Literature DB >> 23007309

Does the stereochemistry of methylated cuticular hydrocarbons contribute to mate recognition in the egg parasitoid wasp Ooencyrtus kuvanae?

Kelly Ablard1, Regine Gries, Grigori Khaskin, Paul W Schaefer, Gerhard Gries.   

Abstract

Close-range sexual communication of the egg parasitoid wasp Ooencyrtus kuvanae (Hymenoptera: Encyrtidae) takes place on host gypsy moth, Lymantria dispar (Lepidoptera: Lymantriidae), egg masses. We tested the hypothesis that mate recognition in O. kuvanae is mediated, in part, by low-volatility cuticular hydrocarbon (CHC) pheromone components. Gas chromatographic and GC-mass spectrometric analyses of body surface extracts of male and female wasps revealed no sex-specific components, but 5-methylheptacosane (5-me-27Hy) and 5,17-dimethylheptacosane (5,17-dime-27Hy) were consistently more abundant in extracts of males. The ratio of 5-me-27Hy and 5,17-dime-27Hy was similar in extracts of males and females, and quantitative differences alone seemed insufficient to impart sex-specific CHC profiles. Therefore, we further hypothesized that the absolute configuration of 5-me-27Hy and 5,17-dime-27Hy contributes to mate recognition or attraction. As the stereoisomers of 5-me-27Hy and 5,17-dime-27Hy cannot currently be separated chromatographically, we could not determine the stereochemistry of the insect-produced components. Instead, we synthesized all stereoisomers and bioassayed synthetic blends in laboratory experiments. Of eight 2-component blends, each blend containing one of the two enantiomers of 5-me-27Hy and one of the four stereoisomers of 5,17-dime-27Hy, the blend of (5S)-methylheptacosane and (5R,17S)-dimethylheptacosane attracted males, whereas the blend of (5R)-methylheptacosane and (5R,17R)-dimethylheptacosane repelled males. Apparent recognition of both pheromone components and pheromone antagonists by males supports the hypothesis that the stereochemistry of 5-me-27Hy and 5,17-dime-27Hy, and possibly other methylated CHCs, may differ between male and female O. kuvanae, and that these differences may serve in mate attraction and recognition.

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Year:  2012        PMID: 23007309     DOI: 10.1007/s10886-012-0189-4

Source DB:  PubMed          Journal:  J Chem Ecol        ISSN: 0098-0331            Impact factor:   2.626


  36 in total

Review 1.  Mating behavior and chemical communication in the order Hymenoptera.

Authors:  M Ayasse; R J Paxton; J Tengö
Journal:  Annu Rev Entomol       Date:  2001       Impact factor: 19.686

2.  Electrophile-directed diastereoselective alkylation of prochiral enediolates.

Authors:  Stephen P Marsden; Rebecca Newton
Journal:  J Am Chem Soc       Date:  2007-10-03       Impact factor: 15.419

3.  Gnathotrichus sulcatus: synergistic response to enantiomers of the aggregation pheromone sulcatol.

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Journal:  Science       Date:  1976-05-28       Impact factor: 47.728

4.  Pheromonal basis of courtship behavior in two gypsy moth parasitoids:Brachymeria intermedia (Nees) andBrachymeria lasus (Walker) (Hymenoptera: Chalcididae).

Authors:  M A Mohamed; H C Coppel
Journal:  J Chem Ecol       Date:  1987-05       Impact factor: 2.626

5.  Chemical communication in scarab beetles: reciprocal behavioral agonist-antagonist activities of chiral pheromones.

Authors:  W S Leal
Journal:  Proc Natl Acad Sci U S A       Date:  1996-10-29       Impact factor: 11.205

6.  Enantiomers of (Z,Z)-6,9-heneicosadien-11-ol: sex pheromone components of Orgyia detrita.

Authors:  Regine Gries; Grigori Khaskin; Eugene Khaskin; John L Foltz; Paul W Schaefer; Gerhard Gries
Journal:  J Chem Ecol       Date:  2003-10       Impact factor: 2.626

7.  VARIATIONS IN CUTICULAR HYDROCARBONS AMONG THE EIGHT SPECIES OF THE DROSOPHILA MELANOGASTER SUBGROUP.

Authors:  Jean-Marc Jallon; Jean R David
Journal:  Evolution       Date:  1987-03       Impact factor: 3.694

8.  Identification and characterization of cuticular hydrocarbons from a rapid species radiation of Hawaiian swordtailed crickets (Gryllidae: Trigonidiinae: Laupala).

Authors:  Sean P Mullen; Jocelyn G Millar; Coby Schal; Kerry L Shaw
Journal:  J Chem Ecol       Date:  2008-01-19       Impact factor: 2.626

9.  Optical isomers of 3,13-dimethylheptadecane: Sex pheromone components of the western false hemlock looper,Nepytia freemani (Lepidoptera: Geometridae).

Authors:  G G Skip King; R Gries; G Gries; K N Slessor
Journal:  J Chem Ecol       Date:  1995-12       Impact factor: 2.626

10.  Species discrimination in five species of winter-flying geometrids (Lepidoptera) based on chirality of semiochemicals and flight season.

Authors:  G Szöcs; M Tóth; W Francke; F Schmidt; P Philipp; W A König; K Mori; B S Hansson; C Löfstedt
Journal:  J Chem Ecol       Date:  1993-11       Impact factor: 2.626

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  6 in total

1.  A male-predominant cuticular hydrocarbon, 7-methyltricosane, is used as a contact pheromone in the western flower thrips Frankliniella occidentalis.

Authors:  Oladele A Olaniran; Akella V S Sudhakar; Falko P Drijfhout; Ian A N Dublon; David R Hall; James G C Hamilton; William D J Kirk
Journal:  J Chem Ecol       Date:  2013-03-22       Impact factor: 2.626

2.  Isolation and determination of absolute configurations of insect-produced methyl-branched hydrocarbons.

Authors:  Jan E Bello; J Steven McElfresh; Jocelyn G Millar
Journal:  Proc Natl Acad Sci U S A       Date:  2015-01-12       Impact factor: 11.205

3.  Elucidating Structure-Bioactivity Relationships of Methyl-Branched Alkanes in the Contact Sex Pheromone of the Parasitic Wasp Lariophagus distinguendus.

Authors:  Stephan Kühbandner; Jan E Bello; Kenji Mori; Jocelyn G Millar; Joachim Ruther
Journal:  Insects       Date:  2013-12-03       Impact factor: 2.769

4.  Courtship behavior and identification of a sex pheromone in Ibalia leucospoides (Hymenoptera: Ibaliidae), a larval parasitoid of Sirex noctilio (Hymenoptera: Siricidae).

Authors:  Hajar Faal; Peter J Silk; Peter D Mayo; Stephen A Teale
Journal:  PeerJ       Date:  2021-11-04       Impact factor: 2.984

5.  The Importance of Methyl-Branched Cuticular Hydrocarbons for Successful Host Recognition by the Larval Ectoparasitoid Holepyris sylvanidis.

Authors:  Sarah Awater-Salendo; Hartwig Schulz; Monika Hilker; Benjamin Fürstenau
Journal:  J Chem Ecol       Date:  2020-10-29       Impact factor: 2.626

6.  Males of the parasitoid wasp, Nasonia vitripennis, can identify which fly hosts contain females.

Authors:  Garima Prazapati; Ankit Yadav; Anoop Ambili; Abhilasha Sharma; Rhitoban Raychoudhury
Journal:  R Soc Open Sci       Date:  2022-01-26       Impact factor: 2.963

  6 in total

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