Honey bee pheromones
Encyclopedia
The pheromone
Pheromone
A pheromone is a secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting outside the body of the secreting individual to impact the behavior of the receiving individual...

s of the Honey bee
Honey bee
Honey bees are a subset of bees in the genus Apis, primarily distinguished by the production and storage of honey and the construction of perennial, colonial nests out of wax. Honey bees are the only extant members of the tribe Apini, all in the genus Apis...

 are mixtures of chemical substances released by individual bees into the hive or environment that cause changes in the physiology and behaviour of other bees.

Introduction

Honeybees have one of the most complex pheromonal communication systems found in nature, possessing 15 known glands that produce an array of compounds. Pheromones are produced as a liquid and transmitted by direct contact as a liquid or as a vapor. Pheromone
Pheromone
A pheromone is a secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting outside the body of the secreting individual to impact the behavior of the receiving individual...

s may be volatile or non-volatile.

The pheromones are chemical messengers secreted by a queen
Queen bee
The term queen bee is typically used to refer to an adult, mated female that lives in a honey bee colony or hive; she is usually the mother of most, if not all, the bees in the hive. The queens are developed from larvae selected by worker bees and specially fed in order to become sexually mature...

, drone
Drone (bee)
Drones are male honey bees. They develop from eggs that have not been fertilized, and they cannot sting, since the worker bee's stinger is a modified ovipositor .-Etymology:...

, worker bee
Worker bee
A Worker bee is any female eusocial bee that lacks the full reproductive capacity of the colony's queen bee; under most circumstances, this is correlated to an increase in certain non-reproductive activities relative to a queen, as well...

 or laying worker bee that elicit a response in other bees. The chemical messages are received by the bee's antenna and other body parts. Honey bee (Apis mellifera) pheromones can be grouped into releaser pheromones with short term effects and primer pheromones with long term effects.

Primer pheromones change the physiology of the recipient. Releaser pheromones change the behavior of the recipient. Releaser pheromones have a short term effect and they trigger an almost immediate behavioral response from the receiving bee. Under certain conditions a pheromone can act as both a releaser and primer pheromone.

Pheromones may either be single chemicals or a complex mixture of numerous chemicals in different percentages.

Alarm pheromone

Two main alarm pheromones have been identified in honeybee workers. One is released by the Koschevnikov gland
Koschevnikov gland
The Koschevnikov gland is a gland of the honeybee. It is located near the sting shaft. The gland produces an alarm pheromone which is released when a bee stings. The pheromone contains more than 40 different compounds, including pentylacetate, butylacetate, 1-hexanol, n-butanol, octanol,...

, near the sting shaft, and consists of more than 40 chemical compounds, including isopentyl acetate (IPA), butyl acetate
Butyl acetate
n-Butyl acetate, also known as butyl ethanoate, is an organic compound commonly used as a solvent in the production of lacquers and other products. It is also used as a synthetic fruit flavoring in foods such as candy, ice cream, cheeses, and baked goods. Butyl acetate is found in many types of...

, 1-hexanol
1-Hexanol
1-Hexanol is an organic alcohol with a six-carbon chain and a condensed structural formula of CH35OH. This colorless liquid is slightly soluble in water, but miscible with ether and ethanol. Two additional straight chain isomers of 1-hexanol, 2-hexanol and 3-hexanol, exist, both of which...

, n-butanol
N-Butanol
n-Butanol or n-butyl alcohol or normal butanol is a primary alcohol with a 4-carbon structure and the molecular formula C4H9OH. Its isomers include isobutanol, 2-butanol, and tert-butanol...

, 1-octanol, hexyl acetate
Hexyl acetate
Hexyl acetate is an ester with the molecular formula C8H16O2. It is mainly used as a solvent for resins, polymers, fats and oils. It is also used as a paint additive to improve its dispersion on a surface....

, octyl acetate
Octyl acetate
Octyl acetate, or octyl ethanoate, is an ester that is formed from octanol and acetic acid.Octyl acetate can be synthesized by a condensation reaction:-Use:...

