Moth Pheromone Research Articles

How animals negotiate odor space in evolutionary- and real-time

The sensory odor space perceived by animals depends on their chemosensory repertoire – this information is used for the essential decisions in life [1,2]. This information is also used to negotiate the real-world 3-dimensional odor landscape to find food or a mate. The sensory odor space evolves as receptor families are co-opted and then undergo birth-and-death duplications, deletions and changes in response to natural selection. Insect and vertebrate olfactory receptors evolved independently. So, when male elephants and moths share the same odor space, with a shared molecule used as a female sex pheromone, we know that the receptors activated by the molecule are completely different and that they have evolved this sensitivity convergently. Finding most odor sources relies on the second key concept underlying olfaction, combinatorial processing leading to synergy: a behavioral response to the combination greater than the response to individual components of the blend. The co-occurrence of odorant molecules in the same parcel of air or water is what gives meaning to the odorscape. A moth pheromone may consist of molecules which are not rare in themselves. However, when they co-occur in a unique combination, they become the guiding signal for a male to orient upwind. The excitement of particular multiple glomeruli gives the meaning to the signal. Orientation behavior to find the source relies on this real-time combinatorial processing of sensory inputs, responding millisecond by millisecond to the filamentous plumes of odorants carried by wind or air. Anthropogenic CO2 and the acidification of the oceans are a threat to the odor space relied on by ocean life. As pH drops, the interactions between odorants and receptors change because the physicochemical properties of odor molecules are affected as are the binding sites of the receptors themselves. Will this lead to chemosensory “blindness”, with animals unable to find food or mates by the usual chemosensory stimuli? In the worst scenario, finding Nemo will become an impossible task.

A plant factory for moth pheromone production

Moths depend on pheromone communication for mate finding and synthetic pheromones are used for monitoring or disruption of pheromone communication in pest insects. Here we produce moth sex pheromone, using Nicotiana benthamiana as a plant factory, by transient expression of up to four genes coding for consecutive biosynthetic steps. We specifically produce multicomponent sex pheromones for two species. The fatty alcohol fractions from the genetically modified plants are acetylated to mimic the respective sex pheromones of the small ermine moths Yponomeuta evonymella and Y. padella. These mixtures are very efficient and specific for trapping of male moths, matching the activity of conventionally produced pheromones. Our long-term vision is to design tailor-made production of any moth pheromone component in genetically modified plants. Such semisynthetic preparation of sex pheromones is a novel and cost-effective way of producing moderate to large quantities of pheromones with high purity and a minimum of hazardous waste.

A Novel Fatty Acyl Desaturase from the Pheromone Glands of Ctenopseustis obliquana and C. herana with Specific Z5-Desaturase Activity on Myristic Acid

Sexual communication in the Lepidoptera typically involves a female-produced sex pheromone that attracts males of the same species. The most common type of moth sex pheromone comprises individual or blends of fatty acyl derivatives that are synthesized by a specific enzymatic pathway in the female’s pheromone gland, often including a desaturation step. This reaction is catalyzed by fatty acyl desaturases that introduce double bonds at specific locations in the fatty acid precursor backbone. The two tortricid moths, Ctenopseustis obliquana and C. herana (brown-headed leafrollers), which are endemic in New Zealand, both use (Z)-5-tetradecenyl acetate as part of their sex pheromone. In C. herana, (Z)-5-tetradecenyl acetate is the sole component of the pheromone. Labeling experiments have revealed that this compound is produced via an unusual Δ5-desaturation of myristic acid. Previously six desaturases were identified from the pheromone glands of Ctenopseustis and its sibling genus Planotortrix, with one differentially regulated to produce the distinct blends used by individual species. However, none were able to conduct the Δ5-desaturation observed in C. herana, and presumably C. obliquana. We have now identified an additional desaturase gene, desat7, expressed in the pheromone glands of both Ctenopseustis species, which is not closely related to any previously described moth pheromone desaturase. The encoded enzyme displays Δ5-desaturase activity on myristic acid when heterologously expressed in yeast, but is not able to desaturate any other fatty acid (C8–C16). We conclude that desat7 represents a new group of desaturases that has evolved a role in the biosynthesis of sex pheromones in moths.Electronic supplementary materialThe online version of this article (doi:10.1007/s10886-013-0373-1) contains supplementary material, which is available to authorized users.

