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Separation of proanthocyanidins isolated from tea leaves using high-speed counter-current chromatography.
J Chromatogr A. 2009 May 08; 1216(19):4295-302.JC

Abstract

The proanthocyanidin extract from tea (Camellia sinensis) leaves was purified for the further study of the biological role of proanthocyanidins in blister blight leaf disease of tea, which is caused by the fungus Exobasidium vexans. An aqueous acetone extract of proanthocyanidins prepared from healthy tea leaves was partially purified using Sephadex LH-20 chromatography. The crude proanthocyanidin extract obtained was fractionated with high-speed counter-current chromatography (HSCCC) using the solvent system n-hexane-EtOAc-MeOH-water (1:5:1:5). The purity of the each isolated fraction after a single HSCCC run was evaluated by high-performance liquid chromatography (HPLC). Seven fractions of high purity were isolated. The identity of the compound present in each fraction isolated was established using electrospray ionization mass spectrometry (ESI-MS) and nuclear magnetic resonance (NMR) spectroscopy. Five proanthocyanidins and two flavanol digallates, (-)-epigallocatechin digallate (EGCDG) and (-)-epicatechin digallate (ECDG) were isolated. Comparison of spectral data of the proanthocyanidins isolated with those previously reported indicated that all five were known B-type proanthocyanidins with 2,3-cis stereochemistry in both the upper (u-unit) and the terminal (t-unit) units, and 4R configuration of the C-ring in the u-unit. The proanthocyanidins were established to be dimers composed of (-)-epigallocatechin gallate (EGCG), (-)-epicatechin gallate (ECG) and (-)-epiafzelechin gallate (EAG) units with the following structures: EGCG-(4beta-->6)-EGCG, ECG-(4beta-->6)-EGCG, EGCG-(4beta-->6)-ECG, EAG-(4beta-->6)-EGCG, ECG-(4beta-->6)-ECG by analysis of spectral data. Therefore HSCCC offers a powerful method for the separation of a group of closely related naturally occurring compounds.

Authors+Show Affiliations

Department of Chemistry, University of Peradeniya, Sri Lanka. nskumar@pdn.ac.lkNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

19136115

Citation

Savitri Kumar, N, et al. "Separation of Proanthocyanidins Isolated From Tea Leaves Using High-speed Counter-current Chromatography." Journal of Chromatography. A, vol. 1216, no. 19, 2009, pp. 4295-302.
Savitri Kumar N, Maduwantha B Wijekoon WM, Kumar V, et al. Separation of proanthocyanidins isolated from tea leaves using high-speed counter-current chromatography. J Chromatogr A. 2009;1216(19):4295-302.
Savitri Kumar, N., Maduwantha B Wijekoon, W. M., Kumar, V., Nimal Punyasiri, P. A., & Sarath B Abeysinghe, I. (2009). Separation of proanthocyanidins isolated from tea leaves using high-speed counter-current chromatography. Journal of Chromatography. A, 1216(19), 4295-302. https://doi.org/10.1016/j.chroma.2008.12.025
Savitri Kumar N, et al. Separation of Proanthocyanidins Isolated From Tea Leaves Using High-speed Counter-current Chromatography. J Chromatogr A. 2009 May 8;1216(19):4295-302. PubMed PMID: 19136115.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Separation of proanthocyanidins isolated from tea leaves using high-speed counter-current chromatography. AU - Savitri Kumar,N, AU - Maduwantha B Wijekoon,W M A, AU - Kumar,Vijaya, AU - Nimal Punyasiri,P A, AU - Sarath B Abeysinghe,I, Y1 - 2008/12/24/ PY - 2008/09/24/received PY - 2008/11/26/revised PY - 2008/12/04/accepted PY - 2009/1/13/entrez PY - 2009/1/13/pubmed PY - 2009/7/16/medline SP - 4295 EP - 302 JF - Journal of chromatography. A JO - J Chromatogr A VL - 1216 IS - 19 N2 - The proanthocyanidin extract from tea (Camellia sinensis) leaves was purified for the further study of the biological role of proanthocyanidins in blister blight leaf disease of tea, which is caused by the fungus Exobasidium vexans. An aqueous acetone extract of proanthocyanidins prepared from healthy tea leaves was partially purified using Sephadex LH-20 chromatography. The crude proanthocyanidin extract obtained was fractionated with high-speed counter-current chromatography (HSCCC) using the solvent system n-hexane-EtOAc-MeOH-water (1:5:1:5). The purity of the each isolated fraction after a single HSCCC run was evaluated by high-performance liquid chromatography (HPLC). Seven fractions of high purity were isolated. The identity of the compound present in each fraction isolated was established using electrospray ionization mass spectrometry (ESI-MS) and nuclear magnetic resonance (NMR) spectroscopy. Five proanthocyanidins and two flavanol digallates, (-)-epigallocatechin digallate (EGCDG) and (-)-epicatechin digallate (ECDG) were isolated. Comparison of spectral data of the proanthocyanidins isolated with those previously reported indicated that all five were known B-type proanthocyanidins with 2,3-cis stereochemistry in both the upper (u-unit) and the terminal (t-unit) units, and 4R configuration of the C-ring in the u-unit. The proanthocyanidins were established to be dimers composed of (-)-epigallocatechin gallate (EGCG), (-)-epicatechin gallate (ECG) and (-)-epiafzelechin gallate (EAG) units with the following structures: EGCG-(4beta-->6)-EGCG, ECG-(4beta-->6)-EGCG, EGCG-(4beta-->6)-ECG, EAG-(4beta-->6)-EGCG, ECG-(4beta-->6)-ECG by analysis of spectral data. Therefore HSCCC offers a powerful method for the separation of a group of closely related naturally occurring compounds. SN - 1873-3778 UR - https://www.unboundmedicine.com/medline/citation/19136115/Separation_of_proanthocyanidins_isolated_from_tea_leaves_using_high_speed_counter_current_chromatography_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0021-9673(08)02146-8 DB - PRIME DP - Unbound Medicine ER -