Immunopharmacology and Immunotoxicology, 2012; 34(2): 205–209

© 2012 Informa Healthcare USA, Inc.

ISSN 0892-3973 print/ISSN 1532-2513 online
DOI: 10.3109/08923973.2011.592534

RESEARCH ARTICLE

Chemical composition, antioxidant activity and larvicidal

effects of essential oil from leaves of Apium graveolens
Immunopharmacology and Immunotoxicology Downloaded from informahealthcare.com by University of Glasgow on 08/28/13

Praveen Nagella, Ateeque Ahmad, Sun-Jin Kim, and Ill-Min Chung

Department of Applied Life Science, Konkuk University, Seoul, South Korea

Abstract
The leaves of Apium graveolens were extracted and the essential oil composition, immunotoxicity effects, and
antioxidant activity were studied. The analyses were conducted by gas chromatography and mass spectroscopy
(GC-MS), which revealed the essential oils of A. graveolens leaves. Twenty-eight components, representing 73.72%
of the total oil were identified from the leaves. The major components are 4-chloro-4,4-dimethyl-3-(1-imidazolyl)-
valerophenone (19.90%), 1-dodecanol (16.55%), 9-octadecen-12-ynoic acid, methyl ester (4.93%), ethyl 4,4-D2-N-hexyl
ether (4.11%), 3-(hydroxymethyl)-1-phenyl-1-heptadecyn-3-ol (3.28%), 1,4-methano-1H-indene, octahydro-4-methyl-
8-methylene-7-(1-methylethyl)-, [1S-(1α,3αα,4α,7α,7αα)]- (2.99%), 3,4-dihydro-2H-1,5-(3ʺ-t-butyl)benzodioxepine
(2.56%), Z-10-tetradecen-1-ol acetate (2.53%), 9H-pyrrolo[3′,4′:3,4]pyrrolo[2,1-α]phthalazine-9, 11(10H)-dione,
10-ethyl-8-phenyl (2.07%). The leaf oil had significant toxic effects against the larvae of A. aegypti with an LC50 value
of 59.32 ppm and an LC90 value of 127.69 ppm. The essential oil from the A. graveolens leaves was investigated for
For personal use only.

scavenging of the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical activity and the results demonstrate that the essential
oil from the A. graveolens has potential as a natural antioxidant and thus inhibit unwanted oxidation process. The
above data indicate that the major compounds may play an important role in the toxicity of essential oils and also as
natural antioxidant.
Keywords: Aedes aegypti, Apium graveolens, antioxidant activity, 1-dodecanol, essential oils, immunotoxicity
effects

Introduction Mosquitoes are not only the most important vec-

Essential oils are natural volatile substances found in a
variety of plants. When isolated from plants, essential
oils are not usually extracted as chemically pure sub-
stances, but consist of mixtures of many compounds.
It is well-known that plant-derived natural products
are extensively used as biologically active compounds.
Among them, essential oils were the first preservatives
used by man, originally in their natural state within plant
tissues and then as oils obtained by water distillation.
Essential oils are composed by isoprenoid compounds,
mainly mono- and sesquiterpenes are the carriers of
the smell found in the aromatic plants.(1) Commercially,
the plant essential oils are used primarily in four ways:
they are used as pharmaceuticals, as flavor enhancers in
many food products, as odorants in fragrances, and as
insecticides.
tor for the transmission of malaria, filariasis, and viral
diseases,(2) but are also an important pest to humans,
causing allergic responses that include local skin reac-
tion and systemic reactions such as angioedema, and
urticaria.(3) Aedes aegypti is one of the mosquito spe-
cies responsible for the transmission of both dengue
fever and dengue hemorrhagic fever. The continuous
application of the organophosphates such as teme-
phos and fenthion and insect growth regulators such
as diflubenzuron and methoprene are generally used
for the control of mosquito larvae.(4) Although these
organophosphates are effective, their continuous use
has disrupted natural biological control systems and
has led to outbreaks of insect species, which sometimes
resulted in the widespread development of resistance,
had undesirable effects on non-target organisms and

