Characterization of a colorless anthocyanin-flavan-3-ol dimer containing both carbon-carbon and ether interflavanoid linkages by NMR and mass spectrometry

Journal of Agricultural and Food Chemistry
Sophie Remy-TanneauV Cheynier

Abstract

Direct addition of anthocyanins and flavan-3-ols was investigated in a model system by incubating malvidin 3-glucoside and (-)-epicatechin in ethanol. Analysis of reaction products by high-performance liquid chromatography coupled to electrospray ionization mass spectrometry (HPLC/ESI-MS) before and after thiolysis showed the formation of colorless dimers detected at m/z 781 in the negative ion mode, with retention times and spectroscopic characteristics identical to those of compounds detected in wine, which contain one malvidin 3-glucoside unit and one flavanol unit. On the basis of their resistance to thiolysis, these compounds were postulated to be bicyclic dimers linked with both carbon-carbon and ether bonds as observed in the case of A type proanthocyanidins. The major dimer analyzed by NMR experiments was identified as malvidin 3-glucoside(C2-O-C7,C4-C8)epicatechin, confirming this hypothesis. A similar assay was performed with (+)-catechin instead of (-)-epicatechin, and the formation of bicyclic dimers was also observed.

References

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Citations

Feb 12, 2013·Analytical and Bioanalytical Chemistry·Christian G KruegerAmy B Howell
Sep 13, 2005·Phytochemistry·De-Yu Xie, Richard A Dixon
Jan 17, 2012·Journal of Agricultural and Food Chemistry·Luke R HowardJackson O Lay
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Dec 5, 2008·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Fei HeChang-Qing Duan
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Feb 6, 2017·Current Pharmaceutical Design·Maria Rosa Perez-Gregorio, Jesus Simal-Gandara
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Jan 13, 2021·Foods·Marko ViskićAna Jeromel
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Oct 11, 2007·Journal of Agricultural and Food Chemistry·Andrew P NeilsonMario G Ferruzzi
Nov 13, 2004·Journal of Agricultural and Food Chemistry·Stéphane VidalYoji Hayasaka

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