A contact sex pheromone component of the emerald ash borer Agrilus planipennis Fairmaire (Coleoptera: Buprestidae)

Silk, Peter J.; Ryall, Krista; Lyons, D. Barry; Sweeney, Jon; Wu, Junping

doi:10.1007/s00114-009-0513-1

Cited by 63 publications

(91 citation statements)

References 23 publications

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“…In particular, it is not always fully understood whether the CHC bouquet is perceived as a whole or whether single key components are sufficient alone or in combination to elicit a full behavioural response (Ginzel et al, 2003;Sugeno et al, 2006;Lacey et al, 2008;Silk et al, 2009). Recent studies on plant volatiles showed that key components of complex mixtures are often behaviourally active only in the presence of the natural odour background (Mumm and Hilker, 2005;Schroeder and Hilker, 2008).…”

Section: Introductionmentioning

confidence: 99%

“…Hitherto, enantiomers of long-chain methylalkanes cannot be separated with state-of-the-art analytical tools, and thus the enantiomeric composition of these natural products still remains an open question (Hefetz et al, 2010;Millar, 2010). Consequently, although methylbranched CHCs have been identified as contact pheromones in some species (Sugeno et al, 2006;Ginzel et al, 2003;Lacey et al, 2008;Silk et al, 2009), it is unknown whether insects respond to these compounds stereoselectively (Hefetz et al, 2010), as is the case in many volatile insect pheromones (Mori, 2007).…”

Section: Introductionmentioning

confidence: 99%

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Deciphering the signature of cuticular lipids with contact sex pheromone function in a parasitic wasp

Kühbandner

Sperling

Mori³

et al. 2012

Journal of Experimental Biology

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SUMMARYThe surface of insects is covered by a complex mixture of cuticular hydrocarbons (CHCs) to prevent desiccation. In many species these lipids also have communicative functions, but often it is unknown which components are crucial for the behavioural response. Furthermore, it is often ignored that polar lipids also occur on the insectsʼ cuticle and might interact with CHCs. In the parasitic wasp Lariophagus distinguendus, CHCs function as a contact sex pheromone eliciting wing-fanning in males. Interestingly, not only females but also newly emerged males have the pheromone, resulting regularly in homosexual courtship. However, males deactivate the pheromone within the first two days after emergence. This deactivation is accompanied by the disappearance of 3-methylheptacosane (3-MeC27) and some minor components from the CHC profile of males. Here we show that 3-MeC27 is a key component of the contact sex pheromone which, however, triggers courtship behaviour only if an olfactory background of other cuticular lipids is present. Males responded to (S)-3-MeC27 enantioselectively when applied to filter paper but on three-dimensional dummies both enantiomers were behaviourally active, suggesting that physical stimuli also play a role in sexual communication of the wasps. Finally, we report that triacylglycerides (TAGs) are also essential components of the pheromone, and present evidence that TAGs actually occur on the cuticle of L. distinguendus. Our data provide novel insights into the semiochemical function of cuticular lipids by showing that the bioactivity of CHCs may be influenced by the stereochemistry and a synergetic interaction with long time ignored TAGs.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Deciphering the signature of cuticular lipids with contact sex pheromone function in a parasitic wasp

Kühbandner

Sperling

Mori³

et al. 2012

Journal of Experimental Biology

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“…Thus, many studies have been correlational only, showing statistically significant differences in the amounts and/or types of compounds present, without being able to confirm that any one or any group of these compounds do indeed have a signaling role. Other studies have bioassayed synthesized CHCs to probe the roles of specific compounds, with some success (15)(16)(17)(18)(19)(20)(21)(22). However, this approach is limited by the large number of compounds in CHC extracts so that a single study might require syntheses of numerous standards to assess the functional roles of all possible components.…”

Section: Discussionmentioning

confidence: 99%

“…Methyl-branched cuticular hydrocarbons (MBCHs) have been identified or implicated as contact pheromones in a number of insect species (15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26)(27), but most studies involving MBCHs have ignored the issue of stereochemistry and used only racemic MBCHs in bioassays to assess function. The linked questions as to whether insects biosynthesize MBCHs enantioselectively and whether insects can discriminate between the stereoisomeric Significance Methyl-branched hydrocarbons (MBCHs) are widely used for inter-and intraspecific communication by insects.…”

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confidence: 99%

Isolation and determination of absolute configurations of insect-produced methyl-branched hydrocarbons

Bello¹,

McElfresh

Millar

2015

Proc. Natl. Acad. Sci. U.S.A.

