95 results on '"François-Didier, Boyer"'
Search Results
2. Physcomitrium patensSMXL homologs are PpMAX2-dependent negative regulators of growth
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Ambre Guillory, Mauricio Lopez-Obando, Khalissa Bouchenine, Philippe Le Bris, Alain Lécureuil, Jean-Paul Pillot, Vincent Steinmetz, François-Didier Boyer, Catherine Rameau, Alexandre de Saint Germain, and Sandrine Bonhomme
- Abstract
SMXL proteins are a plant-specific clade of type I HSP100/Clp-ATPases.SMXLgenes are found in virtually all land plants’ genomes. However, they have mainly been studied in angiosperms. InArabidopsis thaliana, three SMXL functional subclades have been identified: SMAX1/SMXL2, SMXL345 and SMXL678. Out of these, two subclades ensure transduction on endogenous hormone signals: SMAX1/SMXL2 are involved in KAI2-ligand (KL) signaling, while SMXL678 are involved in strigolactones (SLs) signaling. Many questions remain regarding the mode of action of these proteins, as well as their ancestral role. In light of recent discoveries in the liverwortMarchantia polymorpha,we addressed this second question by investigating the function of the fourSMXLgenes of the mossPhyscomitrium patens.We demonstrate that PpSMXL proteins are negative regulators of growth, involved in the likely conserved ancestral MAX2-dependent KL signaling pathway. However, PpSMXL proteins expressed inArabidopsis thalianaunexpectedly cannot replace SMAX1/SMXL2 function in KL signaling, whereas they can functionally replace SMXL4/5 and restore root growth. Therefore, the molecular function of SMXL could be conserved, but not their interaction network. Moreover, one PpSMXL clade also positively regulates transduction of the SL signal inP. patens, this function most probably having an independent evolutionary origin to angiosperms SMXL678.
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- 2023
3. A structural homologue of the plant receptor D14 mediates responses to strigolactones in the fungal phytopathogen Cryphonectria parasitica
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Valentina Fiorilli, Marco Forgia, Alexandre Saint Germain, Giulia D’Arrigo, David Cornu, Philippe Le Bris, Salim Al‐Babili, Francesca Cardinale, Cristina Prandi, Francesca Spyrakis, François‐Didier Boyer, Massimo Turina, Luisa Lanfranco, Dipartimento di Scienze della Vita e Biologia dei Sistemi, Università degli studi di Torino = University of Turin (UNITO), CNR Istituto per la Protezione Sostenibile delle Piante [Torino, Italia] (IPSP), National Research Council of Italy | Consiglio Nazionale delle Ricerche (CNR), Institut Jean-Pierre Bourgin (IJPB), AgroParisTech-Université Paris-Saclay-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), Institut de Biologie Intégrative de la Cellule (I2BC), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), King Abdullah University of Science and Technology (KAUST), Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), CRG2017/King Abdullah University of Science and TechnologyEuropean CommissionUniversità degli Studi di Torinoshort-term mobility COST fellowship (COST Action)FA 1206Infrastructures en Biologie Sante et AgronomieRegion Ile-de-FrancePlan Cancer, ANR-11-LABX-0039,CHARMMMAT,CHimie des ARchitectures MoléculairesMultifonctionnelles et des MATériaux(2011), and ANR-17-EURE-0007,SPS-GSR,Ecole Universitaire de Recherche de Sciences des Plantes de Paris-Saclay(2017)
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integumentary system ,Physiology ,fungi ,fungus ,strigolactones ,Plant Science ,perception ,[SDV.BV.PEP]Life Sciences [q-bio]/Vegetal Biology/Phytopathology and phytopharmacy ,apocarotenoids ,Lactones ,Ascomycota ,Plant Growth Regulators ,α/β-hydrolase, apocarotenoids, Cryphonectria parasitica, D14, fungus, perception, strigolactones ,D14 ,α/β-hydrolase ,Heterocyclic Compounds, 3-Ring ,Cryphonectria parasitica ,[SDV.MP.MYC]Life Sciences [q-bio]/Microbiology and Parasitology/Mycology ,Plant Proteins - Abstract
International audience; Strigolactones (SLs) are plant hormones and important signaling molecules required to promote the arbuscular mycorrhizal (AM) symbiosis. While in plants an α/β-hydrolase, DWARF14 (D14), was shown to act as a receptor that binds and cleaves SLs, the fungal receptor for SLs is unknown.Since AM fungi are currently not genetically tractable, in this study, we used the fungal pathogen Cryphonectria parasitica for which gene deletion protocols exist, as a model, as we have previously shown that it responds to SLs. By means of computational, biochemical and genetic analyses we identified a D14 structural homologue, CpD14.Molecular homology modelling and docking support the prediction that CpD14 interacts with and hydrolyses SLs. The recombinant CpD14 protein shows α/β hydrolytic activity in vitro against the SLs synthetic analogue GR24; its enzymatic activity requires an intact Ser/His/Asp catalytic triad. CpD14 expression in the d14-1 loss-of-function Arabidopsis thaliana line did not rescue the plant mutant phenotype. However, gene inactivation by knock-out homologous recombination reduced fungal sensitivity to SLs.These results indicate that CpD14 is involved in SLs responses in C. parasitica and strengthen the role of SLs as multifunctional molecules acting in plant microbe-interactions.
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- 2022
4. Structural and functional analyses explain Pea KAI2 receptor diversity and reveal stereoselective catalysis during signal perception
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David Cornu, François-Didier Boyer, Angelica M. Guercio, Nitzan Shabek, Alexandre de Saint Germain, Philippe Le Bris, Abdelhafid Bendahmane, Caroline Gutjahr, Salar Torabi, Catherine Rameau, Christine Le Signor, Marion Dalmais, Jean-Paul Pillot, Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), University of California [Davis] (UC Davis), University of California (UC), Technische Universität Munchen - Université Technique de Munich [Munich, Allemagne] (TUM), Institut de Biologie Intégrative de la Cellule (I2BC), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), Institut des Sciences des Plantes de Paris-Saclay (IPS2 (UMR_9213 / UMR_1403)), Université d'Évry-Val-d'Essonne (UEVE)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Université Paris Cité (UPCité)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), Agroécologie [Dijon], Université de Bourgogne (UB)-AgroSup Dijon - Institut National Supérieur des Sciences Agronomiques, de l'Alimentation et de l'Environnement-Université Bourgogne Franche-Comté [COMUE] (UBFC)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), Institut Jean-Pierre Bourgin (IJPB), AgroParisTech-Université Paris-Saclay-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), and 2047396/National Science Foundation (NSF)2028283/National Science Foundation (NSF)
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0106 biological sciences ,QH301-705.5 ,[SDV]Life Sciences [q-bio] ,Arabidopsis ,Strigolactone ,Medicine (miscellaneous) ,01 natural sciences ,General Biochemistry, Genetics and Molecular Biology ,Catalysis ,Serine ,03 medical and health sciences ,Plant Growth Regulators ,Hydrolase ,[SDV.BV]Life Sciences [q-bio]/Vegetal Biology ,[SDV.BBM.BC]Life Sciences [q-bio]/Biochemistry, Molecular Biology/Biochemistry [q-bio.BM] ,Biology (General) ,Receptor ,Histidine ,030304 developmental biology ,Butenolide ,0303 health sciences ,[SDV.BBM.BS]Life Sciences [q-bio]/Biochemistry, Molecular Biology/Structural Biology [q-bio.BM] ,Chemistry ,Arabidopsis Proteins ,Peas ,food and beverages ,[SDV.BV.BOT]Life Sciences [q-bio]/Vegetal Biology/Botanics ,Ligand (biochemistry) ,Biochemistry ,Perception ,Signal transduction ,General Agricultural and Biological Sciences ,010606 plant biology & botany - Abstract
KAI2 are plant α/β hydrolase receptors, which perceive smoke-derived butenolide signals (karrikins) and putative endogenous, yet unidentified phytohormones (KAI2-ligands, KLs). The number of functional KAI2 receptors varies among plant species. It has been suggested that KAI2 gene duplication and sub-functionalization plays an adaptative role for diverse environments or ligand diversification by altering the receptor responsiveness to specific KLs. Legumes represent one of the largest families of flowering plants and contain many essential agronomic crops. Prior to legume diversification, KAI2 underwent duplication, resulting in KAI2A and KAI2B. Integrating plant genetics, ligand perception and enzymatic assays, and protein crystallography, we demonstrate that Pisum sativum KAI2A and KAI2B act as receptors and enzymes with divergent ligand stereoselectivity. KAI2B has a stronger affinity than KAI2A towards the KAI2-ligand (-)-GR24 and remarkably hydrolyses a broader range of substrates including the strigolactone-like isomer (+)-GR24. We determine the crystal structures of PsKAI2B in apo and butenolide-bound states. The biochemical and structural analyses as well as recorded mass spectra of KAI2s reveal a transient intermediate on the catalytic serine and a stable adduct on the catalytic histidine, further illuminating the role of KAI2 not only as receptors but also as bona fide enzymes. Our work uncovers the stereoselectivity of ligand perception and catalysis by evolutionarily diverged KAI2 receptors in KAR/KL signaling pathways and proposes adaptive sensitivity to KAR/KL and strigolactone phytohormones by KAI2B.
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- 2022
5. Noncanonical Strigolactone Analogues Highlight Selectivity for Stimulating Germination in Two
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Suzanne Daignan, Fornier, Alexandre, de Saint Germain, Pascal, Retailleau, Jean-Paul, Pillot, Quentin, Taulera, Lucile, Andna, Laurence, Miesch, Soizic, Rochange, Jean-Bernard, Pouvreau, and François-Didier, Boyer
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Lactones ,Orobanchaceae ,Orobanche ,Mycorrhizae ,Seeds ,Arabidopsis ,Plant Weeds ,Germination ,Striga ,Heterocyclic Compounds, 3-Ring ,Plant Roots - Abstract
Strigolactones (SLs) are plant hormones exuded in the rhizosphere with a signaling role for the development of arbuscular mycorrhizal (AM) fungi and as stimulants of seed germination of the parasitic weeds
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- 2022
6. MAX2-dependent competence for callus formation and shoot regeneration from Arabidopsis thaliana root explants
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Arne Temmerman, Belen Marquez-Garcia, Stephen Depuydt, Silvia Bruznican, Carolien De Cuyper, Annick De Keyser, François-Didier Boyer, Danny Vereecke, Sylwia Struk, and Sofie Goormachtig
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cell division ,MAX2 ,GENES ,Cytokinins ,Physiology ,Arabidopsis ,pericycle ,Plant Science ,AUXIN ,callus initiation ,Ligands ,Plant Roots ,MEDIATED TRANSFORMATION ,Gene Expression Regulation, Plant ,CYTOKININ ,ACTS ,KAI2 ,ACQUIRING COMPETENCE ,STRIGOLACTONE ANALOG GR24 ,PERCEPTION ,shoot regeneration ,Indoleacetic Acids ,Arabidopsis Proteins ,Biology and Life Sciences ,LATERAL ROOTS ,GERMINATION - Abstract
MAX2 signalling confers competence to root explants for callus formation and shoot regeneration. Transcriptome analysis of max2reveals misregulation of LBDand light-responsive genes early in incubation on callus-inducing medium. Although the division of the pericycle cells initiates both lateral root development and root-derived callus formation, these developmental processes are affected differently in the strigolactone and karrikin/KARRIKIN INSENSITIVE 2 (KAI2) ligand signalling mutant more axillary growth 2 (max2). Whereas max2 produces more lateral roots than the wild type, it is defective in the regeneration of shoots from root explants. We suggest that the decreased shoot regeneration of max2 originates from delayed formation of callus primordium, yielding less callus material to regenerate shoots. Indeed, when incubated on callus-inducing medium, the pericycle cell division was reduced in max2 and the early gene expression varied when compared with the wild type, as determined by a transcriptomics analysis. Furthermore, the expression of the LATERAL ORGAN BOUNDARIES DOMAIN genes and of callus-induction genes was modified in correlation with the max2 phenotype, suggesting a role for MAX2 in the regulation of the interplay between cytokinin, auxin, and light signalling in callus initiation. Additionally, we found that the in vitro shoot regeneration phenotype of max2 might be caused by a defect in KAI2, rather than in DWARF14, signalling. Nevertheless, the shoot regeneration assays revealed that the strigolactone biosynthesis mutants max3 and max4 also play a minor role.
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- 2022
7. Novel non-canonical strigolactone analogs highlight selectivity for stimulating germination in two Phelipanche ramosa populations
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Suzanne Daignan Fornier, Alexandre de Saint Germain, Pascal Retailleau, Jean-Paul Pillot, Quentin Taulera, Lucile Andna, Laurence Miesch, Soizic Rochange, Jean-Bernard Pouvreau, and François-Didier Boyer
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fungi ,food and beverages - Abstract
Strigolactones (SLs) are plant hormones exuded in the rhizosphere with a signaling role for the development of arbuscular mycorrhizal (AM) fungi and as stimulants of seed germination of the parasitic weeds Orobanche, Phelipanche and Striga, the most threatening weeds of major crops worldwide. Phelipanche ramosa is present mainly on rape, hemp and tobacco. P. ramosa 2a preferentially attacks hemp while P. ramosa 1 attacks rapeseed. The recently isolated Cannalactone 14 from hemp root exudates has been characterized as a non-canonical SL that selectively stimulates the germination of P. ramosa 2a seeds in comparison with P. ramosa 1. In the present work, we established that (−)-solanacol 5, a canonical orobanchol-type SL exuded by tobacco and tomato, possesses a remarkable selective germination stimulant activity for P. ramosa 2a seeds. We synthesized cannalactone analogs, named (±)-SdL19 and (±)-SdL118 which have an unsaturated acyclic carbon chain with a tertiary hydroxyl group and a methyl or a cyclopropyl group instead of a cyclohexane A-ring, respectively. (±)-SdL analogs are able to selectively stimulate P. ramosa 2a revealing that these minimal structural elements are key for this selective bioactivity. In addition, we showed that (±)-SdL19 is able to inhibit shoot branching in Pisum sativum and Arabidopsis thaliana, and induces hyphal branching in AM fungus R. irregularis, like SLs.
