Sex Attractant Pheromone of the House Fly: Isolation, Identification and Synthesis

Carlson, David A.; Mayer, M. S.; Silhacek, Donald L.; James, Justin; Beroza, Morton; Bierl, B. A.

doi:10.1126/science.174.4004.76

Cited by 298 publications

(122 citation statements)

References 8 publications

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“…17 One of the best-known examples of these naturally produced bioactive hydrocarbons is (Z)-tricos-9-ene which was described as a pheromone in dozens of species including the house fly (Musca domestica), acting in this case as a sex attractant. 18 On the other hand, there are only a few examples of natural occurrence of (Z)-tricos-11-ene (1) with only one example related to chemical communication. In this case, compound 1 was detected in a complex mixture of cuticular hydrocarbons which acts has a pheromone in Drosophila birchii.…”

Section: Resultsmentioning

confidence: 99%

Identification and Synthesis of the Male-Produced Sex Pheromone of the Soldier BeetleChauliognathus fallax(Coleoptera: Cantharidae)

Vidal

Fávaro

Guimarães

et al. 2016

Journal of the Brazilian Chemical Society

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Section: Resultsmentioning

confidence: 99%

Identification and Synthesis of the Male-Produced Sex Pheromone of the Soldier BeetleChauliognathus fallax(Coleoptera: Cantharidae)

Vidal

Fávaro

Guimarães

et al. 2016

Journal of the Brazilian Chemical Society

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“…(Z )-9-tricosene has also been identified as a sex pheromone released by the female housefly Musca domestica (Carlson et al 1971), which is a prey species of P. beijingensis. Later, some other compounds such as (Z)-9,10-epoxytricosane, (Z )-14-tricosene-10-one and some methyl alkanes were found to enhance the male housefly's sexual activity in combination with (Z)-9-tricosene (Uebel et al 1976;Rogoff et al 1980).…”

Section: Discussionmentioning

confidence: 99%

Male-specific ( Z )-9-tricosene stimulates female mating behaviour in the spider Pholcus beijingensis

Xiao

Zhang

2010

Proc. R. Soc. B.

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Chemical signals play an important role in spider sexual communication, yet the chemistry of spider sex pheromones remains poorly understood. Chemical identification of male-produced pheromonemediating sexual behaviour in spiders has also, to our knowledge, not been reported before. This study aimed to examine whether chemically mediated strategies are used by males of the spider Pholcus beijingensis for increasing the probability of copulation. Based on data from gas chromatography-mass spectrometry analysis, electroantennography assay and a series of behavioural tests, we verified that (Z)-9-tricosene is a male-specific compound in the spider P. beijingensis. This compound acts as an aphrodisiac: it increases the likelihood that a female will mate. Mate-searching males release (Z )-9-tricosene to stimulate sexual behaviour of conspecific females. In the two-choice assay, however, sexually receptive females show no preference to the chambers containing (Z )-9-tricosene. This indicates that the male pheromone of P. beijingensis is not an attractant per se to the conspecific females. This is, to our knowledge, the first identification of a male-produced aphrodisiac pheromone in spiders.

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“…The (Z)-9-tricosene and tricosane have been reported as sex-attractant pheromones of a butterfly, Idea leuconoe, 5 and a housefly, Musca domestica. 6 We mention several advantages of this method. First, it did not cause any chemical or physical damage to the firefly.…”

Section: Resultsmentioning

confidence: 99%

Analysis of Sex-Attractant Pheromones of Firefly Pyrocoelia oshimana by Gas Chromatography Mass Spectrometry

Shibue

Goto²,

Shibue

et al. 2000

ANAL. SCI.

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The difficulties to analyze an insect pheromone have been well known, and various analytical methods have been reported. 1,2 One can point out some difficulties concerning the analysis of insect pheromones. The amounts of the compounds are very small, and many homogenized species are required to collect the pheromones. Also, many preparation procedures are needed to reduce the lipid components. For rare insect species, abundant measurements would be required. Here, we propose an alternative method to collect the sex-attractant pheromone from just one firefly, without causing any physical damage to it.Ohba has already successfully obtained the sex-attractant pheromones of the firefly Genus Pyrocoelia Gorham, using organic solvent extraction, and has confirmed their biological activities. 3,4 The purpose of the present study is to detect sexattractant pheromones by gas chromatography mass spectrometry (GC/MS), and to characterize their chemical properties. We report on the first detection of sex-attractant pheromones of firefly Pyrocoelia oshimana NAKANE, by gas chromatography mass spectrometry. ExperimentalFireflies Pyrocoelia oshimana NAKANE were collected from a field site on Hakedake, Tokunoshima Island, Kagoshima prefecture. We put one female firefly in a clean glass bial, which had been washed using hexane, and dried at 200˚C in an electric oven. We did not observe any chemical background Ogawacho, Kodaira, Japan *2 Kanagawa Prefectural Daishi Highschool, Yotsuyashimocyo, Kawasaki, Japan *3 Materials Characterization Central Laboratory, Waseda University, Okubo, Shinjuku, Japan *4 Yokosuka City Museum, 95, Fukatadai, Yokosuka, Japan

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Sex Attractant Pheromone of the House Fly: Isolation, Identification and Synthesis

Abstract: A sex pheromone isolated from the cuticle and feces of the female house fly attracts the male fly; it has been identified as ( Z )-9-tricosene. Chemical and biological comparisons of the natural and synthesized compounds show that they are identical.

Cited by 298 publications

References 8 publications

Identification and Synthesis of the Male-Produced Sex Pheromone of the Soldier BeetleChauliognathus fallax(Coleoptera: Cantharidae)

Identification and Synthesis of the Male-Produced Sex Pheromone of the Soldier BeetleChauliognathus fallax(Coleoptera: Cantharidae)

Male-specific ( Z )-9-tricosene stimulates female mating behaviour in the spider Pholcus beijingensis

Analysis of Sex-Attractant Pheromones of Firefly Pyrocoelia oshimana by Gas Chromatography Mass Spectrometry

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