Linoleic Acid Promotes Emission of Bark Beetle Semiochemicals by Fungal Symbionts

Tree-killing bark beetles in conifer forests vector symbiotic fungi that are thought to help the beetles kill trees. Fungal symbionts emit diverse volatile blends that include bark beetle semiochemicals involved in mating and host localization. In this study, all 12 tested fungal isolates emitted beetle semiochemicals when growing in medium amended with linoleic acid. These semiochemicals included the spiroacetals chalcogran, trans-conophthorin and exo-brevicomin, as well as 2-methyl-3-buten-1-ol, the main aggregation pheromone component of the spruce bark beetle Ips typographus. The emission of these compounds was affected by the type of fatty acid present (linoleic vs. oleic acid). Accumulating evidence shows that the fatty acid composition in conifer bark can facilitate colonization by bark beetles and symbiotic fungi, whereas the fatty acid composition of non-host trees can be detrimental for beetle larvae or fungi. We hypothesize that beetles probe the fatty acid composition of potential host trees to test their suitability for beetle development and release of semiochemicals by symbiotic fungi.publishedVersio

Semiochemicals produced by fungal bark beetle symbiont Endoconidiophora rufipennis and the discovery of an anti-attractant for Ips typographus

Bark beetles vector symbiotic fungal species into their host trees during mass attacks. The symbiotic relationship with blue stain fungi of the Ascomycetes, including genera of Endoconidiophora (syn. = Ceratocystis), promotes successful establishment whereby the microbes help to overcome the host trees' defence and degrade toxic resins. This is the first study to evaluate both the volatile emissions from an insect-associated blue stain fungus over time and the insect response in a field trapping experiment. Volatile emissions from isolates of Endoconidiophora rufipennis (ER) were collected by solid-phase microextraction (SPME) and analysed by gas chromatography-mass spectroscopy (GC-MS) over a period of 30 days. This virulent North American fungus is closely related to E. polonica, a symbiotic fungus known from Eurasian spruce bark beetle Ips typographus.Nine volatiles were emitted by ER in substantial amounts: isoamyl acetate, sulcatone, 2-phenethyl acetate, geranyl acetone, geranyl acetate, citronellyl acetate, (R)- and (S)-sulcatol, and (R)-sulcatol acetate. A late peaking compound was geranyl acetone. In the field trapping experiment, three of the fungal volatiles (geranyl acetone, 2-phenethyl acetate and sulcatone) were tested in combination with a synthetic aggregation pheromone for I. typographus. Traps with geranyl acetone attracted lower numbers of I. typographus compared to traps with 2-phenethyl acetate, sulcatone or the pheromone alone as a control. The results showed that geranyl acetone acts as an anti-attractant and may act naturally on I. typographus as a cue from an associated fungus to signal an overexploited host

Non-host volatile blend optimization for forest protection against the European Spruce Bark Beetle, Ips typographus

Conifer feeding bark beetles (Coleoptera, Curculionidae, Scolytinae) pose a serious economic threat to forest production. Volatiles released by non-host angiosperm plants (so called non-host volatiles, NHV) have been shown to reduce the risk of attack by many bark beetle species, including the European spruce bark beetle, Ips typographus. However, the most active blend for I. typographus, containing three green leaf volatiles (GLVs) in addition to the key compounds trans-conophthorin (tC) and verbenone, has been considered too expensive for use in large-scale management. To lower the cost and improve the applicability of NHV, we aim to simplify the blend without compromising its anti-attractant potency. Since the key compound tC is expensive in pure form, we also tested a crude version: technical grade trans-conophthorin (T-tC). In another attempt to find a more cost effective substitute for tC, we evaluated a more readily synthesized analog: dehydroconophthorin (DHC). Our results showed that 1-hexanol alone could replace the three-component GLV blend containing 1- hexanol, (3Z)-hexen-1-ol, and (2E)-hexen-1-ol. Furthermore, the release rate of tC could be reduced from 5 mg/day to 0.5 mg/day in a blend with 1-hexanol and (–)-verbenone without compromising the anti-attractant activity. We further show that T-tC was comparable with tC, whereas DHC was a less effective anti-attractant. DHC also elicited weaker physiological responses in the tC-responding olfactory receptor neuron class, providing a likely mechanistic explanation for its weaker anti-attractive effect. Our results suggest a blend consisting of (–)-verbenone, 1-hexanol and technical transconophthorin as a cost-efficient anti-attractant for forest protection against I. typographus

Effects of Methyl Salicylate on Host Plant Acceptance and Feeding by the Aphid Rhopalosiphum padi

Methyl salicylate (MeSA) is a volatile shown to act as an inducer of plant defense against pathogens and certain herbivores, particularly aphids. It has been shown to have potential for aphid pest management, but knowledge on its mode of action is lacking, particularly induced plant-mediated effects. This study investigated the effects of exposing plants to MeSA on the host searching, host acceptance and feeding behavior of the bird cherry-oat aphid Rhopalosiphum padi. Barley plants were exposed to volatile MeSA for 24 h, after which biological effects were tested immediately after the exposure (Day 0), and then 1, 3 and 5 days after the end of the exposure. Aphid settling on MeSA-exposed plants was significantly reduced on days 0, 1 and 3, but not on day 5. In olfactometer tests, aphids preferred the odor of unexposed plants on days 1 and 3, but not on day 0 or 5. Analysis of volatiles from exposed and unexposed plants showed higher levels of MeSA from exposed plants, most likely absorbed and re-released from plant surfaces, but also specific changes in other plant volatiles on days 0, 1 and 3. High doses of MeSA did not affect aphid orientation in an olfactometer, but lower doses were repellent. Analysis of aphid feeding by Electronic penetration graph (EPG) showed that MeSA exposure resulted in resistance factors in barley plants, including surface factors and induced systemic factors in other tissues including the phloem. The results support the potential of MeSA as a potential tool for management of aphid pests

