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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.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Bicker J
Institute of Pharmaceutical Biology and Phytochemistry, University of Münster, Münster, Germany.
Petereit F
No affiliation info available
Hensel A
No affiliation info available

MeSH

Molecular StructurePhenolsPhloroglucinolPlant Components, AerialProanthocyanidinsRumex

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_ DB - PRIME DP - Unbound Medicine ER -