La composición del aceite esencial (AE) obtenido por hidrodestilación de hojas secas de Heliotropium stenophyllum (Heliotropiaceae) se  analizó mediante cromatografía de gases (CG) y cromatografía de gases/espectrometría de masas (CG/EM). La actividad insecticida del  aceite contra la mosca doméstica Musca domestica se evaluó y la dosis necesaria para matar el 50% de las moscas (LC50) en 2 h se  determinó a 25 ± 1 ºC. El aceite esencial de Heliotropium stenophyllum mostró potentes propiedades insecticidas (LC50 = 1,09 mg/dm3) en  comparación con otros aceites esenciales, en el que en tiempos más cortos, se utilizó el mismo bio-ensayo. De acuerdo con los análisis  de  CG y CG/EM, junenol (19,08%); longiborneol (9,34%), (E, Z)-geranil linalool (6,81%); selina-3,11-dien-6-α-ol (6,70% ); epoxido de α-  cedreno (6,60%); heliofolen-12-al D (6,23%) y β-epi-bisabolol (4,83%) fueron los componentes principales identificados en el AE. El aceite  esencial de Heliotropium stenophyllum, formado exclusivamente por sesquiterpenos, mostró una composición muy diferente al de los AEs  de otras especies de Heliotropium, estudiadas, y muestra un gran potencial como insecticida contra la moscas doméstica

Echeverría, Javier

Heit, Cecilia

Modak, Brenda

Santander, Rocío

Urzúa, Alejandro

English

Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas

  
© 2013 Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas 12 (2): 196 - 200 
 ISSN 0717 7917 
www.blacpma.usach.cl 
 
 
Artículo Original | Original Article 
196 
 
 
Insecticidal properties of Heliotropium stenophyllum essential 
oil on the House fly, Musca domestica L. 
 
[Propiedades insecticidas del aceite esencial de Heliotropium stenophyllum en la  
mosca doméstica, Musca domestica L.] 
 
 
Alejandro URZÚA1, Brenda MODAK1, Rocío SANTANDER1, Cecilia HEIT2 & Javier ECHEVERRÍA3 
 
 
1Facultad de Química y Biología, Departamento de Ciencias del Ambiente, Universidad de Santiago de Chile, Santiago, Chile 
2Facultad de Ingeniería, Laboratorio de Análisis de Residuos y Trazas, Universidad Nacional de Jujuy, Argentina 
3Departamento de Ciencias Ecológicas, Facultad de Ciencias, Universidad de Chile, Santiago, Chile 
Contactos | Contacts: Alejandro URZÚA - E-mail address: alejandro.urzua@usach.cl 
 
Abstract  
The composition of the essential oil (EO) obtained by hydro distillation from dry leaves of Heliotropium stenophyllum (Heliotropiaceae) 
was analyzed using gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS). The insecticidal activity of the oil 
against the house fly Musca domestica was evaluated and the dose necessary to kill 50% of flies (LC50) in 2 h was determined at 25 ± 1 °C. 
The essential oil from Heliotropium stenophyllum showed potent insecticidal properties (LC50 = 1.09 mg/dm
3) in comparison with other 
essential oils, in which at shorter times, the same bio-assay was used. According to GC and GC/MS analysis, junenol (19.08%); 
longiborneol (9.34%); (E, Z)-geranyl linalool (6.81%); selina-3,11-dien-6-α-ol (6.70%); α-cedrene epoxide (6.60%); heliofolen-12-al D 
(6.23%) and β-epi-bisabolol (4.83%)  were the principal components of the EO. The Heliotropium stenophyllum essential oil, made up 
exclusively of sesquiterpenes, showed a composition very different from the EOs of the other species of Heliotropium, studied, and present 
a great  potential as a natural insecticide against houseflies. 
 
Keywords:  Heliotropium stenophyllum essential oil composition; sesquiterpenoids; vapour pressure; Musca domestica; natural insecticide 
 
Resumen 
La composición del aceite esencial (AE) obtenido por hidrodestilación de hojas secas de Heliotropium stenophyllum (Heliotropiaceae) se 
analizó mediante cromatografía de gases (CG) y cromatografía de gases/espectrometría de masas (CG/EM). La actividad insecticida del 
aceite contra la mosca doméstica Musca domestica se evaluó y la dosis necesaria para matar el 50% de las moscas (LC50) en 2 h se 
determinó a 25 ± 1 ºC. El aceite esencial de Heliotropium stenophyllum mostró potentes propiedades insecticidas (LC50 = 1,09 mg/dm
3) en 
comparación con otros aceites esenciales, en el que en tiempos más cortos, se utilizó el mismo bio-ensayo. De acuerdo con los análisis  de 
CG y CG/EM, junenol (19,08%); longiborneol (9,34%), (E, Z)-geranil linalool (6,81%); selina-3,11-dien-6-α-ol (6,70% ); epoxido de α-
cedreno (6,60%); heliofolen-12-al D (6,23%) y β-epi-bisabolol (4,83%) fueron los componentes principales identificados en el AE. El aceite 
esencial de Heliotropium stenophyllum, formado exclusivamente por sesquiterpenos, mostró una composición muy diferente al de los AEs 
de otras especies de Heliotropium, estudiadas, y muestra un gran potencial como insecticida contra la moscas doméstica. 
 