Address for Correspondence: Ill-Min Chung, Department of Applied Life Science, Konkuk University, Seoul, 143-701, South Korea.
E-mail: imcim@konkuk.ac.kr
(Received 13 May 2011; revised 25 May 2011; accepted 26 May 2011)

205
 206 P. Nagella et al.
fostered environmental and human health concerns.(4)
These problems have highlighted the need for the
development of new strategies for selective mosquito
larval control. In the search for environmentally safe
and relatively inexpensive methods to control mos-
quitoes, plant extracts have received much interest as
potential bioactive agents against the mosquito lar-
vae. Most mosquito control programs target the larval
stage at their breeding sites with larvicides,(5) since
adulticides may reduce the adult population only
temporarily.(6) Therefore, a more efficient approach
to reduce the population of mosquitoes would be to
Immunopharmacology and Immunotoxicology Downloaded from informahealthcare.com by University of Glasgow on 08/28/13
target the larvae. In addition, discovery of the anti-
oxidant activity has been reported in various essen-
tial oils include rosemary, lavender,(7) and oregano.(8)
Consequently, antioxidant activity of essential oils
has gained considerable attention among research-
ers. Since the benefits derived from essential oils have
created renewed demand in their use by the common
public, explorations of their antioxidant activities for
their possible beneficial use in the prevention of oxi-
dative damage is in order.
Apium graveolens L., Celery, is widely grown in the
temperate zone as a garden crop, and its leaf stalks are
used as a popular vegetable. Celery can be classified
both as a seasoning and as a vegetable. For season-
ing purposes, the seeds and the plant, as well as the
For personal use only.
essential oil distilled from the seeds, are used.(9) Celery
seeds possess a characteristic aroma and pungent taste
and are used as a condiment in the flavoring of food
products. Celery seed extracts are extensively used as
flavoring ingredients in many food products, includ-
ing alcoholic and nonalcoholic beverages, frozen dairy
desserts, candy, baked goods, gelatins, puddings, meat
products, condiments and relishes, soups, gravies, snack
foods, and others. The characteristic odor of celery
essential oil is due to a series of phthalide derivatives.(10)
Sedanolide, sedanonic anhydride, 3-n-butyl phtha-
lide, and other minor phthalides are reported to be the
major constituents of celery seed oil.(11) Celery seeds
are also implicated in arthritic pain relief for treating
rheumatic conditions and gout.(10,12,13) Other reports on
the medicinal properties of celery seeds were related to
asthma and bronchitis and, when used in combination
with other herbs, to reduction of blood pressure.(12,13)
Nitrogenous compounds in celery seed essential oil
have been reported to have effects on the central ner-
vous system.(13,14) A. graveolens extracts were assessed
for their anti-inflammatory activity in intact rats by
measuring the suppression of carrageenan-induced
paw edema.(15)
The aim of this study was to investigate the chemical
composition, larvicidal properties, and antioxidant activ-
ity of the essential oil of A. graveolens leaves grown in the
Korean region. To the best of our knowledge, this is the
first report on the chemical composition, larvicidal prop-
erties, and antioxidant activity of the essential oil from
leaves of A. graveolens grown in the Korean region.
 Immunopharmacology and Immunotoxicology
Experimental
Plant material
The A. graveolens leaves were procured from local mar-
ket in October 2010 at Gwangjin-gu, Seoul, South Korea.
A voucher specimen is deposited in the Department of
Applied Life Science, Konkuk University, Seoul, South
Korea, and identified by Dr. Ill-Min Chung.
Isolation of volatile oil
The fresh leaves of A. graveolens (500 g) were subjected
to hydro-distillation in Clevenger-type apparatus for a
minimum of 5 h. The resulting essential oil was obtained
in a yield of 0.25% w/w. The oil was dried over anhydrous
sodium sulfate and then stored at 4°C until use.
Gas chromatography–mass spectroscopy analysis of
essential oil
Samples of essential oil were diluted in hexane (spec-
troscopic grade) and analyzed in a Finnigan Focus GC/
Finnigan Focus DSQ MS system (Thermo Co., Germany)
apparatus equipped with VB-WAX bonded PEG capil-
lary column (30 m × 0.25 mm internal diameter, 0.25 µm
film thickness). Helium (1 mL/min) was used as a car-
rier gas. Sample volume was injected in the split mode
10 µL (split less). The injector was kept at 150°C. The
column was maintained at 50°C for 10 min and then pro-
grammed to 200°C and held for 0.5 h at 200°C. Detector
temperature was held at 250°C. The MS was operated in
EI mode at 70 eV in the m/z range 25–350. The identifica-
tion of the compounds was performed by matching their
recorded mass spectra of the gas chromatography–mass
spectroscopy (GC-MS) data system. Quantitative data
were obtained from electronic integration peak areas
and comparing their retention time and mass spectra
library with those found in the literature and supple-
mented by the Wiley (Wiley 7th Mass Spectral Library) &
NIST MS Search 2.0 (National Institute of Standards and
Technology) GC-MS libraries.
Immunotoxicity assay
The F21 laboratory strain of A. aegypti was obtained in
2008 from the National Institute of Health, Seoul, South
Korea. Adult female mosquitoes were maintained on a
10% sucrose solution and anesthetized mice were used
for blood-feeding the mosquitoes. Larvae were reared
in plastic trays and fed a diet of chicken chow and yeast
(8:2). Mosquitoes were maintained at 27 ± 2°C, 70 ± 5%
relative humidity, and a photoperiod of 16L:8D. The
immunotoxicity activity was analyzed according to the
standard procedures recommended by the World Health
Organization.(16) The essential oil was dissolved in 1 mL
of acetone and different concentrations were prepared
(0, 12.5 25, 50, 100, and 200 ppm) using distilled water.
Twenty larvae at the fourth stage were used in the immu-
notoxicity assay and five replicates were maintained for
each concentration. The larval mortality was calculated
after 24 h of exposure. The lethal concentrations LC50 and
LC90 were calculated.
 Essential oil from leaves of Apium graveolens 207