Pheromone release rate determines whether sexual communication of Oriental fruit moth is disrupted competitively vs. non‐competitively

AbstractCommunicational disruption mechanisms for Oriental fruit moth, Grapholita molesta (Busck) (Lepidoptera: Tortricidae), were determined using a suite of mathematical tools and graphical operations that enable differentiation between competitive attraction and non‐competitive mechanisms of disruption. Research was conducted in 20 field cages, each covering 12 mature apple trees. Commercial monitoring lures releasing Oriental fruit moth pheromone at a rate of 0.04 μg h−1 and distributed at densities of 0, 1, 2, 4, 8, and 17 per cage were used to evaluate the effect of low‐releasing dispensers on the disruption of sexual communication. Graphical analyses revealed that near‐female‐equivalent pheromone dispensers disrupted Oriental fruit moth competitively. Commercial mating disruption dispensers releasing Oriental fruit moth pheromone at 60 μg h−1 and deployed at 0, 4, 6, 10, 15, 20, and 30 per cage were used to evaluate the effect of high‐releasing dispensers on the disruption of sexual communication. Oriental fruit moth disruption shifted to a non‐competitive mechanism for high‐releasing dispensers. This is the first time such a shift in disruption mechanism has been demonstrated against a background of otherwise identical experimental conditions. Near‐female‐equivalent pheromone dispensers were also used to quantify the additive effect of an attract‐and‐remove control strategy compared with competitive mating disruption. We report a five‐fold reduction in Oriental fruit moth captures under attract‐and‐remove compared to mating disruption using near‐female‐equivalent dispensers. Surprisingly, release of female Oriental fruit moths into these large‐cage disruption studies had no measurable impact on male trapping.

Communication Disruption of Guava Moth (Coscinoptycha improbana) Using a Pheromone Analog Based on Chain Length

The guava moth, Coscinoptycha improbana, an Australian species that infests fruit crops in commercial and home orchards, was first detected in New Zealand in 1997. A four-component pheromone blend was identified but is not yet commercially available. Using single sensillum recordings from male antennae, we established that the same olfactory receptor neurons responded to two guava moth sex pheromone components, (Z)-11-octadecen-8-one and (Z)-12-nonadecen-9-one, and to a chain length analog, (Z)-13-eicosen-10-one, the sex pheromone of the related peach fruit moth, Carposina sasakii. We then field tested whether this non-specificity of the olfactory neurons might enable disruption of sexual communication by the commercially available analog, using male catch to synthetic lures in traps in single-tree, nine-tree and 2-ha plots. A disruptive pheromone analog, based on chain length, is reported for the first time. Trap catches for guava moth were disrupted by three polyethylene tubing dispensers releasing the analog in single-tree plots (86% disruption of control catches) and in a plots of nine trees (99% disruption). Where peach fruit moth pheromone dispensers were deployed at a density of 1000/ha in two 2-ha areas, pheromone traps for guava moth were completely disrupted for an extended period (up to 470 days in peri-urban gardens in Mangonui and 422 days in macadamia nut orchards in Kerikeri). In contrast, traps in untreated areas over 100 m away caught 302.8 ± 128.1 moths/trap in Mangonui and 327.5 ± 78.5 moths/ trap in Kerikeri. The longer chain length in the pheromone analog has greater longevity than the natural pheromone due to its lower volatility. Chain length analogs may warrant further investigation for mating disruption in Lepidoptera, and screening using single-sensillum recording is recommended.

Functional specificity of sex pheromone receptors in the cotton bollworm Helicoverpa armigera.

Male moths can accurately perceive the sex pheromone emitted from conspecific females by their highly accurate and specific olfactory sensory system. Pheromone receptors are of special importance in moth pheromone reception because of their central role in chemosensory signal transduction processes that occur in olfactory receptor neurons in the male antennae. There are a number of pheromone receptor genes have been cloned, however, only a few have been functionally characterized. Here we cloned six full-length pheromone receptor genes from Helicoverpa armigera male antennae. Real-time PCR showing all genes exhibited male-biased expression in adult antennae. Functional analyses of the six pheromone receptor genes were then conducted in the heterologous expression system of Xenopus oocytes. HarmOR13 was found to be a specific receptor for the major sex pheromone component Z11-16:Ald. HarmOR6 was equally tuned to both of Z9-16: Ald and Z9-14: Ald. HarmOR16 was sensitively tuned to Z11-16: OH. HarmOR11, HarmOR14 and HarmOR15 failed to respond to the tested candidate pheromone compounds. Our experiments elucidated the functions of some pheromone receptor genes of H. armigera. These advances may provide remarkable evidence for intraspecific mating choice and speciation extension in moths at molecular level.

