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Benzoic acid derivatives from Piper species and their antiparasitic activity.
J Nat Prod. 2008 Sep; 71(9):1538-43.JN

Abstract

Piper glabratum and P. acutifolium were analyzed for their content of main secondary constituents, affording nine new benzoic acid derivatives (1, 2, 4, 5, 7, and 10-13), in addition to four known compounds (3, 6, 8, and 9). Their structures were elucidated on the basis of spectroscopic data. Riguera ester reactions and optical rotation measurements established the new compounds as racemates. In the search for antiparasitic agents, the compounds were evaluated in vitro against the promastigote forms of Leishmania spp., Trypanosoma cruzi, and Plasmodium falciparum. Among the evaluated compounds, methyl 3,4-dihydroxy-5-(3'-methyl-2'-butenyl)benzoate (7) exhibited leishmanicidal effect (IC50 13.8-18.5 microg/mL) against the three Leishmania strains used, and methyl 3,4-dihydroxy-5-(2-hydroxy-3-methylbutenyl)benzoate (1), methyl 4-hydroxy-3-(2-hydroxy-3-methyl-3-butenyl)benzoate (3), and methyl 3,4-dihydroxy-5-(3-methyl-2-butenyl) benzoate (7) showed significant trypanocidal activity, with IC50 values of 16.4, 15.6, and 18.5 microg/mL, respectively.

Authors+Show Affiliations

Instituto Universitario de Bio-Orgánica Antonio González, Universidad de La Laguna, Avenida Astrofísico Francisco Sánchez 2, La Laguna, 38206 Tenerife, Canary Islands, Spain.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

18712933

Citation

Flores, Ninoska, et al. "Benzoic Acid Derivatives From Piper Species and Their Antiparasitic Activity." Journal of Natural Products, vol. 71, no. 9, 2008, pp. 1538-43.
Flores N, Jiménez IA, Giménez A, et al. Benzoic acid derivatives from Piper species and their antiparasitic activity. J Nat Prod. 2008;71(9):1538-43.
Flores, N., Jiménez, I. A., Giménez, A., Ruiz, G., Gutiérrez, D., Bourdy, G., & Bazzocchi, I. L. (2008). Benzoic acid derivatives from Piper species and their antiparasitic activity. Journal of Natural Products, 71(9), 1538-43. https://doi.org/10.1021/np800104p
Flores N, et al. Benzoic Acid Derivatives From Piper Species and Their Antiparasitic Activity. J Nat Prod. 2008;71(9):1538-43. PubMed PMID: 18712933.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Benzoic acid derivatives from Piper species and their antiparasitic activity. AU - Flores,Ninoska, AU - Jiménez,Ignacio A, AU - Giménez,Alberto, AU - Ruiz,Grace, AU - Gutiérrez,David, AU - Bourdy,Genevieve, AU - Bazzocchi,Isabel L, Y1 - 2008/08/20/ PY - 2008/8/21/pubmed PY - 2008/11/13/medline PY - 2008/8/21/entrez SP - 1538 EP - 43 JF - Journal of natural products JO - J Nat Prod VL - 71 IS - 9 N2 - Piper glabratum and P. acutifolium were analyzed for their content of main secondary constituents, affording nine new benzoic acid derivatives (1, 2, 4, 5, 7, and 10-13), in addition to four known compounds (3, 6, 8, and 9). Their structures were elucidated on the basis of spectroscopic data. Riguera ester reactions and optical rotation measurements established the new compounds as racemates. In the search for antiparasitic agents, the compounds were evaluated in vitro against the promastigote forms of Leishmania spp., Trypanosoma cruzi, and Plasmodium falciparum. Among the evaluated compounds, methyl 3,4-dihydroxy-5-(3'-methyl-2'-butenyl)benzoate (7) exhibited leishmanicidal effect (IC50 13.8-18.5 microg/mL) against the three Leishmania strains used, and methyl 3,4-dihydroxy-5-(2-hydroxy-3-methylbutenyl)benzoate (1), methyl 4-hydroxy-3-(2-hydroxy-3-methyl-3-butenyl)benzoate (3), and methyl 3,4-dihydroxy-5-(3-methyl-2-butenyl) benzoate (7) showed significant trypanocidal activity, with IC50 values of 16.4, 15.6, and 18.5 microg/mL, respectively. SN - 1520-6025 UR - https://www.unboundmedicine.com/medline/citation/18712933/Benzoic_acid_derivatives_from_Piper_species_and_their_antiparasitic_activity_ L2 - https://doi.org/10.1021/np800104p DB - PRIME DP - Unbound Medicine ER -