Diarylheptanoid Glucosides from Pyrostria major and Their Antiprotozoal Activities
Identifieur interne : 001555 ( Istex/Curation ); précédent : 001554; suivant : 001556Diarylheptanoid Glucosides from Pyrostria major and Their Antiprotozoal Activities
Auteurs : Mehdi A. Beniddir ; Philippe Grellier [France] ; Philippe Rasoanaivo [Madagascar] ; Philippe M. Loiseau [France] ; Christian Bories [France] ; Vincent Dumontet ; Françoise Guéritte ; Marc Litaudon [France]Source :
- European Journal of Organic Chemistry [ 1434-193X ] ; 2012-02.
Abstract
Eight new diarylheptanoid glucosides 1–8 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 1–4 were determined to be 3S and 5S by the application of the CD exciton chirality method to the corresponding 3,5‐bis(p‐bromobenzoyl) (1–3) 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.
A story of serendipity: biologically inactive natural diarylheptanoid glucosides have been isolated from Pyrostria major. Their absolute configurations were determined to be 3S and 5S by the application of the CD exciton chirality method to the corresponding benzoyl derivatives. The study led to the discovery of new compounds possessing selective antiprotozoal activity.
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DOI: 10.1002/ejoc.201101414
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Mehdi A. Beniddir<affiliation><mods:affiliation>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</mods:affiliation><wicri:noCountry code="subField">+33‐1‐69077247</wicri:noCountry></affiliation><affiliation><mods:affiliation>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</mods:affiliation><wicri:noCountry code="subField">+33‐1‐69077247</wicri:noCountry></affiliation><affiliation><mods:affiliation>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</mods:affiliation><wicri:noCountry code="subField">+33‐1‐69077247</wicri:noCountry></affiliation>Le document en format XML
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Beniddir</name><affiliation><mods:affiliation>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</mods:affiliation><wicri:noCountry code="subField">+33‐1‐69077247</wicri:noCountry></affiliation></author><author><name sortKey="Grellier, Philippe" sort="Grellier, Philippe" uniqKey="Grellier P" first="Philippe" last="Grellier">Philippe Grellier</name><affiliation wicri:level="1"><mods:affiliation>Muséum National d'Histoire Naturelle, UMR 7245 CNRS, Team APE, CP 52, 61, Rue Buffon, 75231 Paris Cedex 05, France</mods:affiliation><country xml:lang="fr">France</country><wicri:regionArea>Muséum National d'Histoire Naturelle, UMR 7245 CNRS, Team APE, CP 52, 61, Rue Buffon, 75231 Paris Cedex 05</wicri:regionArea></affiliation></author><author><name sortKey="Rasoanaivo, Philippe" sort="Rasoanaivo, Philippe" uniqKey="Rasoanaivo P" first="Philippe" last="Rasoanaivo">Philippe Rasoanaivo</name><affiliation wicri:level="1"><mods:affiliation>Institut Malgache de Recherches Appliquées, B. P. 3833, 102 Antananarivo, Madagascar</mods:affiliation><country xml:lang="fr">Madagascar</country><wicri:regionArea>Institut Malgache de Recherches Appliquées, B. P. 3833, 102 Antananarivo</wicri:regionArea></affiliation></author><author><name sortKey="Loiseau, Philippe M" sort="Loiseau, Philippe M" uniqKey="Loiseau P" first="Philippe M." last="Loiseau">Philippe M. Loiseau</name><affiliation wicri:level="1"><mods:affiliation>Groupe Chimiothérapie Antiparasitaire UMR 8076 CNRS, Labex LERMIT, Faculté de Pharmacie, Université Paris‐Sud, Rue Jean‐Baptiste‐Clément, 92296 Châtenay Malabry Cedex, France</mods:affiliation><country xml:lang="fr">France</country><wicri:regionArea>Groupe Chimiothérapie Antiparasitaire UMR 8076 CNRS, Labex LERMIT, Faculté de Pharmacie, Université Paris‐Sud, Rue Jean‐Baptiste‐Clément, 92296 Châtenay Malabry Cedex</wicri:regionArea></affiliation></author><author><name sortKey="Bories, Christian" sort="Bories, Christian" uniqKey="Bories C" first="Christian" last="Bories">Christian Bories</name><affiliation wicri:level="1"><mods:affiliation>Groupe Chimiothérapie Antiparasitaire UMR 8076 CNRS, Labex LERMIT, Faculté de Pharmacie, Université Paris‐Sud, Rue Jean‐Baptiste‐Clément, 92296 Châtenay Malabry Cedex, France</mods:affiliation><country xml:lang="fr">France</country><wicri:regionArea>Groupe Chimiothérapie Antiparasitaire UMR 8076 CNRS, Labex LERMIT, Faculté de Pharmacie, Université Paris‐Sud, Rue Jean‐Baptiste‐Clément, 92296 Châtenay Malabry Cedex</wicri:regionArea></affiliation></author><author><name sortKey="Dumontet, Vincent" sort="Dumontet, Vincent" uniqKey="Dumontet V" first="Vincent" last="Dumontet">Vincent Dumontet</name><affiliation><mods:affiliation>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</mods:affiliation><wicri:noCountry code="subField">+33‐1‐69077247</wicri:noCountry></affiliation></author><author><name sortKey="Gueritte, Francoise" sort="Gueritte, Francoise" uniqKey="Gueritte F" first="Françoise" last="Guéritte">Françoise Guéritte</name><affiliation><mods:affiliation>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</mods:affiliation><wicri:noCountry code="subField">+33‐1‐69077247</wicri:noCountry></affiliation></author><author><name sortKey="Litaudon, Marc" sort="Litaudon, Marc" uniqKey="Litaudon M" first="Marc" last="Litaudon">Marc Litaudon</name><affiliation><mods:affiliation>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</mods:affiliation></affiliation><affiliation wicri:level="1"><mods:affiliation>E-mail: marc.litaudon@icsn.cnrs‐gif.fr</mods:affiliation><country wicri:rule="url">France</country></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">European Journal of Organic Chemistry</title><title level="j" type="alt">EUROPEAN JOURNAL OF ORGANIC CHEMISTRY</title><idno type="ISSN">1434-193X</idno><idno type="eISSN">1099-0690</idno><imprint><biblScope unit="vol">2012</biblScope><biblScope unit="issue">5</biblScope><biblScope unit="page" from="1039">1039</biblScope><biblScope unit="page" to="1046">1046</biblScope><biblScope unit="page-count">8</biblScope><publisher>WILEY‐VCH Verlag</publisher><pubPlace>Weinheim</pubPlace><date type="published" when="2012-02">2012-02</date></imprint><idno type="ISSN">1434-193X</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">1434-193X</idno></seriesStmt></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Eight new diarylheptanoid glucosides 1–8 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 1–4 were determined to be 3S and 5S by the application of the CD exciton chirality method to the corresponding 3,5‐bis(p‐bromobenzoyl) (1–3) 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.</div><div type="abstract" xml:lang="en">A story of serendipity: biologically inactive natural diarylheptanoid glucosides have been isolated from Pyrostria major. Their absolute configurations were determined to be 3S and 5S by the application of the CD exciton chirality method to the corresponding benzoyl derivatives. The study led to the discovery of new compounds possessing selective antiprotozoal activity.</div></front></TEI></record>Pour manipuler ce document sous Unix (Dilib)
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