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- 2022
8. Expansion of the Strigolactone Profluorescent Probes Repertory: The Right Probe for the Right Application
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Alexandre de Saint Germain, Guillaume Clavé, Paul Schouveiler, Jean-Paul Pillot, Abhay-Veer Singh, Arnaud Chevalier, Suzanne Daignan Fornier, Ambre Guillory, Sandrine Bonhomme, Catherine Rameau, François-Didier Boyer, Institut Jean-Pierre Bourgin (IJPB), AgroParisTech-Université Paris-Saclay-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), The CHARM3AT LabEx program (ANR-11-LABX-39) is also acknowledged for its support., ANR-12-BSV6-0004,StrigoPath,Voies de signalisation des strigolactones (et/ou de dérivés) chez les plantes terrestres(2012), ANR-21-CE20-0026,STIGO,Contrôle de l'orobanche du tournesol: identification des stimulants de germination chez l'hôte et récepteur(s) chez l'orobanche(2021), ANR-17-EURE-0007,SPS-GSR,Ecole Universitaire de Recherche de Sciences des Plantes de Paris-Saclay(2017), ANR-05-BDIV-0006,NiceFigs,Nouvelles recherches sur l'écologie des communautés : apports du modèle Ficus(2005), and European Project: 267196,EC:FP7:PEOPLE,FP7-PEOPLE-2010-COFUND,AGREENSKILLS(2012)
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Arabidopsis thaliana ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,structure-activity relationship ,pea ,Physcomitrium patens ,profluorescent probes ,food and beverages ,Plant Science ,strigolactone ,plant hormone ,[SDV.BV.BOT]Life Sciences [q-bio]/Vegetal Biology/Botanics ,[SDV.BBM.BC]Life Sciences [q-bio]/Biochemistry, Molecular Biology/Biochemistry [q-bio.BM] ,α/β-hydrolases - Abstract
Strigolactones (SLs) are intriguing phytohormones that not only regulate plant development and architecture but also interact with other organisms in the rhizosphere as root parasitic plants (Striga, Orobanche, and Phelipanche) and arbuscular mycorrhizal fungi. Starting with a pioneering work in 2003 for the isolation and identification of the SL receptor in parasitic weeds, fluorescence labeling of analogs has proven a major strategy to gain knowledge in SL perception and signaling. Here, we present novel chemical tools for understanding the SL perception based on the enzymatic properties of SL receptors. We designed different profluorescent SL Guillaume Clavé (GC) probes and performed structure-activity relationship studies on pea, Arabidopsis thaliana, and Physcomitrium (formerly Physcomitrella) patens. The binding of the GC probes to PsD14/RMS3, AtD14, and OsD14 proteins was tested. We demonstrated that coumarin-based profluorescent probes were highly bioactive and well-adapted to dissect the enzymatic properties of SL receptors in pea and a resorufin profluorescent probe in moss, contrary to the commercially available fluorescein profluorescent probe, Yoshimulactone Green (YLG). These probes offer novel opportunities for the studies of SL in various plants.
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- 2022
9. Three mutations repurpose a plant karrikin receptor to a strigolactone receptor
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Zhenhua Xu, François-Didier Boyer, James Michael Bradley, Alexandre de Saint Germain, Stefan Schuetz, Peter McCourt, Michael Bunsick, Peter J. Stogios, Shigeo Toh, Shelley Lumba, Hayley E McKay, Hasan Al Galib, Claresta Adityani, Amir Alam Arellano-Saab, Asrinus Subha, Wenda Zhao, Christopher S. P. McErlean, Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), and Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)
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0106 biological sciences ,Hydrolases ,Transgene ,[SDV]Life Sciences [q-bio] ,Arabidopsis ,Strigolactone ,01 natural sciences ,03 medical and health sciences ,Lactones ,Plant Growth Regulators ,Gene Expression Regulation, Plant ,[SDV.BV]Life Sciences [q-bio]/Vegetal Biology ,Receptor ,Furans ,Phylogeny ,030304 developmental biology ,Pyrans ,0303 health sciences ,Multidisciplinary ,biology ,Arabidopsis Proteins ,fungi ,food and beverages ,Biological Sciences ,biology.organism_classification ,Directed evolution ,Karrikin ,Cell biology ,Hormone receptor ,Mutation ,Plant hormone ,Heterocyclic Compounds, 3-Ring ,Function (biology) ,010606 plant biology & botany ,Protein Binding - Abstract
International audience; Uncovering the basis of small molecule hormone receptors evolution is paramount to a complete understanding of how protein structure drives function. In plants, hormone receptors for strigolactones are well suited to evolutionary inquires because closely related homologs have different ligand preferences. More importantly, because of facile plant transgenic systems, receptors can be swapped and quickly assessed functionally in vivo. Here, we show only three mutations are required to switch the non-strigolactone receptor, KAI2, into a strigolactone receptor. This modified receptor still perceives KAI2 ligands and does not require receptor hydrolysis for activity. Structural and molecular dynamic modeling suggest receptor pocket flexibility is important for ligand specificity and downstream signaling partner affinity. These findings indicate a few keystone mutations link strigolactone signaling to germination, which explains how parasitic plants that devastate African agriculture evolved SL receptors to sense the presence of a host plant.
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- 2021
10. Synthesis of Profluorescent Strigolactone Probes for Biochemical Studies
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Alexandre, de Saint Germain, Guillaume, Clavé, and François-Didier, Boyer
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Lactones ,Plant Growth Regulators ,Arabidopsis Proteins ,Luminescent Measurements ,Arabidopsis ,Biological Assay ,Receptors, Cell Surface ,Heterocyclic Compounds, 3-Ring ,Fluorescent Dyes ,High-Throughput Screening Assays ,Signal Transduction - Abstract
In this chapter, we will describe a method we set up to synthesize two profluorescent strigolactone (SL) mimic probes (GC240 and GC242) and the optimized protocols developed to study the enzymatic properties of various strigolactone receptors. The Arabidopsis AtD14 SL receptor is used here as a model for this purpose.
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- 2021
11. Transcriptional Analysis in the Arabidopsis Roots Reveals New Regulators that Link rac-GR24 Treatment with Changes in Flavonol Accumulation, Root Hair Elongation and Lateral Root Density
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Sofie Goormachtig, Stan Van Praet, Carolien De Cuyper, Sylwia Magdalena Struk, Kris Gevaert, Alan Walton, Jiří Friml, Nick Vangheluwe, Cedrick Matthys, Tom Beeckman, Elisabeth Stes, Lingxiang Jiang, Pawel Radoslaw Baster, François-Didier Boyer, and Lukas Braem
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Flavonols ,Genotype ,Physiology ,Mutant ,Arabidopsis ,Strigolactone ,Plant Science ,Root hair elongation ,Genes, Plant ,Plant Roots ,Organogenesis, Plant ,Gene Expression Regulation, Plant ,Transcription factor ,biology ,Chemistry ,Gene Expression Profiling ,Lateral root ,Wild type ,Genetic Variation ,Cell Biology ,General Medicine ,biology.organism_classification ,Karrikin ,Cell biology ,Signal Transduction - Abstract
The synthetic strigolactone (SL) analog, rac-GR24, has been instrumental in studying the role of SLs as well as karrikins because it activates the receptors DWARF14 (D14) and KARRIKIN INSENSITIVE 2 (KAI2) of their signaling pathways, respectively. Treatment with rac-GR24 modifies the root architecture at different levels, such as decreasing the lateral root density (LRD), while promoting root hair elongation or flavonol accumulation. Previously, we have shown that the flavonol biosynthesis is transcriptionally activated in the root by rac-GR24 treatment, but, thus far, the molecular players involved in that response have remained unknown. To get an in-depth insight into the changes that occur after the compound is perceived by the roots, we compared the root transcriptomes of the wild type and the more axillary growth2 (max2) mutant, affected in both SL and karrikin signaling pathways, with and without rac-GR24 treatment. Quantitative reverse transcription (qRT)-PCR, reporter line analysis and mutant phenotyping indicated that the flavonol response and the root hair elongation are controlled by the ELONGATED HYPOCOTYL 5 (HY5) and MYB12 transcription factors, but HY5, in contrast to MYB12, affects the LRD as well. Furthermore, we identified the transcription factors TARGET OF MONOPTEROS 5 (TMO5) and TMO5 LIKE1 as negative and the Mediator complex as positive regulators of the rac-GR24 effect on LRD. Altogether, hereby, we get closer toward understanding the molecular mechanisms that underlay the rac-GR24 responses in the root.
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- 2021
12. A Phelipanche ramosa KAI2 protein perceives strigolactones and isothiocyanates enzymatically
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Anse Jacobs, Lukas Braem, Vincent Steinmetz, Jean-Bernard Pouvreau, Guillaume Clavé, Guillaume Brun, Vincent Servajean, Sofie Goormachtig, François-Didier Boyer, Alexandre de Saint Germain, Philippe Delavault, Philippe Simier, Susann Wicke, Emmanuelle Baudu, David Cornu, Kris Gevaert, Institut Jean-Pierre Bourgin (IJPB), AgroParisTech-Université Paris-Saclay-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), Department of Plant Systems Biology, VIB, and Department of Plant Biotechnology and Bioinformatics, Universiteit Gent = Ghent University [Belgium] (UGENT), Laboratoire de Physiologie et Biotechnologies Végétales (LPBV), Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), Laboratoire de biologie et pathologie végétales (LBPV), Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST), Université de Nantes (UN)-Université de Nantes (UN), Humboldt-Universität zu Berlin, Institute for Integrative Biology of the Cell [Gif-sur-Yvette] (I2BC), Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), Department of Biomolecular Medicine, Institut Jean-Pierre Bourgin's Plant Observatory technological platforms, Paris-Sud University, AgreenSkills award from the European Union, FWO 1S15817N VS04418N, Infrastructures en Biologie Sante et Agronomie, Region Ile-de-France, Plan Cancer, Centre National de la Recherche Scientifique (CNRS) European Commission, ANR-11-LABX-0039,CHARMMMAT,CHimie des ARchitectures MoléculairesMultifonctionnelles et des MATériaux(2011), ANR-17-EURE-0007,SPS-GSR,Ecole Universitaire de Recherche de Sciences des Plantes de Paris-Saclay(2017), Universiteit Gent = Ghent University (UGENT), Humboldt University Of Berlin, Institut de Biologie Intégrative de la Cellule (I2BC), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), and Institute for Biology, Humboldt-Universitat zu Berlin, Berlin, Germany.
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0106 biological sciences ,isothiocyanates ,Parasitic plant ,STRIGA ,receptor ,[SDV]Life Sciences [q-bio] ,Stimulation ,Plant Science ,strigolactones ,Biology ,01 natural sciences ,Biochemistry ,a/b-hydrolase ,Phelipanche ramosa ,03 medical and health sciences ,Striga ,Arabidopsis ,DWARF14 ,KARRIKIN ,α/β-hydrolase ,Receptor ,Molecular Biology ,030304 developmental biology ,2. Zero hunger ,HORMONE-RECEPTOR ,0303 health sciences ,PERCEPTION ,ANALOGS ,Obligate ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,food and beverages ,Biology and Life Sciences ,Cell Biology ,SEED-GERMINATION ,biology.organism_classification ,ARABIDOPSIS ,GENE ,seed germination stimulant ,Karrikin ,PARASITIC PLANT ,Weed ,010606 plant biology & botany ,Biotechnology - Abstract
International audience; Phelipanche ramosa is an obligate root-parasitic weed that threatens major crops in central Europe. In order to germinate, it must perceive various structurally divergent host-exuded signals, including isothiocyanates (ITCs) and strigolactones (SLs). However, the receptors involved are still uncharacterized. Here, we identify five putative SL receptors in P. ramosa and show that PrKAI2d3 is involved in the stimulation of seed germination. We demonstrate the high plasticity of PrKAI2d3, which allows it to interact with different chemicals, including ITCs. The SL perception mechanism of PrKAI2d3 is similar to that of endogenous SLs in non-parasitic plants. We provide evidence that PrKAI2d3 enzymatic activity confers hypersensitivity to SLs. Additionally, we demonstrate that methylbutenolide-OH binds PrKAI2d3 and stimulates P. ramosa germination with bioactivity comparable to that of ITCs. This study demonstrates that P. ramosa has extended its signal perception system during evolution, a fact that should be considered for the development of specific and efficient biocontrol methods.
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- 2021
13. Synthesis of Profluorescent Strigolactone Probes for Biochemical Studies
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Guillaume Clavé, François-Didier Boyer, and Alexandre de Saint Germain
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0106 biological sciences ,0301 basic medicine ,biology ,Chemistry ,Strigolactone ,biology.organism_classification ,01 natural sciences ,3. Good health ,03 medical and health sciences ,030104 developmental biology ,Biochemistry ,Arabidopsis ,Receptor ,010606 plant biology & botany - Abstract
In this chapter, we will describe a method we set up to synthesize two profluorescent strigolactone (SL) mimic probes (GC240 and GC242) and the optimized protocols developed to study the enzymatic properties of various strigolactone receptors. The Arabidopsis AtD14 SL receptor is used here as a model for this purpose.
