10.1002/chem.201805693
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Figure 2. Phenotype of lettuce seedlings after 5 days of compound treatment
at 25 µM concentration. Root growth and development are altered in
decreasing activity: (+)-streptol (3) > (+)-streptol glucoside (2) > A-79197-2 (4)
and 5, 6 and 7 showed no activity. Scale = 5 mm.
In conclusion, we developed a convergent synthetic route
producing three natural products and their enantiomer or
diastereoisomer form. The plant growth inhibitory activity of
these compounds has been evaluated and (+)-streptol was
found to possess the most potent activity, (+)-streptol glucoside
and A-79197-2, which are produced by different plant-
associated bacteria, were found to be less active than
(+)-streptol. We suggest that the glucosylation of (+)-streptol is
required to reduce the toxicity of the compound for the host plant
and we are currently investigating this hypothesis.
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We gratefully acknowledge the Swiss National Science
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Keywords: streptol glucoside • A-79197-2 • streptol • Psychotria
kirkii • glucosylation
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