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The Chemical Structure of Widespread Microbial Aryl Polyene Lipids

Gina L. C. Grammbitter, Yi-Ming Shi, Yan-Ni Shi, Sahithya P. B. Vemulapalli, Christian Richter, Harald Schwalbe, Mohammad Alanjary, Anja Schüffler, Matthias Witt, Christian Griesinger, Helge B. Bode
doi: https://doi.org/10.1101/2020.12.19.423268
Gina L. C. Grammbitter
1Institute of Molecular Biological Science, Johann Wolfgang Goethe University, 60438 Frankfurt, Germany
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Yi-Ming Shi
1Institute of Molecular Biological Science, Johann Wolfgang Goethe University, 60438 Frankfurt, Germany
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Yan-Ni Shi
1Institute of Molecular Biological Science, Johann Wolfgang Goethe University, 60438 Frankfurt, Germany
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Sahithya P. B. Vemulapalli
2Max Planck Institute for Biophysical Chemistry, NMR-based Structural Biology, 37077 Göttingen, Germany
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Christian Richter
3Institute for Organic Chemistry and Chemical Biology, Center for Biomolecular Magnetic Resonance, Johann Wolfgang Goethe University, 60439 Frankfurt am Main, Germany
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Harald Schwalbe
3Institute for Organic Chemistry and Chemical Biology, Center for Biomolecular Magnetic Resonance, Johann Wolfgang Goethe University, 60439 Frankfurt am Main, Germany
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Mohammad Alanjary
1Institute of Molecular Biological Science, Johann Wolfgang Goethe University, 60438 Frankfurt, Germany
4Bioinformatics Group, Wageningen University, Droevendaalsesteeg 1, 6708PB Wageningen, Netherlands
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Anja Schüffler
5University of Kaiserslautern, Paul-Ehrlich-Str. 23, 67663 Kaiserslautern, Germany
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Matthias Witt
6Bruker Daltonik GmbH, Fahrenheitstrasse 4, 28359 Bremen, Germany
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Christian Griesinger
2Max Planck Institute for Biophysical Chemistry, NMR-based Structural Biology, 37077 Göttingen, Germany
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Helge B. Bode
1Institute of Molecular Biological Science, Johann Wolfgang Goethe University, 60438 Frankfurt, Germany
7Senckenberg Gesellschaft für Naturforschung, Frankfurt am Main, 60325, Germany
8Buchmann Institute for Molecular Life Sciences (BMLS), Johann Wolfgang Goethe University, Max-von-Laue-Straße 15, 60438 Frankfurt am Main, Germany
9Max-Planck-Institute for Terrestrial Microbiology, Department of Natural Products in Organismic Interactions, 35043 Marburg, Germany
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  • For correspondence: helge.bode@mpi-marburg.mpg.de
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Abstract

Biosynthetic gene clusters (BGC) involved in aryl polyene (APE) biosynthesis are supposed to represent the most widespread BGC in the bacterial world.[1–3] Still, only hydrolysis products[4–8] and not the full-length product(s) have been identified, hindering studies on their biosynthesis and natural function. Here, we apply subsequent chromatographic separations to purify the aryl polyene-containing lipids (APELs) from the entomopathogenic bacterium Xenorhabdus doucetiae. Structure elucidation using a combination of isotope labeling, nuclear magnetic resonance techniques, and tandem mass spectrometry reveals an array of APELs featuring an all-trans C26:5 conjugated fatty acyl and a galactosamine-phosphate-glycerol moiety. In combination with extensive genetic studies, this research broadens the bacterial natural product repertoire and paves the way for future functional characterization of this almost universal microbial compound class. Due to their protective function against reactive oxygen species,[5,9] APELs might be important for virulence or symbiosis, mediating organismic interactions in several ecological niches.

Competing Interest Statement

The authors have declared no competing interest.

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Posted December 20, 2020.
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The Chemical Structure of Widespread Microbial Aryl Polyene Lipids
Gina L. C. Grammbitter, Yi-Ming Shi, Yan-Ni Shi, Sahithya P. B. Vemulapalli, Christian Richter, Harald Schwalbe, Mohammad Alanjary, Anja Schüffler, Matthias Witt, Christian Griesinger, Helge B. Bode
bioRxiv 2020.12.19.423268; doi: https://doi.org/10.1101/2020.12.19.423268
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The Chemical Structure of Widespread Microbial Aryl Polyene Lipids
Gina L. C. Grammbitter, Yi-Ming Shi, Yan-Ni Shi, Sahithya P. B. Vemulapalli, Christian Richter, Harald Schwalbe, Mohammad Alanjary, Anja Schüffler, Matthias Witt, Christian Griesinger, Helge B. Bode
bioRxiv 2020.12.19.423268; doi: https://doi.org/10.1101/2020.12.19.423268

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