Xanthocidin Derivatives from the Endophytic Streptomyces sp. AcE210 Provide Insight into Xanthocidin Biosynthesis

Xanthocidin and six new derivatives were isolated from the endophytic Streptomyces sp. AcE210. Their planar structures were elucidated by 1D and 2D NMR spectroscopy as well as by HRMS. The absolute configuration of one compound was determined by using vibrational circular dichroism spectroscopy (VCD...

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Published in:Chembiochem : a European journal of chemical biology 2018-12, Vol.19 (23), p.2472-2480
Main Authors: Ortlieb, Nico, Bretzel, Karin, Kulik, Andreas, Haas, Julian, Lüdeke, Steffen, Keilhofer, Nadine, Schrey, Silvia Diane, Gross, Harald, Niedermeyer, Timo Horst Johannes
Format: Article
Language:English
Subjects:
Absolute configuration
Biosynthesis
Chain branching
Circular dichroism
Congeners
Derivatives
Dichroism
Endophytes
Genomes
Homology
Magnetic resonance spectroscopy
methylenomycin
natural products
NMR spectroscopy
Nucleotide sequence
Planar structures
Spectroscopy
Spectrum analysis
Streptomyces
Valine
xanthocidin
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Summary:Xanthocidin and six new derivatives were isolated from the endophytic Streptomyces sp. AcE210. Their planar structures were elucidated by 1D and 2D NMR spectroscopy as well as by HRMS. The absolute configuration of one compound was determined by using vibrational circular dichroism spectroscopy (VCD). The structural similarities of xanthocidin and some of the isolated xanthocidin congeners to the methylenomycins A, B, and C suggested that the biosynthesis of these compounds might follow a similar route. Feeding studies with isotopically labelled [13C5]‐l‐valine showed that instead of utilizing acetyl‐CoA as starter unit, which has been proposed for the methylenomycin biosynthesis, Streptomyces sp. AcE210 employs an isobutyryl‐CoA starter unit, resulting in a branched side chain in xanthocidin. Further evidence for a comparable biosynthesis was given by the analysis of the genome sequence of Streptomyces sp. AcE210 that revealed a cluster of homologues to the mmy genes involved in methylenomycin biosynthesis. Branch management: Why has xanthocidin, in contrast to the closely related methylenomycin, a branched side chain? Isolation and identification of six novel xanthocidin derivatives from Streptomyces sp. AcE210 allowed us to hypothesise that isobutyryl‐CoA is used as the biosynthesis starter unit. We confirmed this by feeding studies with isotopically labelled [13C5]‐l‐valine. Bioinformatics analysis of the strain's genome revealed the xanthocidin biosynthetic gene cluster.
ISSN:1439-4227
1439-7633
DOI:10.1002/cbic.201800467