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Synthesis and Biological Evaluation of the Novel Growth Inhibitor Streptol Glucoside, Isolated from an Obligate Plant Symbiont.

Authors
  • Hsiao, Chien-Chi1
  • Sieber, Simon1
  • Georgiou, Antri2
  • Bailly, Aurélien2
  • Emmanouilidou, Despina1
  • Carlier, Aurélien2
  • Eberl, Leo2
  • Gademann, Karl1
  • 1 Department of Chemistry, University of Zürich, Winterthurerstrasse 190, 8057, Zurich, Switzerland. , (Switzerland)
  • 2 Institute of Plant and Microbial Biology, University of Zürich, Zollikerstrasse 107, 8008, Zürich, Switzerland. , (Switzerland)
Type
Published Article
Journal
Chemistry - A European Journal
Publisher
Wiley (John Wiley & Sons)
Publication Date
Feb 01, 2019
Volume
25
Issue
7
Pages
1722–1726
Identifiers
DOI: 10.1002/chem.201805693
PMID: 30508325
Source
Medline
Keywords
Language
English
License
Unknown

Abstract

The plant Psychotria kirkii hosts an obligatory bacterial symbiont, Candidatus Burkholderia kirkii, in nodules on their leaves. Recently, a glucosylated derivative of (+)-streptol, (+)-streptol glucoside, was isolated from the nodulated leaves and was found to possess a plant growth inhibitory activity. To establish a structure-activity relationship study, a convergent strategy was developed to obtain several pseudosugars from a single synthetic precursor. Furthermore, the glucosylation of streptol was investigated in detail and conditions affording specifically the α or β glucosidic anomer were identified. Although (+)-streptol was the most active compound, its concentration in P. kirkii plant leaves extract was approximately ten-fold lower than that of (+)-streptol glucoside. These results provide compelling evidence that the glucosylation of (+)-streptol protects the plant host against the growth inhibitory effect of the compound, which might constitute a molecular cornerstone for this successful plant-bacteria symbiosis. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

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