Cargando…
Identification and Biosynthesis of Novel Male Specific Esters in the Wings of the Tropical Butterfly, Bicyclus martius sanaos
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 rele...
Autores principales: | , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Springer US
2014
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4090810/ https://www.ncbi.nlm.nih.gov/pubmed/24894159 http://dx.doi.org/10.1007/s10886-014-0452-y |
_version_ | 1782480695600349184 |
---|---|
author | Wang, Hong-Lei Brattström, Oskar Brakefield, Paul M. Francke, Wittko Löfstedt, Christer |
author_facet | Wang, Hong-Lei Brattström, Oskar Brakefield, Paul M. Francke, Wittko Löfstedt, Christer |
author_sort | Wang, Hong-Lei |
collection | PubMed |
description | 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. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1007/s10886-014-0452-y) contains supplementary material, which is available to authorized users. |
format | Online Article Text |
id | pubmed-4090810 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | Springer US |
record_format | MEDLINE/PubMed |
spelling | pubmed-40908102014-07-10 Identification and Biosynthesis of Novel Male Specific Esters in the Wings of the Tropical Butterfly, Bicyclus martius sanaos Wang, Hong-Lei Brattström, Oskar Brakefield, Paul M. Francke, Wittko Löfstedt, Christer J Chem Ecol Article 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. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1007/s10886-014-0452-y) contains supplementary material, which is available to authorized users. Springer US 2014-06-04 2014 /pmc/articles/PMC4090810/ /pubmed/24894159 http://dx.doi.org/10.1007/s10886-014-0452-y Text en © The Author(s) 2014 https://creativecommons.org/licenses/by/4.0/ Open Access This article is distributed under the terms of the Creative Commons Attribution License which permits any use, distribution, and reproduction in any medium, provided the original author(s) and the source are credited. |
spellingShingle | Article Wang, Hong-Lei Brattström, Oskar Brakefield, Paul M. Francke, Wittko Löfstedt, Christer Identification and Biosynthesis of Novel Male Specific Esters in the Wings of the Tropical Butterfly, Bicyclus martius sanaos |
title | Identification and Biosynthesis of Novel Male Specific Esters in the Wings of the Tropical Butterfly, Bicyclus martius sanaos |
title_full | Identification and Biosynthesis of Novel Male Specific Esters in the Wings of the Tropical Butterfly, Bicyclus martius sanaos |
title_fullStr | Identification and Biosynthesis of Novel Male Specific Esters in the Wings of the Tropical Butterfly, Bicyclus martius sanaos |
title_full_unstemmed | Identification and Biosynthesis of Novel Male Specific Esters in the Wings of the Tropical Butterfly, Bicyclus martius sanaos |
title_short | Identification and Biosynthesis of Novel Male Specific Esters in the Wings of the Tropical Butterfly, Bicyclus martius sanaos |
title_sort | identification and biosynthesis of novel male specific esters in the wings of the tropical butterfly, bicyclus martius sanaos |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4090810/ https://www.ncbi.nlm.nih.gov/pubmed/24894159 http://dx.doi.org/10.1007/s10886-014-0452-y |
work_keys_str_mv | AT wanghonglei identificationandbiosynthesisofnovelmalespecificestersinthewingsofthetropicalbutterflybicyclusmartiussanaos AT brattstromoskar identificationandbiosynthesisofnovelmalespecificestersinthewingsofthetropicalbutterflybicyclusmartiussanaos AT brakefieldpaulm identificationandbiosynthesisofnovelmalespecificestersinthewingsofthetropicalbutterflybicyclusmartiussanaos AT franckewittko identificationandbiosynthesisofnovelmalespecificestersinthewingsofthetropicalbutterflybicyclusmartiussanaos AT lofstedtchrister identificationandbiosynthesisofnovelmalespecificestersinthewingsofthetropicalbutterflybicyclusmartiussanaos |