- Published
- 2021
14. Unraveling the MAX2 Protein Network in Arabidopsis thaliana: Identification of the Protein Phosphatase PAPP5 as a Novel MAX2 Interactor
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François-Didier Boyer, Kris Gevaert, Sylwia Magdalena Struk, Alan Walton, Lam Dai Vu, Stephen Depuydt, Lukas Braem, Annick De Keyser, Ive De Smet, Anse Jacobs, Sofie Goormachtig, Carolien De Cuyper, Geert Persiau, Dominique Eeckhout, Geert De Jaeger, Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), Institut Jean-Pierre Bourgin (IJPB), and AgroParisTech-Université Paris-Saclay-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)
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F-BOX PROTEINS ,[SDV]Life Sciences [q-bio] ,Arabidopsis ,HY5, ELONGATED HYPOCOTYL 5 ,SD, synthetic-defined ,TANDEM AFFINITY PURIFICATION ,strigolactones ,F-box protein ,Biochemistry ,Analytical Chemistry ,Bimolecular fluorescence complementation ,SMAX1, SUPPRESSOR OF MAX2 1 ,Phosphoprotein Phosphatases ,Medicine and Health Sciences ,KARRIKIN ,SMXL, SMAX1-LIKE ,COP9, CONSTITUTIVE PHOTOMORPHOGENIC 9 ,0303 health sciences ,biology ,SCF, S-phase kinase-associated protein 1 (Skp1), Cullin-1/CDC53 and F-box protein ,Chemistry ,phosphorylation ,karrikins ,030302 biochemistry & molecular biology ,MAX2, MORE AXILLARY GROWTH 2 ,SL, strigolactone ,CSN, COP9 signalosome ,Nuclear Proteins ,Plants, Genetically Modified ,Karrikin ,Cell biology ,htl-3, hyposensitive to light 3 ,STH7, SALT TOLERANCE HOMOLOG7 ,Phosphorylation ,STRIGOLACTONE ,AP, affinity purification ,DLK2, D14-LIKE2 ,MAX2 ,FDR, false discovery rate ,Immunoprecipitation ,Phosphatase ,seed germination ,Germination ,BiFC, Bimolecular Fluorescent Complementation ,KAI2, KARRIKIN INSENSITIVE 2 ,03 medical and health sciences ,Tobacco ,GS, protein G/streptavidin-binding peptide ,LEAF SENESCENCE ,COP9 signalosome ,Molecular Biology ,SHOOT DEVELOPMENT ,SCF COMPLEX ,030304 developmental biology ,Tandem affinity purification ,TAP, tandem affinity purification ,KAR, karrikin ,RECEPTOR ,Arabidopsis Proteins ,Research ,Co-IP, coimmunoprecipitation ,BZS1, bzr1–1D Suppressor 1 ,CHS, CHALCONE SYNTHASE ,Y2H, yeast two-hybrid ,LFQ, label-free quantification ,Biology and Life Sciences ,affinity purification ,KL, KAI2 ligand ,rac-GR24, synthetic strigolactone analog ,D53, DWARF53 ,PAPP5, PHYTOCHROME ASSOCIATED PROTEIN PHOSPHATASE 5 ,PMSF, phenylmethylsulfonyl fluoride ,Seedlings ,SEEDLING DEVELOPMENT ,biology.protein ,D14, DWARF 14 ,Carrier Proteins ,RESPONSES - Abstract
The F-box protein MORE AXILLARY GROWTH 2 (MAX2) is a central component in the signaling cascade of strigolactones (SLs) as well as of the smoke-derived karrikins (KARs) and the so far unknown endogenous KAI2 ligand (KL). The two groups of molecules are involved in overlapping and unique developmental processes, and signal-specific outcomes are attributed to perception by the paralogous α/β-hydrolases DWARF14 (D14) for SL and KARRIKIN INSENSITIVE 2/HYPOSENSITIVE TO LIGHT (KAI2/HTL) for KAR/KL. In addition, depending on which receptor is activated, specific members of the SUPPRESSOR OF MAX2 1 (SMAX1)-LIKE (SMXL) family control KAR/KL and SL responses. As proteins that function in the same signal transduction pathway often occur in large protein complexes, we aimed at discovering new players of the MAX2, D14, and KAI2 protein network by tandem affinity purification in Arabidopsis cell cultures. When using MAX2 as a bait, various proteins were copurified, among which were general components of the Skp1-Cullin-F-box complex and members of the CONSTITUTIVE PHOTOMORPHOGENIC 9 signalosome. Here, we report the identification of a novel interactor of MAX2, a type 5 serine/threonine protein phosphatase, designated PHYTOCHROME-ASSOCIATED PROTEIN PHOSPHATASE 5 (PAPP5). Quantitative affinity purification pointed at PAPP5 as being more present in KAI2 rather than in D14 protein complexes. In agreement, mutant analysis suggests that PAPP5 modulates KAR/KL-dependent seed germination under suboptimal conditions and seedling development. In addition, a phosphopeptide enrichment experiment revealed that PAPP5 might dephosphorylate MAX2 in vivo independently of the synthetic SL analog, rac-GR24. Together, by analyzing the protein complexes to which MAX2, D14, and KAI2 belong, we revealed a new MAX2 interactor, PAPP5, that might act through dephosphorylation of MAX2 to control mainly KAR/KL-related phenotypes and, hence, provide another link with the light pathway., Graphical Abstract, Highlights • TAP revealed PAPP5 as a novel interactor of MAX2. • PAPP5 might act through dephosphorylation of MAX2. • PAPP5 modulates KAI2-controlled responses in seeds and young seedlings. • PAPP5 might be another link between KAR/KL signaling and light., In Brief The F-box protein MAX2 is a central component in the signaling pathway of the phytohormones, strigolactones and smoke-derived karrikins. These molecules are perceived by the related receptors D14 and KAI2, respectively. Here, we used tandem and single affinity purifications to broaden the MAX2, KAI2, and D14 interaction network and identified PAPP5 as a novel player. PAPP5 might act via dephosphorylation of MAX2 to modulate KAI2-dependent seed germination and young seedling phenotypes.
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- 2021
15. The Physcomitrium (Physcomitrella) patens PpKAI2L receptors for strigolactones and related compounds function via MAX2-dependent and independent pathways
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Ambre Guillory, Catherine Rameau, Beate Hoffmann, Sandrine Bonhomme, Jean-Bernard Pouvreau, François-Didier Boyer, Mauricio Lopez-Obando, David Cornu, Philippe Delavault, Alexandre de Saint Germain, Philippe Le Bris, Institut Jean-Pierre Bourgin (IJPB), AgroParisTech-Université Paris-Saclay-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), Swedish University of Agricultural Sciences (SLU), Vedas Recherche et Innovation (Vedas CII), Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), Institut de Biologie Intégrative de la Cellule (I2BC), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), Laboratoire de biologie et pathologie végétales (LBPV), Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST), Université de Nantes (UN)-Université de Nantes (UN), Infrastructures en Biologie Santeet Agronomie grant to SICAPS platform of the Institute for Integrative Biology of the Cell, AgreenSkills award from the European Union in the framework of the MarieCurie FP7 COFUND People Programme, ANR-12-BSV6-0004,StrigoPath,Voies de signalisation des strigolactones (et/ou de dérivés) chez les plantes terrestres(2012), ANR-10-LABX-0040,SPS,Saclay Plant Sciences(2010), and ANR-11-LABX-0039,CHARMMMAT,CHimie des ARchitectures MoléculairesMultifonctionnelles et des MATériaux(2011)
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0106 biological sciences ,Physcomitrella ,Mutant ,Strigolactone ,Plant Science ,Physcomitrella patens ,01 natural sciences ,03 medical and health sciences ,Lactones ,Arabidopsis ,[SDV.BV]Life Sciences [q-bio]/Vegetal Biology ,[SDV.BBM]Life Sciences [q-bio]/Biochemistry, Molecular Biology ,Receptor ,Gene ,Research Articles ,030304 developmental biology ,0303 health sciences ,biology ,Cell Biology ,[SDV.BV.BOT]Life Sciences [q-bio]/Vegetal Biology/Botanics ,biology.organism_classification ,Bryopsida ,Karrikin ,[SDV.BV.PEP]Life Sciences [q-bio]/Vegetal Biology/Phytopathology and phytopharmacy ,Biochemistry ,[SDE.BE]Environmental Sciences/Biodiversity and Ecology ,Heterocyclic Compounds, 3-Ring ,010606 plant biology & botany - Abstract
In angiosperms, the α/β hydrolase DWARF14 (D14), along with the F-box protein MORE AXILLARY GROWTH2 (MAX2), perceives strigolactones (SL) to regulate developmental processes. The key SL biosynthetic enzyme CAROTENOID CLEAVAGE DIOXYGENASE8 (CCD8) is present in the moss Physcomitrium patens, and PpCCD8-derived compounds regulate moss extension. The PpMAX2 homolog is not involved in the SL response, but 13 PpKAI2LIKE (PpKAI2L) genes homologous to the D14 ancestral paralog KARRIKIN INSENSITIVE2 (KAI2) encode candidate SL receptors. In Arabidopsis thaliana, AtKAI2 perceives karrikins and the elusive endogenous KAI2-Ligand (KL). Here, germination assays of the parasitic plant Phelipanche ramosa suggested that PpCCD8-derived compounds are likely noncanonical SLs. (+)-GR24 SL analog is a good mimic for PpCCD8-derived compounds in P. patens, while the effects of its enantiomer (−)-GR24, a KL mimic in angiosperms, are minimal. Interaction and binding assays of seven PpKAI2L proteins pointed to the stereoselectivity toward (−)-GR24 for a single clade of PpKAI2L (eu-KAI2). Enzyme assays highlighted the peculiar behavior of PpKAI2L-H. Phenotypic characterization of Ppkai2l mutants showed that eu-KAI2 genes are not involved in the perception of PpCCD8-derived compounds but act in a PpMAX2-dependent pathway. In contrast, mutations in PpKAI2L-G, and -J genes abolished the response to the (+)-GR24 enantiomer, suggesting that PpKAI2L-G, and -J proteins are receptors for moss SLs.
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- 2021
16. The Physcomitrium (Physcomitrella) patens PpKAI2L receptors for strigolactones and related compounds highlight MAX2 dependent and independent pathways
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Sandrine Bonhomme, Philippe Delavault, François-Didier Boyer, Alexandre de Saint Germain, Catherine Rameau, Ambre Guillory, Beate Hoffmann, Mauricio Lopez-Obando, David Cornu, Philippe Le Bris, Jean-Bernard Pouvreau, Institut de Chimie des Substances Naturelles (ICSN), and Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)
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0106 biological sciences ,0303 health sciences ,biology ,Chemistry ,Physcomitrella ,[SDV]Life Sciences [q-bio] ,Mutant ,Strigolactone ,Physcomitrella patens ,biology.organism_classification ,01 natural sciences ,Karrikin ,03 medical and health sciences ,Biochemistry ,Arabidopsis ,Receptor ,Gene ,030304 developmental biology ,010606 plant biology & botany - Abstract
In flowering plants, the α/β hydrolase DWARF14 (D14) perceives strigolactone (SL) hormones and interacts with the F-box protein MORE AXILLARY GROWTH2 (MAX2) to regulate developmental processes. The key SL biosynthetic enzyme, CAROTENOID CLEAVAGE DEOXYGENASE8 (CCD8), is present in the mossPhyscomitrium (Physcomitrella) patens,and PpCCD8-derived compounds regulate plant extension. Based on germination assays using seeds of the parasitic plantPhelipanche ramosa,we propose that these compounds are non-canonical SLs. Perception of PpCCD8-derived compounds does not require the PpMAX2 homolog. Candidate receptors are among the 13PpKAI2LIKE-A to -Lgenes, homologous to the ancestralD14paralogKARRIKIN INSENSITIVE2 (KAI2).In Arabidopsis, AtKAI2 is the receptor for a still elusive endogenous KAI2-Ligand (KL). We show that inP. patens,among SL analogs, the (+)-GR24 enantiomer is a good mimic for PpCCD8-derived compounds, while the effects of the (-)-GR24 enantiomer, a KL mimic in flowering plants, are opposite. Interaction and binding assays of seven PpKAI2L proteins using pure enantiomers pinpoint at stereoselectivity towards (-)-GR24 for the (A-E) clade. Enzyme assays highlight strong hydrolytic activity of the PpKAI2L-H protein. Moss mutants for allPpKAI2Lgene subclades were obtained and tested for their response to both enantiomers. We show thatPpKAI2L-Ato-Egenes are not involved in PpCCD8-derived compound perception, but act in a PpMAX2-dependant pathway. In contrast, mutations inPpKAI2L-G, and-Jgenes abolish the response to (+)-GR24, suggesting that encoded proteins are receptors for PpCCD8-derived SLs.
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- 2020
17. A
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Alexandre, de Saint Germain, Anse, Jacobs, Guillaume, Brun, Jean-Bernard, Pouvreau, Lukas, Braem, David, Cornu, Guillaume, Clavé, Emmanuelle, Baudu, Vincent, Steinmetz, Vincent, Servajean, Susann, Wicke, Kris, Gevaert, Philippe, Simier, Sofie, Goormachtig, Philippe, Delavault, and François-Didier, Boyer
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isothiocyanates ,Hydrolases ,receptor ,Plant Weeds ,strigolactones ,seed germination stimulant ,Phelipanche ramosa ,Europe ,Lactones ,Orobanchaceae ,Isothiocyanates ,Amino Acid Sequence ,α/β-hydrolase ,Heterocyclic Compounds, 3-Ring ,Sequence Alignment ,Phylogeny ,Plant Proteins ,Research Article - Abstract
Phelipanche ramosa is an obligate root-parasitic weed that threatens major crops in central Europe. In order to germinate, it must perceive various structurally divergent host-exuded signals, including isothiocyanates (ITCs) and strigolactones (SLs). However, the receptors involved are still uncharacterized. Here, we identify five putative SL receptors in P. ramosa and show that PrKAI2d3 is involved in the stimulation of seed germination. We demonstrate the high plasticity of PrKAI2d3, which allows it to interact with different chemicals, including ITCs. The SL perception mechanism of PrKAI2d3 is similar to that of endogenous SLs in non-parasitic plants. We provide evidence that PrKAI2d3 enzymatic activity confers hypersensitivity to SLs. Additionally, we demonstrate that methylbutenolide-OH binds PrKAI2d3 and stimulates P. ramosa germination with bioactivity comparable to that of ITCs. This study demonstrates that P. ramosa has extended its signal perception system during evolution, a fact that should be considered for the development of specific and efficient biocontrol methods., Phelipanche ramosa is an obligate root-parasitic weed that threatens major crops in central Europe. This study reports the identification of a strigolactone receptor in P. ramosa, PrKAI2d3, that is involved in the stimulation of seed germination. The high plasticity of PrKAI2d3 allows it to interact with different chemicals, including isothiocyanates and methylbutenolide-OH.
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- 2020
18. A Phelipanche ramosa KAI2 Protein Perceives enzymatically Strigolactones and Isothiocyanates
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François-Didier Boyer, Philippe Simier, Jean-Bernard Pouvreau, Vincent Steinmetz, Alexandre de Saint Germain, Philippe Delavault, Guillaume Brun, Sofie Goormachtig, Kris Gevaert, Lukas Braem, Susann Wicke, David Cornu, Anse Jacobs, Vincent Servajean, Emmanuelle Baudu, Guillaume Clavé, Institut de Chimie des Substances Naturelles (ICSN), and Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)
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0106 biological sciences ,2. Zero hunger ,0303 health sciences ,Obligate ,[SDV]Life Sciences [q-bio] ,food and beverages ,Stimulation ,Endogeny ,Biology ,01 natural sciences ,03 medical and health sciences ,Phelipanche ramosa ,Signal perception ,Biochemistry ,Germination ,Weed ,Receptor ,030304 developmental biology ,010606 plant biology & botany - Abstract
Phelipanche ramosa is an obligate root-parasitic weed threatening major crops in central Europe. For its germination, it has to perceive various structurally diverging host-exuded signals, including isothiocyanates (ITCs) and strigolactones (SLs). However, the receptors involved are still uncharacterized. Here, we identified five putative SL receptors in P. ramosa, of which PrKAI2d3 is involved in seed germination stimulation. We established the high plasticity of PrKAI2d3, allowing interaction with different chemicals, including ITCs. The SL perception mechanism of PrKAI2d3 is similar to that of endogenous SLs in non-parasitic plants. We provide evidence that the PrKAI2d3 enzymatic activity confers hypersensitivity to SLs. Additionally, we demonstrated that methylbutenolide-OH binds PrKAI2d3 and stimulates P. ramosa germination with a bioactivity comparable to that of ITCs. This study highlights that P. ramosa has extended its signal perception system during evolution, a fact to be considered in the development of specific and efficient biocontrol methods.
