Composições de Óleos Essenciais de Zanthoxylum piperitum e Zanthoxylum schinifolium

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Journal of Essential Oil Bearing Plants
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Insecticidal Toxicities and Essential Oil
Compositions of Zanthoxylum piperitum and
Zanthoxylum schinifolium Fruits in Korea
Hoi-Seon Lee
To cite this article: Hoi-Seon Lee (2016) Insecticidal Toxicities and Essential Oil Compositions of
Zanthoxylum piperitum and Zanthoxylum schinifolium Fruits in Korea, Journal of Essential Oil
Bearing Plants, 19:8, 2065-2071, DOI: 10.1080/0972060X.2016.1249415
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Insecticidal Toxicities and Essential Oil Compositions of
Zanthoxylum piperitum and Zanthoxylum schinifolium Fruits in Korea
Hoi-Seon Lee *
Department of Bioenvironmental Chemistry, College of Agriculture and Life
Sciences, Chonbuk National University, Jeonju 54896, South Korea
Abstract: The compounds in the essential oils extracted from Zanthoxylum schinifolium and Z. piperitum
fruits were analyzed by GC-MS and tested to identify acaricidal activities against Dermatophagoides farinae,
D. pteronyssinus, and Tyrophagus putrescentiae. The major compounds in Z. schinifolium were found to be
estragole (75.03 %), 4-methoxybenzaldehyde (4.60 %), 2-undecanone (2.86 %), nonanal (0.97 %), 2-nonanone
(0.80 %), 3-methoxycinnamaldehyde (0.79 %), and α-caryophyllene (0.72 %). In the essential oil of Z. piperitum,
the main constituents were shown to be isocarvestrene (28.97 %), geranyl acetate (22.68 %), (+)-citronellal
(14.90 %), citronellyl acetate (9.54 %), 4-isopropyl-2-cyclohexenone (5.46 %), myrcene (2.11 %), and citronellol
(1.79 %). The Z. schinifolium oil exhibited acaricidal toxicities against D. farinae, D. pteronyssinus, and T.
putrescentiae, with LD50 values of 14.63, 15.36, and 15.67 μg/cm3, respectively, and the LD50 values of the Z.
piperitum oil against three mite species were 4.19, 4.94, and 5.46 μg/cm3, respectively. Based on the LD50
values, the acaricidal toxicities of the Z. schinifolium oil were circa 2.51, 2.23, and 1.94 times more effective
than that of DEET (36.74, 34.25, and 30.43 μg/cm2), respectively. The results show that Z. piperitum and Z.
schinifolium oils have the potential to be an alternative material to control mites.
Key words: Acaricidal activity, Dermatophagoides farinae, essential oil, Zanthoxylum
piperitum, Zanthoxylum schinifolium.
Introduction
The European house dust mite, Dermato-
phagoides pteronyssinus (Trouessart), and the
American house dust mite, D. farinae (Hughes),
are the important house dust mites because of their
cosmopolitan occurrence in the home 1. They are
a major source of allergens associated with pe-
rennial rhinitis and asthma 1. The most signifi-
cant stored food mite is Tyrophagus putrescentiae
due to its abundance in the grains and foods 1.
The stored food mite is an etiological agent of
allergic reactions among farmers handing con-
taminated the stored grains and foods 1-3. House
dust mites and stored food mites have been imple-
mented through use of synthetic acaricides such
as avermectines and DEET 1-3. However, the re-
peated use of avermectines and DEET has resulted
in the undesirable effects on non-target organisms
and resistance 1-3. For this reason, plant oils have
been evaluated for their acaricidal activity in the
hope of replacing commercial acaricides 1-3. The
major constituents of plant oils have been pro-
posed as promising alternative sources to chemi-
cal acaricides and insecticides 1-5.
The Rutaceae family contains a rich source of
monoterpenes 6, and are mainly tropical, consist-
ing of roughly 150 genera and 1800 species 7.
Among these, the Zanthoxylum genus has over
200 species 6. Zanthoxylum schinifolium (Sancho)
and Z. piperitum (Chopi) have been used as a
ISSN Print: 0972-060X
ISSN Online: 0976-5026
*Corresponding author (Hoi-Seon Lee)
E-mail: < hoiseon@jbnu.ac.kr > © 2016, Har Krishan Bhalla & Sons
Received 09 March 2016; accepted in revised form 12 October 2016
TEOP 19 (8) 2016 pp 2065 - 2071 2065
favorite spice and as an aromatic medicinal in-
gredient in Japan, Korea, and the rest of East Asia
7-10. Since ancient times, these plants have been
utilized as folk remedies for the treatment of
ulcers, neurological and stomach problems 10.
