Determination of diel periodicity of sex pheromone release in three species of Lepidoptera by ‘closed-loop-stripping’

Summary By means of closed-loop-stripping and subsequent GC analyses the diel periodicity of release of (Z)-11-hexadecenyl acetate, (E)-8-dodecenyl acetate, and (Z)-9-tetradecenyl acetate, the main constituents of the respective sex pheromone blends ofMamestra brassicae, Cryptophlebia leucotreta andSpodoptera sunia females, was determined.Pheromones, 64. For the 63rd contribution we have taken from: Szöcs, G., Toth, M., Bestmann, H. J., Vostrowsky, O., Heath, R. R., and Tumlinson, J. H., Z. Naturforsch.42c (1987) 165; Pheromones, 62: Bestmann et al.¹³.     

Sex pheromone conversion and degradation in antennae of the silkworm mothBombyx mori L.

Summary In living antennae of the silkworm mothBombyx mori L. the pheromone compound (E, Z)-10,12-hexadecadienol and hexadecanol are enzymatically converted to their corresponding fatty aldehydes, acids and long-chain fatty acid esters. The pheromone is completely degraded at high rates in the antennae of freshly hatched moths. The polar volatile [³H]metabolites exclusively consist of tritiated water. The half-life of the pheromone is about 2.5 min in males and 0.5 min in females. Drying inactivates the enzymes responsible for pheromone oxidation.Dedicated to Professor Adolf Butenandt on the occasion of his 85th birthday     

The male pheromone of the old house borerHylotrupes bajulus (L.) (Coleoptera: Cerambycidae): Identification and female response

We report here the identification of the long-range, male-produced sex pheromone of the Old house borerHylotrupes bajulus. Chemical analysis of hexane extracts obtained by surface extraction from dissected prothoracic glands and from headspace samples of the two sexes, revealed male-specific compounds: (3R)-3-hydroxy-2-hexanone, 2-hydroxy-3-hexanone, the diastereomeric diols (2R, 3R)-2,3-hexanediol and (2S, 3R)-2,3-hexanediol, 2,3-hexanedione, as well as 1-butanol.In wind tunnel bioassays we tested the influence of these male-specific compounds from the prothoracal glands on the behaviour of unmated and mated females. Specific behavioural sequences of the tested females (activity, running behaviour, searching, cleaning, flying, extension of ovipositor) were recorded. Unmated females were attracted by male beetles, headspace extracts of males, synthetic blends of the major pheromone compounds as well as by the components (3R)-3-hydroxy-2-hexanone, and the diastereomeric diols. Hexane, female beetles and 2,3-hexanedione did not attract unmated females. The reactions of mated females to male beetles and headspace samples did not differ significantly from those of the controls.The results of the bioassays show that the two-stage premating behaviour is initiated by emission of a long-range sex pheromone from the male prothoracal glands, which functions as an activator, attractant, and possibly aphrodisiac for unmated females.     

Pheromone components of the female elephant hawk-moth,Deilephila elpenor,and the silver-striped hawk-moth,Hippotion celerio

By means of gas chromatographic and mass spectroscopic methods, and combined GC-electroantennogram and electrosensillogram techniques, (E)-11-hexadecenal and (10E, 12E)-10,12-hexadecadienal [(E,E)-bombykal is also the main constituent of the pheromone of the silver-striped hawk-mothHippotion celerio. The biological activity of the substances was demonstrated with electroantennogram and single cell recording, and the physiological efficacy of the different hexadecadienal isomers compared.Pheromones, 79; as Pheromones, 78 is taken: Wu, Cai-Hong, and Bestmann, H. J., Chinese Science Bulletin34 (1989) 1475; pheromones, 77: Attygalle, A. B., Steghaus0Kovac, S., Ahmed, V. U., Maschwitz, U., Vostrowsky, Ol, and Bestmann, H. J., Naturwissen-schaften78 (1991) 90.     

