Aphrodisiac pheromones from the wings of the Small Cabbage White and Large Cabbage White butterflies, Pieris rapae and Pieris brassicae

S. Yildizhan, J.J.A. van Loon, A. Sramkova, M. Ayasse, C. Arsene, C.J.M. ten Broeke, S. Schulz

Research output: Contribution to journalArticleAcademicpeer-review

42 Citations (Scopus)

Abstract

The small and large cabbage butterflies, Pieris rapae and P. brassicae, are found worldwide and are of considerable economic importance. The composition of the male scent-producing organs present on the wings was investigated. More than 120 components were identified, but only a small portion proved to be male specific. Major components were the known beetle pheromone ferrulactone (1) in P. rapae and its previously unknown larger analogue, brassicalactone (2), in P. brassicae. The latter carries an additional isoprene unit and is closely related to 1. Other components present in larger amounts on male relative to female wings were hexahydrofarnesylacetone (18) and phytol (23). Brassicalactone (2) was fully characterized by synthesis of its various diastereomers by using ring-closing metathesis. A similar approach to ferrulactone (1) failed, presumably because of its smaller ring size. Instead, this compound was synthesized by using a modified literature procedure. The biological activity of the compounds in the extract was tested by coupled gas chromatographic-electroantennographic (GC-EAD) analysis, which showed that both macrolides and the other major components of the wings can be detected by the antennae of the conspecific female butterflies. Other detectable compounds included several alkanes, which are typical constituents of the butterfly cuticula, derivatives of phytol (23) and long-chain secondary alcohols. Finally, bioassays with males showed that the mixture of 1 (P. rapae) or 2 (P. brassicae) together with 18 and 23 applied to freshly eclosed males increased mating success compared to untreated males. Therefore, the two macrolides 1 and 2 are aphrodisiac pheromone components of male small and large cabbage white butterflies, respectively
Original languageEnglish
Pages (from-to)1666-1677
JournalChemBioChem
Volume10
Issue number10
DOIs
Publication statusPublished - 2009

Keywords

  • male sex-pheromone
  • enantioselective total-synthesis
  • 2 macrolide pheromones
  • colias-eurytheme
  • male scent
  • cuticular lipids
  • idea leuconoe
  • lepidoptera
  • esters
  • identification

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