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1.
J Econ Entomol ; 117(3): 1032-1040, 2024 Jun 10.
Article in English | MEDLINE | ID: mdl-38625049

ABSTRACT

3-Hydroxyhexan-2-one (3-C6-ketol) has emerged as the most conserved pheromone structure within the beetle family Cerambycidae. In this study, we report the sex-specific production of this compound by males of 12 species of South American cerambycid beetles. Males of Chrysoprasis chalybea Redtenbacher and Mallosoma zonatum (Sahlberg) (Tribe Dichophyiini), and Ambonus lippus (Germar), Eurysthea hirta (Kirby), Pantonyssus nigriceps Bates, Stizocera plicicollis (Germar), and Stizocera tristis (Guérin-Méneville) (Elaphidiini) produced 3R-C6-ketol as a single component, whereas males of Neoclytus pusillus (Laporte & Gory) (Clytini), Aglaoschema concolor (Gounelle), Orthostoma abdominale (Gyllenhal) (Compsocerini), Dorcacerus barbatus (Olivier), and Retrachydes thoracicus thoracicus (Olivier) (Trachyderini) produced 3R-C6-ketol, along with lesser amounts of other compounds. In field trials testing 8 known cerambycid pheromone compounds, C. chalybea, E. hirta, and R. t. thoracicus were attracted in significant numbers to traps baited with 3-C6-ketol. A second field experiment provided support for the strategy of using the attraction of cerambycid species to test lures as a method of providing leads to their likely pheromone components. Because both sexes are attracted to these aggregation-sex pheromones, live beetles can be obtained from baited traps to verify they produce the compound(s) to which they were attracted, that is, that the compounds are indeed pheromone components.


Subject(s)
Coleoptera , Animals , Male , Female , Hexanones/pharmacology , Pheromones/pharmacology , Sex Attractants/pharmacology , Species Specificity , South America
2.
J Econ Entomol ; 117(3): 1001-1009, 2024 Jun 10.
Article in English | MEDLINE | ID: mdl-38555618

ABSTRACT

Male cerambycid beetles of the large subfamilies Cerambycinae and Lamiinae produce aggregation-sex pheromones that attract both sexes. The pheromones of many species are conserved among both closely related species (e.g., congeners) and more distantly related species (e.g., different subfamilies), including those endemic to different continents. This parsimony in pheromone structures suggests that multiple species may be attracted to traps baited with blends of pheromones, and such blends are finding use in delineating geographic ranges of native species and in surveillance programs for incursions of exotic species. Here, we present the results of a field experiment conducted at multiple sites in Iowa that tested the effects of deploying ethanol lures in tandem with a 6-component blend of common pheromone components for cerambycine and lamiine species and a 5-component blend that specifically targeted lamiines. Eight cerambycine species showed significant treatment effects, most of which were attracted to the 6-component blend, and ethanol increased attraction for half of these species. Two cerambycine species were attracted only by ethanol. Seven lamiine species were attracted by the lamiine-specific blend, alone or when combined with ethanol, and 3 of these species also were attracted to the 6-component blend. Taken together, these findings provide further evidence that carefully crafted blends of pheromones can be used to monitor the presence or abundance of multiple cerambycid species. Ethanol either increased the number of beetles attracted by pheromones or had no effect, so there is no apparent downside to deploying ethanol lures in combination with pheromones.


