New branching inhibitors and their potential as strigolactone mimics in rice

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

doi:10.1016/j.bmcl.2011.06.019

Cited by 98 publications

(94 citation statements)

References 25 publications

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“…GR24 binding and the initial phase of GR24 hydrolysis do not induce noticeable conformational changes as the D14 structures in four different states (apo-D14 and D14 bound to GR24, the GR24 covalently bound hydro- information, Figure S4). While the intact GR24 ligand itself appears to provide a surface difference by partially exposing its hydrophobic A-ring, our analysis of other SL analogs suggests that exposure of a hydrophobic group in non-hydrolyzed SL is not required for inducing D14-D3 interaction (Figures 8 and 9) or for SL biological activity [32]. Our results suggest that ligand hydrolysis is required for the ability of GR24 to induce D14-D3 interaction.…”

Section: Discussionmentioning

confidence: 70%

“…Because of GR24's chemical instability and cost of production, new SL analogs that can be easily synthesized would have important agricultural applications. We show here that several of the new compounds that are active in SL signaling [32] can be hydrolyzed by D14 (Supplementary information, Figure S10), can promote D14-D3 (Fig 8A-8B) and DAD2-D3 interactions ( Figure 8B inlet), and destabilize D14 and DAD2 (Supplementary information, Figure S11). In contrast, karrikins and the ABC-ring and D-ring of GR24, which are inactive in SL signaling [25,33,34], failed to promote D14-D3 interaction ( Figure 8B).…”

Section: A Structurally Distinct Class Of Sl Analogs Possesses Similamentioning

confidence: 92%

Section: Chemical Structures Of Gr-24 Br-pmf I-pmf Cn-pmf Br-bmfmentioning

confidence: 99%

“…ABCring, D-ring and other SL mimics were chemically synthesized based on previous published literature [32,[36][37][38]. In brief, for the synthesis of Br-PMF, I-PMF, CN-PMF, and Br-BMF [32], the corresponding phenol was coupled with 5-bromo-3-ethylfuran-2(5H)-one under basic conditions to give the desired products; for the synthesis of the ABC-ring [37], first, the intermediate indanylacetic acid was prepared by using 1-indanone as the starting material. Then, it was reduced in the presence of NaBH 4 and CeCl 3 •7H 2 O, followed by intermolecular esterification to deliver the desired product; the D-ring [38] was synthesized through a Kharasch addition catalyzed by (PCy 3 ) 2 Cl 2 Ru = CHPh and subsequent hydrolysis in 6 M HCl solution; for the synthesis of KAR1 and KAR2 [36], first, commercially available 3-hydroxy-4H-pyran-4-one was treated with phosphorus pentasulphide.…”

Section: Chemical Structures Of Gr-24 Br-pmf I-pmf Cn-pmf Br-bmfmentioning

confidence: 99%

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Destabilization of strigolactone receptor DWARF14 by binding of ligand and E3-ligase signaling effector DWARF3

et al. 2015

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Strigolactones (SLs) are endogenous hormones and exuded signaling molecules in plant responses to low levels of mineral nutrients. Key mediators of the SL signaling pathway in rice include the α/β-fold hydrolase DWARF 14 (D14) and the F-box component DWARF 3 (D3) of the ubiquitin ligase SCF D3 that mediate ligand-dependent degradation of downstream signaling repressors. One perplexing feature is that D14 not only functions as the SL receptor but is also an active enzyme that slowly hydrolyzes diverse natural and synthetic SLs including GR24, preventing the crystallization of a binary complex of D14 with an intact SL as well as the ternary D14/SL/D3 complex. Here we overcome these barriers to derive a structural model of D14 bound to intact GR24 and identify the interface that is required for GR24-mediated D14-D3 interaction. The mode of GR24-mediated signaling, including ligand recognition, hydrolysis by D14, and ligand-mediated D14-D3 interaction, is conserved in structurally diverse SLs. More importantly, D14 is destabilized upon the binding of ligands and D3, thus revealing an unusual mechanism of SL recognition and signaling, in which the hormone, the receptor, and the downstream effectors are systematically destabilized during the signal transduction process.

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Section: Discussionmentioning

confidence: 70%

Section: A Structurally Distinct Class Of Sl Analogs Possesses Similamentioning

confidence: 92%

Section: Chemical Structures Of Gr-24 Br-pmf I-pmf Cn-pmf Br-bmfmentioning

confidence: 99%

Section: Chemical Structures Of Gr-24 Br-pmf I-pmf Cn-pmf Br-bmfmentioning

confidence: 99%

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Destabilization of strigolactone receptor DWARF14 by binding of ligand and E3-ligase signaling effector DWARF3

et al. 2015

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“…SL analogues (compounds 10 À 13; Supplementary Fig. S4a) were prepared according to the previously described reaction 54 . Among them, we synthesized two novel compounds as follows.…”

Section: Methodsmentioning

confidence: 99%

Molecular mechanism of strigolactone perception by DWARF14

et al. 2013

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Strigolactones (SLs) are phytohormones that inhibit shoot branching and function in the rhizospheric communication with symbiotic fungi and parasitic weeds. An a/b-hydrolase protein, DWARF14 (D14), has been recognized to be an essential component of plant SL signalling, although its precise function remains unknown. Here we present the SL-dependent interaction of D14 with a gibberellin signalling repressor SLR1 and a possible mechanism of phytohormone perception in D14-mediated SL signalling. D14 functions as a cleavage enzyme of SLs, and the cleavage reaction induces the interaction with SLR1. The crystal structure of D14 shows that 5-hydroxy-3-methylbutenolide (D-OH), which is a reaction product of SLs, is trapped in the catalytic cavity of D14 to form an altered surface. The D14 residues recognizing D-OH are critical for the SL-dependent D14 À SLR1 interaction. These results provide new insight into crosstalk between gibberellin and SL signalling pathways.

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Chemistry of Strigolactones, Key Players in Plant Communication

Daignan‐Fornier,

Keita,

Boyer

2024

ChemBioChem

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Today, the use of artificial pesticides is questionable and the adaptation to global warming is a necessity. The promotion of favorable natural interactions in the rhizosphere offers interesting perspectives for changing the type of agriculture. Strigolactones (SLs), the latest class of phytohormones to be discovered, are also chemical mediators in the rhizosphere. We present in this review the diversity of natural SLs, their analogs, mimics, and probes essential for the biological studies of this class of compounds. Their biosynthesis and access by organic synthesis are highlighted especially concerning noncanonical SLs, the more recently discovered natural SLs. Organic synthesis of analogs, stable isotope‐labeled standards, mimics, and probes are also reviewed here. In the last part, the knowledge about the SL perception is described as well as the different inhibitors of SL receptors that have been developed.

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New branching inhibitors and their potential as strigolactone mimics in rice

Cited by 98 publications

References 25 publications

Destabilization of strigolactone receptor DWARF14 by binding of ligand and E3-ligase signaling effector DWARF3

Destabilization of strigolactone receptor DWARF14 by binding of ligand and E3-ligase signaling effector DWARF3

Molecular mechanism of strigolactone perception by DWARF14

Chemistry of Strigolactones, Key Players in Plant Communication

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