The Evolution of Tyramides in Male Fungus-Growing Ants (Formicidae: Myrmicinae: Attini: Attina).

Ants use a variety of semiochemicals for essential activities and have been a source for many novel natural products. While ant taxa produce a wide variety of chemicals, the chemistry and ecology of male ants have remained understudied. Tyramides are a class of compounds that have been found only in males of the Myrmicinae ant subfamily. Tyramides found in the fire ant Solenopsis invicta are transferred to gynes during mating where they are converted to tyramine, leading to rapid reproductive development. To further understand the evolution of tyramide production in male ants, we determined the tyramide composition in males of 15 fungus-growing ant species (Formicidae: Myrmicinae: Attini: Attina) and a Megalomyrmex species (Formicidae: Myrmicinae: Solenopsidini). Thirteen tyramides were identified, four for the first time in natural sources, and their percent composition was mapped to the fungus-growing ant phylogeny.