| Title: | "Purification, identification, concentration and bioactivity of (Z)-7-dodecen-1-yl acetate: sex pheromone of the female Asian elephant, Elephas maximus" |
| Author(s): | Rasmussen LE; Lee TD; Zhang A; Roelofs WL; Daves GD; |
| Address: | "Department of Chemistry, Biochemistry, and Molecular Biology, Oregon Graduate Institute of Science and Technology, Portland 97291-1000, USA" |
| ISSN/ISBN: | 0379-864X (Print) 0379-864X (Linking) |
| Abstract: | "In their natural ecosystems, adult male and female Asian elephants, Elephas maximus, live separately. For several weeks prior to ovulation, female elephants release a substance in their urine which elicits a high frequency of non-habituating chemosensory responses, especially flehmen responses, from male elephants. These responses occur prior to, and are an integral part of, mating. Using bioassay-guided fractionation, quantitatively dependent on these chemosensory responses, a specific sex pheromone was isolated and purified by an alternating series of organic and/or aqueous extractions, column chromatography, gas chromatography and high-performance liquid chromatography. Using primarily 1H-proton nuclear magnetic resonance (NMR) spectrometry and gas chromatography-mass spectrometry (GC-MS) of the urine-derived pheromone and its dimethyl disulfide derivative, we determined the structure of the active compound to be (Z)-7-dodecen-1-yl acetate (Z7-12:Ac). Concentrations of Z7-12:Ac in the female urine increased from non-detectable during the luteal phase to 0.48 microgram/ml (0.002 mM) early in the follicular phase and to 33.0 micrograms/ml (0.146 mM) just prior to ovulation. Bioassays with commercially available authentic synthetic Z7-12:Ac, using 10 Asian male elephants at several locations in the US, demonstrated quantitatively elevated chemosensory responses that were robust during successive tests, and several mating-associated behaviors. Bioassays with Z7-12:Ac with adult male elephants dwelling in more natural social situations in forest camps in Myanmar revealed some differing contextual pre-mating behavioral components. The remarkable convergent evolution of this compound suggests that compounds identified in mammalian exudates that are also present in pheromone blends of insects should be re-evaluated as potential mammalian chemosignals" |
| Keywords: | "Animals Biological Assay Chromatography, Gas Chromatography, High Pressure Liquid Dodecanol/*analogs & derivatives/isolation & purification/pharmacology/urine Elephants Estrus/metabolism/urine Female Magnetic Resonance Spectroscopy Male Mass Spectrometry;" |
| Notes: | "MedlineRasmussen, L E Lee, T D Zhang, A Roelofs, W L Daves, G D Jr eng R01 HD19219/HD/NICHD NIH HHS/ Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, P.H.S. England 1997/08/01 Chem Senses. 1997 Aug; 22(4):417-37. doi: 10.1093/chemse/22.4.417" |
