201. Biosynthetic investigation of γ-lactones in Sextonia rubra wood using in situ TOF-SIMS MS/MS imaging to localize and characterize biosynthetic intermediates
- Author
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Tingting Fu, Christophe Duplais, Nadine Amusant, Serge Della-Negra, Gregory L. Fisher, Grégory Genta-Jouve, Alain Brunelle, Emeline Houël, David Touboul, Duplais, Christophe, Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS), Ecologie des forêts de Guyane (UMR ECOFOG), Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut National de la Recherche Agronomique (INRA)-AgroParisTech-Université de Guyane (UG)-Centre National de la Recherche Scientifique (CNRS)-Université des Antilles (UA), Ecologie des forêts de Guyane (ECOFOG), Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut National de la Recherche Agronomique (INRA)-Université des Antilles et de la Guyane (UAG)-AgroParisTech-Centre National de la Recherche Scientifique (CNRS), Equipe Pharmacognosie (UMR 8638), Chimie Organique, Médicinale et Extractive et Toxicologie Expérimentale (COMETE - UMR 8638), Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS)-Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS), UMR8608, ANR-15-CE29-0007,DEFIMAGE,Un grand défi pour l'imagerie par spectrométrie de masse(2015), ANR-10-LABX-0025,CEBA,CEnter of the study of Biodiversity in Amazonia(2010), Université Paris-Sud - Paris 11 (UP11), Institut de Physique Nucléaire d'Orsay (IPNO), Centre National de la Recherche Scientifique (CNRS)-Institut National de Physique Nucléaire et de Physique des Particules du CNRS (IN2P3)-Université Paris-Sud - Paris 11 (UP11), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Université Paris Descartes - Paris 5 (UPD5), Physical electronics (PHI), Agence Nationale de la Recherche (France) [ANR-2015-CE29-0007-01 DEFIMAGE], 'Investissement d'Avenir' grant [ANR-10-LABX-25-01], China Scholarship Council (CSC) [201406310013], and Université Paris-Sud - Paris 11 (UP11)-Institut National de Physique Nucléaire et de Physique des Particules du CNRS (IN2P3)-Centre National de la Recherche Scientifique (CNRS)
- Subjects
K50 - Technologie des produits forestiers ,0301 basic medicine ,In situ ,Metabolite ,lcsh:Medicine ,butanolides ,Tandem mass spectrometry ,ion mass-spectrometry ,chemistry.chemical_compound ,Acetals ,0302 clinical medicine ,Tandem Mass Spectrometry ,lcsh:Science ,constituents ,metabolites ,ComputingMilieux_MISCELLANEOUS ,Cellular localization ,[PHYS]Physics [physics] ,alkene-alkyne pair ,stem wood ,rubrenolide ,heartwood ,rubrynolide ,resolution ,Multidisciplinary ,Chemistry ,Composition chimique ,Wood ,Biochemistry ,Alkynes ,[CHIM.CHEM]Chemical Sciences/Cheminformatics ,Resolution (mass spectrometry) ,F60 - Physiologie et biochimie végétale ,Alkenes ,Sextonia rubra ,Article ,Bois ,Lauraceae ,03 medical and health sciences ,Polyketide ,[CHIM.ANAL]Chemical Sciences/Analytical chemistry ,lcsh:R ,Metabolic pathway ,030104 developmental biology ,lcsh:Q ,030217 neurology & neurosurgery - Abstract
Molecular analysis by parallel tandem mass spectrometry (MS/MS) imaging contributes to the in situ characterization of biosynthetic intermediates which is crucial for deciphering the metabolic pathways in living organisms. We report the first use of TOF-SIMS MS/MS imaging for the cellular localization and characterization of biosynthetic intermediates of bioactive γ-lactones rubrynolide and rubrenolide in the Amazonian tree Sextonia rubra (Lauraceae). Five γ-lactones, including previously reported rubrynolide and rubrenolide, were isolated using a conventional approach and their structural characterization and localization at a lateral resolution of ~400 nm was later achieved using TOF-SIMS MS/MS imaging analysis. 2D/3D MS imaging at subcellular level reveals that putative biosynthetic γ-lactones intermediates are localized in the same cell types (ray parenchyma cells and oil cells) as rubrynolide and rubrenolide. Consequently, a revised metabolic pathway of rubrynolide was proposed, which involves the reaction between 2-hydroxysuccinic acid and 3-oxotetradecanoic acid, contrary to previous studies suggesting a single polyketide precursor. Our results provide insights into plant metabolite production in wood tissues and, overall, demonstrate that combining high spatial resolution TOF-SIMS imaging and MS/MS structural characterization offers new opportunities for studying molecular and cellular biochemistry in plants.
- Published
- 2019