Attractancy of Optically Active Pheromone for Male Gypsy Moths12

Cardé, Ring T.; Doane, Charles C.; Baker, Thomas C.; Iwaki, S.; Marumo, Shingo

doi:10.1093/ee/6.6.768

Cited by 87 publications

(24 citation statements)

References 7 publications

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“…On the basis of electroantennogram and behavioral assays, it is thought that female gypsy moths are producing only the (ϩ)-stereoisomer of disparlure (8). The (-)-stereoisomer can be detected by the male moth but results in an inhibitory response (9,10). In the present study, we were interested in determining how the female moth produces disparlure and in using chiral chromatography to determine its stereoisomeric composition.…”

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confidence: 99%

Sex pheromone biosynthetic pathway for disparlure in the gypsy moth, Lymantria dispar

Jurenka

Subchev

Abad

et al. 2003

Proc. Natl. Acad. Sci. U.S.A.

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The pheromone biosynthetic pathway for production of the sex pheromone disparlure, 2-methyl-7R,8S-epoxy-octadecane, was determined for the gypsy moth. Each step in the pathway was followed by using deuterium-labeled compounds that could be identified by using GC͞MS. This approach provides unequivocal determination of specific reactions in the pathway. It was shown that the alkene precursor, 2-methyl-Z7-octadecene, is most likely made in oenocyte cells associated with abdominal epidermal cells. The pathway begins with valine contributing carbons for chain initiation, including the methyl-branched carbon, followed by chain elongation to 19 carbons. The double bond is introduced with an unusual ⌬12 desaturase that utilizes a methyl-branched substrate. The resulting 18-methyl-Z12-nonadecenoate is decarboxylated to the hydrocarbon, 2-methyl-Z7-octadecene. The alkene is then transported to the pheromone gland through the hemolymph, most probably by lipophorin. At the pheromone gland, the alkene is unloaded and transformed into the epoxide disparlure for release into the environment. A chiral HPLC column was used to demonstrate that the (R,S)-stereoisomer of the epoxide, (؉)-disparlure is found in pheromone glands.

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confidence: 99%

Sex pheromone biosynthetic pathway for disparlure in the gypsy moth, Lymantria dispar

Jurenka

Subchev

Abad

et al. 2003

Proc. Natl. Acad. Sci. U.S.A.

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“…The females release the pheromone, and the males follow the pheromone plume upwind. In the gypsy moth, Lymantria dispar, the main sex pheromone component is (7R,8S)-cis-7,8-epoxy-2-methyloctadecane ((ϩ)-disparlure) 1 (1-3). Interestingly, the antipode, (Ϫ)-disparlure, is a behavioral antagonist in this species (3,4).…”

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Olfaction in the Gypsy Moth, Lymantria dispar

Kowcun

Honson

Plettner

2001

Journal of Biological Chemistry

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The pheromone-binding proteins (PBPs) are 16-kDa abundant proteins in specialized olfactory hairs in insects. The mechanism by which the PBPs remove the pheromone from the inner surface of sensory hairs and deliver it to the sensory cell remains unclear. Existing qualitative models postulate that pheromone is released near the dendrite by a decrease in pH or by a reduced form of the PBP. This study focuses on the two PBPs from the gypsy moth and the enantiomers of the pheromone cis-2-methyl-7,8-epoxyoctadecane. The pH dependence of pheromone binding has revealed three ionizations that are important. The type of ligand influences two of these ionizations. We propose that the (؊)-enantiomer of the pheromone interacts with one of the ionizable residues on the protein while the (؉)-enantiomer does not. Simultaneous variation of pH and KCl concentration in the physiological range or reduction of disulfide bridges does not change the affinity of PBP for pheromone. We propose a revised model of pheromone transport from the inner surface of the sensory hair to the sensory neuron.

