Byers, J.A. and Levi-Zada, A. 2011. Individual variation of (S)-4-methyl-3-heptanone in heads of braconid wasp, Leiophron uniformis, and Pogonomyrmex ants indicates costs of semiochemical production. Chemoecology 21:35-44. pdf

Lygus hesperus male (left) and female on cotton leaf
Abstract-- (S)-4-Methyl-3-heptanone is an alarm pheromone released from the mandibular glands in heads of harvester ants (Pogonomyrmex spp.). We used gas chromatography-mass spectrometry (GC-MS) to study the variation in amounts of this ketone among individual ants of a colony. P. barbatus contained about 2,000 ng per head, while only about half of this amount was found in heads of P. rugosus and P. californicus. Individuals of P. barbatus from three different nests contained rather uniform amounts of the alarm pheromone within each colony (16-30% coefficient of variation CV; normal distributions skewed left), but one nest under food stress had a significantly lower mean amount. In contrast, both sexes of a small braconid wasp Leiophron uniformis, a parasitoid of Lygus plant bugs, contained up to 10 ng of the same volatile enantiomer in their heads; and groups of either sex of the wasp exhibited normal distributions of quantities (64% CV, skewed right). The differences in the distributions between parasitoids and ants suggest that related members within a social ant colony may attempt to maintain a uniform level of ketone compared to independent variation in unrelated, solitary wasp individuals. When the wasp’s leg was grasped with forceps, it tried to escape and bite the forceps as it ejected (S)-4-methyl-3-heptanone (detected by solid phase microextraction, SPME, and GC-MS). Since adult wasps are nonsocial and feed only on nectar, their sharp piercing mandibles in combination with this escape/biting behavior indicate the ketone is used for defense rather than for an alarm function as in harvester ants. Costs of producing the semiochemical in wasp L. uniformis and ants P. barbatus and P. californicus are suggested since populations exhibited a significant linear increase in the amount of (S)-4-methyl-3-heptanone with an increase in body weight of individuals.
Chemical Ecology