Functional differentiation of pheromone-binding proteins in the common cutworm Spodoptera litura

Pheromone-binding proteins (PBPs), a sub-family of odorant-binding proteins, are thought primarily to bind and transport the sex pheromones in moths. Considering multiple components of sex pheromone and multiple PBP genes exist in a single species, PBPs may contribute to the discrimination of different sex pheromone components. However, so far this discrimination is still unclear. Our previous ligand-binding assays showed that Spodoptera litura PBP1 (SlitPBP1) did not exhibit an obvious binding specificity among different sex pheromone components. In this study, binding specificity of the other two PBPs in S. litura (SlitPBP2 and SlitPBP3) was further investigated. As a result, SlitPBP2 was capable of binding all four sex pheromone components with similar affinities; whereas SlitPBP3 showed very weak binding affinities to them except Z9,E12–14:Ac. Similar results were also obtained from studied pheromone analogs, to which SlitPBP2 showed much stronger affinities than SlitPBP3. However, both SlitPBP2 and SlitPBP3 exhibited overall weaker affinities to sex pheromones and their analogs than SlitPBP1. In addition, quantitative real time PCR showed that three SlitPBP genes exhibited a very different sex-biased expression in adult antenna with male-biased for SlitPBP1 and SlitPBP2 while female-biased for SlitPBP3. Finally, ligand-binding assays indicated that the two SlitPBPs showed a similar pH-dependent conformational change as reported SlitPBP1, but these three SlitPBPs showed different behavior across a pH range or something similar. Taken together, our data suggest that in S. litura PBP1 and PBP2 may play critical roles in the perception of female sex pheromones, but do not show an obvious discriminative ability among different sex pheromone components; whereas PBP3 may have other functions.

Persistence of the Gypsy Moth Pheromone, Disparlure, in the Environment in Various Climates

Mating disruption techniques are used in pest control for many species of insects, yet little is known regarding the environmental persistence of these pheromones following their application and if persistence is affected by climatic conditions. We first studied the persistent effect of ground applications of Luretape® GM in Lymantria dispar (L) mating disruption in VA, USA in 2006. The removal of Luretape® GM indicated that the strong persistent effect of disparlure in the environment reported by previous studies is produced by residual pheromone in the dispensers as opposed to environmental contamination. In 2010 and 2011, we evaluated the efficacy of two formulations, Disrupt® II and SPLAT GMTM, in VA and WI, USA, which presented different climatic conditions. In plots treated in WI and VA, male moth catches in pheromone-baited traps were reduced in the year of treatment and one year after the pheromone applications relative to untreated controls. However, similar first- and second-year effects of pheromone treatments in VA and WI suggest that the release rate over one and two years was the same across markedly different climates. Future applications that use liquid or biodegradable formulations of synthetic pheromones could reduce the amount of persistence in the environment.

Changes in Odor Background Affect the Locomotory Response to Pheromone in Moths

Many animals rely on chemical cues to recognize and locate a resource, and they must extract the relevant information from a complex and changing odor environment. For example, in moths, finding a mate is mediated by a sex pheromone, which is detected in a rich environment of volatile plant compounds. Here, we investigated the effects of a volatile plant background on the walking response of male Spodoptera littoralis to the female pheromone. Males were stimulated by combining pheromone with one of three plant compounds, and their walking paths were recorded with a locomotion compensator and analyzed. We found that the addition of certain volatile plant compounds disturbed the orientation toward the sex pheromone. The effect on locomotion was correlated with the capacity of the plant compound to antagonize pheromone detection by olfactory receptor neurons, suggesting a masking effect of the background over the pheromone signal. Moths were more sensitive to changes in background compared to a constant background, suggesting that a background odor also acts as a distracting stimulus. Our experiments show that the effects of odorant background on insect responses to chemical signals are complex and cannot be explained by a single mechanism.

