Alarm substances of the stingless bee,Trigona silvestriana

2-Nonanol, 2-heptanol, octyl decanoate, and octyl octanoate were identified from the heads ofTrigona silvestriana workers. When presented at the nest, 2-nonanol, 2-heptanol, and the mixture of the four compounds elicited angular flights, landing, and buzzing of guard bees. Octyl octanoate elicited a weaker response. No response was given to octyl decanoate, to the ether solvent, or to the control volatile, vanillin.     

Formic acid in caustic cephalic secretions of stingless bee,Oxytrigona (Hymenoptera: Apidae)

The cephalic extracts of two species in the stingless bee genusOxytrigona were analyzed. Extracts made in diethyl ether, and then derivatized with diphenyldiazomethane, revealed large quantities of formic acid, potentially a major defensive secretion of this stingless bee group. We additionally identify several hydrocarbons, aldehydes, ketones, and acetates. Novel diketones identified by others were detected in both species.     

Intranidal worker reactions to volatile compounds identified from cephalic secretions in the stingless bee,Scaptotrigona postica (Hymenoptera,Meliponinae)

From pentane extracts of worker heads of the stingless bee (Scaptotrigona postica), 70 volatile compounds were identified by combined gas chromatographic-mass spectroscopic analyses. A bioassay was developed to evaluate intranidal reactions of workers to synthetic volatiles. Thirty-six of the cephalic volatiles were tested. Thirteen types of behavioral reactions were recorded in a semiquantitative manner. The test was run in the brood nest where mainly young nurse bees are present and also in the storage area of the nest with old foragers traffic. The results obtained were compared and discussed in order to understand the chemical communication system of this species. Especially in the dark interior of the nest, which in nature is found in hollow tree cavities, chemical messages obviously play a particularly important role in the communication systems of the bees.     

Robber bees (Lestrimelitta limao) and their host chemical and visual cues in nest defense byTrigona (Tetragonisca) angustula (Apidae: Meliponinae)

The nest of the stingless bee,Trigona (Tetragonisca) angustula, is guarded by bees positioned in the nest entrance and others hovering in front of it. Hovering guard bees track returning foragers sideways along the last 10 cm in front of the nest, but intercept and incapacitate nest intruders by clinging with mandibles to wings and legs. When attacked by the cleptobiotic stingless beeLestrimelitta limao, the colony strengthens its aerial defense with hundreds of additional hoverers. To test our hypothesis that this reaction is due to interspecific chemical communication based on kairomone effects, we presented synthetic cephalic volatiles of both species at the nest entrance and counted the number of bees leaving the nest and taking up hovering positions. We conclude that guard bees recognizeL. limao by the major terpenoids of their volatile cephalic secretions, geranial, neral (=citral) and 6-methyl-5-hepten-2-one; other components may fine-tune this recognition. The effect of chemical stimuli is not significantly enhanced by combination with a dummy ofL. limao. Guard bees, we hypothesize, respond to this kairomone by secreting a species specific alarm pheromone; a major component of this pheromone, benzaldehyde, recruits additional bees to defend the nest.     

Host recognition and the study of a chemical basis for attraction by cuckoo bumble bees (Hymenoptera: Apidae)

Species ofPsithyrus (Hymenoptera; Apidae) are obligate bumble bee social parasites. In this study, females ofP. vestalis andP. ashtoni were presented with pentane extracts prepared from different body parts of queens of their respective host species,Bombus terrestris andB. terricola. Parasites of both species were capable of distinguishing host bees from other bumble bee species using chemical cues contained within extracts. Among extracts of several body parts presented to parasites, the abdomen produced the greatest behavioral response, with Dufour's gland and terminal tergal segments eliciting the greatest response among abdominal regions. Extracts of these two body parts obtained fromB. terrestris queens shared a number of compounds, identified by GC-MS. Among the identified compounds are a number that have been reported to be of importance in bee sociochemistry.     

Linalool in mandibular gland secretion ofColletes bees (Hymenoptera: Apoidea)

Uinalool was identified as the main component of the mandibular gland secretion in females and males of four species ofColletes bees, viz.,C. cunicularius, C. daviesanus, C. impunctatus andC. succinctus. It was also shown to be the dominant volatile compound in the same gland in maleC. floralis (the female of this species has not yet been investigated). Further, in another species,C. similis, linalool is present in the mandibular gland secretions of females and males, but the dominant volatile component in these secretions is geranial, together with neral. Females of the speciesC. fodiens seem to lack monoterpenes altogether; nonadecane is the dominant volatile compound of the cephalic secretion (based on analysis of a single individual). When linalool is put out in the area of nest aggregation ofC. cunicularius, where the males are patrolling, a distinct increase in flight activity is noted. The function of linalool is discussed on the basis of field observations.This report forms part XXI in the series Studies on Natural Odoriferous Compounds.     

