Essential oil composition of Eucalyptus microtheca and Eucalyptus

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Original Research Article
Essential oil composition of Eucalyptus microtheca and Eucalyptus
viminalis
Malek Taher Maghsoodlou1*, Nasrin Kazemipoor2, Jafar Valizadeh3,
Mohsen Falak Nezhad Seifi1, Nahid Rahneshan1
1
Department of Chemistry, University of Sistan and Baluchestan, Zahedan, Iran
Department of Agriculture, Shiraz University, Shiraz, Iran
3
Department of Biology, University of Sistan and Baluchestan, Zahedan, Iran
2
Article history:
Received: Nov 13, 2014
Received in revised form:
Feb 7, 2015
Accepted: June 14, 2015
Vol. 5, No. 6, Nov-Dec 2015,
540-552.
* Corresponding Author:
Tel: +985418052269
Fax: +985412446565
‎[email protected]
Keywords:
Essential oil
Eucalyptus microtheca
Eucalyptus viminalis
Myrtaceae
Hydro-distillation, GC/MS
Abstract
Objective: Eucalyptus (Fam. Myrtaceae) is a medicinal plant and
various Eucalyptus species possess potent pharmacological actions
against diabetes, hepatotoxicity, and inflammation. This study
aims to investigate essential oil composition from leaves and
flowers of E. microtheca and E. viminalis leaves growing in the
Southeast of Iran.
Materials and Methods: The aerial parts of these plants were
collected from Zahedan, Sistan and Baluchestan province, Iran in
2013. After drying the plant materials in the shade, the chemical
composition of the essential oils was obtained by hydro-distillation
method using a Clevenger-type apparatus and analyzed by
GC/MS.
Results: In the essential oil of E. microtheca leaves, 101
compounds representing 100%, were identified. Among them, αphellandrene (16.487%), aromadendrene (12.773%), α-pinene
(6.752%), globulol (5.997%), ledene (5.665%), P-cymen
(5.251%), and β-pinene (5.006%) were the major constituents. In
the oil of E. microtheca flowers, 88 compounds representing
100%, were identified in which α-pinene (16.246%), O-cymen
(13.522%), β-pinene (11.082%), aromadendrene (7.444%), αphellandrene (7.006%), globulol (5.419%), and 9-octadecenamide
(5.414%) were the major components. Sixty six compounds
representing 100% were identified in the oil of E. viminalis leaves.
The major compounds were 1, 8-cineole (57.757%), α-pinene
(13.379%), limonene (5.443%), and globulol (3.054%).
Conclusion: The results showed the essential oils from the aerial
parts of Eucalyptus species are a cheap source for the commercial
isolation of α-phellandrene, α-pinene, and 1, 8-cineole compounds
to be used in medicinal and food products. Furthermore, these
plants could be an alternative source of insecticide agents.
Please cite this paper as:
Maghsoodlou MT, Kazemipoor N, Valizadeh J, Falak Nezhad Seifi M, Rahneshan N. Essential oil composition
of Eucalyptus microtheca and Eucalyptus viminalis. Avicenna J Phytomed, 2015; 5 (6): 540-552.
AJP, Vol. 5, No. 6, Nov-Dec 2015
540
Maghsoodlou et al.
Introduction
Plants and their derivatives such as
essential oils have long been used as food
flavoring, beverages, and antimicrobial
agents (Ghasemi et al., 2005). Nowadays,
developing countries pay more attention to
herbal medicines due to the noxious side
effects of synthetic medicines on patients.
In addition, the application of natural
antioxidants in food factories has attracted
a growing interest (Asghari and
Mazaheritehrani, 2010) to minimize such
oxidative damages in human body.
Therefore, research works concerning
essential oils as potential antioxidants for
treatment of human diseases and free
radical-related disorders are important.
Concomitantly, public attention to natural
antioxidants has been increased during the
last years, and it is necessary to find
natural sources of antioxidants that could
replace synthetic antioxidants or at least
reduce their use as food additives. For
these reasons, numerous researches have
been conducted in the extraction field of
biologically active compounds from the
herbs (Shahidi, 2000). Eucalyptus (Fam.
Myrtaceae) is a genus of evergreen
aromatic flowering trees, which has over
600 species (Jahan et al., 2011; Nagpal et
al., 2010). It is indigenous in Australia and
its Northern islands (Mozaffarian, 1996).
Because of their economic value, various
species of Eucalyptus are cultivated in
sub-tropical and warm temperate regions
(Sastri, 2002). Some of the Eucalyptus
species are used for feverish conditions
(malaria, typhoid, and cholera) and skin
problems such as burns, ulcers, and
wounds (Reynolds and Prasad, 1982).
Eucalyptus species contain volatile oils
that are most plentiful in the plant leaves
(Pearson, 1993). Anticancer, antifungal,
anti-inflammatory (Sadlon and Lamson,
2010),
and
antioxidant
properties
(Grassmann et al., 2000) have been
attributed to the leaf extracts of this plant.
