Abstract
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.
Highlights
Paullinia pinnata L. (Sapindaceae) is a woody climber growing in tropical regions worldwide.In West Africa and Tanzania, preparations from different parts of the plant have traditionally been used as remedies for the treatment of various diseases, such as dysenterie, nausea, bacterial and parasitic infections, wounds, infertility, cancer and neurological disorders [1,2,3,4,5]
Except for 3-β-dglucopyranosyloxy-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
Summary
Paullinia pinnata L. (Sapindaceae) is a woody climber growing in tropical regions worldwide.In West Africa and Tanzania, preparations from different parts of the plant have traditionally been used as remedies for the treatment of various diseases, such as dysenterie, nausea, bacterial and parasitic infections, wounds, infertility, cancer and neurological disorders [1,2,3,4,5]. Due to the large variety of traditional indications, the number of in vitro investigations is high: anticancer, antimicrobial [7], anthelmintic [5,8], antiprotozoal [5], molluscicidal [9], vasorelaxant [10], analgesic and anti-inflammatory [11,12] activities have been described. Regarding their phytochemical composition, extracts from leaves and roots of P. pinnata have been quite extensively investigated, the polarity of these extracts was mainly in the semi-polar to Molecules 2020, 25, 2287; doi:10.3390/molecules25102287 www.mdpi.com/journal/molecules. A cardiotonic tannin [18], ceramides and cerebrosides [19], several triterpenoids, l-quebrachitol, a trioxaphenanthrenone [17] and two unusual flavone glycosides [20]
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