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Molecules 2015, 20(8), 13764-13779; doi:10.3390/molecules200813764

Salix daphnoides: A Screening for Oligomeric and Polymeric Proanthocyanidins

1
Institute of Pharmaceutical Biology, Universitätsstr. 31, Regensburg D-93053, Germany
2
Institute of Pharmaceutical Biology and Phytochemistry (IPBP), Corrensstr. 48, Münster D-48149, Germany
*
Author to whom correspondence should be addressed.
Academic Editor: Thomas J. Schmidt
Received: 28 June 2015 / Revised: 8 July 2015 / Accepted: 16 July 2015 / Published: 29 July 2015
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Abstract

In the present study, a qualitative analysis of proanthocyanidins (PAs) from an aqueous-methanolic extract of Salix daphnoides VILL. bark is described. Procyanidin B1 (1), B2 (2), B3 (3), B4 (4), C1 (5), epicatechin-(4β→8)-epicatechin-(4β→8)-catechin (6) and epicatechin-(4β→8)-epicatechin-(4β→8)-epicatechin-(4β→8)-catechin (7) have been isolated by a combination of different chromatographic separations on Sephadex® LH-20-, MCI®-, Diol-and RP-18-phases. Mass spectrometry, 1D- and 2D-NMR, circular dichroism and polarimetry were used for their structure elucidation and verification by comparison with the literature. Additionally, two fractions of very polar flavan-3-ols were compared: “regular” polymeric PAs received at the very end of the Sephadex® LH-20 chromatography showing no mobility on silica TLC and “unusual” PAs with the same RF-value but already eluting together with flavonoids in the Sephadex® LH-20 system. These “unusual” PAs were subsequently enriched by centrifugal partition chromatography (CPC). 13C-NMR, polarimetry, thiolysis, acid hydrolysis and phloroglucinol degradation were used to characterize both fractions. Differences in the composition of different flavan-3-ol units and the middle chain length were observed. View Full-Text
Keywords: procyanidins; proanthocyanidins; flavan-3-ols; Salix daphnoides; willow bark; low temperature NMR; thiolysis; polarimetry; polymeric proanthocyanidins procyanidins; proanthocyanidins; flavan-3-ols; Salix daphnoides; willow bark; low temperature NMR; thiolysis; polarimetry; polymeric proanthocyanidins
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Wiesneth, S.; Petereit, F.; Jürgenliemk, G. Salix daphnoides: A Screening for Oligomeric and Polymeric Proanthocyanidins. Molecules 2015, 20, 13764-13779.

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