Synthesis of brevicomin, principal sex attractant in the frass of the female western pine beetle

Bellas, Thomas; Brownlee, Robert G.; Silverstein, Robert M.

doi:10.1016/0040-4020(69)80035-9

Cited by 54 publications

(7 citation statements)

References 4 publications

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“…While it has not been shown previously that frass from Drosophila contains behaviorally relevant chemical stimuli, this has been demonstrated repeatedly for other insect orders, including Coleoptera and Blattodea (Symonds and Gitau-Clarke 2016 ; Wada-Katsumata et al 2015 ). In research with other insects, frass has also been shown to provide a substrate that can be used to identify novel pheromone components from several agricultural and economic pests, such as the boll weevil and the many destructive species of pine beetle (Bellas et al 1969 ; Hall et al 2002 ; Symonds and Gitau-Clarke 2016 ; Tumlinson et al 1969 ).…”

Section: Discussionmentioning

confidence: 99%

Adult Frass Provides a Pheromone Signature for Drosophila Feeding and Aggregation

et al. 2016

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Adult Drosophila melanogaster locate food resources by using distinct olfactory cues that often are associated with the fermentation of fruit. However, in addition to being an odorous food source and providing a possible site for oviposition, fermenting fruit also provides a physical substrate upon which flies can attract and court a potential mate. In this study, we demonstrate that Drosophila adults are able to recruit additional flies to a food source by covering the exposed surface area with fecal spots, and that this recruitment is mediated via olfactory receptors (Ors). Analyses of the deposited frass material demonstrates that frass contains several previously studied pheromone components, such as methyl laurate (ML), methyl myristate (MM), methyl palmitate (MP), and 11-cis-vaccenyl acetate (cVA), in addition to several cuticular hydrocarbons (CHCs) that are known to be behaviorally active. Moreover, this study also demonstrates that adult feeding is increased in the presence of frass, although it appears that Ors are less likely to mediate this phenomenon. In summary, the frass deposited by the fly onto the fruit provides both pheromone and CHC cues that lead to increased feeding and aggregation in Drosophila. This research is the first step in examining Drosophila frass as an important chemical signature that provides information about both the sex and the species of the fly that generated the fecal spots.Electronic supplementary materialThe online version of this article (doi:10.1007/s10886-016-0737-4) contains supplementary material, which is available to authorized users.

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Section: Discussionmentioning

confidence: 99%

Adult Frass Provides a Pheromone Signature for Drosophila Feeding and Aggregation

et al. 2016

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“…Conversion of 6-(Z)-nonen-2-one to exo-brevicomin likely involves a cytochrome P450-mediated formation of a ketoepoxide intermediate that is subsequently cyclized either enzymatically or possibly without an enzyme catalyst ( Fig. 7) (Belles et al, 1969).…”

Section: Exo-brevicominmentioning

confidence: 99%

Pheromone production in bark beetles

Blomquist

Figueroa-Teran

et al. 2010

Insect Biochemistry and Molecular Biology

263

237

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“…The bicyc1ic ketals, frontalin (195) (130), exo-brevicomin (150), endobrevicomin (151) (62,117), and multistriatin (303), all shown in Chart 1, 8* p. 8, have been identified from various bark beetles and appear to be of major importance in their pheromonal blends. No one has commented in any detail on the biosynthetic origin of these compounds.…”

Section: E Biosynthesis Of the Bicyclic Ketalsmentioning

confidence: 96%

Insect Pheromones: A Critical Review of Recent Advances in Their Chemistry, Biology, and Application

Brand

Young²,

Silverstein

1979

Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

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Synthesis of brevicomin, principal sex attractant in the frass of the female western pine beetle

Cited by 54 publications

References 4 publications

Adult Frass Provides a Pheromone Signature for Drosophila Feeding and Aggregation

Adult Frass Provides a Pheromone Signature for Drosophila Feeding and Aggregation

Pheromone production in bark beetles

Insect Pheromones: A Critical Review of Recent Advances in Their Chemistry, Biology, and Application

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