| Title: | "Identification and biosynthesis of novel male specific esters in the wings of the tropical butterfly, Bicyclus martius sanaos" |
| Author(s): | Wang HL; Brattstrom O; Brakefield PM; Francke W; Lofstedt C; |
| Address: | "Department of Biology, Lund University, 223 62, Lund, Sweden, hong-lei.wang@biol.lu.se" |
| DOI: | 10.1007/s10886-014-0452-y |
| ISSN/ISBN: | 1573-1561 (Electronic) 0098-0331 (Print) 0098-0331 (Linking) |
| 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, 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 Delta11-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" |
| Keywords: | "Animals Butterflies/*metabolism Deuterium/metabolism Esters/chemistry/*metabolism Fatty Acid Desaturases/metabolism Fatty Acids, Monounsaturated/metabolism Female Male Molecular Structure Palmitic Acid/metabolism Sex Attractants/chemistry/*metabolism Vola;" |
| Notes: | "MedlineWang, Hong-Lei Brattstrom, Oskar Brakefield, Paul M Francke, Wittko Lofstedt, Christer eng Research Support, Non-U.S. Gov't 2014/06/05 J Chem Ecol. 2014 Jun; 40(6):549-59. doi: 10.1007/s10886-014-0452-y. Epub 2014 Jun 4" |