DPPH− radical-scavenging activity of the compounds was performed by matching their

The antioxidant activity of the A. graveolens essential
oil based on the scavenging activity of the stable 1,1-di-
phenyl-2-picrylhydrazyl (DPPH−) free radical was deter-
mined by the method.(17) The different concentrations
(0, 25, 50, 100, 200, and 500 μg) of the tested samples
(0.05 mL; extracts and tocopherol) were taken in differ-
ent test tubes with 4 mL of a 0.006% MeOH solution of
DPPH−. Water (0.05 mL) in place of the oil was used as
control. Absorbance at 517 nm was determined after
30 min incubation at 37°C. Radical-scavenging activity
was expressed as the inhibition percentage and was cal-
Immunopharmacology and Immunotoxicology Downloaded from informahealthcare.com by University of Glasgow on 08/28/13
recorded mass spectra of the GC-MS data system.
Quantitative data were obtained from electronic inte-
gration peak areas and comparing their retention
time and mass spectra library with those found in the
literature and supplemented library. Other methods
of identification was by comparing their mass data
with data of library.(18,19) Twenty-eight components,
representing 73.72% of the total oil, were identi­fied
from the leaves. The major components are 4-chloro
-4,4-dimethyl-3-(1-imidazolyl)-valerophenone
(19.90%), 1-dodecanol (16.55%), 9-octadecen-12-

culated using the following formula: ynoic acid, methyl ester (4.93%), ethyl 4,4-D2-N-
hexyl ether (4.11%), 3-(hydroxymethyl)-1-phenyl-1-
Percentage radical - scavenging
= [( A0 − A1 )/A0 ] × 100 heptadecyn-3-ol (3.28%), 1,4-methano-1H-indene,
activity octahydro-4-methyl-8-methylene-7-(1-methylethyl)-,
[1S-(1α,3αα,4α,7α,7αα)]- (2.99%), 3,4-dihydro-2H-1,5-
where A0 is the absorbance of the control and A1 is the
(3ʺ-t-butyl)benzodioxepine (2.56%), Z-10-tetradecen-
absorbance of the extract/standard.
1-ol acetate (2.53%), 9H-pyrrolo[3′,4′:3,4]pyrrolo[2,1-α]
phthalazine-9, 11(10H)-dione, 10-ethyl-8-phenyl
Results (2.07%). Table 1 summarizes the current composition
on the analysis of the volatile oils from A. graveolens
Chemical constituents of the essential oil from leaves leaves. The immunotoxicity effects of the essential oils
The leaves of A. graveolens were hydro-distilled and from the leaves of celery were studied. The leaf oil had
obtained the oil percentage of 0.25. The identification significant toxic effects against the larvae of A. aegypti
For personal use only.

