New C26 delta-lactones from the Dufour's gland of the urticating ant Tetramorium aculeatum. |
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Authors: | P Merlin J C Braekman D Daloze J M Pasteels A Dejean |
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Institution: | Laboratory of Bio-Organic Chemistry, Faculty of Sciences, University of Brussels, Belgium. |
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Abstract: | (6R*)-(2S*)-2-hydroxyheneicos-12-enyl]-5,6-dihydro-2H-pyran-2-one (1) degree is the major constituent of the secretion of freshly dissected Dufour's gland of the urticating ant Tetramorium aculeatum. In solution, compound 1 is slowly transformed into (1S*,5R*,7S*)-7-(nonadec-10-enyl)-2,6-dioxabicyclo3.3.1] nonan-3-one (2) degrees on standing. The structures of compounds 1 and 2 have been established on the basis of their spectral and chemical properties. Compound 1 could be responsible for the urticating properties of the ant. |
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