@article{eliyahu_nojima_santangelo_carpenter_webster_kiemle_gemeno_leal_schal_2011, title={Unusual macrocyclic lactone sex pheromone of Parcoblatta lata, a primary food source of the endangered red-cockaded woodpecker}, volume={109}, ISSN={0027-8424 1091-6490}, url={http://dx.doi.org/10.1073/pnas.1111748109}, DOI={10.1073/pnas.1111748109}, abstractNote={
            Wood cockroaches in the genus
            Parcoblatta
            , comprising 12 species endemic to North America, are highly abundant in southeastern pine forests and represent an important prey of the endangered red-cockaded woodpecker,
            Picoides borealis
            . The broad wood cockroach,
            Parcoblatta lata
            , is among the largest and most abundant of the wood cockroaches, constituting >50% of the biomass of the woodpecker's diet. Because reproduction in red-cockaded woodpeckers is affected dramatically by seasonal and spatial changes in arthropod availability, monitoring
            P. lata
            populations could serve as a useful index of habitat suitability for woodpecker conservation and forest management efforts. Female
            P. lata
            emit a volatile, long-distance sex pheromone, which, once identified and synthesized, could be deployed for monitoring cockroach populations. We describe here the identification, synthesis, and confirmation of the chemical structure of this pheromone as (4
            Z
            ,11
            Z
            )-oxacyclotrideca-4,11-dien-2-one [= (3
            Z
            ,10
            Z
            )-dodecadienolide; herein referred to as “parcoblattalactone”]. This macrocyclic lactone is a previously unidentified natural product and a previously unknown pheromonal structure for cockroaches, highlighting the great chemical diversity that characterizes olfactory communication in cockroaches: Each long-range sex pheromone identified to date from different genera belongs to a different chemical class. Parcoblattalactone was biologically active in electrophysiological assays and attracted not only
            P. lata
            but also several other
            Parcoblatta
            species in pine forests, underscoring its utility in monitoring several endemic wood cockroach species in red-cockaded woodpecker habitats.
          }, number={8}, journal={Proceedings of the National Academy of Sciences}, publisher={Proceedings of the National Academy of Sciences}, author={Eliyahu, D. and Nojima, S. and Santangelo, R. G. and Carpenter, S. and Webster, F. X. and Kiemle, D. J. and Gemeno, C. and Leal, W. S. and Schal, C.}, year={2011}, month={Dec}, pages={E490–E496} }
 @article{eliyahu_nojima_mori_schal_2009, title={Jail baits: how and why nymphs mimic adult females of the German cockroach, Blattella germanica}, volume={78}, ISSN={["1095-8282"]}, DOI={10.1016/j.anbehav.2009.06.035}, abstractNote={The male German cockroach performs a characteristic courtship behaviour upon contacting a sexually receptive female: he turns away from the female and raises his wings, thereby exposing tergal glands whose reservoirs contain phagostimulatory substances. The female then mounts the male and feeds upon these nuptial secretions; this behaviour places her in the appropriate precopulatory position. The contact sex pheromone on the cuticular surface of the female, responsible for eliciting courtship behaviour in males, consists of a blend of six components that share a common biosynthetic pathway. An excised female antenna can elicit the full courtship display in males. We found that antennae taken from either male or female nymphs of various ages also could elicit the full courtship response in adult males. We extracted lipids from the cuticular surface of nymphs and, guided by behavioural assays, we fractionated the extracts using various chromatography procedures, including flash (column) chromatography, high-performance liquid chromatography and gas chromatography. Mass spectrometry analysis of behaviourally active fractions revealed two classes of courtship-eliciting compounds: all nymphs possessed a novel, still unidentified compound that elicited courtship in adult males. In addition, in last-instar females, we isolated four of the six adult female-specific contact sex pheromone components, consistent with differentiation of the sexes at this stage, and the onset of sexual maturation of the pheromone biosynthetic machinery. Our results support the interpretation that nymphs engage in sexual mimicry to gain access to male-produced nuptial tergal secretions that are exposed and can be secured only during courtship.}, number={5}, journal={ANIMAL BEHAVIOUR}, author={Eliyahu, Dorit and Nojima, Satoshi and Mori, Kenji and Schal, Coby}, year={2009}, month={Nov}, pages={1097–1105} }
 @article{fan_eliyahu_schal_2008, title={Cuticular hydrocarbons as maternal provisions in embryos and nymphs of the cockroach Blattella germanica}, volume={211}, ISSN={["0022-0949"]}, DOI={10.1242/jeb.009233}, abstractNote={SUMMARY}, number={4}, journal={JOURNAL OF EXPERIMENTAL BIOLOGY}, author={Fan, Yongliang and Eliyahu, Dorit and Schal, Coby}, year={2008}, month={Feb}, pages={548–554} }
