TY - JOUR
T1 - Chemical dereplication of wine stilbenoids using high performance liquid chromatography-nuclear magnetic resonance spectroscopy
AU - Pawlus, Alison D.
AU - Cantos-Villar, Emma
AU - Richard, Tristan
AU - Bisson, Jonathan
AU - Poupard, Pascal
AU - Papastamoulis, Yorgos
AU - Monti, Jean Pierre
AU - Teissedre, Pierre Louis
AU - Waffo-Téguo, Pierre
AU - Mérillon, Jean Michel
N1 - Funding Information:
The authors wish to thank the Fulbright Research Scholar in Aquitaine Regional Program for the grant provided to Alison D. Pawlus and to Domaine Henri Naudin-Ferrand for kindly providing the wine for this study. We also wish to thank Prof. Fulvio Mattivi for providing us with 1 H NMR spectra of stilbenoids.
PY - 2013/5/10
Y1 - 2013/5/10
N2 - 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.
AB - 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.
KW - Centrifugal partition chromatography
KW - E-ω-viniferin
KW - Isohopeaphenol
KW - LC-NMR
KW - Stilbenoid
KW - Wine
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U2 - 10.1016/j.chroma.2013.03.010
DO - 10.1016/j.chroma.2013.03.010
M3 - Article
C2 - 23566915
AN - SCOPUS:84876306573
SN - 0021-9673
VL - 1289
SP - 19
EP - 26
JO - Journal of Chromatography A
JF - Journal of Chromatography A
ER -