Identification of the Sex Pheromone of the Currant Shoot Borer Lampronia capitella

Abstract

Under an artificial light:dark cycle, females of Lampronia capitella were observed calling, with extended terminal abdominal segments, during the first 2 hr of the photoperiod. Extracts of terminal abdominal segments from females elicited large electroantennographic responses from male antennae. Gas chromatography with electroantennographic detection revealed three active peaks. Based on comparison of retention times and mass spectra of synthetic standards, these compounds were identified as (Z,Z)-9,11-tetradecadienol and the corresponding acetate and aldehyde. The electroantennographic activity of the four geometric isomers of all three compounds was investigated, and the respective (Z,Z)-isomer was found to be the most active in all cases. Aldehydes generally elicited larger antennal responses than alcohols, whereas acetates were the least active compounds. A subtractive trapping assay in the field, based on a 13:26:100 micrograms mixture of (Z,Z)-9,11-tetradecadienal, (Z,Z)-9,11-tetradecadienyl acetate, and (Z,Z)-9,11-tetradecadienol confirmed that all three compounds are pheromone components. Subtraction of (Z,Z)-9,11-tetradecadienol from the blend completely eliminated its attractiveness, whereas the other two-component blends showed reduced activity. This is the first pheromone identification from the monotrysian superfamily Incurvarioidea, confirming that the common pheromones among ditrysian moths (long-chain fatty acid derivatives comprising alcohols, acetates, and aldehydes with one or more double bonds) is not an autapomorphy of Ditrysia, but a synapomorphy of the more advanced heteroneuran lineages.

Key biosynthetic gene subfamily recruited for pheromone production prior to the extensive radiation of Lepidoptera

“…Their pheromones are made of short-chain alcohols and ketones and release through sternal globular glands whose openings are located on the V th abdominal segment [33-35]. The modern distal female abdominal gland and the typical ditrysian calling postures likely arose prior to divergence of the Ditrysia as a few examples are known in some monotrysian Heteroneura [reviewed in [36] and [37]]. However, the exact localization of distal gland producing-pheromone in non-ditrysian Heteroneura remains to be determined.…”

“…1). Recently, long-chain unsaturated pheromone components were identified from the abdominal tip in a moth species outside the Ditrysia; the sex pheromone of the currant shoot borer, Lampronia capitella (Incurvarioidea: Prodoxidae), was characterized as a mixture of ( Z,Z )-9,11-tetradecadienol, and the corresponding acetate and aldehyde [37]. This monotrysian species constitutes the most primitive moth for which long-chain unsaturated pheromone components have been evidenced and provides a unique opening for investigating evolutionary aspects of the ditrysian pheromone mating-signals.…”

Sex pheromone communication of tentiform leaf-miners Phyllonorycter insignitella and Ph. nigrescentella from two related species groups

“…With regards to the time of sexual activities in moths, it is known that a great majority of the females release sex pheromones and copulate during the dark period of a day (see reviews : Dreisig 1986;McNeil 1991). However, some species call during the light period, late in the afternoon (Buda and Karalius 1985;Dreisig 1986;McNeil 1991) or soon after dawn (Dreisig, 1986;McNeil, 1991;Tóth et al, 1995;Svatoš et al, 1999;Lçfstedt et al, 2004;Mozū raitis, 2006). Our data indicate that Ph.…”

Syntheses of conjugated octadecadienoic acids

“…The solvent was removed in vacuo, and the product was purified by kugelrohr distillation to give 2. Preparation of 1-(2′-tetrahydropyranyloxy-)-10-undecyne (13). At 0°C a solution of 2.8 g (3 mL, 33 mmol) 2,3-dihydropyrane in 15 mL dry dichloromethane was added dropwise to a solution of 5.0 g 10-undecyn-1-ol (12) (30 mmol) and 0.75 g pyridinium-4-toluene sulfonate (3 mmol) in 60 mL dry dichloromethane.…”

“…(Z)-1-Bromo-1-heptene (11) (0.71 g, 4 mmol), 76 mg copper(I) iodide (0.4 mmol), 76 mg bis(benzonitrile)-dichloropalladium(II) (PdCl 2 [PhCN] 2 , 0.2 mmol), and 12 mL piperidine were placed in a 25-mL dry flask. To this suspension 2.0 g (8 mmol) 1-(2′-tetrahydropyranyloxy-)-10-undecyne (13) was added at room temperature. After stirring for 2 h, saturated aqueous ammonium chloride solution was added to the suspension, which was extracted three times with diethyl ether.…”