For this reason, the importance of these
plants as an herbal medicine, the aim of
the present study was to investigate the
chemical composition of the essential oil
from leaves and flowers of Eucalyptus
microtheca and E. viminalis leaves from
Zahedan (with latitude of 29° 29ˊ N and
longitude of 60° 51ˊ E and 1352 m above
sea level in summer of 2013) in Sistan and
Baluchestan province, Iran as an important
geographical zone for medicinal plants.
Material and Methods
Plant materials
Eucalyptus microtheca and E. viminalis
were collected in June, 2013 from
Zahedan in Sistan and Baluchestan
province (GPS coordinates: 60.8628,
29.4964), Iran during the flowering stage.
The taxonomic identification of each plant
was confirmed by Professor V.
Mozaffarian, Research Institute of Forests
and Ragelands, Tehran, Iran. The voucher
specimens were deposited in the national
herbarium of Iran (TARI). Collected plant
materials were separated with a meticulous
care and dried in the shade to avoid extra
damaging
and
minimizing
crosscontamination of the plant leaves.
Isolation of the essential oil
The leaves and flowers of E.
microtheca and E. viminalis leaves were
dried and milled into a fine powder. The
volatile oils were isolated by hydrodistillation method using a Clevenger-type
apparatus. For the extraction, 50 g of the
cleaned, air-dried and powdered of leave
samples of E. microtheca and E. viminalis
were hydro-distilled with 500 mL water in
a Clevenger-type apparatus for 4 h.
Moreover, 30 g of the E. microtheca
flower samples were hydro-distilled with
300 mL water for 4 h. The oils were dried
over anhydrous Na2SO4 (Merck), stored in
a dark glass bottle and kept at -8 °C until
analysis.
AJP, Vol. 5, No. 6, Nov-Dec 2015
541
Essential oil composition of Eucalyptus microtheca and Eucalyptus viminalis
retention indices with those of standards.
The results were also confirmed by
comparing their mass spectra with the published mass spectra or Wiley library.
Essential oil analysis
The essential oils were analyzed on an
Agilent
6890
gas
chromatograph
interfaced to an Agilent 5973 N mass
selective detector (Agilent Technologies,
Palo Alto, USA). A fused silica capillary
column (30 m length × 0.025 mm internal
diameter × 0.25 μm film thickness; HP-1;
silica
capillary
column,
Agilent
Technologies) was used. The data were
acquired under the following conditions:
The oven temperature increased from 40
°C to 250 °C at a rate of 3 °C/min.
The temperatures of injector and
detector also were 250 °C and 230 °C,
respectively. The carrier gas was helium
(99.999%) with a flow rate of 1 ml/min
and the split ratio was 50 ml/min. For GC–
MS detection, an electron ionization
system with ionization energy of 70 eV
was used. The retention indices were
calculated for all volatile constituents
using retention time of n-alkanes (C8-C22)
which were injected at the same
chromatographic conditions. The components were identified by comparing
Results
The oils were isolated by hydrodistillation and analyzed by capillary gas
chromatography, using flame ionization
and mass spectrometric detection. The
obtained results of the identified
compounds in the essential oil of leaves
and flowers of E. microtheca and E.
viminalis leaves with their percentage,
retention index (RI), and retention time
(tR) are shown in Tables 1, 2, and 3,
respectively.
The
chromatographic
analysis of extracted volatile oil of E.
microtheca leaves revealed the presence of
sesquiterpenes (47.852%), monoterpenes
(46.844%), polyketides and fatty acids
(3.496%), diterpene (0.140%), alkanes
(0.085%), aromatic compounds (0.029%),
and other compounds (1.521%).
Table 1. Composition of the volatile oil of Eucalyptus microtheca leaves.
No.
1
Compound
%1
RI2
RT3 (min)
1
α –thujene
0.742
742
9.381
2
α -pinene
6.752
767
9.716
3
comphene
0.079
792
10.063
4
β - pinene
5.006
817
11.33
5
β -myrcene
0.533
850
12.025
6
α -phellandrene
16.487
871
12.755
7
α -terpinene
0.832
892
13.103
8
p- cymene
5.251
913
13.374
9
β -phellandrene
2.194
934
13.626
10
Limonene
1.503
955
13.722
11
Cis-ocimene
1.655
976
14.144
12
β –ocimene Y
0.101
997
14.546
13
γ -terpinene
1.235
1018
14.976
14
15
Cymene
α -terpinolene
0.024
0.425
1038
1054
16.021
16.267
16
17
Rosefuran
Cycloheptanmethanol
0.024
0.061
1073
1092
16.499
16.581
18
Linalool L
0.093
1112
16.806
Compound percentage
2
Retention index
3
Retention time
AJP, Vol. 5, No. 6, Nov-Dec 2015
542
Maghsoodlou et al.
Continued table 1.
