thymopsis

J. Essent. OilH.
Res.,
21 (March/April 2009)

Essential Oil Composition of Hypericum thymopsis

Boiss.
Ayse
Mine Genler zkan,*
Ankara University, Faculty of Pharmacy, Department of Pharmaceutical Botany, 06100 Tandogan, Ankara, Turkey

Betl Demirci and Kemal Hsn Can Baser,

Anadolu University, Faculty of Pharmacy, Department of Pharmacognosy, 26470 Eskisehir, Turkey

Abstract
The composition of the essential oil obtained from the aerial parts of Hypericum thymopsis Boiss. (Guttiferae) was
analyzed by GC and GC/MS. The analysis resulted in the identification of 72 compounds representing 82.4% of the
oil. The major constituents found were spathulenol (10.8%), d-cadinene (7.1%), germacrene D (6.1%), g-muurolene
(5.9%), 2,3,6-trimethylbenzaldehyde (5%), g-cadinene (4.4%). The oil was rich in sesquiterpene hydrocarbons.
Key Word Index
Hypericum thymopsis, Guttiferae, essential oil composition, spathulenol, d-cadinene, germacrene D.

Introduction
The genus Hypericum, a member of the family Guttiferae
(known also as Hypericaceae or Clusiaceae) is very large and
represented by about 400 species throughout the world (1).
Eighty-nine Hypericum species occur in Turkey and 43 of which
are endemic as recorded in the Flora of Turkey. Plants of the
genus Hypericum generally have pale to dark yellow flowers
and transparently dotted leaves with red or black glands (24).
The genus Hypericum is known worldwide for its traditional and modern uses. Amongst the species, H. perforatum
is a potential plant for curing many diseases like cancer, tumors, AIDS, etc. and is very popular today in different parts
of the world especially as an antidepressant. The review of
literature indicates that, besides H. perforatum, other species
of the genus are also economically important, used as edible,
medicinal, fodder, fuel, dye, etc. (5). In Turkish traditional
medicine, the genus is known as kantaron, binbirdelik otu, kan
otu, kuzukran, mayasl otu and has also been used in wound
healing, treatment of gastric ulcers, as an antifungal agent and
for the treatment of several other diseases (6,7).
Previous studies have shown that the phytochemistry of
Hypericum species is diverse with naphthodianthrones, primarily represented by hypericin and pseudohypericin; flavonoids,
e.g., hyperoside, rutin or quercitrin; phloroglucinol derivatives,
e.g., hyperforin and adhyperforin; and xanthone compounds
such as mangiferin and isomangiferin (811).
Hypericum thymopsis is an endemic, perennial species
growing on calcareous hillsides of inner and eastern Anatolia

from sea level up to 1500 m of altitude (2). The essential oils

of Hypericum species growing in different regions of the world
have been studied (1254). The oil compositions from different
parts of these previously investigated species regarding their
major components are compiled in Table I. However, there is
no report on the analysis of the oil of H. thymopsis. Thus, the
aim of the present study was to examine the chemical composition of the oil isolated from the aerial parts of H. thymopsis.

Experimental
Plant material: Flowering aerial parts of Hypericum
thymopsis were collected from inner Anatolia, namely, Sivas:
Sarksla, Altnyayla, c.1500 m, on 02.07.2006. The species was
identified according to the morphological description in Flora
of Turkey and the East Aegean Islands (2). A voucher specimen was deposited in Ankara niversitesi Eczaclk Fakltesi
Herbaryumu (AEF), Ankara, Turkey (AEF 23797).
Isolation of the essential oil: Air dried plant material was
subjected to hydrodistillation using a Clevenger-type apparatus according to the method recommended in the European
Pharmacopoeia (55). The obtained oil was stored at +4C in
the dark prior to analysis.
Gas chromatography (GC): The GC analysis was carried
out using an Agilent 6890N GC system. FID detector temperature was 300C. In order to obtain same elution order with
GC/MS, simultaneous injection was done by using same column
and an appropriate operational contitions. Relative percentage
Received: May 2007

*Address for correspondence

Revised: October 2007

1041-2905/09/0002-01$14.00/0 2009 Allured Business Media
Vol. 21, March/April 2009

Accepted: January 2008

Journal of Essential Oil Research/1

Genler zkan et al.

