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Molecules 2015, 20(8), 14810-14832; doi:10.3390/molecules200814810

Bioassay-Guided Fractionation of a Leaf Extract from Combretum mucronatum with Anthelmintic Activity: Oligomeric Procyanidins as the Active Principle

1
Institute for Pharmaceutical Biology and Phytochemistry, University of Münster, Schlossplatz 2, D-48149 Münster, Germany
2
Institute for Zoophysiology, University of Münster, Schlossplatz 8, D-48143 Münster, Germany
*
Author to whom correspondence should be addressed.
Academic Editor: Thomas J. Schmidt
Received: 7 July 2015 / Revised: 5 August 2015 / Accepted: 11 August 2015 / Published: 14 August 2015
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Abstract

Combretum mucronatum Schumach. & Thonn. is a medicinal plant widely used in West African traditional medicine for wound healing and the treatment of helminth infections. The present study aimed at a phytochemical characterization of a hydroalcoholic leaf extract of this plant and the identification of the anthelmintic compounds by bioassay-guided fractionation. An EtOH-H2O (1:1) extract from defatted leaves was partitioned between EtOAc and H2O. Further fractionation was performed by fast centrifugal partition chromatography, RP18-MPLC and HPLC. Epicatechin (1), oligomeric proanthocyanidins (OPC) 2 to 10 (mainly procyanidins) and flavonoids 11 to 13 were identified as main components of the extract. The hydroalcoholic extract, fractions and purified compounds were tested in vitro for their anthelmintic activity using the model nematode Caenorhabditis elegans. The bioassay-guided fractionation led to the identification of OPCs as the active compounds with a dose-dependent anthelmintic activity ranging from 1 to 1000 μM. Using OPC-clusters with a defined degree of polymerization (DP) revealed that a DP ≥ 3 is necessary for an anthelmintic activity, whereas a DP > 4 does not lead to a further increased inhibitory effect against the helminths. In summary, the findings rationalize the traditional use of C. mucronatum and provide further insight into the anthelmintic activity of condensed tannins. View Full-Text
Keywords: Combretum mucronatum; anthelmintic; Caenorhabditis elegans; flavonoids; proanthocyanidins; structure-activity; tannins Combretum mucronatum; anthelmintic; Caenorhabditis elegans; flavonoids; proanthocyanidins; structure-activity; tannins
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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

Spiegler, V.; Sendker, J.; Petereit, F.; Liebau, E.; Hensel, A. Bioassay-Guided Fractionation of a Leaf Extract from Combretum mucronatum with Anthelmintic Activity: Oligomeric Procyanidins as the Active Principle. Molecules 2015, 20, 14810-14832.

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