1
%1
RI2
RT3 (min)
Isoamyl isovalerate
0.529
1131
17.038
Isoamyl valerate
0.056
1151
17.152
21
Fenchol
0.076
1170
17.222
22
Trans-pinene hydrate
0.062
1190
17.598
23
Allocimene
0.049
1209
18.247
24
1-terpineol
0.045
1229
18.412
25
1-methylnorcarane
0.051
1267
19.229
26
Ethylbenzoate
0.124
1287
19.367
27
4-terpineol
1.256
1326
20.172
28
1-(adamantly) cyclohexene
0.042
1345
20.311
29
β -fenchol
0.203
1384
20.695
30
cis-sabinol
0.224
1404
21.183
31
Thiophene, 2-ethyl-5-methyl
0.120
1428
21.729
32
Ascaridole
0.085
1448
21.866
33
Dicyclobutylidene oxide
0.084
1527
24.404
34
35
Divinyldimethylsilane
Piperitone
0.114
0.196
1507
1487
23.545
22.992
36
1-methoxyhept-1-yne
1.809
1467
22.838
37
Citronellyl formate
0.029
1546
24.67
38
Carvacrol
0.420
1625
26.426
39
α –cubebene
0.160
1927
28.309
40
Isoledene
0.278
1957
29.297
41
Copaene
0.308
1987
29.387
42
2-pentene-1-ol, 2-methyl
0.215
1713
30.103
43
α –gurjunene
1.897
1762
30.826
44
Trans-caryophyllene
0.539
1779
31.059
45
Aromadendrene
12.773
1811
32.17
46
Epizonaren
0.067
1828
32.30
47
α –humulene
0.142
1844
32.435
48
Alloarmadendrene
2.520
1861
32.798
49
γ –gurjunene
0.327
1877
33.178
50
α –copaene
0.755
1893
33.39
51
β –selinene
0.525
1910
33.692
52
β –panasinsene
0.702
1926
33.862
53
Ledene
5.665
1943
34.303
54
α –muurolene
0.398
1959
34.357
55
Geremacrene B
0.099
1975
34.563
56
α –amorphene
1.666
1992
34.862
57
cis-calamenene
0.207
2008
34.944
58
δ -cadinene
2.663
2025
35.284
59
Cadina-1, 4-diene
0.103
2041
35.514
60
α –calacorene
0.087
2058
35.626
61
α –cadinene
0.163
2074
35.727
62
Ledane
0.092
2639
36.062
63
Epiglobulol
1.167
2668
36.509
64
β –maaliene
0.306
2698
36.612
65
Palustrol
0.190
2727
36.751
66
Spathlenol
1.915
2757
37.076
No.
Compound
19
20
Compound percentage
2
Retention index
3
Retention time
AJP, Vol. 5, No. 6, Nov-Dec 2015
543
Essential oil composition of Eucalyptus microtheca and Eucalyptus viminalis
Continued table 1.
No.
67
68
69
70
71
72
73
74
75
76
77
78
79
80
81
82
83
84
85
86
87
88
89
90
91
92
93
94
95
96
97
98
99
100
101
1
Compound
Globulol
Veridiflorol
1, 3-dimethyl-5-ethyladamantane
Ledol
γ- curcumene
Isospathulenol
Tau-muurolol
δ -cadinol
Guaia-3, 9-diene
α– cadinol
Vulgarol A
Hexadecanoic acid
2-tridecanol
Hexadecanoic acid ethyl ester
Decyltetraglycol
Tricosane
Benzonitrile, m-phenethyl
Pentacosane
Pentaethoxylated pentadecyl
alcohol
1-cyclohexene-1-carboxaldehyde,
4-(1-methylethyl)
Cyclohexene, 3-methyl-6-(1methylethyl)
2- cyclohexene-1-ol, 2-methyl-5-(1methylethenyl)-, trans2, 3-dimethyl-cyclohexa-1, 3-diene
α –campholonic acid
Furan, 2, 3-dihydro-4-(1methylpropyl)
(E)-3-isopropyl-6-oxo-2-heptenal
1, 5, 5-trimethyl-6-methylenecyclohexene
2, 6, 10-trimethyl-2, 5:7, 10dioxido- dodeca-3, 11-diene-5-ol
Tricyclo [6.3.0.1(2, 3)] undec-7ene, 6, 10, 11, 11-tetramethyl
1-methyl-4-isopropyl-cis-3hydroxycyclohex-1-ene-6-one
1H-cyclopropa[a]naphthalene,
decahydro- 1,1,3
a-trimethyl-7-methylene-,
[1as(1a.1alpha.,3a.alpha.,7a.beta.,7
b.alpha.)]
Naphthalene, 1, 2, 3, 4, 4a, 7hexahydro-1, 6- dimethyl-4-(1methylethyl)
Bicyclo[3.1.0]hex-2-ene,2-methyl5- (1-methylethyl)
(+)-(1R, 2S, 4R, 7R)-7-isopropyl-5methyl-5- bicycle [2.2.2] octen-2-ol
1, 6-dimethyl-2-cyano-3-ethyl-3piperidine
Compound percentage
2
Retention index
%1
RI2
5.997
1.243
0.285
0.753
0.391
0.300
1.580
0.231
0.292
0.806
0.129
0.093
0.028
0.025
0.025
0.012
0.032
0.073
0.036
2786
2816
2845
2875
2963
2992
2509
2529
2548
2568
2587
2886
2909
2932
2955
2979
-
RT3 (min)
37.554
37.74
37.80
38.036
38.965
39.259
39.495
39.562
39.767
39.908
40.375
51.074
51.382
51.755
59.356
61.218
0.046
-
0.170
-
-
0.108
-
-
0.059
-
-
0.390
0.049
0.458
-
-
0.058
0.056
-
-
0.268
-
-
0.138
-
-
0.230
-
-
0.235
-
-
0.139
-
-
0.026
-
-
0.140
-
-
0.612
-
-
3
Retention time
Table 2. Composition of the volatile oil of Eucalyptus microtheca flowers.
