TY  - JOUR
AB  - Extracts from the roots of Paullinia pinnata L. are used in West Africa as traditional remedies for a variety of diseases including infestations with soil-transmitted helminths. Based on the results of an ethnopharmacological survey in Ghana, an aqueous acetone (70%) extract was investigated for its anthelmintic and phytochemical properties. Partitioning of the crude extract followed by several fractionation steps of the ethyl acetate phase using Sephadex® LH-20, fast centrifugal partition chromatography, RP-18-MPLC and HPLC led to isolation of six oligomeric A-type procyanidins (1 to 6). To determine the anthelmintic activity, the crude extract, fractions and isolated compounds were tested in vitro against the model organism Caenorhabditis elegans. A significantly better activity was observed for the trimeric A-type procyanidin (1) compared to a B-type trimer. However, this effect could not be generalized for the tetrameric procyanidins, for which the type of the interflavan-linkage (4→6 vs. 4→8) had the greatest impact on the bioactivity. Besides the procyanidins, three novel compounds, isofraxidin-7-O-α-l-rhamnopyranosyl-(1″→6′)-β-d-glucopyranoside (17), 4-methoxycatechol-2-O-(5′′-O-vanilloyl-β-apiofuranosyl)-(1′′→2′)-β-glucopyranoside (18) and a 6-(3-methoxy-4-hydroxyphenyl)-hexane-2,4-diol-2-O-hexoside (19) were isolated together with further ten known compounds (7 to 16), mainly coumarins and coumarinolignans. Except for 3-β-d-glucopyranosyloxy-4-methyl-2(5H)-furanone (15), none of the isolated compounds has previously been described for P. pinnata. The anthelmintic activity was attributed to the presence of procyanidins, but not to any of the other compound classes. In summary, the findings rationalize the traditional use of P. pinnata root extracts as anthelmintic remedies.
AU  - Spiegler, Verena
DA  - 2020-05-13
KW  - anthelmintic
KW  - Paullinia pinnata
KW  - coumarin
KW  - cleomiscosin
KW  - procyanidin
KW  - phenolic
KW  - furanone
KW  - phenylhexanoid
KW  - Caenorhabditis elegans
LA  - eng
N1  - Molecules 25 (2020) 10, 2287, 1-23
N1  - Finanziert durch den Open-Access-Publikationsfonds der Westfälischen Wilhelms-Universität Münster (WWU Münster)
N1  - Förderer: Deutsche Forschungsgemeinschaft / Projektnummer: 423277515
N1  - Funding organisation: Deutsche Forschungsgemeinschaft / Project number: 423277515
PY  - 2020-05-13
TI  - Anthelmintic A-Type Procyanidins and Further Characterization of the Phenolic Composition of a Root Extract from Paullinia pinnata
UR  - https://nbn-resolving.org/urn:nbn:de:hbz:6-74079442974
Y2  - 2024-12-27T06:38:11
ER  -