Subject(s)
Coleoptera , Ethanol , Insect Control , Sex Attractants , Animals , Coleoptera/drug effects , Male , Ethanol/pharmacology , Sex Attractants/pharmacology , Pheromones/pharmacology , Female , Iowa
3.
Environ Entomol ; 53(1): 101-107, 2024 Feb 20.
Article in English | MEDLINE | ID: mdl-38160262

ABSTRACT

As part of a long-term project on unraveling the use of pheromones in the large beetle family Cerambycidae, field trials were conducted with generic blends of known cerambycid pheromones at a desert site in southern California. In the first year of testing (2022), the species Eustromula valida (LeConte) (subfamily Cerambycinae, tribe Elaphidiini) and Aethecerinus latecinctus (Horn) (Cerambycinae, Trachyderini) were weakly attracted to one of the lure blends. In follow-up trials in 2023, only E. valida were caught, and collection of volatiles from both sexes of E. valida determined that males sex-specifically produced 3-methylthiopropan-1-ol (methionol), a compound that was not in the tested lure blends. Beetles of both sexes were strongly and specifically attracted to this compound in field bioassays, verifying that it is an aggregation-sex pheromone. No sympatric species were attracted to methionol while it was deployed in the field. Several recent studies have identified methionol as a pheromone component for other cerambycid species in both North and South America, suggesting it may represent another common pheromone component within the Cerambycidae.


Subject(s)
Coleoptera , Sex Attractants , Sulfides , Female , Male , Animals , Sex Attractants/pharmacology , Pheromones/pharmacology , Propanols
4.
Insects ; 14(11)2023 Nov 10.
Article in English | MEDLINE | ID: mdl-37999066

ABSTRACT

The longhorned beetle Rosalia batesi Harold (Coleoptera; Cerambycidae) is endemic to Japan, where its range extends from Hokkaido to Kyushu. The colorful adults are well-known to entomologists and collectors worldwide. It is a hardwood-boring species with larvae that develop in dead broad-leaf trees. In laboratory bioassays, females were attracted to males, which suggested that males produce a sex pheromone. The congeneric species R. alpina is native to Europe, and another congener, R. funebris, is distributed in North America. The pheromone components produced by males of these species had been previously identified as two compounds from different biosynthetic pathways. In the present study, volatiles were collected from beetles of both sexes, and the analyses of the resulting extracts revealed a single male-specific compound, which was identified as 3,5-dimethyl-6-(1-methylbutyl)-pyran-2-one; this is the same compound as the pheromone of the European R. alpina. This alkylated pyrone structure is, so far, unique among known cerambycid pheromones. In field bioassays with traps baited with the racemic synthetic pheromone, significant numbers of both sexes of R. batesi were attracted in an approximately equal ratio, indicating that the compound is an aggregation-sex pheromone rather than a sex pheromone.

5.
ACS Nano ; 17(18): 17634-17667, 2023 09 26.
Article in English | MEDLINE | ID: mdl-37677154

ABSTRACT

Soft bioelectronics play an increasingly crucial role in high-precision therapeutics due to their softness, biocompatibility, clinical accuracy, long-term stability, and patient-friendliness. In this review, we provide a comprehensive overview of the latest representative therapeutic applications of advanced soft bioelectronics, ranging from wearable therapeutics for skin wounds, diabetes, ophthalmic diseases, muscle disorders, and other diseases to implantable therapeutics against complex diseases, such as cardiac arrhythmias, cancer, neurological diseases, and others. We also highlight key challenges and opportunities for future clinical translation and commercialization of soft therapeutic bioelectronics toward personalized medicine.


Subject(s)
Electronics, Medical , Precision Medicine , Wearable Electronic Devices , Humans
6.
Front Bioeng Biotechnol ; 10: 922974, 2022.
Article in English | MEDLINE | ID: mdl-36003544

