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

Author:
Ancheeva, Elena, Mándi, Attila, Király, Sándor B., Kurtán, Tibor, Hartmann, Rudolf, Akone, Sergi H., Weber, Horst, Daletos, Georgios, Proksch, Peter
Source:
Journal of natural products 2018 v.81 no.11 pp. 2392-2398
ISSN:
1520-6025
Subject:
Chaetomium, Pseudomonas aeruginosa, autoclaving, bacteria, biosynthesis, endophytes, fermentation, fungi, isoquinoline alkaloids, nuclear magnetic resonance spectroscopy, stereoisomers
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.
Agid:
6225213