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Spinosyn insecticides

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Abstract

The spinosyns found in the bacterial species Saccharopolyspora spinosa were first isolated from a soil sample from an abandoned rum distillery on the British Virgin Islands. Their anti-insecticidal activity against several commercially relevant pests is based on the allosteric, agonistic binding at the nicotinic acetylcholine receptor and an antagonistic effect on the γ-aminobutyric acid receptor. Spinosyns result from the polyketide pathway. The biosynthesis of the tetracyclic lactone comprises an enzymatic Diels–Alder and a Rauhut–Currier-like reaction followed by glycosylation with rhamnose and forosamine. The spinosyns, constituting the insecticidal active ingredients in Spinosad® and Spinetoram® from Dow AgroSciences, are manufactured by fermentation. However, in recent years, facilitated by computer-aided molecular modeling and bioactivity directed synthesis, novel highly potent, structurally simplified spinosyn analogs were discovered, which might be accessible in the future by total synthesis on an industrial scale.

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(© public domain, credit to Jim Buckman)

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(Image courtesy of Jae Kyung Sohng, Sun Moon University, Asan, South Korea)

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(Image is courtesy of Adrian T. Keatinge-Clay, University of Texas at Austin, Austin, Texas)

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Acknowledgements

We are indebted to Gary D. Crouse (formerly Dow AgroSciences) for valuable suggestions and careful proof-reading.

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  1. Department of Biosystems Science and Engineering, ETH Zurich, Basel, Switzerland

    Raghavendra Ramachanderan

  2. Ruprecht-Karls-Universität Heidelberg, BASF SE, RCS/ON, B009, 67056, Ludwigshafen am Rhein, Germany

    Bernd Schaefer

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Ramachanderan, R., Schaefer, B. Spinosyn insecticides. ChemTexts 6, 20 (2020). https://doi.org/10.1007/s40828-020-00113-y

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