ABSTRACT

Plasticulture, the practice of using plastic materials in agricultural applications, consumes about 6.7 million tons of plastics every year, which is about 2% of the overall global annual plastics production. For different reasons, plastic material used for agriculture is difficult to recycle. Therefore, most of it is either buried in fertile soils, thereby significantly causing deterioration of their properties, or, at best case, end in landfills where its half-life is measured in decades and even centuries. Hence, developing biodegradable plastic materials that are suitable for agricultural applications is a vital and inevitable need for the global human society. In our labs, two types of potentially biodegradable plastic polymer films were prepared and characterized imidazolium in terms of their bio-degradability. In the first approach, polymers made of ionic liquid monomers were prepared using photo radical induced polymerization. The second approach relies on formation of polyethylene-like n-alkane disulfide polymers from 1,ω-di-thiols through thermally activated air oxidation. These two families of materials were tested for their biodegradability in soils by using a simulation system that combines a controlled environment chamber equipped with a respirometer and a proton-transfer-reaction time of flight mass spectrometer (PTR-TOF-MS) system. This system provides a time-dependent and comprehensive fingerprint of volatiles emitted in the degradation process. The results obtained thus far indicate that whereas the ionic-liquid based polymer does not show significant bio-degradability under the test conditions, the building block monomer, 1,10-n-decane dithiol, as well as its disulfide-based polymer, are bio-degradable. The latter reaching, under basic soil conditions and in room temperature, ∼20% degradation within three months. These results suggest that by introduction of disulfide groups into the polyethylene backbone one may be able to render it biodegradable, thus considerably shortening its half-life in soils. Principal component analysis, PCA, of the data about the total volatiles produced during the degradation in soil indicates a distinctive volatile "fingerprint" of the disulfide-based bio-degradable products which comes from the volatile organic compounds portfolio as recorded by the PTR-TOF-MS. The biodegradation volatile fingerprint of this kind of film was different from the "fingerprint" of the soil background which served as a control. These results can help us to better understand and design biodegradable films for agricultural mulching practices.

7.
J Nat Prod ; 85(8): 2062-2070, 2022 08 26.
Article in English | MEDLINE | ID: mdl-35877168

ABSTRACT

The leaffooted bugs Leptoglossus zonatus and L. occidentalis (Hemiptera: Coreidae) cause substantial damage in tree nut crops in North America and pine seed orchards in North America and Europe, respectively. Sexually mature males of both species produce a number of aldehydes, esters, and sesquiterpenes, which are hypothesized to constitute an aggregation pheromone attractive to both sexes. Among the volatiles produced by males of both species, we identified a unique sesquiterpene hydrocarbon, given the common name "leptotriene" (5), which elicited strong responses from antennae of both sexes in electroantennogram assays. Here, we report its structure and its synthesis from (-)-(E)-ß-caryophyllene (1).


Subject(s)
Heteroptera , Pinus , Sesquiterpenes , Animals , Female , Male , Seeds
8.
J Chem Ecol ; 48(5-6): 569-582, 2022 Jun.
Article in English | MEDLINE | ID: mdl-35501536

ABSTRACT

A novel trisubstituted tetrahydropyran was isolated and identified from the sex-specific volatiles produced by males of the cerambycid beetle Macropophora accentifer (Olivier), a serious pest of citrus and other fruit crops in South America. The compound was the major component in the headspace volatiles, and it was synthesized in racemic form. However, in field trials, the racemate was only weakly attractive to beetles of both sexes, suggesting that attraction might be inhibited by the presence of the "unnatural" enantiomer in the racemate. Alternatively, the male-produced volatiles contained a number of minor and trace components, including a compound tentatively identified as a homolog of the major component, as well as a number of unsaturated 8-carbon alcohols and aldehydes. Further work is required to conclusively identify and synthesize these minor components, to determine whether one or more of them are crucial components of the active pheromone blend for this species.


Subject(s)
Coleoptera , Sex Attractants , Spiders , Aldehydes , Animals , Female , Male , Pheromones , Sex Attractants/pharmacology
9.
Chem Commun (Camb) ; 57(98): 13341-13344, 2021 Dec 09.
Article in English | MEDLINE | ID: mdl-34817473

ABSTRACT

An arrayed combination of water-soluble deep cavitands and cationic dyes has been shown to optically sense insect pheromones at micromolar concentration in water. Machine learning approaches were used to optimize the most effective array components, which allows differentiation between small structural differences in targets, including between different diastereomers, even though the pheromones have no innate chromophore. When combined with chiral additives, enantiodiscrimination is possible, dependent on the size and shape of the pheromone.


