title: Chemical dereplication of wine stilbenoids using high performance liquid chromatography-nuclear magnetic resonance spectroscopy.
abstract: Wine is a major dietary source of numerous potentially health promoting stilbenoids that have been the subject of many qualitative and quantitative studies. However, our initial HPLC-MS analyses of crude wine samples demonstrated the presence of compounds with molecular weights matching characteristic stilbenoid dimers, trimers, and tetramers that were unaccounted for in the literature. Due to the likelihood that these are known compounds, a chemical dereplication method is highly desirable. We developed such a method using LC-DAD-MS monitored fractionation steps, using adsorption and centrifugal partition chromatography (CPC), to obtain fractions rich in stilbenoids for analysis in stopped-flow LC-NMR. (1)H NMR spectra and MS data were cross-referenced with our laboratory database and the literature for identification. This method yielded highly useful structural information, allowing the characterization of previously unidentified stilbenoids in wine, ampelopsin C, isohopeaphenol, quadrangularin A, and E-ω-viniferin. These results demonstrate the usefulness of stop-flow LC-NMR in conjunction with LC-MS guided fractionation for the dereplication of compounds of interest in general, and specifically for expanding the current knowledge of wine chemistry.
authors.affiliation: Université de Bordeaux, ISVV, Groupe d'Etude des Substances Végétales à Activité Biologique, EA 3675, F-33140 Villenave d'Ornon, France.
authors.forename: Alison D
authors.initials: AD
authors.lastname: Pawlus
authors.forename: Emma
authors.initials: E
authors.lastname: Cantos-Villar
authors.forename: Tristan
authors.initials: T
authors.lastname: Richard
authors.forename: Jonathan
authors.initials: J
authors.lastname: Bisson
authors.forename: Pascal
authors.initials: P
authors.lastname: Poupard
authors.forename: Yorgos
authors.initials: Y
authors.lastname: Papastamoulis
authors.forename: Jean-Pierre
authors.initials: JP
authors.lastname: Monti
authors.forename: Pierre-Louis
authors.initials: PL
authors.lastname: Teissedre
authors.forename: Pierre
authors.initials: P
authors.lastname: Waffo-Téguo
authors.forename: Jean-Michel
authors.initials: JM
authors.lastname: Mérillon
mesh_terms: D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D013058:Mass Spectrometry; D013267:Stilbenes / Q000032:analysis*; D014920:Wine / Q000032:analysis*
chemical_list: D013267:Stilbenes