title: 13C NMR and LC-MS Profiling of Stilbenes from Elicited Grapevine Hairy Root Cultures.
abstract: Resveratrol and related oligostilbenes are defense molecules produced by grapevine in response to stresses including various elicitors or signal molecules. Together with their prominent role in planta, these compounds have been the center of much attention in recent decades due to their pharmacological properties. The cost-effective production of resveratrol derivatives such as viniferins or more structurally complex stilbene oligomers remains a challenging task. In this study, the chemical diversity of stilbenes produced by Vitis vinifera Pinot Noir hairy roots was investigated after elicitation for 4 days with a mixture of methyl jasmonate (100 μM) and cyclodextrins (50 mM). Two crude extracts obtained from the culture medium and from the hairy roots were fractionated by centrifugal partition chromatography. The fractions were chemically investigated by two complementary identification approaches involving a13C NMR-based dereplication method and liquid chromatography coupled to mass spectrometry (LC-MS). In total, groups of 21 and 18 molecules, including flavonoids and stilbenes, were detected in the culture medium and root extracts, respectively. These included resveratrol monomers, dimers, trimers, and a tetramer, thus highlighting the ability of elicited hairy root culture systems to synthesize a wide diversity of secondary metabolites of pharmaceutical significance. The main compounds were unambiguously identified as trans-resveratrol, ε-viniferin, trans-piceatannol, pallidol, scirpusin A, eriodictyol, naringenin, vitisin B, and maackin.
authors.affiliation: Unité de Recherche Vignes et Vins de Champagne EA 4707, SFR Condorcet FR CNRS 3417, Université de Reims Champagne-Ardenne, UFR Sciences Exactes et Naturelles , BP 1039, 51687 Reims Cedex 2, France.|Laboratoire de Biologie des Plantes & Innovation EA 3900, SFR Condorcet FR CNRS 3417, Université de Picardie Jules Verne, UFR de Sciences, Ilot des Poulies , 33 Rue Saint Leu, 80039 Amiens Cedex, France.
authors.forename: Leo-Paul
authors.initials: LP
authors.lastname: Tisserant
authors.affiliation: Institut de Chimie Moléculaire de Reims UMR CNRS 7312, SFR Cap 'Santé, Université de Reims Champagne-Ardenne , BP 1039, 51687 Reims Cedex 2, France.
authors.forename: Jane
authors.initials: J
authors.lastname: Hubert
authors.affiliation: Laboratoire de Biologie des Plantes & Innovation EA 3900, SFR Condorcet FR CNRS 3417, Université de Picardie Jules Verne, UFR de Sciences, Ilot des Poulies , 33 Rue Saint Leu, 80039 Amiens Cedex, France.
authors.forename: Michelle
authors.initials: M
authors.lastname: Lequart
authors.affiliation: Institut de Chimie Moléculaire de Reims UMR CNRS 7312, SFR Cap 'Santé, Université de Reims Champagne-Ardenne , BP 1039, 51687 Reims Cedex 2, France.
authors.forename: Nicolas
authors.initials: N
authors.lastname: Borie
authors.affiliation: Institut de Chimie Moléculaire de Reims UMR CNRS 7312, SFR Cap 'Santé, Université de Reims Champagne-Ardenne , BP 1039, 51687 Reims Cedex 2, France.
authors.forename: Nicolas
authors.initials: N
authors.lastname: Maurin
authors.affiliation: Plateforme Analytique, SFR Condorcet FR CNRS 3417, Université de Picardie Jules Verne, UFR des Sciences , Bâtiment Serres-Transfert Rue Dallery-Passage du Sourire d'Avril, 80039 Amiens Cedex 1, France.
authors.forename: Serge
authors.initials: S
authors.lastname: Pilard
authors.affiliation: Unité de Recherche Vignes et Vins de Champagne EA 4707, SFR Condorcet FR CNRS 3417, Université de Reims Champagne-Ardenne, UFR Sciences Exactes et Naturelles , BP 1039, 51687 Reims Cedex 2, France.
authors.forename: Philippe
authors.initials: P
authors.lastname: Jeandet
authors.affiliation: Unité de Recherche Vignes et Vins de Champagne EA 4707, SFR Condorcet FR CNRS 3417, Université de Reims Champagne-Ardenne, UFR Sciences Exactes et Naturelles , BP 1039, 51687 Reims Cedex 2, France.
authors.forename: Aziz
authors.initials: A
authors.lastname: Aziz
authors.affiliation: Institut de Chimie Moléculaire de Reims UMR CNRS 7312, SFR Cap 'Santé, Université de Reims Champagne-Ardenne , BP 1039, 51687 Reims Cedex 2, France.
authors.forename: Jean-Hugues
authors.initials: JH
authors.lastname: Renault
authors.affiliation: Institut de Chimie Moléculaire de Reims UMR CNRS 7312, SFR Cap 'Santé, Université de Reims Champagne-Ardenne , BP 1039, 51687 Reims Cedex 2, France.
authors.forename: Jean-Marc
authors.initials: JM
authors.lastname: Nuzillard
authors.affiliation: Unité de Recherche Vignes et Vins de Champagne EA 4707, SFR Condorcet FR CNRS 3417, Université de Reims Champagne-Ardenne, UFR Sciences Exactes et Naturelles , BP 1039, 51687 Reims Cedex 2, France.
authors.forename: Christophe
authors.initials: C
authors.lastname: Clément
authors.affiliation: Laboratoire de Biologie des Plantes & Innovation EA 3900, SFR Condorcet FR CNRS 3417, Université de Picardie Jules Verne, UFR de Sciences, Ilot des Poulies , 33 Rue Saint Leu, 80039 Amiens Cedex, France.
authors.forename: Michèle
authors.initials: M
authors.lastname: Boitel-Conti
authors.affiliation: Unité de Recherche Vignes et Vins de Champagne EA 4707, SFR Condorcet FR CNRS 3417, Université de Reims Champagne-Ardenne, UFR Sciences Exactes et Naturelles , BP 1039, 51687 Reims Cedex 2, France.
authors.forename: Eric
authors.initials: E
authors.lastname: Courot
mesh_terms: D001572:Benzofurans / Q000032:analysis / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D002853:Chromatography, Liquid; D003517:Cyclopentanes / Q000494:pharmacology; D044950:Flavanones / Q000032:analysis; D005419:Flavonoids / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D054883:Oxylipins / Q000494:pharmacology; D010636:Phenols / Q000032:analysis / Q000737:chemistry; D018517:Plant Roots / Q000737:chemistry; D011083:Polycyclic Compounds / Q000032:analysis / Q000737:chemistry; D000077185:Resveratrol; D013267:Stilbenes / Q000032:analysis* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D027843:Vitis / Q000737:chemistry*
chemical_list: D001572:Benzofurans; D003517:Cyclopentanes; D044950:Flavanones; D005419:Flavonoids; D054883:Oxylipins; D010636:Phenols; D011083:Polycyclic Compounds; D013267:Stilbenes; C480486:malvidin-3-O-glucoside-4 vinyl; C535072:pallidol; C550387:scirpusin A; C091891:epsilon-viniferin; C041525:3,3',4,5'-tetrahydroxystilbene; C005273:naringenin; D000077185:Resveratrol; C007619:eriodictyol