Chaetolines A and B, Pyrano[3,2- f]isoquinoline Alkaloids from Cultivation of Chaetomium sp. in the Presence of Autoclaved Pseudomonas aeruginosa

Elena Ancheeva, Attila Mándi, Sándor B. Király, T. Kurtán, Rudolf Hartmann, Sergi H. Akone, Horst Weber, Georgios Daletos, Peter Proksch

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The first members of a new alkaloid class, chaetolines A (1) and B (2), which feature a pyrano[3,2-f]isoquinoline core structure, were obtained from a crude extract of the fungal endophyte Chaetomium sp. after cultivation in the presence of autoclaved Pseudomonas aeruginosa. The structures of the new compounds, including the absolute configuration of the major stereoisomer, were determined through detailed analysis of HRESIMS, 1D/2D NMR, and calculation of ECD data. The possible biosynthetic origin of the unprecedented scaffold of 1 and 2 is proposed. The current study provides further evidence for mixed fermentation as a powerful tool to induce the accumulation of cryptic fungal natural products even in the absence of viable bacterial cells.

Original languageEnglish
JournalJournal of Natural Products
DOIs
Publication statusAccepted/In press - Jan 1 2018

Fingerprint

Chaetomium
Endophytes
Stereoisomerism
Biological Products
Complex Mixtures
Alkaloids
Scaffolds
Fermentation
Pseudomonas aeruginosa
Nuclear magnetic resonance
isoquinoline

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

Cite this

Chaetolines A and B, Pyrano[3,2- f]isoquinoline Alkaloids from Cultivation of Chaetomium sp. in the Presence of Autoclaved Pseudomonas aeruginosa. / Ancheeva, Elena; Mándi, Attila; Király, Sándor B.; Kurtán, T.; Hartmann, Rudolf; Akone, Sergi H.; Weber, Horst; Daletos, Georgios; Proksch, Peter.

In: Journal of Natural Products, 01.01.2018.

Research output: Contribution to journalArticle

Ancheeva, Elena ; Mándi, Attila ; Király, Sándor B. ; Kurtán, T. ; Hartmann, Rudolf ; Akone, Sergi H. ; Weber, Horst ; Daletos, Georgios ; Proksch, Peter. / Chaetolines A and B, Pyrano[3,2- f]isoquinoline Alkaloids from Cultivation of Chaetomium sp. in the Presence of Autoclaved Pseudomonas aeruginosa. In: Journal of Natural Products. 2018.
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