Palabras Clave: Composición del aceite esencial de Heliotropium stenophyllum; sesquiterpenos; presión de vapor, Musca domestica; 
Insecticida natural  
 
 
 
  
Recibido | Received: December 4, 2012 
Aceptado en versión corregida | Accepted in revised form: January 15, 2013 
Publicado en línea | Published online: March 30, 2013 
Declaración de intereses | Declaration of interests: Financial support for this work was provided by Universidad de Santiago de Chile, DICYT, 020941UM. 
Este artículo puede ser citado como / This article must be cited as: A Urzúa, B Modak, R Santander, C Heit, J Echeverría. 2013. Insecticidal properties of Heliotropium 
stenophyllum essential oil on the House fly, Musca domestica L. Bol Latinoam Caribe Plant Med Aromat 12(2): 196 – 200.  
Urzúa et al. Insecticidal properties of Heliotropium stenophyllum essential oil 
Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas/197 
 
INTRODUCTION 
In our continuing interest in the potential of essential 
oils (EOs) as insecticides against Musca domestica 
(Urzúa et al., 2010a; Urzúa et al., 2010b), we present 
an evaluation of the insecticidal properties of a 
species endemic to arid and semi-arid regions of 
Chile, Heliotropium stenophyllum Hook.et Arn. 
(Heliotropiaceae) (Johnston, 1928). The choice of 
this specie was motivated by field observations of 
their apparent resistance to insect aggression and a 
key factor in its selection was that the cuticle 
components of leaves, obtained by CH2Cl2 extraction, 
showed antiffedant properties against larvae of Pieris 
brassicae (Villarroel et al., 1991). 
We previously reported that Heliotropium 
stenophyllum contains a mixture of 2-geranyl-4-
hydroxyphenyl acetate and several known flavonoids 
but the composition of essential oil from 
Heliotropium stenophyllum was never been 
investigated  (Villarroel et al., 1991).  
In addition, as far as we are concerned, the 
composition of essential oils from only two species 
of Heliotropium, species have been investigated.   
The essential oil of Heliotropium indicum 
was obtained in 0.004% and the major identified 
constituents were phytol (49.1%); 1-dodecanol 
(6.4%) and β-linalool (3.0%). In addition, long chain 
alcohols and hydrocarbons gave account of 11.8% of 
the components.  The EO showed significant activity 
against Mycobacterium tuberculosis (Machan et al., 
2006). 
The essential oil of Heliotropium europaeum 
was obtained in 0.1% and the major constituents were 
phytol (28.7%); cis-linoleic acid methyl ester (7.3%); 
silphiperphol-6-en-5-one (7.1%); geranyl acetone 
(6.3%); (E)-β-ionone (4.8%); phytol acetate (4.3%) 
and alloaromadendrene epoxide (3.8%). In addition, 
long chain alcohols and hydrocarbons gave account 
of 19.2% of the components. The essential oil show 
low antimicrobial activity (Saeedi and Morteza-
Semnani, 2009). 
 
MATERIAL AND METHODS 
General 
The essential-oil component analysis was performed 
by gas chromatography and gas chromatography/ 
mass spectroscopy (GC/MS). Qualitative analyses 
were performed in a Hewlett-Packard 6890 gas 
chromatograph linked to a Hewlett-Packard 5972 A 
mass spectrometric detector with an integrated data 
system (Hewlett Packard, Palo Alto, CA, USA); 
quantitative analyses were carried out with a 
Shimadzu GC-9A gas chromatograph fitted with a 
FID-9 detector (Shimadzu Corporation, Kyoto, 
Japan). The same capillary column (HP-5 MS, film 
thickness 0.25 μm, 30 m x 0.25 mm, Agilent, USA) 
was used in both instruments.  
 
