Identification of a testosterone-dependent unique volatile constituent of male mouse urine: 7-exo-ethyl-5-methyl-6,8-dioxabicyclo[3.2.1]-3-octene

Investigations regarding the chemical composition of the volatiles in male mouse urine have recently enabled the structural elucidation of a hitherto unreported urinary component, 7-exo-ethyl-5-methyl-6,8-dioxabicyclo[3.2.1]-3-octene. This compound's uniqueness to mouse urine and its dependence on testosterone levels in the male suggest its probable role as a mouse pheromone or pheromone adjuvant.     

Pheromone binding proteins of the mouse,Mus musculus

Proteins of the Major Urinary Complex of the adult male mouse (Mus musculus) selectively bind the male pheromones 2-(sec-butyl)thiazoline and dehydro-exo-brevicomin, and concentrate them in urine.     

2-Phenylethanol,a presumed sexual stimulant produced by the male cabbage looper moth,Trichoplusia ni

Summary A sex pheromone produced by male cabbage looper moths,Trichoplusia ni (Hübner), has been isolated from the genital scent brushes and identified as 2-phenylethanol. It is shown conclusively to elicit specific behavioural responses in the female (such as wing vibration and abdominal elevation), as determined by a novel behavioural laboratory bioassay. This is taken as further evidence that the male pheromone ofT. ni acts as a sexual stimulant (aphrodisiac) prior to mating. 2-Phenylethanol represents the first identification of a genital scent brush pheromone in the family Noctuidae, and of a male pheromone in the subfamily Plusiinae.Mention of a proprietary product in this paper does not constitute a recommendation or an endorsement of the product by the U. S. Department of Agriculture.     

Occurrence of a pheromone-producing gland in female tobacco beetles

Summary A pheromone-producing gland was discovered in the second abdominal segment of virgin female tobacco beetles,Lasioderma serricorne (Fabricius). The gland duct extends to an orifice below the genital pore and is supported by a rigid invagination of the integument. Hexane extracts of intact pheromone glands were found attractive to male tobacco beetles and also induced high receptor potentials in the olfactory sensilla of the antennae of maleL. serricorne. A surface extract of virgin females proved to be significantly more attractive than an extract of pheromone glands.     

Étude cytologique d'une translocation chromosomeY-autosome chez la souris

Summary A male mouse with one translocation involving theY-chromosome has been observed in the F1 offspring of a male mouse given 300 R of X-irradiation. 6 types of spermatocytes were recorded. Our observations appear to confirm that the acrocentricX of the mouse associates end-to-end with theY at its centromeric end.     

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.     

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.     

Enhancement of boll weevilAnthonomus grandis Boh. (Coleoptera: Curculionidae) pheromone biosynthesis with JH III

Summary The juvenile hormone JH III, when incorporated at 1.0 ppm in the diet of adult male boll weevils (Anthonomus grandis Boh.), increased the biosynthesis of its 4 pheromone compounds by 3 times. The biosynthesis at lower and higher levels of JH III was less. JH I was not active at any of the concentrations tested.In cooperation with the Miss. Agr. and For. Exp. Sta., Miss. State, MS 39762. Mention of a proprietary product does not necessarily imply endorsement of this product by the USDA.     

Evidence for an aphrodisiac pheromone of femaleDrosophila

Summary We report here direct evidence for the involvement of a pheromone in the induction of male wing vibration, an important fixed action of theDrosophila melanogaster courtship pattern. This chemical stimulus is produced by mature females but not by mature males. The behavioral response is proportional to the pheromone concentration.Acknowledgments. Thanks are due to Drs Y. Hotta, S. Benzer and C. Descoins for stimulating discussions at the beginning of this work. Most of it was performed in the Centre de Génétique Moléculaire du C.N.R.S. We want to acknowledge their financial support.     

Avoidance of competition by spruce bark beetles,Ips typographus andPityogenes chalcographus

Bark beetles,Ips typographus andPityogenes chalcographus, attracted by synthetic or natural pheromone to Norway spruce logs,Picea abies, preferred to colonize uninfested logs rather than logs occupied by these beetles, probably as a means of avoiding intra-and interspecific competition. The aggregation pheromone components ofP. chalcographus, chalcogran and methyl (E, Z)-2,4-decadienoate, inhibited the attraction response ofI. typographus to its pheromone components (methyl butenol andcis-verbenol), while the converse was not true. However, verbenone released from colonized bark inhibited pheromonal response ofP. chalcographus.     

Dissection of the pheromone-modulated flight of moths using single-pulse response as a template

The upwind flight of male moths to conspecific females is mediated by the chemical and structural characteristics of a pheromone plume. We describe the reaction of maleCadra cautella, the almond moth, to the interception of single pulses of sex pheromone, the smallest structural units of odour plumes. Following loss of a pheromone plume, males cast, that is fly a crosswind course without progressing upwind. The response of casting males to interception of a pulse of 0.25 s duration was, after a delay of 0.21±0.07 s, to turn and briefly fly straighter upwind, resulting in average net upwind displacements of 18 cm in a 50 cm s^–1 wind. Upwind progress in the single-pulse response was the result of steering more upwind and an increase in airspeed, although average ground speed remained unchanged. During the last third of the surge, males turned crosswind, returning to casting flight. These behavioural reactions to pheromone contact and loss support the phasic-tonic model of odour-modulated flight, in which an underlying tonic counterturning rhythm, expressed upon pheromone loss, is briefly overridden by phasic upwind surges, expressed upon interception of the pheromone filament. The surge portion of the cast-surge-cast response was diminished and more crosswind if individual pulses were shorter (0.02 s), probably due to sub-optimal contact with pheromone. The cast-surge-cast response to interception of a single 0.25 s pulse was used as a template to interpret the form of flight tracks in plumes of known structure. The template matched portions of flight tracks of males flying in plumes of low pheromone pulse frequency, thus reflecting the male's pattern of pulse encounter. In plumes ensuring a high frequency of pulse interception, only the upwind surge portion of the template was expressed, resulting in nearly straight upwind flight tracks. Similar nearly straight upwind flight tracks occurred in flights along plumes of low pulse frequency with large volume. Thus flight tracks of maleC. cautella to point sources of pheromone depend on both the frequency and the size of filaments encountered.     