Biosynthesis of a monoene and a conjugated diene sex pheromone component of the lightbrown apple moth by Δ11 desaturation

Summary Fatty acyl moieties present in the female sex pheromone gland of the lightbrown apple moth,Epiphyas postvittana, include the analogues of the two sex pheromone components, (E)-11-tetradecenyl acetate and (E,E)-9,11-tetradecadienyl acetate. Application of deuterium-labelled fatty acids followed by analysis by gas chromatographymass spectrometry showed that biosynthesis of the two pheromone components involved initial 11-desaturation of myristic and palmitic acids respectively.     

Sex pheromone of the pine sawflyDiprion pini (Hymenoptera: Diprionidae): Chemical identification,synthesis and biological activity

The main component of the sex pheromone secretion of femaleDiprion pini L. (Hymenoptera: Diprionidae) from insects collected both in Finland and in France has been identified as athreo-3,7-dimethyl-2-tridecanol (8 ng per female) stereoisomer by GC-MS and synthesis. The secretion also contains lower and higher homologues in small amounts (1–4% of the main component). Combined gas chromatographic-electroantennographic detection showed activity in both natural and esterified extracts (acetates and propionates); the esters of the main component gave the largest responses. The acetates and propionates of the eight stereoisomers of 3,7-dimethyl-2-tridecanol were synthesized from enantiomerically highly enriched (>99% ee) building blocks. The stereochemistry of the main component was established to be (2S,3R,7R)-3,7-dimethyl-2-tridecanol by GC analysis of the natural material. It was purified by liquid chromatography prior to the GC analysis of both its pentafluorobenzoates and its isopropylcarbamates on a non-chiral polar column (ECD) and a chiral column (NPD), respectively. Field tests demonstrated that both the acetate and propionate of the main component (100 g of each applied on cotton roll dispensers) were active in attracting males, with or without the presence of several of the minor compounds. Experiments with smaller amounts of the acetate and the propionate (1 g in France and 50 g in Finland) demonstrated that the propionate was more active than the acetate, and that it also caught more males than a blend of the two compounds.     

On the specific attraction of the males of the six-toothed spruce bark beetle,Pityogenes chalcographus (L.) to a mixture of synthetic pheromones of the eight-toothed spruce bark beetle,Ips typographus (L.) (Coleoptera,Scolytidae)

Summary Traps containing a mixture of attractants forIps typographus also caught other species of bark beetles. The numbers ofPityogenes chalcographus, Pityogenes conjunctus, andTrypodendron lineatum were too high to be interpreted as accidental captures. The males of the polygamousP. chalcographus were specifically attracted, indicating that theI. typographus pheromone or one of its components acts as a kairomone and primary attractant for the pioneering males ofP. chalcographus.     

Furan fatty acid steryl esters from the marine spongeDictyonella incisa which show inflammatory activity

Summary Three new furan fatty acids, (9Z, 19Z)-3, 6-epoxyhexacosa-3,5,19-tetraenoic acid (1a), (8Z, 11Z, 14Z, 17Z)-3, 6-epoxyeicosa-3,5,8,11,14,17-hexaenoic acid (2a), and (8Z, 11Z, 14Z, 17E)-3, 6-epoxyeicosa-3,5,8,11,14,17-hexaenoic acid (3a), and a new polyunsaturated fatty acid (5Z, 8Z, 11Z, 14Z, 17E)-eicosa-5,8,11,14,17-pentaenoic acid (6a), present in the spongeDictyonella incisa as the respective steryl esters, have been isolated as methyl esters and their structures have been determined by spectral and chemical analysis. The furan fatty acid esters have shown a high inflammatory activity, which suggests their potential role as feeding deterrents.     

The clerid beetle,Thanasimus formicarius,is attracted to the pheromone of the ambrosia beetle,Trypodendron lineatum

Summary Sticky traps containing (+)-lineatin, the pheromone of the ambrosia beetle,Trypodendron lineatum, attracted the predatorThanasimus formicarius to about the same extent as traps baited with ipslure, the pheromone blend used for mass-trappingIps typographus. The results indicate thatT. lineatum is an important prey forT. formicarius early in the season before the main prey becomes active. Addition ofexo-brevicomin to ipslure and ethanol and/or -pinene to (+)-lineatin did not significantly influence the catches of the predator.     

