Identification and Synthesis of Luteolide, a Highly Branched Macrolide Semiochemical from the Mantellid Frog Gephyromantis luteus
journal contributionposted on 04.04.2019, 15:10 by Kristina Melnik, Markus Menke, Andolalao Rakotoarison, Miguel Vences, Stefan Schulz
Luteolide is a 10-membered aliphatic macrolactone, (4R,8S,9S)-4,8-dimethylundecan-9-olide ((−)-17), released by the femoral gland of males of the mantellid frog Gephyromantis luteus. Its structure was established using NMR, MS, and chiral GC and confirmed by stereoselective synthesis of different stereoisomers. Among the approximately 20 current macrolides known from the Mantellidae, luteolide is the first example of a volatile macrolide furnishing three stereogenic centers and an ethyl side chain.
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-9-olidestereoisomerstereogenic centersidentificationdimethylundecanethyl side chainMantellid Frog Gephyromantis luteus Luteolidemacrolide furnishingstereoselective synthesisfemoral glandBranched Macrolide Semiochemical10- membered aliphatic macrolactoneNMRMantellidaeluteolideMSmantellid frog Gephyromantis luteusSynthesichiral GC