No
1
2
3
4
5
6
7
8
9
10
1
%1
0.504
16.246
0.078
0.271
0.051
11.082
0.263
7.006
0.367
13.522
Compound
α –thujene
α -pinene
α -fenchene
Comphene
Verbenene
β - pinene
β -myrcene
α -phellandrene
α -terpinene
o- cymene
Compound percentage
2
Retention index
RI2
817
841
866
891
916
940
955
976
997
1018
RT3 (min)
9.331
9.652
9.976
10.028
10.198
11.256
11.957
12.477
12.983
13.246
3
Retention time
AJP, Vol. 5, No. 6, Nov-Dec 2015
544
Maghsoodlou et al.
Continued table 2.
No
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
61
62
63
64
65
66
67
68
69
70
71
72
73
74
75
76
77
78
79
80
1
Compound percentage
%1
2.131
2.713
0.149
0.868
0.093
0.189
0.058
0.113
0.085
0.147
0.365
0.303
0.088
0.070
1.052
0.202
0.425
0.160
0.392
0.365
0.167
0.063
0.115
0.787
0.494
0.129
0.170
0.150
0.063
0.063
0.542
0.040
0.227
0.122
0.112
0.073
7.444
0.080
1.632
0.400
0.311
0.320
2.135
0.318
0.667
0.248
1.040
0.045
0.070
0.975
0.253
0.221
1.848
5.419
1.044
0.631
0.212
0.196
0.217
0.791
0.444
0.120
0.246
0.321
0.375
0.167
0.918
0.425
0.145
5.414
Compound
Sabinene
Limonene
cis-ocimene
γ -terpinene
Isopropenyltoluene-cymene
α -terpinolene
Linalool L
Appel oil
D-fenchyl alcohol
Hexadecane
Trans-pinocarveol
Pinocarvone
4-methyl-1,3-heptadiene (c,t)
2, 4-hexadiene, 2, 5-dimethyl4-terpineol
Myrtenal
α -terpineol
Myrtenol
Dodecane
β -citronellol
Piperitone
Citrol
Citronellyl formate
Diglycol dimethacrylate
Carvacrol
2-butylpyridine
Isoledene
Copaene
Tetradecane
β -elemene
α -gurjunene
Seychelene
Trans-Caryophyllene
γ -selinene
Calarene
β - gurjunene
Aromadendrene
α -humulene
Alloarmadendrene
α -amorphene
β –selinene
α -guaiene
Ledene
α –muurolene
γ -cadinene
Calamenene
δ -cadinene
Cadina-1, 4-diene
α -calacorene
Epiglobulol
β -maaliene
Plustrol
Spathlenol
Globulol
Veridiflorol
Ledol
Hexadecane
α -ylangene
Isospathulenol
Tau-cadinol
α -cadinol
Cadalene
N-octadecane
Tetradecanamide
n-hexadecanoic acid
Ecosane
Hexaadecanamide
Octadecanoic acid
Docosan
9-octadecenamide
2
Retention index
RI2
1038
1059
1080
1101
1122
1143
1151
1170
1190
2639
1229
1248
1267
1287
1306
1326
1345
1365
1408
1428
1448
1487
1507
1527
1546
1750
1779
1809
1839
1615
1631
1647
1664
1680
1697
1713
1729
1746
1762
1779
1795
1811
1828
1844
1861
1877
1893
1910
1926
2374
2403
2433
2462
2492
2521
2580
2698
2727
2757
2786
2372
2392
3211
2653
2676
2700
2723
2746
2769
2793
RT3 (min)
13.465
13.586
13.993
14.857
15.942
16.195
16.669
16.956
17.108
38.511
18.155
18.779
19.161
19.351
20.011
20.218
20.561
20.916
21.584
22.624
22.879
23.727
24.60
25.673
25.898
29.074
29.249
29.322
29.463
29.933
30. 707
30.833
30.967
31.272
31.524
31.621
31.901
32.31
32.619
33.272
33.58
33.744
34.051
34.225
34.686
34.81
l
35.395
35.507
36.334
36.482
36.637
36.864
37.288
37.497
37.867
38.735
38.826
39.071
39.268
39.708
40.257
45.874
50.157
50.804
52.389
56.50
56.848
58.363
61.623
3
Retention time
AJP, Vol. 5, No. 6, Nov-Dec 2015
545
Essential oil composition of Eucalyptus microtheca and Eucalyptus viminalis
Continued table 2.
No
Compound
%1
RI2
81
82
83
Di-[2-ethylhexyl] phthalate
4-methylenespiro[2,4]heptane
(2-methylprop-1-enyl)cyclohexa- 1, 3-diene
1-(2′-hydroxy-3′,4′dimethylphenyl) ethanone
Trans-1,6-dimethyl bicycle
(4.3.0) non-2-en-7-one
7, 9-di-tert-butyl-1-oxaspiro
[4.5] deca-6, 9- diene-2, 8-dione
1, 3- cyclohexadiene, 2-methyl5-(1-methylethyl), monoepoxide
1H-cyclopropa[e]azulene,
decahydro-1, 1, 7-trimethyl-4methylene-,[1aR (1a.1alpha.
