GC/MS analysis confirmed that neocembrene is the major component of the trail pheromone in the three species of the termite genus Prorhinotermes (P. simplex, P. canalifrons, P. inopinatus). In addition, EAG and GC-EAD experiments with P. simplex strongly suggest that dodecatrienol is a quantitatively minor component but a qualitatively important component of this trail pheromone. Trail-following bioassays confirmed the two-component nature of the trail pheromone. This is the first report of the use of the GC-EAD for the identification of trail pheromone in termites. These original results underline once again the special phylogenetic status of the Prorhinotermitinae among Rhinotermitidae.

• MeSH
• chromatografie plynová přístrojové vybavení   metody   MeSH
• feromony analýza   MeSH
• Isoptera chemie   MeSH
• zvířata MeSH
• Check Tag
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• hodnotící studie MeSH
• práce podpořená grantem MeSH
• Názvy látek
• feromony MeSH

Ceratitis fasciventris, Ceratitis anonae and Ceratitis rosa are polyphagous agricultural pests originating from the African continent. The taxonomy of this group (the so-called Ceratitis FAR complex) is unclear. To clarify the taxonomic relationships, male and female-produced volatiles presumably involved in pre-mating communication were studied using comprehensive two-dimensional gas chromatography with time-of-flight mass spectrometry (GC×GC-TOFMS) followed by multivariate analysis, and gas chromatography combined with electroantennographic detection (GC-EAD). GC×GC-TOFMS analyses revealed sex specific differences in produced volatiles. Male volatiles are complex mixtures that differ both qualitatively and quantitatively but share some common compounds. GC-EAD analyses of male volatiles revealed that the antennal sensitivities of females significantly differ in the studied species. No female volatiles elicited antennal responses in males. The results show clear species-specific differences in volatile production and provide complementary information for the distinct delimitation of the putative species by chemotaxonomic markers.

• Klíčová slova
• Ceratitis FAR complex, GC-EAD, GC×GC-TOFMS, chemotaxonomy, male and female-borne volatiles,
• Publikační typ
• časopisecké články MeSH

Bark beetles kill apparently vigorous conifers during epidemics by means of pheromone-mediated aggregation. During non-endemic conditions the beetles are limited to use trees with poor defense, like wind-thrown. To find olfactory cues that help beetles to distinguish between trees with strong or weak defense, we collected volatiles from the bark surface of healthy felled or standing Picea abies trees. Furthermore, living trees were treated with methyl jasmonate in order to induce defense responses. Volatiles were analyzed by combined gas chromatography and electroantennographic detection (GC-EAD) on Ips typographus antennae. Compounds eliciting antennal responses were characterized by single sensillum recording for identification of specific olfactory sensory neurons (OSN). Release of monoterpene hydrocarbons decreased, while oxygenated compounds increased, from spring to early summer in felled trees. In both beetle sexes particular strong EAD activity was elicited by trace amounts of terpene alcohols and ketones. 4-Thujanol gave a very strong response and the absolute configuration of the tested natural product was assigned to be (+)-trans-(1R,4S,5S)-thujanol by stereoselective synthesis and enantioselective gas chromatography. One type of OSN responded to all ketones and five other OSN were characterized by the type of compounds that elicited responses. Three new OSN classes were found. Of the eight EAD-active compounds found in methyl jasmonate-treated bark, the known anti-attractant 1,8-cineole was the one most strongly induced. Our data support the hypothesis that highly active oxygenated host volatiles could serve as positive or negative cues for host selection in I. typographus and in other bark beetles.

• Klíčová slova
• 4-thujanol, GC-EAD, Host chemistry, Oxygenated monoterpenes, Plant defense, SSR, Single-sensillum recordings, Styrene,
• MeSH
• acetáty farmakologie   MeSH
• bicyklické monoterpeny MeSH
• brouci fyziologie   MeSH
• cyklopentany farmakologie   MeSH
• elektrofyziologické jevy účinky léků   MeSH
• kůra rostlin chemie   účinky léků   metabolismus   MeSH
• monoterpeny chemická syntéza   chemie   farmakologie   MeSH
• oxylipiny farmakologie   MeSH
• plynová chromatografie s hmotnostně spektrometrickou detekcí MeSH
• smrk chemie   metabolismus   MeSH
• stereoizomerie MeSH
• styren chemie   farmakologie   MeSH
• zvířata MeSH
• Check Tag
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• 2-methyl-5-(1-methylethyl)bicyclo(3.1.0)hexan-2-ol MeSH Prohlížeč
• acetáty MeSH
• bicyklické monoterpeny MeSH
• cyklopentany MeSH
• methyl jasmonate MeSH Prohlížeč
• monoterpeny MeSH
• oxylipiny MeSH
• styren MeSH