Subject(s)
Pheromones/chemistry , Animals , Fluorescent Dyes , Insecta/chemistry , Machine Learning , Models, Molecular , Molecular Structure , Pheromones/isolation & purification , Stereoisomerism , Water/chemistry
10.
Environ Entomol ; 50(6): 1294-1298, 2021 12 17.
Article in English | MEDLINE | ID: mdl-34401912

ABSTRACT

A number of recent studies have demonstrated the potential for using blends of pheromones of cerambycid beetles to attract several species simultaneously. Here, we tested the effects of adding the pheromones of two invasive species, Trichoferus campestris (Faldermann) and Aromia bungii (Faldermann), on the attraction of native species to a generic blend of synthesized pheromones, in season-long field trials at 12 sites in Pennsylvania. Of the four species attracted in significant numbers, Megacyllene caryae (Gahan), Phymatodes amoenus (Say), and P. testaceus (L.) (all subfamily Cerambycinae) were not significantly affected by the addition of the T. campestris pheromone trichoferone and the A. bungii pheromone (E)-2-cis-6,7-epoxynonenal to the generic blend. In contrast, trap catches of Sternidius alpha (Say) (subfamily Lamiinae) were completely shut down by addition of the pheromones of the two exotic species. In addition, there was no indication that any native species were attracted to trichoferone or (E)-2-cis-6,7-epoxynonenal, suggesting that these pheromones are probably not used by species native to eastern North America.


Subject(s)
Coleoptera , Sex Attractants , Animals , Introduced Species , Pennsylvania , Pheromones/pharmacology , Seasons , Sex Attractants/pharmacology
11.
J Econ Entomol ; 113(5): 2269-2275, 2020 10 16.
Article in English | MEDLINE | ID: mdl-32696963

ABSTRACT

The wood-boring larvae of longhorned beetles (Coleoptera: Cerambycidae) can be important pests of woody plants, particularly as invasive species introduced by international commerce. Previous research has revealed that cerambycid species native to different parts of the world often share the same aggregation-sex pheromones and that pheromones of different species can be combined to create multi-species attractants that would be advantageous for surveillance monitoring for a number of species simultaneously. To explore the extent to which these chemicals can be combined into single lures, we developed four different blends of six to eight compounds and tested their effects as attractants for a community of longhorned beetle species in Iowa. The blends included known pheromones of species native to the study site, as well as pheromones identified from cerambycid species native to other parts of the world. The experiment confirmed that several cerambycid species were attracted by specific blends, in accordance with their known pheromone chemistry, and despite the presence of pheromone components of heterospecifics. This finding lends further support to developing multi-component blends that can effectively monitor for new incursions of multiple exotic species concurrently.


Subject(s)
Coleoptera , Sex Attractants , Animals , Iowa , Larva , Pheromones/pharmacology , Sex Attractants/pharmacology
12.
J Chem Ecol ; 46(5-6): 508-519, 2020 Jun.
Article in English | MEDLINE | ID: mdl-32506384

ABSTRACT

The Asian eulophid wasp Tetrastichus planipennisi is being released in North America as a biocontrol agent for the emerald ash borer (Agrilus planipennis), a very destructive invasive buprestid beetle that is devastating ash trees (Fraxinus spp.). We identified, synthesized, and tested a female-produced sex pheromone for the wasp. The key component eliciting behavioral responses from male wasps in flight tunnel bioassays was identified as (6S,10S)-(2E,4E,8E)-4,6,8,10-tetramethyltrideca-2,4,8-triene. Female specificity was demonstrated by gas chromatographic (GC) comparison of male and female volatile emissions and whole body extracts. The identification was aided by coupled gas chromatography/mass spectrometry analysis, microchemical reactions, NMR, GC analyses with a chiral stationary phase column, and matching GC retention times and mass spectra with those of synthetic standards. The tetramethyl-triene hydrocarbon was synthesized as a mixture of two enantiomeric pairs of diastereomers, and as the pure insect-produced stereoisomer. In flight-tunnel bioassays, males responded to both the natural pheromone and the chiral synthetic material by upwind flight and landing on the source. In contrast, the mixture of four stereoisomers was not attractive, indicating that one or more of the "unnatural" stereoisomers antagonized attraction. Field trials, using yellow pan traps baited with natural pheromone, captured significantly more male wasps than control traps over a four week trial. The identified pheromone could increase the efficiency and specificity of the current detection methods for Tetrastichus planipennisi and aid in the determination of parasitoid establishment at release sites.