Chemical attraction of the eastern yellowjacket,Vespula maculifrons (Hymenoptera: Vespidae)

Summary Workers and queens of the eastern yellowjacket,Vespula maculifrons, are attracted to the artificial long-range attractant pheromone of the predaceous pentatomid,Podisus maculiventris. A 11 mixture of linalool or -terpineol and (E)-2-hexenal is as attractive toV. maculifrons workers as the pheromone.We thank A.S. Menke of the Systematic Entomology Laboratory, USDA, for identifying the yellowjackets. Mention of a company name does not imply endorsement by the US Department of Agriculture.     

Female sex pheromone of the longhorn beetleMigdolus fryanus Westwood: N-(2′S)-methylbutanoyl 2-methylbutylamine

The first known long-range female-released sex pheromone for the family Cerambycidae is reported fromMigdolus fryanus, a sugarcane pest in South America. Although two female-specific compounds, namely, N-(2S)-methylbutanoyl 2-methylbutylamine and N-formyll-isoleucine methyl esters were identified, field tests with synthetic chemicals revealed that only the amide was active and that the amino acid derivative neither increased or decreased trap catches by the amide. This is the first identification of amide as a sex pheromone.     

Recruitment communication and pheromone trails in the neotropical ants,Leptothorax (Nesomyrmex) spininodis andL. (N.) echinatinodis

Leptothorax (Nesomyrmex) spininodis andL. (N.) echinatinodis workers lay pheromone trails when returning from food sources to their nests. Workers from within the nest begin following the trail almost immediately upon the successful forager's return and do not require a leader. The trail remains effective for about four minutes under our laboratory conditions but it is unclear whether the trail alone is sufficient to induce recruitment or whether additional signals, perhaps emitted within the nest, are involved. Pheromone trails of this type have not previously been documented for leptothoracine ants.     

Age-dependent tolerance toBaculovirus in last larval instars of the codling moth,Cydia pomonella,L., induced either for pupation or for diapause

Summary LD₅₀ values as well as time-dependent parameters of granulosis virus infections were determined at different times during the last larval instar (L₅) of the codling moth,Cydia pomonella L., induced either for pupation or for diapause. A significant increase of tolerance to virus was found in 48-h-old L₅ induced for pupation, and 24 h later in L₅ induced for diapause.     

Accumulation of indole glucosinolates inPsylliodes chrysocephala L.-infested,or-damaged tissues of oilseed rape (Brassica napus L.)

Summary Infestation of oilseed rape (Brassica napus L.) by the cabbage stem flea beetle (Psylliodes chrysocephala L.) leads to an overall reduction in the levels of aliphatic (alkenyl- and hydroxyalkenyl-) glucosinolates in the damaged tissue (lamina, petiole, stem) and a massive accumulation of indole glucosinolates. Whilst artificial damage (puncturing), with and without associated bacterial infection with an isolate fromP. chrysocephala, led to such accumulation, this was less than that observed in the insect-infected situation.     

Sex determination in mammals — Before and after the evolution of SRY

Therian mammals (marsupials and placentals) have an XX female: XY male sex chromosome system, which is homologous to autosomes in other vertebrates. The testis-determining gene, SRY, is conserved on the Y throughout therians, but is absent in other vertebrates, suggesting that the mammal system evolved about 310 million years ago (MYA). However, recent work on the basal monotreme mammals has completely changed our conception of how and when this change occurred. Platypus and echidna lack SRY, and the therian X and Y are represented by autosomes, implying that SRY evolved in therians after their divergence from monotremes only 166 MYA. Clues to the ancestral mechanism usurped by SRY in therians are provided by the monotremes, whose sex chromosomes are homologous to the ZW of birds. This suggests that the therian X and Y, and the SRY gene, evolved from an ancient bird-like sex chromosome system which predates the divergence of mammals and reptiles 310 MYA. Received 4 March 2008; received after revision 22 April 2008; accepted 3 June 2008     