Conventional gas chromatography with electroantennographic detection (GC-EAD) and two-dimensional (GCxGC) gas chromatography using a time-of-flight mass spectrometric detector (TOFMS), were combined to analyse the female sex pheromone gland extract of the persimmon bark borer, Euzophera batangensis. GC-EAD analysis produced two EAD responses in GC areas where no compounds were detected by FID detection. GCxGC/TOFMS analysis of this area indicated the presence of several chemicals, including (Z9,E12)-tetradeca-9,12-dien-1-ol and (Z9)-tetradec-9-en-1-ol, pheromone components of closely related Euzophera species. Spectral characteristics, retention behaviour and the ability to elicit GC-EAD responses imply that both identified unsaturated alcohols are candidates for E. batangensis sex pheromone components. GCxGC/TOFMS facilitated the analysis of complex matrices on a subnanogram level and was shown to have great potential as a powerful tool in the analysis of insect pheromones.

• Publikační typ
• časopisecké články MeSH

The medfly (Ceratitis capitata) is one of the major agricultural pests controlled through sterile insect technique (SIT) programs. We studied the chemical composition of the volatiles released by calling males from one laboratory and two wild C. capitata populations using two-dimensional gas chromatography with time-of-flight mass spectrometric detection (GC × GC/TOFMS) and gas chromatography with electroantennographic detection (GC-EAD). Multivariate data analyses revealed significant differences in the quantitative and qualitative composition of male chemical emanations between the three populations. The GC-EAD analyses of the male emanation of three C. capitata populations revealed 14 antenally active compounds. The volatiles isomenthone, β-pinene, ethyl octanoate, indole, geraniol, bornyl acetate, geranyl acetone, and (E)-caryophyllene are newly reported EAD active constituents of the male pheromone. GC-EAD analyses of the laboratory population indicated that the males and females of C. capitata possess comparable sensitivity to male-produced volatiles. Our results are relevant to the development of a pheromone-based monitoring system and also to the SIT control program.

• MeSH
• Ceratitis capitata metabolismus   MeSH
• chromatografie plynová MeSH
• hmotnostní spektrometrie MeSH
• laboratorní zvířata MeSH
• plynová chromatografie s hmotnostně spektrometrickou detekcí MeSH
• sexuální lákadla chemie   MeSH
• těkavé organické sloučeniny analýza   MeSH
• zvířata MeSH
• Check Tag
• mužské pohlaví MeSH
• ženské pohlaví MeSH
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• srovnávací studie MeSH
• Názvy látek
• sexuální lákadla MeSH
• těkavé organické sloučeniny MeSH

Gas chromatography combined with electroantennographic detection (GC-EAD), electroantennography (EAG), and wind-tunnel and field experiments were used to reinvestigate the composition of Cameraria ohridella (Lepidoptera, Gracillariidae, Lithocolletinae) sex pheromone. The GC-EAD experiments showed one EAD-active area corresponding to the major pheromone component. (8E,10Z)-tetradeca-8,10-dienal. The EAG experiments proved that (9E)-tetracedecenal and stereoisomers of (8E,10Z)-tetradeca-8,10-dienal exhibited significant electrophysiological activity and could, therefore, be considered as possible minor pheromone components. However, wind-tunnel and field experiments demonstrated that none of these compounds affect the efficacy of the main pheromone component. A monitoring system based on (8E,10Z)tetradeca-8,10-dienal was developed and used to study the flight activity of C. ohridella.

