A synthetic dodecanolide library for the identification of putative semiochemicals emitted by mantellid frogs
| Autor: | Pardha Saradhi Peram, Miguel Vences, Stefan Schulz |
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| Rok vydání: | 2017 |
| Předmět: |
Male
biology 010405 organic chemistry Chemistry Organic Chemistry 010402 general chemistry biology.organism_classification 01 natural sciences Biochemistry Gas Chromatography-Mass Spectrometry Pheromones 0104 chemical sciences Mantellinae Sex pheromone Botany Animals Identification (biology) Macrolides Anura Physical and Theoretical Chemistry Gephyromantis moseri |
| Zdroj: | Organic & Biomolecular Chemistry. 15:6967-6977 |
| ISSN: | 1477-0539 1477-0520 |
| DOI: | 10.1039/c7ob00849j |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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