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Diarylheptanoid Glucosides from Pyrostria major and Their Antiprotozoal Activities

Authors

  • Mehdi A. Beniddir,

    1. Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Labex LERMIT, 1, Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France, Fax: +33-1-69077247
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  • Philippe Grellier,

    1. Muséum National d'Histoire Naturelle, UMR 7245 CNRS, Team APE, CP 52, 61, Rue Buffon, 75231 Paris Cedex 05, France
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  • Philippe Rasoanaivo,

    1. Institut Malgache de Recherches Appliquées, B. P. 3833, 102 Antananarivo, Madagascar
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  • Philippe M. Loiseau,

    1. Groupe Chimiothérapie Antiparasitaire UMR 8076 CNRS, Labex LERMIT, Faculté de Pharmacie, Université Paris-Sud, Rue Jean-Baptiste-Clément, 92296 Châtenay Malabry Cedex, France
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  • Christian Bories,

    1. Groupe Chimiothérapie Antiparasitaire UMR 8076 CNRS, Labex LERMIT, Faculté de Pharmacie, Université Paris-Sud, Rue Jean-Baptiste-Clément, 92296 Châtenay Malabry Cedex, France
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  • Vincent Dumontet,

    1. Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Labex LERMIT, 1, Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France, Fax: +33-1-69077247
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  • Françoise Guéritte,

    1. Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Labex LERMIT, 1, Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France, Fax: +33-1-69077247
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  • Marc Litaudon

    1. Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Labex LERMIT, 1, Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France, Fax: +33-1-69077247
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Abstract

Eight new diarylheptanoid glucosides 18 have been isolated from the leaves of Pyrostria major (A. Rich & DC.) Cavaco [syn. Canthium major (A. Rich & DC.)] Cavaco. Their structures were determined by 1D and 2D NMR spectroscopic and HRMS analyses. The absolute configurations of the diarylheptanoids 14 were determined to be 3S and 5S by the application of the CD exciton chirality method to the corresponding 3,5-bis(p-bromobenzoyl) (13) and 3,5-bis(p-dimethylaminobenzoyl) (4) derivatives. Their antiparasitic activities against Plasmodium falciparum, Leishmania donovani (amastigote forms), and Trypanosoma brucei (trypomastigote bloodstream forms) as well as their cytotoxic activities against the HL-60, KB, and MRC5 cell lines of naturally occurring diarylheptanoid glucosides and their derivatives are reported.

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