Male-released sex pheromone of the stink bug piezodorus hybneri

Walter Soares Leal, Shigefumi Kuwahara, Xiongwei Shi, Hiroya Higuchi, Claudia E.B. Marino, Mikio Ono, Jerrold Meinwald

Research output: Contribution to journalArticlepeer-review

56 Citations (Scopus)

Abstract

Male-released semiochemicals of the stink bug Piezodorus hybneri (Heteroptera: Pentatomidae) elicit attraction of male and female bugs and homosexual behavior in males. Three active components were isolated from the airborne volatiles of males by flash chromatography, with the activity monitored by GC-EAD and behavioral bioassay. The pheromone system was characterized as a mixture of β-sesquiphellandrene, (R)-15-hexadecanolide, and methyl 8-(Z)-hexadecenoate (ratio: 10:4:1), and the activity of the semiochemicals was assessed with authentic samples. Enantiomerically pure samples of the R and S macrolactones were obtained by Yamaguchi's and Mitsunobu's macrolactonization of a key intermediate, (R)-15- hydroxyhexadecanoic acid. The nonnatural S steroisomer was neither a beneficial nor a behavioral antagonist. Individual constituents or binary mixtures were active, but the optimal male response was elicited only by the full mixture. Behavioral observation and the fact that the onset of pheromone production is coincident with ovarian development strongly suggest that these semiochemicals are, in fact, sex pheromones.

Original languageEnglish
Pages (from-to)1817-1829
Number of pages13
JournalJournal of Chemical Ecology
Volume24
Issue number11
DOIs
Publication statusPublished - 1998
Externally publishedYes

Keywords

  • Homosexual behavior, aggregation pheromone, β-sesquiphellandrene, (R)- 15-hexadecanolide, methyl 8-(Z)-hexadecenoate

ASJC Scopus subject areas

  • Ecology, Evolution, Behavior and Systematics
  • Biochemistry

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