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- 2020
19. Initiation of arbuscular mycorrhizal symbiosis involves a novel pathway independent from hyphal branching
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François-Didier Boyer, Katie Martin, Quentin Taulera, Vincent Servajean, Maïna Cadoret, Soizic Rochange, Dominique Lauressergues, Institut de Chimie des Substances Naturelles (ICSN), and Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)
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0106 biological sciences ,Rhizophagus irregularis ,Hypha ,[SDV]Life Sciences [q-bio] ,Hyphae ,Germ tube ,Strigolactone ,Plant Science ,Fungus ,010603 evolutionary biology ,01 natural sciences ,Plant Roots ,Symbiosis ,Mycorrhizae ,Botany ,Genetics ,Glomeromycota ,Molecular Biology ,Ecology, Evolution, Behavior and Systematics ,ComputingMilieux_MISCELLANEOUS ,Butenolide ,biology ,fungi ,General Medicine ,biology.organism_classification ,Arbuscular mycorrhiza ,010606 plant biology & botany - Abstract
The arbuscular mycorrhizal symbiosis is a very common association between plant roots and soil fungi, which greatly contributes to plant nutrition. Root-exuded compounds known as strigolactones act as symbiotic signals stimulating the fungus prior to root colonization. Strigolactones also play an endogenous role in planta as phytohormones and contribute to the regulation of various developmental traits. Structure-activity relationship studies have revealed both similarities and differences between the structural features required for bioactivity in plants and arbuscular mycorrhizal fungi. In the latter case, bioassays usually measured a stimulation of hyphal branching on isolated fungi of the Gigaspora genus, grown in vitro. Here, we extended these investigations with a bioassay that evaluates the bioactivity of strigolactone analogs in a symbiotic situation and the use of the model mycorrhizal fungus Rhizophagus irregularis. Some general structural requirements for bioactivity reported previously for Gigaspora were confirmed. We also tested additional strigolactone analogs bearing modifications on the conserved methylbutenolide ring, a key element of strigolactone perception by plants. A strigolactone analog with an unmethylated butenolide ring could enhance the ability of R. irregularis to colonize host roots. Surprisingly, when applied to the isolated fungus in vitro, this compound stimulated germ tube elongation but inhibited hyphal branching. Therefore, this compound was able to act on the fungal and/or plant partner to facilitate initiation of the arbuscular mycorrhizal symbiosis, independently from hyphal branching and possibly from the strigolactone pathway.
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- 2020
20. Lotus japonicus karrikin receptors display divergent ligand-binding specificities and organ-dependent redundancy
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Elias Bleek, François-Didier Boyer, Mitsuru Shindo, Samy Carbonnel, Michael K. Udvardi, Maximilian Griesmann, Salar Torabi, Trevor L. Wang, Caroline Gutjahr, Yuhong Tang, Stefan Buchka, Mark T. Waters, Veronica Basso, Ludwig-Maximilians-Universität München (LMU), Kyushu University [Fukuoka], Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), John Innes Centre [Norwich], and The University of Western Australia (UWA)
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0106 biological sciences ,Cancer Research ,Fruit and Seed Anatomy ,Hydrolases ,Physiology ,[SDV]Life Sciences [q-bio] ,Arabidopsis ,Plant Science ,QH426-470 ,Ligands ,Plant Genetics ,Plant Reproduction ,Plant Roots ,Biochemistry ,01 natural sciences ,Hypocotyl ,Lactones ,Aromatic Amino Acids ,Plant Growth Regulators ,Gene Expression Regulation, Plant ,Gene Duplication ,Seed Germination ,Plant Genomics ,Arabidopsis thaliana ,Amino Acids ,Receptor ,Phylogeny ,Flowering Plants ,Genetics (clinical) ,Butenolide ,Plant Growth and Development ,Genetics ,Regulation of gene expression ,0303 health sciences ,Organic Compounds ,Plant Anatomy ,Tryptophan ,Eukaryota ,food and beverages ,Genomics ,Plants ,[SDV.BV.BOT]Life Sciences [q-bio]/Vegetal Biology/Botanics ,Legumes ,Ligand (biochemistry) ,ddc ,Karrikin ,Chemistry ,Experimental Organism Systems ,Plant Physiology ,Embryogenesis ,Physical Sciences ,Engineering and Technology ,Heterocyclic Compounds, 3-Ring ,Research Article ,Biotechnology ,Arabidopsis Thaliana ,Lotus japonicus ,Plant Development ,Bioengineering ,Brassica ,Biology ,Research and Analysis Methods ,03 medical and health sciences ,Model Organisms ,Plant and Algal Models ,Phylogenetics ,Hydrolase ,[SDV.BBM]Life Sciences [q-bio]/Biochemistry, Molecular Biology ,Grasses ,Furans ,Molecular Biology ,Ecology, Evolution, Behavior and Systematics ,Pyrans ,030304 developmental biology ,Arabidopsis Proteins ,Plant Embryo Anatomy ,Organic Chemistry ,fungi ,Organisms ,Chemical Compounds ,Biology and Life Sciences ,Proteins ,15. Life on land ,Microarray Analysis ,biology.organism_classification ,Lotus ,Animal Studies ,Plant Biotechnology ,Rice ,Plant Embryogenesis ,Developmental Biology ,010606 plant biology & botany - Abstract
Karrikins (KARs), smoke-derived butenolides, are perceived by the α/β-fold hydrolase KARRIKIN INSENSITIVE2 (KAI2) and thought to mimic endogenous, yet elusive plant hormones tentatively called KAI2-ligands (KLs). The sensitivity to different karrikin types as well as the number of KAI2 paralogs varies among plant species, suggesting diversification and co-evolution of ligand-receptor relationships. We found that the genomes of legumes, comprising a number of important crops with protein-rich, nutritious seed, contain two or more KAI2 copies. We uncover sub-functionalization of the two KAI2 versions in the model legume Lotus japonicus and demonstrate differences in their ability to bind the synthetic ligand GR24ent-5DS in vitro and in genetic assays with Lotus japonicus and the heterologous Arabidopsis thaliana background. These differences can be explained by the exchange of a widely conserved phenylalanine in the binding pocket of KAI2a with a tryptophan in KAI2b, which arose independently in KAI2 proteins of several unrelated angiosperms. Furthermore, two polymorphic residues in the binding pocket are conserved across a number of legumes and may contribute to ligand binding preferences. The diversification of KAI2 binding pockets suggests the occurrence of several different KLs acting in non-fire following plants, or an escape from possible antagonistic exogenous molecules. Unexpectedly, L. japonicus responds to diverse synthetic KAI2-ligands in an organ-specific manner. Hypocotyl growth responds to KAR1, KAR2 and rac-GR24, while root system development responds only to KAR1. This differential responsiveness cannot be explained by receptor-ligand preferences alone, because LjKAI2a is sufficient for karrikin responses in the hypocotyl, while LjKAI2a and LjKAI2b operate redundantly in roots. Instead, it likely reflects differences between plant organs in their ability to transport or metabolise the synthetic KLs. Our findings provide new insights into the evolution and diversity of butenolide ligand-receptor relationships, and open novel research avenues into their ecological significance and the mechanisms controlling developmental responses to divergent KLs., Author summary Plant hormone signaling is crucial for development and for adequate responses to biotic and abiotic environmental conditions. The most recently discovered plant hormone receptor KARRIKIN INSENSITVE 2 (KAI2), binds a small butenolide called karrikin that was discovered in smoke and induces germination of fire-following plants. Several lines of evidence suggest a yet elusive endogenous hormone, which acts as ligand for KAI2. Until its identification, synthetic karrikins or the strigolactone-like molecule GR24 are used to probe the karrikin signaling pathway. While the model plant Arabidopsis contains only one KAI2 gene, several copies are maintained in other species suggesting sub-functionalization. We report that genomes of species in the legume hologalegina clade encode two KAI2 versions. In Lotus japonicus, they diverge in their binding ability to synthetic ligands due to three amino acid changes in their binding pocket, of which two are conserved across legumes and one has independently occurred in several species across the angiosperm phylogeny. Surprisingly, L. japonicus hypocotyls react with developmental responses to two different karrikins (KAR1, KAR2) and a synthetic strigolactone rac-GR24, while root development responds only to KAR1. This shows that there is not only diversity in ligand-receptor relationships but possibly also organ-specific uptake or metabolism of divergent butenolide molecules.
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- 2020
21. Validated Method for Strigolactone Quantification by Ultra High-Performance Liquid Chromatography - Electrospray Ionisation Tandem Mass Spectrometry Using Novel Deuterium Labelled Standards
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David Touboul, Stéphanie Boutet-Mercey, François-Didier Boyer, Catherine Rameau, Amélie Roux, Grégory Mouille, Jean-Paul Pillot, François Perreau, Guillaume Clavé, and Isabelle Schmitz-Afonso
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0106 biological sciences ,0301 basic medicine ,Electrospray ,Ethyl acetate ,Strigolactone ,Plant Science ,Mass spectrometry ,Tandem mass spectrometry ,01 natural sciences ,Biochemistry ,High-performance liquid chromatography ,Analytical Chemistry ,03 medical and health sciences ,chemistry.chemical_compound ,Drug Discovery ,Chromatography ,integumentary system ,Chemistry ,fungi ,Extraction (chemistry) ,General Medicine ,030104 developmental biology ,Complementary and alternative medicine ,Molecular Medicine ,Quantitative analysis (chemistry) ,010606 plant biology & botany ,Food Science - Abstract
Introduction Strigolactones (SLs) are important plant hormones. They are difficult to analyse because they occur in very small concentrations especially in comparison with other plant hormones and other substances can interfere with their detection. Objective To develop a procedure for the extraction, purification and quantification of SLs from plant roots. Methodology Samples were prepared by extraction of plant root tissues with ethyl acetate. Then the extracts were further purified with silica column chromatography. The natural SLs in the final extracts were quantified using novel deuterium labelled SLs. The results of the methodology were compared with those of the procedure of Yoneyama and coworkers. Results This procedure required about 1-g root samples to detect and quantify simultaneously the SLs (orobanchyl acetate and fabacyl acetate) concentration with high reliability. Conclusion A method was developed for determining endogenous fabacyl acetate and orobanchyl acetate in plant tissue based on novel deuterium labelled standards. A method of orobanchol quantification using a synthetic SL GR24 as internal standard was proposed. Copyright © 2017 John Wiley & Sons, Ltd.
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- 2017
22. Cannalactone: a new non-canonical strigolactone exudated by Cannabis sativa roots with a pivotal role in host specialization within French broomrape (Phelipanche ramosa) populations
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Oumayma Hamzaoui, Alexandre Maciuk, Sabine Delgrange, Katia Kerdja, Claire Thouminot, Alexandre de Saint Germain, Soizic Rochange, François-Didier Boyer, Philippe SIMIER, Jean-Bernard Pouvreau, Boyer, François-Didier, Isolement, structure, transformations et synthèse de substances naturelles (ISTSSN), Université de Reims Champagne-Ardenne (URCA)-Centre National de la Recherche Scientifique (CNRS), Institut Jean-Pierre Bourgin (IJPB), Institut National de la Recherche Agronomique (INRA)-AgroParisTech, Laboratoire de Recherche en Sciences Végétales (LRSV), Centre National de la Recherche Scientifique (CNRS)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées, Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS), EA 1157 Laboratoire de Biologie et de Pathologie Végétales, Université de Nantes (UN), Laboratoire de biologie et pathologie végétales (LBPV), Université de Nantes - Faculté des Sciences et des Techniques, Université de Nantes (UN)-Université de Nantes (UN), Biomolécules : Conception, Isolement, Synthèse (BioCIS), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Paris-Sud - Paris 11 (UP11)-Université de Cergy Pontoise (UCP), Université Paris-Seine-Université Paris-Seine, Evolution des Interactions Plantes-Microorganismes, Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), and Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST)
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[SDV] Life Sciences [q-bio] ,[CHIM.ANAL] Chemical Sciences/Analytical chemistry ,[CHIM.ANAL]Chemical Sciences/Analytical chemistry ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,[SDV]Life Sciences [q-bio] ,[SDV.BV]Life Sciences [q-bio]/Vegetal Biology ,[SDV.BV] Life Sciences [q-bio]/Vegetal Biology ,[CHIM.ORGA] Chemical Sciences/Organic chemistry ,ComputingMilieux_MISCELLANEOUS - Abstract
International audience
- Published
- 2019
23. Iron(III)-Triflate-Catalyzed Multiple Glycosylations with Peracetylated β-d-Glucosamine
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Jean-Marie Beau, Amandine Xolin, François-Didier Boyer, and Stéphanie Norsikian
- Subjects
Glycan ,biology ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,Mannose ,Homogeneous catalysis ,010402 general chemistry ,01 natural sciences ,Combinatorial chemistry ,Cycloaddition ,0104 chemical sciences ,chemistry.chemical_compound ,Microwave chemistry ,Propargyl ,biology.protein ,Organic chemistry ,Physical and Theoretical Chemistry ,Trifluoromethanesulfonate ,Linker - Abstract
Direct multiple glycosylations of thioaryl and propargyl mannopyranosides with peracetylated β-d-glucosamine have been carried out using catalytic iron(III) triflate as a promoter in the presence of 2,4,6-tri-tert-butylpyrimidine under microwave irradiation. This has led to the one-step formation of various oligosaccharides with mannose at the branching point. Subsequent direct introduction of a linker through copper-catalyzed azide–alkyne cycloaddition with the propargyl branched glycan and final deprotection gave rapid access to N-glycan mimetics.
- Published
- 2016
24. Chitooligosaccharide Synthesis Using an Ionic Tag
- Author
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Jean-Marie Beau, Laura Gillard, Anh-Tuan Tran, François-Didier Boyer, Université Paris-Sud - Paris 11 (UP11), Institut Jean-Pierre Bourgin (IJPB), Institut National de la Recherche Agronomique (INRA)-AgroParisTech, Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Centre National de la Recherche Scientifique (CNRS), French Agence Nationale de la Recherche (ANR) [ANR-12-BS07-0022], and CHARM3AT Labex program
- Subjects
Glycosylation ,010405 organic chemistry ,Chemistry ,[SDV]Life Sciences [q-bio] ,Organic Chemistry ,Carbohydrates ,Ionic bonding ,010402 general chemistry ,01 natural sciences ,Combinatorial chemistry ,Ionic liquids ,0104 chemical sciences ,chemistry.chemical_compound ,Synthetic methods ,[SDV.IDA]Life Sciences [q-bio]/Food engineering ,Ionic liquid ,[SDV.BV]Life Sciences [q-bio]/Vegetal Biology ,Organic chemistry ,[SPI.GPROC]Engineering Sciences [physics]/Chemical and Process Engineering ,Stereoselectivity ,Physical and Theoretical Chemistry ,Protecting groups - Abstract
International audience; An environmentally improved synthesis of the N-differentiated chitotetrasaccharide CO-IV-(NH2), a key intermediate for the preparation of lipochitooligosaccharides and the TMG-chitotriomycin, is reported based on a chromatography-free ionic-liquid tagging approach. The method involves the glycosylation of ionic-liquid-tagged acceptors with thioglucosamine donors leading to the stereoselective formation of -(14)-linked glucosamine-containing oligomers.
