Frogolide – An Unprecedented Sesquiterpene Macrolactone from Scent Glands of African Frogs

Menke, Markus; Melnik, Kristina; Peram, Pardha Saradhi; Starnberger, Iris; Hödl, Walter; Vences, Miguel; Schulz, Stefan

doi:10.1002/ejoc.201800199

Cited by 17 publications

(26 citation statements)

References 29 publications

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“…A tri-modal system involved in mate recognition and courtship is suggested for the African reed frogs (Hyperoliidae) (Starnberger et al 2014b ). Males of this family have gular glands on their often colorful vocal sacs, which produce sex and species-specific chemical cocktails (Starnberger et al 2013 ; Menke et al 2016 , 2018 ; Melnik et al 2019 ). The exact interplay between visual, auditory, and chemical cues in mating behavior are however not fully understood.…”

Section: “Water-to-land” Transition In Evolution Development and Inmentioning

confidence: 99%

Olfaction across the water–air interface in anuran amphibians

2021

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Extant anuran amphibians originate from an evolutionary intersection eventually leading to fully terrestrial tetrapods. In many ways, they have to deal with exposure to both terrestrial and aquatic environments: (i) phylogenetically, as derivatives of the first tetrapod group that conquered the terrestrial environment in evolution; (ii) ontogenetically, with a development that includes aquatic and terrestrial stages connected via metamorphic remodeling; and (iii) individually, with common changes in habitat during the life cycle. Our knowledge about the structural organization and function of the amphibian olfactory system and its relevance still lags behind findings on mammals. It is a formidable challenge to reveal underlying general principles of circuity-related, cellular, and molecular properties that are beneficial for an optimized sense of smell in water and air. Recent findings in structural organization coupled with behavioral observations could help to understand the importance of the sense of smell in this evolutionarily important animal group. We describe the structure of the peripheral olfactory organ, the olfactory bulb, and higher olfactory centers on a tissue, cellular, and molecular levels. Differences and similarities between the olfactory systems of anurans and other vertebrates are reviewed. Special emphasis lies on adaptations that are connected to the distinct demands of olfaction in water and air environment. These particular adaptations are discussed in light of evolutionary trends, ontogenetic development, and ecological demands.

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Section: “Water-to-land” Transition In Evolution Development and Inmentioning

confidence: 99%

Olfaction across the water–air interface in anuran amphibians

2021

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“…Furthermore, microhydrogenation of an available extract led to a saturated lactone consistent with this proposal. 63 Dihydrofarnesol 116 can be readily obtained from (2E,6E)-farnesol (115) in high yield and ee using Noyori's enantioselective hydrogenation with a Ru-BINAP catalyst (Scheme 16). 64 Again stepwise oxidation was beneficial, using Parikh-Doering and Pinnick-Lindgren methods, followed by methylation to arrive at methyl (S)-dihydrofarnesenoate (118) when an R catalyst was used.…”

Section: Account Synlettmentioning

confidence: 99%

“…64 Again stepwise oxidation was beneficial, using Parikh-Doering and Pinnick-Lindgren methods, followed by methylation to arrive at methyl (S)-dihydrofarnesenoate (118) when an R catalyst was used. 63 Oxidation with IBX led to cyclization of byproducts while 2azaadamantane N-oxyl (AZADO) and PhI(OAc) 2 gave lower yields. Riley oxidation of 118 delivered then exclusively the E product 119, but a byproduct was regioisomer 120.…”

Section: Account Synlettmentioning

confidence: 99%

Chemical Diversity of Volatile Macrocylic Lactones from Frogs

Schulz¹,

Poth²,

Peram³

et al. 2021

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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 will 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 will 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. 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.

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“…6 Frogolide 8 has been identified in the scent glands of several African frogs including Hyperolius viridiflavus. 7 Frogolide is the first sesquiterpenoid macrolactone to be isolated from frogs as most frog macrolides are derived from the fatty acid pathway.…”

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confidence: 99%