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Methyl 4-hydroxy-3-(3'-methyl-2'-butenyl)benzoate, major insecticidal principle from Piper guanacastensis. 1997
R Pereda-Miranda, and
C B Bernard, and
T Durst, and
J T Arnason, and
P Sánchez-Vindas, and
L Poveda, and
L San Román
Departamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México, Coyoacán, D.F., Mexico. pereda@servidor.unam.mx
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.
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