Dufour's gland and its role in secretion of nest cell lining in bees of the genusColletes (Hymenoptera: Colletidae)

The liquid secretion of the Dufour's gland in mated females comprises a mixture of macrocyclic lactones, straight chain mono- and dicarboxylic acids, together with trace amounts of di- and trihydroxy monocarboxylic acids and a series ofn-alkanes. Polymerization of the liquid to form the membranous nest cell lining, which also contains alanine and glutamic acid as major constituents, may be mediated by an enzyme from the thoracic salivary gland and voided via the mouth. The composition and structure of the cell linings are similar to those of Wigglesworth's cuticulin.     

Nasonov pheromone of the honeybee.Apis mellifera L. (Hymenoptera,Apidae)

Electroantennogram (EAG) responses from worker honeybee antennae were obtained for each Nasonov component. Response amplitudes to 10 g of components correlated well with reported relative abilities to attract foragers in the field. EAG responses of worker, queen, and drone antennae to natural pheromone were consistently greater than to synthetic pheromone, a difference only partly explained by enzymic conversion of geraniol to (E)-citral during preparation of natural extracts.     

(Z)-11-eicosen-1-ol,an important new pheromonal component from the sting of the honey bee,Apis mellifera L. (Hymenoptera,Apidae.)

(Z)-11-Eicosen-1-ol was identified by GC-MS and microchemical methods as a major volatile component, ca. 5 g per insect, secreted by the sting apparatus of the worker honey bee. When presented on moving lures at the hive entrance, (Z)-11-eicosen-1-ol, like isopentyl acetate already known as an alarm pheromone, elicited stinging, and together these two compounds were as active as the natural pheromone from the sting. On stationary lures, (Z)-11-eicosen-1-ol prolonged the effectiveness of isopentyl acetate.     

Nasonov pheromone of the honey bee,Apis mellifera L. (Hymenoptera,Apidae). part III.

GC and GC-MS analyses of the multicomponent Nasonov pheromone of the honey bee, and of the air above insects releasing the pheromone, show that constant composition is maintained during release, despite differing volatilities of the components. The regulating mechanism may involve a specific enzyme process, detected in excised Nasonov glands, which converts the major component geraniol into the more volatile (E)-citral. Analysis of honey bees of known ages and at different times of year shows that maximum secretion occurs when foraging is most likely.     

Mandibular glands of maleCentris adani, (Hymenoptera: Anthophoridae)

Males of the solitary Central American beeCentris adani Cockerell possess enlarged mandibular glands filled with a fragrant fluid that was shown by gas chromatographic and mass spectral analysis to consist of nerol, geraniol, neral, ethyl laurate, and geranyl acetate. Male bees set up territories by marking a semicircular array of grass stems with these compounds. Grass stems marked by the bees showed the presence of the same chemicals.Approved as TA 16466 by the Director, Texas Agricultural Experiment Station. All programs and information of the Texas Agricultural Experiment Station are available without regard to race, ethnic origin, religion, sex or age. Supported in part by NSF grant DEB 7063936 and the National Geographic Society.     

Function of glandular secretions in fragrance collection by male euglossine bees (Apidae: Euglossini)

MaleEulaema cingulata (Fabricius) (Apidae: Euglossini) possess large cephalic labial glands that secrete a mixture of lipids. In the process of fragrance collection, males secrete the labial gland lipids onto the substrate. The mixture of lipids and fragrances is then taken up by the front tarsal brushes and transferred to the hind tibial organs. The labial gland secretions apparently serve as a nonpolar solvent and carrier that increases the efficiency of fragrance collection.     

Termite predation byMegaponera foetens (FAB.) (Hymenoptera: Formicidae)

Termite predation by the ponerine ant,Megaponera foetens, is coordinated by chemicals from at least two glands. Columns of ants are guided to termite foraging areas by pheromones originating from the poison apparatus. On finding groups of termites, ants release alkyl sulfides (dimethyl disulfide and trisulfide) from their mandibular glands which attract sister workers who dig, into the termite galleries, in response to other unidentified mandibular gland pheromones.     

Chemical communication in the dacetine antDaceton armigerum (Hymenoptera: Formicidae)

Contrary to previous assumptions,Daceton armigerum, the largest ant in the myrmicine tribe Dacetini, employs trail communication. We identified two anatomical sources of trail pheromones: Trails drawn with poison gland contents can last for more than seven days. Trails drawn with the newly discovered sternal glands (in the VIth and VIIth abdominal sternites) are effective but relatively short-lived. In addition, our bioassays revealed that the contents of the mandibular glands elicit alarm behavior, and secretions from the pygidial gland release attraction. When tested with artificial poison gland trails from seven other myrmicine species,Daceton did not exhibit trail following behavior. We confirmed, however, previous findings thatAtta respond toDaceton poison gland trails andSolenopsis followDaceton Dufour's gland trails.     

