Sex Pheromone of the Scarab Beetle <Emphasis Type="Italic">Phyllophaga</Emphasis> (<Emphasis Type="Italic">Phytalus) georgiana</Emphasis> (Horn)

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. Sridhar Polavarapu, deceased May 7, 2004. We dedicate this publication to our friend and colleague.     

Comparison of Postprandial Oleic Acid, 9<Emphasis Type="Italic">c,</Emphasis>11<Emphasis Type="Italic">t</Emphasis> CLA and 10<Emphasis Type="Italic">t,</Emphasis>12<Emphasis Type="Italic">c</Emphasis> CLA Oxidation in Healthy Moderately Overweight Subjects

Few studies report the individual effect of 9c,11t- and 10t,12c-CLA on human energy metabolism. We compared the postprandial oxidative metabolism of 9c,11t- and 10t,12c-CLA and oleic acid (9c-18:1) in 22 healthy moderately overweight volunteers. After 24 weeks supplementation with 9c,11t-, 10t,12c-CLA or 9c-18:1 (3 g/day), subjects consumed a single oral bolus of the appropriate [1-¹³C]-labeled fatty acid. 8 h post-dose, cumulative oxidation was similar for 9c-18:1 and 10t,12c (P = 0.66), but significantly higher for 9c,11t (P < 0.01).     

Sexual Deception in the <Emphasis Type="Italic">Eucera</Emphasis>-Pollinated <Emphasis Type="Italic">Ophrys leochroma</Emphasis>: A Chemical Intermediate between Wasp- and <Emphasis Type="Italic">Andrena-</Emphasis>Pollinated Species

Ophrys flowers mimic sex pheromones of attractive females of their pollinators and attract males, which attempt to copulate with the flower and thereby pollinate it. Virgin females and orchid flowers are known to use the same chemical compounds in order to attract males. The composition of the sex pheromone and its floral analogue, however, vary between pollinator genera. Wasp-pollinated Ophrys species attract their pollinators by using polar hydroxy acids, whereas Andrena-pollinated species use a mixture of non-polar hydrocarbons. The phylogeny of Ophrys shows that its evolution was marked by episodes of rapid diversification coinciding with shifts to different pollinator groups: from wasps to Eucera and consequently to Andrena and other bees. To gain further insights, we studied pollinator attraction in O. leochroma in the context of intra- and inter-generic pollinator shifts, radiation, and diversification in the genus Ophrys. Our model species, O. leochroma, is pollinated by Eucera kullenbergi males and lies in the phylogeny between the wasp and Andrena-pollinated species; therefore, it is a remarkable point to understand pollinator shifts. We collected surface extracts of attractive E. kullenbergi females and labellum extracts of O. leochroma and analyzed them by using gas chromatography with electroantennographic detection (GC-EAD) and gas chromatography coupled with mass spectrometry (GC-MS). We also performed field bioassays. Our results show that O. leochroma mimics the sex pheromone of its pollinator’s female by using aldehydes, alcohols, fatty acids, and non-polar compounds (hydrocarbons). Therefore, in terms of the chemistry of pollinator attraction, Eucera-pollinated Ophrys species might represent an intermediate stage between wasp- and Andrena-pollinated orchid species.     

(1<Emphasis Type="Italic">S</Emphasis>,3<Emphasis Type="Italic">R</Emphasis>)-<Emphasis Type="Italic">cis</Emphasis>-Chrysanthemyl Tiglate: Sex Pheromone of the Striped Mealybug, <Emphasis Type="Italic">Ferrisia virgata</Emphasis>