According to previous studies regarding Z.
schinifolium and Z. piperitum oils, there are some
reports of antibacterial, antifungal, and anti-
inflammatory activities 8,11-13. However, few stud-
ies relating to the acaricidal toxicity of Z. schini-
folium and Z. piperitum oils has been reported.
Therefore, our study was to measure the compari-
son of the oil composition and acaricidal toxici-
ties of Z. schinifolium and Z. piperitum fruits
against house dust mites and stored food mites to
assess the possibility for use as alternative
acaricides.
Materials and methods
Essential oils
The dried fruits of Z. schinifolium and Z. piperi-
tum were purchased from the local market in
Jecheon, South Korea, in December 2014. A
voucher specimen was authenticated by Dr.
Jeongmoon Kim and deposited at Department of
Landscape Architecture, Chonbuk National Uni-
versity. Each fruits (150 g) were ground and
treated using a Clevenger-type apparatus to ob-
tain the essential oil of Z. schinifolium and Z.
piperitum fruits by hydrodistillation for 6 h. The
extracted oils of Z. schinifolium and Z. piperitum
fruits were decanted, dried over Na2SO4, and con-
centrated in vacuo by rotary evaporator (EYELA,
NAJ-100, Tokyo, Japan) at 30°C. The collected
oils were subsequently stored at 4°C.
Gas chromatography-Mass spectrometry (GC-
MS)
The essential oils of the Z. schinifolium and Z.
piperitum fruits were analyzed using GC-MS (HP-
6890/5973IV, Hewlett Packard, USA). A DB-5
(50°C, 0.25 μm film thickness)-fused silica cap-
illary column (30 m x 0.25 mm) was used. The
conditions were as follows: carrier gas; helium,
split injection; 0.8 ml/min, injector temperature;
211°C, sample temperature; 2°C/min up to 201°C
(20°C hold for 15 min), MS Ion Source; EI 70
eV, Ion source temperature; 200°C, and mass
range; 50-600 amu. Percentages of individual
volatile contents were determined by peak area,
using correction factors.
The compounds in the essential oils were iden-
tified by comparing the retention indices, GC
retention times, and MS spectra reported in the
library (Wiley Registry 8 edition).
Test mites
The respective cultures of house dust mites
(pyroglyphidae; D. farinae and D. pteronyssinus)
and stored food mites (Acaridae; T. putrescentiae)
had been maintained in an incubator for 13 years
at 27±1°C and 75-90 % relative humidity, with-
out exposure to light or acaricides. Mites were
provided with a mixture of ground fry feed and
dried yeast (20:1 weight). The fry feed (No.1) con-
sisted of crude protein (43.9 %), phosphate (18.1
%), cellulose (4.9 %), crude lipid (4.1 %), cal-
cium (2.1 %), and other components (26.9 %).
Fumigant and contact toxicity methods
The fumigant activities of the essential oils were
tested as previously explained by Song et al 2.
The susceptibility of the three mite species to two
essential oils was evaluated in the fumigant tox-
icity method. Different concentrations (80, 60, 40,
20, 10, 5.0, and 2.5 μg/cm2) of each oil dissolved
in 10 μl acetone (carrier solvent) were injected
onto white cotton fabric discs (8 mm-diameter, 1
mm-thickness). After drying (27°C) for 15 min
in the fume hood, distilled water (5 μl)was added.
Individual mites (30-40 mites) of each species
were placed in microfuge tubes (10 ml) contain-
ing the fabric discs treated with essential oils and
distilled water.
The contact toxicity method was tested as pre-
viously explained by Song et al 2 to evaluate the
acaricidal toxicity of the essential oils. Different
concentrations (80, 60, 50, 40, 20, 10, 5.0, and
2.5 μg/cm2) of each oil dissolved in 50 μl metha-
nol were injected onto filter paper discs (5 cm
diameter, 55 μm thick). Next, the discs were dried
(27°C) in fume hood for 15 min and placed sepa-
rately onto the bottom of Petri dishes (5 cm di-
ameter × 0.8 cm deep), after which, batches of
30-40 adult mites were added. The Petri dishes
were covered and sealed with Parafilm®. The
Hoi-Seon Lee / TEOP 19 (8) 2016 2065 - 2071 2066
mortality rate of the adult mites in the fumigant
and contact toxicity methods was determined fol-
lowing treatment with the essential oils for 24 h,
through inspection under a binocular microscope
(20 ×). All treatments were replicated five times.
