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Research article - Peer-reviewed, 2020

Identification of (Z)-8-Heptadecene and n-Pentadecane as Electrophysiologically Active Compounds in Ophrys insectifera and Its Argogorytes Pollinator

Bohman, Bjoern; Weinstein, Alyssa M.; Mozuraitis, Raimondas; Flematti, Gavin R.; Borg-Karlson, Anna-Karin


Sexually deceptive orchids typically depend on specific insect species for pollination, which are lured by sex pheromone mimicry. European Ophrys orchids often exploit specific species of wasps or bees with carboxylic acid derivatives. Here, we identify the specific semiochemicals present in O. insectifera, and in females of one of its pollinator species, Argogorytes fargeii. Headspace volatile samples and solvent extracts were analysed by GC-MS and semiochemicals were structurally elucidated by microderivatisation experiments and synthesis. (Z)-8-Heptadecene and n-pentadecane were confirmed as present in both O. insectifera and A. fargeii female extracts, with both compounds being found to be electrophysiologically active to pollinators. The identified semiochemicals were compared with previously identified Ophrys pollinator attractants, such as (Z)-9 and (Z)-12-C-27-C-29 alkenes in O. sphegodes and (Z)-9-octadecenal, octadecanal, ethyl linoleate and ethyl oleate in O. speculum, to provide further insights into the biosynthesis of semiochemicals in this genus. We propose that all these currently identified Ophrys semiochemicals can be formed biosynthetically from the same activated carboxylic acid precursors, after a sequence of elongation and decarbonylation reactions in O. sphegodes and O. speculum, while in O. insectifera, possibly by decarbonylation without preceding elongation.


Ophrys; sexual deception; semiochemicals; fly orchid; pollination

Published in

International Journal of Molecular Sciences
2020, volume: 21, number: 2, article number: 620
Publisher: MDPI

Authors' information

University of Western Australia
Swedish University of Agricultural Sciences, Department of Plant Protection Biology
Weinstein, Alyssa M.
Australian Natl Univ
Mozuraitis, Raimondas
Stockholm Univ
Flematti, Gavin R.
Univ Western Australia
Borg-Karlson, Anna-Karin
Mid Sweden Univ

UKÄ Subject classification

Biochemistry and Molecular Biology

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