(Z,E)-?-farnesene: Major component of secretion from metathoracic scent gland of cotton seed bug,Oxycarenus hyalinipennis (Costa) (Heteroptera; Lygaeidae)

Abstract

The isolation and identification of (Z,E)-α-farnesene[(3Z, 6E)-3,7,11-trimethyldodeca-1,3,6,10-tetraene] (III) as the major component of the secretion from the metathoracic scent gland of the cotton seed bug,Oxycarenus hyalinipennis, is reported. The compound was identified by a combination of [1H] NMR, [(13)C] NMR, UV, and mass spectral data and by comparison with a synthetic sample, prepared by dehydration of (E)-nerolidol. (Z,E)-α-Farnesene (III) has been recorded previously in insects (ants and termites), but this is the first report of its occurrence in a member of the Heteroptera. (E)2-Octenyl acetate (XIII) and 2-octenal (XIV) were identified as minor components of the secretion. In addition, three minor monoterpenoid and two other sesquiterpenoid components were detected and tentatively identified.

Chemical Communication in the True Bugs and Parasitoid Exploitation

“…Secretions of sexually dimorphic metathoracic glands have been analyzed in O. Jasciatus (the large milkweed bug) and Spilostethus rivularis with the outstanding feature of both being an excess of alk-2-enyl and/or alka-2,4-dienyl acetates in secretions of males (Games and Staddon, 1973;Staddon et al, 1985). In another seed bug protected by sequestered toxins, the cotton seed bug (Oxycareninae: Oxycarenus hyalinipennis), synthesis in the metathoracic accessory glands switches from (E)-2-octenyl acetate to mainly (Z,E)-a-farnesene as bugs mature, similar to the situation in Dysdercus intermedius (Section 3.3) (Olagbemiro and Staddon, 1983;Knight et al, 1984a;Staddon, 1986).…”

The ontogeny of soldiers in Prorhinotermes simplex (Isoptera, Rhinotermitidae)

“…Its production in plants is induced by insect feeding (Vuorinen et al, 2004). (Z,E)-a-farnesene has been identified to act as a sexual or trail pheromone in several insect orders, or in the defensive secretion of bugs (Vander Meer et al, 1981;Knight et al, 1984;Detrain et al, 1987;Flath et al, 1993;Yarden et al, 1996). As (Z,E)-a-farnesene is emitted by irritated P. simplex soldiers one may presume that it probably acts as an alarm pheromone.…”

Insecticidal and antifeeding activity of Perilla frutescens‐derived material against the diamondback moth, Plutella xylostella L

“…The configurational isomers (3E,6E)-and (3Z,6E)-α-farnesene have been identified from a number of plants and from the oils of Perilla and Achillea ptarmica (Hern & Dorn 1999;Kuropka et al 1991;Sakai & Hirose 1969;Witzgall et al 1999). The isomer α-farnesene was also identified in several glands from a number of insects such as Pheidole pallidula, Manica rubida and Oxycarenus hyalinipennis and in the pheromones of Ceratitis capitata and Anastrepha suspensa (Detrain et al 1987;Flath et al 1993;Jackson et al 1990;Knight et al 1984;Nigg et al 1994). The isomer α-farnesene was also identified in several glands from a number of insects such as Pheidole pallidula, Manica rubida and Oxycarenus hyalinipennis and in the pheromones of Ceratitis capitata and Anastrepha suspensa (Detrain et al 1987;Flath et al 1993;Jackson et al 1990;Knight et al 1984;Nigg et al 1994).…”