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Preparative isolation of procyanidins from grape seed extracts by high-speed counter-current chromatography.
J Chromatogr A. 2008 Jan 04; 1177(1):114-25.JC

Abstract

High-speed counter-current chromatography (HSCCC) has been applied to the separation of grape seed procyanidins. The isolation of dimeric to tetrameric procyanidins is achieved after removing the polymeric compounds by solvent precipitation. An additional clean-up by solid-phase extraction on polyamide improved the purities of the isolated compounds. The solvent systems ethyl acetate/2-propanol/water (40:1:40, v/v/v), ethyl acetate/2-propanol/water (20:1:20, v/v/v), and ethyl acetate/1-butanol/water (14:1:15, v/v/v) were successfully used for the fractionation. The combination of HPLC-MS, diode array detection, and NMR analysis, as well as phloroglucinolysis, confirmed the structures of the isolated compounds: B1 [EC-(4beta-->8)-C], B2 [EC-(4beta-->8)-EC], B3 [C-(4alpha-->8)-C], B4 [C-(4alpha-->8)-EC], B5 [EC-4beta-->6-EC], B7 [EC-(4beta-->8)-C], [ECG-(4beta-->8)-C], trimeric procyanidin C1 [EC-4beta-->8-EC-4beta-->8-EC], and the tetrameric procyanidin cinnamtannin A2 (where C: catechin, EC: epicatechin and ECG: epicatechin-3-O-gallate).

Authors+Show Affiliations

Institute of Food Chemistry, TU-Braunschweig, Schleinitzstrasse 20, DE-38106 Braunschweig, Germany. n.koehler@tu-bs.deNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

18054944

Citation

Köhler, N, et al. "Preparative Isolation of Procyanidins From Grape Seed Extracts By High-speed Counter-current Chromatography." Journal of Chromatography. A, vol. 1177, no. 1, 2008, pp. 114-25.
Köhler N, Wray V, Winterhalter P. Preparative isolation of procyanidins from grape seed extracts by high-speed counter-current chromatography. J Chromatogr A. 2008;1177(1):114-25.
Köhler, N., Wray, V., & Winterhalter, P. (2008). Preparative isolation of procyanidins from grape seed extracts by high-speed counter-current chromatography. Journal of Chromatography. A, 1177(1), 114-25.
Köhler N, Wray V, Winterhalter P. Preparative Isolation of Procyanidins From Grape Seed Extracts By High-speed Counter-current Chromatography. J Chromatogr A. 2008 Jan 4;1177(1):114-25. PubMed PMID: 18054944.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Preparative isolation of procyanidins from grape seed extracts by high-speed counter-current chromatography. AU - Köhler,N, AU - Wray,V, AU - Winterhalter,P, Y1 - 2007/11/17/ PY - 2007/07/13/received PY - 2007/11/07/revised PY - 2007/11/09/accepted PY - 2007/12/7/pubmed PY - 2008/5/6/medline PY - 2007/12/7/entrez SP - 114 EP - 25 JF - Journal of chromatography. A JO - J Chromatogr A VL - 1177 IS - 1 N2 - High-speed counter-current chromatography (HSCCC) has been applied to the separation of grape seed procyanidins. The isolation of dimeric to tetrameric procyanidins is achieved after removing the polymeric compounds by solvent precipitation. An additional clean-up by solid-phase extraction on polyamide improved the purities of the isolated compounds. The solvent systems ethyl acetate/2-propanol/water (40:1:40, v/v/v), ethyl acetate/2-propanol/water (20:1:20, v/v/v), and ethyl acetate/1-butanol/water (14:1:15, v/v/v) were successfully used for the fractionation. The combination of HPLC-MS, diode array detection, and NMR analysis, as well as phloroglucinolysis, confirmed the structures of the isolated compounds: B1 [EC-(4beta-->8)-C], B2 [EC-(4beta-->8)-EC], B3 [C-(4alpha-->8)-C], B4 [C-(4alpha-->8)-EC], B5 [EC-4beta-->6-EC], B7 [EC-(4beta-->8)-C], [ECG-(4beta-->8)-C], trimeric procyanidin C1 [EC-4beta-->8-EC-4beta-->8-EC], and the tetrameric procyanidin cinnamtannin A2 (where C: catechin, EC: epicatechin and ECG: epicatechin-3-O-gallate). SN - 0021-9673 UR - https://www.unboundmedicine.com/medline/citation/18054944/Preparative_isolation_of_procyanidins_from_grape_seed_extracts_by_high_speed_counter_current_chromatography_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0021-9673(07)01963-2 DB - PRIME DP - Unbound Medicine ER -