Honeybee Pheromone Research Articles

The genome of the blind bee louse fly reveals deep convergences with its social host and illuminates Drosophila origins

Social insects' nests harbor intruders known as inquilines,1 which are usually related to their hosts.2,3 However, distant non-social inquilines may also show convergences with their hosts,4,5 although the underlying genomic changes remain unclear. We analyzed the genome of the wingless and blind bee louse fly Braula coeca, an inquiline kleptoparasite of the western honey bee, Apis mellifera.6,7 Using large phylogenomic data, we confirmed recent accounts that the bee louse fly is a drosophilid8,9 and showed that it had likely evolved from a sap-breeder ancestor associated with honeydew and scale insects' wax. Unlike many parasites, the bee louse fly genome did not show significant erosion or strict reliance on an endosymbiont, likely due to a relatively recent age of inquilinism. However, we observed a horizontal transfer of a transposon and a striking parallel evolution in a set of gene families between the honey bee and the bee louse fly. Convergences included genes potentially involved in metabolism and immunity and the loss of nearly all bitter-tasting gustatory receptors, in agreement with life in a protective nest and a diet of honey, pollen, and beeswax. Vision and odorant receptor genes also exhibited rapid losses. Only genes whose orthologs in the closely related Drosophila melanogaster respond to honey bee pheromone components or floral aroma were retained, whereas the losses included orthologous receptors responsive to the anti-ovarian honey bee queen pheromones. Hence, deep genomic convergences can underlie major phenotypic transitions during the evolution of inquilinism between non-social parasites and their social hosts.

Varroa destructor relies on physical cues to feed in artificial conditions

Olfaction is a major sense in Varroa destructor. In natural conditions, it is known that this honey bee parasite relies on kairomones to detect its host or to reproduce. Yet, in artificial conditions, the parasite is able to feed and survive for a few days even though most honey bee pheromones are lacking. Other key cues are thus probably involved in V. destructor perception of its close environment. Here, we used several artificial feeding designs to explore the feeding behaviour of the parasite when it is deprived of olfactory cues. We found that V. destructor is still able to feed only guided by physical cues. The detection of the food source seems to be shape-related as a 3D membrane triggers arrestment and exploration more than a 2D membrane. The tactile sense of V. destructor could thus be essential to detect a feeding site, although further studies are needed to assess the importance of this sense combined with olfaction in natural conditions.

Research progress of the interaction between Apis mellifera and Varroa destructor mediated by pheromones

Varroa destructor is a virulent ectoparasitic mite of western honeybee (Apis mellifera), and considered the greatest threat to apiculture around the world. Chemical method is widely used for the management of this mite. However, this method can easily induce the resistance of V. destructor to acaricides, toxicity of acaricides to honeybee and the residues in bee products. Therefore, many safe preventions and control techniques were developed to treat mite in recent years. Using pheromones of honeybee to control V. destructor would be a main tendency. A lot of studies indicated that Varroa mites are able to use honeybee pheromones to distinguish the development stages of the hosts, and show high selectivity for appropriate hosts at a special stage. In recent years, a lot of honey bee pheromones were reported to have effect on V. destructor, including pheromones from adult honeybee, pupa and brood. Some of them have repellent effect on V. destructor, while others have attractant effect on V. destructor. This article reviewed the progresses in pheromones categories, major chemical compositions, and their effects to V. destructor, which would suggest important avenues for further researches and applications in mite control.

Nectar Attracts Foraging Honey Bees with Components of Their Queen Pheromones.

Floral nectar often contains chemicals that are deterrent to pollinators, presenting potential challenges to outcrossing plant species. Plants may be able to co-opt pollinator chemical signals to mitigate the negative effects of nectar deterrent compounds on pollination services. We found that buckwheat (Fagopyrum esculentum) and Mexican sunflower (Tithonia diversifolia) produce nectar with abundant phenolics, including three components of the Apis honeybee queen mandibular pheromone (QMP). In addition, these nectars contain a non-pheromonal phenolic, chlorogenic acid (CA), which was toxic to honeybees, and T. diversifolia nectar also contained isochlorogenic acid (IA). Fresh nectar or solutions containing nectar phenolics reduced Apis individual feeding compared to sucrose solutions. However, freely foraging bees preferred solutions with QMP components to control solutions, and QMP components over-rode or reversed avoidance of CA and IA. Furthermore, prior exposure to the presence or just the odor of QMP components removed the deterrent effects of CA and IA. By mimicking the honey bee pheromone blend, nectar may maintain pollinator attraction in spite of deterrent nectar compounds.

