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Monomeric, oligomeric, and polymeric flavan-3-ol composition of wines and grapes from Vitis vinifera L. Cv. Graciano, Tempranillo, and Cabernet Sauvignon.
J Agric Food Chem. 2003 Oct 22; 51(22):6475-81.JA

Abstract

The monomeric, oligomeric, and polymeric flavan-3-ol composition of wines, grape seeds, and skins from Vitis vinifera L. cv. Graciano, Tempranillo, and Cabernet Sauvignon has been studied using (1) fractionation by polyamide column chromatography followed by HPLC/ESI-MS analysis, (2) fractionation on C(18) Sep-Pak cartridges followed by reaction with vanillin and acid-catalyzed degradation in the presence of toluene-alpha-thiol (thiolysis). The content of monomers ((+)-catechin and (-)-epicatechin), procyanidin dimers (B3, B1, B4, and B2), trimers (T2 and C1), and dimer gallates (B2-3-O-gallate, B2-3'-O-gallate, and B1-3-O-gallate) ranged from 76.93 to 133.18 mg/L in wines, from 2.30 to 8.21 mg/g in grape seeds, and from 0.14 to 0.38 mg/g in grape skins. In wines, the polymeric fraction represented 77-84% of total flavan-3-ols and showed a mean degree of polymerization (mDP) value of 6.3-13.0. In grapes, the polymeric fraction represented 75-81% of total flavan-3-ols in seeds and 94-98% in skins and showed mDP values of 6.4-7.3 in seeds and 33.8-85.7 in skins. All the monomeric flavan-3-ols and oligomeric procyanidins found in wines were also present in seeds, although differences in their relative abundances were seen. The skin polymeric proanthocyanidins participated in the equilibration of the wine polymeric proanthocyanidin fraction, especially contributing to the polymer subunit composition and mDP.

Authors+Show Affiliations

Monagas M
Instituto de Fermentaciones Industriales, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain.
Gómez-Cordovés C
No affiliation info available
Bartolomé B
No affiliation info available
Laureano O
No affiliation info available
Ricardo da Silva JM
No affiliation info available

MeSH

BiflavonoidsCatechinChromatography, High Pressure LiquidFlavonoidsFruitHydrogen-Ion ConcentrationPolymersProanthocyanidinsSeedsSpectrometry, Mass, Electrospray IonizationTolueneVitisWine

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

14558765

Citation

Monagas, María, et al. "Monomeric, Oligomeric, and Polymeric Flavan-3-ol Composition of Wines and Grapes From Vitis Vinifera L. Cv. Graciano, Tempranillo, and Cabernet Sauvignon." Journal of Agricultural and Food Chemistry, vol. 51, no. 22, 2003, pp. 6475-81.
Monagas M, Gómez-Cordovés C, Bartolomé B, et al. Monomeric, oligomeric, and polymeric flavan-3-ol composition of wines and grapes from Vitis vinifera L. Cv. Graciano, Tempranillo, and Cabernet Sauvignon. J Agric Food Chem. 2003;51(22):6475-81.
Monagas, M., Gómez-Cordovés, C., Bartolomé, B., Laureano, O., & Ricardo da Silva, J. M. (2003). Monomeric, oligomeric, and polymeric flavan-3-ol composition of wines and grapes from Vitis vinifera L. Cv. Graciano, Tempranillo, and Cabernet Sauvignon. Journal of Agricultural and Food Chemistry, 51(22), 6475-81.
Monagas M, et al. Monomeric, Oligomeric, and Polymeric Flavan-3-ol Composition of Wines and Grapes From Vitis Vinifera L. Cv. Graciano, Tempranillo, and Cabernet Sauvignon. J Agric Food Chem. 2003 Oct 22;51(22):6475-81. PubMed PMID: 14558765.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Monomeric, oligomeric, and polymeric flavan-3-ol composition of wines and grapes from Vitis vinifera L. Cv. Graciano, Tempranillo, and Cabernet Sauvignon. AU - Monagas,María, AU - Gómez-Cordovés,Carmen, AU - Bartolomé,Begoña, AU - Laureano,Olga, AU - Ricardo da Silva,Jorge M, PY - 2003/10/16/pubmed PY - 2003/12/12/medline PY - 2003/10/16/entrez SP - 6475 EP - 81 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 51 IS - 22 N2 - The monomeric, oligomeric, and polymeric flavan-3-ol composition of wines, grape seeds, and skins from Vitis vinifera L. cv. Graciano, Tempranillo, and Cabernet Sauvignon has been studied using (1) fractionation by polyamide column chromatography followed by HPLC/ESI-MS analysis, (2) fractionation on C(18) Sep-Pak cartridges followed by reaction with vanillin and acid-catalyzed degradation in the presence of toluene-alpha-thiol (thiolysis). The content of monomers ((+)-catechin and (-)-epicatechin), procyanidin dimers (B3, B1, B4, and B2), trimers (T2 and C1), and dimer gallates (B2-3-O-gallate, B2-3'-O-gallate, and B1-3-O-gallate) ranged from 76.93 to 133.18 mg/L in wines, from 2.30 to 8.21 mg/g in grape seeds, and from 0.14 to 0.38 mg/g in grape skins. In wines, the polymeric fraction represented 77-84% of total flavan-3-ols and showed a mean degree of polymerization (mDP) value of 6.3-13.0. In grapes, the polymeric fraction represented 75-81% of total flavan-3-ols in seeds and 94-98% in skins and showed mDP values of 6.4-7.3 in seeds and 33.8-85.7 in skins. All the monomeric flavan-3-ols and oligomeric procyanidins found in wines were also present in seeds, although differences in their relative abundances were seen. The skin polymeric proanthocyanidins participated in the equilibration of the wine polymeric proanthocyanidin fraction, especially contributing to the polymer subunit composition and mDP. SN - 0021-8561 UR - https://www.unboundmedicine.com/medline/citation/14558765/Monomeric_oligomeric_and_polymeric_flavan_3_ol_composition_of_wines_and_grapes_from_Vitis_vinifera_L__Cv__Graciano_Tempranillo_and_Cabernet_Sauvignon_ DB - PRIME DP - Unbound Medicine ER -