Antifeedant Effects of Essential Oil, Extracts, and Isolated Sesquiterpenes from Pilgerodendron uviferum (D. Don) Florin Heartwood on Red Clover Borer Hylastinus obscurus (Coleoptera: Curculionidae)

Primer Autor
Espinoza, Javier
Co-autores
Urzua, Alejandro#Bardehle, Leonardo#Quiroz, Andres#Echeverria, Javier#Gonzalez-Teuber, Marcia
Título
Antifeedant Effects of Essential Oil, Extracts, and Isolated Sesquiterpenes from Pilgerodendron uviferum (D. Don) Florin Heartwood on Red Clover Borer Hylastinus obscurus (Coleoptera: Curculionidae)
Editorial
MDPI
Revista
MOLECULES
Lenguaje
en
Resumen
The beetle Hylastinus obscurus Marsham (Coleoptera: Curculionidae), endemic to Europe and Northern Africa, is one of the most important red clover pests in Chile. As commercial insecticides are less effective against this pest, plant secondary metabolites have been considered as an alternative for its control. Here, we have investigated the chemical composition of essential oil (EO), petroleum ether extract (PEE), and dichloromethane extract (DCME) from Pilgerodendron uviferum heartwood. Additionally, the effects of EO and extracts on the feeding behavior (% of weight shift) of H. obscurus have been evaluated. The composition of EO, PEE, and DCME were analyzed using gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS). The results showed the presence of a similar mixture of sesquiterpenes in the essential oil and in both of the extracts, which accounted for circa 60% of the total mixture. Sesquiterpenes were further isolated using chromatographic methods and were structurally characterized by optical rotation, GC-MS, FTIR, and 1D and 2D NMR experiments. The physicochemical properties of the isolated sesquiterpenes, including lipophilicity and vapor pressure, were also determined. The sesquiterpenes were identified as the following: (-)-trans-calamenene (1), cadalene (2), (-)-cubenol (3), (-)-epi-cubenol (4), (-)-torreyol (5), and ()-15-copaenol (6). The antifeedant activity of EO, extracts, and isolated sesquiterpenes were evaluated using artificial diets in a non-choice test. Relative to the control, the EO, DCME extract, and the isolated sesquiterpenes, namely, (-)-trans-calamenene (1), cadalene (2), and (5) torreyol, were found to be the most effective treatments against H. obscurus. Our study showed that the compounds occurring in P. uviferum heartwood were effective in reducing the adult growth of H. obscurus. The physicochemical properties of the isolated sesquiterpenes might have been associated with antifeedant effects.
Tipo de Recurso
Artículo original
Description
This research was funded by: FONDECYT grant No. 1141245, FONDECYT grant No. 3130327, USACH Proyecto Basal USA 1799, CONICYT PAI/ACADEMIA No. 79160109 and CONICYT-PCHA grant No. 2012-21120365.
doi
10.3390/molecules23061282
Formato Recurso
pdf
Palabras Claves
Hylastinus obscurus# red clover# essential oils# sesquiterpenes# antifeedant effects# lipophilicity# vapor pressure
Hylastinus obscurus# red clover# essential oils# sesquiterpenes# antifeedant effects# lipophilicity# vapor pressure
Ubicación del archivo
http://dx.doi.org/10.3390/molecules23061282
Categoría OCDE
Biochemistry & Molecular Biology# Chemistry, Multidisciplinary
Materias
Hylastinus oscuro# trébol rojo# aceites esenciales# sesquiterpenos# efectos antialimentarios# lipofilicidad# presión de vapor
Hylastinus oscuro# trébol rojo# aceites esenciales# sesquiterpenos# efectos antialimentarios# lipofilicidad# presión de vapor
Id de Web of Science
WOS:000435875400044
Título de la cita (Recomendado-único)
Antifeedant Effects of Essential Oil, Extracts, and Isolated Sesquiterpenes from <i>Pilgerodendron</i> <i>uviferum</i> (D. Don) Florin Heartwood on Red Clover Borer <i>Hylastinus obscurus</i> (Coleoptera: Curculionidae)
Identificador del recurso (Mandatado-único)
Artículo original
Versión del recurso (Recomendado-único)
version publicada
Editorial
MDPI
Revista/Libro
MOLECULES
Categoría WOS
Bioquímica y Biología Molecular# Química, Multidisciplinar
Idioma
en
Referencia del Financiador (Mandatado si es aplicable-repetible)
ANID FONDECYT 1141245#ANID FONDECYT 3130327#USACH Proyecto Basal USA 1799#ANID CONICYT PAI/ACADEMIA 79160109#ANID CONICYT-PCHA 21120365.
Descripción
This research was funded by: FONDECYT grant No. 1141245, FONDECYT grant No. 3130327, USACH Proyecto Basal USA 1799, CONICYT PAI/ACADEMIA No. 79160109 and CONICYT-PCHA grant No. 2012-21120365.
Formato
pdf
Tipo de ruta
dorada#verde
Access Rights
acceso abierto
Derechos de acceso
acceso abierto
License
CC BY
Página de inicio (Recomendado-único)
276
Página final (Recomendado-único)
282
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