@article{nojima_classen_groot_schal_2018, title={Qualitative and quantitative analysis of chemicals emitted from the pheromone gland of individual Heliothis subflexa females}, volume={13}, ISSN={1932-6203}, url={http://dx.doi.org/10.1371/journal.pone.0202035}, DOI={10.1371/journal.pone.0202035}, abstractNote={The chemicals emitted from the sex pheromone gland of individual Heliothis subflexa females were sampled using a short section of thick-film megabore fused silica capillary column, and the pheromone glands of the same females were extracted after the effluvia collection. Both samples were treated with a silylation reagent, and then subjected to gas chromatography-chemical ionization-mass spectrometry for quantitative and qualitative analysis of all components. The total amount of all 11 components emitted from the glands of calling females was 153 ng/female/hr, which was substantially higher than previously reported. The ratios of the pheromone components in the volatile emissions and pheromone gland extracts were generally similar to previous studies, but with notable differences. The collections of volatiles and gland extractions contained, respectively: Z9-14:Ald (1.57%, 1.35%), 14:Ald (3.78%, 1.51%), Z7 + Z9-16:Ald (9.60%, 3.59%), Z11-16:Ald (76.14%, 18.94%), 16:Ald (2.95%, 2.17%), Z9-16:OH (0.07%, 7.21%), Z11-16:OH (1.11%, 49.04%), Z7-16:OAc (0.48%, 1.73%), Z9-16:OAc (1.32%, 4.02%), and Z11-16:OAc (2.98%, 10.43%). The thick-film megabore column is an efficient approach for sampling the headspace for semiochemicals.}, number={8}, journal={PLOS ONE}, publisher={Public Library of Science (PLoS)}, author={Nojima, Satoshi and Classen, Alice and Groot, Astrid T. and Schal, Coby}, editor={Hull, J JoeEditor}, year={2018}, month={Aug}, pages={e0202035} }
 @article{nojima_kiemle_webster_apperson_schal_2011, title={Nanogram-Scale Preparation and NMR Analysis for Mass-Limited Small Volatile Compounds}, volume={6}, ISSN={1932-6203}, url={http://dx.doi.org/10.1371/journal.pone.0018178}, DOI={10.1371/journal.pone.0018178}, abstractNote={Semiochemicals are often produced in infinitesimally small quantities, so their isolation requires large amounts of starting material, not only requiring significant effort in sample preparation, but also resulting in a complex mixture of compounds from which the bioactive compound needs to be purified and identified. Often, compounds cannot be unambiguously identified by their mass spectra alone, and NMR analysis is required for absolute chemical identification, further exacerbating the situation because NMR is relatively insensitive and requires large amounts of pure analyte, generally more than several micrograms. We developed an integrated approach for purification and NMR analysis of <1 µg of material. Collections from high performance preparative gas-chromatography are directly eluted with minimal NMR solvent into capillary NMR tubes. With this technique, 1H-NMR spectra were obtained on 50 ng of geranyl acetate, which served as a model compound, and reasonable H-H COSY NMR spectra were obtained from 250 ng of geranyl acetate. This simple off-line integration of preparative GC and NMR will facilitate the purification and chemical identification of novel volatile compounds, such as insect pheromones and other semiochemicals, which occur in minute (sub-nanogram), and often limited, quantities.}, number={3}, journal={PLoS ONE}, publisher={Public Library of Science (PLoS)}, author={Nojima, Satoshi and Kiemle, David J. and Webster, Francis X. and Apperson, Charles S. and Schal, Coby}, editor={Leal, WalterEditor}, year={2011}, month={Mar}, pages={e18178} }
 @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{robbins_nojima_polavarapu_koppenhoefer_rodriguez-saona_holdcraft_consolie_peck_roelofs_2009, title={Sex Pheromone of the Scarab Beetle Phyllophaga (Phytalus) georgiana (Horn)}, volume={35}, ISSN={["1573-1561"]}, DOI={10.1007/s10886-009-9593-9}, abstractNote={The sex pheromone of Phyllophaga (Phytalus) georgiana was characterized as valine methyl ester, tentatively the l-enantiomer. This is the first sex pheromone identified from the Phyllophaga subgenus Phytalus. The pheromone was extracted from female glands, the active component isolated by coupled gas chromatography–electroantennogram detection analysis, characterized by mass spectrometry, and shown to be active in field tests. The seasonal flight pattern was determined for P. georgiana as well as for three other species, P. anxia (both northern and southern genitalic forms), P. gracilis, and P. postrema. The latter three species were captured in traps baited with l-isoleucine methyl ester.}, number={3}, journal={JOURNAL OF CHEMICAL ECOLOGY}, author={Robbins, Paul S. and Nojima, Satoshi and Polavarapu, Sridhar and Koppenhoefer, Albrecht M. and Rodriguez-Saona, Cesar and Holdcraft, Robert J. and Consolie, Nancy H. and Peck, Daniel C. and Roelofs, Wendell L.}, year={2009}, month={Mar}, pages={336–341} }