A moth pheromone brewery: production of (Z)-11-hexadecenol by heterologous co-expression of two biosynthetic genes from a noctuid moth in a yeast cell factory

BackgroundMoths (Lepidoptera) are highly dependent on chemical communication to find a mate. Compared to conventional unselective insecticides, synthetic pheromones have successfully served to lure male moths as a specific and environmentally friendly way to control important pest species. However, the chemical synthesis and purification of the sex pheromone components in large amounts is a difficult and costly task. The repertoire of enzymes involved in moth pheromone biosynthesis in insecta can be seen as a library of specific catalysts that can be used to facilitate the synthesis of a particular chemical component. In this study, we present a novel approach to effectively aid in the preparation of semi-synthetic pheromone components using an engineered vector co-expressing two key biosynthetic enzymes in a simple yeast cell factory.ResultsWe first identified and functionally characterized a ∆11 Fatty-Acyl Desaturase and a Fatty-Acyl Reductase from the Turnip moth, Agrotis segetum. The ∆11-desaturase produced predominantly Z11-16:acyl, a common pheromone component precursor, from the abundant yeast palmitic acid and the FAR transformed a series of saturated and unsaturated fatty acids into their corresponding alcohols which may serve as pheromone components in many moth species. Secondly, when we co-expressed the genes in the Brewer’s yeast Saccharomyces cerevisiae, a set of long-chain fatty acids and alcohols that are not naturally occurring in yeast were produced from inherent yeast fatty acids, and the presence of (Z)-11-hexadecenol (Z11-16:OH), demonstrated that both heterologous enzymes were active in concert. A 100 ml batch yeast culture produced on average 19.5 μg Z11-16:OH. Finally, we demonstrated that oxidized extracts from the yeast cells containing (Z)-11-hexadecenal and other aldehyde pheromone compounds elicited specific electrophysiological activity from male antennae of the Tobacco budworm, Heliothis virescens, supporting the idea that genes from different species can be used as a molecular toolbox to produce pheromone components or pheromone component precursors of potential use for control of a variety of moths.ConclusionsThis study is a first proof-of-principle that it is possible to “brew” biologically active moth pheromone components through in vitro co-expression of pheromone biosynthetic enzymes, without having to provide supplementary precursors. Substrates present in the yeast alone appear to be sufficient.

Quantitative analysis of pheromone‐binding protein specificity

Many pheromones have very low water solubility, posing experimental difficulties for quantitative binding measurements. A new method is presented for determining thermodynamically valid dissociation constants for ligands binding to pheromone-binding proteins, using β-cyclodextrin as a solubilizer and transfer agent. The method is applied to LUSH, a Drosophila odorant-binding protein that binds the pheromone 11-cis vaccenyl acetate (cVA). Refolding of LUSH expressed in Escherichia coli was assessed by measuring N-phenyl-1-naphthylamine (NPN) binding and Förster resonance energy transfer between LUSH tryptophan 123 (W123) and NPN. Binding of cVA was measured from quenching of W123 fluorescence as a function of cVA concentration. The equilibrium constant for transfer of cVA between β-cyclodextrin and LUSH was determined from a linked equilibria model. This constant, multiplied by the β-cyclodextrin-cVA dissociation constant, gives the LUSH-cVA dissociation constant: ∼100 nM. It was also found that other ligands quench W123 fluorescence. The LUSH-ligand dissociation constants were determined to be ∼200 nM for the silk moth pheromone bombykol and ∼90 nM for methyl oleate. The results indicate that the ligand-binding cavity of LUSH can accommodate a variety ligands with strong binding interactions. Implications of this for the Laughlin, Ha, Jones and Smith model of pheromone reception are discussed.

Specificity Determinants of the Silkworm Moth Sex Pheromone

The insect olfactory system, particularly the peripheral sensory system for sex pheromone reception in male moths, is highly selective, but specificity determinants at the receptor level are hitherto unknown. Using the Xenopus oocyte recording system, we conducted a thorough structure-activity relationship study with the sex pheromone receptor of the silkworm moth, Bombyx mori, BmorOR1. When co-expressed with the obligatory odorant receptor co-receptor (BmorOrco), BmorOR1 responded in a dose-dependent fashion to both bombykol and its related aldehyde, bombykal, but the threshold of the latter was about one order of magnitude higher. Solubilizing these ligands with a pheromone-binding protein (BmorPBP1) did not enhance selectivity. By contrast, both ligands were trapped by BmorPBP1 leading to dramatically reduced responses. The silkworm moth pheromone receptor was highly selective towards the stereochemistry of the conjugated diene, with robust response to the natural (10E,12Z)-isomer and very little or no response to the other three isomers. Shifting the conjugated diene towards the functional group or elongating the carbon chain rendered these molecules completely inactive. In contrast, an analogue shortened by two omega carbons elicited the same or slightly higher responses than bombykol. Flexibility of the saturated C1–C9 moiety is important for function as addition of a double or triple bond in position 4 led to reduced responses. The ligand is hypothesized to be accommodated by a large hydrophobic cavity within the helical bundle of transmembrane domains.