How flies respond to honey bee pheromone: the role of the foraging gene on reproductive response to queen mandibular pheromone

In this study we test one central prediction from sociogenomic theory--that social and non-social taxa share common genetic toolkits that regulate reproduction in response to environmental cues. We exposed Drosophila females of rover (for(R)) and sitter (for(s)) genotypes to an ovary-suppressing pheromone derived from the honeybee Apis mellifera. Surprisingly, queen mandibular pheromone (QMP) affected several measures of fitness in flies, and in a manner comparable to the pheromone's normal effect on bee workers. QMP-treated sitter flies had smaller ovaries that contained fewer eggs than did untreated controls. QMP-treated rover flies, by contrast, showed a more variable pattern that only sometimes resulted in ovary inhibition, while a third strain of fly that contains a sitter mutant allele in a rover background (for(s2)) showed no ovarian response to QMP. Taken together, our results suggest that distinctly non-social insects have some capacity to respond to social cues, but that this response varies with fly genotype. In general, the interspecific response is consistent with a conserved gene set affecting reproductive physiology. The differential response among strains in particular suggests that for is itself important for modulating the fly's pheromonal response.

Regulation of brain gene expression in honey bees by brood pheromone

Pheromones are very important in animal communication. To learn more about the molecular basis of pheromone action, we studied the effects of a potent honey bee pheromone on brain gene expression. Brood pheromone (BP) caused changes in the expression of hundreds of genes in the bee brain in a manner consistent with its known effects on behavioral maturation. Brood pheromone exposure in young bees causes a delay in the transition from working in the hive to foraging, and we found that BP treatment tended to upregulate genes in the brain that are upregulated in bees specialized on brood care but downregulate genes that are upregulated in foragers. However, the effects of BP were age dependent; this pattern was reversed when older bees were tested, consistent with the stimulation of foraging by BP in older bees already competent to forage. These results support the idea that one way that pheromones influence behavior is by orchestrating large-scale changes in brain gene expression. We also found evidence for a relationship between cis and BP regulation of brain gene expression, with several cis-regulatory motifs statistically overrepresented in the promoter regions of genes regulated by BP. Transcription factors that target a few of these motifs have already been implicated in the regulation of bee behavior. Together these results demonstrate strong connections between pheromone effects, behavior, and regulation of brain gene expression.

Practical Synthesis of (E)‐α,β‐Unsaturated Carboxylic Acids Using a One‐Pot Hydroformylation/Decarboxylative Knoevenagel Reaction Sequence

AbstractCombining the regioselective room temperature/ambient pressure hydroformylation and a modification of the Doebner–Knoevenagel reaction allowed for the development of an efficient, one‐pot procedure for the synthesis of (E)‐α,β‐unsaturated carboxylic acids. The reaction proceeds under mild conditions, tolerates a variety of functional groups and gives (E)‐α,β‐unsaturated carboxylic acids in good yields and with excellent regio‐ and stereocontrol. The practicability of this process has been demonstrated by a short protecting group‐free synthesis of the queen honeybee pheromones 9‐ODA [(E)‐9‐oxodec‐2‐enoic acid] and 9‐HDA [(E)‐9‐hydroxydec‐2‐enoic acid].

Practical Synthesis of (E)-α,β-Unsaturated Carboxylic Acids Using a One-Pot Hydroformylation/Decarboxylative Knoevenagel Reaction Sequence

Combining the regioselective room temperature/ambient pressure hydroformylation and a modification of the Doebner-Knoevenagel reaction allowed for the development of an efficient, one-pot procedure for the synthesis of (E)-α,β-unsaturated carboxylic acids. The reaction proceeds under mild conditions, tolerates a variety of functional groups and gives (E)-α,β-unsaturated carboxylic acids in good yields and with excellent regio- and stereocontrol. The practicability of this process has been demonstrated by a short protecting group-free synthesis of the queen honeybee pheromones 9-ODA [(E)-9-oxodec-2-enoic acid] and 9-HDA [(E)-9-hydroxydec-2-enoic acid].