Derivatives of 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylic acid (chrysanthemic acid) are classic natural pyrethroids discovered in pyrethrum plants and show insecticidal activity. Chrysanthemic acid, with two asymmetric carbons, has four possible stereoisomers, and most natural pyrethroids have the (1R,3R)-trans configuration. Interestingly, chrysanthemic acid–related structures are also found in insect sex pheromones; carboxylic esters of (1R,3R)-trans-(2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropyl)methanol (chrysanthemyl alcohol) have been reported from two mealybug species. In the present study, another ester of chrysanthemyl alcohol was discovered from the striped mealybug, Ferrisia virgata (Cockerell), as its pheromone. By means of gas chromatography–mass spectrometry, nuclear magnetic resonance spectrometry, and high-performance liquid chromatography analyses using a chiral stationary phase column and authentic standards, the pheromone was identified as (1S,3R)-(?)-cis-chrysanthemyl tiglate. The (1S,3R)-enantiomer strongly attracted adult males in a greenhouse trapping bioassay, whereas the other enantiomers showed only weak activity. The cis configuration of the chrysanthemic acid–related structure appears to be relatively scarce in nature, and this is the first example reported from arthropods.     

Role of (3<Emphasis Type="Italic">Z</Emphasis>,6<Emphasis Type="Italic">Z</Emphasis>,8<Emphasis Type="Italic">E</Emphasis>)-Dodecatrien-1-ol in Trail Following,Feeding, and Mating Behavior of <Emphasis Type="Italic">Reticulitermes hesperus</Emphasis>

Trail pheromones mediate communication among western subterranean termites, Reticulitermes hesperus Banks. Repetitive passages of ≥28 termites were required to establish a pheromone trail and trails needed to be reinforced because they lasted <48 hr. The minimal threshold concentration for inducing responses from termite workers and secondary reproductives was between 0.01 and 0.1 fg/cm of (3Z,6Z,8E)-dodecatrien-1-ol (henceforth, dodecatrienol). Workers showed optimal trail-following behavior to dodecatrienol at a concentration of 10 fg/cm. Trails with concentrations >10 pg/cm were repellent to workers. Workers did not detect pheromone gradients, responding equally to increasing or decreasing gradients of dodecatrienol, and termite workers were not able to differentiate between different concentrations of dodecatrienol. Termites preferred dodecatrienol trails to 2-phenoxyethanol trails. Antennae played a key role in trail pheromone perception. Dodecatrienol acted as an arrestant for worker termites (10 fg/cm²) and male alates (5 ng/cm²), whereas sternal gland extracts from females attracted male alates. Workers and alates, upon contact with filter paper disks treated with higher doses (10 fg/cm² and 5 ng/cm², respectively) of dodecatrienol, were highly excited (increased antennation and palpation) and repeatedly returned to the treated disks. Dodecatrienol did not act as a phagostimulant when offered on a paper towel disk. Reticulitermes hesperus is highly responsive to dodecatrienol, and it may play an important role in orientation of workers and alates.     

Yellow-Cedar, <Emphasis Type="Italic">Callitropsis</Emphasis> (<Emphasis Type="Italic">Chamaecyparis</Emphasis>) <Emphasis Type="Italic">nootkatensis</Emphasis>, Secondary Metabolites,Biological Activities,and Chemical Ecology

Yellow-cedar, Callitropsis nootkatensis, is prevalent in coastal forests of southeast Alaska, western Canada, and inland forests along the Cascades to northern California, USA. These trees have few microbial or animal pests, attributable in part to the distinct groups of biologically active secondary metabolites their tissues store for chemical defense. Here we summarize the new yellow-cedar compounds identified and their biological activities, plus new or expanded activities for tissues, extracts, essential oils and previously known compounds since the last review more than 40 years ago. Monoterpene hydrocarbons are the most abundant compounds in foliage, while heartwood contains substantial quantities of oxygenated monoterpenes and oxygenated sesquiterpenes, with one or more tropolones. Diterpenes occur in foliage and bark, whereas condensed tannins have been isolated from inner bark. Biological activities expressed by one or more compounds in these groups include fungicide, bactericide, sporicide, acaricide, insecticide, general cytotoxicity, antioxidant and human anticancer. The diversity of organisms impacted by whole tissues, essential oils, extracts, or individual compounds now encompasses ticks, fleas, termites, ants, mosquitoes, bacteria, a water mold, fungi and browsing animals. Nootkatone, is a heartwood component with sufficient activity against arthropods to warrant research focused toward potential development as a commercial repellent and biopesticide for ticks, mosquitoes and possibly other arthropods that vector human and animal pathogens.     

