Methyl 4-hydroxy-3-(3'-methyl-2'-butenyl)benzoate, major insecticidal principle from Piper guanacastensis.
The CHCl3-soluble extract of Piper guanacastensis (Piperaceae) was found to have noteworthy insecticidal activity to Aedes atropalpus mosquito larvae (LC50 80.5 micrograms/mL). Bioassay-guided fractionation afforded methyl 4-hydroxy-3-(3'-methyl-2'-butenyl)benzoate (1) as the major bioactive constituent (LC50 20.5 micrograms/mL). The separation of compound 1 from its transesterification artifact (2), ethyl 4-hydroxy-3-(3'-methyl-2'-butenyl)benzoate, was achieved by recycling reversed-phase HPLC. The flavonoids acacetin, chrysin, and pinostrobin were also isolated from the active fraction but did not display insecticidal properties.
Pereda-Miranda
R
R
Departamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México, Coyoacán, D.F., Mexico. pereda@servidor.unam.mx
Bernard
C B
CB
Durst
T
T
Arnason
J T
JT
Sánchez-Vindas
P
P
Poveda
L
L
San Román
L
L
D000330:Aedes; D000818:Animals; D002855:Chromatography, Thin Layer; D007306:Insecticides / Q000302:isolation & purification* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010226:Parabens / Q000302:isolation & purification* / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet
D007306:Insecticides; D010226:Parabens; C105637:methyl 4-hydroxy-3-(3'-methyl-2'-butenyl)benzoate