 @article{nojima_apperson_schal_2008, title={A simple, convenient, and efficient preparative GC system that uses a short megabore capillary column as a trap}, volume={34}, ISSN={["0098-0331"]}, DOI={10.1007/s10886-008-9437-z}, abstractNote={A simple, convenient, and highly efficient preparative GC system has been developed that uses short sections of megabore capillary columns as sample collection (sorbent) traps. The performance of this system with various types of capillary column traps and under various collection conditions was systematically investigated with model compounds, including C4 to C20 normal alkanes, esters, and alcohols. The thickness and polarity of the sorptive stationary phase and the temperature of the collection trap affected trap performance. Each group of compounds was efficiently trapped above a critical Kovat's index, and the type of trap (deactivated, methyl polysiloxane, polyethylene glycol), film thickness, and whether or not the trap was cooled significantly shifted this threshold index. Above this critical index, recovery efficiencies of traps with methyl polysiloxane films were 80-100% for a wide range of injected sample mass. For example, a DB-1 collection trap with a film thickness of 1.5 microm methyl polysiloxane operated at ambient temperature trapped >84% of the mass of injected compounds of all three chemical classes with Kovat's index >1,100 (determined on a nonpolar column) with injected sample mass ranging from 10 to 1,000 ng of each compound. This preparative GC system is technically and economically feasible for most researchers. Furthermore, it is suitable for the preparation of NMR samples of volatile and semivolatile compounds, especially with sample sizes ranging from several nanograms to several micrograms.}, number={3}, journal={JOURNAL OF CHEMICAL ECOLOGY}, author={Nojima, Satoshi and Apperson, Charles S. and Schal, Coby}, year={2008}, month={Mar}, pages={418–428} }
 @article{shimomura_nojima_yajima_ohsawa_2008, title={Homofarnesals: Female sex attractant pheromone components of the southern cowpea weevil, Callosobruchus chinensis}, volume={34}, ISSN={["1573-1561"]}, DOI={10.1007/s10886-008-9451-1}, abstractNote={The southern cowpea weevil, Callosobruchus chinensis (Coleoptera: Bruchidae), is a major pest of stored legumes in warm temperate and tropical climates. The female sex attractant pheromone was extracted from filter-paper shelters taken from containers that housed virgin females. The extracts were purified by various chromatographic techniques, and the biologically active components in the fractions were screened by gas chromatographic-electroantennographic detection analysis with male antennae. Two compounds that elicited electrophysiological responses were isolated, and gas chromatography-mass spectrometry, nuclear magnetic resonance, and micro-chemical analyses suggested that the active compounds were homofarnesals, (2Z,6E)- and (2E,6E)-7-ethyl-3,11-dimethyl-2,6,10-dodecatrienals. Males of C. chinensis were significantly attracted to filter paper discs loaded with the synthetic compounds at 0.01-0.1 ng compared to solvent control in a Y-tube olfactometer assay. These pheromone components represent unique chemical structures within the genus Callosobruchus.}, number={4}, journal={JOURNAL OF CHEMICAL ECOLOGY}, author={Shimomura, Kenji and Nojima, Satoshi and Yajima, Shunsuke and Ohsawa, Kanju}, year={2008}, month={Apr}, pages={467–477} }
 @article{ponnusamy_xu_nojima_wesson_schal_apperson_2008, title={Identification of bacteria and bacteria-associated chemical cues that mediate oviposition site preferences by Aedes aegypti}, volume={105}, ISSN={0027-8424 1091-6490}, url={http://dx.doi.org/10.1073/pnas.0802505105}, DOI={10.1073/pnas.0802505105}, abstractNote={The yellow fever mosquito,Aedes aegypti, the global vector of dengue and yellow fever, is inexorably linked to water-filled human-made containers for egg laying and production of progeny. Oviposition is stimulated by cues from water containers, but the nature and origin of these cues have not been elucidated. We showed that mosquito females directed most of their eggs to bamboo and white-oak leaf infusions, and only a small fraction of the eggs were laid in plain water containers. In binary choice assays, we demonstrated that microorganisms in leaf infusions produced oviposition-stimulating kairomones, and using a combination of bacterial culturing approaches, bioassay-guided fractionation of bacterial extracts, and chemical analyses, we now demonstrate that specific bacteria-associated carboxylic acids and methyl esters serve as potent oviposition stimulants for gravidAe. aegypti. Elucidation of these compounds will improve understanding of the chemical basis of egg laying behavior ofAe. aegypti, and the kairomones will likely enhance the efficacy of surveillance and control programs for this disease vector of substantial global public health importance.