Andrena bees

Bergstrom, G., J. Tengo, W. Reith, and W. Francke Multicomponent Mandibular Gland Secretions in Three Species of Andrena Bees. (Hym, Apoidea). Z. Naturforsch. 37 C, 1124-1129 (1982). 

Comparative Analyses of Complex Secretions from Heads of Andrena Bees. 

Francke, W., Reith, W., BergstrOm, G. and TengO, J. (1980) Spiroketals in the mandibular glands of Andrena bees. Naturwissenschaften, 61, 149-50. 

TengO, J. and BergstrOm, G. (1978) Identical isoprenoid esters in the Dufour s gland secretions of North American and European Andrena bees (Hymenoptera Andreni-dae). J. Kansas ent. Soc., 51, 521-6. 

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]. 

One family of these solitary bees consists of smallish wasplike creatures commonly called cuckoo bees. As their name implies, they are parasites that lay their eggs in other bees nests, thereby evading all the responsibilities of parenthood. There are several similar species of cuckoo bees, but those we shall focus on are called Nomada marshamella, and the solitary bees they parasitize are Andrena carantonica. We can designate them parasite and host, respectively. Female host bees nest in the ground, each one digging a main burrow with short lateral tunnels. At the end of each tunnel... 

The arrangement remains puzzling, but the bees easily resolve the problem (or what we see as a problem). When the parasitic bees mate, the male simply sprays some of his F6 on the female. The compound is relatively involatile and so persists on the gravid female as she seeks host nests for her eggs. Perfumed with F6 from her mate, the parasitic female penetrates the host nest and completes her task unchallenged. At least three other species of parasitic Nomada bees gain acceptance by their Andrena hosts in this way. 

Tengo, J. and Bergstrom, G. (1977). Cleptoparasitism and odor mimetism in bees Do Nomada males imitate the odor of Andrena females Science, 196,1117-1119. 

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... 

Bee (Andrena spp., Psithyrus sp., Xylocopa varipuncta) male territory marker, male female attractant (OD-R) spider orchid pheromone mimicry... 

Preparation of a pure sample for bioassay (3). pheromone of the palaearctic bee, Andrena wilkella... 

Male palaearctic bees (Andrena wilkella) in Sweden produce 2,8-dimethyl-l,7-dioxaspiro[5.5]undecane (88, Figure 4.34) as their pheromone. Its (25, 6R,83 )-isomer is pheromonally active, while the opposite enantiomer (2R,6S,8R)-88 is inactive.63 There are six stereoisomers of 2,8-dimethyl-1,7-dioxaspiro[5.5]undecane (88), three as shown in Figure 4.34 and their opposite enantiomers. Due to the oxygen-anomeric effect, (2S,6R,8S)-88 and its opposite enantiomer are the stable isomers. 

The conformation of 17-cp/-deoxysalinomycin (a close relative of the antibiotic) has a definite form in solution but it cannot exist as a head-to-tail hydrogen-bonded structure. The relevance of these deductions to its biological role has been discussed. One of the constituents of the secretion of the bee Andrena wilkella is the bis-spiropyran (7), and this has been synthesized from ethyl (+)-(5 )-3-hydroxybutenoate, obtained from the reduction of ethyl acetoacetate by yeast. ... 

Ethyl-2-methyl-l,6-dioxaspiro[4.5]decane is a pheromone produced by two varieties of bees, Parvespula vulgaris L. and Andrena haemorrhoa F. The 27 , 57 , 77 -isomer (188) has been synthesized using 147, ultimately derived from ethyl L-lactate, to supply the chiral stereocenter at C-2 (Scheme 26) [19]. The second chiral intermediate 185 is derived from (5)-( — )-malic acid. 

This symptom was hrst reported in 1948 on Andrena flavipes which was repelled by a DDT apphcation [16]. Further assessments were those on M. rotundata [23] and B. terrestris [25], which reacted negatively to residues of the three pyrethroids fenvalerate, deltamethrin, and lambda-cyhalothrin. Visits of plants treated with pyrethroids by M. rotundata females were reduced by 50 percent compared to control. Generally, bees approached the flowers but did not touch them, or if they did, the contact was very brief. This repellency lasted more than 1 hour with fenvalerate and more than 3 hours with deltamethrin [23]. 

All- m 5-farnesyl hexanoate (190) was the main component of the female Dufour s gland secretion of eleven Andrena species, while ger-anyl octanoate (191) was the main component of the secretion from two other species. One or another of these two compounds is also the dominant component in the cephalic secretion of male Nomada bees. Apparently, Nomada bees prey only on a single Andrena host species. All-rm 5-famesyl hexanoate (190) is the dominant component... 

Sex pheromones of male bees of the genus Andrena (cf. Table 72)... 

Determining the chemistry of different exudates over a wide range of species, genera, families, and orders provides additional data for the systematist. Mandibular and Dufour s secretions of Andrena are species-specific. Colletid, halictine, and nomiine bees all produce lactones in their Dufour s glands, indicating a common ancestry. 

TengO, J. (1979) Odour-released behaviour in Andrena male bees (Apoidea, Hymenoptera). Zoon, 7, 15-48. 

TengO, J. and BergstrOm, G. (1976a) Comparative analyses of lemon-smelling secretions from heads of Andrena F. (Hymenoptera, Apoidea) bees. Comp. Biochem. Physiol., 55B, 179-88. 

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