The negative controls received only solvent in
fumigant method (acetone) and contact method
(methanol), and DEET was used as a positive
control. LD50 values were calculated by probit
analysis. The Scheffe’s test at p=0.05 was used to
compare and separate the treatment means (SAS
Institute) 14. Relative toxicity (RT) was determined
as the ratio of LD50 of DEET/LD50 of each oil, as
described previously.
Results and discussion
The yield of the essential oil extracted for the
dried fruits of Z. schinifolium and Z. piperitum is
0.48 and 0.59 %, respectively. The essential oils
of Z. schinifolium and Z. piperitum fruits were
analyzed by GC-MS. The identified components
of the essential oil of Z. schinifolium are shown
in detail (Table 1). The compounds analyzed in
Z. schinifolium oil were estragole (75.03 %), 4-
methoxybenzaldehyde (4.60 %), 2-undecanone
(2.86 %), nonanal (0.97 %), 2-nonanone (0.80 %),
3-methoxycinnamaldehyde (0.79 %), α-caryo-
phyllene (0.72 %), octanal (0.68 %), β-
caryophyllene (0.56 %), 2-undecenal (0.53 %),
(-)-β-elemene (0.45 %) and linalool (0.37 %). The
volatile compounds consisted of 4 aldehydes
(octanal, nonanal, 4-methoxybenzaldehyde, and
3-methoxycinnamaldehyde), 1 monoterpene ether
(estragole), 1 ketone (2-nonanone), 1 monoter-
Table 1. GC-MS analysis of the essential oil of the Z. schinifolium fruits
No. Compound RT* RI** Methods of Amount
Identification (%)
1 Octanal 6.225 1005 RI, MS*** 0.68
2 2-Nonanone 7.882 1052 RI, MS 0.83
3 Linalool 8.040 1082 RI, MS 0.37
4 Nonanal 8.113 1104 RI, MS 0.97
5 Estragole 9.873 1172 RI, MS 75.03
6 4-Methoxybenzaldehyde 10.763 1257 RI, MS 4.60
7 2-Undecanone 11.280 1251 RI, MS 2.86
8 2-Undecenal 12.352 1311 RI, MS 0.53
9 (-)-â-Elemene 12.899 1398 RI, MS 0.45
10 β-Caryophyllene 13.378 1494 RI, MS 0.56
11 α-Caryophyllene 13.857 1579 RI, MS 0.72
12 3-Methoxycinnamaldehyde 15.266 1378 RI, MS 0.79
Major Grouped Compounds
Aldehydes 7.04
Ketones 0.83
Monoterpene alcohols 0.37
Monoterpene aldehydes 0.53
Monoterpene ethers 75.03
Monoterpene ketones 2.86
Sesquiterpene hydrocarbons 1.73
Total 88.39
*RT: Retention time (in minutes)
**RI: The retention indices in elution order from the DB-5 column.
***MS: Mass spectra
Hoi-Seon Lee / TEOP 19 (8) 2016 2065 - 2071 2067
pene alcohol (linalool), 1 monoterpene aldehyde
(2-undecenal), 1 monoterpene ketone (2-
undecanone), and 3 sesquiterpene hydrocarbons
((-)-β-Elemene, β-caryophyllene and α-caryo-
phyllene).
