Publications (11)26.73 Total impact
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Article: Total Synthesis, Proof of Absolute Configuration, and Biosynthetic Origin of Stylopsal, the First Isolated Sex Pheromone of Strepsiptera.
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ABSTRACT: 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.Chemistry 04/2013; · 5.93 Impact Factor -
Dataset: 145 Tendon NAWI 2012
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Article: Stylopsal: The First Identified Female-produced Sex Pheromone of Strepsiptera.
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ABSTRACT: A female-produced sex pheromone of Stylops muelleri was identified as an unusually branched saturated aldehyde (9R)-3,5-syn-3,5,9-trimethyldodecanal. We named it stylopsal. Its structure was established by using mass spectrometry, infrared spectroscopy, and organic synthesis of candidate compounds. The synthetic standard of (9R)-3,5-syn-3,5,9-trimethyldodecanal gave identical chromatographic and mass spectrometric data as the natural pheromone and also was active in electroantennographic and behavioral assays. The female fat body lipids contained the corresponding fatty acid, indicating a possible link between lipid metabolism and the pheromone biosynthesis.Journal of Chemical Ecology 11/2012; 38(12):1483-1491. · 2.66 Impact Factor -
Article: Leg tendon glands in male bumblebees (Bombus terrestris): structure, secretion chemistry, and possible functions.
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ABSTRACT: Among the large number of exocrine glands described in bees, the tarsal glands were thought to be the source of footprint scent marks. However, recent studies showed that the compounds used for marking by stingless bees are secreted by leg tendon instead of tarsal glands. Here, we report on the structure of leg tendon glands in males of Bombus terrestris, together with a description of the chemical composition of their secretions and respective changes of both during the males' lives. The ultrastructure of leg tendon glands shows that the secretory cells are located in three independent regions, separated from each other by unmodified epidermal cells: in the femur, tibia, and basitarsus. Due to the common site of secretion release, the organ is considered a single secretory gland. The secretion of the leg tendon glands of B. terrestris males differs in its composition from those of workers and queens, in particular by (1) having larger proportions of compounds with longer chain lengths, which we identified as wax esters; and (2) by the lack of certain hydrocarbons (especially long chain dienes). Other differences consist in the distribution of double bond positions in the unsaturated hydrocarbons that are predominantly located at position 9 in males but distributed at seven to nine different positions in the female castes. Double bond positions may change chemical and physical properties of a molecule, which can be recognized by the insects and, thus, may serve to convey specific information. The function of male-specific compounds identified from their tendon glands remains elusive, but several possibilities are discussed.Naturwissenschaften 10/2012; · 2.28 Impact Factor -
Article: Sex Pheromone and Trail Pheromone of the Sand Termite Psammotermes hybostoma
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ABSTRACT: Within the complex network of chemical signals used by termites, trail pheromones and sex pheromones are among the best known. Numerous recent papers map the chemical identity and glandular origin of these pheromones in nearly all major isopteran taxa. In this study, we aimed to describe the sex pheromone and the trail pheromone of a poorly known sand termite, Psammotermes hybostoma. We identified (3Z,6Z,8E)-dodeca-3,6,8-trien-1-ol (dodecatrienol) as the sex pheromone released by tergal and sternal glands of female imagos and, at the same time, as the trail pheromone secreted from the sternal gland of workers. We conclude that chemical communication in Psammotermes does not differ from that of most other Rhinotermitidae, such as Reticulitermes, despite the presence of a diterpene as a major component of the trail pheromone of Prorhinotermes to which Psammotermes is presumed to be phylogenetically close. Our findings underline once again the conservative nature of chemical communication in termites, with dodecatrienol being a frequent component of pheromonal signals in trail following and sex attraction and, at the same time, a tight evolutionary relationship between the trail following of working castes and the sex attraction of imagos. Key WordsSex pheromone–Trail pheromone– Psammotermes hybostoma –Termites–Rhinotermitidae–Tergal glands–Sternal gland–GC-EAD–Dodecatrienol–Timber pestJournal of Chemical Ecology 04/2012; 37(2):179-188. · 2.66 Impact Factor -
Article: Females of the bumblebee parasite, Aphomia sociella, excite males using a courtship pheromone.
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ABSTRACT: 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.Journal of Chemical Ecology 04/2012; 38(4):400-7. · 2.66 Impact Factor -
Article: Developmental Pathways of Psammotermes hybostoma (Isoptera: Rhinotermitidae): Old Pseudergates Make up a New Sterile Caste.