4a.beta. 7b.alpha)] - 7.alpha,
7a.beta
0.584
0.055
0.098
2816
1209
1467
66.492
17.288
23.271
0.603
2668
38.611
0.346
2551
37.595
0.117
2630
48.094
0.139
1384
21.004
0.243
2610
38.049
84
85
86
87
88
1
2
Compound percentage
RT3 (min)
3
Retention index
Retention time
(5.665%), P-cymen (5.251%), and βpinene (5.006%) were the major
constituents (Table 1).
In the oil of E. microtheca flowers, 88
compounds representing 100%, were
identified in which α-pinene (16.246%),
O-cymen (13.522%), β-pinene (11.082%),
aromadendrene (7.444%), α-phellandrene
(7.006%), globulol (5.419%), and 9octadecenamide (5.414%) were the major
components (Table 2). Sixty six
compounds representing 100% were
identified in the essential oil of E.
viminalis leaves. The major compounds
were 1, 8-cineole (57.757%), α-pinene
(13.379%), limonene (5.443%), and
globulol (3.054%) (Table 3).
The
presence
of
monoterpenes
(60.899%), sesquiterpenes (28.328%),
polyketides and fatty acids (1.714%),
alkanes (1.372%), amides (6.653%),
aromatic (0.115%), and other compounds
(0.871%) was revealed for E. microtheca
flower oils. In E. viminalis leaf oils,
monoterpenes (83.037%) were the major
components followed by sesquiterpenes
(14.97%) and other minor components
such as polyketides and fatty acids
(0.496%), alkanes (0.046%), aromatic
compounds
(0.013%),
and
other
compounds (1.404%).
The results showed in the essential oil
of E. microtheca leaves, 101 compounds
representing 100%, were identified.
Among them, α-phellandrene (16.487%),
aromadendrene
(12.773%),
α-pinene
(6.752%), globulol (5.997%), ledene
Table 3. Composition of the volatile oil of Eucalyptus viminalis leaves.
No
1
2
3
4
5555
6
7
8
9
10
11
12
13
14
1
%1
0.085
0.068
0.070
0.076
0.722
0.039
0.983
0.071
0.036
0.059
0.025
0.038
1.372
0.094
Compound
Pinocarvone
2, 5-octadiene
δ -terpineol
Borneol
4-terpineol
P-cym-8-ol
β -fenchyl alcohol
P-mentha-1, 8-dien-3-one
5, 6-decanedione
Copaene
Methyleugenol
Eudesma-3, 7(11)-diene
α -gurjunene
Valencene
Compound percentage
2
Retention index
RI2
1345
1365
1384
1404
1423
1443
1462
1487
1720
1750
1779
1582
1598
1615
RT3 (min)
18.832
19.353
19.461
19.593
20.031
20.269
20.703
21.97
26.596
29.359
29.59
30.196
30.779
31.309
3
Retention time
AJP, Vol. 5, No. 6, Nov-Dec 2015
546
Maghsoodlou et al.
Continued table 3.
No
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
61
62
63
64
65
66
1
Compound
Calarene
Selina-3, 7 (11)-diene
Aromadendrene
Alloarmadendrene
Isoamyl phenyl acetate
β -selinene
Ledene
α - muurolene
γ -cadinene
calamenene
δ -cadinene
Epiglobulol
γ –gurjunene
Palustrol
Globulol
Veridiflorol
1, 3-dimethyl-5-ethyladamantane
Trans- β -farnesene
α –cadinol
Citronellyl acetate
N-hexadecanoic acid
Pentacosane
Octanal
2-methyl-1, 3-cycloheptadiene
α -thujene
α -pinene
α -fenchene
comphene
β - pinene
β -myrcene
α -phellandrene
o- cymene
1, 8-cineole
Limonene
Cis-ocimene
β - ocimene Y
isoamyl butyrate
γ –terpinene
Dehydro-p-cymen
α -terpinolene
Linalool L
Appel oil
Isoamyl valerate
Fenchol
Valeric acid 4-pentenyl ester
Trans-pinocarveol
(+)-(2S, 4R)-p-mentha- 1(7), 8dien-2-ol
1H-indene, 1ethylideneoctahydro-7a-methyl-,
(1E, 3a.alpha. 7a.beta)
Bicyclo [4.4.0] dec-1-ene, 2isopropyl-5-methyl-9-methylene
Caryophylla-2(12), 6(13)-dien-5one
1-(2′-hydroxy-3′,4′dimethylphenyl) ethanone
2-propenoic acid, 2-methyl-,1,2ethanediyl ester
Compound percentage
2
%1
0.407
0.057
3.925
2.023
0.202
0.156
0.639
0.089
0.201
0.279
0.233
0.555
0.169
0.142
3.054
0.881
0.250
0.070
0.106
0.063
0.030
0.046
0.019
0.041
0.035
13.379
0.018
0.063
0.555
0.857
0.169
0.118
57.757
5.443
0.013
0.011
0.013
0.514
0.094
0.771
0.099
0.668
0.028
0.035
0.119
0.212
0.067
RI2
1631
1647
1664
1680
1697
1713
1729
1746
1762
1779
1795
2138
2168
2197
2227
2256
2286
2374
2138
2158
2327
2351
866
891
916
940
965
990
1014
1018
1038
1059
1080
1101
1122
1143
1164
1185
1206
1209
1229
1248
1267
1287
1306
1326
1507
RT3 (min)
31.567
31.657
31.949
32.707
33.12
33.617
34.089
34.258
34.723
34.848
35.119
36.403
36.538
36.688
37.369
37.586
37.674
38.289
39.765
42.108
50.917
66.562
7.611
8.907
9.373
9.732
10.009
10.055
11.191
12.001
12.443
13.283
13.919
13.98
14.113
14.56
14.686
14.941
16.012
16.276
16.784
17.031
17.14
17.275
17.407
18.248
22.283
0.466
2315
37.931
0.191
2433
39.327
0.230
2344
38.107
0.598
2403
38.692
0.068
1527
25.832
Retention index
3
Retention time
Table 4. Comparison of the composition of the volatile oil of E. microtheca leaves and flowers with E. viminalis
leaves from Zahedan.