Plant material 
Leaves of H.stenophyllum, were collected in 
November 2010, in Los Vilos, IV Region Chile 
(32º52’S, 71º29’W). Voucher specimens (ST-2560) 
were deposited in the Herbarium of the National 
Natural History Museum, Santiago, Chile 
 
Essential oil extraction and analysis 
Essential oils were extracted from 100 g of dry leaves 
for 4 h by hydro distillation in a Clevenger-type 
apparatus. The EO was dried over anhydrous sodium 
sulfate. The EO component analysis was performed 
by gas chromatography and gas 
chromatography/mass spectroscopy (GC/MS) using 
the instrumentation described above. The operating 
conditions were as follows: on-column injection; 
injector temperature, 250 °C; detector temperature, 
280 °C; carrier gas, He at 1.0 ml/min; oven 
temperature program: 60 ºC  increase to 260 ºC at 4 
ºC/min, and then 260 ºC for 5 min. The mass detector 
ionization employed an electron impact of 70 eV. 
Recording conditions employed a scan time of 1.5 s 
and a mass range of 41 to 450 amu. Compounds in 
the chromatograms were identified by comparison of 
their mass spectra with those in the NIST2008 library 
database, and by comparison of their calculated 
retention index with those reported in the literature.  
 
Fly collection and maintenance 
Adult flies were obtained from 12 h pupae 
commercially obtained. Pupae of M. domestica were 
transferred to entomological cages (30×30×30 cm) at 
25 ± 1 °C under a 12:12 light: dark cycle and 65% 
humidity. Emerged adult flies were provided with 
water and fed 1:1 (v/v; approximately) mixture of 
sugar and powdered milk.  
 
Bioassay 
The bioassay was designed such that the flies would 
have high probability of coming into contact with the 
volatile compounds within two hour test period; 
therefore, the flies were allowed access to the total 
Urzúa et al. Insecticidal properties of Heliotropium stenophyllum essential oil 
Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas/198 
 
space within the exposure vessel. Ten 3 day-old adult 
house flies, of both sexes, were placed in a glass jar 
(1.0 dm
3
) fitted with a screw cap with a 6-cm length 
of cotton yarn suspended from the center of the 
internal face of the cap. Different dosages of pure EO 
(without solvent) were applied to the yarn. The 
control vessel had no compound on the cotton yarn. 
The jars were then sealed tightly. The jars were 
maintained in a room at 25 ± 1 °C. Each test was 
replicated three times. The assay was also run with 
the cotton yarn enclosed in a bag made of breathable 
cloth so that the flies could not contact the yarn. 
Dimethyl 2, 2-dichlorovinyl phosphate (DDVP), a 
volatile organophosphate, was used as a positive 
control. Mortality in each group was assessed after a 
two our exposure. 
 
Data analysis 
The mean mortality data of the three replicates per 
doses (5 doses) was used to calculate the LC50. Probit 
analysis (Harvard Programming; Hg1, 2) was used to 
analyze the dose-mortality response. 
 
 
Table Nº 1 
Essential oil Composition of leaves of Heliotropium stenophyllum 
Compound RI % Identification 
α-Gurjunene  
β-Dihydroagarofuran 
α-Amorphene  
γ-Cadinene 
α-Agarofuran 
Silphiperfol-5-en-3-ol 
Spathulenol     
α-Cedren epoxide            
Longiborneol 
Heliofolen-12-al-D 
cis-Isolongi- folanone 
10-epi-γ-Eudesmol 
Junenol                                                                                                                                                                                                                                                                                                                                                           
2-epi-α-Cedren-3-one 
Cedren-9-one      
α-Eudesmol 
α-Muurolol 
Agarospirol 
Selina-3,11-dien-6-α-ol 
β-epi-Bisabolol 
Eudesma-4(15)-7-dien-1-β-ol  
Cedroxyde  
(E)-Nuciferal 
Eremophilone 
Aristolone 
Bisabolol acetate 
β-Chenopodiol 
(E,Z) Geranyl linalool                                                                                                     
1409 
1497                                               
1512 
1513 
1542 
1550 
1578 
1589 
1598 
1607 
1611 
1617 
1622 
1627 
1633 
1636 
1643 
1645 
1650 
1669 
1679 
1708 
1726 
1734 
1764 
1797 
1810 
1988 
0.462 
0.901 
0.444 
0.842 
0.602 
2.21 
4.35 
6.59 
9.34 
6.23 
1.49 
1.32 
19.08 
1.92 
3.10 
4.10 
3.95 
3.70 
6.70 
4.83 
3.56 
1.56 
1.24 
1.29 
1.34 
1.18 
1.30 
6.81 
RI, MS 
RI, MS 
RI, MS 
RI, MS 
RI, MS 
RI, MS 
RI, MS 
RI, MS 
RI, MS 
RI, MS 
RI, MS 
RI, MS 
RI, MS 
RI, MS 
RI, MS 
RI, MS 
RI, MS 
RI, MS 
RI, MS 
RI, MS 
RI, MS 
RI, MS 
RI, MS 
RI, MS 
RI, MS 
RI, MS 
RI, MS 
RI, MS 
RI: retention index 
 
