Contalactone, a contaminant formed during chemical synthesis of the strigolactone reference GR24 is also a strigolactone mimic
2019
de Saint Germain, Alexandre | Retailleau, Pascal | Norsikian, Stéphanie | Servajean, Vincent | Pelissier, Franck | Steinmetz, Vincent | Pillot, Jean-Paul | Rochange, Soizic | Pouvreau, Jean-Bernard | Boyer, François-Didier | Institut Jean-Pierre Bourgin (IJPB) ; Institut National de la Recherche Agronomique (INRA)-AgroParisTech | Institut de Chimie des Substances Naturelles (ICSN) ; Institut de Chimie - CNRS Chimie (INC-CNRS)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS) | LRSV-Evolution des Interactions Plantes-Microorganismes (LRSV-EIPM) ; Laboratoire de Recherche en Sciences Végétales (LRSV) ; Université Toulouse III - Paul Sabatier (UT3) ; Université de Toulouse (UT)-Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Université Toulouse III - Paul Sabatier (UT3) ; Université de Toulouse (UT)-Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS) | Unité en Sciences Biologiques et Biotechnologies de Nantes (US2B) ; Centre National de la Recherche Scientifique (CNRS)-Nantes Université - UFR de Médecine et des Techniques Médicales (Nantes Univ - UFR MEDECINE) ; Nantes Université - pôle Santé ; Nantes Université (Nantes Univ)-Nantes Université (Nantes Univ)-Nantes Université - pôle Santé ; Nantes Université (Nantes Univ)-Nantes Université (Nantes Univ) | [ANR-10-LABX-0040-SPS, ANR-11-IDEX-0003-02]; EUEuropean Union (EU); TULIP LabEx [ANR-10-LABX-41]; CHARM3AT Labex program [ANR-11-LABX-39] | ANR-10-LABX-0040,SPS,Saclay Plant Sciences(2010) | ANR-11-IDEX-0003,IPS,Idex Paris-Saclay(2011)
International audience
显示更多 [+] 显示较少 [-]英语. Strigolactone (SL) plant hormones control plant architecture and are key players in both symbiotic and parasitic interactions. GR24, a synthetic SL analog, is the worldwide reference compound used in all bioassays for investigating the role of SLs in plant development and in rhizospheric interactions. In 2012, the first characterization of the SL receptor reported the detection of an unknown compound after incubation of GR24 samples with the SL receptor. We reveal here the origin of this compound (P270), which comes from a by-product formed during GR24 chemical synthesis. We present the identification of this by-product, named contalactone. A proposed chemical pathway for its formation is provided as well as an evaluation of its bioactivity on pea, Arabidopsis, root parasitic plant seeds and AM fungi, characterizing it as a SL mimic. Quality of GR24 samples can be easily checked by carrying out microscale hydrolysis in a basic aqueous medium to easily detect P270 as indicator of the presence of the contalactone impurity. In all cases, before being used for bioassays, GR24 must be careful purified by preparative HPLC.
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