- Published
- 2016
25. Design and visualization of second-generation cyanoisoindole-based fluorescent strigolactone analogs
- Author
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Sofie Goormachtig, Anna M. Kaczmarek, Lukas Braem, Sylwia Magdalena Struk, Rik Van Deun, François-Didier Boyer, Melissa Van Overtveldt, Thomas S. A. Heugebaert, Christian V. Stevens, Kris Gevaert, Université d’Opole, Universiteit Gent = Ghent University [Belgium] (UGENT), Dept Med Prot Res, Flanders Institute for Biotechnology, Center for Plant Systems Biology (PSB Center), Vlaams Instituut voor Biotechnologie [Ghent, Belgique] (VIB), and Research Foundation - Flanders (FWO Vlaanderen)
- Subjects
0106 biological sciences ,0301 basic medicine ,Arabidopsis ,Strigolactone ,Repressor ,parasitic seed germination ,Germination ,Plant Science ,Protein degradation ,fluorescence labeling ,01 natural sciences ,smxl6 degradation ,03 medical and health sciences ,Lactones ,Plant Growth Regulators ,In vivo ,Genetics ,Arabidopsis thaliana ,Moiety ,[SDV.BV]Life Sciences [q-bio]/Vegetal Biology ,strigolactone ,Fluorescent Dyes ,biology ,Arabidopsis Proteins ,hypocotyl elongation ,arabidopsis thaliana ,Cell Biology ,phelipanche ramosa ,biology.organism_classification ,isoindole ,Fluorescence ,Terpenoid ,Hypocotyl ,030104 developmental biology ,Biochemistry ,pyrroloindole ,Proteolysis ,Seeds ,010606 plant biology & botany ,Signal Transduction - Abstract
International audience; Strigolactones (SLs) are a family of terpenoid allelochemicals that were recognized as plant hormones only a decade ago. They influence a myriad of both above- and below-ground developmental processes, and are an important survival strategy for plants in nutrient-deprived soils. A rapidly emerging approach to gain knowledge on hormone signaling is the use of traceable analogs. A unique class of labeled SL analogs was constructed, in which the original tricyclic lactone moiety of natural SLs is replaced by a fluorescent cyanoisoindole ring system. Biological evaluation as parasitic seed germination stimulant and hypocotyl elongation repressor proved the potency of the cyanoisoindole strigolactone analogs (CISAs) to be comparable to the commonly accepted standard GR24. Additionally, via a SMXL6 protein degradation assay, we provided molecular evidence that the compounds elicit SL-like responses through the natural signaling cascade. All CISAs were shown to exhibit fluorescent properties, and the high quantum yield and Stokes shift of the pyrroloindole derivative CISA-7 also enabled in vivo visualization in plants. In contrast to the previously reported fluorescent analogs, CISA-7 displays a large similarity in shape and structure with natural SLs, which renders the analog a promising tracer to investigate the spatiotemporal distribution of SLs in plants and fungi.
- Published
- 2018
26. Quantitative Tandem Affinity Purification, an Effective Tool to Investigate Protein Complex Composition in Plant Hormone Signaling: Strigolactones in the Spotlight
- Author
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Sylwia Struk, Lukas Braem, Alan Walton, Annick De Keyser, François-Didier Boyer, Geert Persiau, Geert De Jaeger, Kris Gevaert, Sofie Goormachtig, Center for Plant Systems Biology (PSB Center), Vlaams Instituut voor Biotechnologie [Ghent, Belgique] (VIB), Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Department of Plant Systems Biology, Department of Plant Biotechnology and Genetics, Universiteit Gent = Ghent University [Belgium] (UGENT), Flanders Institute for Biotechnology, Dept Med Prot Res, Strategic-Basic-Research fellowship of the Research Foundation-Flanders, and Goormachtig, Sofie
- Subjects
strigolactones ,SMXL7 ,qTAP ,plant hormone signaling ,protein dynamics ,0106 biological sciences ,0301 basic medicine ,TRANSCRIPTION FACTOR COMPLEXES ,Repressor ,Plant Science ,lcsh:Plant culture ,Proteomics ,01 natural sciences ,03 medical and health sciences ,Methods ,[SDV.BV]Life Sciences [q-bio]/Vegetal Biology ,Arabidopsis thaliana ,lcsh:SB1-1110 ,Mode of action ,SHOOT DEVELOPMENT ,Tandem affinity purification ,IDENTIFICATION ,biology ,Chemistry ,Protein dynamics ,Biology and Life Sciences ,REPRESSOR ,MASS-SPECTROMETRY ,DEGRADATION ,QUANTIFICATION ,biology.organism_classification ,Cell biology ,030104 developmental biology ,ARABIDOPSIS-THALIANA ,PROTEOMICS ,GROWTH ,Plant hormone ,Signal transduction ,010606 plant biology & botany - Abstract
International audience; Phytohormones tightly regulate plant growth by integrating changing environmental and developmental cues. Although the key players have been identified in many plant hormonal pathways, the molecular mechanisms and mode of action of perception and signaling remain incompletely resolved. Characterization of protein partners of known signaling components provides insight into the formed protein complexes, but, unless quantification is involved, does not deliver much, if any, information about the dynamics of the induced or disrupted protein complexes. Therefore, in proteomics research, the discovery of what actually triggers, regulates or interrupts the composition of protein complexes is gaining importance. Here, tandem affinity purification coupled to mass spectrometry (TAP-MS) is combined with label-free quantification (LFQ) to a highly valuable tool to detect physiologically relevant, dynamic protein-protein interactions in Arabidopsis thaliana cell cultures. To demonstrate its potential, we focus on the signaling pathway of one of the most recently discovered phytohormones, strigolactones.
- Published
- 2018
27. Novel class of reversible chiral ionic liquids derived from natural amino acids: synthesis and characterization
- Author
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Giang Vo-Thanh, Violeta Rodriguez-Ruiz, Martial Toffano, François-Didier Boyer, Lucie Bouchardy, Chloée Bournaud, Patrick Judeinstein, Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Université Paris-Sud - Paris 11 (UP11)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Laboratoire Léon Brillouin (LLB - UMR 12), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Centre National de la Recherche Scientifique (CNRS)-Université Paris-Saclay, Ministere de l'Enseignement Superieur et de la Recherche, Labex CHARM3AT, CNRS [UMR 8182, UPR 2301], Universite Paris-Sud, Centre National de la Recherche Scientifique (CNRS), Equipe de recherche sur les relations matrice extracellulaire-cellules (ERRMECe), Fédération INSTITUT DES MATÉRIAUX DE CERGY-PONTOISE (I-MAT), Université de Cergy Pontoise (UCP), Université Paris-Seine-Université Paris-Seine-Université de Cergy Pontoise (UCP), Université Paris-Seine-Université Paris-Seine, Université Paris-Sud - Paris 11 (UP11)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie Moléculaire Organique (ICMO), Université Paris-Sud - Paris 11 (UP11), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Paris-Sud - Paris 11 (UP11)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and RMN en milieu orienté (RMO)
- Subjects
inorganic chemicals ,reversible ionic liquids ,chirality ,silylamines ,02 engineering and technology ,010402 general chemistry ,01 natural sciences ,chemistry.chemical_compound ,[CHIM]Chemical Sciences ,heterocyclic compounds ,ComputingMilieux_MISCELLANEOUS ,chemistry.chemical_classification ,Quantitative Biology::Biomolecules ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,organic chemicals ,carbon dioxide ,General Chemistry ,[CHIM.CATA]Chemical Sciences/Catalysis ,021001 nanoscience & nanotechnology ,Combinatorial chemistry ,0104 chemical sciences ,Amino acid ,Characterization (materials science) ,Condensed Matter::Soft Condensed Matter ,chemistry ,Ionic liquid ,natural amino acids ,[CHIM.OTHE]Chemical Sciences/Other ,0210 nano-technology ,Chirality (chemistry) - Abstract
International audience; A novel class of reversible chiral ammonium‐based ionic liquids has been designed and synthesized. These chiral ammonium carbamate salts were quickly obtained by adding 1 atmosphere of CO2 gas to chiral silylated amines, easily prepared at gram scale and in some steps from natural amino acids as bio‐renewable substrates. Some physical properties of these reversible chiral ionic liquids such as reversibility temperature, thermal degradation, miscibility, and stability have been determined. The spectroscopic characteristics of the silylated amine and ionic liquid states have also been compared. The properties of reversibility, chirality, and ease of preparation should make these silylamine‐ionic liquid phases as promising solvents and/or catalysts for several applications, especially in asymmetric catalysis fields.
- Published
- 2018
28. Stereocontrolled glycoside synthesis by activation of glycosyl sulfone donors with scandium( iii ) triflate
- Author
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Romain Losa, Amandine Xolin, Aicha Kaid, Jean-Marie Beau, Stéphanie Norsikian, Cédric Tresse, François-Didier Boyer, Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), CNRS, CHARM3AT Labex program [ANR-11-LABX-39], and Labex Saclay Plant Sciences-SPS [ANR-10-LABX-0040-SPS]
- Subjects
animal structures ,010405 organic chemistry ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,Aryl ,Organic Chemistry ,chemistry.chemical_element ,macromolecular substances ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Medicinal chemistry ,Glycoside synthesis ,0104 chemical sciences ,3. Good health ,Sulfone ,carbohydrates (lipids) ,chemistry.chemical_compound ,chemistry ,Glycosyl ,lipids (amino acids, peptides, and proteins) ,Scandium ,Physical and Theoretical Chemistry ,Trifluoromethanesulfonate - Abstract
International audience; The activation of aryl glycosyl sulfone donors has been achieved using scandium(III) triflate and has led to the selective preparation of alpha-mannosides resulting from a post-glycosylation anomerization.
- Published
- 2018
29. From lateral root density to nodule number, the strigolactone analogue GR24 shapes the root architecture of Medicago truncatula
- Author
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Justine Fromentin, Annick De Keyser, Bruno Guillotin, François-Didier Boyer, Rosita Endah Yocgo, Karl J. Kunert, Sofie Goormachtig, Carolien De Cuyper, Center for Plant Systems Biology (PSB Center), Vlaams Instituut voor Biotechnologie [Ghent, Belgique] (VIB), Institut de Chimie des Substances Naturelles (ICSN), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)
- Subjects
0106 biological sciences ,Physiology ,GR24 ,Strigolactone ,Plant Science ,Root system ,root architecture ,Plant Root Nodulation ,Plant Roots ,01 natural sciences ,Lactones ,03 medical and health sciences ,Botany ,ethylene ,[CHIM]Chemical Sciences ,nodulation ,030304 developmental biology ,0303 health sciences ,Rhizosphere ,ENOD11 ,biology ,fungi ,Lateral root ,food and beverages ,medicago truncatula ,biology.organism_classification ,Medicago truncatula ,Arbuscular mycorrhiza ,Crosstalk (biology) ,Sinorhizobium ,Heterocyclic Compounds, 3-Ring ,010606 plant biology & botany - Abstract
International audience; In the rhizosphere, strigolactones not only act as crucial signalling molecules in the communication of plants with parasitic weeds and arbuscular mycorrhiza, but they also play a key role in regulating different aspects of the root system. Here we investigated how strigolactones influence the root architecture of Medicago truncatula. We provide evidence that addition of the synthetic strigolactone analogue GR24 has an inhibitory effect on the lateral root density. Moreover, treatment with GR24 of Sinorhizobium meliloti-inoculated M. truncatula plants affects the nodule number both positively and negatively, depending on the concentration. Plants treated with 0.1 microM GR24 had a slightly increased number of nodules, whereas concentrations of 2 and 5 microM strongly reduced it. This effect was independent of the autoregulation of nodulation mechanism that is controlled by SUPER NUMERIC NODULE. Furthermore, we demonstrate that GR24 controls the nodule number through crosstalk with SICKLE-dependent ethylene signalling. Additionally, because the expression of the nodulation marker EARLY NODULATION11 was strongly reduced in GR24-treated plants, we concluded that strigolactones influence nodulation at a very early stage of the symbiotic interaction.
- Published
- 2014
30. Synthesis of lipo-chitooligosaccharide analogues and their interaction with LYR3, a high affinity binding protein for Nod factors and Myc-LCOs
- Author
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Antoine Brossay, Nathan Berthelot, François-Didier Boyer, Aurélie Baron, Jean-Jacques Bono, Boris Vauzeilles, Dominique Urban, Jean-Marie Beau, Virginie Gasciolli, Université Paris Saclay (COmUE), Laboratoire des interactions plantes micro-organismes (LIPM), Institut National de la Recherche Agronomique (INRA)-Centre National de la Recherche Scientifique (CNRS), Institut Jean-Pierre Bourgin (IJPB), Institut National de la Recherche Agronomique (INRA)-AgroParisTech, Institut de Chimie des Substances Naturelles (ICSN) - Centre National de la Recherche Scientifique (CNRS), CHARM3AT Labex program : ANR-11-LABX-39, and Labex Saclay Plant Sciences-SPS : ANR-10-LABX-0040-SPS
- Subjects
Stereochemistry ,Triazole ,Oligosaccharides ,Chitin ,010402 general chemistry ,01 natural sciences ,Biochemistry ,chemistry.chemical_compound ,Residue (chemistry) ,Medicago truncatula ,Physical and Theoretical Chemistry ,Receptor ,Plant Proteins ,Chitosan ,biology ,010405 organic chemistry ,Depolymerization ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,Ligand binding assay ,Organic Chemistry ,fungi ,food and beverages ,biology.organism_classification ,Cycloaddition ,3. Good health ,0104 chemical sciences ,chemistry - Abstract
International audience; Lipo-chitotetrasaccharide analogues where one central GlcNAc residue was replaced by a triazole unit have been synthesized from a derivative obtained by chitin depolymerization and a functionalized N-acetyl-glucosamine via the copper-catalyzed azide-alkyne cycloaddition. Their evaluation in a binding assay using LYR3, a putative lipo-chitooligosaccharide receptor in Medicago truncatula, shows a complete loss of binding.