Moth Sex Pheromone Receptors and Deceitful Parapheromones

The insect's olfactory system is so selective that male moths, for example, can discriminate female-produced sex pheromones from compounds with minimal structural modifications. Yet, there is an exception for this “lock-and-key” tight selectivity. Formate analogs can be used as replacement for less chemically stable, long-chain aldehyde pheromones, because male moths respond physiologically and behaviorally to these parapheromones. However, it remained hitherto unknown how formate analogs interact with aldehyde-sensitive odorant receptors (ORs). Neuronal responses to semiochemicals were investigated with single sensillum recordings. Odorant receptors (ORs) were cloned using degenerate primers, and tested with the Xenopus oocyte expression system. Quality, relative quantity, and purity of samples were evaluated by gas chromatography and gas chromatography-mass spectrometry. We identified olfactory receptor neurons (ORNs) housed in trichoid sensilla on the antennae of male navel orangeworm that responded equally to the main constituent of the sex pheromone, (11Z,13Z)-hexadecadienal (Z11Z13-16Ald), and its formate analog, (9Z,11Z)-tetradecen-1-yl formate (Z9Z11-14OFor). We cloned an odorant receptor co-receptor (Orco) and aldehyde-sensitive ORs from the navel orangeworm, one of which (AtraOR1) was expressed specifically in male antennae. AtraOR1•AtraOrco-expressing oocytes responded mainly to Z11Z13-16Ald, with moderate sensitivity to another component of the sex pheromone, (11Z,13Z)-hexadecadien-1-ol. Surprisingly, this receptor was more sensitive to the related formate than to the natural sex pheromone. A pheromone receptor from Heliothis virescens, HR13 ( = HvirOR13) showed a similar profile, with stronger responses elicited by a formate analog than to the natural sex pheromone, (11Z)-hexadecenal thus suggesting this might be a common feature of moth pheromone receptors.

Functional characterization of a sex pheromone receptor in the pest moth Spodoptera littoralis by heterologous expression in Drosophila

Moth sex pheromone communication is recognised as a long-standing model for insect olfaction studies, and a widespread knowledge has been accumulated on this subject thanks to numerous chemical, electrophysiological and behavioural studies. A key step has been the identification of candidate sex pheromone receptors, opening new routes to understanding the specificity and sensitivity of this communication system, but only few of these receptors have as yet been functionally characterised. In this context, we aim at unravelling the molecular bases of pheromone reception in the noctuid moth Spodoptera littoralis. Taking advantage of a collection of antennal-expressed sequence tags, we previously identified three fragments of candidate pheromone receptors in this species. Here, we report full-length cloning of one of these receptors, named SlitOR6. Both sequence and expression pattern analyses were consistent with its annotation as a pheromone receptor, which we further confirmed by functional characterization. Using Drosophila antennae as a heterologous expression system, we identified a single component of the pheromone blend of S.littoralis, (Z,E)-9,12-tetradecadienyl acetate, as the ligand of SlitOR6. Two strategies were employed: (i) expressing SlitOR6 in the majority of Drosophila olfactory neurons, in addition to endogenous receptors, and monitoring the responses to pheromone stimuli by electroantennography; (ii) replacing the Drosophila pheromone receptor OR67d with SlitOR6 and monitoring the response by single sensillum recordings. Results were fully congruent and responses to (Z,E)-9,12-tetradecadienyl acetate were highly specific in both heterologous systems. This approach appears to be efficient and reliable for studying moth pheromone receptors in an in vivo context.

Semi–Selective Fatty Acyl Reductases from Four Heliothine Moths Influence the Specific Pheromone Composition