Table I. Main components of the essential oils of other Hypericum species previously reported
Hypericum sp. (Reference) Part / Origin

Main Components (%)

H. acmosepalum (12)
ap / Asia
H. adenotrichum (13)
ap / Turkey
H. alpinum (14)
ap / Serbia
H. androsaemum (15)
(cultivated-2003)
ap / Portugal
H. ascyron (16)
ap / China
H. atomarium (17)
ap / Serbia
cyclohexane (19)
H. barbatum (14,18)
ap / Serbia

ap / Serbia
H. beanii (12)
ap / Asia
H. brasiliense (19)
wpl / Brazil
H. bupleuroides (20)
ap / Turkey
H. calycinum (12,13)
ap / Asia

ap / Turkey
H. cerastoides (13)
ap / Turkey
H. chinense (21)
br, l / China
H. choisyanum (12)
ap / Asia
H. coris (22)
ap / France
H. dogonbadanicum (23)
l, f / Iran
H. empetrifolium (24)
ap / Greece
H. ericoides (25)
ap / Spain
H. foliosum (26)
f / Azorean Islands
H. forrestii (12)
ap / Asia
H. heterophyllum (27)
ap / Turkey
H.hircinum (28)
fr, l / Italy
H. hirsutum (14,18,29)
ap / Serbia

ap / Serbia

ap / Serbia
H. hyssopifolium subsp.
elongatum var. elongatum (27) ap / Turkey
H. hyssopifolium var.
microcalycinum (30)
ap / Turkey
H. japonicum (31)
s, f, l / China
H. kouytchense (12,32)
ap / Asia

ap / China
H. lancasteri (12)
ap / Asia
H. lanceolatum subsp.
angustifolium (33)
ap / Runion Islands
H. lanceolatum subsp.
lanceolatum (33)
ap / Runion Islands
H. leschenaultii (12)
ap / Asia
H. linarioides (18,34)
ap / Serbia

ap / Turkey
H. lysimachioides var.
lysimachioides (30)
ap / Turkey
H. maculatum (14,18,35)
ap / Serbia

ap / Serbia

ap / Serbia
H. monogynum (12)
ap / Asia
H.montbretii (13)
ap / Turkey
H. olympicum (18,36,37)
ap / Serbia

ap / Serbia

ap / Greece
H. patulum (12)
ap / Asia
H. perfoliatum (24,38,39)
ap / Greece

ap / Greece

ap / Algeria
H. perforatum (13,14,18,24,
36,37,4048)
ap / Turkey

ap / Serbia

ap / Serbia

ap / Greece

ap / Serbia

ap / Greece

ap / Uzbekistan

b-selinene (16), ar-curcumene (13)

germacrene D (38), undecane (17), a-pinene (16)
b-pinene (13), g-terpinene (8), (b)-caryophyllene (7)

2/Journal of Essential Oil Research

limonene (15), (E)-2-hexenal (8), 1-octene (7)