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ABSTRACT: Ergonomic efficiency is in termites maximized by task partitioning among specialized castes. The isopteran caste systems can be classified as either (i) linear, when tasks are performed by pluripotent immatures (pseudergates), retaining the ability to develop into winged imagoes or (ii) bifurcated, with the presence of a true worker caste, which diverges early and permanently from the sexual (nymph/alate) line. Here, we report on the ontogenetic potentialities of the highly polymorphic sand termite Psammotermes hybostoma. Beside numerous pluripotent pseudergates, constituting the main work force, some larger non-feeding apterous immatures, also occur. These individuals are unable to proceed to the winged imago stage, but store large amounts of fat and also give rise to large soldiers. Soldiers therefore originate from a wide range of apterous instars, consequently being highly polymorphic. The caste system of P. hybostoma is essentially linear, as in other basal Rhinotermitidae, but is distinguished by the late bifurcation leading to large apterous immatures. Because these large worker-like individuals deviate late and do not perform worker tasks, they cannot be considered homologous to the true workers of Termitidae and advanced Rhinotermitidae, but they provide a novel example of the evolution of sterile immatures in termites.PLoS ONE 01/2012; 7(9):e44527. · 4.09 Impact Factor -
Article: Nonadecadienone, a new termite trail-following pheromone identified in Glossotermes oculatus (Serritermitidae).
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ABSTRACT: Within the multitude of chemical signals used by termites, the trail marking by means of pheromones is ubiquitous. Chemistry and biology of the trail-following communication have been described in more than 60 species from all families except for the Neotropical Serritermitidae. The chemical ecology of Serritermitidae is of special interest not only as a missing piece of knowledge on the diversity and evolution of isopteran pheromones but also because it may contribute to the debate on the phylogenetic position of this family, which is still unresolved. Therefore, we aimed in this study to identify the trail-following pheromone of the serritermitid Glossotermes oculatus. Based on a combined approach of analytical chemistry, electrophysiology, and behavioral bioassays, we propose (10Z,13Z)-nonadeca-10,13-dien-2-one to be the trail-following pheromone of G. oculatus, secreted by the sternal gland of pseudergates. Thus, we report on a new termite trail-following pheromone of an unexpected chemical structure, a ketone with 19 carbons, contrasting with unsaturated alcohols containing 12 carbons as trail-following pheromones in other advanced termite families. In addition to this unique trail-following pheromone, we also describe the sternal gland in pseudergates as an organ of unusual shape, size, and structure when compared with other isopteran species. These results underline the peculiarity of the family Serritermitidae and prompt our interest in the chemistry of pheromones in the other genus of the family, Serritermes.Chemical Senses 08/2011; 37(1):55-63. · 2.60 Impact Factor -
Article: Changes in the composition of triacylglycerols in the fat bodies of bumblebee males during their lifetime.
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ABSTRACT: The age-dependent changes in the composition of triacylglycerols (TAG) in the fat bodies of bumblebee males were studied using HPLC/MS. Two related species (Bombus terrestris and B. lucorum) were compared, with the age of the males being 0-30 days. The total amount of TAG in B. lucorum was about 2.7 times higher than that in B. terrestris for all of the ages studied. One to three-day-old males had the highest content of TAG in their fat bodies (1.6-2.3 mg/individual in B. terrestris and 3.8-4.2 mg/individual in B. lucorum). The analytical data show different patterns in both species. The qualitative composition of fatty acids in TAG was similar, but the mean relative abundance between B. terrestris and B. lucorum differed: 14:0, 7 and 14%; 16:0, 20 and 44%; 18:3, 62 and 23%; 18:1, 3 and 8%, respectively (the data is based on a GC/MS integration). A statistical evaluation of the dynamic changes in the TAG composition revealed that in B. terrestris different age classes were well separated according to their TAG composition while in B. lucorum the TAG did not change substantially during the male's life. The TAG analyses provide more precise information on the differences between the classes studied than the FA composition alone.Lipids 07/2011; 46(9):863-71. · 2.13 Impact Factor -
Article: Analysis of insect triacylglycerols using liquid chromatography‐atmospheric pressure chemical ionization‐mass spectrometry
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ABSTRACT: An HPLC non-aqueous reversed-phase separation system was adapted for analyzing insect triacylglycerols (TAG). The method uses two conventional Nova-Pak C18 columns connected in series, for a total length of 45 cm. The mobile phase gradient is mixed from acetonitrile and 2-propanol, and the flow rate is programmed from 1.0 to 0.7 mL/min. TAG are detected by atmospheric pressure chemical ionization-mass spectrometry. The method ensures efficient separation of isomers and analysis of high-molecular-weight TAG with equivalent chain lengths up to 72. The method performance is demonstrated on analysis of TAG isolated from the fat body of the bumblebee Bombus lucorum.European Journal of Lipid Science and Technology 05/2009; 111(5):519 - 525. · 1.73 Impact Factor -
Article: GC×GC/TOF MS technique—A new tool in identification of insect pheromones: Analysis of the persimmon bark borer sex pheromone gland
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ABSTRACT: Conventional gas chromatography with electroantennographic detection (GC-EAD) and two-dimensional (GC × GC) 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. GC × GC/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. GC × GC/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.Talanta.
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Institutions
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2012
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Universität Ulm
- Institute of Experimental Ecology of Animals
Ulm, Baden-Wuerttemberg, Germany
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2009–2011
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Academy of Sciences of the Czech Republic
- Ústav organické chemie a biochemie
Praha, Hlavni mesto Praha, Czech Republic
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