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“…The effects of (-)-disparlure were much more apparent on in-flight than pre-flight behavior.Field tests (Vite et al 1976, Miller et al 1977, Carde et al 1977 with 2 different synthetic preparations of disparlure (cis-7,8-epoxy-2-methyloctadecane) enantiomers (Iwaki et al 1974, Morl et at. 1976 proved that: higWy optically pure (+)-disparlure is very attractive to male gypsy moths, Lyman/ria dispar (L.); and when (-) -is combined with (+) -disparlure, trap catches are greatly reduced, i.e., racemic (±)-disparlure caught ca.…”

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Gypsy Moth 1 Responses to Pheromone Enantiomers as Evaluated in a Sustained-Flight Tunnel

Miller

Roelofs

1978

Environmental Entomology

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ABSTRACT( -) -Disparlure reduced: (1) the durations of anemotactic flights of mate gypsy moths, Lyman/ria dispar (L.), in plumes of (+) -disparlure; (2) the rate of moth flight with respect to a moving floor pattern; and (3) the percentage of moths initiating anemotactic flights. The effects of (-)-disparlure were much more apparent on in-flight than pre-flight behavior.Field tests (Vite et al. 1976, Miller et al. 1977, Carde et al. 1977 with 2 different synthetic preparations of disparlure (cis-7,8-epoxy-2-methyloctadecane) enantiomers (Iwaki et al. 1974, Morl et at. 1976 proved that: higWy optically pure (+)-disparlure is very attractive to male gypsy moths, Lyman/ria dispar (L.); and when (-) -is combined with (+) -disparlure, trap catches are greatly reduced, i.e., racemic (±)-disparlure caught ca. 10 times fewer males than did (+) -disparlure.The step(s) in the behavioral sequence of attraction to a trap affected by (-) -disparlure remained unknown.Activation bioassays measuring wingfanning (Yamada et al. 1976) revealed little difference in the activities elicited by (+) -and (±)-disparlure, suggesting that the effect on sexual behavior exerted by the (-) enantiomer must be more apparent at some point after initial stimulation of resting moths.As a means of documenting further the effects of ( -) -disparlure on gypsy moth sexual behavior we have used a sustained-flight tunnel to analyze both the pre-flight and in-flight sexual behavior elicited by (+) -and (-) -disparlure and their mixtures. Materials and MethodsAll experiments were conducted with laboratoryreared male gypsy moths supplied by the USDA Gypsy Moth Methods Development Laboratory, Otis AFB, Mass. Shipped pupae were placed in 40x40x 47-cm screened cages and held at 23°C and ca. 70% RH under a 16:8 LID photoperiod. Emerged males were held at the above conditions and used 2-5 days post-eclosion.Experiments were conducted 3-9 h prior to scotophase in the sustained-flight tunnel previously described by Miller and Roelofs (1978). A wind velocity of 65 cm sec-' was maintained throughout the experiments and temperatures were held between 22°-26°C.The enantiomers of disparlure, synthesized and supplied by Mod et al. (1976) paper placed edgewise to the wind and positioned 18 cm above the canvas belt floor.In trapping tests, baited Pherocon™ Ie traps opened to 11 cm and having both a sticky top and bottom (Miller et al. 1977) were hung one at a time at the upwind end of the flight tunnel at ca. 40 cm above the tunnel floor. In a test of their relative attractancy, traps baited with (+)-and (±)-disparlure were alternated. Release cages containing 5 male gypsy moths were inserted into the chemical plumes and opened allowing responding males to fly to the traps.In choice tests, 2 chemical treatments positioned 10 cm apart were introduced into the flight tunnel at once. Smoke generated from sources soaked with titanium tetrachloride demonstrated that resultant plumes were discrete over the upwind half of the tunnel and contiguous near the downwind end. Moths...

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Attractancy of Optically Active Pheromone for Male Gypsy Moths12

Cited by 87 publications

References 7 publications

Sex pheromone biosynthetic pathway for disparlure in the gypsy moth, Lymantria dispar

Sex pheromone biosynthetic pathway for disparlure in the gypsy moth, Lymantria dispar

Olfaction in the Gypsy Moth, Lymantria dispar

Gypsy Moth 1 Responses to Pheromone Enantiomers as Evaluated in a Sustained-Flight Tunnel

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