Sex pheromone for the brownbanded cockroach is an unusual dialkyl-substituted alpha-pyrone.

Charlton, Ralph E.; Webster, Francis X.; Zhang, Aijun; Schal, Coby; Liang, Dangsheng; Sreng, Isabelle; Roelofs, W. L.

doi:10.1073/pnas.90.21.10202

Cited by 38 publications

(22 citation statements)

References 20 publications

(23 reference statements)

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“…Several highly attractive epoxygermacranoid compounds have been identified from various Periplaneta and Blatta species (family Blattidae), and these compounds, in various blends, also appear to function in reproductive isolation (13)(14)(15)(16)(17). An exceptionally attractive α-pyrone (supellapyrone) was identified from the brown-banded cockroach Supella longipalpa (Blattellidae, Pseudophyllodromiinae), and this pheromone appears to function as a single compound and not as part of a pheromone blend (18)(19)(20). A substituted quinone (blattellaquinone), from the German cockroach Blattella germanica (Blattellidae, Blattellinae) (21), represents another chemical class.…”

Section: Discussionmentioning

confidence: 99%

Unusual macrocyclic lactone sex pheromone of Parcoblatta lata , a primary food source of the endangered red-cockaded woodpecker

Eliyahu

Nojima

Santangelo

et al. 2011

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

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Wood cockroaches in the genus Parcoblatta, comprising 12 species endemic to North America, are highly abundant in southeastern pine forests and represent an important prey of the endangered red-cockaded woodpecker, Picoides borealis. The broad wood cockroach, Parcoblatta lata, is among the largest and most abundant of the wood cockroaches, constituting >50% of the biomass of the woodpecker's diet. Because reproduction in red-cockaded woodpeckers is affected dramatically by seasonal and spatial changes in arthropod availability, monitoring P. lata populations could serve as a useful index of habitat suitability for woodpecker conservation and forest management efforts. Female P. lata emit a volatile, longdistance sex pheromone, which, once identified and synthesized, could be deployed for monitoring cockroach populations. We describe here the identification, synthesis, and confirmation of the chemical structure of this pheromone as (4Z,11Z)-oxacyclotrideca-4,11-dien-2-one [= (3Z,10Z)-dodecadienolide; herein referred to as "parcoblattalactone"]. This macrocyclic lactone is a previously unidentified natural product and a previously unknown pheromonal structure for cockroaches, highlighting the great chemical diversity that characterizes olfactory communication in cockroaches: Each long-range sex pheromone identified to date from different genera belongs to a different chemical class. Parcoblattalactone was biologically active in electrophysiological assays and attracted not only P. lata but also several other Parcoblatta species in pine forests, underscoring its utility in monitoring several endemic wood cockroach species in red-cockaded woodpecker habitats.pheromone monitoring | surveillance | wildlife conservation M any animals-especially nocturnal insects-have evolved sexually dimorphic sex pheromones as an efficient and relatively private communication channel for mate attraction and mate choice (1). Sex pheromones also function in species discrimination, and therefore pheromone blends also play prominent roles in premating reproductive isolation of closely related species and in speciation (1, 2).Most cockroach species are nocturnal, and they profoundly rely on pheromones for intraspecific communication. For example, females of the broad wood cockroach, Parcoblatta lata, a species endemic to pine forests of the southeastern United States, have short wings, are incapable of flight, and therefore have limited dispersal capability. However, by emitting a volatile sex pheromone sexually receptive females are able to recruit males, which are excellent flyers, efficiently (3). Females and nymphs thus are able to remain in the relatively protected habitat beneath the sloughing bark of decaying logs, whereas males incur the greater energetic cost of mate-finding and predation that is associated with greater movement. Our earlier behavioral observations suggested the presence of a female sex pheromone, emitted during a "calling" display, and anatomical and electrophysiological studies confirmed that female-specific ter...

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Section: Discussionmentioning

confidence: 99%

Unusual macrocyclic lactone sex pheromone of Parcoblatta lata , a primary food source of the endangered red-cockaded woodpecker

Eliyahu

Nojima

Santangelo

et al. 2011

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

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“…Some sex pheromone and aphrodisiac components of pygidial and tergal glands may be common to species such as Oxyhaloinae, using seducin compounds (Roth & Dateo, 1966;Sreng, 1990), the "Seducin group", such as Blattinae using Periplanone compounds (Persoons et al, 1990;Takegawa & Takahashi, 1989;Ho et al, 1992) or the "periplanone group". In S. longipalpa and B. germanica, only one compound in each species of female sex pheromone was chemically identified (Charlton et al, 1993;Nojima et al, 2005) and no common substance was found. The unique pheromone compound identified in these two species seems to be special to Blattaria and other insects, in particular, moth species (Arn et al, 1992).…”

Section: Discussionmentioning

confidence: 97%

Cockroach tergal glands producing female sex attractant pheromones and male aphrodisiacs in particular in the subfamily Blaberinae (Blattaria: Blaberidae)

Sréng¹

2006

Eur. J. Entomol.

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Abstract. Two principal pheromones are essential in all cockroach sexual behavioral sequences: the volatile sex attractant pheromone released by one partner for long distance attraction and an aphrodisiac sex pheromone produced exclusively by male tergal glands for female mounting and feeding behavior. In the Blaberinae subfamily, the female produces volatile sex attractant pheromones and the male, aphrodisiacs. A close relationship is known to exist between the release of these pheromonal signals from specific glands and the corresponding behaviors (female calling posture and male wing raising). However, in this cockroach group, no data on the glands secreting sex attractant pheromones and aphrodisiacs have been available until now. In seven species of the Blaberinae subfamily: Blaberus colosseus, B. craniifer, B. discoidalis, Blaptica interior, Byrsotria fumigata, Eublaberus distanti and E. posticus; one species of the Zetoborinae subfamily: Schultesia lampyridiformis; one species of the Epilamprinae subfamily: Epilampra maya and one species of the Panesthiinae subfamily, Panesthia sp., the females possess all pygidial glands on the 10 th tergite and the males have tergal glands situated anteriorly, generally on tergites T1 and T2. These glands are formed of type 3 glandular units with two cells, i.e. glandular and canal cells. The uniform presence of female pygidial glands and male tergal glands explains their relationship with their corresponding sexual behaviors.

