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Frogolide – An Unprecedented Sesquiterpene Macrolactone from Scent Glands of African Frogs
Author(s) -
Menke Markus,
Melnik Kristina,
Peram Pardha S.,
Starnberger Iris,
Hödl Walter,
Vences Miguel,
Schulz Stefan
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800199
Subject(s) - chemistry , lactone , terpene , terpenoid , sesquiterpene , stereochemistry , zoology , botany , biology
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.