Pheromones, of bees

Larvae of certain insects, which feed on Pinaceae, ingest and sequester the lipophilic constituents, e.g., the abietic acid, of these plants and use them to repel predators (E 5.1). Carnosolic acid causes the characteristic bitter taste of Labia-tae. Geranylgeraniol, its acetate, and cembrene A are constituents of the pheromones of bees, ants, and termites, respectively. The andromedotoxins, e.g., acetylandromedol, are toxic compounds widespread in Ericaceae. They increase the constancy in pollination (E 5.5.1). 

Constituents of the pheromones of bees and ants, respectively Trail pheromone of the termite Nasutitermes exitisosis... 

The pheromones of bees have important functions in the organization of the colony. The queen constantly gives off a substance which informs the members of the colony about her presence. This Queen-substance was isolated by Butler, Callow and Johnston . It is a relatively simple substance of the following constitution ... 

Pheromones are commonly called sex attractants, although they have other signaling functions, too. A pheromone of the queen bee is tra s-CH3CO(CH2)5CH=CHCOOH. 

Flowers of some orchids mimic both the appearance and sex pheromone of virgin females of certain species of bees or wasps. This sexual deception results in pollination by male hymenoptera that would not normally visit flowers. Japanese honey bee drones (Apis cerana japonica) cluster on the oriental orchid (Cymbidiumpumilum) while on their mating flights [ 134]. By comparing volatile profiles of orchids and the female hymenoptera they mimic, or by GC-EAD and GC-MS analysis of orchid volatiles, several compounds have been identified that may mediate this attraction for the solitary bee Andrena nigroaenea [135, 136] and the scoliid wasp Campsoscolia ciliata [135]. 

Free JB (1987) Pheromones of social bees. Chapman and Hall, London... 

So far in our discussion, life has been simple in one respect each action of a pheromone has been the consequence of one or two, or a few in the case of the brown algae, molecules in one species. In nature, things can be more complex. One molecule can serve as a pheromone for multiple species benzaldehyde serves as a trail pheromone for bees, Trigona genus a defense pheromone for ants, Veromessor genus and as a male sex pheromone in the moth, Pseudaletia genus. 

Mant, J., Brandli, C., Vereecken, N. J., Schulz, C.M., Francke, W. and Schiestl, F. P. (2005). Cuticular hydrocarbons as sex pheromone of the bee Colletes cunicularius and the key to its mimicry by the sexually deceptive orchid Ophrys exaltata. 

Breed, M.D. (1998a). Recognition pheromones of the honey bee. BioScience, 48, 463-470. 

Smith, B. H., Carlson, R. G. and Frazier, J. (1985). Identification and bioassay of macrocyclic lactone sex pheromone of the halictine bee Lasioglossum zephyrum. 

Step 2b Young larvae mimic the sex pheromone of the female bee Habropoda pallida... 

A typical result is the E.I. mass spectrum for the alarm pheromone of the honey bee. The bees check every insect coming into the hive for strangers. If a strange insect (even a bee from another hive) is detected, an alarm pheromone is released and the intruder is attacked. The pheromone is a simple volatile organic molecule having this mass spectrum. 

This reaction provides a useful way of introducing a double bond next to a carbonyl group. Here it is in a synthesis by Barry Trost of the Queen Bee Substance (the compound fed by the workers to those bee larvae destined to become queens). The compound is also a pheromone of the termite and is used to trap these destructive pests. Trost started with the monoester of a dicarboxylic acid, which he converted to a methyl ketone by reacting the acyl chloride with a cuprate. The ketone was then protected as a dioxolane derivative to prevent it enolizing, and the sulfur was introduced by reacting the enolate of the ester with the sulfur electrophile MeSSMe. 

Docosane is a component of the female sex pheromone of the bee Andrena nigroaenea453 (Z)-13-Docosenal (A187) is part of the trail pheromone of the ant D. thoracicus433 (6Z,9Z)-6,9-Docosadien-ll-ol (A188) is a synergistic sex pheromone component of female 0. detrita451... 

Nonacosane and (Z)-9- (A209), (Z)-ll- (A211), and (Z)-12-nonacosene (A210) are parts of the female sex pheromone of the bee A. nigroaenea 5i The alkene A209 is a contact pheromone of male cerambycid beetle M. 

Within mixtures of natural products, interactions are the norm rather than the exception and Nature seems to have known very well that there can be strength in numbers and that there are not only active compounds but also supportive ancillary constituents. Thus, the response of the mammalian immune system to a stimulus depends on the concerted effect of a host of cytokines and not on the activity of just one, while the mandibular pheromone of the queen honey bee is a mixture of nine compounds, all required to elicit its multiple action on worker bees and drones.54... 

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