New branching inhibitors and their potential as strigolactone mimics in rice

Kosuke Fukui, Shinsaku Ito, Kotomi Ueno, Shinjiro Yamaguchi, Junko Kyozuka, Tadao Asami

    Research output: Contribution to journalArticlepeer-review

    70 Citations (Scopus)

    Abstract

    Strigolactones (SLs) are rhizosphere communication chemicals. Recent studies of highly branched mutants revealed that SL or its metabolites work as a phytohormone to inhibit shoot branching. When SLs are exogenously applied to the rice d10-1 mutant that has a highly branched phenotype caused by a defect in the SL biosynthesis gene (CCD8), they inhibit tiller bud outgrowth (branching in rice) of the mutant. We focused our attention on the SL function as a phytohormone and tried to find new chemicals mimicking the hormonal action of SL by screening chemicals that inhibit branching of rice d10-1 mutant. Fortunately, we found 5-(4-chlorophenoxy)-3-methylfuran-2(5H)-one (3a) as a new chemical possessing SL-like activity against the rice d10-1 mutant. Then, we prepared several derivatives of 3a (3b-3k) to examine their ability to inhibit shoot branching of rice d10-1. These derivatives were synthesized by a one-pot coupling reaction between phenols and halo butenolide to give 5-phenoxy 3-methylfuran-2(5H)-one (3) derivatives, which possess a common substructure with SLs. Some of the derivatives showed SL-like activity more potently than GR24, a typical SL derivative, in a rice assay. As SLs also show activity by inducing seed germination of root parasitic plants, the induction activity of these derivatives was also evaluated. Here we report the structure-activity relationships of these compounds.

    Original languageEnglish
    Pages (from-to)4905-4908
    Number of pages4
    JournalBioorganic and Medicinal Chemistry Letters
    Volume21
    Issue number16
    DOIs
    Publication statusPublished - 2011 Aug 15

    Keywords

    • Branching
    • Chemical synthesis
    • Drug design
    • Germination
    • Mimic
    • Plant hormone
    • Root parasitic weed
    • Strigolactone

    ASJC Scopus subject areas

    • Biochemistry
    • Molecular Medicine
    • Molecular Biology
    • Pharmaceutical Science
    • Drug Discovery
    • Clinical Biochemistry
    • Organic Chemistry

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