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Synthesis and biological evaluation of the novel growth inhibitor streptol glucoside, isolated from an obligate plant symbiont

Authors
  • Hsiao, Chien-Chi
  • Sieber, Simon
  • Georgiou, Antri
  • Bailly, Aurélien
  • Emmanouilidou, Despina
  • Carlier, Aurélien
  • Eberl, Leo
  • Gademann, Karl
Publication Date
Jan 01, 2019
Source
Ghent University Institutional Archive
Keywords
Language
English
License
Unknown
External links

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 alpha or beta 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.

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