Frogolide - An Unprecedented Sesquiterpene Macrolactone from Scent Glands of African Frogs
| Autor: | Miguel Vences, Kristina Melnik, Walter Hödl, Iris Starnberger, Pardha Saradhi Peram, Markus Menke, Stefan Schulz |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
Scent gland 010405 organic chemistry Organic Chemistry Absolute configuration Zoology Fatty acid 010402 general chemistry Sesquiterpene 01 natural sciences Terpenoid 0104 chemical sciences Terpene chemistry.chemical_compound chemistry Sex pheromone Physical and Theoretical Chemistry Macrocyclic lactone |
| Zdroj: | European Journal of Organic Chemistry. 2018:2651-2656 |
| ISSN: | 1434-193X |
| DOI: | 10.1002/ejoc.201800199 |
| Popis: | Some amphibians use chemical signals in addition to optical and acoustical signals to transmit information. Males of mantellid frogs from Madagascar and hyperoliid frogs from Africa emit complex, species- and sex-specific bouquets of volatiles from their femoral or gular glands. We report here on the identification, synthesis, and determination of the absolute configuration of a macrocyclic lactone occurring in several species of both families, (S)-3,7,11-dodec-6,10-dien-12-olide (S-14, frogolide). Macrolides are a preferred compound class of frog volatiles. Nevertheless, frogolide is the first macrocyclic lactone obviously derived from the terpene pathway, in contrast to known frog macrolides that are usually formed via the fatty acid biosynthetic pathway. |
| Databáze: | OpenAIRE |
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