Maculatic Acids—Sex Attractant Pheromone Components of Bald‐Faced Hornets

Yellowjackets in the genera Vespula and Dolichovespula are prevalent eusocial insects of great ecological and economic significance, but the chemical signals of their sexual communication systems have defied structural elucidation. Herein, we report the identification of sex attractant pheromone com...

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Bibliographic Details
Published in:Angewandte Chemie 2018-09, Vol.130 (36), p.11792-11796
Main Authors: Ren, Weiwu, Gries, Regine, McCaughey, Catherine, Derstine, Nathan, Alamsetti, Santosh K., Kurita, Kenji L., Tu, Lorna, Linington, Roger G., Britton, Robert, Gries, Gerhard
Format: Article
Language:English
Subjects:
Acids
Animal behavior
Antennae
Chemical communication
Chemistry
Communications systems
Electroantennograms
Gas chromatography
Gaschromatographie
High performance liquid chromatography
Insects
Liquid chromatography
Magnetic resonance spectroscopy
Males
Mass spectrometry
Mass spectroscopy
NMR spectroscopy
Organic chemistry
Pheromone
Pheromones
Queens
Sex
Wespen
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Summary:Yellowjackets in the genera Vespula and Dolichovespula are prevalent eusocial insects of great ecological and economic significance, but the chemical signals of their sexual communication systems have defied structural elucidation. Herein, we report the identification of sex attractant pheromone components of virgin bald‐faced hornet queens (Dolichovespula maculata). We analyzed body surface extracts of queens by coupled gas chromatographic–electroantennographic detection (GC‐EAD), isolated the compounds that elicited responses from male antennae by high‐performance liquid chromatography (HPLC), and identified these components by GC mass spectrometry (MS), HPLC‐MS, and NMR spectroscopy. In laboratory olfactometer experiments, synthetic (2Z,7E)‐3,7‐dimethyldeca‐2,7‐diendioic acid (termed here maculatic acid A) and (2Z,7E)‐10‐methoxy‐3,7‐dimethyldeca‐10‐oxo‐deca‐2,7‐dienoic acid (termed here maculatic acid C) in binary combination significantly attracted bald‐faced hornet males. These are the first sex attractant pheromone components identified in yellowjackets. Das macht Wespen scharf: Pheromonkomponenten aus Sexuallockstoffen von Wespen wurden identifiziert. In olfaktometrischen Experimenten wirkte eine Kombination aus synthetischer (2Z,7E)‐3,7‐Dimethyldeca‐2,7‐diendisäure und (2Z,7E)‐10‐Methoxy‐3,7‐dimethyldeca‐10‐oxodeca‐2,7‐diensäure anziehend auf männliche Langkopfwespen.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201804666