Odorant receptor phylogeny confirms conserved channels for sex pheromone and host plant signals in tortricid moths

The search for mates and food is mediated by volatile chemicals. Insects sense food odorants and sex pheromones through odorant receptors (ORs) and pheromone receptors (PRs), which are expressed in olfactory sensory neurons. Molecular phylogenetics of ORs, informed by behavioral and functional data, generates sound hypotheses for the identification of semiochemicals driving olfactory behavior. Studying orthologous receptors and their ligands across taxa affords insights into the role of chemical communication in reproductive isolation and phylogenetic divergence. The female sex pheromone of green budworm mothHedya nubiferana(Lepidoptera, Totricidae) is a blend of two unsaturated acetates, only a blend of both elicits male attraction. Females produce in addition codlemone, which is the sex pheromone of another tortricid, codling mothCydia pomonella. Codlemone also attracts green budworm moth males. Concomitantly, green budworm and codling moth males are attracted to the host plant volatile pear ester. A congruent behavioral response to the same pheromone and plant volatile in two tortricid species suggests co-occurrence of dedicated olfactory channels. In codling moth, one PR is tuned to both compounds, the sex pheromone codlemone and the plant volatile pear ester. Our phylogenetic analysis finds that green budworm moth expresses an orthologous PR gene. Shared ancestry, and high levels of amino acid identity and sequence similarity, in codling and green budworm moth PRs offer an explanation for parallel attraction of both species to the same compounds. A conserved olfactory channel for a sex pheromone and a host plant volatile substantiates the alliance of social and habitat signals in insect chemical communication. Field attraction assays confirm that in silico investigations of ORs afford powerful predictions for an efficient identification of behavior-modifying semiochemicals, for an improved understanding of the mechanisms of host plant attraction in insect herbivores and for the further development of sustainable insect control

Comparison of Phenylacetates with Benzoates and Phenylpropanoates as Antifeedants for the Pine Weevil, Hylobius abietis

This study concludes an extensive investigation of antifeedants for the pine weevil, Hylobius abietis (Coleoptera: Curculionidae), an economically important pest of planted conifer seedlings. Building on the previously reported antifeedant effects of benzoates and phenylpropanoids (aromatic compounds with one- or three-carbon-atom substituents on the benzene ring), we here report the antifeedant effects of compounds with two-carbon-atom side chains (i.e., phenylacetates). We also present new results; the best antifeedants from the benzoate class were tested at 10-fold lower concentrations in order to find the optimal antifeedants. Generally, for all three compound classes, efficient antifeedants were found to have one or two methyl, chloro, or methoxy substituents on the aromatic ring. For monosubstituted phenylpropanoids, the substituent preferably should be in the para-position. In the search for synergistic antifeedant effects among the three compound classes, combinations of compounds from the three classes were tested in binary and ternary mixtures.Bjorn Bohman was affiliated with Linnaeus University when the paper was published

Synthesis and characterization of the four geometrical isomers of 3,5-dodecadienyl acetate

Practical convergent syntheses of the four geometrical isomers of 3,5-dodecadienyl acetate are presented. These substances have been characterized by NMR and mass spectroscopy. (3E,5Z)-3,5-Dodecadienyl acetate is the main female sex pheromone component of the leaf roller Bonagota cranaodes, which is an important insect pest in apples in South America. The isomeric 3,5-dodecadienyl acetates, as pure isomers and in defined mixtures, have been used as trap lures for Eying insects in field screening experiments in Lithuania. Although no insects were found in the control traps, the numbers of males caught in the baited traps were not high enough to be statistically significant

Practical one-pot stereospecific preparation of vicinal and 1,3-diols

A facile one-pot synthesis providing vicinal diols and 1,3-diols in >95% stereoisomeric purity from com- mercially available enantiopure hydroxy esters has been developed. The esters were reduced with DIBALH and alkylated in situ with 4-pentenylmagnesium bromide, which after workup generated the title diols as diastereomeric pairs. These pairs were easily separated by preparative chromatography, affording products with retained stereoisomeric purity from the starting materials. This method represents an expedient preparation of many common natural products, such as cerambycid beetle pheromones and intermediates towards bicyclic acetal bark beetle pheromonesThis study was supported by Linnaeus University, Kalmar, Sweden. GRF gratefully acknowledges the Australian Research Council for funding (FT110100304

Flight and molecular modeling study on the response of codling moth, Cydia pomonella (Lepidoptera : Tortricidae) to (E,E)-8,10-dodecadien-1-ol and its geometrical isomers

In a previous study we have reported that both (E,Z)-8,10-dodecadienol (E,Z) and (Z,Z) 8,10-dodecadienol (Z,Z) isomers inhibit the attraction of male codling moth, Cydia pomonella L. when added to (E,E)-8,10-dodecadienol (E,E) while the (Z,E)-8,10-dodecadienol (Z,E) isomer induces slight increase in the number of males attracted to the pheromone source. In the present study, we have tested the behavioral activity of the individual geometrical isomers E,Z; Z,E and Z,Z. A few number of codling moth males flew to the Z,E-isomer while the other two isomers (i.e. E,Z and Z,Z) did not elicit any upwind orientation. Analysis of the Right behavior to the E,E- and Z,E-isomer showed significant differences in most of the flight parameters evaluated. Based on the biological observations and molecular modeling, we suggest that the behavioral activity of the Z,E-isomer is due to presence of specific receptors for this isomer on male antennae and not to its structural resemblance to the E,E-isomer. These results underline the importance of the Z,E-isomer in sex attraction of male codling moth