}, number={27}, journal={Proceedings of the National Academy of Sciences}, publisher={Proceedings of the National Academy of Sciences}, author={Ponnusamy, L. and Xu, N. and Nojima, S. and Wesson, D. M. and Schal, C. and Apperson, C. S.}, year={2008}, month={Jul}, pages={9262–9267} }
 @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{youngsteadt_nojima_haberlein_schulz_schal_2008, title={Seed odor mediates an obligate ant-plant mutualism in Amazonian rainforests}, volume={105}, ISSN={0027-8424 1091-6490}, url={http://dx.doi.org/10.1073/pnas.0708643105}, DOI={10.1073/pnas.0708643105}, abstractNote={
            Seed dispersal mutualisms are essential for the survival of diverse plant species and communities worldwide. Among invertebrates, only ants have a major role in seed dispersal, and thousands of plant species produce seeds specialized for ant dispersal in “diffuse” multispecies interactions. An outstanding but poorly understood ant–seed mutualism occurs in the Amazonian rainforest, where arboreal ants collect seeds of several epiphyte species and cultivate them in nutrient-rich nests, forming abundant and conspicuous hanging gardens known as ant-gardens (AGs). AG ants and plants are dominant members of lowland Amazonian ecosystems, and their interaction is both specific and obligate, but the means by which ants locate, recognize, and accept their mutualist seeds while rejecting other seeds is unknown. Here we address the chemical and behavioral basis of the AG interaction. We show that workers of the AG ant
            Camponotus femoratus
            are attracted to odorants emanating from seeds of the AG plant
            Peperomia macrostachya
            , and that chemical cues also elicit seed-carrying behavior. We identify five compounds from
            P. macrostachya
            seeds that, as a blend, attract
            C. femoratus
            workers. This report of attractive odorants from ant-dispersed seeds illustrates the intimacy and complexity of the AG mutualism and begins to illuminate the chemical basis of this important and enigmatic interaction.
          }, number={12}, journal={Proceedings of the National Academy of Sciences}, publisher={Proceedings of the National Academy of Sciences}, author={Youngsteadt, E. and Nojima, S. and Haberlein, C. and Schulz, S. and Schal, C.}, year={2008}, month={Jan}, pages={4571–4575} }
 @article{nojima_shimomura_honda_yamamoto_ohsawa_2007, title={Contact sex pheromone components of the cowpea weevil, Callosobruchus maculatus}, volume={33}, ISSN={["1573-1561"]}, DOI={10.1007/s10886-007-9266-5}, abstractNote={The cowpea weevil, Callosobruchus maculatus, is a major pest of stored pulses. Females of this species produce a contact sex pheromone that elicits copulation behavior in males. Pheromone was extracted from filter-paper shelters taken from cages that housed females. Crude ether extract stimulated copulation in male C. maculatus. Initial fractionation showed behavioral activity in acidic and neutral fractions. Furthermore, bioassay-guided fractionation and gas chromatography-mass spectroscopy (GC-MS) analysis of active fractions revealed that the active components of the acidic fraction were 2,6-dimethyloctane-1,8-dioic acid and nonanedioic acid. These components along with the hydrocarbon fraction, a mixture of C(27)-C(35) straight chain and methyl branched hydrocarbons, had a synergistic effect on the behavior of males. Glass dummies treated with an authentic pheromone blend induced copulation behavior in males. The potential roles of the contact sex pheromone of C. maculatus are discussed.}, number={5}, journal={JOURNAL OF CHEMICAL ECOLOGY}, author={Nojima, Satoshi and Shimomura, Kenji and Honda, Hiroshi and Yamamoto, Izuru and Ohsawa, Kanju}, year={2007}, month={May}, pages={923–933} }
 @article{nojima_2005, title={Identification of the female sex pheromone of the German cockroach, Blattela germanica}, volume={6}, ISBN={1345-4722}, number={3}, journal={Aroma Research}, author={Nojima, S.}, year={2005}, pages={237} }