title: Parapheromones for Thynnine Wasps.
abstract: Sexually deceptive orchids produce floral volatiles that attract male insect pollinators. This interaction between flower and pollinator normally is highly specific. In the few cases where the chemical composition of the volatiles is known, the compounds have been found to be identical to those that comprise the sex pheromone of the female wasp. In this study, we investigated whether there is potential for flexibility in the molecular structure of the chemical cues used to mediate these specific interactions. Specifically, we asked whether strong sexual attraction can be maintained with structural modifications of sex pheromone components. Our study focused on the orchid, Drakaea glyptodon, which is pollinated by males of the thynnine wasp, Zaspilothynnus trilobatus. Three alkylpyrazines and a unique hydroxymethylpyrazine are components of the female produced sex pheromone of Z. trilobatus, and also the semiochemicals produced by the orchid that lures the males as pollinators. A blend of 2-butyl-3,5-dimethylpyrazine and 2-hydroxymethyl-3,5-diethyl-6-methylpyrazine (3:1) is as attractive as the full blend of four compounds. Therefore, in this study we substituted 2-hydroxymethyl-3,5-diethyl-6-methylpyrazine with one of five structurally related parapheromones in a blend with 2-butyl-3,5-dimethylpyrazine. All blends tested stimulated approaches by male wasps, with some also eliciting landing and attempted copulation. High-level calculations (G4(MP2)) showed the energy differences between the structural isomers were small, although the degree of sexual attraction varied, indicating the importance of structural factors for activity. One of the parapheromones, 2-hydroxymethyl-3,5-dimethyl-6-ethylpyrazine, elicited similar proportions of approaches, landings, and attempted copulations as the sex pheromone at the ratio and dose tested. The findings suggest that there is potential for chemical flexibility in the evolution of sexual deception.
authors.affiliation: Research School of Chemistry, The Australian National University, Canberra, ACT, 0200, Australia. bjorn.bohman@anu.edu.au.|Research School of Biology, The Australian National University, Canberra, ACT, 0200, Australia. bjorn.bohman@anu.edu.au.|School of Chemistry and Biochemistry, The University of Western Australia, Crawley, WA, 6009, Australia. bjorn.bohman@anu.edu.au.
authors.forename: Björn
authors.initials: B
authors.lastname: Bohman
authors.affiliation: School of Chemistry and Biochemistry, The University of Western Australia, Crawley, WA, 6009, Australia.
authors.forename: Amir
authors.initials: A
authors.lastname: Karton
authors.affiliation: Research School of Chemistry, The Australian National University, Canberra, ACT, 0200, Australia.
authors.forename: Ruby C M
authors.initials: RC
authors.lastname: Dixon
authors.affiliation: Research School of Chemistry, The Australian National University, Canberra, ACT, 0200, Australia.
authors.forename: Russell A
authors.initials: RA
authors.lastname: Barrow
authors.affiliation: Research School of Biology, The Australian National University, Canberra, ACT, 0200, Australia.|School of Chemistry and Biochemistry, The University of Western Australia, Crawley, WA, 6009, Australia.
authors.forename: Rod
authors.initials: R
authors.lastname: Peakall
mesh_terms: D000818:Animals; D001522:Behavior, Animal / Q000187:drug effects; D005260:Female; D008297:Male; D011719:Pyrazines / Q000737:chemistry / Q000494:pharmacology; D012724:Sex Attractants / Q000737:chemistry* / Q000494:pharmacology; D014863:Wasps / Q000187:drug effects* / Q000502:physiology
chemical_list: D011719:Pyrazines; D012724:Sex Attractants
keywords: Drakaea; Parapheromone; Pyrazine; Sexual deception; Specificity