The chemical composition of the essential oil
of Z. piperitum fruits is described in detail (Table
2). The components of the essential oil acquired
from Z. piperitum fruits were isocarvestrene
(28.97 %), geranyl acetate (22.68 %), (+)-citronel-
lal (14.90 %), citronellyl acetate (9.54 %), 4-iso-
propyl-2-cyclohexenone (5.46 %), myrcene (2.11
%), citronellol (1.79 %), cyclohexanol (0.92 %),
methyl heptadienone (0.76 %), terpinolene (0.66
%), cuminaldehyde (0.66 %), and piperitone (0.67
%). The essential oil consisted of 2 ketones (me-
thyl heptadienone and 4-isopropyl-2-cyclo-
hexenone), 2 monoterpene alcohols (cyclohexanol
and citronellol), 2 monoterpene aldehydes ((+)-
citronellal and cuminaldehyde), 2 monoterpene
esters (citronellyl acetate and geranyl acetate), 3
monoterpene hydrocarbons (myrcene, iso-
carvestrene, and terpinolene) and 1 monoterpene
ketone (piperitone). When comparing the data of
two essential oils, the results of the GC-MS analy-
sis show a different composition, despite their
source plants being from the same family and
genus. In a previous study, Seo et al 15 reported
that the main compounds in Z. schinifolium oil
were estragole (63.91 %) and octanoic acid (3.90
%), and Jiang and Kubota 21 showed that the ma-
jor components of the essential oil from Z. piperi-
tum fruits were limonene (29.54 %) and β-phellan-
drene (17.79 %). It can be said, therefore, that the
compounds present in the essential oils are influ-
enced by the harvest season, degree of fruit ma-
Table 2. GC-MS analysis of the essential oil of the Z. piperitum fruits
No. Compound RT* RI** Methods of Amount
Identification (%)
1 Methyl heptadienone 9.230 946 RI, MS 0.76
2 Myrcene 5.891 958 RI, MS*** 2.11
3 Isocarvestrene 6.681 1018 RI, MS 28.97
4 4-Isopropyl-2-cyclohexenone 9.537 1069 RI, MS 5.46
5 (+)-Citronellal 8.886 1125 RI, MS 14.90
6 Piperitone 10.636 1158 RI, MS 0.67
7 Citronellol 10.117 1179 RI, MS 1.79
8 Cuminaldehyde 10.408 1230 RI, MS 0.66
9 Terpinolene 7.909 1287 RI, MS 0.66
10 Citronellyl acetate 12.038 1302 RI, MS 9.54
11 Geranyl acetate 12.498 1352 RI, MS 22.68
12 Cyclohexanol 8.801 1357 RI, MS 0.92
Major Grouped Compounds
Ketones 6.22
Monoterpene alcohols 2.71
Monoterpene aldehydes 15.56
Monoterpene esters 32.22
Monoterpene hydrocarbons 31.74
Monoterpene ketones 0.67
Total 89.39
*RT: Retention time (in minutes)
**RI: The retention indices in elution order from the DB-5 column.
***MS: Mass spectra
Hoi-Seon Lee / TEOP 19 (8) 2016 2065 - 2071 2068
turity, and plant parts (fruits and leaves) 16,17.
The acaricidal toxicities of the essential oils of
Z. piperitum and Z. schinifolium fruits belonging
to the Rutaceae family were examined and com-
pared with DEET, which is used as a synthetic
acaricide, against D. farinae, D. pteronyssinus,
and T. putrescentiae, as presented in Table 3. The
essential oil of Z. schinifolium fruits exhibited
fumigant toxicity against D. farinae, D. pteronys-
sinus, and T. putrescentiae, with LD50 values of
14.63, 15.36, and 15.67 μg/cm3, respectively.
Based on the LD50 values, the acaricidal activity
of Z. schinifolium oil was circa 2.51, 2.23, and
1.94 times more effective than that of DEET
(36.74, 34.25, and 30.43 μg/cm3), respectively.
The LD50 values of Z. piperitum oil against the
three mite species, determined using the fumigant
toxicity method, were 4.19, 4.94, and 5.46 μg/
cm3, which is circa 8.77, 6.93, and 5.57 times
higher toxic than the LD50 values of DEET. With
respect to the contact toxicity method, the LD50
values of Z. schinifolium oil against D. farinae,
D. pteronyssinus, and T. putrescentiae were 33.88,
34.50, and 36.53 μg/cm2, respectively. The LD50
values of Z. piperitum oil were 9.26, 10.78, and
12.91 μg/cm2 against D. farinae, D. pteronyssinus,
and T. putrescentiae, respectively. On the basis
of these LD50 values, Z. piperitum oil against the
three selected species of mites was 2.24, 1.15, and
1.10 times more toxic than DEET (20.73, 12.39,
and 14.21 μg/cm2), respectively. In these studies,
Dermatophagoides spp. was more susceptible to
Z. schinifolium and Z. piperitum oils than Tyro-
phagus putrescentiae regardless of methods. It
indicated that the acaricidal effect of plant-derived
oils could be influenced by the mite species 3.