Pheromones in the life of insects

Life in insect societies asks for a permanent flow of information, often carried by rather simple organic molecules. Some originate from plants as odours of blossoms or exudates from trees. Especially important are the intra- and interspecific combinations of compounds produced by the insects themselves. These are called pheromones or ecto-hormones and serve a variety of tasks. The paper deals mainly with honeybee pheromones, but takes also into consideration those of wasps and hornets. Effects of pheromones are monitored ethologically by direct observation and filming as well as in a more quantitative manner with using direct and indirect calorimetry. In all experimental set-ups alarm pheromones were used as controls. They show an up to fourfold increase of activity after a few seconds, determined for small groups of insects as well as for a whole hornet nest placed in a 25-l calorimeter. A variety of cosmetics like soaps, shampoos, lotions and perfumes are included in the investigations because of repeated reports about unwarranted insect attacks which are said to be provoked by such products. None of the applied substances provoked a significant reaction of the bees (p > 0.05). A short appendix discusses the still questionable existence of pheromones in man, which were confirmed under laboratory conditions, but not yet for daily life.

Cued in: honey bee pheromones as information flow and collective decision-making

Recent studies using diverse disciplines ranging from classical behavioral assays to quantitative trait locus mapping, have revealed that chemical communication in honey bees is generally complex. Pheromones that are blends of multiple components are the rule rather than the exception. Subsets of multiple component blends regulate common and different systems. Reviewed are recent studies in pheromone regulation of colony defense, foraging ontogeny, and retinue behavior. Honey bee chemical communication is discussed as an emergent property of a complex system with dynamic properties calling for a complex systems approach of analysis. Apis mellifera / pheromone / chemical communication / social regulation / emergent property / complex system

Worker honey bee pheromone regulation of foraging ontogeny.

The evolution of sociality has configured communication chemicals, called primer pheromones, which play key roles in regulating the organization of social life. Primer pheromones exert relatively slow effects that fundamentally alter developmental, physiological, and neural systems. Here, I demonstrate how substances extracted from the surface of foraging and young pre-foraging worker bees regulated age at onset of foraging, a developmental process. Hexane-extractable compounds washed from foraging workers increased foraging age compared with controls, whereas extracts of young pre-foraging workers decreased foraging age. This represents the first known direct demonstration of primer pheromone activity derived from adult worker bees.

Tungsten(0) alkylidene complexes stabilized as pyridinium ylides: new aspects of their synthesis and reactivity

The interaction of dihydropyridines with alkoxycarbene complexes of tungsten has been shown to lead to pyridinium ylid complexes: this transformation has now been applied to the synthesis of a hydroxyl-containing ylid complex by ring-opening of the pentacarbonyl (2-oxacyclopentylidene) tungsten(0) complex and to the synthesis of a series of chiral ylid complexes both from chiral and non-chiral carbene complexes by the use of dihydropyridines and dihydronicotines, respectively. The transfer of the alkylidene moiety of these complexes to nucleophilic olefins will be outlined and discussed. Especially relevant is the interaction of these pyridinium ylid complexes with unsaturated substrates such as dihydropyridines, enamines, and β-alkoxy bis(trimethylsilyl) ketene acetals. This latter reaction leads to conjugated carboxylic acids, and has been be applied to a new synthesis of a honey bee pheromone, the queen substance.

Honey bee primer pheromones and colony organization: gaps in our knowledge

The purpose of this article is to discuss gaps in our knowledge concerning how honey bee primer pheromones mediate worker activities and colony functions. We first review the chemical structure and functions of queen mandibular pheromone (QMP), but then focus primarily on areas of potential future research interest. We discuss the mode of action that QMP may have on workers, address the issue of why QMP is a complex blend of five components, propose an evolutionary pathway for pheromone complexity in the genus Apis, discuss biochemical differences between worker and queen mandibular glands, review the evidence for additional queen pheromones besides QMP, examine how queen and brood pheromones interact to mediate colony biology, and discuss the relative importance of congestion and population size in pheromone transmission. Finally, we suggest some research areas that involve commercial applications of honey bee pheromones for beekeeping and crop pollination.

