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New approach for the synthesis and isolation of dimeric procyanidins.
J Agric Food Chem. 2008 Jul 09; 56(13):5374-85.JA

Abstract

A semisynthetic approach for the strategic formation of various procyanidins has been developed. Procyanidin-rich grape seed extracts were reacted with flavan-3-ols under acid catalysis. The reaction enables the formation of dimeric procyanidins and the elimination of higher oligomeric and polymeric procyanidins through degradation. An easy and fast method for the isolation of large amounts of procyanidins after semisynthetic formation by high-speed countercurrent chromatography is presented. Dimeric procyanidins (B1, B2, B3, B4, B5, and B7) were obtained and isolated. Furthermore, galloylated dimeric procyanidins [(-)-epicatechin-3- O-gallate-4beta-->8-(+)-catechin, (-)-epicatechin-3- O-gallate-4beta-->8-(-)-epicatechin, (-)-epicatechin-3- O-gallate-4beta-->6-(-)-epicatechin, and (-)-epicatechin-4beta-->8-(-)-epicatechin-3- O-gallate], as well as trimeric procyanidins [C1, (-)-epicatechin-4beta-->6-(-)-epicatechin-4beta-->8-(-)-epicatechin, and (-)-epicatechin-4beta-->6-(-)-epicatechin-4beta-->6-(+)-catechin] were obtained and isolated as side products. This approach also afforded gambiriins A1 and A2, which were all isolated and unambiguously identified, and the novel 3-(2,4,6-trihydroxyphenyl)-1-(3,4-dihydroxyphenyl)-propan-2-ol-1beta-->8-(-)-epicatechin (gambiriin A4).

Authors+Show Affiliations

Institute of Food Chemistry, University of Braunschweig-Institute of Technology, Schleinitzstrasse 20, 38106 Braunschweig, Germany.No affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

18540617

Citation

Köhler, Nils, et al. "New Approach for the Synthesis and Isolation of Dimeric Procyanidins." Journal of Agricultural and Food Chemistry, vol. 56, no. 13, 2008, pp. 5374-85.
Köhler N, Wray V, Winterhalter P. New approach for the synthesis and isolation of dimeric procyanidins. J Agric Food Chem. 2008;56(13):5374-85.
Köhler, N., Wray, V., & Winterhalter, P. (2008). New approach for the synthesis and isolation of dimeric procyanidins. Journal of Agricultural and Food Chemistry, 56(13), 5374-85. https://doi.org/10.1021/jf7036505
Köhler N, Wray V, Winterhalter P. New Approach for the Synthesis and Isolation of Dimeric Procyanidins. J Agric Food Chem. 2008 Jul 9;56(13):5374-85. PubMed PMID: 18540617.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - New approach for the synthesis and isolation of dimeric procyanidins. AU - Köhler,Nils, AU - Wray,Victor, AU - Winterhalter,Peter, Y1 - 2008/06/10/ PY - 2008/6/11/pubmed PY - 2008/9/3/medline PY - 2008/6/11/entrez SP - 5374 EP - 85 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 56 IS - 13 N2 - A semisynthetic approach for the strategic formation of various procyanidins has been developed. Procyanidin-rich grape seed extracts were reacted with flavan-3-ols under acid catalysis. The reaction enables the formation of dimeric procyanidins and the elimination of higher oligomeric and polymeric procyanidins through degradation. An easy and fast method for the isolation of large amounts of procyanidins after semisynthetic formation by high-speed countercurrent chromatography is presented. Dimeric procyanidins (B1, B2, B3, B4, B5, and B7) were obtained and isolated. Furthermore, galloylated dimeric procyanidins [(-)-epicatechin-3- O-gallate-4beta-->8-(+)-catechin, (-)-epicatechin-3- O-gallate-4beta-->8-(-)-epicatechin, (-)-epicatechin-3- O-gallate-4beta-->6-(-)-epicatechin, and (-)-epicatechin-4beta-->8-(-)-epicatechin-3- O-gallate], as well as trimeric procyanidins [C1, (-)-epicatechin-4beta-->6-(-)-epicatechin-4beta-->8-(-)-epicatechin, and (-)-epicatechin-4beta-->6-(-)-epicatechin-4beta-->6-(+)-catechin] were obtained and isolated as side products. This approach also afforded gambiriins A1 and A2, which were all isolated and unambiguously identified, and the novel 3-(2,4,6-trihydroxyphenyl)-1-(3,4-dihydroxyphenyl)-propan-2-ol-1beta-->8-(-)-epicatechin (gambiriin A4). SN - 1520-5118 UR - https://www.unboundmedicine.com/medline/citation/18540617/New_approach_for_the_synthesis_and_isolation_of_dimeric_procyanidins_ L2 - https://doi.org/10.1021/jf7036505 DB - PRIME DP - Unbound Medicine ER -