The cephalic labial glands are well developed in many bee species. In bumble bee males, they cover most of the head volume, and their secretion is used in marking reproductive territories and attracting virgin queens. In females, however, they are poorly studied. Here, we present chemical analyses of their secretion in queens and workers of Bombus terrestris under various social conditions. The secretion revealed a context-dependent composition with sterile females possessing large amounts of fatty acid dodecyl esters, ranging from dodecyl hexanoate to dodecyl oleate, compared to small amounts in fertile females. Significant reduction in the dodecyl esters also was found in queens at the competition phase, where worker reproduction, aggression, and gyne differentiation occur. The exclusive production of esters by sterile individuals also is typical of Dufour's gland secretion in this species, albeit in this case these are octyl rather than dodecyl esters, and the differences between sterile and fertile individuals are qualitative rather than quantitative. We propose that the labial gland esters provide yet another signal of reproductive inactivity. In virgin queens, it may signal that egg laying is deferred to the next season, while in workers it reinforces the message "I am sterile and out of the reproductive competition". Whether the reduction in dodecyl esters in fertile queens as a function of colony social development is involved in regulating gyne production and the onset of the competition phase is yet to be deciphered.

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