As judged by the LD50 values against house dust
mitesand stored food mites, the toxicity of Z.
piperitum oil was circa 3.50, 3.10, and 2.90 times
higher than that of Z. schinifolium oil, with the
fumigant toxicity method. With the exposure
method, Z. piperitum oil was 3.7, 3.2, and 2.8
Table 3. Acaricidal activities of Z. schinifolium and Z. piperitum oils against
three mite species, using fumigant toxicity and contact toxicity methods*
Samples Methods Mite species LD50 ± SE** RT***
Z. schinifolium Fumigant D. farinae 14.63 ± 1.0 2.51
D. pteronyssinus 15.36 ± 0.9 2.23
T. putrescentiae 15.67 ± 1.8 1.94
Contact D. farinae 33.88 ± 1.9 0.61
D. pteronyssinus 34.50 ± 1.2 0.36
T. putrescentiae 36.53 ± 2.6 0.39
Z. piperitum Fumigant D. farinae 4.19 ± 2.1 8.77
D. pteronyssinus 4.94 ± 1.3 6.93
T. putrescentiae 5.46 ± 0.7 5.57
Contact D. farinae 9.26 ± 2.6 2.24
D. pteronyssinus 10.78 ± 3.1 1.15
T. putrescentiae 12.91 ± 2.5 1.10
DEET Fumigant D. farinae 36.74 ± 1.2 1.00
D. pteronyssinus 34.25 ± 1.8 1.00
T. putrescentiae 30.43 ± 0.9 1.00
Contact D. farinae 20.73 ± 0.6 1.00
D. pteronyssinus 12.39 ± 1.1 1.00
T. putrescentiae 14.21 ± 1.8 1.00
*Exposed for 24 h.
**Dose expressed in μg/cm3 (fumigant) and μg/cm2 (contact): LD50
***RT: Relative toxicity = LD50 value of DEET/ LD50 value of each compound
Hoi-Seon Lee / TEOP 19 (8) 2016 2065 - 2071 2069
times more effective than Z. schinifolium oil.
These values are likely a reflection of the widely
different chemical compositions of the two essen-
tial oils. In a previous report by Kim and Ahn,
estragole, found to be the main volatile compound
in Z. schinifolium oil, was reported to exhibit in-
secticidal activities against S. oryzae, C. chinensis,
and L. serricorne 18. Nevertheless, Z. schinifolium
oil contained 75 % estragole and was recorded to
have a lower toxicity than other agents. A high
toxicity was recorded in Z. piperitum oil when
three mite species were exposed to direct contact
or vapor methods at selected concentrations. How-
ever, the main component of Z. piperitum oil,
isocarvestrene, has not yet been studied for aca-
ricidal activity, and has only been found to exist
in L. decidua oil in a previous study by Salem et
al 19. The second major component of Z. piperitum
oil, geranyl acetate, has previously been shown
to have a low acaricidal activity against T.
putrescentiae 20. Thus, we assume that the acari-
cidal toxicity of Z. piperitum oil may be a result
of citronellal and citronellyl acetate possessing
acaricidal activities against T. putrescentiae and
T. urticae 20,21.
The present study indicates that Z. piperitum
oil possesses more effective acaricidal toxicity
than Z. schinifolium oil. In this regard, Z.
piperitum oil is a potential alternative to control
mites, and moreover, this study may be the foun-
dation for the creation of novel commercial
acaricides to reduce resistance in mites caused by
the repetitive use of synthetic acaricides. In a pre-
vious study, Nogueira et al 22 indicated that the
bioacaricidal activity of the essential oil from
Zanthoxylum caribaeum leaves determined
against Rhipicephalus microplus females. Essen-
tial oil (5 %) of Z. caribaeum leaves caused 65 %
mortality on the first day after treatment, 85 % on
the second day, and 100 % mortality by the fifth
day. To our knowledge, it can be said that the aca-
ricidal toxicities against house dust mites, stored
food mites and cattle ticks might be influenced
by the essential oils of the Zanthoxylum genus.
Further studies need to be carried out in order to
confirm which the constituents in Z. piperitum
oil possess acaricidal activity, with special con-
sideration to isocarvestrene.
Acknowledgments
This work was carried out with the support of
“Cooperative Research Program for Agriculture
Science & Technology Development (Project title:
Development of crop pest management techniques
using the functional materials derived from
Coriandrum sativum and Valeriana fauriei,
Project No. PJ011983022016)” Rural Develop-
ment Administration, Republic of Korea.
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Hoi-Seon Lee / TEOP 19 (8) 2016 2065 - 2071 2071