Subject(s)
Sex Attractants/pharmacology , Wasps/chemistry , Animals , Coleoptera/parasitology , Female , Host-Parasite Interactions , Introduced Species , North America , Pest Control, Biological , Sex Attractants/chemical synthesis , Sex Attractants/isolation & purification , Wasps/physiology
13.
J Chem Ecol ; 46(1): 30-39, 2020 Jan.
Article in English | MEDLINE | ID: mdl-31808075

ABSTRACT

Cerambycid beetles of the subfamily Lamiinae use male-produced aggregation-sex pheromones that are attractive to both sexes. Terpenoid pheromones have been identified from species in the tribes Acanthoderini and Acanthocinini native to North and South America, comprised of (E)-6,10-dimethyl-5,9-undecadien-2-one (geranylacetone), the structurally related 6-methylhept-5-en-2-one (sulcatone), and/or specific enantiomers or nonracemic ratios of enantiomers of the related compounds (E)-6,10-dimethyl-5,9-undecadien-2-ol (fuscumol), its acetate ester, (E)-6,10-dimethyl-5,9-undecadien-2-yl acetate (fuscumol acetate), and 6-methylhept-5-en-2-ol (sulcatol). Here, we present new information about the chemical ecology of six acanthoderine and acanthocinine species native to the eastern USA. The pheromone of Astyleiopus variegatus (Haldeman) previously was identified as a blend of (S)-fuscumol and (S)-fuscumol acetate, and we report here that geranylacetone is a synergistic component. Males of Aegomorphus modestus (Gyllenhal), Lepturges angulatus (LeConte), and Lepturges confluens (Haldeman) were found to produce similar blends composed of the enantiomers of fuscumol acetate and geranylacetone, whereas males of Astylidius parvus (LeConte) and Sternidius alpha (Say) produced both enantiomers of fuscumol together with (R)-fuscumol acetate and geranylacetone. Field experiments with synthesized chemicals revealed that species with similar pheromone composition nevertheless differed in their responses to individual components, and to various blends of components, and in how attraction was influenced by chemicals that were pheromone components of other species. Sulcatone and/or sulcatol antagonized attraction of some species to pheromones of the geranylacetone class, suggesting that there is an adaptive advantage in an ability to detect these heterospecific compounds, such as in avoiding cross attraction to other cerambycid species, as yet unknown, that use pheromones composed of both chemical classes.


Subject(s)
Coleoptera/chemistry , Pheromones/chemistry , Animals , Coleoptera/metabolism , Female , Gas Chromatography-Mass Spectrometry , Male , Pheromones/isolation & purification , Pheromones/pharmacology , Sexual Behavior, Animal/drug effects , Species Specificity , Stereoisomerism , Terpenes/chemistry , Terpenes/isolation & purification , Terpenes/pharmacology , Volatile Organic Compounds/chemistry , Volatile Organic Compounds/isolation & purification , Volatile Organic Compounds/pharmacology
14.
J Med Entomol ; 57(3): 667-676, 2020 05 04.
Article in English | MEDLINE | ID: mdl-31837224

