Dihydrochalcones and Benzoic Acid Derivatives from Piper dennisii

 

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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 1–10 were established based on the analysis of the spectroscopic data.

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