Benzoic acid derivatives from Piper species and their antiparasitic activity.
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.
Flores
Ninoska
N
Instituto Universitario de Bio-Orgánica Antonio González, Universidad de La Laguna, Avenida Astrofísico Francisco Sánchez 2, La Laguna, 38206 Tenerife, Canary Islands, Spain.
Jiménez
Ignacio A
IA
Giménez
Alberto
A
Ruiz
Grace
G
Gutiérrez
David
D
Bourdy
Genevieve
G
Bazzocchi
Isabel L
IL
D000818:Animals; D000962:Antimalarials; D000977:Antiparasitic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000981:Antiprotozoal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001565:Benzoates / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001838:Bolivia; D007891:Leishmania / Q000187:drug effects; D015394:Molecular Structure; D021261:Parasitic Sensitivity Tests; D031701:Piper / Q000737:chemistry*; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D010963:Plasmodium falciparum / Q000187:drug effects; D014349:Trypanosoma cruzi / Q000187:drug effects
D000962:Antimalarials; D000977:Antiparasitic Agents; D000981:Antiprotozoal Agents; D001565:Benzoates