2-Phenylethanol, a presumed sexual stimulant produced by the male cabbage looper moth, Trichoplusia ni.

A sex pheromone produced by male cabbage looper moths, Trichoplusia ni (Hübner), has been isolated from the genital scent brushes and identified as 2-phenylethanol. It is shown conclusively to elicit specific behavioural responses in the female (such as wing vibration and abdominal elevation), as determined by a novel behavioural laboratory bioassay. This is taken as further evidence that the male pheromone of T. ni acts as a sexual stimulant (aphrodisiac) prior to mating. 2-Phenylethanol represents the first identification of a genital scent brush pheromone in the family Noctuidae, and of a male pheromone in the subfamily Plusiinae.     

Tissue distribution and substrate specificity of an epoxide hydrase in the gypsy moth,Lymantria dispar

The stereoselectivity of the enzymatic hydration of disparlure, the pheromone for the gypsy mothLymantria dispar, and for twomeso analogues was determined. A single expoxide hydrase (EH), present in various male and female moth tissues, converted disparlure and the analogues to their respectivethreo-(R,R)-diols with high stereoselectivity as determined by analysis of the diols by chiral phase capillary gas chromatography. This EH recognizes thecis-nature of the dialkyl oxirane, but shows poor discrimination of the two alkyl chains.     

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     

Are host plants important in pheromone-mediated mating systems of lepidoptera?

Summary The role of host plants in the synthesis and release of lepidopteran sex pheromones is examined. Females synthesise pheromones de novo and pheromone quality is not markedly influenced by larval food sources. However, host plants may have a significant effect on different physiological and behavioural parameters associated with pheromone production. Males in some species of Nymphalidae and Arctiidae use secondary plant compounds, such as pyrrolizidine alkaloids, as a pheromone precursor. In such cases these plant compounds serve an additional role, such as protection against predation, and may reflect potential male reproductive investment. In the one instance where the effect of larval host plants on the de novo synthesis of a male sex pheromone was examined, larval nutrition did not alter either the quality or quantity of the hairpencil contents.     

Endogenous suppression of pheromone production in virgin female moths

Summary Sexual receptivity generally is reduced in moths after mating. We found that even in virginHeliothis zea females the titer of pheromone declines after the third night of adult life, although the number of eggs laid increases. Reduction in pheromone titer is not due to reduced amounts of pheromone biosynthesis activating neuropeptide. We have discovered that a substance present in the bursa, ovaries and hemolymph of senescing virgins suppresses pheromone production. A similar factor was found in 2-day-old mated females indicating that both virgin and mated females use this factor to suppress pheromone production.     

Response ofHeliothis virescens to pheromonal components and an inhibitor in olfactometers

Summary Laboratory-reared males ofHeliothis virescens (F.) that were released in olfactometers in the laboratory were attracted to theH. virescens synthetic pheromone, but not to (Z)-9-tetradecen-1-ol formate (Z-9-TDF), or to either pheromonal component, (Z)-11-hexadecenal (Z-11-HDAL) or (Z)-9-tetradecenal (Z-9-TDAL). Also, they did not respond to the pheromone when it was dispersed simultaneously with Z-9-TDF. The proximity of the test chemicals in the olfactometer made little, if any, difference in the response ofH. virescens males to the pheromone source. Preexposure to the synthetic pheromone, Z-9-TDF, Z-11-HDAL, or Z-9-TDAL greatly reduced the number ofH. virescens males responding to the pheromone. This reduction was probably caused by habituation of the moths to these chemicals.The authors wish to thank A. H. Baumhover, E. Hart and other personnel of the Tobacco Research Laboratory, Oxford, N. C., for supplying many of the insects used in these studies.     

Stereoselectivity in mammalian chemical communication: Male mouse pheromones

Two male mouse pheromones, 3,4-dehydro-exo-brevicomin (DHB) and 2-sec-butyldihydrothiazole (SBT), are chiral molecules which were previously tested in their respective bioasays as racemic mixtures. The focus of this study has been to determine the absolute configuration of their natural forms and its relation to stereospecific biological action. DHB was established as the R,R-enantiomer possessing biological activity. Due to an extremely easy racemization of SBT under very mild conditions, enantioselectivity of its transmission and its action at the receptor site appear to be of secondary importance.     

o-Aminoacetophenone,a pheromone that repels honeybees (Apis mellifera L.)

Summary o-Aminoacetophenone is a pheromone produced by virgin honeybee queens and released with feces. In small social groups, the pheromone repels and is used to terminate agonistic interactions between queens and workers.     

Influence of larval diapause on pheromone communication in the khapra beetle,Trogoderma granarium everts

Summary InTrogoderma granarium, induction of larval diapause by sub-optimal temperature enhanced the efficiency of pheromone perception by adult males. Such diapause also altered the pattern of pheromone production by females.