title: Dihydrochalcones and benzoic acid derivatives from Piper dennisii.
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.
authors.affiliation: Université de Toulouse, UPS, UMR 152 (Pharmacochimie et Pharmacologie pour le Développement-PHARMA DEV), Toulouse, France.
authors.forename: Billy Joel
authors.initials: BJ
authors.lastname: Cabanillas
authors.forename: Anne-Cécile
authors.initials: AC
authors.lastname: Le Lamer
authors.forename: Denis
authors.initials: D
authors.lastname: Castillo
authors.forename: Jorge
authors.initials: J
authors.lastname: Arevalo
authors.forename: Yannick
authors.initials: Y
authors.lastname: Estevez
authors.forename: Rosario
authors.initials: R
authors.lastname: Rojas
authors.forename: Céline
authors.initials: C
authors.lastname: Valadeau
authors.forename: Geneviève
authors.initials: G
authors.lastname: Bourdy
authors.forename: Michel
authors.initials: M
authors.lastname: Sauvain
authors.forename: Nicolas
authors.initials: N
authors.lastname: Fabre
mesh_terms: D000818:Animals; D000981:Antiprotozoal Agents / Q000737:chemistry / Q000494:pharmacology*; D001565:Benzoates / Q000737:chemistry / Q000494:pharmacology; D019817:Benzoic Acid / Q000737:chemistry; D047188:Chalcones / Q000737:chemistry* / Q000494:pharmacology*; D004353:Drug Evaluation, Preclinical / Q000379:methods; D062425:Hydroxybenzoate Ethers; D020128:Inhibitory Concentration 50; D007891:Leishmania / Q000187:drug effects*; D017737:Macrophages, Peritoneal / Q000187:drug effects / Q000469:parasitology; D051379:Mice; D015394:Molecular Structure; D031701:Piper / Q000737:chemistry*; D018515:Plant Leaves / Q000737:chemistry
chemical_list: C424502:2',6'-dihydroxy-4'-methoxydihydrochalcone; C121078:3-(3',7'-dimethyl-2',6'-octadienyl)-4-methoxybenzoic acid; D000981:Antiprotozoal Agents; D001565:Benzoates; D047188:Chalcones; D062425:Hydroxybenzoate Ethers; D019817:Benzoic Acid