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Although the effects of stereochemistry have been studied extensively for volatile insect pheromones, little is known about the effects of chirality in the nonvolatile methyl-branched hydrocarbons (MBCHs) used by many insects as contact pheromones. MBCHs generally contain one or more chiral centers and so two or more stereoisomeric forms are possible for each structure. However, it is not known whether insects biosynthesize these molecules in high stereoisomeric purity, nor is it known whether insects can distinguish the different stereoisomeric forms of MBCHs. This knowledge gap is due in part to the lack of methods for isolating individual MBCHs from the complex cuticular hydrocarbon (CHC) blends of insects, as well as the difficulty in determining the absolute configurations of the isolated MBCHs. To address these deficiencies, we report a straightforward method for the isolation of individual cuticular hydrocarbons from the complex CHC blend. The method was used to isolate 36 pure MBCHs from 20 species in nine insect orders. The absolute stereochemistries of the purified MBCHs then were determined by digital polarimetry. The absolute configurations of all of the isolated MBCHs were determined to be (R) by comparison with a library of synthesized, enantiomerically pure standards, suggesting that the biosynthetic pathways used to construct MBCHs are highly conserved within the Insecta. The development of a straightforward method for isolation of specific CHCs will enable determination of their functional roles by providing pure compounds for bioassays.T he use of chemical signals is highly developed within insects, with semiochemicals mediating a wide variety of inter-and intraspecific behaviors. Volatile pheromones, such as sex and aggregation pheromones, are the most well-known types, but insects also use nonvolatile cuticular lipids as contact pheromones (1-4). The cuticular lipids consist of a complex blend of n-and methyl-branched alkanes, alkenes, and lesser amounts of more polar compounds such as esters and alcohols. The lipid layer acts primarily as a waterproofing barrier (5), but individual lipid components have evolved secondary roles as signals that mediate a variety of behaviors and physiological changes (1, 2, 6). For example, solitary insects use cuticular hydrocarbons (CHCs) to identify the species and sex of mates (7, 8) whereas, in social insects, CHCs mediate identification of nestmates (9, 10), recognition of castes, and task allocation within the colony (11). Social insect queens also use CHCs to signal fecundity and dominance status within the colony, inhibiting development of workers into reproductives (12)(13)(14).Determining the roles of specific CHCs as signals has been hindered by three interlinked problems. First, CHCs typically consist of a large number of compounds, which can be difficult to isolate in pure form to test their bioactivities. Specifically, CHCs have very similar polarity and so are not separable by liquid chromatography on silica gel or other polar chromatographic m...

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“…Furthermore, a long range pheromone has not yet been detected for EAB [92]. Two short range, contact pheromones produced by adult emerald ash borer females have been identified that are antennally attractive to the males and have been used to improve trap captures [80,90,93,94]. Currently, key survey methods include the use of external signs and symptoms, green and purple sticky prism traps baited with ash volatile lures, green multi-funnel traps, trap logs, and using girdled trap trees which are an expensive and destructive method [15,88,92,95].…”

Section: Past and Present Detection Methods And Treatment Optionsmentioning

confidence: 99%

Forest Health Management and Detection of Invasive Forest Insects

Finley

Chhin

2016

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Abstract:The objectives of this review paper are to provide an overview of issues related to forest health and forest entomology, explain existing methods for forest insect pest detection, and provide background information on a case study of emerald ash borer. Early detection of potentially invasive insect species is a key aspect of preventing these species from causing damage. Invasion management efforts are typically more feasible and efficient if they are applied as early as possible. Two proposed approaches for detection are highlighted and include dendroentomology and near infrared spectroscopy (NIR). Dendroentomology utilizes tree ring principles to identify the years of outbreak and the dynamics of past insect herbivory on trees. NIR has been successfully used for assessing various forest health concerns (primarily hyperspectral imaging) and decay in trees. Emerald ash borer (EAB) (Agrilus planipennis), is a non-native beetle responsible for widespread mortality of several North American ash species (Fraxinus sp.). Current non-destructive methods for early detection of EAB in specific trees are limited, which restricts the effectiveness of management efforts. Ongoing research efforts are focused on developing methods for early detection of emerald ash borer.

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A contact sex pheromone component of the emerald ash borer Agrilus planipennis Fairmaire (Coleoptera: Buprestidae)

Cited by 63 publications

References 23 publications

Deciphering the signature of cuticular lipids with contact sex pheromone function in a parasitic wasp

Deciphering the signature of cuticular lipids with contact sex pheromone function in a parasitic wasp

Isolation and determination of absolute configurations of insect-produced methyl-branched hydrocarbons

Forest Health Management and Detection of Invasive Forest Insects

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