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Beetles Do It Differently : Two Stereodivergent Cyclisation Modes in Iridoid-Producing Leaf-Beetle Larvae

Title data

Kunert, Maritta ; Rahfeld, Peter ; Shaker, Kamel H. ; Schneider, Bernd ; David, Anja ; Dettner, Konrad ; Pasteels, Jacques M. ; Boland, Wilhelm:
Beetles Do It Differently : Two Stereodivergent Cyclisation Modes in Iridoid-Producing Leaf-Beetle Larvae.
In: ChemBioChem. Vol. 14 (2013) Issue 3 . - pp. 353-360.
ISSN 1439-7633
DOI: https://doi.org/10.1002/cbic.201200689

Abstract in another language

Larvae of the Chrysomelina species Phaedon cochleariae, Hydrothassa marginella, Phratora vulgatissima, Gastrophysa viridula, Gastrophysa atrocyanea, Gastrophysa cyanea and Gastrophysa polygoni produce the iridoid chrysomelidial (1) to defend themselves against predators. Feeding experiments with a deuterated precursor ([(2) H(5) ]8-hydroxygeraniol 9) and in vitro isotope exchange experiments with defensive secretion in (2) H(2) O revealed differences in the cyclisation of the ultimate precursor 8-oxogeranial (8) to 1, between members of the genus Gastrophysa and all other species. In P. cochleariae, H. marginella and P. vulgatissima 1 is most likely produced by a Rauhut-Currier-type cyclisation via a "transoid dienamine", with loss of a single deuterium atom from C(4) of the precursor. In contrast, members of the genus Gastrophysa cyclise 8 via a "cisoid dienamine" intermediate, with exchange of all three deuterium atoms from the methyl group at C(3). To study whether the different cyclisation modes influence the stereochemistry of 1, the absolute configuration of 1 of the larvae was determined by GC-MS on a chiral column. In accordance with literature (J. Meinwald, T. H. Jones, J. Am. Chem. Soc. 1978, 100, 1883 and N. Shimizu, R. Yakumaru, T. Sakata, S. Shimano, Y. Kuwahara, J. Chem. Ecol. 2012, 38, 29), we found (5S,8S)-chrysomelidial (1) in H. marginella and P. vulgatissima, but P. cochleariae and all investigated members of the genus Gastrophysa synthesise (5R,8R)-chrysomelidial (1).

Further data

Item Type: Article in a journal
Refereed: Yes
Additional notes: BAYCEER113542
Institutions of the University: Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Biology > Chair Animal Ecology II - Evolutionary Animal Ecology
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Biology > Former Professors > Chair Animal Ecology II - Univ.-Prof. Dr. Konrad Dettner
Research Institutions > Research Centres > Bayreuth Center of Ecology and Environmental Research- BayCEER
Faculties
Faculties > Faculty of Biology, Chemistry and Earth Sciences
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Biology
Research Institutions
Research Institutions > Research Centres
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Biology > Former Professors
Result of work at the UBT: Yes
DDC Subjects: 500 Science
Date Deposited: 24 Apr 2015 11:56
Last Modified: 07 Sep 2015 08:30
URI: https://eref.uni-bayreuth.de/id/eprint/11408