<Emphasis Type="Italic">Santalum </Emphasis><Emphasis Type="Italic">insulare</Emphasis> Acetylenic Fatty Acid Seed Oils: Comparison within the <Emphasis Type="Italic">Santalum</Emphasis> Genus

The sandalwood kernels of Santalum insulare (Santalaceae) collected in French Polynesia give seed oils containing significant amounts of ximenynic acid, E-11-octadecen-9-oic acid (64–86%). Fatty acid (FA) identifications were performed by gas chromatography/mass spectrometry (GC/MS) of FA methyl esters. Among the other main eight identified fatty acids, oleic acid was found at a 7–28% level. The content in stearolic acid, octadec-9-ynoic acid, was low (0.7–3.0%). An inverse relationship was demonstrated between ximenynic acid and oleic acid using 20 seed oils. Results obtained have been compared to other previously published data on species belonging to the Santalum genus, using multivariate statistical analysis. The relative FA S. insulare composition, rich in ximenynic acid is in the same order of those given for S. album or S. obtusifolium. The other compared species (S. acuminatum, S. lanceolatum, S. spicatum and S. murrayanum) are richer in oleic acid (40–59%) with some little differences in linolenic content.     

Sexual Isolation and Cuticular Hydrocarbon Differences between <Emphasis Type="Italic">Drosophila santomea</Emphasis> and <Emphasis Type="Italic">Drosophila yakuba</Emphasis>

Drosophila santomea and Drosophila yakuba are two sister species inhabiting Saõ Tomé island. Previous studies showed that both species display strong reproductive isolation, although they can produce a few viable hybrids. Our study tried to understand the mechanism of this ethological isolation between two allopatric strains. A strong sexual isolation was confirmed, with a marked asymmetry. Comparisons of latency times to either courtship or copulation suggest that males do not discriminate females, whereas D. yakuba females, but not D. santomea females, accept their homospecifics more quickly. Cuticular hydrocarbon compositions of both species and sexes were also established with gas chromatography (GC) and GC/mass spectrometry analysis. All have (Z)-7-tricosene as their major compound. There are several quantitative differences between species for few minor compounds. The largest difference concerns n-heneicosane, which is more abundant in D. santomea than in D. yakuba flies (up to seven times more between males). A similar quantitative difference was also found in a pair of sympatric strains. Furthermore, D. yakuba males artificially perfumed with n-heneicosane were discriminated negatively by D. yakuba females, suggesting a role for this compound in the sexual isolation between these two species.     

Oxidation kinetics for <Emphasis Type="Italic">cis</Emphasis>-9,<Emphasis Type="Italic">trans</Emphasis>-11 and <Emphasis Type="Italic">trans</Emphasis>-10,<Emphasis Type="Italic">cis</Emphasis>-12 isomers of CLA

The autoxidation processes of the cis-9,trans-11 (c9,t11) and trans-10,cis-12 (t10,c12) isomers of CLA were separately observed at ca. 0% RH and different temperatures. The t10,c12 CLA oxidized faster than the c9,t11 isomer at all tested temperatures. The first half of the oxidation process of t10,c12 CLA obeyed an autocatalytic-type rate expression, but the latter half followed first-order kinetics. On the other hand, the entire oxidation process of c9,t11 CLA could be expressed by the autocatalytic-type rate expression. The apparent activation energies and frequency factors for the autoxidation of the isomers were estimated from the rate constants obtained at various temperatures based on the Arrhenius equation. The apparent activation energies for the CLA isomers were greater than those for the nonconjugated n−6 and n−3 PUFA or their esters. However, the enthalpyentropy compensation held during the autoxidation of both the CLA and PUFA. This suggested that the autoxidation mechanisms for the CLA and PUFA were essentially the same.     