No
1
2
3
4
5
6
7
8
9
10
11
1
%1
0.742
6.752
0.079
5.006
0.533
16.487
0.832
5.251
2.194
1.503
1.655
Compound
α –thujene
α -pinene
Comphene
β - pinene
β -myrcene
α -phellandrene
α -terpinene
P- cymene
β -phellandrene
Limonene
Cis-ocimene
E. microtheca leaves
2
E. microtheca flower
%2
0.504
16.246
0.271
11.082
0.263
7.006
0.367
2.713
0.149
3
%3
0.035
13.379
0.63
0.555
0.857
0.169
5.443
0.013
E. viminalis leave
AJP, Vol. 5, No. 6, Nov-Dec 2015
547
Essential oil composition of Eucalyptus microtheca and Eucalyptus viminalis
Continued table 4.
No
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
61
62
63
64
65
66
67
68
69
70
71
72
73
74
75
76
77
78
79
80
81
82
1
Compound
β –ocimene Y
γ -terpinene
Cymene
α -terpinolene
Rosefuran
Cycloheptanmethanol
Linalool L
Isoamyl isovalerate
Isoamyl valerate
Fenchol
Trans-pinene hydrate
Allocimene
1-terpineol
1-methylnorcarane
Ethylbenzoate
4-terpineol
1-(adamantly) cyclohexene
β -fenchol
Cis-sabinol
Thiophene, 2-ethyl-5-methyl
Ascaridole
Dicyclobutylidene oxide
Divinyldimethylsilane
Piperitone
1-methoxyhept-1-yne
Citronellyl formate
Carvacrol
α –cubebene
Isoledene
Copaene
2-pentene-1-ol, 2-methyl
α –gurjunene
Trans-caryophyllene
Aromadendrene
Epizonaren
α –humulene
alloarmadendrene
γ –gurjunene
α –copaene
β –selinene
β –panasinsene
ledene
α –muurolene
Geremacrene B
α –amorphene
cis-calamenene
δ -cadinene
Cadina-1, 4-diene
α –calacorene
α –cadinene
Ledane
Epiglobulol
β –maaliene
Palustrol
Spathlenol
Globulol
Veridiflorol
1, 3-dimethyl-5-ethyladamantane
Ledol
γ- curcumene
Isospathulenol
Tau-muurolol
δ -cadinol
Guaia-3, 9-diene
α– cadinol
Vulgarol A
Hexadecanoic acid
2-tridecanol
Hexadecanoic acid ethyl ester
Decyltetraglycol
Tricosane
E. microtheca leaves
2
%1
0.101
1.235
0.024
0.425
0.024
0.061
0.093
0.529
0.056
0.076
0.062
0.049
0.045
0.051
0.124
1.256
0.042
0.203
0.224
0.120
0.085
0.084
0.114
0.196
1.809
0.029
0.420
0.160
0.278
0.308
0.215
1.897
0.539
12.773
0.067
0.142
2.520
0.327
0.755
0.525
0.702
5.665
0.398
0.099
1.666
0.207
2.663
0.103
0.087
0.163
0.092
1.167
0.306
0.190
1.915
5.997
1.243
0.285
0.753
0.391
0.300
1.580
0.231
0.292
0.806
0.129
0.093
0.028
0.025
0.025
0.012
E. microtheca flower
%2
0.868
0.189
0.058
1.052
0.115
0.494
0.170
0.150
0.542
0.227
7.444
0.080
1.632
0.4
0.045
0.070
0.975
0.253
0.221
1.848
5.419
1.044
0.631
0.217
0.444
0.375
3
%3
0.011
0.514
0.771
0.099
0.028
0.722
0.059
1.372
3.925
2.023
0.169
0.156
0.639
0.089
0.233
0.555
0.142
3.054
0.881
0.250
0.106
0.030
-
E. viminalis leave
AJP, Vol. 5, No. 6, Nov-Dec 2015
548
Maghsoodlou et al.