Spiroacetals and Other Venom Constituents as Potential Wasp Attractants

The major volatile spiroacetals from the venom of both the common wasp, Vespula vulgaris and the German wasp V. germanica, viz. 7-methyl-1,6-dioxaspiro[4,5]decane and 7-ethyl-2-methyl-1,6-dioxaspiro-[4,5]decane, respectively, were synthesized by known methods. These acetals, along with N-isopentylacetamide (the major volatile amide from wasp venom), 2-heptanone (a honeybee pheromone), 2-methyl-3-buten-2-ol (a component of hornet venom), cuticle wax from V. vulgaris, and venom sacs from both wasp species were assayed by EAG and olfactory bioassay for attractancy to V. vulgaris workers. Antennal responses to all test chemicals were recorded. Acetal isomers (±)-2 and (±)-3, N-isopentylacetamide, and 2-heptanone were attractive to V. vulgaris workers at levels of <1 μmol. Greater quantities of the same compounds were repellent to V. vulgaris workers.

ChemInform Abstract: A Microbial Synthesis of (R)‐ and (S)‐9‐Hydroxy‐(E)‐2‐decenoic Acid (9‐ HDA), a Queen Honeybee Pheromone.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

A microbial synthesis of R and S-9-hydroxy-(E)-2-decenoic acid(9-HDA), a queen honeybee pheromone

(R,E)-9-hydroxy-2-decenoic acid (9-HDA) its (S,E)- isomer have been prepared by using an organic-microbial approach.

Cornbined Gas Chromatography-Electroantennogram Characterization of Alfalfa Floral Volatiles Recognized by Honey Bees (Hymenoptera: Apidae)

This study was designed to investigate antennal response of honey bees, Apis mellifera L., to alfalfa /loral volatiles and to assess among- and within-hive variation in average antennal response to these Cornpounds. Ten of the principal ( Medicago sativa L.) alfalfa floral volatiles were analyzed for honey bee antennal response using a Cornbined gas chromatography-electroantennal detector system. All 10 alfalfa floral volatiles elicited antennal responses, and significant differences were observed in average honey bee antennal response to these 10 Cornpounds. Linalool and methyl salicylate elicited “sticky” antennal signals (slow recovery toward baseline physio-electrical output). This “sticky” response may suggest a biologically active role for these two Cornpounds. Support for a biologically active role for linalool and cis -3-hexenyl acetate Cornes from the chemical and structural similarity between these two Cornpounds and two honey bee pheromones, geraniol (nasonov) and n-hexyl acetate (alarm), respectively. Selection for increased emanation of linalool and methyl salicylate, and decreased emanation of cis -3-hexenyl acetate, is suggested as a possible method for increasing the attractiveness of alfalfa to honey bees. Finally, significant differences were demonstrated in both among- and within-hive average antennal response to most of the volatile Cornpounds. Based on the results of this study and those of other investigators, we hypothesize that host-pollinator interrelationships can be strengthened by directed selection in both honey bees and alfalfa.

Effects of honey-bee alarm pheromone compounds on the behaviour of Varroa jacobsoni

Analyse de l'influence de la presence du dard et de certains composes de la pheromone d'alarme de A. mellifera sur la repulsion de V. jacobsoni en comparant son comportement face a des abeilles mortes de froid, ou mortes par piqure d'abeille, ou un cadavre d'abeille contenant differents composes pheromonaux

The influence of age and task specialization on the production and perception of honey bee pheromones

The production and perception of honey bee pheromones were studied in workers of different ages and task specializations. Electroantennogram responses increased to a maximum by days 6–12 and no differences were seen between bees performing different tasks. Levels of production of isopentyl acetate, octyl acetate, ( E)-2-octenyl acetate, butyl acetate, and hexyl acetate increased with age to maximal levels at days 30–40. Production of 2-nonanol, 2-nonyl acetate, benzyl acetate, and benzyl alcohol differed from the above compounds, with most workers producing very low levels and a few producing very high levels. When examined by task specialization, foragers produced higher levels of benzyl acetate, benzyl alcohol, and 2-nonanol than guards, fanners, or comb bees respectively.

Techniques for studying honeybee pheromones involved in clustering, and experiments on the effect of Nasonov and queen pheromones

ABSTRACT. Techniques for investigating pheromones responsible for clustering in Apis mellifera are described. Stable queenless clusters were formed in response to synthetic Nasonov pheromone mixed with (E)‐9‐oxo‐2‐decenoic acid. This mixture plus the addition of (E)‐9‐hydroxy‐2‐decenoic acid was less potent in initiating cluster formation than it was without this addition, but the clusters once formed sometimes grew larger. Other unknown components from the queen's mandibular glands encouraged cluster formation.