Attraction of Coffee Bean Weevil, <Emphasis Type="Italic">Araecerus fasciculatus</Emphasis>, to Volatiles from the Industrial Yeast <Emphasis Type="Italic">Kluyveromyces lactis</Emphasis>

The coffee bean weevil (CBW), Araecerus fasciculatus (De Geer, 1775) (Coleoptera: Anthribidae) is an important pest of stored products such as grains, coffee beans, cassava, and traditional Chinese medicine materials. In China, CBW causes large losses of Daqu, a traditional Chinese liquor fermentation starter, and, unfortunately, the use of conventional insecticides against CBW is not suitable in Daqu storage. We found CBW to be highly attracted to fermenting yeast cultures, such as Kluyveromyces lactis. Eight volatile compounds, produced by fermenting cultures and not by sterile samples, were identified by gas chromatography coupled with mass spectrometry. Five of these substances elicited significant responses in Y-tube behavioral bioassays. Field trapping experiments revealed 2-phenylethanol and 2-phenylethyl acetate to be crucial for attraction of CBW. Results show that yeast volatiles play an important role in host location, and that 2-phenylethanol and 2-phenylethyl acetate could be utilized as potential attractants in monitoring and control systems against this important pest.     

Inhibitory Effects of Semiochemicals on the Attraction of an Ambrosia Beetle <Emphasis Type="Italic">Euwallacea</Emphasis> nr. <Emphasis Type="Italic">fornicatus</Emphasis> to Quercivorol

The Euwallacea fornicatus (Eichhoff) species complex includes the polyphagous shot hole borer (PSHB), an ambrosia beetle infesting avocado limbs, Persea americana Mill. Synthetic quercivorol, a monoterpene alcohol, is known to attract females (males are flightless) over a range of release rates spanning three orders of magnitude. The upper release dose was extended 10-fold using sticky traps baited with quercivorol released at 1× (0.126 mg/day), 10×, and 108× relative rates to obtain a dose?response curve fitting a kinetic formation function. Naturally infested limbs of living avocado trees were wrapped with netting to exclude the possibility of catching emerging beetles on the encircling sticky traps. The results indicate PSHB are significantly attracted to infested limbs. Ethanol released over a 64-fold range (lowest rate of 7.5 mg/day) was moderately inhibitory of PSHB attraction to 1× quercivorol. β-caryophyllene and eucalyptol did not appear to affect attraction at the rates tested. A field test of potential inhibitors of 1× quercivorol was done using ~1 mg/day releases of monoterpene ketones: (?)-(S)-verbenone, (+)-(R)-verbenone, 3-methyl-2-cyclo-hexen-1-one (MCH or seudenone), piperitone, (+)-(S)-carvone, and racemic cryptone. Only piperitone and the two enantiomers of verbenone were strongly inhibitory. A blend of piperitone and verbenone tested together at different distances (0, 0.5, 1, 2, and 4 m) from a 1× quercivorol baited sticky trap became increasingly ineffective in inhibiting the attractant as separation distance increased. Due to the relatively short-range repellency (<1 m), the inhibitors would need to be released from several places on each tree to effectively repel PSHB from avocado trees. Effective attraction radii, EAR, and circular EARc are estimated for the quercivorol baits released at 1×, 10× and 108× rates. Push-pull simulations of moving beetles were performed in 1 ha plots with 2, 4, or 16 traps of 10× EARc and 400 trees (0, 1, or 3 inhibitors per tree) of which ten had an infested limb (EARc?=?0.5 m). The simulations indicate that push-pull methods would be more effective in reducing PSHB mating than simply using mass-trapping alone.     

Pheromone-based Arrestment Behavior in the Common Silverfish, <Emphasis Type="Italic">Lepisma saccharina</Emphasis>, and Giant Silverfish, <Emphasis Type="Italic">Ctenolepisma longicaudata</Emphasis>

Aggregations of the common silverfish, Lepisma saccharina, and giant silverfish, Ctenolepisma longicaudata (both Thysanura: Lepismatidae), are mediated by species-specific pheromones. In dual-choice, still-air olfactometer experiments, filter paper previously exposed to 12 male, female, or juvenile L. saccharina or C. longicaudata arrested conspecifics regardless of developmental stage or sex. Arrestment responses required physical contact with the pheromone. Insect-derived frass, scales, antennae, and setae, as well as salivary gland content, are not the source of the contact pheromone in L. saccharina. Lepisma saccharina did not respond to the pheromone of C. longicaudata, nor to that of another thysanuran, the firebrat Thermobia domestica. However, C. longicaudata responded to pheromones of both L. saccharina and T. domestica, whereas T. domestica responded to the C. longicaudata but not L. saccharina pheromone. These results support the hypothesis that a closer phylogenetic relationship exists between C. longicaudata and T. domestica than between C. longicaudata and L. saccharina, but a definitive conclusion must await molecular genetic analyses of all three species.     

