Planta Med 2012; 78(09): 914-918
DOI: 10.1055/s-0031-1298459
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Dihydrochalcones and Benzoic Acid Derivatives from Piper dennisii

Billy Joel Cabanillas
1   Université de Toulouse, UPS, UMR 152 (Pharmacochimie et Pharmacologie pour le Développement-PHARMA DEV), Toulouse, France
2   IRD, UMR-152, Mission IRD casilla, Lima, Perú
,
Anne-Cécile Le Lamer
1   Université de Toulouse, UPS, UMR 152 (Pharmacochimie et Pharmacologie pour le Développement-PHARMA DEV), Toulouse, France
,
Denis Castillo
3   Laboratorios de Investigación y Desarrollo, Facultad de Ciencias y Filosofía, Universidad Peruana Cayetano Heredia, San Martin de Porres, Lima, Perú
,
Jorge Arevalo
3   Laboratorios de Investigación y Desarrollo, Facultad de Ciencias y Filosofía, Universidad Peruana Cayetano Heredia, San Martin de Porres, Lima, Perú
,
Yannick Estevez
1   Université de Toulouse, UPS, UMR 152 (Pharmacochimie et Pharmacologie pour le Développement-PHARMA DEV), Toulouse, France
2   IRD, UMR-152, Mission IRD casilla, Lima, Perú
,
Rosario Rojas
3   Laboratorios de Investigación y Desarrollo, Facultad de Ciencias y Filosofía, Universidad Peruana Cayetano Heredia, San Martin de Porres, Lima, Perú
,
Céline Valadeau
1   Université de Toulouse, UPS, UMR 152 (Pharmacochimie et Pharmacologie pour le Développement-PHARMA DEV), Toulouse, France
2   IRD, UMR-152, Mission IRD casilla, Lima, Perú
,
Geneviève Bourdy
1   Université de Toulouse, UPS, UMR 152 (Pharmacochimie et Pharmacologie pour le Développement-PHARMA DEV), Toulouse, France
2   IRD, UMR-152, Mission IRD casilla, Lima, Perú
,
Michel Sauvain
1   Université de Toulouse, UPS, UMR 152 (Pharmacochimie et Pharmacologie pour le Développement-PHARMA DEV), Toulouse, France
2   IRD, UMR-152, Mission IRD casilla, Lima, Perú
,
Nicolas Fabre
1   Université de Toulouse, UPS, UMR 152 (Pharmacochimie et Pharmacologie pour le Développement-PHARMA DEV), Toulouse, France
› Author Affiliations
Further Information

Publication History

received 11 December 2011
revised 14 March 2012

accepted 21 March 2012

Publication Date:
19 April 2012 (online)

Abstract

Two new dihydrochalcones (1, 2), as well as eight known compounds, piperaduncin C (3), 2′,6′-dihydroxy-4′-methoxydihydrochalcone (4), 4,2′,6′-trihydroxy-4′-methoxydihydrochalcone (5), 4-hydroxy-3,5-bis(3-methyl-2-butenyl)-benzoic acid (6), 3,5-bis(3-methyl-2-butenyl)-4-methoxybenzoic acid (7), 4-hydroxy-3-(3-methyl-2-butenoyl)-5-(3-methyl-2-butenyl)-benzoic acid (8), 2,2-dimethyl-8-(3-methyl-2-butenyl)-2H-1-chromene-6-carboxylic acid (9), and 3-(3′,7′-dimethyl-2′,6′-octadienyl)-4-methoxybenzoic acid (10) were isolated from the leaves of Piper dennisii Trelease (Piperaceae), using a bioassay-guided fractionation to determine their antileishmanial potential. Among them, compound 10 exhibited the best antileishmanial activity (IC50 = 20.8 µM) against axenic amastigote forms of Leishmania amazonensis, with low cytotoxicity on murine macrophages. In the intracellular macrophage-infected model, compound 10 proved to be more active (IC50 = 4.2 µM). The chemical structures of compounds 110 were established based on the analysis of the spectroscopic data.

Supporting Information

 
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