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DOI: 10.1055/a-1381-2881
Chemical Diversity of Volatile Macrocylic Lactones from Frogs
We thank the Deutsche Forschungsgemeinschaft for research grants (Grant No. SCHU 984/10-1 and SCHU 984/10-2).
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Dedicated to the memory of Prof. Dr. Dr. h. c. mult. Wittko Francke
Abstract
For a long time, frogs were believed to communicate primarily via the acoustic channel, but during the last decades it became obvious that various lineages also use chemical communication. In this Account we present our research on the identification of volatile lactones from Madagascan Mantellidae and African Hyperoliidae frogs. Both possess male specific glands that can disseminate a range of volatile compounds. Key constituents are macrocyclic lactones. They show high variability in structure and occurrence. We focus here on the synthetic approaches we have used to clarify constitution and configuration of the glandular compounds. Key synthetic methods are ring-closing metathesis and nucleophilic epoxide opening. Often, but not always, the natural compounds occurs in amounts that excludes their investigation by NMR spectroscopy. Instead, we use GC/MS analysis, GC/IR, microreactions, and synthesis to identify such components. Several aspects of our work will be described giving some insight in our scientific approach.
1 Introduction
2 Macrocylic Lactones from the Fatty Acid Biosynthetic Pathway
3 Unsaturated Lactones
4 Terpenoid Lactones
5 Macrolide Occurrence
6 Conclusions
Publication History
Received: 11 January 2021
Accepted after revision: 02 February 2021
Accepted Manuscript online:
02 February 2021
Article published online:
23 February 2021
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