Continued table 4.
No
83
84
85
86
87
88
89
90
91
92
93
94
95
96
97
98
99
100
101
1
Compound
Benzonitrile, m-phenethyl
Pentacosane
Pentaethoxylated pentadecyl alcohol
1-cyclohexene-1-carboxaldehyde, 4-(1methylethyl)
Cyclohexene, 3-methyl-6-(1-methylethyl)
2- cyclohexene-1-ol, 2-methyl-5-(1methylethenyl)-, trans2, 3-dimethyl-cyclohexa-1, 3-diene
α –campholonic acid
Furan, 2, 3-dihydro-4-(1-methylpropyl)
(E)-3-isopropyl-6-oxo-2-heptenal
1, 5, 5-trimethyl-6-methylene- cyclohexene
2, 6, 10-trimethyl-2, 5:7, 10-dioxidododeca-3, 11-diene-5-ol
Tricyclo [6.3.0.1(2, 3)] undec-7-ene, 6, 10,
11, 11-tetramethyl
1-methyl-4-isopropyl-cis-3hydroxycyclohex-1-ene-6-one
1H-cyclopropa[a]naphthalene, decahydro1,1,3a-trimethyl-7-methylene-,
[1as(1a.1alpha.,3a.alpha.,7a.beta.,7b.alpha.)]
%1
Naphthalene, 1, 2, 3, 4, 4a, 7- hexahydro-1,
6- dimethyl-4-(1-methylethyl)
Bicyclo[3.1.0]hex-2-ene,2-methyl-5- (1methylethyl)
(+)-(1R, 2S, 4R, 7R)-7-isopropyl-5- methyl5- bicycle [2.2.2] octen-2-ol
1, 6-dimethyl-2-cyano-3-ethyl-3- piperidine
E. microtheca leaves
2
%3
%
0.032
0.073
0.036
0.170
-
0.046
-
0.108
0.059
-
-
0.390
0.049
0.458
0.058
0.056
0.268
-
-
0.138
-
-
0.230
-
-
0.235
-
-
0.139
-
-
0.026
-
-
0.140
-
-
-
-
0.612
E. microtheca flower
Discussion
The comparison of results showed that
there are some differences and similarities
between the oil compositions of these
Eucalyptus species. These results are
shown in Table 4. The percentages of
sesquiterpene
and
monoterpene
compounds were similar in E. microtheca
leave oils, but the percentages of these
components were less than those of E.
viminalis leave and E. microtheca flower
oil.
Studies
have
revealed
that
monoterpenes have insecticidal activities
against
the
stored–product
insects
(Rajendran
and
Sriranjini,
2008;
Papachristos et al., 2004). Our study
showed that the major monoterpene
compounds were in E. viminalis leave and
E. microtheca flower oil. These
compounds consist of 1, 8- cineole, αpinene, and β-pinene which have been
shown to have insecticidal effects against
some major insects that infect the stored
crops (Rajendran and Sriranjini, 2008).
Therefore, the essential oil of E. viminalis
3
E. viminalis leave
leaves and E. microtheca flowers from
Zahedan, Iran could be a valuable
alternative to chemical control strategies
which have undesirable effects such as
environmental pollution and direct toxicity
to people. As it is evident from Table 3, the
main component of the essential oils of E.
viminalis leaves was 1, 8-cineole
(57.757%), but it was not identified in E.
microtheca leaf and flower oils. 1, 8cineole, which is a terpenoid oxide present
in many plant essential oils, displays antimicrobial, anti-inflammatory, and antinociceptive effects (Juergens et al., 2003;
Santos and Rao, 2000).
The percentage of α-pinene in the oil of
E. microtheca flowers and E. viminalis
leaves was 16.246% and 13.379%,
respectively, while in E. microtheca leave
oil it was less than 10%. Results indicated
that some of E. microtheca leaf oil
compounds such as α-phellandrene
(16.487%) and aromadendrene (12.773%)
were higher compared with E. microtheca
flower and E. viminalis leave oils. The oil
AJP, Vol. 5, No. 6, Nov-Dec 2015
549
Essential oil composition of Eucalyptus microtheca and Eucalyptus viminalis
of E. microtheca flower contained βpinene (11.082%), while it was less than
10% in other oils (E. microtheca and E.
viminalis leave oil). The compounds such
as α-pinene and β-pinene were the main
components in the essential oil of E.
microtheca flowers (16.246% and
11.082%) and E. viminalis leaves
(13.379% and 0.555%), respectively.
These compounds have been proven to be
strong antioxidant and antimicrobial agents
as emphasized elsewhere (Ho, 2010).
