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Convergent Evolution of Biosynthesis Across Kingdoms: Bicyclic Ketals in BarkBeetles and Their Fungal Symbionts
Linnaeus University, Faculty of Health and Life Sciences, Department of Chemistry and Biomedical Sciences. (Rikard Unelius)ORCID iD: 0000-0002-8849-9883
(English)In: Article in journal (Refereed) Submitted
Abstract [en]

The convergent evolution of biosynthesis betweenorganisms of different kingdoms is a rarely described phenomenon.Here we show that fungi associated with bark beetles can synthesizeessential bicyclic ketal pheromones of economically important barkbeetle species. Four fungal symbionts produced a range of bicyclicketals, including bark beetle aggregation pheromones andsemiochemicals (exo- and endo-brevicomin) and two structurallyrelated pheromone candidates (exo- and endo-1,3-dimethyl-2,9-dioxa-bicyclo[3.3.1]nonane). Further, a repellent of many bark beetlespecies, (5S,7S)-trans-conophthorin, was produced by two of thevirulent fungi. We prepared all enantiomers of brevicomin and 1,3-dimethyl-2,9-dioxabicyclo[3.3.1]nonane to confirm that theenantiomeric composition of the fungi-produced ketals matched thosepreviously reported from bark beetles. As the mutualism betweenfungi and bark beetles seems intricate, and thus potentially vulnerableto disruption, our findings may lay the foundation for the use of fungalmetabolites in new innovative management strategies to control barkbeetle pests.

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Environmental Sciences
Research subject
Environmental Science, Environmental Chemistry
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URN: urn:nbn:se:lnu:diva-73328OAI: oai:DiVA.org:lnu-73328DiVA, id: diva2:1200074
Available from: 2018-04-23 Created: 2018-04-23 Last updated: 2018-04-24

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Ganji, Suresh

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CiteExportLink to record
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