1-ethoxyethyl acetate (19), b-caryophyllene (18), 3-hexenol (17)
isocaryophyllene (24), g-cadinene (22), 2,4-diisopropenyl-1-methyl-1-vinyla-pinene (17), b-pinene (17), caryophyllene oxide (12)
(Z,Z)-9,12-octadecadienoic acid (10), hexadecanoic acid (8)
g-muurolene (11), b-selinene (16), caryophyllene oxide (19)
b-caryophyllene (30), caryophyllene oxide (10)
b-sesquiphellandrene (33), b-caryophyllene (20), selina-3,7(11)-diene (7)
a-terpineol (12), b-pinene (29)
a-pinene (24), b-pinene (14)
a-pinene (58), undecane (5), b-pinene (3)
a-ocimene (93), b-ocimene (1)
cis-eudesma-6,11-diene (11), allo-aromadendrene (8)
ar-curcumene (40), g-cadinene (15)
a-pinene (35), b-pinene (32), limonene (12)
a-pinene (36), g-gurjunene (11)
ar-curcumene (1020), a-pinene (510), g-muurolene (510), d-cadinene (510)
nonane (2973), limonene (746), terpinolene (119)
a-pinene (10), caryophyllene oxide (13)
isocaryophyllene (17), a-pinene (12), d-cadinene (10)
nonane (36, 19), b-pinene (17, 3), a-pinene (9, 1), limonene (13, 3)
nonane (25), undecane (13), (-)-(b)-caryophyllene (5)
nonane (41), undecane (12)
undecane (32), patchoulene (12), caryophyllene oxide (9)
a-pinene (57), b-pinene (9), limonene (6)
caryophyllene oxide (20), caryophyllene alcohol (9), a-amorphene (6)
undecane (17), 2,4-dimethyl-heptane (17)
g-muurolene (12), cis-b-guaiene (11)
g-muurolene (11), caryophyllene oxide (9)
b-selinene (11), eudesmadienone (11)
nonane (54), germacrene D (4)
n-nonane (16), d-cadinene (8)
cuparene (25), g-muurolene (17)
a-pinene (12), nonane (11)
d-cadinene (7), g-muurolene (6), (Z)-b-farnesene (5)
caryophyllene oxide (31), b-selinene (7), a-longifolene (6)
globulol (10), spathulenol (7)
nonane (15), hexadecanoic acid (9)
b-farnesene (10), undecane (8), b-caryophyllene (8)
tricosane (13), myrcene (10)
a-pinene (26), b-pinene (19), a-terpineol (7)
germacrene D (8), spathulenol (7)
(E)-anethole (31), b-farnesene (12)
germacrene D (16), (b)-caryophyllene (7)
b-selinene (15), ar-curcumene (8)
a-pinene (41), b-pinene (7)
a-pinene (49, 34), d-cadinene (5, 8)
thymol (22), T-cadinol (19)
a-pinene (50), carvacrol (22)
a-pinene (9), (Z)-b-farnesene (7), germacrene D (7)
2-methyloctane (21), a-pinene (14)
a-pinene (21), 2-methyloctane (12)
b-caryophyllene (14), 2-methyloctane (13)
a-pinene (21), 2-methyloctane (13)
b-caryophyllene (12), caryophyllene oxide (6)
Vol. 21, March/April 2009

H. thymopsis

H. perforatum var.
angustifolium (49, 50)

H. pseudohenryi (12)
H. richeri (18)
H. rumeliacum (14,18,24)


H. rumeliacum subsp.
apollinis (51)
H. sampsonii (41,52)

H. scabrum (40,46,53)


H. tetrapterum (18,37)

H. triquetrifolium (24,54)

H. xmoserianum (12)

l / China
ap / France
ap / Serbia
l / India
ap / Serbia
ap / Turkey
ap / Greece
ap / France

caryophyllene (19), germacrene D (11)

caryophyllene oxide (1518), b-caryophyllene (718)
n-eicosane (1-31), 1-tetradecanol (524)
a-pinene (67), nonane (5)
nonane (64), p-cymene (5)
a-pinene (62), 3-carene (8)
germacrene D (23, 17), 2-methyloctane (11, 18)
germacrene D (037), b-caryophyllene (028)

f / Italy
ap / Serbia
ap / Asia
ap / Serbia
ap / Serbia
ap / Serbia
ap / Greece

2-methyloctane (21), germacrene D (18), a-pinene (16)

caryophyllene oxide (15), trans-anethole (10)
b-selinene (19), caryophyllene oxide (6)
(E)-anethole (10), globulol (9)
b-pinene (22), a-pinene (19), p-cymene (9)
hexadecanoic acid (12), dodecanoic acid (8)
a-pinene (43), b-pinene (10)