Effect of <Emphasis Type="Italic">trans</Emphasis>8, <Emphasis Type="Italic">cis</Emphasis>10+<Emphasis Type="Italic">cis</Emphasis>9, <Emphasis Type="Italic">trans</Emphasis>11 Conjugated Linoleic Acid Mixture on Lipid Metabolism in 3T3-L1 Cells

Evidence suggests that minor isomers of conjugated linoleic acid (CLA), such as trans8, cis10 CLA, can elicit unique biological effects of their own. In order to determine the effect of a mixture of t8, c10+c9, t11 CLA isomers on selected aspects of lipid metabolism, 3T3-L1 preadipocytes were differentiated for 8 days in the presence of 100 μM linoleic acid (LA); t8, c10+c9, t11 CLA; t10, c12+c9, t11 CLA or purified c9, t11 CLA. Whereas supplementation with c9, t11 and t10, c12+c9, t11 CLA resulted in cellular triglyceride (TG) concentrations of 3.4 ± 0.26 and 1.3 ± 0.11 μg TG/μg protein, respectively (P < 0.05), TG accumulation following treatment with CLA mixture t8, c10+c9, t11 was significantly intermediate (2.5 ± 0.22 μg TG/μg protein, P < 0.05) between the two other CLA treatments. However, these effects were not attributable to an alteration of the Δ⁹ desaturation index. Adiponectin content of adipocytes treated with t8, c10+c9, t11 mixture was similar to the individual isomer c9, t11 CLA, and both the t8, c10+c9, t11 and c9, t11 CLA groups were greater (P < 0.05) than in the t10, c12+c9, t11 CLA group. Overall, these results suggest that t8, c10+c9, t11 CLA mixture affects TG accumulation in 3T3-L1 cells differently from the c9, t11 and t10, c12 isomers. Furthermore, the reductions in TG accumulation occur without adversely affecting the adiponectin content of these cells.     

Altered Lipid Response in Hamsters Fed <Emphasis Type="Italic">cis</Emphasis>-9,<Emphasis Type="Italic">trans</Emphasis>-11+<Emphasis Type="Italic">trans</Emphasis>-8,<Emphasis Type="Italic">cis</Emphasis>-10 Conjugated Linoleic Acid Mixture

The objective of the present study was to compare the effects of cis-9,trans-11 + trans-8,cis-10 conjugated linoleic acid (CLA) mixture to those of cis-9,trans-11 + trans-10,cis-12 CLA mixture and linoleic acid (LA) on lipoprotein profile, hepatic lipids, body composition and digestibility of dietary fat in hamsters (n = 17) fed diets containing 2% of experimental fat (w/w) for 28 days. The cis-9,trans-11 + trans-10,cis-12 CLA mixture showed higher LDL cholesterol concentrations than LA and the cis-9,trans-11 + trans-8,cis-10 CLA mixture. The cis-9,trans-11 + trans-8,cis-10 CLA mixture induced similar plasma LDL cholesterol and hepatic lipid concentrations, and coefficient of digestibility as LA, indicating no effect of the trans-8,cis-10 CLA isomer on these lipid parameters. On the other hand, the cis-9,trans-11 + trans-8,cis-10 CLA mixture induced higher plasma VLDL cholesterol and triglycerides than LA and the cis-9,trans-11 + trans-10,cis-12 CLA mixture. The cis-9,trans-11 + trans-8,cis-10 CLA mixture also induced the highest plasma glucose concentrations compared with the two other groups, indicating an impairment of glycemic control. No differences in body composition were noted between the three groups. The present results thus show that the cis-9,trans-11 + trans-8,cis-10 CLA mixture can deteriorate plasma VLDL cholesterol and triglycerides in hamsters, possibly due to an increased flux of glucose.     