Table 1. Essential oil constituents from leaves of Apium graveolens.

S. No. RT Components Peak area (%)
1 8.63 9-Octadecen-12-ynoic acid, methyl ester 4.93
2 10.91 1-Butanol, 4-butoxy- 1.47
3 13.84 Ethyl 4,4-D2-N-hexyl ether 4.11
4 24.36 9H-pyrrolo[3′,4′:3,4]pyrrolo[2,1-α]phthalazine-9, 11(10H)-dione, 10-ethyl-8-phenyl 2.07
5 28.42 Acetic acid, mercapto-, 1,2-ethanediyl ester 1.19
6 32.78 1,4-Methano-1H-indene, octahydro-4-methyl-8-methylene-7-(1-methylethyl)-, 2.99
[1S-(1α,3αα,4α,7α,7αα)]-
7 35.37 3-(Hydroxymethyl)-1-phenyl-1-heptadecyn-3-ol 3.28
8 39.52 Neoalloocimene 0.49
9 40.50 4-Octen-3-one 0.53
10 45.13 Androstane-11, 17-dione, 3-[(trimethylsilyl)oxy]-, 17-[O-(phenylmethyl)oxime], (3α,5α)- 0.58
11 48.06 4′-Chloro-4,4-dimethyl-3-(1-imidazolyl)-valerophenone 19.90
12 54.24 1-Dodecanol 16.55
13 55.38 Dodecyl acrylate 1.12
14 56.84 10-Methyl-E-11-tridecen-1-ol propionate 0.55
15 58.73 2-Isononenal 1.45
16 66.26 Z-10-Tetradecen-1-ol acetate 2.53
17 70.19 3,4-Dihydro-2H-1,5-(3ʺ-t-butyl)benzodioxepine 2.56
18 76.44 Carbamic acid, N-(3-methylphenyl)-, 2-methylphenyl ester 0.64
19 79.46 Butanoic acid, heptafluoro- 0.60
20 80.61 Uridine, 5,6-dihydro- 0.86
21 82.06 Octaethylene glycol monododecyl ether 1.05
22 84.08 Phen-1,4-diol, 2,3-dimethyl-5-trifluoromethyl- 1.08
23 90.21 Butanoic acid, heptafluoro-, methyl ester 0.99
24 91.03 Hexaethylene glycol monododecyl ether 0.27
25 91.24 15-Crown-5 0.55
26 91.44 1,4,7,10,13,16-Hexaoxacyclooctadecane 0.23
27 98.48 18,18′-Bi-1,4,7,10,13,16-hexaoxacyclononadecane 0.53
28 98.78 2-Amino-4-hydroxypteridine-6-carboxylic acid 0.62

© 2012 Informa Healthcare USA, Inc.