- Published
- 2017
31. Ethylene controls adventitious root initiation sites in Arabidopsis hypocotyls independently of strigolactones
- Author
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Thomas Depaepe, Amanda Rasmussen, François-Didier Boyer, Yuming Hu, Filip Vandenbussche, Danny Geelen, Dominique Van Der Straeten, University of Nottingham, UK (UON), Universiteit Gent = Ghent University [Belgium] (UGENT), Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Univ Ghent, Fac Biosci Engn, Plant Prod, Coupure Links 653, B-9000 Ghent, Belgium, Partenaires INRAE, University of Nottingham, FP7 Marie Curie International Incoming Fellowships, Newton International Fellowships, Nottingham Research Fellowships, and Research Foundation-Flanders (FWO) [3G030612]
- Subjects
0106 biological sciences ,0301 basic medicine ,Hypocotyl zonation ,Ethylene ,[SDV]Life Sciences [q-bio] ,Arabidopsis ,Strigolactone ,CELL ELONGATION ,Plant Science ,Root hair elongation ,01 natural sciences ,Hypocotyl ,03 medical and health sciences ,chemistry.chemical_compound ,STRIGA-HERMONTHICA ,Botany ,Etiolation ,Arabidopsis thaliana ,SUNFLOWER HELIANTHUS-ANNUUS ,BIOSYNTHESIS ,SEEDLINGS ,WOUND RESPONSE ,APICAL HOOK DEVELOPMENT ,biology ,THALIANA ,Plant physiology ,Biology and Life Sciences ,BOX PROTEIN MAX2 ,biology.organism_classification ,Adventitious roots ,Cell biology ,030104 developmental biology ,chemistry ,Agronomy and Crop Science ,AUXIN TRANSPORT ,010606 plant biology & botany - Abstract
International audience; Adventitious root formation is essential for cutting propagation of diverse species; however, until recently little was known about its regulation. Strigolactones and ethylene have both been shown to inhibit adventitious roots and it has been suggested that ethylene interacts with strigolactones in root hair elongation. We have investigated the interaction between strigolactones and ethylene in regulating adventitious root formation in intact seedlings of Arabidopsis thaliana. We used strigolactone mutants together with 1-aminocyclopropane-1-carboxylic acid (ACC) (ethylene precursor) treatments and ethylene mutants together with GR24 (strigolactone agonist) treatments. Importantly, we conducted a detailed mapping of adventitious root initiation along the hypocotyl and measured ethylene production in strigolactone mutants. ACC treatments resulted in a slight increase in adventitious root formation at low doses and a decrease at higher doses, in both wild-type and strigolactone mutants. Furthermore, the distribution of adventitious roots dramatically changed to the top third of the hypocotyl in a dose-dependent manner with ACC treatments in both wild-type and strigolactone mutants. The ethylene mutants all responded to treatments with GR24. Wild type and max4 (strigolactone-deficient mutant) produced the same amount of ethylene, while emanation from max2 (strigolactone-insensitive mutant) was lower. We conclude that strigolactones and ethylene act largely independently in regulating adventitious root formation with ethylene controlling the distribution of root initiation sites. This role for ethylene may have implications for flood response because both ethylene and adventitious root development are crucial for flood tolerance.
- Published
- 2017
32. Synthesis of the Fungal Lipo-Chitooligosaccharide Myc-IV (C16:0, S), Symbiotic Signal of Arbuscular Mycorrhiza
- Author
-
Boris Vauzeilles, Jean-Marie Beau, Arnaud Stévenin, Isabelle Schmitz-Afonso, François-Didier Boyer, and Laura Gillard
- Subjects
Glycosylation ,biology ,010405 organic chemistry ,fungi ,Organic Chemistry ,Glycosyl acceptor ,Acetal ,010402 general chemistry ,biology.organism_classification ,01 natural sciences ,0104 chemical sciences ,Arbuscular mycorrhiza ,chemistry.chemical_compound ,chemistry ,Biochemistry ,lipids (amino acids, peptides, and proteins) ,Stereoselectivity ,Physical and Theoretical Chemistry ,Oxidative cleavage - Abstract
A new synthesis of the fungal lipo-chitooligosaccharide Myc-IV (C16:0, S), which was recently reported to be a major symbiotic signalling molecule in arbuscular mycorrhiza, is described. Key steps include the oxidative cleavage of a 4,6-O-benzylidene acetal to prepare a disaccharidic glycosyl acceptor, and stereoselective glycosylations with 2-methyl-5-tert-butylphenyl thioglycosyl donors.
- Published
- 2013
33. A Fluorescent Alternative to the Synthetic Strigolactone GR24
- Author
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Rik Van Deun, Danny Geelen, François-Didier Boyer, Christian V. Stevens, Amanda Rasmussen, Cedrick Matthys, Sofie Goormachtig, Thomas S. A. Heugebaert, Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Center for Plant Systems Biology (PSB Center), Vlaams Instituut voor Biotechnologie [Ghent, Belgique] (VIB), Faculty of Bioscience Engineering, Ghent University, Universiteit Gent = Ghent University [Belgium] (UGENT), Department of Plant Production [Ghent], Faculty of Bioscience Engineering [Ghent], Universiteit Gent = Ghent University [Belgium] (UGENT)-Universiteit Gent = Ghent University [Belgium] (UGENT), FP7 Marie Curie International Incoming Fellowships, Hercules Foundation [AUGE/09/024], Research Foundation-Flanders [0081.10N], and Ghent University [01N01010]
- Subjects
0106 biological sciences ,Arabidopsis ,Strigolactone ,Germination ,strigolactones ,Plant Science ,Isoindoles ,Plant Roots ,01 natural sciences ,Lactones ,03 medical and health sciences ,4-Butyrolactone ,Gene Expression Regulation, Plant ,In vivo ,branching ,Botany ,adventitious rooting ,Molecular Biology ,030304 developmental biology ,0303 health sciences ,biology ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,Arabidopsis Proteins ,Orobanche ,Biological activity ,biology.organism_classification ,In vitro ,Spectrometry, Fluorescence ,fluorescent markers ,Biochemistry ,parasitic weed seed germination ,Shoot ,Signal transduction ,Carrier Proteins ,Plant Shoots ,010606 plant biology & botany - Abstract
International audience; Strigolactones have recently been implicated in both above- and below-ground developmental pathways in higher plants. To facilitate the molecular and chemical properties of strigolactones in vitro and in vivo, we have developed a fluorescent strigolactone molecule, CISA-1, synthesized via a novel method which was robust, high-yielding, and used simple starting materials. We demonstrate that CISA-1 has a broad range of known strigolactone activities and further report on an adventitious rooting assay in Arabidopsis which is a highly sensitive and rapid method for testing biological activity of strigolactone analogs. In this rooting assay and the widely used Orobanche germination assay, CISA-1 showed stronger biological activity than the commonly tested GR24. CISA-1 and GR24 were equally effective at inhibiting branching in Arabidopsis inflorescence stems. In both the branching and adventitious rooting assay, we also demonstrated that CISA-1 activity is dependent on the max strigolactone signaling pathway. In water methanol solutions, CISA-1 was about threefold more stable than GR24, which may contribute to the increased activity observed in the various biological tests.
- Published
- 2013
34. An histidine covalent receptor and butenolide complex mediates strigolactone perception
- Author
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Frank Pelissier, Marie-Ange Badet-Denisot, Alexandre de Saint Germain, Marco Bürger, Colin G. N. Turnbull, Pascal Retailleau, Sandrine Bonhomme, David Cornu, Jean-Paul Pillot, Jean-Pierre Le Caer, Guillaume Clavé, Catherine Rameau, François-Didier Boyer, Joanne Chory, Institut Jean-Pierre Bourgin (IJPB), Institut National de la Recherche Agronomique (INRA)-AgroParisTech, Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS), Institut des Sciences Moléculaires (ISM), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Centre National de la Recherche Scientifique (CNRS), SICaPS (SICaPS), Département Plateforme (PF I2BC), Institut de Biologie Intégrative de la Cellule (I2BC), Université Paris-Sud - Paris 11 (UP11)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Centre National de la Recherche Scientifique (CNRS)-Université Paris-Saclay-Université Paris-Sud - Paris 11 (UP11)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Centre National de la Recherche Scientifique (CNRS)-Université Paris-Saclay-Institut de Biologie Intégrative de la Cellule (I2BC), Université Paris-Sud - Paris 11 (UP11)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Centre National de la Recherche Scientifique (CNRS)-Université Paris-Saclay-Université Paris-Sud - Paris 11 (UP11)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Centre National de la Recherche Scientifique (CNRS)-Université Paris-Saclay, The Salk Institute for Biological Studies, Division of cell and molecular biology, Imperial College London, Unité de Recherche en Génétique et Amélioration des Plantes (UR254), Institut National de la Recherche Agronomique (INRA), Plant Biology Laboratory and Howard Hughes Medical Institute, Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1 (UB)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Institut de Biologie Intégrative de la Cellule (I2BC), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), Agence Nationale de la Recherche [ANR-12-BSV6-004-01], Stream COST Action [FA1206], US National Institutes of Health [R01 GM094428], Howard Hughes Medical Institute, Catharina Foundation, Labex Saclay Plant Sciences-SPS [ANR-10-LABX-0040-SPS], Terry L. Sheppard, Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Centre National de la Recherche Scientifique (CNRS)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Université Sciences et Technologies - Bordeaux 1-Université Montesquieu - Bordeaux 4-Institut de Chimie du CNRS (INC), Université Paris-Sud - Paris 11 (UP11)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Université Paris-Sud - Paris 11 (UP11)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Institut de Biologie Intégrative de la Cellule (I2BC), and Université Paris-Sud - Paris 11 (UP11)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Université Paris-Sud - Paris 11 (UP11)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)
- Subjects
0106 biological sciences ,0301 basic medicine ,Biochemistry & Molecular Biology ,Stereochemistry ,Medicinal And Biomolecular Chemistry ,Strigolactone ,Biology ,Ligands ,01 natural sciences ,Article ,Lactones ,03 medical and health sciences ,4-Butyrolactone ,Plant Growth Regulators ,Catalytic triad ,[CHIM]Chemical Sciences ,[SDV.BV]Life Sciences [q-bio]/Vegetal Biology ,Histidine ,[SDV.BBM]Life Sciences [q-bio]/Biochemistry, Molecular Biology ,Biochemistry And Cell Biology ,Molecular Biology ,Plant Proteins ,Butenolide ,Molecular Structure ,Peas ,food and beverages ,Cell Biology ,biology.organism_classification ,Ligand (biochemistry) ,Karrikin ,030104 developmental biology ,Biochemistry ,Covalent bond ,Plant hormone ,Heterocyclic Compounds, 3-Ring ,010606 plant biology & botany - Abstract
International audience; Strigolactone plant hormones control plant architecture and are key players in both symbiotic and parasitic interactions. They contain an ABC tricyclic lactone connected to a butenolide group, the D ring. The DWARF14 (D14) strigolactone receptor belongs to the superfamily of α/β-hydrolases, and is known to hydrolyze the bond between the ABC lactone and the D ring. Here we characterized the binding and catalytic functions of RAMOSUS3 (RMS3), the pea (Pisum sativum) ortholog of rice (Oryza sativa) D14 strigolactone receptor. Using new profluorescent probes with strigolactone-like bioactivity, we found that RMS3 acts as a single-turnover enzyme that explains its apparent low enzymatic rate. We demonstrated the formation of a covalent RMS3-D-ring complex, essential for bioactivity, in which the D ring was attached to histidine 247 of the catalytic triad. These results reveal an undescribed mechanism of plant hormone reception in which the receptor performs an irreversible enzymatic reaction to generate its own ligand.
- Published
- 2016
35. The Whats, the Wheres and the Hows of strigolactone action in the roots
- Author
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François-Didier Boyer, Sylwia Magdalena Struk, Sofie Goormachtig, Cedrick Matthys, Kris Gevaert, Alan Walton, Elisabeth Stes, Department of plant Biotechnology and Bioinformatics, University of Gent, Department of plant systems biology, Flanders Institute for Biotechnology, Department of Biochemistry, Universiteit Gent = Ghent University [Belgium] (UGENT), Institut Jean-Pierre Bourgin (IJPB), Institut National de la Recherche Agronomique (INRA)-AgroParisTech, Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), VIB, Dept Med Prot Res, Albert Baertsoenkaai 3, B-9000 Ghent, Belgium, Partenaires INRAE, Univ Ghent, Dept Biochem, Albert Baertsoenkaai 3, B-9000 Ghent, Belgium, Ghent University Hercules program for the UPLC-Synapt Q-Tof HDMS system [AUGE/014], European Cooperation on Science and Technology (COST action) [FA1206], 'Bijzonder Onderzoeksfonds' of the Ghent University, and VIB International PhD program fellowship
- Subjects
0106 biological sciences ,0301 basic medicine ,Hormonal activity ,[SDV]Life Sciences [q-bio] ,Arabidopsis ,Strigolactone ,Plant Science ,Biology ,Arbuscular mycorrhizal fungi ,01 natural sciences ,Plant Roots ,03 medical and health sciences ,Lactones ,Root system architecture ,Plant Growth Regulators ,Botany ,[SDV.IDA]Life Sciences [q-bio]/Food engineering ,Genetics ,analog gr24 ,[SDV.BV]Life Sciences [q-bio]/Vegetal Biology ,[SPI.GPROC]Engineering Sciences [physics]/Chemical and Process Engineering ,Plant roots ,rice ,auxin transport ,Biological Transport ,biology.organism_classification ,Cell biology ,Plant development ,rac-GR24 ,030104 developmental biology ,plant development ,Strigolactone-related compounds ,f-box protein ,010606 plant biology & botany ,Signal Transduction - Abstract
International audience; Strigolactones control various aspects of plant development, including root architecture. Here, we review how strigolactones act in the root and survey the strigolactone specificity of signaling components that affect root development. Strigolactones are a group of secondary metabolites produced in plants that have been assigned multiple roles, of which the most recent is hormonal activity. Over the last decade, these compounds have been shown to regulate various aspects of plant development, such as shoot branching and leaf senescence, but a growing body of literature suggests that these hormones play an equally important role in the root. In this review, we present all known root phenotypes linked to strigolactones. We examine the expression and presence of the main players in biosynthesis and signaling of these hormones and bring together the available information that allows us to explain how strigolactones act to modulate the root system architecture.