BackgroundSex pheromones are essential in moth mate communication. Information on pheromone biosynthetic genes and enzymes is needed to comprehend the mechanisms that contribute to specificity of pheromone signals. Most heliothine moths use sex pheromones with (Z)–11–hexadecenal as the major component in combination with minor fatty aldehydes and alcohols. In this study we focus on four closely related species, Heliothis virescens, Heliothis subflexa, Helicoverpa armigera and Helicoverpa assulta, which use (Z)–11–hexadecenal, (Z)–9–tetradecanal, and (Z)–9–hexadecenal in different ratios in their pheromone blend. The components are produced from saturated fatty acid precursors by desaturation, β–oxidation, reduction and oxidation.ResultsWe analyzed the composition of fatty acyl pheromone precursors and correlated it to the pheromone composition. Next, we investigated whether the downstream fatty–acyl reduction step modulates the ratio of alcohol intermediates before the final oxidation step. By isolating and functionally characterizing the Fatty Acyl Reductase (pgFAR) from each species we found that the pgFARs were active on a broad set of C8 to C16 fatty acyl substrates including the key pheromone precursors, Z9–14, Z9–16 and Z11–16:acyls. When presenting the three precursors in equal ratios to yeast cultures expressing any of the four pgFARs, all reduced (Z)–9–tetradecenoate preferentially over (Z)–11–hexadecenoate, and the latter over (Z)–9–hexadecenoate. Finally, when manipulating the precursor ratios in vitro, we found that the pgFARs display small differences in the biochemical activity on various substrates.ConclusionsWe conclude that a pgFAR with broad specificity is involved in heliothine moth pheromone biosynthesis, functioning as a semi–selective funnel that produces species–specific alcohol product ratios depending on the fatty–acyl precursor ratio in the pheromone gland. This study further supports the key role of these in pheromone biosynthesis and emphasizes the interplay between the pheromone fatty acyl precursors and the Lepidoptera specific pgFARs in shaping the pheromone composition.

Stochasticity in Sexual Selection Enables Divergence: Implications for Moth Pheromone Evolution

Sexual selection has long been hypothesized to lead to allopatric speciation, and one possible mechanism for this is that its interaction with stochasticity, which perturbs the trait and preference equilibria, can result in different traits being preferred in different populations. Here we specifically examine the role that stochastic changes in sexual selection strength plays in the shift of predominance between pairs of preferences and traits within a single population. We first create a single-locus null model of stochasticity during frequency dependent selection and then compare it to a two-locus population genetic model with stochastic strengths of female preferences for male traits. We find some interesting differences between the two models, primarily that in the two-locus sexual selection model shifts between preference and trait regimes occur more often with both weak and strong preferences, compared to intermediate preference strengths. We discuss the implications of our results for the evolution of pheromone blends and male responses during speciation in moths, a case that seems to match the assumptions of our model.

Pheromones and attractants of click beetles: an overview

The study of pheromones of click beetles was started with the objective of applying similar methods in IPM strategies for the control of wireworms, based on the similar experience gained from the widely used moth pheromones. A brief overview is presented on the identification of click beetle pheromones, new questions arising in the categorization of these pheromones into sex or aggregation pheromones, options for the development of female-targeted lures, and application perspectives.

A Flux Capacitor for Moth Pheromones

In this issue of Chemical Senses, Baker et al. propose a provocative and intriguing explanation for a commonly observed phenomenon in moth chemocommunication. Sex pheromones in moths typically consist of mixtures of long-chain unsaturated compounds in specific ratios. These ratios are correspondingly detected by male moths using separate olfactory sensory neurons for each pheromone component housed singly or multiply in long trichoid sensilla on the antennal surface. These neurons are often present in different proportions, typically with the neuron responding to the highest ratio component present in greatest abundance or with the largest dendritic diameter. In their article, Baker et al. postulate that these physical differences in neuron magnitudes arise to compensate for the higher molecular flux present with the most abundant pheromone components. Such a suggestion raises several questions concerning the physiological and behavioral nature of pheromone communication. Specifically, is the flux in a natural pheromone plume high enough to warrant increased flux detection for the most abundant components? Second, how can changes in neuronal number or size lead to increased flux detection? And finally, how would this increased flux detection be accomplished at molecular, cellular, and ultimately network scales? We address each of these questions and propose future experiments that could offer insight into the stimulating proposition raised by Baker et al.

A first glance on the molecular mechanisms of pheromone-plant odor interactions in moth antennae

A first glance on the molecular mechanisms of pheromone-plant odor interactions in moth antennae

A practical synthesis of (all- Z)-eicosa-3,6,9,12-tetraene, a pheromone component isolated from emerald moths

A short and practical synthesis of (all- Z)-eicosa-3,6,9,12-tetraene, a component of the emerald moth pheromone is reported. Two different methodologies are used both starting with the natural polyunsaturated fatty acid (all- Z)-eicosa-5,8,11,14,17-pentaenoic acid (EPA). The methodology can be used for the syntheses of a homologous series of analogues of the pheromone that may be practical for analytical purposes of similar natural products.