Extraction, detection, and quantification of flavano-ellagitannins and ethylvescalagin in a Bordeaux red wine aged in oak barrels
- PMID: 16968104
- DOI: 10.1021/jf061724i
Extraction, detection, and quantification of flavano-ellagitannins and ethylvescalagin in a Bordeaux red wine aged in oak barrels
Abstract
An extraction procedure and an analytical method have been developed to detect and quantify for the first time a series of ellagitannin derivatives formed in wine during aging in oak barrels. The method involves a preliminary purification step on XAD7 HP resin followed by a second purification step on TSK 40 HW gel. The resulting extract is analyzed for compound identification and quantitative determination by high-performance liquid chromatography-electrospray ionization-mass spectrometry in single ion recording mode. Reference compounds, which are accessible through hemisynthesis from the oak C-glycosidic ellagitannin vescalagin, were used to build calibration curves, and chlorogenic acid was selected as an internal standard. This method enabled us to estimate the content of four flavano-ellagitannins and that of another newly identified wine polyphenol, beta-1-O-ethylvescalagin, in a Bordeaux red wine aged for 18 months in oak barrels. All five ellagitannin derivatives are derived from the nucleophilic substitution reaction of vescalagin with the grape flavan-3-ols catechin and epicatechin or ethanol.
Similar articles
-
Sanitization of Oak Barrels for Wine-A Review.J Agric Food Chem. 2020 May 13;68(19):5283-5295. doi: 10.1021/acs.jafc.0c00816. Epub 2020 May 4. J Agric Food Chem. 2020. PMID: 32323983 Review.
-
Impact of concentration of ellagitannins in oak wood on their levels and organoleptic influence in red wine.J Agric Food Chem. 2011 May 25;59(10):5677-83. doi: 10.1021/jf200275w. Epub 2011 Apr 27. J Agric Food Chem. 2011. PMID: 21480590
-
Identification, amounts, and kinetics of extraction of C-glucosidic ellagitannins during wine aging in oak barrels or in stainless steel tanks with oak chips.Anal Bioanal Chem. 2011 Sep;401(5):1531-9. doi: 10.1007/s00216-011-4949-8. Epub 2011 Apr 9. Anal Bioanal Chem. 2011. PMID: 21479542
-
Sensory-directed identification of taste-active ellagitannins in American (Quercus alba L.) and European oak wood (Quercus robur L.) and quantitative analysis in bourbon whiskey and oak-matured red wines.J Agric Food Chem. 2006 May 3;54(9):3380-90. doi: 10.1021/jf052617b. J Agric Food Chem. 2006. PMID: 16637699
-
Enzymology of gallotannin and ellagitannin biosynthesis.Phytochemistry. 2005 Sep;66(17):2001-11. doi: 10.1016/j.phytochem.2005.01.009. Phytochemistry. 2005. PMID: 16153405 Review.
Cited by
-
Evaluation and Comparison of Dermo-Cosmetic Activities of Three Oak Species by Targeting Antioxidant Metabolites and Skin Enzyme Inhibitors.Metabolites. 2023 Jun 28;13(7):804. doi: 10.3390/metabo13070804. Metabolites. 2023. PMID: 37512511 Free PMC article.
-
Identification of Unstable Ellagitannin Metabolites in the Leaves of Quercus dentata by Chemical Derivatization.Molecules. 2023 Jan 27;28(3):1246. doi: 10.3390/molecules28031246. Molecules. 2023. PMID: 36770911 Free PMC article.
-
Cork, a Natural Choice to Wine?Foods. 2022 Aug 30;11(17):2638. doi: 10.3390/foods11172638. Foods. 2022. PMID: 36076822 Free PMC article. Review.
-
Impact of Barrel Toasting on Ellagitannin Composition of Aged Cognac Eaux-de-Vie.Molecules. 2022 Apr 14;27(8):2531. doi: 10.3390/molecules27082531. Molecules. 2022. PMID: 35458728 Free PMC article.
-
Role of Oak Ellagitannins in the Synthesis of Vitisin A and in the Degradation of Malvidin 3-O-Glucoside: An Approach in Wine-Like Model Systems.J Agric Food Chem. 2022 Oct 19;70(41):13049-13061. doi: 10.1021/acs.jafc.2c00615. Epub 2022 Apr 19. J Agric Food Chem. 2022. PMID: 35438989 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Research Materials
Miscellaneous