ABSTRACT

House flies (Musca domestica L.) are mechanical vectors of food-borne pathogens including Salmonella spp., Escherichia coli O157:H7, and Shigella spp., resulting in increased risk of diarrheal disease in areas where flies are abundant. Movement of house flies into food crops may be increased by the presence of honeydew-producing insects feeding on these crops. Using gas chromatography-electroantennogram detection (GC-EAD) and gas chromatography-mass spectrometry (GC-MS), volatile odors that elicited house fly antennal response were identified from naval orange (Osbeck) (Sapindales: Rutaceae) and Marsh grapefruit (Macfad.) (Sapindales: Rutaceae) leaves infested with whitefly (Hemiptera: Aleyrodidae) and from whole faba (L.) (Fabales: Fabaceae) bean plants infested with aphids (Hemiptera: Aphididae). Volatiles identified included benzaldehyde, butyl hexanoate, ß-caryophyllene, Δ3-carene, (E)-4,8-dimethyl-1,3,7-nonatriene (DMNT), (Z)-3-hexenyl acetate, myrcene, limonene, linalool, and naphthalene. This was followed by semifield bioassays of volatile blends and individual volatiles to determine house fly attraction to these volatiles. Although fly capture rates in the semifield setting were low, benzaldehyde and (Z)-3-hexenyl acetate were consistently attractive to house flies as individual compounds and as components of volatile blends.


Subject(s)
Arthropod Antennae/physiology , Houseflies/physiology , Magnoliopsida/chemistry , Pheromones/analysis , Volatile Organic Compounds/analysis , Animals , Aphids , Female , Hemiptera , Insect Vectors , Male , Odorants
15.
Sci Rep ; 9(1): 19570, 2019 12 20.
Article in English | MEDLINE | ID: mdl-31863031

ABSTRACT

The longhorned beetle Arhopalus rusticus (Coleoptera: Cerambycidae, Spondylinae) is a common species in conifer forests of the Northern Hemisphere, but with global trade, it has invaded and become established in New Zealand, Australia, and South America. Arhopalus rusticus is a suspected vector of the phytopathogenic nematode, Bursaphelenchus xylophilus, the causative agent of pine wilt disease, which is a major threat to pine forests worldwide. Here, we report the identification of a volatile, male-produced aggregation-sex pheromone for this species. Headspace odours from males contained a major male-specific compound, identified as (2 S, 5E)-6,10-dimethyl-5,9-undecadien-2-ol (common name (S)-fuscumol), and a minor component (E)-6,10-dimethyl-5,9-undecadien-2-one (geranylacetone). Both compounds are known pheromone components for species in the same subfamily. In field trials in its native range in Slovenia, (S)-fuscumol was significantly more attractive to beetles of both sexes, than racemic fuscumol and a blend of host plant volatiles commonly used as an attractant for this species. Fuscumol-baited traps also caught significant numbers of another spondylidine species, Spondylis buprestoides (L.), and a rare click beetle, Stenagostus rufus (De Geer). The pheromone can be exploited as a cost-effective and environmentally safe tool for detection and monitoring of this invasive species at ports of entry, and for monitoring the beetle's distribution and population trends in both endemic and invasive populations.


Subject(s)
Coleoptera/metabolism , Animals , Biological Assay , Female , Gas Chromatography-Mass Spectrometry , Male , Pheromones/metabolism , Slovenia , Terpenes/metabolism
16.
J Econ Entomol ; 112(5): 2236-2252, 2019 09 23.
Article in English | MEDLINE | ID: mdl-31136653

