| Title: | Identification of (Z)-8-Heptadecene and n-Pentadecane as Electrophysiologically Active Compounds in Ophrys insectifera and Its Argogorytes Pollinator |
| Author(s): | Bohman B; Weinstein AM; Mozuraitis R; Flematti GR; Borg-Karlson AK; |
| Address: | "School of Molecular Sciences, the University of Western Australia, Crawley, WA 6009, Australia. Department of Plant Protection Biology, Swedish University of Agricultural Sciences, 23053 Alnarp, Sweden. Research School of Biology, the Australian National University, Acton, ACT 2601, Australia. Department of Zoology, Stockholm University, 106 91, Stockholm, Sweden. Department of Chemical Engineering, Mid Sweden University, 85170 Sundsvall, Sweden" |
| ISSN/ISBN: | 1422-0067 (Electronic) 1422-0067 (Linking) |
| Abstract: | "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" |
| Keywords: | Alkanes/analysis/chemistry/*pharmacology Alkenes/analysis/chemistry/*pharmacology Animals Bees Flowers/drug effects/*physiology Orchidaceae/drug effects/*physiology Pheromones/analysis/chemistry/*pharmacology Pollination Sex Attractants/analysis/chemistry; |
| Notes: | "MedlineBohman, Bjorn Weinstein, Alyssa M Mozuraitis, Raimondas Flematti, Gavin R Borg-Karlson, Anna-Karin eng DE160101313/Australian Research Council/ Switzerland 2020/01/23 Int J Mol Sci. 2020 Jan 17; 21(2):620. doi: 10.3390/ijms21020620" |