- Published
- 2016
36. Strigolactones spatially influence lateral root development through the cytokinin signaling network
- Author
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François-Didier Boyer, Lingxiang Jiang, Sofie Goormachtig, Tom Beeckman, Carolien De Cuyper, Annick De Keyser, Lien De Smet, Cedrick Matthys, Stephen Depuydt, Belén Márquez-García, Department of Plant Systems Biology, VIB, Department of Plant Biotechnology and Bioinformatics, Ghent University [Belgium] (UGENT), Institut Jean-Pierre Bourgin (IJPB), Institut National de la Recherche Agronomique (INRA)-AgroParisTech, European Cooperation on Science and Technology (COST action) [FA1206], China Scholarship Council, 'Bijzonder Onderzoeksfonds' of Ghent University, Universiteit Gent = Ghent University [Belgium] (UGENT), and Hitoshi Sakakibara
- Subjects
0106 biological sciences ,0301 basic medicine ,Cytokinins ,Histidine Kinase ,Arabidopsis thaliana ,Physiology ,[SDV]Life Sciences [q-bio] ,Mutant ,F-BOX PROTEIN ,Arabidopsis ,Plant Science ,strigolactones ,ACTS DOWNSTREAM ,01 natural sciences ,Plant Roots ,ANALOG GR24 ,chemistry.chemical_compound ,Lactones ,[SDV.IDA]Life Sciences [q-bio]/Food engineering ,chemistry.chemical_classification ,CELL-DIFFERENTIATION ,biology ,polar auxin transport ,food and beverages ,ARABIDOPSIS ,Cell biology ,DNA-Binding Proteins ,Biochemistry ,Cytokinin ,Heterocyclic Compounds, 3-Ring ,Signal Transduction ,Research Paper ,DEPENDENT AUXIN GRADIENTS ,Strigolactone ,FOUNDER CELLS ,lateral root development ,03 medical and health sciences ,BUD OUTGROWTH ,Auxin ,[SDV.BV]Life Sciences [q-bio]/Vegetal Biology ,[SPI.GPROC]Engineering Sciences [physics]/Chemical and Process Engineering ,LEAF SENESCENCE ,RESPONSE REGULATORS ,Arabidopsis Proteins ,Lateral root ,cytokinin signaling ,Biology and Life Sciences ,biology.organism_classification ,030104 developmental biology ,chemistry ,Polar auxin transport ,Protein Kinases ,010606 plant biology & botany ,Transcription Factors - Abstract
Highlight Strigolactones monitor lateral root development in a spatiotemporal manner by an interplay with cytokinin., Strigolactones are important rhizosphere signals that act as phytohormones and have multiple functions, including modulation of lateral root (LR) development. Here, we show that treatment with the strigolactone analog GR24 did not affect LR initiation, but negatively influenced LR priming and emergence, the latter especially near the root–shoot junction. The cytokinin module ARABIDOPSIS HISTIDINE KINASE3 (AHK3)/ARABIDOPSIS RESPONSE REGULATOR1 (ARR1)/ARR12 was found to interact with the GR24-dependent reduction in LR development, because mutants in this pathway rendered LR development insensitive to GR24. Additionally, pharmacological analyses, mutant analyses, and gene expression analyses indicated that the affected polar auxin transport stream in mutants of the AHK3/ARR1/ARR12 module could be the underlying cause. Altogether, the data reveal that the GR24 effect on LR development depends on the hormonal landscape that results from the intimate connection with auxins and cytokinins, two main players in LR development.
- Published
- 2016
37. The response of the root proteome to the synthetic strigolactone GR24 in Arabidopsis
- Author
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Geert Goeminne, Jonathan Vandenbussche, François-Didier Boyer, Lukas Braem, Ruben Vanholme, Kris Gevaert, Alan Walton, Justine Fromentin, Sofie Goormachtig, Elisabeth Stes, Cedrick Matthys, An Staes, Carolien De Cuyper, Wout Boerjan, Marnik Vuylsteke, Department of plant systems biology, Flanders Institute for Biotechnology, Department of plant Biotechnology and Bioinformatics, University of Gent, Department of Biochemistry, Universiteit Gent = Ghent University [Belgium] (UGENT), Institut Jean-Pierre Bourgin (IJPB), Institut National de la Recherche Agronomique (INRA)-AgroParisTech, Centre National de la Recherche Scientifique (CNRS), Laboratoire des interactions plantes micro-organismes (LIPM), Institut National de la Recherche Agronomique (INRA)-Centre National de la Recherche Scientifique (CNRS), Ghent University [AUGE/014], European Cooperation on Science and Technology (COST action) [FA1206], VIB International PhD program fellowship, Ghent University [Belgium] (UGENT), Institut des Sciences des Plantes de Paris-Saclay (IPS2 (UMR_9213 / UMR_1403)), and Institut National de la Recherche Agronomique (INRA)-Université Paris-Sud - Paris 11 (UP11)-Université Paris Diderot - Paris 7 (UPD7)-Université d'Évry-Val-d'Essonne (UEVE)-Centre National de la Recherche Scientifique (CNRS)
- Subjects
Proteomics ,0106 biological sciences ,0301 basic medicine ,Flavonols ,[SDV]Life Sciences [q-bio] ,Arabidopsis ,ACTS DOWNSTREAM ,Plant Roots ,01 natural sciences ,Biochemistry ,Mass Spectrometry ,ANALOG GR24 ,Analytical Chemistry ,Lactones ,Gene Expression Regulation, Plant ,[SDV.IDA]Life Sciences [q-bio]/Food engineering ,PHOSPHATE ,Arabidopsis thaliana ,Rhizosphere ,biology ,Proteome ,[SDE]Environmental Sciences ,SHOOT ,Heterocyclic Compounds, 3-Ring ,Plant Shoots ,MAX1 ,GENES ,PROTEINS ,Quantitative proteomics ,Strigolactone ,03 medical and health sciences ,HORMONE ,Metabolomics ,[SDV.BV]Life Sciences [q-bio]/Vegetal Biology ,[SPI.GPROC]Engineering Sciences [physics]/Chemical and Process Engineering ,Molecular Biology ,Arabidopsis Proteins ,Research ,FLAVONOLS ,Biology and Life Sciences ,biology.organism_classification ,030104 developmental biology ,Mutation ,Carrier Proteins ,AUXIN TRANSPORT ,Chromatography, Liquid ,010606 plant biology & botany - Abstract
International audience; Strigolactones are plant metabolites that act as phytohormones and rhizosphere signals. Whereas most research on unraveling the action mechanisms of strigolactones is focused on plant shoots, we investigated proteome adaptation during strigolactone signaling in the roots of Arabidopsis thaliana. Through large-scale, time-resolved, and quantitative proteomics, the impact of the strigolactone analog rac-GR24 was elucidated on the root proteome of the wild type and the signaling mutant more axillary growth 2 (max2). Our study revealed a clear MAX2-dependent rac-GR24 response: an increase in abundance of enzymes involved in flavonol biosynthesis, which was reduced in the max2-1 mutant. Mass spectrometry-driven metabolite profiling and thin-layer chromatography experiments demonstrated that these changes in protein expression lead to the accumulation of specific flavonols. Moreover, quantitative RT-PCR revealed that the flavonol-related protein expression profile was caused by rac-GR24-induced changes in transcript levels of the corresponding genes. This induction of flavonol production was shown to be activated by the two pure enantiomers that together make up rac-GR24. Finally, our data provide much needed clues concerning the multiple roles played by MAX2 in the roots and a comprehensive view of the rac-GR24-induced response in the root proteome.
- Published
- 2016
38. Structure-Activity Relationship Studies of Strigolactone-Related Molecules for Branching Inhibition in Garden Pea: Molecule Design for Shoot Branching
- Author
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Catherine Rameau, Jean-Marie Beau, Jean-Paul Pillot, Arnaud Stévenin, Suzanne Ramos, Alexandre de Saint Germain, Victor Xiao Chen, Philippe Simier, Jean-Bernard Pouvreau, François-Didier Boyer, Philippe Delavault, Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Institut National de la Recherche Agronomique, Institut de Chimie des Substances Naturelles-Centre National de la Recherche Scientifique, and Universite de Nantes
- Subjects
0106 biological sciences ,STRIGA-GESNERIOIDES SEEDS ,Physiology ,Strigolactone ,Plant Science ,ACTS DOWNSTREAM ,Models, Biological ,01 natural sciences ,ANALOG GR24 ,ARBUSCULAR MYCORRHIZAL FUNGI ,Pisum ,Lactones ,Structure-Activity Relationship ,03 medical and health sciences ,Sativum ,Hydroponics ,BUD OUTGROWTH ,Gene Expression Regulation, Plant ,Axillary bud ,Botany ,Morphogenesis ,Genetics ,RNA, Messenger ,BIOLOGICAL EVALUATION ,Plant Proteins ,030304 developmental biology ,0303 health sciences ,Rhizosphere ,biology ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,Development and Hormone Action ,LUTEA LOUR ,Peas ,food and beverages ,Stereoisomerism ,AM FUNGI ,biology.organism_classification ,GERMINATION STIMULANTS ,Orobanche ,Germination ,Shoot ,ROOT PARASITIC PLANTS ,Biological Assay ,Oxidation-Reduction ,Plant Shoots ,010606 plant biology & botany - Abstract
Publication Inra prise en compte dans l'analyse bibliométrique des publications scientifiques mondiales sur les Fruits, les Légumes et la Pomme de terre. Période 2000-2012. http://prodinra.inra.fr/record/256699; International audience; Initially known for their role in the rhizosphere in stimulating the seed germination of parasitic weeds such as the Striga and Orobanche species, and later as host recognition signals for arbuscular mycorrhizal fungi, strigolactones (SLs) were recently rediscovered as a new class of plant hormones involved in the control of shoot branching in plants. Herein, we report the synthesis of new SL analogs and, to our knowledge, the first study of SL structure-activity relationships for their hormonal activity in garden pea (Pisum sativum). Comparisons with their action for the germination of broomrape (Phelipanche ramosa) are also presented. The pea rms1 SL-deficient mutant was used in a SL bioassay based on axillary bud length after direct SL application on the bud. This assay was compared with an assay where SLs were fed via the roots using hydroponics and with a molecular assay in which transcript levels of BRANCHED1, the pea homolog of the maize TEOSINTE BRANCHED1 gene were quantified in axillary buds only 6 h after application of SLs. We have demonstrated that the presence of a Michael acceptor and a methylbutenolide or dimethylbutenolide motif in the same molecule is essential. It was established that the more active analog 23 with a dimethylbutenolide as the D-ring could be used to control the plant architecture without strongly favoring the germination of P. ramosa seeds. Bold numerals refer to numbers of compounds.
- Published
- 2012
39. Stereochemistry, Total Synthesis, and Biological Evaluation of the New Plant Hormone Solanacol
- Author
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Jean-Marie Beau, Jean-Pierre Vors, Catherine Rameau, Victor Xiao Chen, Pascal Retailleau, François-Didier Boyer, Institut de Chimie des Substances Naturelles (ICSN), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)
- Subjects
0106 biological sciences ,biologie ,Stereochemistry ,radical reaction ,hormone ,Stereoisomerism ,Crystallography, X-Ray ,01 natural sciences ,Catalysis ,Kinetic resolution ,Lactones ,Plant Growth Regulators ,Molecule ,Organic chemistry ,kinetic resolution ,strigolactone ,ComputingMilieux_MISCELLANEOUS ,Biological evaluation ,résolution cinétique ,Molecular Structure ,biology ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,010405 organic chemistry ,Chemistry ,solanacol ,Organic Chemistry ,stereochemistry ,Total synthesis ,General Chemistry ,Biological evolution ,stéréochimie ,biology.organism_classification ,Biological Evolution ,0104 chemical sciences ,Plant hormone ,010606 plant biology & botany - Abstract
International audience
- Published
- 2010
40. Strigolactone biosynthesis and signaling in plant development
- Author
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Yasmine Ligerot, Mauricio Lopez-Obando, Catherine Rameau, Sandrine Bonhomme, François-Didier Boyer, Institut Jean-Pierre Bourgin (IJPB), Institut National de la Recherche Agronomique (INRA)-AgroParisTech, Agence Nationale de la Recherche [ANR-12-BSV6-004-01], and Stream COST Action FA1206
- Subjects
0106 biological sciences ,Ubiquitin proteasome system ,[SDV]Life Sciences [q-bio] ,Strigolactone ,Plant Development ,Biology ,01 natural sciences ,03 medical and health sciences ,Lactones ,Hormone signaling ,Shoot branching ,Molecular Biology ,030304 developmental biology ,Karrikins ,0303 health sciences ,Rhizosphere ,food and beverages ,Strigolactone biosynthesis ,Cell biology ,Biosynthetic Pathways ,Plant development ,Biochemistry ,Proteolysis ,Signal transduction ,Plant Shoots ,010606 plant biology & botany ,Developmental Biology ,Signal Transduction - Abstract
Strigolactones (SLs), first identified for their role in parasitic and symbiotic interactions in the rhizosphere, constitute the most recently discovered group of plant hormones. They are best known for their role in shoot branching but, more recently, roles for SLs in other aspects of plant development have emerged. In the last five years, insights into the SL biosynthetic pathway have also been revealed and several key components of the SL signaling pathway have been identified. Here, and in the accompanying poster, we summarize our current understanding of the SL pathway and discuss how this pathway regulates plant development.
- Published
- 2015
41. An efficient construction of bicyclic systems containing a seven-membered ring by tandem ring-closing metathesis reactions of dienynes
- Author
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François-Didier Boyer, Issam Hanna, Unité de Phytopharmacie et Médiateurs Chimiques, INRA, Versailles, France, affiliation inconnue, Laboratoire de synthèse organique (DCSO), and École polytechnique (X)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
- Subjects
Tandem ,Bicyclic molecule ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,010405 organic chemistry ,Stereochemistry ,Organic Chemistry ,General Medicine ,Conjugated system ,010402 general chemistry ,Metathesis ,Ring (chemistry) ,Medicinal chemistry ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,Inorganic Chemistry ,chemistry.chemical_compound ,Ring-closing metathesis ,chemistry ,Salt metathesis reaction ,Materials Chemistry ,Physical and Theoretical Chemistry ,Methyl group - Abstract
International audience; Various (5-7) and (6-7) bicyclic dienes bearing quaternary methyl group and ester functionality have been synthesized from acyclic dienynes by tandem ring-closing metathesis (RCM) reaction. Epoxidation of these conjugated dienes led to bicyclic vinyl oxiranes which undergo acid-catalyzed addition of alcohols to afford highly oxygenated compounds. © 2006 Elsevier B.V. All rights reserved.
- Published
- 2006
42. Hydroxylation of Ring A of Flavan-3-ols: Influence of the Ring A Substitution Pattern on the Oxidative Rearrangement of 6-Hydroxyflavan-3-ols
- Author
-
François-Didier Boyer, Paul-Henri Ducrot, Josiane Beauhaire, Marie Thérèse Martin, Institut Jean-Pierre Bourgin (IJPB), Institut National de la Recherche Agronomique (INRA)-AgroParisTech, Centre National de la Recherche Scientifique (CNRS), Institut de Chimie des Substances Naturelles (ICSN), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)
- Subjects
Stereochemistry ,[SDV]Life Sciences [q-bio] ,phenols ,Oxidative phosphorylation ,010402 general chemistry ,Ring (chemistry) ,01 natural sciences ,Redox ,Catalysis ,Hydroxylation ,chemistry.chemical_compound ,Flavan ,[SDV.IDA]Life Sciences [q-bio]/Food engineering ,dioxiranes ,rearrangements ,[SDV.BV]Life Sciences [q-bio]/Vegetal Biology ,[SPI.GPROC]Engineering Sciences [physics]/Chemical and Process Engineering ,Phenols ,ComputingMilieux_MISCELLANEOUS ,quinones ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,010405 organic chemistry ,Organic Chemistry ,Substitution (logic) ,oxidations ,Catechin ,0104 chemical sciences ,chemistry - Abstract
International audience; A general procedure for the oxidation of catechin derivatives is described, leading to the introduction of a new hydroxyl group at C-6. This procedure has been used for the synthesis of a number of 6-hydroxy flavan-3-ols, including elephantorrhizol, a natural flavan-3-ol exhibiting a fully substituted A ring. The substitution at C-8, albeit of poor influence on the course of this oxidation reaction, has been demonstrated to be preponderant for the further spontaneous oxidation and rearrangement of 6-hydroxy-flavan-3-ols into p-benzoquinones. The whole procedure allows the preparation of 6-alkyl substituted benzoquinones derived from catechin.
