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Identification, synthesis and activity of sex pheromone gland components of the autumn gum moth (Lepidoptera : Geometridae), a defoliator of Eucalyptus

Steinbauer, MJ; Östrand, Fredrik LU ; Bellas, TE; Nilsson, A; Andersson, F; Hedenström, E; Lacey, MJ and Schiestl, FP (2004) In Chemoecology 14(3-4). p.217-223
Abstract
The autumn gum moth, Mnesampela privata (Guenee) (Lepidoptera: Geometridae), is native to Australia and can be a pest of plantation eucalypts. Field-collected and laboratory-reared female autumn gum moths were dissected to remove glands likely to contain components of the sex pheromone. Using gas chromatography (GC) and combined gas chromatography-mass spectrometry (GC-MS), three compounds were identified from female extracts, namely (3Z,6Z,9Z)-3,6,9-nonadecatriene, 1-hexadecanol and 1-octadecanol (confirmed by comparison with synthetic samples). Nonadecatriene elicited an antennal response in male autumn gum moth during gas chromatographic analyses combined with electroantennographic detection (GC-EAD). In electroantennogram (EAG)... (More)
The autumn gum moth, Mnesampela privata (Guenee) (Lepidoptera: Geometridae), is native to Australia and can be a pest of plantation eucalypts. Field-collected and laboratory-reared female autumn gum moths were dissected to remove glands likely to contain components of the sex pheromone. Using gas chromatography (GC) and combined gas chromatography-mass spectrometry (GC-MS), three compounds were identified from female extracts, namely (3Z,6Z,9Z)-3,6,9-nonadecatriene, 1-hexadecanol and 1-octadecanol (confirmed by comparison with synthetic samples). Nonadecatriene elicited an antennal response in male autumn gum moth during gas chromatographic analyses combined with electroantennographic detection (GC-EAD). In electroantennogram (EAG) recording male M. privata antennae responded to the nonadecatriene. Nonadecatriene was synthesised via Kolbe electrolysis, starting with (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid (linolenic acid) and propanoic acid or via an alternative four-step method also starting from linolenic acid. In field trials (3Z,6Z,9Z)-3,6,9-nonadecatriene proved attractive to male moths. Thus, we conclude that (3Z,6Z,9Z)-3,6,9-nonadecatriene is a sex pheromone component of autumn gum moth. This component has been identified in extracts from other geometrids in the same subfamily, Ennominae. However, to our knowledge this is the first example where (3Z,6Z,9Z)-3,6,9-nonadecatriene has been found in females and also proved attractive to male moths when presented on its own. Our results are discussed in relation to other geometrid pheromones. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Chemoecology
volume
14
issue
3-4
pages
217 - 223
publisher
Birkhaüser
external identifiers
  • wos:000224526000011
  • scopus:6344241062
ISSN
1423-0445
DOI
10.1007/s00049-004-0281-5
language
English
LU publication?
yes
id
78e76b9b-1692-4db1-84e3-f0ce726d5c77 (old id 135811)
date added to LUP
2007-06-27 12:39:06
date last changed
2017-01-01 04:19:48
@article{78e76b9b-1692-4db1-84e3-f0ce726d5c77,
  abstract     = {The autumn gum moth, Mnesampela privata (Guenee) (Lepidoptera: Geometridae), is native to Australia and can be a pest of plantation eucalypts. Field-collected and laboratory-reared female autumn gum moths were dissected to remove glands likely to contain components of the sex pheromone. Using gas chromatography (GC) and combined gas chromatography-mass spectrometry (GC-MS), three compounds were identified from female extracts, namely (3Z,6Z,9Z)-3,6,9-nonadecatriene, 1-hexadecanol and 1-octadecanol (confirmed by comparison with synthetic samples). Nonadecatriene elicited an antennal response in male autumn gum moth during gas chromatographic analyses combined with electroantennographic detection (GC-EAD). In electroantennogram (EAG) recording male M. privata antennae responded to the nonadecatriene. Nonadecatriene was synthesised via Kolbe electrolysis, starting with (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid (linolenic acid) and propanoic acid or via an alternative four-step method also starting from linolenic acid. In field trials (3Z,6Z,9Z)-3,6,9-nonadecatriene proved attractive to male moths. Thus, we conclude that (3Z,6Z,9Z)-3,6,9-nonadecatriene is a sex pheromone component of autumn gum moth. This component has been identified in extracts from other geometrids in the same subfamily, Ennominae. However, to our knowledge this is the first example where (3Z,6Z,9Z)-3,6,9-nonadecatriene has been found in females and also proved attractive to male moths when presented on its own. Our results are discussed in relation to other geometrid pheromones.},
  author       = {Steinbauer, MJ and Östrand, Fredrik and Bellas, TE and Nilsson, A and Andersson, F and Hedenström, E and Lacey, MJ and Schiestl, FP},
  issn         = {1423-0445},
  language     = {eng},
  number       = {3-4},
  pages        = {217--223},
  publisher    = {Birkhaüser},
  series       = {Chemoecology},
  title        = {Identification, synthesis and activity of sex pheromone gland components of the autumn gum moth (Lepidoptera : Geometridae), a defoliator of Eucalyptus},
  url          = {http://dx.doi.org/10.1007/s00049-004-0281-5},
  volume       = {14},
  year         = {2004},
}