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Dihydrochalcones and benzoic acid derivatives from Piper dennisii.
Planta Med. 2012 Jun; 78(9):914-8.PM

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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Authors+Show Affiliations

Cabanillas BJ
Université de Toulouse, UPS, UMR 152 (Pharmacochimie et Pharmacologie pour le Développement-PHARMA DEV), Toulouse, France.
Le Lamer AC
No affiliation info available
Castillo D
No affiliation info available
Arevalo J
No affiliation info available
Estevez Y
No affiliation info available
Rojas R
No affiliation info available
Valadeau C
No affiliation info available
Bourdy G
No affiliation info available
Sauvain M
No affiliation info available
Fabre N
No affiliation info available

MeSH

AnimalsAntiprotozoal AgentsBenzoatesBenzoic AcidChalconesDrug Evaluation, PreclinicalHydroxybenzoate EthersInhibitory Concentration 50LeishmaniaMacrophages, PeritonealMiceMolecular StructurePiperPlant Leaves

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

22516933

Citation

Cabanillas, Billy Joel, et al. "Dihydrochalcones and Benzoic Acid Derivatives From Piper Dennisii." Planta Medica, vol. 78, no. 9, 2012, pp. 914-8.
Cabanillas BJ, Le Lamer AC, Castillo D, et al. Dihydrochalcones and benzoic acid derivatives from Piper dennisii. Planta Med. 2012;78(9):914-8.
Cabanillas, B. J., Le Lamer, A. C., Castillo, D., Arevalo, J., Estevez, Y., Rojas, R., Valadeau, C., Bourdy, G., Sauvain, M., & Fabre, N. (2012). Dihydrochalcones and benzoic acid derivatives from Piper dennisii. Planta Medica, 78(9), 914-8. https://doi.org/10.1055/s-0031-1298459
Cabanillas BJ, et al. Dihydrochalcones and Benzoic Acid Derivatives From Piper Dennisii. Planta Med. 2012;78(9):914-8. PubMed PMID: 22516933.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Dihydrochalcones and benzoic acid derivatives from Piper dennisii. AU - Cabanillas,Billy Joel, AU - Le Lamer,Anne-Cécile, AU - Castillo,Denis, AU - Arevalo,Jorge, AU - Estevez,Yannick, AU - Rojas,Rosario, AU - Valadeau,Céline, AU - Bourdy,Geneviève, AU - Sauvain,Michel, AU - Fabre,Nicolas, Y1 - 2012/04/19/ PY - 2012/4/21/entrez PY - 2012/4/21/pubmed PY - 2012/10/27/medline SP - 914 EP - 8 JF - Planta medica JO - Planta Med VL - 78 IS - 9 N2 - 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. SN - 1439-0221 UR - https://www.unboundmedicine.com/medline/citation/22516933/Dihydrochalcones_and_benzoic_acid_derivatives_from_Piper_dennisii_ L2 - http://www.thieme-connect.com/DOI/DOI?10.1055/s-0031-1298459 DB - PRIME DP - Unbound Medicine ER -