107
American-Eurasian Journal of Sustainable Agriculture, 3(1): 107-110, 2009
ISSN 1995-0748
© 2009, American Eurasian Network for Scientific Information
This is a refereed journal and all articles are professionally screened and reviewed
O RIGINAL A RTICLES
Composition of Hypericum perforatum L. Volatile Oil from kashan Oil Composition of
Hypericum perforatum L.
2
Maryam Akhbari and
1
Department of Chemistry, Qom Branch, Islamic Azad University, Qom, Iran
Isfahan Research Center of Natural Sources, Kashan Station, Kashan, I. R. Iran
2
1
Hossein Batooli
Maryam Akhbari and Hossein Batooli.; Composition of Hypericum perforatum L. Volatile Oil from
kashan Oil Composition of Hypericum perforatum L: Am.-Eurasian J. Sustain. Agric., 3(1): 107-110,
2009
ABSTRACT
This study was designed to examine the chemical composition of the essential oil of Leaves, flowers and
fruits of perforatum L. growing wild in kashan. GC–MS analyses of the essential oil resulted in the
identification of 55 compounds, for leaves, representing 91.46% of the oil; á-pinene (29.33%) was the main
component. The analyses for Flower and fruit part resulted in the identification of 26 compounds, representing
95.96% of the oil; á-Amorphene (15.86%), á-Pinene (11.34%), Thymol (7.27%) and á-Campholene Aldehyde
(6.63%) were the main components, comprising 41.1% of the total oil.
Key words: Hypericum perforatum, essential oil, GC-Mass, á-pinene
Introduction
Essential oils of many plants have antioxidant and antimicrobial properties which are used in food,
cosmetic and pharmaceutical industries (Reische et al., 1998). The genus Hypericum, which is represented by
over 10 species in Iran (Karimi, 2002) is one of the medicinal plants that are used in traditional medicine
(Prajapati, et al., 2006). Members of this genus have been reported as antiviral, antistimulants, antidepressant
and stimulant bile flow. Hypericum perforatum, also known as St. John's W ort, is traditionally used as a
medicinal plant (Robson, et al., 1968); this plant is very significant in pharmacology (Pignatti, 1982,
Bombardelli, et al., 1995) and a great number of studies refer to the biologically active components isolated:
hypericin, pseudohypericin, hyperforin, adhyperforin, procyanidins andxanthones. A smaller number of studies
refer to the composition of the essential oil of H. perforatum (Reichling, et al, 2001, Kasper, 2001, LopezBazzocchi, et al., 1991, Meruelo, et al, 1988, Miskovsky, 2002, Gurevich, et al, 1971, Maisenbacher, et al.,
1992). Material collected in France, Italy, India, Turkey, Serbia have been investigated previously (M elzer, et
al., 1991, De Smet, et al., 1996, Schwob, et al., 2002, Mathis, et al., 1964).
There are Some investigations about essential oils of Hypericum Perforatum. For example the oil of H.
perforatum L. from southeastern France, reported that is rich in á-pinene, and about the oil of H. perforatum
L. from Greece, 2-methyloctane (17.8%), â-caryophyllene (10.3%), á-pinene (10.1%) and bicyclogermacrene
(4.8%). The major compounds in the oil of Hypericum perforatum angustifolium from Italy were 2methyloctane (21.1%), germacrene-D (17.6%) and á-pinene (15.8%). The French H. perforatum angustifolium
samples were characterized by spathulenol (21.1%) and branched tetradecanol (9.1% ) (M athis, 1964, Isabelle,
et al., 2002). The aim of this paper was to determine the composition of the oil of Hypericum Perforatum L.
wild-growing in kashan Karkas mountaines. There is no report about Chemical properties or compositions of
it in this area.
Corresponding Author: Maryam Akhbari, 1 Department of Chemistry, Qom Branch, Islamic Azad University, Qom,
Iran.
Am.-Eurasian J. Sustain. Agric., 3(1): 107-110, 2009
108
M aterials and methods
Plant Material
Materials for extraction were aerial parts of Hypericum Perforatum L. collected in from Kashan area
(Isfahan Province, central Iran, Karkas mountaines) in April 2007 which were dried in the shade at room
temperature. The voucher specimens of the plant were deposited in the Herbarium of Kashan Botanical Garden,
Research Institute of Forests and Rangelands, Kashan, Iran.
Extraction of essential oil
The arial parts of examined plants were dried in shadow at room temperature and 30 g of powdered
Leaves and 25 g of Flowers and fruits were hydrodistilled with a clevenger type apparatus for 4 h. The
yellowish oil (0.3 ml/ for leaves and 0.5 ml for flower and fruits) was dissolved in diethylether (1ml) and
collected and dehydrated by anhydrous sodium sulfate.
The solvent was evaporated at room temperature under vacuum and the oil was kept under nitrogen
atmosphere in -5°C.
Identification of the oil components
The oil of leaves was analyzed by GC/MS on a HEW LETT-PACKARD 6890 gas chromatograph coupled
a mass detector (HEWLETT-PACKARD model 6973 HP). The flower and fruit oil was analyzed by GC/MS
on a HEW LETT-PACKARD 6890 gas chromatograph coupled a mass detector (HEW LETT-PACKARD model
5973MSD).
The column for oil separation use a fused silica HP-5 column, 60 m length, 250 µm I.D., and 0.25 mm
film thickness.
The mass spectra were obtained by electron ionization at 70 eV. The oven temperature program for leaves
oil was 60° C (30 min) isotherm, then to 250° C at the rate 5° C/min. The injector temperature was 250° C.
For flower and fruit oil The oven temperature program for leaves oil was 50° C (5min) isotherm, then to 200°
C at the rate 5° C/min, then to 250° C at the rate 15° C/min, injector temperature was 250° C.