Biosynthesis of (3<Emphasis Type="Italic">Z</Emphasis>,6<Emphasis Type="Italic">Z</Emphasis>,9<Emphasis Type="Italic">Z</Emphasis>)-3,6,9-Octadecatriene: The Main Component of the Pheromone Blend of <Emphasis Type="Italic">Erannis bajaria</Emphasis>

The hydrocarbons (3Z,6Z,9Z)-3,6,9-octadecatriene (3Z,6Z,9Z-18:H) and (3Z,6Z,9Z)-3,6,9-nonadecatriene (3Z,6Z,9Z-19:H) constitute the pheromone of the winter moth, Erannis bajaria. These compounds belong to a large group of lepidopteran pheromones which consist of unsaturated hydrocarbons and their corresponding oxygenated derivatives. The biosynthesis of such hydrocarbons with an odd number of carbons in the chain is well understood. In contrast, knowledge about the biosynthesis of even numbered derivatives is lacking. We investigated the biosynthesis of 3Z,6Z,9Z-18:H by applying deuterium-labeled precursors to females of E. bajaria followed by gas chromatography–mass spectrometry analysis of extracts of the pheromone gland. A mixture of deuterium-labeled [17,17,18,18-²H₄]-3Z,6Z,9Z-18:H and the unlabeled 3Z,6Z,9Z-18:H was obtained after topical application and injection of (10Z,13Z,16Z)-[2,2,3,3-²H₄]-10,13,16-nonadecatrienoic acid ([2,2,3,3-²H₄]-10Z,13Z,16Z-19:acid) or (11Z,14Z,17Z)-[3,3,4,4-²H₄]-11,14,17-icosatrienoic acid ([3,3,4,4-²H₄]-11Z,14Z,17Z-20:acid). These results are consistent with a biosynthetic pathway that starts with α-linolenic acid (9Z,12Z,15Z-18:acid). Chain elongation leads to 11Z,14Z,17Z-20:acid, which is shortened by α-oxidation as the key step to yield 10Z,13Z,16Z-19:acid. This acid can be finally reduced to an aldehyde and decarbonylated or decarboxylated to furnish the pheromone component 3Z,6Z,9Z-18:H. A similar transformation of 11Z,14Z,17Z-20:acid yields the second pheromone component, 3Z,6Z,9Z-19:H.     

<Emphasis Type="Italic">cis</Emphasis>-Vaccenyl Acetate,A Female-Produced Sex Pheromone Component of <Emphasis Type="Italic">Ortholeptura valida</Emphasis>, A Longhorned Beetle in the Subfamily Lepturinae

We report the identification, synthesis, and field bioassays of a female-produced sex attractant pheromone component of the cerambycid beetle Ortholeptura valida (LeConte). Headspace volatiles from females contained a female-specific compound, (Z)-11-octadecen-1-yl acetate, which elicited a strong response from antennae of adult males in coupled gas chromatography-electroantennogram analyses. In field bioassays, significant numbers of males were collected by traps baited with this compound. The pheromone represents a new structural class of cerambycid pheromones, and is the first pheromone identified for a cerambycid species in the subfamily Lepturinae.     

Synthesis of <Emphasis Type="Italic">p</Emphasis><Emphasis Type="Bold">-</Emphasis> and <Emphasis Type="Italic">n</Emphasis>-type Gels Doped with Ionic Charge Carriers

In this study, we synthesized the new kinds of semiconducting polymeric gels having negative (n-type) and positive (p-type) counter ions as charge carriers. The polyacrylamide gel was doped with pyranine (8-hydroxypyrene-1,3,6-trisulfonic acid, trisodium salt), having \textSO₃ ^- {\text{SO}}_{3}^{ - } ions as side groups and Na⁺ as counter ions, so-called p-type semiconducting gel. The doping process was performed during the polymerization where the pyranine binds to the polymer strands over OH group chemically via radical addition. In a similar way, N-isopropylacrylamide (NIPA) gel was doped with methacrylamidopropyltrimethyl ammonium chloride (MAPTAC), having Cl⁻ as counter ions, so-called n-type semiconducting gel. Here MAPTAC was embedded by copolymerization within the polymer network (NIPA). These semiconducting gels can show different electrical properties by changing the concentration of the doping agents, swelling ratio etc. We have shown that the pn junction, formed by combining p-type and n-type gels together in close contact, rectifies the current similar to the conventional Si and Ge diodes.     