ap / Greece
l / China
l, fr / China
ap / Uzbekistan
ap / Turkey
ap / Iran
ap / Serbia
ap / Greece
ap / Greece
l, f / Italy
ap / Asia

a-pinene (44), b-pinene (10)

ocimene (14), undecane (12)
ocimene (14,0), undecane (12, 13), nonane (4, 10)
a-pinene (11), spathulenol (7), p-cymene (6)
a-pinene (72), b-caryophyllene (5)
a-pinene (45), nonane (6), thymol (5)
2,6-dimethyl-3,5-heptanedione (8), globulol (6)
a-copaene (11), a-longipinene (10)
2-methyloctane (17), a-pinene (15)
nonane (815), a-pinene (13, 10), myrcene (16.5)
g-muurolene (11), d-cadinene (10)

ap: aerial part; wpl: whole plant; s: stem; br: brach; l: leaf; f: flower; fr: fruit.

amounts of the separated compounds were calculated from

FID chromatograms.
Gas chromatography/mass spectrometry (GC/MS): The
GC/MS analysis was carried out with an Agilent 5975 GC-MSD
system. Innowax FSC column (60 m x 0.25 mm, 0.25 mm film
thickness) was used with He as carrier gas (0.8 mL/min). GC
oven temperature was kept at 60C for 10 min, programmed
to 220C at a rate of 4C/min, kept isothermal at 220C for
10 min and then programmed to 240C at a rate of 1C/min.
Injection volume was 1 mL (10%) in hexane. Split ratio was
adjusted at 40:1. The injector temperature was at 250C. MS
were taken at 70 eV. Mass range was from m/z 35 to 450.
Identification of components: Identification of the oil
components were carried out by comparison of their relative
retention times with those of authentic samples or by comparison of their relative retention index (RRI) to series of
n-alkanes. Computer matching against commercial (Wiley GC/
MS Library, Adams Library, MassFinder 3 Library) (56,57),
and in-house Baser Library of Essential Oil Constituents
built up by genuine compounds and components of known
oils, as well as MS literature data (5860), was also used for
the identification.

Results and Discussion

Air-dried aerial parts of H. thymopsis gave an average oil
yield of 0.14% (v/w) based on dry weight of the sample. The
oil was liquid and light yellow in color. The oil was analyzed by
means of a simultaneous GC and GC/MS system. The chemical
composition of the oil is given in Table II where the components
are listed in order of their elution on the column. Seventy-two
Vol. 21, March/April 2009

constituents representing 82.4% of the oil were identified.

Spathulenol (10.8%), d-cadinene (7.1%), germacrene D (6.1%),
g-muurolene (5.9%), 2,3,6-trimethylbenzaldehyde (5%) and
g-cadinene (4.4%) were characterized as the main components.
Considering the different groups of compounds, sesquiterpene
hydrocarbons had the highest contribution (38.2%) whereas
monoterpene hydrocarbons had the lowest (0.2%). The total
sum of oxygenated sesquiterpenes was calculated to be 22.9%,
whereas alkanes and alkenes comprised 7.1%. Oxygenated
monoterpenes (2.4%) and fatty acids (2.6%) were also present in lesser amounts in addition to other compounds (9%),
as seen in Table III.
After comparing the main constituents of the previously
studied Hypericum species (1254) with those of H. thymopsis, it appears that each of these species has a different set of
dominant compounds, so it is not easy to observe a chemical
resemblance between the species of this genus. But it is worth
noting that, a-pinene, which is the frequent main component
in the oils of these aforementioned species, was found in relative amount of less than 1%. Spathulenol was found to be the
major component only in three species out of 50 taxa analyzed
before namely, H. maculatum, H. olympicum and H. scabrum
(14,18,40). d-Cadinene was detected in H. xmoserianum, H. ericoides, H. heterophyllum, H. lanceolatum subsp. lanceolatum, H.
linaroides and H. perfoliatum (12,25,27,33,34,38). Germacrene
D was also present in high amounts in H. adenotrichum, H.
lanceolatum subsp. angustifolium, H. olympicum, H. perforatum,
H. perforatum var. angustifolium (13,14,18,33,37,41,4749).
Chemical profiling using volatiles may be useful in taxonomical classifications. The results presented here confirm some
specific features of the oil composition of Hypericum species
Journal of Essential Oil Research/3

Genler zkan et al.