 208 P. Nagella et al.
with an LC50 value of 59.32 ppm and an LC90 value of
127.69 ppm. The oil from the leaves of A. graveolens
exhibited a concentration-dependent immunotoxicity
activity. At the concentration of 12.5 ppm, the mortal-
ity rate was 8.0% and reached the maximum of 98.0%
mortality at the concentration of 200 ppm (Table 2).
The control substance caused no mortality for the
larvae. Also, geranial (≥95.0%), citronellol (≥95.0%),
and β-gurjunene (≥97.0%) were tested against the
F21 laboratory strain of A. aegypti. The current celery
leaves essential oil was tested for the first time against
A. aegypti.
Immunopharmacology and Immunotoxicology Downloaded from informahealthcare.com by University of Glasgow on 08/28/13
The free radical-scavenging activity of the essential
oil was tested through DPPH− method(17) and the results
were compared with tocopherol. DPPH is usually used
as a substrate to evaluate antioxidative activity of anti-
oxidants. The oil was able to reduce the stable radi-
cal DPPH− to the yellow-colored DPPH. The essential
oil exhibited a concentration-dependent antiradical
activity by inhibiting DPPH− radical. The essential oil
concentration of 500 μg exhibited good free radical-
scavenging activities, that is, above 90%. The DPPH
activity of tocopherol showed higher degree of free
radical-scavenging activity than that of the extracts at
each concentration points.
For personal use only.
Discussion
In general, plant essential oils have been recognized
as an important natural source for insecticides.(20,21)
The differences in the toxicity of essential oils against
different mosquito species are well-known(22) and are
due to qualitative and quantitative variations of the
components. Recently, the clinical use of essential
oils has expanded worldwide also including therapy
against various kinds of inflammatory diseases, such
as allergy, immunotoxicity, rheumatism, and arthritis.
These activities have mainly been recognized through
clinical experience, but there have been relatively little
scientific studies on biological actions of these natu-
ral essential oil extracts. For instance, Lee and Moon
described immunotoxicity activity of 2,6,10,15-tetrame
heptadecane from the essential oils of Clerodendron
trichotomum Thunb. against A. aegypti. The chemi-
cal components in oil extracted from the leaves of
C. trichotomum after identification of the chemical
constituents with the help of GC, GC-MS are recently
Table 2. Larvicidal activity of the essential oil from leaves of
Apium graveolens against Aedes aegypti.
Concentration Percentage of
(ppm) mortality ± SE LC50 (ppm) LC90 (ppm)
12.5 8.0 ± 1.8 59.32 127.69
25.0 22.0 ± 3.6
50.0 46.0 ± 2.4
100.0 78.0 ± 3.2
200.0 98.0 ± 2.6
 Immunopharmacology and Immunotoxicology
reported.(23) Chung et al. reported that Allium vic-
torialis L. var. platyphyllum growing in the South
Korea contained allyl methyl disulfide (24.36%), dim-
ethyl trisulfide (11.78%), allyl cis-1-propenyl disulfide
(9.17%), allyl methyl trisulfide (4.13%), and dipropyl
trisulfide (7.22%) as major components and the essen-
tial oils from the A. victorialis L. var. platyphyllum
showed good immunotoxicity activity.(24) Park et al.
described composition and immunotoxicity activity of
the major essential oil of Angelica purpuraefolia Chung
against A. aegypti.(25)
The free radical-scavenging activity of the essential
oil was tested through DPPH− method.(17) DPPH is usu-
ally used as a substrate to evaluate antioxidative activity
of antioxidants. The method is based on the reduction
of methanolic DPPH− solution in the presence of a
hydrogen-donating antioxidant, due to the formation
of the non-radical form DPPH-H by the reaction. The
oil was able to reduce the stable radical DPPH− to the
yellow-colored DPPH. It has been found that cysteine,
glutathione, ascorbic acid, tocopherol, polyhydroxy aro-
matic compounds (e.g. hydroquinone, pyrogallol, gallic
acid), and aromatic amines (e.g. p-phenylene diamine,
p-aminophenol) reduce and decolorize DPPH by their
hydrogen-donating ability.(26) In this study, essential
oil from A. graveolens leaves also showed a remarkable
antioxidant activity, one of the possible mechanisms
is polyphenolic-associated compounds (formation of
non-extractable complex between high-molecular-
weight phenolics and polysaccharides). Those kinds
of phenolic compounds show antioxidant activity due
to their redox properties, which play an important role
in absorbing and neutralizing free radicals, quenching
singlet and triple oxygen or decomposing peroxide.
The essential oil exhibited a concentration-dependent
antiradical activity by inhibiting DPPH− radical, the
activity increased with increasing concentration. The
essential oil concentration of 500 µg exhibited good free
radical-scavenging activities, that is, above 90%. The
higher concentration of essential oil from thyme species
exhibited highest antioxidant activity.(27) The findings of
the present study also indicate that the essential oils
extracted from the leaves of A. graveolens could be used
as a potential natural immunotoxicity effects and also
as antioxidant activity.
Acknowledgement
The author Praveen Nagella is recipient of the Konkuk
University Brain Pool Postdoctoral Program, Konkuk
University, Seoul, South Korea.
Declaration of interest
The authors report no conflicts of interest. The authors
alone are responsible for the content and writing of the
article.

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