, n-pentyl acetate and 2-nonanol
2-Nonanol
2-Nonanol is a simple alcohol. It has the odor of cucumber, and has been identified in oysters. It is used by several insects as pheromones. It is commercially available....

. These chemical compounds have low molecular weights, are highly volatile, and appear to be the least specific of all pheromones. Alarm pheromones are released when a bee stings another animal, and attract other bees to the location and causes the other bees to behave defensively, i.e. sting or charge. It has been suggested that the alarm pheromone emitted when a bee stings another animal smells like bananas. Smoke can mask the bees' alarm pheromone.
The other alarm pheromone is released by the mandibular glands and consists of 2-heptanone
2-Heptanone
2-Heptanone, or methyl n-amyl ketone, is a ketone with the molecular formula C7H14O. It is a colorless, water-white liquid with a banana-like, fruity odor....

, which is also a highly volatile substance. This compound has a repellent effect and it was proposed that it is used to deter potential enemies and robber bees. Interestingly, the amounts of 2-heptanone increase with the age of bees and becomes higher in the case of foragers. It was therefore suggested that 2-heptanone is used by foragers to scent-mark recently visited and depleted foragers, which indeed are avoided by foraging bees.

Brood recognition pheromone

Another pheromone is responsible for preventing worker bees
Laying worker bee
A laying worker bee is a worker bee that lays unfertilized eggs usually in the absence of a queen bee. Only drones develop from the eggs of laying worker bees . A beehive cannot survive with only a laying worker bee....

 from bearing offspring in a colony that still has developing young. Both larvae and pupae emit a "brood recognition" pheromone. This inhibits ovarian development in worker bees and helps nurse bees distinguish worker larvae from drone larvae and pupae. This pheromone is a ten-component blend of fatty-acid esters, which also modulates adult caste ratios and foraging ontogeny dependent on its concentration. The components of brood pheromone have been shown to vary with the age of the developing bee. An artificial brood pheromone was invented by Yves Le Conte,
Leam Sreng, Jérome Trouiller, and Serge Henri Poitou and patented in 1996.

Drone pheromone

Drones produce a pheromone that attracts other flying drones to promote drone aggregations at sites suitable for mating with virgin queens.

Dufour's gland pheromone

The Dufour’s gland (named after the French naturalist Léon Jean Marie Dufour
Léon Jean Marie Dufour
Léon Jean Marie Dufour was a French medical doctor and naturalist .Between 1799 and 1806 he studied medicine in Paris then returned to Saint-Sever in the Landes...

) opens into the dorsal vaginal wall. Dufour’s gland and its secretion have been somewhat of a mystery. The gland secretes its alkaline products in to the vaginal cavity, and it has been assumed to be deposited on the eggs as they are laid. Indeed, Dufour’s secretions allow worker bees to distinguish between eggs laid by the queen, which are attractive, and those laid by workers. The complex of as many as 24 chemicals differs between workers in "queenright" colonies and workers of queenless colonies. In the latter, the workers’ Dufour secretions are similar to those of a healthy queen. The secretions of workers in queenright colonies are long-chain alkanes with odd numbers of carbon atoms, but those of egg-laying queens and egg-laying workers of queenless colonies also include long chain esters.

Egg marking pheromone

This pheromone, similar to that described above, helps nurse bees distinguish between eggs laid by the queen bee and eggs laid by a laying worker.

Footprint pheromone

This pheromone is left by bees when they walk and is useful in enhancing Nasonov pheromones in searching for nectar.

In the queen, it is an oily secretion of the queen's tarsal glands that is deposited on the comb as she walks across it. This inhibits queen cell construction (thereby inhibiting swarming), and its production diminishes as the queen ages.

Forager pheromone

Ethyl oleate
Ethyl oleate
Ethyl oleate is the ester formed by the condensation of the fatty acid oleic acid and ethanol. It is a colorless to light yellow liquid. Ethyl oleate is produced by the body during ethanol intoxication....

 is released by older forager bees to slow the maturing of nurse bees. This primer pheromone acts as a distributed regulator to keep the ratio of nurse bees to forager bees in the balance that is most beneficial to the hive.