Table II. The percentage composition of the essential oil of Hypericum thymopsis
RRI

Compound

1032
1100
1300
1466
1482
1493
1497
1500
1535
1549
1589
1591
1597
1600
1600
1612
1628
1661
1677
1700
1704
1726
1740
1755
1773
1776
1799
1807
1827
1849
1849
1868
1900
1915
1918
1925

a-pinene
undecane
tridecane
a-cubebene
longipinene
a-ylangene
a-copaene
pentadecane
b-bourbonene
b-cubebene
b-ylangene
bornyl acetate
b-copaene
hexadecane
b-elemene
b-caryophyllene
aromadendrene
allo-aromadendrene
epi-zonarene
heptadecane
g-muurolene
germacrene D
a-muurolene
bicyclogermacrene
d-cadinene
g-cadinene
cadina-1,4-diene (= cubenene)
a-cadinene
(E,E)-2,4-decadienal
cuparene
calamenene*
(E)-geranyl acetone
epi-cubebol
nonadecene
b-calacorene
2,3,4-trimethylbenzaldehyde

0.2
0.4
0.1
0.2
0.7
0.4
1.8
tr
0.2
0.2
0.3
1.1
0.4
0.2
0.2
0.3
0.8
0.1
0.3
0.3
5.9
6.1
1.4
2.1
7.1
4.4
0.7
1.2
0.1
0.1
2.0
0.3
0.2
0.4
0.1
0.4

RRI

Compound

1941
1945
1957
1958
1973
1984
2000
2019
2037
2161
2080
2100
2144
2144
2148
2130
2173
2179
2187
2200
2209
2210
2219
2239
2247
2255
2278
2369
2384
2500
2607
2700
2795
2800
2900
2931

a-calacorene
1,5-epoxy-salvial(4)14-ene
cubebol
(E)-b-ionone
dodecanol
g-calacorene
eicosane
2,3,6-trimethylbenzaldehyde
salvial-4(14)-en-1-one
muurola-4,10(14)-dien-1-ol
cubenol
heneicosane
rosifoliol
spathulenol
(Z)-3-hexenyl benzoate
salviadienol**
6-epi-cubenol
3,4-dimethyl-5-pentylidene-2(5H)-furanone
T-cadinol
docosane
T-muurolol
copaborneol
a-muurolol
carvacrol
trans-a-bergamotol
a-cadinol
torilenol
eudesma-4(15),7-dien-1b-ol
hexadecanol
pentacosane
octadecanol
heptacosane
eicosanol
octacosane
nonacosane
hexadecanoic acid
Total (72 identified compounds)

1.1
0.7
0.2
0.2
0.4
0.1
0.6
5.0
1.2
0.1
0.2
0.4
0.1
10.8
1.2
1.0
0.2
0.2
0.7
0.1
0.7
0.4
0.1
1.0
0.2
1.1
1.7
3.3
0.8
0.5
0.3
0.3
0.5
0.2
3.5
2.6
82.4

RRI = Relative retention indices calculated against n-alkanes; % calculated from FID data; tr = trace (< 0.1%); *correct isomer not identified; ** tentative identification.

Table III. The chemical class distribution of the oil components

of Hypericum thymopsis

Chemical class

Number of identified
compound

Monoterpene Hydrocarbons
Oxygenated Monoterpenes
Sesquiterpene Hydrocarbons
Oxygenated Sesquiterpenes
Alkanes+Alkenes
Fatty acid
Others
Total

1
3
26
18
14
1
9
72

%
0.2
2.4
38.2
22.9
7.1
2.6
9.0
82.4

from Turkey and contribute to a better knowledge of the genus.

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