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Why not be a queen? Regioselectivity in mandibular secretions of honeybee castes

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Both female castes of the honeybee (Apis mellifera L.) synthesize hydroxylated 2(E)-decenoic acids in their mandibular glands. Queens produce 9-hydroxy-2(E)-decenoic acid as part of their primer pheromone, while workers produce the regioisomeric 10-hydroxy acid, probably as a larval food source and an antiseptic secretion. Both workers and queens are biosynthetically competent to produce the other caste's dominant hydroxylated compound, as both isomers can be detected in queens and workers. We investigated the source of the caste-determined regioselectivity of hydroxy acid biosynthesis by investigating the production and interconversion of these compounds in isolated worker honeybee mandibular glands with specifically deuterated precursors. Gas chromatographic-mass spectroscopic identification of the labeled product indicates that octadecanoic acid is converted into 10-hydroxy-2(E)-decenoic acid with higher efficiency than either hexadecanoic or decanoic acids. 10-Hydroxydecanoic acid is readily converted into 10-hydroxy-2(E)-decenoic acid as expected in the β-oxidation process. The saturated and unsaturated 10-hydroxy acids are oxidized to the corresponding ten carbon diacids.

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Plettner, E., Sutherland, G.R.J., Slessor, K.N. et al. Why not be a queen? Regioselectivity in mandibular secretions of honeybee castes. J Chem Ecol 21, 1017–1029 (1995).

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