The bumblebee wax moth, Aphomia sociella, is a parasite of bumblebees. In this species, males produce sexual pheromone to attract females, while females produce an aphrodisiac pheromone that initiates male courtship. Both pheromones contain 6,10,14-trimethylpentadecan-2-one (TMPD-one) and the corresponding alcohol, 6,10,14-trimethylpentadecan-2-ol (TMPD-ol) in sex specific quantities. Male sex pheromone consists of 7 components with TMPD-one as a minor one and traces of TMPD-ol. In female aphrodisiac pheromone, TMPD-ol is the major component, while TMPD-one is present in traces. Here we report on the absolute configuration of TMPD-one in male sex pheromone and TMPD-ol in female aphrodisiac pheromone of A. sociella. The configuration was determined from GC/MS of prepared (S)-acetoxypropionyl esters of TMPD-ol. TMPD-one was first reduced to the alcohol that was then derivatized with (S)-acetoxypropionyl chloride. The GC/MS data of obtained diastereoisomers were compared with synthetic standards. The absolute configuration of TMPD-one in the male pheromone was (6R,10R). The configuration of TMPD-ol in the female pheromone was (2R,6R,10R). Electrophysiological experiments showed that TMPD-one and TMPD-ol are perceived by both sexes. The synthetic standards of naturally produced stereoisomers elicited higher responses than mixtures of all stereoisomers.

• MeSH
• můry metabolismus   MeSH
• plynová chromatografie s hmotnostně spektrometrickou detekcí MeSH
• sexuální lákadla chemie   izolace a purifikace   MeSH
• stereoizomerie MeSH
• zvířata MeSH
• Check Tag
• mužské pohlaví MeSH
• ženské pohlaví MeSH
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• sexuální lákadla MeSH

Aphomia sociella (Lepidoptera: Pyralidae: Galleriinae) is a parasitic moth of bumblebees. Behavioral experiments show that A. sociella females emit semiochemicals that influence male pre-mating behavior and serve as a courtship pheromone. GC/EAD and two-dimensional GC/MS (GCxGC-TOFMS) analyses of extracts of females revealed three antennally active compounds. Comparative GC and GCxGC-TOFMS analyses of extracts and synthetic standards confirmed the identity of the antennally active compounds as hexan-1-ol (1), 6,10,14-trimethylpentadecan-2-one (2), and 6,10,14-trimethylpentadecan-2-ol (3). In laboratory bioassays, alcohol 3 and, at higher doses, ketone 2 initiated male courtship behavior associated with ultrasonic production. Hexan-1-ol (1) and ketone 2 enhanced the activity of alcohol 3. These data suggest that hexan-1-ol, 6,10,14-trimethylpentadecan-2-ol, and 6,10,14-trimethylpentadecan-2-one constitute the female-produced courtship pheromone of A. sociella.

• MeSH
• komunikace zvířat MeSH
• Lepidoptera metabolismus   MeSH
• námluvy * MeSH
• sexuální chování zvířat účinky léků   MeSH
• sexuální lákadla metabolismus   farmakologie   MeSH
• těkavé organické sloučeniny metabolismus   farmakologie   MeSH
• včely parazitologie   MeSH
• zvířata MeSH
• Check Tag
• mužské pohlaví MeSH
• ženské pohlaví MeSH
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• sexuální lákadla MeSH
• těkavé organické sloučeniny MeSH