Journal Article

Strigolactone Analogs Derived from Ketones Using a Working Model for Germination Stimulants as a Blueprint

Alinanuswe S. Mwakaboko and Binne Zwanenburg

in Plant and Cell Physiology

Published on behalf of Japanese Society of Plant Physiologists

Volume 52, issue 4, pages 699-715
Published in print April 2011 | ISSN: 0032-0781
Published online March 2011 | e-ISSN: 1471-9053 | DOI: https://dx.doi.org/10.1093/pcp/pcr031
Strigolactone Analogs Derived from Ketones Using a Working Model for Germination Stimulants as a Blueprint

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  • Biochemistry
  • Molecular and Cell Biology
  • Plant Sciences and Forestry

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Strigolactones are important signaling compounds in the plant kingdom. Here we focus on their germination stimulatory effect on seeds of the parasitic weeds Striga and Orobanche spp. and more particularly on the design and synthesis of new active strigolactone analogs derived from simple cyclic ketones. New analogs derived from 1-indanone, 1-tetralone, cyclopentanone, cyclohexanone and a series of substituted cyclohexanones (including carvone and pulegone) are prepared by formylation of the ketones with ethyl formate followed by coupling with a halo butenolide. Both enantiomers of the analog derived from 1-tetralone have been prepared by employing a homochiral synthon for the coupling reaction. For three other strigolactone analogs the antipodes have been obtained by chromatography on a chiral column. All analogs have an appreciable germinating activity towards seeds of Striga hermomonthica and Orobanche crenata and O. cernua. Stereoisomers having the same configuration at the D-ring as in naturally occurring strigol have a higher stimulatory effect than the corresponding antipodes. The analogs obtained from 1-indanone and 1-tetralone have an activity comparable with that of the well known stimulant GR 24. Analogs derived from 2-phenyl-cylohexanone, carvone and pulegone also have a good germinating response. The results show that the working model for designing new bioactive strigolactones is applicable.

Keywords: Bioassay; Germination stimulant; Parasitic weeds; Strigolactones; Structure–activity relationship; Synthesis

Journal Article.  11448 words.  Illustrated.

Subjects: Biochemistry ; Molecular and Cell Biology ; Plant Sciences and Forestry

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