Chemical composition of the essential
oil of Eucalyptus microtheca leaves
growing in different geographical locations
has been widely studied. Ogunwande et
al., (2003) reported that in the volatile oil
of Eucalyptus microtheca leaves from
Nigeria, 1, 8-cineole (53.80%) was the
main constituent in leaves (Ogunwande et
al., 2003). Sefidkon et al., (2007)
identified 22 components in the oil of E.
microtheca from Kashan in the central
region of Iran. The major components
were 1, 8-cineole (34.0%), P-cymene
(12.40%), α-pinene (10.70%), β-pinene
(10.50%), and virdiflorene (5.20%)
(Sefidkon et al., 2007). In another study,
the major constituent of E. microtheca leaf
oils from Semnan province was 1, 8cineole
(48.51%),
followed
by
aromadendrene
(18.31%),
α-pinene
(9.47%), and alloaromadendrene (4.67%)
as the other dominant constituent
(Hashemi-Moghaddam et al., 2013). There
are many references about the composition
of other Eucalyptus species in the
literature. For example, the main
constituents of the oil of E. sargentii from
Isfahan province were 1, 8-cineole (55.48
%), α-pinene (20.95 %), aromadendrene
(6.45 %), and trans-pinocarveol (5.92%)
(Safaei and Batooli, 2010). Assareh et al.,
(2007) also reported chemical composition
of the essential oils of six Eucalyptus
species from South West of Iran. The main
components identified in E. intertexta oil
were 1, 8-cineole (64.80%), terpinen-1-ol
(7.20%), and α-pinene (5.70%); in E.
largiflorens were 1, 8-cineole (47.0%), P-
cymene (10.60%), and α-terpineol
(8.50%); in E. kingsmillii were 1, 8-cineole
(77.0%), α-pinene (8.70%), and camphene
(3.80%); in E. dealbata were 1, 8-cineole
(70.60%), α-pinene (13.0%), and terpinen1-ol (3.70%). The major components of
the oil of E. loxophleba were 1, 8-cineole
(41.90%), α-pinene (13.70%), and
aromadendrene (3.70%), while the major
components of E. kruseana were
bicyclogermacrene (28.80%), α-pinene
(17.70%), and 1, 8-cineole (12.10%)
(Assareh et al., 2007). Abd El- Mageed et
al., (2011) identified chemical composition
of the essential oils of some Eucalyptus
species from Egypt. The major
components identified in E. citridora oil
were 3-hexen-1-ol (31.26%), cis-geraniol
(19.66%), citronellol acetate (13.68%), 5hepten-1-ol, 2, 6-dimethyl (13.14%), and
citronellal (9.36%); in E. gomphocephala
were dihydrocarveol acetate (50.82%) and
P-cymene (10.62%);
and the major
components of E. resinfera
were
eucalyptol (51.97%), spathulenol (9.22%),
α-terpineol acetate (8.78%), and transnerolidol (8.75%) (Abd El- Mageed et al.,
2011). Mubarak et al., (2014) reported γterpinene (71.36%) and O-cymene
(17.63%) as the major components of E.
camaldulensis from Malaysia (Mubarak et
al., 2014). Comparing the results of
different studies showed that although 1, 8cineole has not been identified in E.
microtheca leaf and flower oil from
Zahedan, but it was as the major
constituent of E. microtheca leaf oil from
Nigeria (53.80%), Semnan (48.51%),
Kashan (34.0%), and other Eucalyptus
species (E. kingsmillii 77.0%, E. dealbata
70.60%, E. intertexta 64.80%, E. viminalis
57.75%, E. sargentii 55.48%, E.
largiflorens 47.0%, and E. loxophleba
41.90%). The essential oil of some
Eucalyptus species rich in 1, 8-cineol are
widely used as a flavoring agent in
production of softeners, soap, toothpaste,
and other medicines (Sefidkon et al.,
2007), but the percentage of this
compound is different in species. This can
AJP, Vol. 5, No. 6, Nov-Dec 2015
550
Maghsoodlou et al.
be related to the type of the plant, the plant
parts (aerial or flower and leaf parts), the
geographical regions of the plant growing
places, and also the ecological conditions
of the plant. In addition, α-pinene
compound, which appeared as the major
constituent in the oil of E. sargentii
(20.95%), E. kruseana (17.70%), E.
viminalis (13.379%), E. loxophleba
(13.70%), E. dealbata (13.0%), and E.
microtheca from Kashan (10.70%) and
Semnan (9.47%), were present in low
concentration in E. microtheca leaf oils
(6.752%) from Zahedan. The amount of Pcymene compound in the oil of E.
microtheca leave from Kashan (12.40%)
also was much higher than that of E.
gomphocephala (10.62%), E. largiflorens
(10.60%), and E. microtheca (5.21%) from
Zahedan. In general, great quantitative and
qualitative
variations
in
volatile
composition of E. viminalis and E.
microtheca were seen between this and
other studies. These variations may be due
to the influence of geographical
differences, environmental and growing
conditions, physiological and biochemical
states of plants, genetic factors, and
different
extraction
and
analytical
procedures (Kokkini et al., 2004;
Hassanpouraghdam et al., 2011).
It can be concluded that the oils of these
two Eucalyptus species are good sources
of natural antioxidants to be used in
medicinal and food products to promote
human health and prevent diseases, which
should be investigated in further studies. In
addition, regarding environmental problem
and human health, these plants could be an
alternative source of insecticide agents
because many of their components have
little or no harmful effects on humans and
environment.
Acknowledgments
We are thanksful to the University of
Sistan and Baluchestan Research Council
for the partial support of this research.
There is not any conflict of interest in
this study.
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