Specificity in Chemical Profiles of Workers,Brood and Mutualistic Fungi in <Emphasis Type="Italic">Atta</Emphasis>, <Emphasis Type="Italic">Acromyrmex,</Emphasis> and <Emphasis Type="Italic">Sericomyrmex</Emphasis> Fungus-growing Ants

Neotropical attine ants live in obligatory symbiosis with a fungus that they grow for food on a substrate of primarily plant material harvested by workers. Nestmate recognition is likely based on chemical cues as in most other social insects, but recent studies have indicated that both the ants and their mutualistic fungi may contribute to the recognition templates. To investigate the within-colony variation in chemical profiles, we extracted and identified compounds from the cuticle of workers, the postpharyngeal gland of workers, ant pupae and larvae, and the fungal symbiont of three species of higher attine ants: Atta colombica, Acromyrmex echinatior, and Sericomyrmex amabilis. The relative proportions of identified compounds were compared and represented 11 classes: n-alkanes, alkenes, branched methylalkanes, branched dimethylalkanes, trimethylalkanes, branched alkenes, aldehydes, alcohols, acetates, acids, and esters. The chemical profiles in all three species are likely to be sufficiently different to allow discrimination at the species and colony level and sufficiently similar within colonies to generate a relatively constant colony-specific chemical gestalt. The relative likelihood of individual compounds being derived from the ants, the ant brood, or the fungal symbiont are discussed. We hypothesize that hydrocarbons are particularly important as recognition cues because they appear to simultaneously allow the assessment of developmental stages and the identification of symbiont, colony, and species.     

Sex Pheromone of the Rare Click Beetle <Emphasis Type="Italic">Betarmon bisbimaculatus</Emphasis>

The click beetle Betarmon bisbimaculatus (Fabricius, 1803) (Coleoptera: Elateridae) has a scattered distribution throughout a large area in Europe and the near East. Due to its scarcity, little is known about the ecology, biology, and development of this peculiar species. Here, we studied the composition of the female-released sex pheromone of B. bisbimaculatus. Neryl hexanoate, neryl octanoate, and neryl decanoate, in a ratio of approximately 3:1:6, were the only volatile compounds present in the extracts of pheromone glands. A synthetic mixture of all three compounds in the natural ratio was highly attractive to males in field traps. When the compounds were tested individually, only traps baited with neryl hexanoate were attractive, but they caught only a sixth of the males compared to the mixture. Based on the similarity of their sex pheromones, we propose that the tribe Pomachiliini with B. bisbimaculatus is closely related to the tribe Agriotini. This study shows the potential of sex pheromone studies for monitoring of rare and threatened insects as well as for elucidating phylogenetic relationships.     

Male-Produced Aggregation Pheromone of the Cerambycid Beetle <Emphasis Type="Italic">Rosalia funebris</Emphasis>

We report the identification, synthesis, and field bioassays of a volatile, male-produced aggregation pheromone of a long-horned beetle, the banded alder borer, Rosalia funebris Mots. Headspace collections from males contained a major male-specific compound, (Z)-3-decenyl (E)-2-hexenoate, and several minor components, identified as (Z)-3-decenol, (Z)-3-nonenyl (E)-2-hexenoate, and (Z)-3-decenyl (E)-3-hexenoate. The antennae of both males and females responded strongly to (Z)-3-decenyl (E)-2-hexenoate. We collected significant numbers of adult R. funebris in field bioassays using traps baited with this compound. This pheromone structure is unprecedented in the literature of cerambycid pheromones and distinct from the more common diol/hydroxyketone pheromone motif of many other species of the diverse subfamily Cerambycinae. This is the first pheromone identified for a species in the tribe Rosaliini. Electronic supplementary material  The online version of this article (doi:) contains supplementary material, which is available to authorized users.