Premium
Synthesis and Biological Evaluation of the Novel Growth Inhibitor Streptol Glucoside, Isolated from an Obligate Plant Symbiont
Author(s) -
Hsiao ChienChi,
Sieber Simon,
Georgiou Antri,
Bailly Aurélien,
Emmanouilidou Despina,
Carlier Aurélien,
Eberl Leo,
Gademann Karl
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201805693
Subject(s) - glucoside , biology , symbiosis , bacteria , plant growth , botany , obligate , host (biology) , microbiology and biotechnology , medicine , alternative medicine , pathology , genetics , ecology
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.