| Title: | A synthetic dodecanolide library for the identification of putative semiochemicals emitted by mantellid frogs |
| Author(s): | Peram PS; Vences M; Schulz S; |
| Address: | "Institute of Organic Chemistry, Technische Universitat Braunschweig, Hagenring 30, 38106 Braunschweig, Germany. stefan.schulz@tu-bs.de" |
| ISSN/ISBN: | 1477-0539 (Electronic) 1477-0520 (Linking) |
| Abstract: | "Aliphatic macrolides are used by various organisms as semiochemicals or pheromones, e.g. by the endemic Madagascan frog family Mantellinae. Volatile, methyl-branched aliphatic macrolides occur in various species, but their identification by MS is difficult, while isolation is not possible due to the low amounts produced. Therefore, we synthesized a library of methyl-branched 11-dodecanolides to identify unknown macrolides secreted by Gephyromantis moseri, a mantelline frog restricted to the rainforest and characterized by largely terrestrial habitats. The syntheses used metal-organic epoxide opening and ring-closing-metathesis as key steps. All library members 2-, 4-, 6-, 8-, and 10-methyl-11-dodecanolide were thus identified as part of the secretion by comparison of their mass spectra and their gas chromatographic retention indices. These compounds comprise new natural products" |
| Keywords: | Animals Anura/*metabolism Gas Chromatography-Mass Spectrometry Macrolides/*chemistry/metabolism Male Pheromones/*chemistry/metabolism; |
| Notes: | "MedlinePeram, Pardha Saradhi Vences, Miguel Schulz, Stefan eng England 2017/08/10 Org Biomol Chem. 2017 Aug 23; 15(33):6967-6977. doi: 10.1039/c7ob00849j" |
