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

  • Hsiao, Chien-Chi
  • Sieber, Simon
  • Georgiou, Antri
  • Bailly, Aurélien
  • Emmanouilidou, Despina
  • Carlier, Aurélien
  • Eberl, Leo
  • Gademann, Karl
Publication Date
Jan 01, 2019
Ghent University Institutional Archive
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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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