Expanding the Metabolic Profile of the Fungus Chaetomium sp. through Co-culture with Autoclaved Pseudomonas aeruginosa

Elena Ancheeva, Lisa Küppers, Sergi Herve Akone, Weaam Ebrahim, Zhen Liu, Attila Mándi, T. Kurtán, Wenhan Lin, Raha Orfali, Nidja Rehberg, Rainer Kalscheuer, Georgios Daletos, Peter Proksch

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18 Citations (Scopus)

Abstract

The mixed fermentation of the fungal endophyte Chaetomium sp. with an autoclaved culture of the bacterium Pseudomonas aeruginosa on solid rice medium led to an up to 33-fold increase in the accumulation of constitutively present fungal secondary metabolites (3–10), which included four new butenolide derivatives (3–5 and 7). In addition, two further shikimic acid analogues (1 and 2) were obtained from mixed cultures that were neither detected in axenic cultures of the fungus nor of the bacterium. Chaetoisochorismin (1) possesses an unusual (3-methoxycarbonylphenyl)pyruvate core structure. The structures of the new compounds were unequivocally elucidated by HRESIMS, one- and two-dimensional NMR analysis as well as by comparison with literature data. The absolute configurations of the structures of the new derivatives 1 and 2 were established by ECD calculations as well as by the modified Mosher's method. Compounds 1–3 and 5–7 were subjected to antimicrobial and cytotoxicity assays but were shown to be inactive.

Original languageEnglish
Pages (from-to)3256-3264
Number of pages9
JournalEuropean Journal of Organic Chemistry
Volume2017
Issue number22
DOIs
Publication statusPublished - Jun 16 2017

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Keywords

  • Autoclaved Pseudomonas aeruginosa
  • Biosynthesis
  • Chaetomium sp.
  • Shikimic acid derivatives
  • Structure elucidation
  • TDDFT-ECD calculations

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Ancheeva, E., Küppers, L., Akone, S. H., Ebrahim, W., Liu, Z., Mándi, A., Kurtán, T., Lin, W., Orfali, R., Rehberg, N., Kalscheuer, R., Daletos, G., & Proksch, P. (2017). Expanding the Metabolic Profile of the Fungus Chaetomium sp. through Co-culture with Autoclaved Pseudomonas aeruginosa. European Journal of Organic Chemistry, 2017(22), 3256-3264. https://doi.org/10.1002/ejoc.201700288