Repositorio
Institucional

Espinoza, Javier

Urzua, Alejandro#Bardehle, Leonardo#Quiroz, Andres#Echeverria, Javier#Gonzalez-Teuber, Marcia

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

MDPI

MOLECULES

en

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.

Artículo original

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.

Esta investigación fue financiada por: Beca FONDECYT No. 1141245, Beca FONDECYT No. 3130327, USACH Proyecto Basal USA 1799, CONICYT PAI/ACADEMIA No. 79160109 y Beca CONICYT-PCHA No. 2012-21120365.

10.3390/molecules23061282

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Hylastinus obscurus# red clover# essential oils# sesquiterpenes# antifeedant effects# lipophilicity# vapor pressure

http://dx.doi.org/10.3390/molecules23061282

Biochemistry & Molecular Biology# Chemistry, Multidisciplinary

Hylastinus oscuro# trébol rojo# aceites esenciales# sesquiterpenos# efectos antialimentarios# lipofilicidad# presión de vapor

Fitomejoramiento y protección vegetal

Zoología, Ornitología, Entomología y Comportamiento Biológico

Química Orgánica

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verde

acceso abierto

acceso abierto

WOS:000435875400044

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)

Artículo original

MDPI

MOLECULES

Bioquímica y Biología Molecular# Química, Multidisciplinar

en

ANID FONDECYT 1141245#ANID FONDECYT 3130327#USACH Proyecto Basal USA 1799#ANID CONICYT PAI/ACADEMIA 79160109#ANID CONICYT-PCHA 21120365.

ANID FONDECYT 1141245

ANID FONDECYT 3130327

USACH Proyecto Basal USA 1799

ANID CONICYT PAI/ACADEMIA 79160109

ANID CONICYT-PCHA 2012-21120365

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.

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