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Proanthocyanidins and a phloroglucinol derivative from Rumex acetosa L.
Fitoterapia. 2009 Dec; 80(8):483-95.F

Abstract

From the ethyl acetate soluble fraction of an acetone-water extract of the aerial parts of Rumex acetosa L. (Polygonaceae), a variety of monomeric flavan-3-ols (catechin, epicatechin, epicatechin-3-O-gallate), A- and B-type procyanidins and propelargonidins (15 dimers, 7 trimers, 2 tetramers) were isolated with 5 so far unknown natural products. Dimers: procyanidin B1, B2, B3, B4, B5, B7, A2, epiafzelechin-(4beta-->8)-epicatechin, epiafzelechin-(4beta-->8)-epicatechin-3-O-gallate (new natural product), epiafzelechin-(4beta-->6)-epicatechin-3-O-gallate (new natural product), epiafzelechin-3-O-gallate-(4beta-->8)-epicatechin-3-O-gallate, B2-3'-O-gallate, B2-3,3'-di-O-gallate, B5-3'-O-gallate, and B5-3,3'-di-O-gallate. Trimers: procyanidin C1, epiafzelechin-(4beta-->8)-epicatechin-(4beta-->8)-epicatechin (new natural product), epicatechin-(4beta-->8)-epicatechin-(4beta-->8)-catechin, cinnamtannin B1, cinnamtannin B1-3-O-gallate (new natural product), tentatively epicatechin-(2beta-->7, 4beta-->8)-epiafzelechin-(4alpha-->8)-epicatechin (new natural product), and epicatechin-3-O-gallate-(4beta-->8)-epicatechin-3-O-gallate-(4beta-->8)-epicatechin-3-O-gallate. Tetramers: procyanidin D1 and parameritannin A1. All compounds were elucidated by ESI-MS, CD spectra, 1D- and 2D-NMR experiments as free phenols or peracetylated derivatives and, in part, after partial acid-catalysed degradation with phloroglucinol. A more abundant proanthocyanidin polymer was also isolated, purified and its chemical composition studied by (13)C NMR. In addition a so far unknown phloroglucinolglycoside (1-O-beta-D-(2,4-dihydroxy-6-methoxyphenyl)-6-O-(4-hydroxy-3,5-dimethoxybenzoyl)-glucopyranoside) was isolated.

Authors+Show Affiliations

Institute of Pharmaceutical Biology and Phytochemistry, University of Münster, Münster, Germany.No affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

19695312

Citation

Bicker, J, et al. "Proanthocyanidins and a Phloroglucinol Derivative From Rumex Acetosa L." Fitoterapia, vol. 80, no. 8, 2009, pp. 483-95.
Bicker J, Petereit F, Hensel A. Proanthocyanidins and a phloroglucinol derivative from Rumex acetosa L. Fitoterapia. 2009;80(8):483-95.
Bicker, J., Petereit, F., & Hensel, A. (2009). Proanthocyanidins and a phloroglucinol derivative from Rumex acetosa L. Fitoterapia, 80(8), 483-95. https://doi.org/10.1016/j.fitote.2009.08.015
Bicker J, Petereit F, Hensel A. Proanthocyanidins and a Phloroglucinol Derivative From Rumex Acetosa L. Fitoterapia. 2009;80(8):483-95. PubMed PMID: 19695312.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Proanthocyanidins and a phloroglucinol derivative from Rumex acetosa L. AU - Bicker,J, AU - Petereit,F, AU - Hensel,A, Y1 - 2009/08/18/ PY - 2009/07/09/received PY - 2009/08/09/accepted PY - 2009/8/22/entrez PY - 2009/8/22/pubmed PY - 2010/2/2/medline SP - 483 EP - 95 JF - Fitoterapia JO - Fitoterapia VL - 80 IS - 8 N2 - From the ethyl acetate soluble fraction of an acetone-water extract of the aerial parts of Rumex acetosa L. (Polygonaceae), a variety of monomeric flavan-3-ols (catechin, epicatechin, epicatechin-3-O-gallate), A- and B-type procyanidins and propelargonidins (15 dimers, 7 trimers, 2 tetramers) were isolated with 5 so far unknown natural products. Dimers: procyanidin B1, B2, B3, B4, B5, B7, A2, epiafzelechin-(4beta-->8)-epicatechin, epiafzelechin-(4beta-->8)-epicatechin-3-O-gallate (new natural product), epiafzelechin-(4beta-->6)-epicatechin-3-O-gallate (new natural product), epiafzelechin-3-O-gallate-(4beta-->8)-epicatechin-3-O-gallate, B2-3'-O-gallate, B2-3,3'-di-O-gallate, B5-3'-O-gallate, and B5-3,3'-di-O-gallate. Trimers: procyanidin C1, epiafzelechin-(4beta-->8)-epicatechin-(4beta-->8)-epicatechin (new natural product), epicatechin-(4beta-->8)-epicatechin-(4beta-->8)-catechin, cinnamtannin B1, cinnamtannin B1-3-O-gallate (new natural product), tentatively epicatechin-(2beta-->7, 4beta-->8)-epiafzelechin-(4alpha-->8)-epicatechin (new natural product), and epicatechin-3-O-gallate-(4beta-->8)-epicatechin-3-O-gallate-(4beta-->8)-epicatechin-3-O-gallate. Tetramers: procyanidin D1 and parameritannin A1. All compounds were elucidated by ESI-MS, CD spectra, 1D- and 2D-NMR experiments as free phenols or peracetylated derivatives and, in part, after partial acid-catalysed degradation with phloroglucinol. A more abundant proanthocyanidin polymer was also isolated, purified and its chemical composition studied by (13)C NMR. In addition a so far unknown phloroglucinolglycoside (1-O-beta-D-(2,4-dihydroxy-6-methoxyphenyl)-6-O-(4-hydroxy-3,5-dimethoxybenzoyl)-glucopyranoside) was isolated. SN - 1873-6971 UR - https://www.unboundmedicine.com/medline/citation/19695312/Proanthocyanidins_and_a_phloroglucinol_derivative_from_Rumex_acetosa_L_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0367-326X(09)00191-9 DB - PRIME DP - Unbound Medicine ER -