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Investigation of the contents of the scent glands of the heliconiine butterfly Heliconius erato phyllisvia gas chromatography/electroantennography revealed an unprecedented active compound. The males transfer this compound to females during mating. The structure of (2R,6E,10R)-2,6-dimethyl-6-undecen-10-olide, a derivative of geranylacetone, was proposed on the basis of infrared and mass spectrometry spectra and microderivatization and confirmed by racemic and stereoselective syntheses. Bioassays with the synthetic macrolide showed the repellency of this compound, termed phyllisolide, when applied to scent glands of females, identifying it as an anti-aphrodisiac pheromone.

Wheel bugs (Heteroptera: Reduviidae: Harpactorinae: Arilus) are general predators, the females of which have reddish-orange subrectal glands (SGs) that are eversible like the osmeteria in some caterpillars. The rancid odor of Arilus and other reduviids actually comes from Brindley's glands, which in the North (A. cristatus) and South (A. carinatus) American wheel bugs studied emit similar blends of 2-methylpropanoic, butanoic, 3-methylbutanoic, and 2-methylbutanoic acids. The Arilus SG secretions studied here are absolutely species specific. The volatile SG components of A. carinatus include (E)-2-octenal, (E)-2-nonenal, (E)-2-decenal, (E,E)-2,4-nonadienal, (E)-2-undecenal, hexanoic acid, 4-oxo-nonanal, (E,E)-2,4-decadienal, (E,Z)-2,4- or (Z,E)-2,4-decadienal, and 4-oxo-(E)-2-nonenal; whereas in A. cristatus the SG secretion contains β-pinene, limonene, terpinolene, terpinen-4-ol, thymol methyl ether, α-terpineol, bornyl acetate, methyl eugenol, β-caryophyllene, caryophyllene oxide, and farnesol. Arilus spp. SG secretions may be sex pheromones, but verification of this hypothesis requires further testing.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

For Abstract see ChemInform Abstract in Full Text.

For Abstract see ChemInform Abstract in Full Text.

For Abstract see ChemInform Abstract in Full Text.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.