New strigolactone mimics: structure-activity relationship and mode of action as germinating stimulants for parasitic weeds.

B. Zwanenburg, S.K. Nayak, T. Charnikhova, H.J. Bouwmeester

Research output: Contribution to journalArticleAcademicpeer-review

32 Citations (Scopus)

Abstract

Strigolactones (SLs) are new plant hormones with varies important bio-functions. This Letter deals with germination of seeds of parasitic weeds. Natural SLs have a too complex structure for synthesis. Therefore, there is an active search for SL analogues and mimics with a simpler structure with retention of activity. SL analogues all contain the D-ring connected with an enone moiety through an enol ether unit. A new mechanism for the hydrolysis SL analogues involving bidentate bound water and an a,ß-hydrolase with a Ser-His-Asp catalytic triad has been proposed. Newly discovered SL mimics only have the D-ring with an appropriate leaving group at C-5. A mode of action for SL mimics was proposed for which now supporting evidence is provided. As predicted an extra methyl group at C-4 of the D-ring blocks the germination of seeds of parasitic weeds.
Original languageEnglish
Pages (from-to)5182-5186
JournalBioorganic and Medicinal Chemistry Letters
Volume23
Issue number18
DOIs
Publication statusPublished - 2013

Keywords

  • seed-germination
  • orobanche-minor
  • plant hormones
  • am fungi
  • striga-hermonthica
  • red-clover
  • analogs
  • inhibition
  • ring
  • phelipanche

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