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Chembiochem. 2018 Dec 4;19(23):2472-2480. doi: 10.1002/cbic.201800467. Epub 2018 Nov 6.

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

Author information

1
Department of Microbiology and Biotechnology, Interfaculty Institute of Microbiology and Infection Medicine, Eberhard Karls University Tübingen, Auf der Morgenstelle 28, 72076, Tübingen, Germany.
2
German Centre for Infection Research (DZIF), Partner Site Tübingen, Tübingen, Germany.
3
Department of Pharmaceutical Biology/Pharmacognosy, Institute of Pharmacy, Martin-Luther-University Halle-Wittenberg, Hoher Weg 8, 06120, Halle (Saale), Germany.
4
Institute of Pharmaceutical Sciences, Albert-Ludwigs-University Freiburg, Albertstrasse 25, 79104, Freiburg, Germany.
5
Department of Physiological Ecology of Plants, Interfaculty Institute of Microbiology and Infection Medicine, Eberhard Karls University Tübingen, Auf der Morgenstelle 5, 72076, Tübingen, Germany.
6
IBG-2: Plant Sciences, Forschungszentrum Jülich, 52425, Jülich, Germany.
7
Department of Pharmaceutical Biology, Pharmaceutical Institute, Eberhard Karls University Tübingen, Auf der Morgenstelle 8, 72076, Tübingen, Germany.

Abstract

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 [13 C5 ]-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.

KEYWORDS:

Streptomyces; biosynthesis; methylenomycin; natural products; xanthocidin

PMID:
30300957
DOI:
10.1002/cbic.201800467

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