• MeSH
• chromatografie plynová MeSH
• elektrofyziologie MeSH
• Lepidoptera chemie   MeSH
• let zvířat MeSH
• monitorování životního prostředí MeSH
• populační dynamika MeSH
• sexuální lákadla farmakologie   MeSH
• stereoizomerie MeSH
• vítr MeSH
• zvířata MeSH
• Check Tag
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• sexuální lákadla MeSH

Male wing gland secretion and volatiles emanating from calling males were investigated in the bumble bee wax moth, Aphomia. sociella, using comprehensive two-dimensional gas chromatography-mass spectrometry (GCxGC-TOF-MS), gas chromatography-infrared spectroscopy (GC-FTIR), enantioselective gas chromatography, electroantennography (EAG), gas chromatography with electroantennographic detection (GC-EAD), and NMR. GC-EAD analysis of the male wing gland secretion revealed seven active areas, corresponding to 1-hexanol (1), 2-phenylethanol (2), [(R),(Z)]-nona-2,6-dien-4-olide (3), [(S),(Z)]-nona-6-en-4-olide (4), mellein (5), phytone (6), and a mixture of C(18) fatty acids (7). Solid-phase microextraction (SPME) confirmed the presence of 2-phenylethanol, nona-2,6-dien-4-olide, nona-6-en-4-olide, mellein, and phytone in volatiles emanating from a calling male. Though the abundance of these compounds slightly differed in SPME and gland secretion analysis, nona-2,6-dien-4-olide and mellein dominated in both samples, followed by 2-phenylethanol, nona-6-en-4-olide, and phytone. The strong antennal responses elicited by components of the secretion suggest that one or more of these compounds constitute the sex pheromone. Both sexes perceived male wing gland secretion, with females being significantly more sensitive compared to males.

• MeSH
• chování zvířat fyziologie   MeSH
• fenethylalkohol chemie   izolace a purifikace   MeSH
• hexanoly chemie   izolace a purifikace   MeSH
• isokumariny chemie   izolace a purifikace   MeSH
• křídla zvířecí metabolismus   MeSH
• mastné kyseliny chemie   izolace a purifikace   MeSH
• molekulární struktura MeSH
• můry * chemie   fyziologie   MeSH
• ochratoxiny chemie   izolace a purifikace   MeSH
• plynová chromatografie s hmotnostně spektrometrickou detekcí MeSH
• sexuální lákadla fyziologie   MeSH
• stereoizomerie MeSH
• včely parazitologie   MeSH
• zvířata MeSH
• Check Tag
• mužské pohlaví MeSH
• ženské pohlaví MeSH
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• 1-hexanol MeSH Prohlížeč
• fenethylalkohol MeSH
• hexanoly MeSH
• isokumariny MeSH
• mastné kyseliny MeSH
• ochracin MeSH Prohlížeč
• ochratoxiny MeSH
• sexuální lákadla MeSH

Aphomia sociella (Lepidoptera: Pyralidae: Galleriinae) is a parasitic moth of bumblebees. Behavioral experiments show that A. sociella females emit semiochemicals that influence male pre-mating behavior and serve as a courtship pheromone. GC/EAD and two-dimensional GC/MS (GCxGC-TOFMS) analyses of extracts of females revealed three antennally active compounds. Comparative GC and GCxGC-TOFMS analyses of extracts and synthetic standards confirmed the identity of the antennally active compounds as hexan-1-ol (1), 6,10,14-trimethylpentadecan-2-one (2), and 6,10,14-trimethylpentadecan-2-ol (3). In laboratory bioassays, alcohol 3 and, at higher doses, ketone 2 initiated male courtship behavior associated with ultrasonic production. Hexan-1-ol (1) and ketone 2 enhanced the activity of alcohol 3. These data suggest that hexan-1-ol, 6,10,14-trimethylpentadecan-2-ol, and 6,10,14-trimethylpentadecan-2-one constitute the female-produced courtship pheromone of A. sociella.

