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Identification and biosynthesis of novel male specific esters in the wings of the tropical butterfly, Bicyclus martius sanaos

Wang, Hong-Lei LU ; Brattström, Oskar; Brakefield, Paul M; Francke, Wittko and Löfstedt, Christer LU (2014) In Journal of Chemical Ecology 40(6). p.549-559
Abstract
Representatives of the highly speciose tropical butterfly genus Bicyclus (Lepidoptera: Nymphalidae) are characterized by morphological differences in the male androconia, a set of scales and hair pencils located on the surface of the wings. These androconia are assumed to be associated with the release of courtship pheromones. In the present study, we report the identification and biosynthetic pathways of several novel esters from the wings of male B. martius sanaos. We found that the volatile compounds in this male butterfly were similar to female-produced moth sex pheromones. Components associated with the male wing androconial areas were identified as ethyl, isobutyl and 2-phenylethyl hexadecanoates and (11Z)-11-hexadecenoates,... (More)
Representatives of the highly speciose tropical butterfly genus Bicyclus (Lepidoptera: Nymphalidae) are characterized by morphological differences in the male androconia, a set of scales and hair pencils located on the surface of the wings. These androconia are assumed to be associated with the release of courtship pheromones. In the present study, we report the identification and biosynthetic pathways of several novel esters from the wings of male B. martius sanaos. We found that the volatile compounds in this male butterfly were similar to female-produced moth sex pheromones. Components associated with the male wing androconial areas were identified as ethyl, isobutyl and 2-phenylethyl hexadecanoates and (11Z)-11-hexadecenoates, among which the latter are novel natural products. By topical application of deuterium-labelled fatty acid and amino acid precursors, we found these pheromone candidates to be produced in patches located on the forewings of the males. Deuterium labels from hexadecanoic acid were incorporated into (11Z)-11-hexadecenoic acid, providing experimental evidence of a Δ11-desaturase being active in butterflies. This unusual desaturase was found previously to be involved in the biosynthesis of female-produced sex pheromones of moths. In the male butterflies, both hexadecanoic acid and (11Z)-11-hexadecenoic acid were then enzymatically esterified to form the ethyl, isobutyl and 2-phenylethyl esters, incorporating ethanol, isobutanol, and 2-phenylethanol, derived from the corresponding amino acids L-alanine, L-valine, and L-phenylalanine. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Chemical Ecology
volume
40
issue
6
pages
549 - 559
publisher
Springer
external identifiers
  • pmid:24894159
  • wos:000339347300008
  • scopus:84904210938
ISSN
1573-1561
DOI
10.1007/s10886-014-0452-y
project
Evolutionary mechanisms of pheromone divergence in Lepidoptera
language
English
LU publication?
yes
id
debdfcaa-3867-4c60-a4e3-993cb739bc81 (old id 4529316)
date added to LUP
2014-07-09 07:53:25
date last changed
2017-10-22 03:03:27
@article{debdfcaa-3867-4c60-a4e3-993cb739bc81,
  abstract     = {Representatives of the highly speciose tropical butterfly genus <i>Bicyclus</i> (Lepidoptera: Nymphalidae) are characterized by morphological differences in the male androconia, a set of scales and hair pencils located on the surface of the wings. These androconia are assumed to be associated with the release of courtship pheromones. In the present study, we report the identification and biosynthetic pathways of several novel esters from the wings of male B. martius sanaos. We found that the volatile compounds in this male butterfly were similar to female-produced moth sex pheromones. Components associated with the male wing androconial areas were identified as ethyl, isobutyl and 2-phenylethyl hexadecanoates and (11Z)-11-hexadecenoates, among which the latter are novel natural products. By topical application of deuterium-labelled fatty acid and amino acid precursors, we found these pheromone candidates to be produced in patches located on the forewings of the males. Deuterium labels from hexadecanoic acid were incorporated into (11Z)-11-hexadecenoic acid, providing experimental evidence of a Δ11-desaturase being active in butterflies. This unusual desaturase was found previously to be involved in the biosynthesis of female-produced sex pheromones of moths. In the male butterflies, both hexadecanoic acid and (11Z)-11-hexadecenoic acid were then enzymatically esterified to form the ethyl, isobutyl and 2-phenylethyl esters, incorporating ethanol, isobutanol, and 2-phenylethanol, derived from the corresponding amino acids L-alanine, L-valine, and L-phenylalanine.},
  author       = {Wang, Hong-Lei and Brattström, Oskar and Brakefield, Paul M and Francke, Wittko and Löfstedt, Christer},
  issn         = {1573-1561},
  language     = {eng},
  number       = {6},
  pages        = {549--559},
  publisher    = {Springer},
  series       = {Journal of Chemical Ecology},
  title        = {Identification and biosynthesis of novel male specific esters in the wings of the tropical butterfly, <i>Bicyclus martius sanaos</i>},
  url          = {http://dx.doi.org/10.1007/s10886-014-0452-y},
  volume       = {40},
  year         = {2014},
}