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

Lösgen Sandra | Zendy; Schlörke Oliver | Zendy; Meindl Kathrin | Zendy; HerbstIrmer Regine | Zendy; Zeeck Axel | Zendy

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

Author(s) -

Lösgen Sandra,

Schlörke Oliver,

Meindl Kathrin,

HerbstIrmer Regine,

Zeeck Axel

Publication year - 2007

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200601020

Subject(s) - polyketide , biosynthesis , chemistry , fungus , stereochemistry , strain (injury) , polyketide synthase , chaetomium , biochemistry , botany , enzyme , biology , food science , penicillium , anatomy

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)

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