 @article{eliyahu_nojima_capracotta_comins_schal_2008, title={Identification of cuticular lipids eliciting interspecific courtship in the German cockroach, Blattella germanica}, volume={95}, ISSN={["1432-1904"]}, DOI={10.1007/s00114-007-0339-7}, abstractNote={The cuticular surface of sexually mature females of the German cockroach contains a sex pheromone that, upon contact with the male's antennae, elicits a characteristic species-specific courtship behavior. This female-specific pheromone is a blend of several long-chain methyl ketones, alcohols and aldehydes, all derived from prominent cuticular hydrocarbons found in all life stages of this cockroach. We found that contact with the antennae of 5 out of 20 assayed cockroach species elicited courtship behavior in German cockroach males. The heterospecific courtship-eliciting compounds were isolated by behaviorally guided fractionation of the active crude extracts and compared to the native sex pheromone components. We identified two active compounds from the cuticular extract of the Oriental cockroach, Blatta orientalis -- 11-methylheptacosan-2-one and 27-oxo-11-methylheptacosan-2-one; the former compound was confirmed by synthesis and proved to independently stimulate courtship in German cockroach males. These compounds share common features with, but are distinct from, any of the known contact sex pheromone components. This suggests that sex pheromone reception in the male German cockroach is unusually promiscuous, accepting a wide range of compounds that share certain features with its native pheromone, thus resulting in a broad spectrum of behavioral response to other species. We propose that several characteristics of their mating system -- chiefly, absence of closely related species in the anthropogenic environment, resulting in relaxation of selection on sexual communication, and a highly male-biased operational sex ratio -- have driven males to respond with extremely low thresholds to a wide spectrum of related compounds.}, number={5}, journal={NATURWISSENSCHAFTEN}, author={Eliyahu, Dorit and Nojima, Satoshi and Capracotta, Sonja S. and Comins, Daniel L. and Schal, Coby}, year={2008}, month={May}, pages={403–412} }
 @article{eliyahu_nojima_mori_schal_2008, title={New contact sex pheromone components of the german cockroach, Blattella germanica, predicted from the proposed biosynthetic pathway}, volume={34}, ISSN={["0098-0331"]}, DOI={10.1007/s10886-007-9409-8}, abstractNote={Upon contacting the cuticle of a sexually mature female, a male German cockroach exhibits a characteristic courtship behavior: he turns away from the female and raises his wings, thereby exposing tergal glands. The glandular secretion stimulates the female to mount the male and feed, thus positioning her appropriately for copulation. A multi-component contact sex pheromone produced by females is responsible for eliciting courtship behavior. The most abundant pheromone components are 3,11-dimethylnonacosan-2-one and 3,11-dimethylheptacosan-2-one, oxidation products of the abundant hydrocarbon analogs 3,11-dimethylnonacosane and 3,11-dimethylheptacosane, respectively. The C(29)-dimethyl ketone is thought to be further metabolized to two less abundant pheromone components, 29-hydroxy-3,11-dimethylnonacosan-2-one and 29-oxo-3,11-dimethylnonacosan-2-one. Based on this proposed biosynthetic pathway of pheromone production, we hypothesized that 3,11-dimethylheptacosan-2-one also would be oxidized to give two candidate pheromone components, 27-hydroxy-3,11-dimethylheptacosan-2-one, and 27-oxo-3,11-dimethylheptacosan-2-one. By using bioassay-guided fractionation and chemical analyses of cuticular extracts of virgin females and synthesis of the (3S,11S)-isomer of each of the two predicted pheromone components, we showed that the epicuticle of the German cockroach does indeed contain these two compounds. The contact sex pheromone of the female German cockroach, thus may consist of at least six biosynthetically related components.}, number={2}, journal={JOURNAL OF CHEMICAL ECOLOGY}, author={Eliyahu, Dorit and Nojima, Satoshi and Mori, Kenji and Schal, Coby}, year={2008}, month={Feb}, pages={229–237} }
 @article{eliyahu_mori_takikawa_leal_schal_2004, title={Behavioral activity of stereoisomers and a new component of the contact sex pheromone of female German cockroach, Blattella germanica}, volume={30}, ISSN={["1573-1561"]}, DOI={10.1023/B:JOEC.0000042405.05895.3a}, abstractNote={(3S,11S)-3,11-Dimethylnonacosan-2-one is a major component of the courtship stimulating, contact sex pheromone of the female German cockroach. Although the four synthetic stereoisomers of this compound have been tested in behavioral assays, their relative activity remains unresolved. Using isolated male antennae dosed with synthetic test compounds to assay male behavior, we found that at high doses all four stereoisomers elicited responses from 100% of the males. However, at physiologically relevant doses similar to those found on the female antenna, the (3S,11S)-isomer was the least effective of the four stereoisomers at eliciting courtship responses in males. This is the first example of a natural stereoisomer having less bioactivity than related stereoisomers that do not occur naturally. Another component of the sex pheromone blend, 3,11-dimethylheptacosan-2-one, was previously purified from the female's epicuticule and behaviorally assayed, but its activity was not confirmed through synthesis. We now confirm that synthetic (3S,11S)-3,11-dimethylheptacosan-2-one elicits behavioral responses, but less so than its C29 homolog.}, number={9}, journal={JOURNAL OF CHEMICAL ECOLOGY}, author={Eliyahu, D and Mori, K and Takikawa, H and Leal, WS and Schal, C}, year={2004}, month={Sep}, pages={1839–1848} }