharidae)

Vidal

Fávaro

Guimarães

et al. 2016

Journal of the Brazilian Chemical Society

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Section: Resultsmentioning

confidence: 99%

Identification and Synthesis of the Male-Produced Sex Pheromone of the Soldier BeetleChauliognathus fallax(Coleoptera: Cantharidae)

Vidal

Fávaro

Guimarães

et al. 2016

Journal of the Brazilian Chemical Society

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“…The esters identified here represent a new class of epicuticular wax lipids exhibiting an internal location of the ester function and methyl branches in both the acid and alcohol part and a relatively short-chain length between C 22 and C 24 . The relatively short overall length of these wax esters compared to other epicuticular wax esters may allow perception already over short distances, as most volatile invertebrate pheromones have a chain length below C 25 [48]. Interestingly, a relative of A. elevatus, A. ululans is a cleptoparasite of An.…”

Section: Synthesis Of Estersmentioning

confidence: 99%

Identification and Synthesis of Branched Wax‐type Esters, Novel Surface Lipids from the Spider Argyrodes elevatus (Araneae: Theridiidae)

Chinta

Goller

Uhl³

et al. 2016

Chemistry & Biodiversity

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The analysis of cuticular extracts from the kleptoparasitic spider Argyrodes elevatus revealed the presence of unusual esters, new for arthropods. These novel compounds proved to be methyl-branched long-chain fatty acid esters with methyl branches located either close or remote from the internally located ester group. The GC/MS analysis of the prosoma lipid blend from the male cuticle contained one major component, undecyl 2-methyltridecanoate (1). In contrast, four major wax-type esters, 2-methylundecyl 2,8-dimethylundecanoate (2), 2,8-dimethylundecyl 2,8-dimethylundecanoate (3), heptadecyl 4-methylheptanoate (4), and 14-methylheptadecyl 4-methylheptanoate (5), were identified in the lipid blend of female prosomata. Structure assignments were based on mass spectra, gas chromatographic retention indices, and microderivatization. Unambiguous proof of postulated structures was ensured by an independent synthesis of all five esters. Preferentially, odd-numbered carbon chains pointed to a distinct biosynthetic pathway, different from that of common fatty acids, because one or two C starter units are incorporated during the biosynthesis of all acid and alcohol building blocks present in the five esters. The striking sexual dimorphism together with the unique biosynthesis points to a function of the esters in chemical communication of the spiders, although no behavioral data are currently available to test this assumption.

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“…[14] Within orchids,t he only examples are carbon disulfide, [15] dimethyl disulfide, [13] S-methyl thioacetate, [16] and 2-aminothiophenol, [13] each only reported once (Figure 1). Furthermore,w ea ppear to have discovered the first volatile sulfurcontaining pheromone in Hymenoptera [17] and the second in any animal [18] after methyl 2-(methylthio)benzoate was identified as asex pheromone for two beetle species (Figure 1). [19] Thechallenges in detecting,identifying,synthesizing,and confirming the function of new and unusual semiochemicals suggest that there is likely to be as trong bias towards reporting pollination studies involving common compounds.…”

Section: Communicationsmentioning

confidence: 99%

The Spider Orchid Caladenia crebra Produces Sulfurous Pheromone Mimics to Attract its Male Wasp Pollinator

et al. 2017

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One of the most intriguing natural observations is the pollination of orchids by sexual deception. Chemicals underpin this interaction between the orchida nd its sexually attracted male insect pollinator,with the signaling compounds involved, called semiochemicals,p redicted to mimic the chemical composition of the sex pheromone.W ei dentified floral semiochemicals from Caladenia (spider orchids) for the first time.W ef urther demonstrate that C. crebra attracts its single pollinator species with aunique system of (methylthio)-phenols,three of whichare new natural products.Furthermore, as predicted, the same compounds constitute the sex pheromone of the pollinator,t he thynnine wasp Campylothynnus flavopictus,r epresenting the first occurrence of sulfurous sex pheromones in Hymenoptera.While studies of plant-pollinator communities show that many plant species attract multiple pollinators, [1] numerous highly specialized pollination systems have been discovered that are underpinned by chemistry.[2a-c] Pollination through sexual deception is ah ighly specialized pollination strategy, primarily known from orchids,w here chemical mimicry of courting female insects leads to the attraction of male pollinators.[2] So far there have only been af ew studies where the compounds involved have been elucidated and confirmed with field bioassays.These include either blends of alkanes and alkenes,o rh ydroxy-and keto acids in Ophrys orchids,c yclohexane-1,3-diones in Chiloglottis orchids,a nd pyrazines in Drakaea orchids. [3] Caladenia is ad iverse genus of Australian terrestrial orchids,comprising over 360 species.[4] Thegenus is unique in that it employs multiple pollination strategies including food reward, food deception, and more than 100 cases of sexual deception.[5] Until now,t he identity of the chemicals for signaling between organisms (semiochemicals) involved in sexual deception has remained elusive for any Caladenia species,a lthough given that many different wasp genera are exploited, multiple chemical systems are expected to operate. Thus,d etailed studies of the chemistry of this genus,b eyond the promise of revealing new natural products,a lso offers au nique opportunity to better understand the role of floral volatiles in the evolution of sexual deception as apollination strategy.In this work, we investigated the chemistry of sexual deception in Caladenia crebra A.S.George.B yc ombining chemical ecology,analytical chemistry,and organic chemistry methods,wedemonstrate that in C. crebra,pollination by the thynnine wasp Campylothynnus flavopictus (Smith, 1859) requires as pecific blend of unique aromatic sulfurous compounds in precise ratios.I nt he exceptional mating behavior of thynnine wasps,t he larger,w inged males carry the smaller, wingless females in copula to af ood source for mating and feeding.[3a] While conducting field bioassays with artificially presented orchid flowers,o nt hree occasions, thynnine wasp pairs were observed arriving at the flower in copula, ab ehavior not previously rep...

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Pheromones of Terrestrial Invertebrates

Cited by 38 publications

References 839 publications

Identification and Synthesis of the Male-Produced Sex Pheromone of the Soldier BeetleChauliognathus fallax(Coleoptera: Cantharidae)

Identification and Synthesis of the Male-Produced Sex Pheromone of the Soldier BeetleChauliognathus fallax(Coleoptera: Cantharidae)

Identification and Synthesis of Branched Wax‐type Esters, Novel Surface Lipids from the Spider Argyrodes elevatus (Araneae: Theridiidae)

The Spider Orchid Caladenia crebra Produces Sulfurous Pheromone Mimics to Attract its Male Wasp Pollinator

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