Nasonov
Nasonov
The Nasonov pheromone is released by worker bees to orient returning forager bees back to the colony. To broadcast this scent, bees raise their abdomens, which contain the Nasonov glands, and fan their wings vigorously....

 pheromone

This pheromone is emitted by the worker bee
Worker bee
A Worker bee is any female eusocial bee that lacks the full reproductive capacity of the colony's queen bee; under most circumstances, this is correlated to an increase in certain non-reproductive activities relative to a queen, as well...

s and used for orientation.

Other pheromones

Other pheromones produced by most honeybees include rectal gland pheromone, tarsal pheromone, wax gland and comb pheromone, and tergite gland pheromone.

Queen mandibular pheromone
Queen mandibular pheromone
Queen Mandibular Pheromone, or QMP, is a honey bee pheromone produced by the queen and fed to her attendants who share it with the rest of the colony that gives the colony the sense of being queenright. Chemically QMP is very diverse with at least 17 major components and other minor ones...

 (QMP)

QMP, emitted by the queen, is one of the most important sets of pheromones in the bee hive. It affects social behaviour, maintenance of the hive, swarming, mating behaviour, and inhibition of ovary
Ovary
The ovary is an ovum-producing reproductive organ, often found in pairs as part of the vertebrate female reproductive system. Ovaries in anatomically female individuals are analogous to testes in anatomically male individuals, in that they are both gonads and endocrine glands.-Human anatomy:Ovaries...

 development in worker bee
Worker bee
A Worker bee is any female eusocial bee that lacks the full reproductive capacity of the colony's queen bee; under most circumstances, this is correlated to an increase in certain non-reproductive activities relative to a queen, as well...

s. The effects can be short and/or long term. Some of the chemicals found in QMP are carboxylic acid
Carboxylic acid
Carboxylic acids are organic acids characterized by the presence of at least one carboxyl group. The general formula of a carboxylic acid is R-COOH, where R is some monovalent functional group...

s and aromatic compounds. The following compounds have been shown to be important in retinue attraction of workers to their queen (Slessor, 1988) and other effects.
  • (E)-9-oxodec-2-enoic acid (9-ODA) - inhibits queen rearing as well as ovarian development in worker bees; strong sexual attractant for drones when on a nuptial flight; critical to worker recognition of the presence of a queen in the hive
  • (R,E)-(-)-9-hydroxy-2-enoic acid (9-HDA) promotes stability of a swarm, or a "calming" influence
  • (S,E)-(+)-9-HDA
  • Methyl-p-hydroxybenzoate
    Methylparaben
    Methylparaben, also methyl paraben, one of the parabens, is a preservative with the chemical formula CH3. It is the methyl ester of p-hydroxybenzoic acid.-Occurrence:...

     (HOB)
  • 4-hydroxy-3-methoxy phenylethanol (HVA)


Early work on synthetic pheromones was done by Keith N. Slessor, Lori-ann Kaminski, Gaylord G. S. King, John H. Borden, and Mark L. Winston; their work was patented in 1991. Synthetic queen mandibular pheromone (QMP) is a mixture of five components 9-ODA , (-) isomer (9-HDA), (+) isomer of (9-HDA), HOB and HVA in a ratio of 118:50:22:10:1.

Queen retinue pheromone
Queen retinue pheromone
Queen retinue pheromones are a type of honey bee pheromones. The following compounds have also been identified, of which only coniferyl alcohol is found in the mandibular glands. The combination of the 5 QMP compounds and the 4 compounds below is called the Queen Retinue Pheromone...

 (QRP)

The following compounds have also been identified, of which only coniferyl alcohol
Coniferyl alcohol
Coniferyl alcohol is an organic compound. This colourless crystalline solid is a phytochemical, one of the monolignols. It is synthethized via the phenylpropanoid biochemical pathway. When copolymerized with related aromatic compounds, coniferyl alcohol forms lignin or lignans...

 is found in the mandibular glands. The combination of the 5 QMP compounds and the 4 compounds below is called the Queen Retinue Pheromone (QRP). These nine compounds are important for the retinue attraction of worker bees around their queen.
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