Salix daphnoides: A Screening for Oligomeric and Polymeric Proanthocyanidins
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)-epi...
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| Format: | Article |
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MDPI AG
2015-07-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/20/8/13764 |
| _version_ | 1819230873571033088 |
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| author | Stefan Wiesneth Frank Petereit Guido Jürgenliemk |
| author_facet | Stefan Wiesneth Frank Petereit Guido Jürgenliemk |
| author_sort | Stefan Wiesneth |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-23T11:35:59Z |
| format | Article |
| id | doaj.art-3a167f88e31f48189e42c81ac82d06bd |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-23T11:35:59Z |
| publishDate | 2015-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-3a167f88e31f48189e42c81ac82d06bd2022-12-21T17:48:38ZengMDPI AGMolecules1420-30492015-07-01208137641377910.3390/molecules200813764molecules200813764Salix daphnoides: A Screening for Oligomeric and Polymeric ProanthocyanidinsStefan Wiesneth0Frank Petereit1Guido Jürgenliemk2Institute of Pharmaceutical Biology, Universitätsstr. 31, Regensburg D-93053, GermanyInstitute of Pharmaceutical Biology and Phytochemistry (IPBP), Corrensstr. 48, Münster D-48149, GermanyInstitute of Pharmaceutical Biology, Universitätsstr. 31, Regensburg D-93053, GermanyIn 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.http://www.mdpi.com/1420-3049/20/8/13764procyanidinsproanthocyanidinsflavan-3-olsSalix daphnoideswillow barklow temperature NMRthiolysispolarimetrypolymeric proanthocyanidins |
| spellingShingle | Stefan Wiesneth Frank Petereit Guido Jürgenliemk Salix daphnoides: A Screening for Oligomeric and Polymeric Proanthocyanidins Molecules procyanidins proanthocyanidins flavan-3-ols Salix daphnoides willow bark low temperature NMR thiolysis polarimetry polymeric proanthocyanidins |
| title | Salix daphnoides: A Screening for Oligomeric and Polymeric Proanthocyanidins |
| title_full | Salix daphnoides: A Screening for Oligomeric and Polymeric Proanthocyanidins |
| title_fullStr | Salix daphnoides: A Screening for Oligomeric and Polymeric Proanthocyanidins |
| title_full_unstemmed | Salix daphnoides: A Screening for Oligomeric and Polymeric Proanthocyanidins |
| title_short | Salix daphnoides: A Screening for Oligomeric and Polymeric Proanthocyanidins |
| title_sort | salix daphnoides a screening for oligomeric and polymeric proanthocyanidins |
| topic | procyanidins proanthocyanidins flavan-3-ols Salix daphnoides willow bark low temperature NMR thiolysis polarimetry polymeric proanthocyanidins |
| url | http://www.mdpi.com/1420-3049/20/8/13764 |
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