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

Alison D. Pawlus; Emma Cantos-Villar; Tristan Richard; Jonathan Bisson; Pascal Poupard; Yorgos Papastamoulis; Jean Pierre Monti; Pierre Louis Teissedre; Pierre Waffo-Téguo; Jean Michel Mérillon

doi:10.1016/j.chroma.2013.03.010

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

Alison D. Pawlus
, Emma Cantos-Villar
, Tristan Richard
, Jonathan Bisson
, Pascal Poupard
, Yorgos Papastamoulis
, Jean Pierre Monti
, Pierre Louis Teissedre
, Pierre Waffo-Téguo
, Jean Michel Mérillon

Horticultural Science

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

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. 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.

Original language	English (US)
Pages (from-to)	19-26
Number of pages	8
Journal	Journal of Chromatography A
Volume	1289
DOIs	https://doi.org/10.1016/j.chroma.2013.03.010
State	Published - May 10 2013

Bibliographical note

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.

Keywords

Centrifugal partition chromatography
E-ω-viniferin
Isohopeaphenol
LC-NMR
Stilbenoid
Wine

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10.1016/j.chroma.2013.03.010

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Pawlus, A. D., Cantos-Villar, E., Richard, T., Bisson, J., Poupard, P., Papastamoulis, Y., Monti, J. P., Teissedre, P. L., Waffo-Téguo, P., & Mérillon, J. M. (2013). Chemical dereplication of wine stilbenoids using high performance liquid chromatography-nuclear magnetic resonance spectroscopy. Journal of Chromatography A, 1289, 19-26. https://doi.org/10.1016/j.chroma.2013.03.010

Pawlus, AD, Cantos-Villar, E, Richard, T, Bisson, J, Poupard, P, Papastamoulis, Y, Monti, JP, Teissedre, PL, Waffo-Téguo, P & Mérillon, JM 2013, 'Chemical dereplication of wine stilbenoids using high performance liquid chromatography-nuclear magnetic resonance spectroscopy', Journal of Chromatography A, vol. 1289, pp. 19-26. https://doi.org/10.1016/j.chroma.2013.03.010

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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. 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.",

keywords = "Centrifugal partition chromatography, E-ω-viniferin, Isohopeaphenol, LC-NMR, Stilbenoid, Wine",

author = "Pawlus, \{Alison D.\} and Emma Cantos-Villar and Tristan Richard and Jonathan Bisson and Pascal Poupard and Yorgos Papastamoulis and Monti, \{Jean Pierre\} and Teissedre, \{Pierre Louis\} and Pierre Waffo-T{\'e}guo and M{\'e}rillon, \{Jean Michel\}",

note = "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.",

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doi = "10.1016/j.chroma.2013.03.010",

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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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SN - 0021-9673

VL - 1289

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JF - Journal of Chromatography A

ER -

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

Abstract

Bibliographical note

Keywords

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