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Stereoselective Chemical Defense in the Drosophila Parasitoid Leptopilina heterotoma is Mediated by (−)-Iridomyrmecin and (+)-Isoiridomyrmecin

Title data

Stökl, Johannes ; Hofferberth, John ; Pritschet, Maria ; Brummer, Michael ; Ruther, Joachim:
Stereoselective Chemical Defense in the Drosophila Parasitoid Leptopilina heterotoma is Mediated by (−)-Iridomyrmecin and (+)-Isoiridomyrmecin.
In: Journal of Chemical Ecology. Vol. 38 (2012) Issue 4 . - pp. 331-339.
ISSN 1573-1561
DOI: https://doi.org/10.1007/s10886-012-0103-0

Abstract in another language

Chemical defense mechanisms are widespread among insects but have rarely been demonstrated in parasitoid wasps. Here, we show that the Drosophila parasitoid Leptopilina heterotoma (Hymenoptera, Figitidae) produces (−)-iridomyrmecin and (+)-isoiridomyrmecin in a cephalic gland, and that these chemicals have a highly repellent effect on ants. Stereoselective synthesis of 4 stereoisomers of iridomyrmecin allowed us to demonstrate that the repellent effect of iridomyrmecins depends on the stereochemistry. Potential food items impregnated with natural doses of (−)-iridomyrmecin were avoided by ants much longer than those impregnated with (+)-iridomyrmecin, (+)-isoiridomyrmecin, or (−)-isoiridomyrmecin, respectively. Quantitative headspace analyses revealed furthermore that females and males of L. heterotoma released iridomyrmecins in higher amounts when confronted with ants. This is the first time, that (−)-iridomyrmecin and (+)-isoiridomyrmecin are reported as natural products. Females synthesize more iridomyrmecins than males, and the most active (−)-iridomyrmecin is produced by females only. We, therefore, hypothesize that this defense mechanism is used mainly by female wasps when foraging for Drosophila larvae on rotten fruits, but also may protect male wasps during dispersal.

Further data

Item Type: Article in a journal
Refereed: Yes
Additional notes: BAYCEER147421
Keywords: Leptopilina; Drosophila; Iridomyrmecin; Isoiridomyrmecin; Chemical defense
Institutions of the University: Faculties > Faculty of Biology, Chemistry and Earth Sciences
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Biology > Chair Animal Ecology II - Evolutionary Animal Ecology > Chair Animal Ecology II - Evolutionary Animal Ecology - Univ.-Prof. Dr. Sandra Steiger
Research Institutions
Research Institutions > Research Centres
Research Institutions > Research Centres > Bayreuth Center of Ecology and Environmental Research- BayCEER
Result of work at the UBT: No
DDC Subjects: 500 Science
Date Deposited: 15 Apr 2019 06:52
Last Modified: 15 Apr 2019 06:52
URI: https://eref.uni-bayreuth.de/id/eprint/48376