Chemical dereplication of wine stilbenoids using high performance liquid chromatography–nuclear magnetic resonance spectroscopy

• Published in: Journal of Chromatography A Vol. 1289; pp. 19 - 26
• Main Authors: Pawlus, Alison D., Cantos-Villar, Emma, Richard, Tristan, Bisson, Jonathan, Poupard, Pascal, Papastamoulis, Yorgos, Monti, Jean-Pierre, Teissedre, Pierre-Louis, Waffo-Téguo, Pierre, Mérillon, Jean-Michel
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier B.V 10.05.2013; Elsevier
• Subjects: adsorption; Biological and medical sciences; Centrifugal partition chromatography; Chemical and Process Engineering; Chromatography, High Pressure Liquid - methods; countercurrent chromatography; E-ω-viniferin; Engineering Sciences; Fermented food industries; Food engineering; Food industries; fractionation; Fundamental and applied biological sciences. Psychology; high performance liquid chromatography; Isohopeaphenol; LC–NMR; Life Sciences; Magnetic Resonance Spectroscopy - methods; Mass Spectrometry; molecular weight; nuclear magnetic resonance spectroscopy; Stilbenes - analysis; Stilbenoid; stilbenoids; Wine; Wine - analysis; wines; Wines and vinegars; Wine; LC–NMR; Isohopeaphenol; Centrifugal partition chromatography; E-ω-viniferin; Stilbenoid; Countercurrent chromatography; Chemical analysis; HPLC chromatography; NMR spectrometry; Hydrogen 1; Stopped flow method; Resveratrol; Trimer; Fractionation; Coupled method; Preparative chromatography; LC-NMR; Stilbene derivatives; Reversed phase chromatography; Ultraviolet detector; Phytoalexin; Phenols; Isolation; Dimer; Benzofuran derivatives; Structural analysis; E-omega-viniferin
• ISSN: 0021-9673; 1873-3778
• DOI: 10.1016/j.chroma.2013.03.010

•An HPLC–NMR-based dereplication method for stilbenoids in wine was developed.•Stilbenoid rich fractions were obtained by CPC.•Four stilbenoids were identified in wine for the first time. 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. 1H 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.