Identification of Chemicals Emitted by Calling Males of the Sapote Fruit Fly, Anastrepha serpentina

• Published in: Journal of chemical ecology 2009-05, Vol.35 (5), p.601-609
• Main Authors: Robacker, David C, Aluja, Martin, Bartelt, Robert J, Patt, Joseph
• Format: Article
• Language: English
• Subjects: Agriculture; Anastrepha serpentina; Animal and plant ecology; Animal Communication; Animal, plant and microbial ecology; Animals; Autoecology; Biochemistry; Biological and medical sciences; Biological Microscopy; Biomedical and Life Sciences; chemical composition; Chemical compounds; Chemical ecology; diurnal variation; Ecology; Emissions; Entomology; fruit flies; Fundamental and applied biological sciences. Psychology; Gas Chromatography-Mass Spectrometry; Insects; Life Sciences; Male; males; mating behavior; microextraction; pheromone calling behavior; Protozoa. Invertebrata; pyrazines; Pyrazines - analysis; Pyrazines - chemical synthesis; Pyrazines - chemistry; Pyrazines - isolation & purification; sex attractants; Sex Attractants - analysis; Sex Attractants - chemistry; Sex Attractants - isolation & purification; sex pheromones; Solid Phase Microextraction; synthesis; Tephritidae - physiology
• ISSN: 0098-0331; 1573-1561
• DOI: 10.1007/s10886-009-9631-7

Emissions from sexually active Anastrepha serpentina males were collected by solid-phase microextraction. Calling behavior of wild-type males showed no clear peak during the day, except that it was evident less frequently immediately after daybreak and just before dark. Calling by laboratory males was highest between 8 and 11 h after onset of the photophase, and mating by wild flies occurred mostly between 6 and 10 h after onset of the photophase. Two major components of male emissions were identified as 2,5-dimethylpyrazine (DMP) and 3,6-dihydro-2,5-dimethylpyrazine (DHDMP). DHDMP was synthesized, and the identity of the natural product confirmed by comparison of gas chromatographic retention times and mass spectrum. Emissions of DMP and DHMP were greatest during peak calling behavior, with males emitting up to 1.8 and 3.3 μg/h of DMP and DHDMP, respectively. A minor component, which did not vary with time of day, was identified as 2,3,5-trimethylpyrazine. To our knowledge, this is the first report of 3,6-dihydro-2,5-dimethylpyrazine in nature.