Hormonal control of pheromone responsiveness in the male black cutwormAgrotis ipsilon

In Lepidoptera, reproduction is linked to chemical communication between conspecific partners. When exposed to the female sex pheromone, males respond by exhibiting typical sexual behaviour which leads to mating. Here we show that presence of the juvenile hormone producing gland (corpora allata) of the male black cutworm,Agrotis ipsilon, is necessary for pheromone responsiveness. Allatectomized males do not show any sexual behaviour, although their antennal olfactory system is functional. Allatectomized males implanted with active corpora allata recover full pheromone receptivity. It is suggested that reproductive processes are synchronized in males and females through endocrine control; timing of the mating activity could serve as an adaptive strategy linked to the migratory behaviour of this species.     

Enhanced production of aggregation pheromones in four stored-product coleopterans feeding on methoprene-treated oats

Summary Production of aggregation pheromones by maleOryzaephilus surinamensis, O. mercator, Cryptolestes ferrugineus, andTribolium castaneum was enhanced by feeding on methoprene-treated oats, implicating juvenile hormone in control of pheromone production. Methoprene application to control insects in stored food products may cause enhanced pheromone production by these insects, thus drawing additional beetles into the treated product.Acknowledgments. We thank Dr. G. B. Staal of Zoëcon Corp. for a generous gift of methoprene. Particular thanks are due to J. Dodic for technical assistance. Research funded by the Natural Sciences and Engineering Research Council of Canada and the Science Council of British Columbia.     

A newTrichoplusia ni antennal receptor neuron that responds to attomolar concentrations of a minor pheromone component

Summary A newly discovered third class of sensillum trichodea on the antenna ofTrichoplusia ni contains an olfactory receptor neuron that responds to (Z)-9-tetradecen-1-ol acetate at 1×10^–18 M. The threshold of this neuron is 100–1000 times lower than the thresholds of two previously described pheromone-sensitive neurons that detect (Z)-7-dodecen-1-ol acetate and (Z)-7-tetradecen-1-ol acetate. The sensitivity and selectivity of this receptor neuron is evidence that (Z)-9-tetradecen-1-ol acetate may be important for sexual behavior.     

Oviposition-deterring pheromone inRhagoletis cerasi L.: Purification and determination of the chemical constitution

Summary An oviposition-deterring pheromone (ODP) of the European cherry fruit flyRhagoletis cerasi L. was isolated from faeces using cellulose and several reverse phase TLC and HPLC procedures. The biological activity was evaluated by means of behavior tests and by electrophysiological recordings from tarsal contact chemoreceptors. The compound was structurally characterized as a N[15(-glucopyranosyl)oxy-8-hydroxypalmitoyl]-taurine by spectroscopic means. The configurations of C-8 and C-15 of the fatty acid constituent remain to be established by synthetic work.     

Chemical analysis of the pheromone blends produced by males and females of the neotropical moth,Mocis megas (Guénée) (Lepidoptera,Noctuidae, Catocalinae)

Summary Pheromonal secretions produced by females and males of the noctuid moth,Mocis megas (Guénée) have been analyzed by gas chromatography and mass spectrometry (EI (electron impact) and CI (chemical ionization)). The female sex pheromone was a blend of (Z,Z,Z) 3,6,9 heneicosatriene (55%) and (Z,Z) 3,6-cis-9S, 10R-epoxyheneicosadiene (45%). Male secretion produced at the level of a prothoracic organ was a blend of two unsaturated major hydrocarbons: (Z,Z) 6,9 heneicosadiene, (64%) and (Z,Z,Z) 3,6,9 heneicosatriene (24%) and C₁₉, C₂₀ and C₂₂ homologues (total ratio 12%), as minor components. The trienic hydrocarbon was present in both sexes. The behavioral role of this male secretion has not yet been elucidated.