- Published
- 2006
43. Hydrogenation of substituted aromatic aldehydes: nucleophilic trapping of the reaction intermediate, application to the efficient synthesis of methylene linked flavanol dimers
- Author
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Paul-Henri Ducrot, François-Didier Boyer, Unité de phytopharmacie et médiateurs chimiques, and Institut National de la Recherche Agronomique (INRA)
- Subjects
010405 organic chemistry ,Chemistry ,Organic Chemistry ,Trapping ,Reaction intermediate ,010402 general chemistry ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,chemistry.chemical_compound ,Nucleophile ,[SDV.IDA]Life Sciences [q-bio]/Food engineering ,Drug Discovery ,Organic chemistry ,[SPI.GPROC]Engineering Sciences [physics]/Chemical and Process Engineering ,Methylene - Abstract
The synthesis of dimeric flavanols is the consequence of the possible trapping of the reaction intermediates generated in the course of the reductive hydrogenation of substituted benzaldehydes. The scope of this reaction is investigated.
- Published
- 2005
44. Synthesis of modified proanthocyanidins: introduction of acyl substituents at C-8 of catechin. Selective synthesis of a C-4→O→C-3 ether-linked procyanidin-like dimer
- Author
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Paul-Henri Ducrot, Josiane Beauhaire, Nour-Eddine Es-Safi, Lucien Kerhoas, François-Didier Boyer, Christine Le Guerneve, Unité de phytopharmacie et médiateurs chimiques, Institut National de la Recherche Agronomique (INRA), Sciences Pour l'Oenologie (SPO), Institut national d’études supérieures agronomiques de Montpellier (Montpellier SupAgro), and Institut national d'enseignement supérieur pour l'agriculture, l'alimentation et l'environnement (Institut Agro)-Institut national d'enseignement supérieur pour l'agriculture, l'alimentation et l'environnement (Institut Agro)-Université Montpellier 1 (UM1)-Université de Montpellier (UM)-Institut National de la Recherche Agronomique (INRA)
- Subjects
Stereochemistry ,[SDV]Life Sciences [q-bio] ,Dimer ,Clinical Biochemistry ,Pharmaceutical Science ,Ether ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Chemical synthesis ,Antioxidants ,Catechin ,Adduct ,chemistry.chemical_compound ,[SDV.IDA]Life Sciences [q-bio]/Food engineering ,Drug Discovery ,Biflavonoids ,Proanthocyanidins ,[SPI.GPROC]Engineering Sciences [physics]/Chemical and Process Engineering ,Molecular Biology ,010405 organic chemistry ,Organic Chemistry ,Regioselectivity ,0104 chemical sciences ,Proanthocyanidin ,chemistry ,Polyphenol ,Molecular Medicine ,Dimerization - Abstract
The regioselective introduction of substituents at C-8 of (+)-catechin is described, leading to the synthesis of several catechin derivatives with various substitution patterns to be used for the further synthesis of modified proanthocyanidins. Thereafter, a new 3-O-4 ether-linked procyanidin-like derivative was synthesized. Its formation was selectively achieved through TiCl(4)-catalyzed condensation of 4-(2-hydroxyethoxy)tetra-O-benzyl catechin with the 8-trifluoroacetyl adduct of tetra-O-benzyl catechin.
- Published
- 2005
45. Synthesis of agarofuran antifeedants. Part 6: Enantioselective synthesis of a key decalinic intermediate
- Author
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Thierry Prangé, Paul-Henri Ducrot, François-Didier Boyer, Unité de phytopharmacie et médiateurs chimiques, and Institut National de la Recherche Agronomique (INRA)
- Subjects
[SDV.EE]Life Sciences [q-bio]/Ecology, environment ,010405 organic chemistry ,Stereochemistry ,Organic Chemistry ,Enantioselective synthesis ,010402 general chemistry ,01 natural sciences ,Catalysis ,0104 chemical sciences ,Inorganic Chemistry ,chemistry.chemical_compound ,Decalin ,chemistry ,Cyclohexenone ,Furan ,Organic chemistry ,Moiety ,Lewis acids and bases ,Physical and Theoretical Chemistry ,SYNTHESE - Abstract
The asymmetric synthesis of a template decalin precursor in the synthesis of polyhydroxylated agarofuran sesquiterpenes is described via a Lewis acid catalysed addition of furan to an activated cyclohexenone directed by an adjacent chiral ketal moiety.
- Published
- 2003
46. Synthesis of a highly functionalized tricyclic ring system related to guanacastepene via a tandem ring-closing metathesis reaction
- Author
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Issam Hanna, François-Didier Boyer, Unité de phytopharmacie et médiateurs chimiques, Institut National de la Recherche Agronomique (INRA), Laboratoire de synthèse organique (DCSO), École polytechnique (X)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and École polytechnique (X)-Centre National de la Recherche Scientifique (CNRS)
- Subjects
Tandem ,010405 organic chemistry ,Stereochemistry ,Chemistry ,Organic Chemistry ,General Medicine ,Guanacastepene ,010402 general chemistry ,Ring (chemistry) ,Combinatorial chemistry ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,Ring-closing metathesis ,[SDV.IDA]Life Sciences [q-bio]/Food engineering ,Drug Discovery ,Salt metathesis reaction ,[SPI.GPROC]Engineering Sciences [physics]/Chemical and Process Engineering ,SYNTHESE - Abstract
25 ref. DOI:10.1016/S0040-4039(02)01793-8; International audience; A new approach to a highly functionalized 5,7,6-tricyclic core structure of guanacastepene has been developed using the tandem ring-closing metathesis reaction of dienynes as the key step. © 2002 Elsevier Science Ltd. All rights reserved.
- Published
- 2002
47. New strigolactone analogs as plant hormones with low activities in the rhizosphere
- Author
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Sofie Goormachtig, François-Didier Boyer, Nicolas Frei dit Frey, Jean-Paul Pillot, Catherine Rameau, Danny Geelen, Guillaume Clavé, Christian V. Stevens, Thomas S. A. Heugebaert, Amélie Roux, Jean-Bernard Pouvreau, Alexandre de Saint Germain, Stephen Depuydt, Dominique Lauressergues, Amanda Rasmussen, Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Department of Plant Production [Ghent], Faculty of Bioscience Engineering [Ghent], Universiteit Gent = Ghent University [Belgium] (UGENT)-Universiteit Gent = Ghent University [Belgium] (UGENT), Center for Plant Systems Biology (PSB Center), Vlaams Instituut voor Biotechnologie [Ghent, Belgique] (VIB), Institut National de la Recherche Agronomique (INRA), Agence Nationale de la Recherche [ANR-12-BSV6-004-01], Marie Curie International Incoming Fellowship, Newton International Fellowship, and Fund for Scientific Research Flanders (FWO Vlaanderen)
- Subjects
Hyphal growth ,Gigaspora rosea ,plant growth regulator ,Mutant ,Arabidopsis ,Strigolactone ,Plant Science ,strigolactones ,Lactones ,Plant Growth Regulators ,Gene Expression Regulation, Plant ,root parasitic plants ,Botany ,Glomeromycota ,Molecular Biology ,Pisum sativum ,synthetic analogs ,Rhizosphere ,biology ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,fungi ,food and beverages ,biology.organism_classification ,Germination ,Plant hormone ,Weed - Abstract
International audience; : Strigolactones (SLs) are known not only as plant hormones, but also as rhizosphere signals for establishing symbiotic and parasitic interactions. The design of new specific SL analogs is a challenging goal in understanding the basic plant biology and is also useful to control plant architectures without favoring the development of parasitic plants. Two different molecules (23 (3'-methyl-GR24), 31 (thia-3'-methyl-debranone-like molecule)) already described, and a new one (AR36), for which the synthesis is presented, are biologically compared with the well-known GR24 and the recently identified CISA-1. These different structures emphasize the wide range of parts attached to the D-ring for the bioactivity as a plant hormone. These new compounds possess a common dimethylbutenolide motif but their structure varies in the ABC part of the molecules: 23 has the same ABC part as GR24, while 31 and AR36 carry, respectively, an aromatic ring and an acyclic carbon chain. Detailed information is given for the bioactivity of such derivatives in strigolactone synthesis or in perception mutant plants (pea rms1 and rms4, Arabidopsis max2 and, max4) for different hormonal functions along with their action in the rhizosphere on arbuscular mycorrhizal hyphal growth and parasitic weed germination.
- Published
- 2014
48. Strigolactones Inhibit Caulonema Elongation and Cell Division in the Moss Physcomitrella patens
- Author
-
Katia Belcram, Helene Proust, Sandrine Bonhomme, Cécile Labrune, François-Didier Boyer, Catherine Rameau, Beate Hoffmann, Institut Jean-Pierre Bourgin (IJPB), Institut National de la Recherche Agronomique (INRA)-AgroParisTech, Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Bonhomme, Sandrine, and Centre National de la Recherche Scientifique (CNRS)
- Subjects
0106 biological sciences ,Cell division ,Light ,Plant Evolution ,Mutant ,lcsh:Medicine ,Plant Science ,division cellulaire ,01 natural sciences ,Lactones ,Plant Growth Regulators ,Molecular Cell Biology ,Cell Cycle and Cell Division ,Protonema ,lcsh:Science ,Plant Proteins ,Plant Growth and Development ,physcomitrella patens ,0303 health sciences ,Rhizosphere ,Multidisciplinary ,biology ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,Cell biology ,Cell Processes ,Signal transduction ,Research Article ,Plant Cell Biology ,Bryophyta ,Flowers ,Physcomitrella patens ,Research and Analysis Methods ,Cell Growth ,03 medical and health sciences ,Model Organisms ,Plant and Algal Models ,Plant Cells ,Botany ,030304 developmental biology ,Evolutionary Biology ,lcsh:R ,Biology and Life Sciences ,Cell Biology ,biology.organism_classification ,Plant cell ,Moss ,Organismal Evolution ,arabidopsis ,mousse ,germination ,Mutation ,lcsh:Q ,010606 plant biology & botany ,Developmental Biology ,hormone végétale - Abstract
International audience; : In vascular plants, strigolactones (SLs) are known for their hormonal role and for their role as signal molecules in the rhizosphere. SLs are also produced by the moss Physcomitrella patens, in which they act as signaling factors for controlling filament extension and possibly interaction with neighboring individuals. To gain a better understanding of SL action at the cellular level, we investigated the effect of exogenously added molecules (SLs or analogs) in moss growth media. We used the previously characterized Ppccd8 mutant that is deficient in SL synthesis and showed that SLs affect moss protonema extension by reducing caulonema cell elongation and mainly cell division rate, both in light and dark conditions. Based on this effect, we set up bioassays to examine chemical structure requirements for SL activity in moss. The results suggest that compounds GR24, GR5, and 5-deoxystrigol are active in moss (as in pea), while other analogs that are highly active in the control of pea branching show little activity in moss. Interestingly, the karrikinolide KAR1, which shares molecular features with SLs, did not have any effect on filament growth, even though the moss genome contains several genes homologous to KAI2 (encoding the KAR1 receptor) and no canonical homologue to D14 (encoding the SL receptor). Further studies should investigate whether SL signaling pathways have been conserved during land plant evolution.
- Published
- 2014
49. Chapter 7. Recent results in synthetic glycochemistry with iron salts at Orsay-Gif
- Author
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Amandine Xolin, Gilles Doisneau, Aurélie Mathieu, Aurélie Lemétais, Jean-François Soulé, Jean-Marie Beau, Boris Vauzeilles, François-Didier Boyer, Stephanie Norsikian, Dominique Urban, Arnaud Stévenin, Alexandra Gouasmat, and Yann Bourdreux
- Subjects
chemistry.chemical_classification ,Glycosylation ,Double bond ,010405 organic chemistry ,Chemistry ,Dihydropyran ,Regioselectivity ,Oxazoline ,010402 general chemistry ,01 natural sciences ,0104 chemical sciences ,chemistry.chemical_compound ,Electrophile ,Organic chemistry ,Lewis acids and bases ,Trifluoromethanesulfonate - Abstract
This review particularly emphasizes synthetic applications resulting from cascade or one-pot transformations and a glycosylation reaction promoted by ferric salts. These easy to handle, cheap and environment-friendly salts have been examined for their ability to induce, as a Lewis acid, fast carbohydrate-based modifications in our laboratories at Orsay and Gif sur Yvette. A short synthetic route to the dihydropyran framework of anti-influenza constructs is reported by coupling the Petasis three-component condensation to an iron(iii)-promoted one-pot cascade of deprotection – C–C double bond isomerization – cyclization - oxazoline formation. We also show that iron(iii) chloride hexahydrate is most appropriate to catalyze a one-pot regioselective protection of mono- and disaccharides. This iron(iii) catalysis renders multi-step routes, such as chemical oligosaccharide syntheses, faster. In the last section, we report a catalytic glycosylation method particularly simple and straightforward leading to the important β-d-GlcNAc motif, in which the more electrophilic iron(iii) triflate activates the readily available peracetate of N-acetyl-β-d-glucosamine. This glycosylation does not necessarily require the formation of the mandatory oxazolinium intermediate.
- Published
- 2014
50. Synthesis of Polyoxygenated Bicyclic Systems Containing Medium-Sized Rings from Carbohydrates via Tandem Metathesis of Dienynes
- Author
-
Louis Ricard, Issam Hanna, François-Didier Boyer, Unité de phytopharmacie et médiateurs chimiques, and Institut National de la Recherche Agronomique (INRA)
- Subjects
Tandem ,Bicyclic molecule ,010405 organic chemistry ,Chemistry ,Stereochemistry ,Organic Chemistry ,Carbohydrates ,Crystallography, X-Ray ,010402 general chemistry ,Ring (chemistry) ,Metathesis ,01 natural sciences ,Biochemistry ,Combinatorial chemistry ,0104 chemical sciences ,Oxygen ,Bridged Bicyclo Compounds ,[SDV.IDA]Life Sciences [q-bio]/Food engineering ,[SPI.GPROC]Engineering Sciences [physics]/Chemical and Process Engineering ,Physical and Theoretical Chemistry ,Oxidation-Reduction - Abstract
[reaction: see text] Highly functionalized (5-7), (5-8), and (6-8) ring systems have been prepared from carbohydrates via tandem ring-closing metathesis of dienynes.
- Published
- 2001
Catalog
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