title: Biological activity of the enantiomers of 3-methylhentriacontane, a queen pheromone of the ant Lasius niger.
abstract: Queen pheromones are essential for regulation of the reproductive division of labor in eusocial insect species. Although only the queen is able to lay fertilized eggs and produce females, in some cases workers may develop their ovaries and lay male-destined eggs, thus reducing the overall colony efficiency. As long as the queen is healthy, it is usually in the workers' collective interest to work for the colony and remain sterile. Queens signal their fertility via pheromones, which may have a primer effect, affecting the physiology of workers, or a releaser effect, influencing worker behavior. The queen pheromone of the ant Lasius niger was among the first queen pheromones of social insects to be identified. Its major component is 3-methylhentriacontane (3-MeC31), which is present in relatively large amounts on the queen's cuticle and on her eggs. 3-MeC31 regulates worker reproduction by inhibiting ovarian development. Most monomethyl-branched hydrocarbons can exist in two stereoisomeric forms. The correct stereochemistry is fundamental to the activity of most bioactive molecules, but this has rarely been investigated for methyl-branched hydrocarbons. Here, we tested the bioactivity of the (S)- and (R)-enantiomers of 3-MeC31, and found that whereas both enantiomers were effective in suppressing worker ovarian development, (S)-3-MeC31 appeared to be more effective at suppressing aggressive behavior by workers. This suggests that the natural pheromone may be a mixture of the two enantiomers. The enantiomeric ratio produced by queens remains unknown because of the small amounts of the compound available from each queen.
authors.affiliation: Laboratory of Experimental and Comparative Ethology, University Paris 13, Sorbonne Paris Cité, Villetaneuse 93430, France.
authors.forename: Marine
authors.initials: M
authors.lastname: Motais de Narbonne
authors.affiliation: Laboratory of Socioecology and Social Evolution, Department of Biology, KU Leuven, Naamsestraat 59 - Box 2466, Leuven 3000, Belgium.
authors.forename: Jelle S
authors.initials: JS
authors.lastname: van Zweden
authors.affiliation: Departments of Entomology and Chemistry, University of California, 900 University Avenue, Riverside, CA 92521, USA.
authors.forename: Jan E
authors.initials: JE
authors.lastname: Bello
authors.affiliation: Laboratory of Socioecology and Social Evolution, Department of Biology, KU Leuven, Naamsestraat 59 - Box 2466, Leuven 3000, Belgium.
authors.forename: Tom
authors.initials: T
authors.lastname: Wenseleers
authors.affiliation: Departments of Entomology and Chemistry, University of California, 900 University Avenue, Riverside, CA 92521, USA.
authors.forename: Jocelyn G
authors.initials: JG
authors.lastname: Millar
authors.affiliation: Laboratory of Experimental and Comparative Ethology, University Paris 13, Sorbonne Paris Cité, Villetaneuse 93430, France dettorre@leec.univ-paris13.fr.
authors.forename: Patrizia
authors.initials: P
authors.lastname: d'Ettorre
mesh_terms: D000374:Aggression / Q000187:drug effects; D000473:Alkanes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000818:Animals; D001000:Ants / Q000502:physiology*; D001681:Biological Assay; D005260:Female; D006838:Hydrocarbons / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D010053:Ovary / Q000187:drug effects / Q000254:growth & development; D010675:Pheromones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D012930:Social Dominance; D013237:Stereoisomerism
chemical_list: C000621794:3-methylhentriacontane; D000473:Alkanes; D006838:Hydrocarbons; D010675:Pheromones
keywords: Chirality; Cuticular hydrocarbons; Social insects; Worker reproduction