Urzúa et al. Insecticidal properties of Heliotropium stenophyllum essential oil 
Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas/199 
 
Table Nº 2 
LC50 of EO of Heliotropium stenophyllum on Musca domestica 
Time Mean LC50 in mg/dm
3 
(95% CI) 
½ h 13.21 (4.69 – 21.34) 
1 h 5.26 (2.31 – 10.34) 
2 h 1.09 (2.69 – 14.54) 
 
 
RESULTS AND DISCUSION 
In this communication from the dry leaves of H. 
stenophyllum (100 g), 0.57 g (0.57%) of EO was 
obtained. The composition of the EO (%) is listed in 
Table Nº 1, 28 compounds were identified : junenol 
(19.08%); longiborneol (9.34%); (E, Z)-geranyl 
linalool (6.81%); selina-3,11-dien-6-α-ol (6.70%); α-
cedren epoxide (6.59%); heliofolen-12-al D (6.23%) 
β-epi-bisabolol (4.83),  were the major constituents 
identified in the EO.  
The H. stenophyllum essential oil, made up 
exclusively of sesquiterpenes, showed a composition 
very different from the EOs of the other species of 
Heliotropium, studied in which  phytol is the 
characteristic major constituent, with long chain 
hydrocarbons and alcohols. 
Recently, the insecticide activity of 12 EOs 
from edible plants, were screened against housefly 
adults  and the dose necessary to kill 50% of flies 
(LC50) in 30 min was determined at 26 ± 1°C. The EO 
from Citrus sinensis was the most potent insecticide 
(LC50 = 3.9 mg/dm
3
), followed by EO from C. 
aurantium (LC50 = 4.8 mg/dm
3
).  Limonene (92.47%) 
and linalool (1.43%), were the principal components 
of C. sinensis EO.  Limonene was also the principal 
constituent (94.07%) of C. aurantium EO (Palacios et 
al., 2009a). More recently, using the same bio-assay, 
the LC50 of 9 EOs isolated from medicinal plants from 
Argentina was determined. The EO from 
Minthostachys verticillata (LC50 = 0.5 mg/dm
3
) and 
Hedeoma multiflora (LC50 = 1.3 mg/dm
3
) were the 
most potent and in both EOs the principal active 
component was identified as (4R) (+)-pulegone 
(Palacios et al., 2009b).  
The examination of the literature on the 
insecticide activity of EOs against the housefly shows 
that the principal components of the active oils are 
monoterpenoids and little is known on the insecticide 
activity of EOs in which the sesquiterpenoids are the 
principal components (Palacios et al., 2009b).  
Sesquiterpenoids are the main components of 
the essential oils of Teucrium leucocladum and 
Pogostemon cablin, both potent topical insecticides 
against M. domestica (El-Shazly and Hussein, 2004; 
Pavela, 2008). The insecticidal activity of the EO of 
Pogostemon cablin , with patchouli alcohol (42.70%), 
α-selinene (16.20%) and  β-patchoulene (12.30%) as 
principal  components has significantly higher impact 
on the mortality of  M. domestica in the topical 
application than in the fumigant application (Pavela, 
2008). The EO of Teucrium leucocladum also contains 
as principal component patchouli alcohol (31.24%), 
and with this EO mortality only in the topical 
application was recorded (El-Shazly and Hussein, 
2004).  
In the vapor phase test, the effective 
concentration of the compounds, in the exposure 
vessel needs to be sufficient to produce the toxic 
effect. In this context, the vapor pressure of the 
components of the EOs should be a fundamental 
parameter when working in short time bioassays. 
Other parameters such as lipophilicity, molecular 
weight and steric effects are not significantly 
correlated with the observed insecticidal activity of 
monoterpenes against Pediculus humanus capitis 
Yang et al., 2004).   
The insecticide activity of the essential oil of 
H. stenophyllum is due to the content of hydroxylated 
sesquiterpenes, compounds with estimated low vapor 
pressure. This fact explains that the strongest 
insecticidal effect is obtained at 2 h and not at 30 min 
(Table 2) as with monoterpenes (Palacios et al., 2009a; 
Palacios et al., 2009b). The study of mixtures of EOs 
with active monoterpenoids and sesquiterpenoids is a 
good combination to ensure insecticidal activity for a 
longer period of time in the field. 
 
ACKNOWLEDGMENTS 
Financial support for this work was provided by 
Universidad de Santiago de Chile, DICYT, 
020941UM. 
 
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Propiedades insecticidas del aceite esencial de Heliotropium stenophyllum en la mosca doméstica, Musca domestica L.

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Propiedades insecticidas del aceite esencial de Heliotropium stenophyllum en la mosca doméstica, Musca domestica L.

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