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“…Recently, a sex pheromone of the brownbanded cockroach Supella longipalpa (Orthoptera: Blattellidae) has been identified as 5-(2',4'-dimethylheptanyl)-3-methyl-2H-pyran-2-one, supellapyrone; the stereochemistry of this pheromone was not elucidated, but it was demonstrated that the pheromone consists of, at most, two enantiomers (6). Our interest in developing synthetic methodologies for the direct joining of a side chain to pyrones led us to use a Pd-catalyzed coupling technique to elucidate the stereochemistry of supellapyrone.…”

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confidence: 99%

“…Our interest in developing synthetic methodologies for the direct joining of a side chain to pyrones led us to use a Pd-catalyzed coupling technique to elucidate the stereochemistry of supellapyrone. However, the fact that the nonnatural stereoisomers were already known neither to appreciably synergize nor to strongly inhibit male response (6) suggested that the synthetic approach alone would be unlikely to succeed. We now report the application of GC (using achiral and chiral columns), coupled with electroantennographic detection (EAD), to establish that natural supellapyrone has the 2'R,4'R configuration.…”

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“…Purification of the Natural Pheromone. The fourth and fifth abdominal tergites of 200 female cockroaches were dissected and extracted as described (6). The crude extract was purified on a Pasteur pipette filled with silica gel 60 (230-400 mesh ASTM; EM Science) that was washed successively with solutions of ether in hexane (0, 5, 10, 20, 50, and 100%); material was collected in small fractions (1 ml) that were monitored by GC-MS.…”

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confidence: 99%

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Application of chiral gas chromatography with electroantennographic detection to the determination of the stereochemistry of a cockroach sex pheromone.

Leal

Shi

Liang

et al. 1995

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

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The coupling of an electroantennographic detector to a chiral capillary gas chromatographic system provides a highly sensitive technique for the determination of pheromone stereochemistry. Electronic modification of the usual electroantennographic detector enables the detector to respond to the relatively broad peaks produced by chiral gas chromatographic systems. By using this methodology, supellapyrone, a female sex pheromone of the brownbanded cockroach Supella longipalpa (Orthoptera: Blattellidae), is shown to be 5-(2'R,4'R-dimethylheptanyl)-3-methyl-2H-pyran-2-one.Stereochemical discrimination may be considered the ultimate refinement of chemical communication in nature. Its importance, with respect to E-and Z-isomerism, was recognized with the characterization of bombykol more than three decades ago (1), and the significance of RIS discrimination was established several years thereafter (2).Despite the sophistication of contemporary analytical techniques, elucidation of the stereochemistry of a naturally occurring semiochemical remains one of the most difficult tasks in pheromone research (3). Most often, the stereochemistry of pheromones is not in fact analytically determined but is inferred from comparative bioassays conducted with all possible synthetic stereoisomers. This approach is unambiguous when one of the isomers is an antagonist to the natural pheromone. An example of this is provided by the Japanese beetle Popillia japonica whose sex pheromone has been identified as 5-(Z)-(-)-(dec-1-enyl)oxacyclopentan-2-one, the stereochemistry of which could be assigned as R because trap catches were reduced dramatically by the addition of the S-enantiomer (4). However, for a pheromone whose stereoisomers show similar bioactivity, the bioassay gives no information on the stereochemistry of the natural product. As an example, the final clue to the absolute configuration of the German cockroach contact sex pheromone was a classical mixture melting point determination, since all four possible stereoisomers proved to be equally bioactive (5).Recently, a sex pheromone of the brownbanded cockroach Supella longipalpa (Orthoptera: Blattellidae) has been identified as 5-(2',4'-dimethylheptanyl)-3-methyl-2H-pyran-2-one, supellapyrone; the stereochemistry of this pheromone was not elucidated, but it was demonstrated that the pheromone consists of, at most, two enantiomers (6). Our interest in developing synthetic methodologies for the direct joining of a side chain to pyrones led us to use a Pd-catalyzed coupling technique to elucidate the stereochemistry of supellapyrone. However, the fact that the nonnatural stereoisomers were already known neither to appreciably synergize nor to strongly inhibit male response (6) suggested that the synthetic approach alone would be unlikely to succeed. We now report the application of GC (using achiral and chiral columns), coupled with electroantennographic detection (EAD), to establish that natural supellapyrone has the 2'R,4'R configuration.MATERIALS AND METHODS Analytical ...

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Sex pheromone for the brownbanded cockroach is an unusual dialkyl-substituted alpha-pyrone.

Cited by 38 publications

References 20 publications

Unusual macrocyclic lactone sex pheromone of Parcoblatta lata , a primary food source of the endangered red-cockaded woodpecker

Unusual macrocyclic lactone sex pheromone of Parcoblatta lata , a primary food source of the endangered red-cockaded woodpecker

Cockroach tergal glands producing female sex attractant pheromones and male aphrodisiacs in particular in the subfamily Blaberinae (Blattaria: Blaberidae)

Application of chiral gas chromatography with electroantennographic detection to the determination of the stereochemistry of a cockroach sex pheromone.

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