1984
DOI: 10.1007/bf00994225
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(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), … Show more

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Cited by 16 publications
(13 citation statements)
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“…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).…”
Section: Lygaeidaementioning
confidence: 71%
“…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).…”
Section: Lygaeidaementioning
confidence: 71%
“…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.…”
Section: Composition Of the Frontal Defensive Secretionmentioning
confidence: 99%
“…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).…”
Section: Discussionmentioning
confidence: 86%