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Caffeic Acid Esters and Lignans from Piper sanguineispicum

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Université de Toulouse, UPS, UMR 152 (Laboratoire de Pharmacochimie des Substances Naturelles et Pharmacophores Redox), F-31062 Toulouse Cedex 9, France, IRD, UMR-152, Mission IRD Casilla 18-1209 Lima, Perú, and Laboratorios de Investigación y Desarrollo, Facultad de Ciencias y Filosofía, Universidad Peruana Cayetano Heredia, Avenida Honorio Delgado 430, San Martin de Porres, Lima, Perú
* To whom correspondence should be addressed. Tel: +33-5-62256848. Fax: +33-5-61554330. E-mail: [email protected]; [email protected]
†Université de Toulouse.
‡Mission IRD, Perú.
§Universidad Peruana Cayetano Heredia.
Cite this: J. Nat. Prod. 2010, 73, 11, 1884–1890
Publication Date (Web):October 18, 2010
https://doi.org/10.1021/np1005357
Copyright © 2010 The American Chemical Society and American Society of Pharmacognosy

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    Abstract

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    Three new caffeic acid esters (13), four new lignans (47), and the known compounds (7′S)-parabenzlactone (8), dihydrocubebin (9), and justiflorinol (10) have been isolated from leaves of Piper sanguineispicum. Their structures were determined by spectroscopic methods, including 1D and 2D NMR, HRCIMS, CD experiments, and chemical methods. Compounds 110 were assessed for their antileishmanial potential against axenic amastigote forms of Leishmania amazonensis. Caffeic acid esters 1 and 3 exhibited the best antileishmanial activity (IC50 2.0 and 1.8 μM, respectively) with moderate cytotoxicity on murine macrophages.

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    1H and 13C NMR spectra of compounds 17. This material is available free of charge via the Internet at http://pubs.acs.org.

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