Structure and Biosynthesis of Chaetocyclinones, New Polyketides Produced by an Endosymbiotic Fungus

Sandra Lösgen, Oliver Schlörke, K. Meindl, Regine Herbst‐Irmer, Axel Zeeck

European Journal of Organic Chemistry · 2007 · 53 citations · 18 references

Concepts

Abstract

Abstract Three new fungal polyketide metabolites, chaetocyclinone A to C, were produced by cultures of Chaetomium sp. (strain Gö 100/2), which was isolated from marine algae. The structures of the novel compounds were established by detailed spectroscopic analysis. Additionally, an X‐ray analysis of chaetocyclinone C ( 5 ) was performed. Chaetocyclinone A ( 1 ) exhibits inhibitory activity against selected phytopathogenic fungi. The biosynthesis of 1 and 5 was studied by feeding 13 C‐labelled acetate. The results suggest the polyketide pathway for the isolated metabolites. In the case of chaetocyclinone C ( 5 ), we assume an unusual condensation of two highly reactive heptaketide intermediates. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

References

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