Epoxyalkenyl sex pheromones produced by female moths in highly evolved groups: biosynthesis and its endocrine regulation

Ando, Tetsu; Kawai, Takeshi; Matsuoka, Kanae

doi:10.1584/jpestics.r07-06

Cited by 23 publications

(14 citation statements)

References 19 publications

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“…The odd-numbered chains (C 19 , C 21 , and C 23 ) are expected to be produced by chain elongation of the dietary fatty acids and decarboxylation of acyl intermediates in oenocytes. 5,10) The GC-MS analysis of a pheromone gland extract from the geometrid species, C. c. couaggaria, showed a set of C 21 -C 27 dienyl and trienyl hydrocarbons (Fig. 2), which are known Type II pheromone components and long-chain homologues, 2,3) in addition to saturated compounds considered as cuticle hydrocarbons.…”

Section: Discussionmentioning

confidence: 99%

Female Sex Pheromone ofCystidia couaggaria couaggaria(Lepidoptera: Geometridae): Identification and Field Attraction

Yamakawa

Takubo

Ohbayashi

et al. 2012

Bioscience, Biotechnology, and Biochemistry

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The plum cankerworm moth, Cystidia couaggaria couaggaria (Geometridae: Ennominae), is a defoliator of Chinese plum trees (Prunus mume). The pheromone components of the female were analyzed by gas chromatography (GC) with an electro-antennographic (EAG) detector and GC coupled with mass spectrometry. The crude pheromone extract included several EAG-active components, i.e., trienyl, dienyl, and saturated hydrocarbons, with a C 21 -C 25 straight chain. The characteristic mass spectra indicated the unsaturated hydrocarbons to be (3Z,6Z,9Z)-3,6,9-trienes and (6Z,9Z)-6,9-dienes. In the fields, mixtures of the synthetic C 21 and C 23 trienes in a ratio of 2:3 and 1:4 successfully attracted males of this diurnal species during daytime. While the male antennae responded to the C 25 triene and saturated hydrocarbons, their synergistic effects were not observed on the male attraction in the fields. Addition of the C 21 diene interestingly inhibited the activity of the triene mixture. Males of Cystidia truncangulata, a sympatric diurnal congener of C. c. couaggaria, showed similar EAG responses to the unsaturated hydrocarbons, but no C. truncangulata males were attracted by the lures tested for C. c. couaggaria males, indicating that the identified hydrocarbons comprised the species-specific pheromone of C. c. couaggaria females.Key words: insect pheromone; Type II pheromone; (3Z,6Z,9Z)-3,6,9-triene; geometrid moth; male attractionFemale moths of many species secrete a speciesspecific sex pheromone to communicate with their partners.1-3) This chemical cue plays an important role in attracting males of not only nocturnal species, but also such diurnal species as clearwing moths in the family of Sesiidae 4) and wasp moths in the family of Arctiidae. 5)Geometridae is one of the biggest families in Lepidoptera and also includes some diurnal species, while most geometrid females mate with males in the night-time.The plum cankerworm moth, Cystidia couaggaria couaggaria (Guenée) (Geometridae: Ennominae), is a defoliator of Chinese plum trees (Prunus mume Sieb. et Zucc.) and some other plants in the families of Rosaceae and Celastraceae. This univoltine species inhabits Japan, Korea, and China, and the adults appear in early summer. Adult flight of the moths is usually observed in the daytime, but the ecological aspects have not been thoroughly understood. To establish a monitoring tool for the pest insect of plum trees, the sex pheromone produced by C. c. couaggaria females was chemically analyzed. We identified the pheromone components of C. c. couaggaria females and evaluated the activity of the synthetic pheromone in a field test. We were also interested in the species specificity of the C. c. couaggaria pheromone, because two other Cystidia species, C. truncangulata (Wehrli) and C. stratonice stratonice Stoll, are distributed in Japan. Although it was not known whether the three species were sympatric, we observed the adult flight of C. c. couaggaria and C. truncangulata in the same field in Tottori Prefecture. We analyzed the...

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Section: Discussionmentioning

confidence: 99%

Female Sex Pheromone ofCystidia couaggaria couaggaria(Lepidoptera: Geometridae): Identification and Field Attraction

Yamakawa

Takubo

Ohbayashi

et al. 2012

Bioscience, Biotechnology, and Biochemistry

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“…As shown in Table 1, KRIs of components A and B corresponded well to those of (10E,12Z)hexadeca-10,12-dien-1-al (E10,Z12-16:Ald,) and (10E,12Z)-hexadeca-10,12-dien-1-yl acetate (E10,Z12-16:OAc), respectively, on both HP-5MS and DB-23 columns. KRI of component C was compared with only that of Z3,Z6,Z9-23:HC, because 3,6,9-tricosatrienes as insects pheromones are considered to be biosynthesized from (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid with elongation of the carbon chain (Ando et al 2008). The geometric configuration of component C was confirmed to be 3Z,6Z,9Z-isomer from agreement with the RI.…”

Section: Analyses Of Ead Active Components In the Extracts By Gc-ms Ementioning

confidence: 99%

Hybrid Sex Pheromones of the Hibiscus Flower-bud Borer, Rehimena surusalis

et al. 2015

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The sex pheromone of the hibiscus flower borer Rehimena surusalis (Walker) (Lepidoptera: Crambidae) was analyzed by gas chromatography with electroantennographic detection (GC-EAD) and GC-mass spectrometry (GC/MS). Three EAD-active components were found in crude pheromone gland extracts of calling females. GC/MS and GC analyses using synthetic chemicals and derivatization of the extracts identified three components as (10E,12Z)-hexadeca-10,12-dienal (E10,Z12-16:Ald,), (10E,12E)-hexadeca-10,12-dienyl acetate (E10,Z12-16:OAc), and (3Z,6Z,9Z)-tricosa-3,6,9-triene (Z3,Z6,Z9-23:HC). In field tests, male moths were strongly attracted to a ternary blend of E10,Z12-16:Ald, E10,Z12-16:OAc, and Z3,Z6,Z9-23:HC at a ratio of 1:5:14, but single and binary blends showed only weak or no attraction.

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“…Ando and coworkers unravel unique aspects of type II sex pheromones of the Japanese giant looper: transportation of biosynthesis precursors, biosynthesis pathways, and endocrine regulation by a pheromone biosynthesis-activating neuropeptide. 4) The new findings will hopefully be utilized for pest control in the future.…”

Section: Toward Deeper Understanding Of Bioactive Molecules For Innovmentioning

confidence: 99%

Toward deeper understanding of bioactive molecules for innovative crop protection

Tawata¹,

Ozoe²,

Miyagawa³

2008

J. Pestic. Sci.

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Epoxyalkenyl sex pheromones produced by female moths in highly evolved groups: biosynthesis and its endocrine regulation

Cited by 23 publications

References 19 publications

Female Sex Pheromone ofCystidia couaggaria couaggaria(Lepidoptera: Geometridae): Identification and Field Attraction

Female Sex Pheromone ofCystidia couaggaria couaggaria(Lepidoptera: Geometridae): Identification and Field Attraction

Hybrid Sex Pheromones of the Hibiscus Flower-bud Borer, Rehimena surusalis

Toward deeper understanding of bioactive molecules for innovative crop protection

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