• MeSH
• komunikace zvířat MeSH
• Lepidoptera metabolismus   MeSH
• námluvy * MeSH
• sexuální chování zvířat účinky léků   MeSH
• sexuální lákadla metabolismus   farmakologie   MeSH
• těkavé organické sloučeniny metabolismus   farmakologie   MeSH
• včely parazitologie   MeSH
• zvířata MeSH
• Check Tag
• mužské pohlaví MeSH
• ženské pohlaví MeSH
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• sexuální lákadla MeSH
• těkavé organické sloučeniny MeSH

The asymmetric total synthesis of the diastereomers of stylopsal establishes the absolute configuration of the first reported sex pheromone of the twisted-wing parasite Stylops muelleri as (3R,5R,9R)-trimethyldodecanal. The key steps for the diastereo- and enantiodivergent introduction of the methyl groups are two different types of asymmetric conjugate addition reactions of organocopper reagents to α,β-unsaturated esters, whereas the dodecanal skeleton is assembled by Wittig reactions. The structure of the natural product was confirmed by chiral gas chromatography (GC) techniques, GC/MS and GC/electroantennography (EAD) as well as field tests. An investigation into the biosynthesis of the pheromone revealed that it is likely to be produced by decarboxylation of a 4,6,10-trimethyltridecanoic acid derivative, which was found in substantial amounts in the fat body of the female, but not in the host bee Andrena vaga. This triple-branched fatty acid precursor thus seems to be biosynthesized de novo through a polyketide pathway with two consecutive propionate-propionate-acetate assemblies to form the complete skeleton. The simplified, motionless and fully host-dependent female exploits a remarkable strategy to maximize its reproductive success by employing a relatively complex and potent sex pheromone.

• MeSH
• aldehydy chemická syntéza   chemie   farmakologie   MeSH
• chování zvířat účinky léků   MeSH
• esterifikace MeSH
• nitrily chemie   MeSH
• plynová chromatografie s hmotnostně spektrometrickou detekcí MeSH
• sexuální lákadla chemická syntéza   chemie   farmakologie   MeSH
• stereoizomerie MeSH
• včely chemie   MeSH
• zvířata MeSH
• Check Tag
• mužské pohlaví MeSH
• ženské pohlaví MeSH
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• 3,5,9-trimethyldodecanal MeSH Prohlížeč
• aldehydy MeSH
• nitrily MeSH
• sexuální lákadla MeSH

Ancistrotermes dimorphus is a common Macrotermitinae representative, facultative inquiline by its life-style, occurring in South-East China. Sex pheromone is used for couple formation and maintenance, and it is produced by and released from the female sternal gland and is highly attractive to males. Based on our combined behavioral, chemical and electrophysiological analyses, we identified (3Z,6Z)-dodeca-3,6-dien-1-ol as the female sex pheromone of A. dimorphus as it evoked the tandem behavior at short distance, and the active quantities ranged from 0.01ng to 10ng. Interestingly, GC-MS analyses of SPME extracts showed another compound specific to the female sternal gland, (3Z)-dodec-3-en-1-ol, which showed a clear GC-EAD response. However, this compound has no behavioral function in natural concentrations (0.1ng), while higher amounts (1ng) inhibit the attraction achieved by (3Z,6Z)-dodeca-3,6-dien-1-ol. The function of (3Z)-dodec-3-en-1-ol is not fully understood, but might be linked to recognition from sympatric species using the same major compound, enhancing the long-distance attraction, or informing about presence of other colonies using the compound as a trail-following pheromone. The sternal gland secretion of Ancistrotermes females contains additional candidate compounds, namely (3E,6Z)-dodeca-3,6-dien-1-ol and (6Z)-dodec-6-en-1-ol, which are not perceived by males' antennae in biologically relevant amounts.

• Klíčová slova
• (3Z)-Dodec-3-en-1-ol, (3Z,6Z)-Dodeca-3,6-dien-1-ol, Courtship behavior, Fungus-growing termite,
• MeSH
• elektrofyziologické jevy účinky léků   MeSH
• Isoptera chemie   fyziologie   MeSH
• sexuální chování zvířat účinky léků   MeSH
• sexuální lákadla chemie   izolace a purifikace   farmakologie   MeSH
• tykadla členovců fyziologie   MeSH
• zvířata MeSH
• Check Tag
• mužské pohlaví MeSH
• ženské pohlaví MeSH
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Geografické názvy
• Čína MeSH
• Názvy látek
• sexuální lákadla MeSH