ABSTRACT

We present research on the chemical ecology of 14 species of longhorned beetles (Coleoptera: Cerambycidae), in four tribes of the subfamily Cerambycinae, conducted in east-central Illinois over 8 yr. Adult males produce aggregation-sex pheromones that attract both sexes. Twenty independent field bioassays explored the pheromone chemistry of the species and tested the possible attractive or antagonistic effects of compounds that are not produced by a given species, but are pheromone components of other species. Analyses of beetle-produced volatiles revealed compounds that had not been reported previously from several of the species. The most common pheromone component was (R)-3-hydroxyhexan-2-one, but pheromones of some species included isomers of the related 2,3-hexanediols. Males of the congeners Phymatodes amoenus (Say) and Phymatodes testaceus (L.) produced pure (R)-2-methylbutan-1-ol. Enantiomers of 2-methylbutan-1-ol also proved to be powerful synergists for Megacyllene caryae (Gahan), Sarosesthes fulminans (F.), and Xylotrechus colonus (F.). The major components of pheromone blends were consistently present in collections of headspace volatiles from male beetles, and only the major components were inherently attractive to a subset of species when tested as single components. Minor components of some species acted as powerful synergists, but in other cases appeared not to influence attraction. Among the minor components identified in headspace extracts from males, 2,3-hexanedione and 2-hydroxyhexan-3-one appeared to be analytical artifacts or biosynthetic by-products, and were neither attractants nor synergists. The antagonistic effects of minor compounds produced by heterospecific males suggest that these compounds serve to maintain prezygotic reproductive isolation among some species that share pheromone components.


Subject(s)
Coleoptera , Sex Attractants , Animals , Female , Illinois , Male , Pheromones , Sexual Behavior, Animal
17.
J Chem Ecol ; 45(4): 366-370, 2019 Apr.
Article in English | MEDLINE | ID: mdl-30931507

ABSTRACT

Insect pheromones have rarely been exploited in surveys or studies of rare and endangered species, despite their potential as effective and highly selective attractants for target species. Here, we report the identification, synthesis, and field bioassays of a male-produced aggregation-sex pheromone blend of a rare false click beetle species endemic to southern California, Dohrn's elegant eucnemid beetle, Palaeoxenus dohrni Horn (Coleoptera: Eucnemidae). This species is the only extant species in its genus and subfamily. Analyses of extracts of headspace volatiles collected from adult beetles revealed several male-specific compounds. Two of these compounds, identified as (E)-2-nonen-4-one and (R)-2-nonanol, elicited electroantennographic responses from antennae of beetles of both sexes. In field bioassays, a blend of the two compounds attracted both sexes, whereas the individual compounds were not attractive. The identification of an attractant pheromone should provide a useful tool for bioconservation and ecological studies of this iconic species.


Subject(s)
Alkenes/metabolism , Coleoptera/metabolism , Fatty Alcohols/metabolism , Sex Attractants/metabolism , Animals , Arthropod Antennae/physiology , Biological Assay , Female , Gas Chromatography-Mass Spectrometry , Male , Volatile Organic Compounds/metabolism
18.
Naturwissenschaften ; 106(5-6): 18, 2019 Apr 26.
Article in English | MEDLINE | ID: mdl-31028459

ABSTRACT

Plagionotus arcuatus ssp. arcuatus (L.) is a common saproxylic cerambycid beetle in most parts of Europe, and is designated as an occasional pest of oak wood that is stored outside during the summer months. In an effort to identify attractants that can be used for monitoring this species, we collected headspace samples from adult beetles and conducted field bioassays with the resulting compounds as potential aggregation-sex pheromone components for this species. Three compounds, (R)-3-hydroxyhexan-2-one, (R)-3-hydroxyoctan-2-one, and (R)-3-hydroxydecan-2-one, were consistently present in relatively large quantities in headspace extracts from male P. arcuatus populations in both Hungary and Sweden, regardless of the adsorbent media (activated charcoal or Porapak™ Q) used to sample beetle odors, or the type of solvent (hexane, diethyl ether, or dichloromethane) used to elute trapped volatiles from the collectors. None of the hydroxyketone and related compounds were detected in corresponding extracts from females. In field bioassays in both countries, the blend of the C6 and C10 compounds, and the ternary blend both attracted significantly more beetles than the control, while other combinations or single compounds were not significantly attractive. Males and females showed similar patterns of responses to treatments. Our results demonstrate that (R)-3-hydroxyhexan-2-one and (R)-3-hydroxydecan-2-one constitute a male-produced aggregation-sex pheromone of P. arcuatus, whereas the role of (R)-3-hydroxyoctan-2-one remains unclear. Lures with the pheromone could be developed for monitoring of P. arcuatus populations as an indicator of fresh oak wood resources.