The carrier gas (helium) flow rate was 1 ml/min. The sample (1 µl) was injected with a split ratio of 1/90.
The compounds were identified using the W iley 275 library, retention times and MS fragmentation with
published data (Adams, 1995).
Results and Discussion
Results
The hydro distillation of the aerial parts of H. helianthemoides gave yellowish oil in 1% and 2% (v/w)
yields for leaves and flower parts.
For the leaves, fifty-five constituents were identified, containing for 91.46% of the total oil. Table 1 shows
the list of constituents identified in the essential oil of H. perforatum leaves. The retention time of the
components are listed in the table.
Table 2 shows the components identified in the essential oil of H. Perforatum flowers and fruits.
Discussion
Major component in the oil, for leaves, was á-Pinene (29.33%). Some of the other major products were:
á-Amorphene, â-Pinene, ä-Cadinene and á-Cadinene.
Major components in the oil, for the flowers and fruits, were á-Amorphene (15.86%), á-pinene (11.34%),
Thymol (7.27) and ä-Cadinene (5.72%).
Althought á-pinene was one of the main constituents of the essential oil in both table 1 and 2, did not
show high similarity between the essential oil compositions of the leaves and the flower and fruits. According
to the tables, it is found that the major component in the leaves was á-pinene but about the flower and fruit
was á-Amorphene (15.86%).
The studies on the oil composition of H. perforatum varieties and the difference between literature reports
on the oils, suggest that the identification of the varieties has to be taken into account as chemosystematic
variables.
Am.-Eurasian J. Sustain. Agric., 3(1): 107-110, 2009
Table 1: Chem ical com position
No
1
2
3
4
5
6
7
8
9
10
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
a) RT: Retention tim e
of H . Perforatum Leaves
Com pound
Cyclopentane, m ethylcam phene
á-pinene
verbenene
â-pinene
M yrcene
p-Cym ene
Lim onene
Trans â-O cim ene
gam m a-terpinene
Ethanone 1-phenyl
Linalool O xide
o-Isopropenyltoluene
U ndecane
á-cam pholene Aldehyde
trans-Pinocarveol
Verbenol
Trans-P-M enth-2-ene-1,8-diol
O ctanoic acid
Terpinene-4-ol
p-cym ene-8-ol
l-.alpha.-Terpineol
M yrtenal
Trans-(+)-Carveol
Carvone
Thym ol
Carvacrol
á-Cubene
á-Longipinene
á-Y langene
á-Copaene
â-Caryophyllene
(+)-Arom adendrene
Germ acrene-D
á-H um ulene
â-Selinene
á-Am orphene
á-gurjunene
ä-Cadinene
á-Cadinene
(-)-Caryophyllene O xide
á-Calacorene
(+)-Spathulenol
Erem ophilene
Cadina-1,4-diene
glubulol
â-oplopinone
Calarene
4-Isopropyl-1 ,6-dim ethyldecahydronaphthalene
guaiazolene
Valerenal
O ctadecane
N onadecane
H exadecanoic acid
H eneicosane
Table 2: Chem ical com position of H . Perforatum flowers and fruits
No
Com pound
1
á-pinene
2
á-cam pholene Aldehyde
3
isopinocarveol
4
Verbenol
5
P-M enth-1,8-diene-8-ol
6
P-Cym en-8-O l
7
(-)-á-Terpineol
8
M yrtenol
9
N O PO L
10
4-Isopropyl-1 ,6-dim ethyldecahydronaphthalene
11
Trans-(+)-Carveol
109
RTa
5.24
5.24
12.42
12.94
13.68
13.90
15.05
15.20
15.67
16.11
16.42
16.57
17.10
17.25
18.31
18.79
18.92
19.57
19.68
19.87
20.11
20.29
20.77
21.10
21.82
23.05
23.33
24.77
24.95
25.44
25.56
26.83
27.32
27.61
27.68
28.53
28.70
28.72
29.11
29.68
30.16
30.34
30.82
30.96
31.00
31.41
31.54
32.00
32.51
32.99
34.48
35.01
36.50
37.30
38.70
RTa
6.39
13.62
14.12
14.41
14.57
16.25
16.45
16.68
17.02
17.22
17.70
Com position(% )
3.00
0.80
29.33
0.35
3.89
0.84
1.20
1.00
0.23
0.22
0.35
0.40
0.80
1.10
2.10
1.20
0.70
2.50
0.44
0.26
0.50
1.23
2.93
1.20
0.16
2.90
0.18
0.39
0.15
0.27
0. 80
2.20
2.30
1.70
0.33
0.43
6.27
1.20
3.70
3.15
0.28
0.36
0.10
1.11
0.75
0.33
0.64
0.48
2.20
0.90
0.20
0.27
0.43
0.35
0.36
Com position (% )
11.34
6.63
3.82
3.46
2.89
1.22
1.90
2.91
2.06
3.82
2.96
Am.-Eurasian J. Sustain. Agric., 3(1): 107-110, 2009
Table 2: Continue
12
Thym ol
13
Tridecane
14
á-Cubebene
15
á-Copaene
16
Tetradecane
17
â-Caryophylene
18
Germ acrene-D
19
Arom adendrene
20
á-Am orphene
21
â-Selinene
22
Calarene
23
á-M uurolene
24
Pentadecane
25
ä-Cadinene
26
Spathulenol
a) RT: Retention tim e
110
21.01
21.29
23.33
24.42
25.62
26.23
26.65
27.04
28.68
29.01
29.41
29.66
29.83
30.61
32.66
7.27
0.87
1.07
1.72
0.82
4.86
1.00
4.42
15.86
1.66
3.13
0.94
1.67
5.72
1.94
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