Nasonov pheromone of the honey bee,Apis mellifera L. (Hymenoptera: Apidae)

Composition of the Nasonov pheromone of the honey bee has been reexamined using new procedures, including analysis of pheromone from single live insects by capillary column GC-MS. Two new components have been identified, nerol and (E,E)-farnesol, and the presence of components proposed previously has been confirmed. Absolute amounts or relative proportions of components in the pheromonal secretion have been determined.     

Aldehydic contact poisons and alarm pheromone of the antCrematogaster scutellaris (Hymenoptera: Myrmicinae)

The Dufour gland ofCrematogaster scutellaris stores a mixture of long-chain primary acetates bearing a cross-conjugated dienone (Scheme 1, la-c). The poison gland contains two highly active enzymes: an acetate esterase and an alcohol oxidase. During venom emission, the constituents of both glands mix and accumulate on the sting, where the formation of the highly electrophilic aldehydes (Scheme 1, 2a-c) from their acetate precursors is initiated. Acetic acid, produced during the reaction, acts as alarm pheromone. The toxicity of the acetates (Scheme 1, la-c) and of the crude secretion has been assessed by topical application onMyrmica rubra. The acetatecontaining secretion from the Dufour gland was less toxic than the enzymatically altered secretion that was rich in aldehydes. The production of acids (Scheme 1, 3a-c) was an artifact resulting from the nonenzymatic oxidation of the unstable aldehydes.     

Chemical communication during tandem running inPachycondyla obscuricornis (Hymenoptera: Formicidae)

Communication during tandem running inPachycondyla obscuricornis is chemically mediated by a pheromone produced in the pygidial gland, which is composed of a cluster of gland cells and an associated reservoir located beween the 6th and 7th tergites of the gaster. The secretion of the gland appears to be transferred to the hindlegs of a tandem pair leader by a series of self-grooming behaviors that occur prior to the formation of a tandem pair. During tandem running, the antennae of the following ant are kept in close contact with the leader's hindlegs and therefore with the chemical signal that provides a communicative bond between individuals.Dedicated to the memory of Robert E. Silberglied.     

Alarm pheromone of pentatomid bug,Erthesina fullo Thunberg (Hemiptera: Pentatomidae)

In the pentatomid bug,Erthesina fullo Thunberg, the odor of male metathoracic scent gland elicits an alarm response, making the male individuals of the same species alert and disperse; the alarm response of males is more obvious than that of females. Chemical composition of the glandular secretion was identified by gas chromatography and mass spectrometry data in comparison with authentic compounds. No sexual dimorphism exists in the glandular composition in this species. A total of 9 compounds [(E)-2-hexenal, (E)-4-keto-2-hexenal, (E)-2-hexenyl acetate,n-undecane,n-dodecane, (E)-2-decenal,n-tridecane, (E)-2-decenyl acetate, andn-pentadecane] are identified, among whichn-tridecane and (E)-4-keto-2-hexenal comprised nearly 70% of the total secretion in both females and males.     

The Nasonov pheromone of the honeybeeApis mellifera L. (Hymenoptera,Apidae). Part II. Bioassay of the components using foragers

The Nasonov pheromone of the honeybee comprises seven components, (Z)-citral, nerol, geraniol, nerolic acid, geranic acid, and (E,E)-farnesol. Bioassay of individual components showed each attracted foraging bees. A mixture of components in proportions present in the honeybee was as attractive as the natural secretion, and each component contributed to the attractiveness of the mixture. Honeybees responded anemotactically to the source of Nasonov odor. The presence of footprint pheromone enhanced the attractiveness of the synthetic Nasonov mixture. Nasonov and footprint pheromones may prove useful in attracting honeybees to crops needing pollination.     

Pheromonal cues direct mate-seeking behavior of maleColletes cunicularius (Hymenoptera: Colletidae)

Males of the vernal ground nesting bee,Colletes cunicularius, actively search their nesting aggregations for emerging virgin females. Males often detect and unearth preemergent virgin males and females which have not yet dug up to the soil surface. Field experiments indicate that the odors from one unmated individual are sufficient to both excite males and direct their excavation of the virgin bee. A volatile component of this species' mandibular gland secretion, linalool, increases flight activity and directs local search behavior in aerially patrolling males. Linalool is detectable by coupled gas chromatography-mass spectrometry in association with the digging activities of either sex.