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.
PY - 2008/9
Y1 - 2008/9
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 μg/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 μg/mL, respectively.
AB - 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 μg/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 μg/mL, respectively.
UR - http://www.scopus.com/inward/record.url?scp=54149103287&partnerID=8YFLogxK
U2 - 10.1021/np800104p
DO - 10.1021/np800104p
M3 - Artículo
C2 - 18712933
AN - SCOPUS:54149103287
SN - 0163-3864
VL - 71
SP - 1538
EP - 1543
JO - Journal of Natural Products
JF - Journal of Natural Products
IS - 9
ER -