Subject(s)
Coleoptera/physiology , Sex Attractants/isolation & purification , Animals , Coleoptera/chemistry , Coleoptera/drug effects , Female , Hungary , Male , Sex Attractants/chemistry , Sex Attractants/pharmacology , Sexual Behavior, Animal/drug effects , Sweden
19.
Sci Rep ; 9(1): 4459, 2019 03 14.
Article in English | MEDLINE | ID: mdl-30872772

ABSTRACT

The velvet longhorned beetle, Trichoferus campestris (Faldermann) ("VLB"; Coleoptera: Cerambycidae), is native to eastern Asia where it infests and damages a wide range of deciduous and coniferous tree species, including orchard and timber species. Immature stages of VLB are transported to new countries via international commerce, and populations have established outside the native range of the species. Here, we show that identification of pheromones of invasive pest species can be expedited by knowledge of the semiochemistry of related taxa. Histological sectioning revealed subcuticular, male-specific prothoracic glands connected to pits in the cuticle, which, in related species, are diagnostic for production of male-produced aggregation-sex pheromones, usually characterized by 2,3-alkanediol/hydroxyketone structural motifs. However, in preliminary field bioassays, beetles were not attracted by any known cerambycid pheromones. Subsequently, we identified a novel variant of the hydroxyketone motif ("trichoferone") from headspace volatiles of males. In field bioassays, synthetic trichoferone was more attractive to both sexes of VLB than previously developed high-release-rate ethanol lures, and attraction was strongly female biased. This study demonstrated the utility of the prothoracic gland trait for predicting pheromone use in cerambycid species in the subfamily Cerambycinae, and that identification of pheromones of novel species can be expedited by knowledge of pheromones of related species. Trichoferone should prove to be a valuable tool for detection of VLB in regions where the beetle is or may become established.


Subject(s)
Coleoptera/physiology , Sex Attractants/chemistry , Sex Attractants/pharmacology , Animals , Biological Assay , Coleoptera/anatomy & histology , Female , Introduced Species , Magnetic Resonance Spectroscopy , Male , Sex Attractants/chemical synthesis , Sex Attractants/metabolism , Stereoisomerism , Volatile Organic Compounds/analysis
20.
Environ Entomol ; 48(1): 189-192, 2019 02 13.
Article in English | MEDLINE | ID: mdl-30517617

ABSTRACT

During field bioassays in Kenya of 10 chemicals that are common pheromone components of cerambycid beetles, six species in the subfamily Cerambycinae were significantly attracted to 3-hydroxyhexan-2-one, and one species in the subfamily Lamiinae was significantly attracted to 2-(undecyloxy)ethanol (known as monochamol). These results further demonstrate that the former compound is highly conserved as a cerambycid pheromone because it has now been identified or implicated in the pheromones of numerous cerambycine species native to all six habitable continents. Similarly, monochamol has been identified or implicated as a pheromone component for species in the subfamily Lamiinae native to Asia, Europe, North America, and now Africa. The eight other compounds tested, including (E)-6,10-dimethyl-5,9-undecadien-2-ol (fuscumol), the corresponding (E)-6,10-dimethyl-5,9-undecadien-2-yl acetate (fuscumol acetate), syn- and anti-(2,3)-hexanediols and (2,3)-octanediols, 3-hydroxyoctan-2-one, and 3-hydroxydecan-2-one, did not attract significant numbers of any species.


Subject(s)
Coleoptera , Sex Attractants , Animals , Kenya
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