FLAVOUR AND FRAGRANCE JOURNAL

Flavour Fragr. J. 2001; 16: 204–206

DOI: 10.1002/ffj.979

Essential oil composition of Hypericum perfoliatum L.

growing in different locations in Greece
M. Couladis,1 * P. Baziou,1 P.V. Petrakis2 and C. Harvala1
1Department of Pharmacognosy, School of Pharmacy, University of Athens, Panepistimioupolis Zografou, 157 71 Athens, Greece
2Ministry of Agriculture, Department of Informatics and Biodiversity, Group of Natural Resource Monitoring, Aharnon 381, 111
#43 Athens, Greece
Received 22 June 2000
Revised 3 November 2000
Accepted 14 November 2000

ABSTRACT: The essential oils of the aerial parts of Hypericum perfoliatum L., collected in two different locations
in Greece, were obtained by hydrodistillation and analysed by GC–MS. Fifty constituents were identified. The
monoterpene hydrocarbons had the highest contribution. The major constituents in sample A were ˛-pinene
(48.6%) n-nonane (8.5%) and υ-cadinene (4.6%), while those of sample B, were ˛-pinene (34.2%) ˇ-pinene
(9.2%) and υ-cadinene (8.1%). Copyright  2001 John Wiley & Sons, Ltd.
KEY WORDS: Hypericum perfoliatum L.; Guttiferae; essential oil composition; ˛-pinene; n-nonane; ˇ-pinene;
υ-cadinene

Introduction their flowering period in May 1999. The first population

Hypericum perfoliatum L. belongs to the genus Hyper-
icum, which contains more than 400 species, widespread
in warm-temperate areas throughout the world and well
represented in the Mediterranean and the Near East
area.1 H. perfoliatum L. is a perennial plant, belong-
ing to the family Guttiferae, usually growing in shady
places among rocks.2 There are a number of literature
reports on phytochemical analyses of this genus.3 – 12
Even though important pharmacological properties have
been attributed to extracts of Hypericum spp.13 – 17 few
reports concerning the volatile chemistry of the genus
have appeared.10 – 12 Important pharmacological proper-
ties have been attributed to the essential oils of a number
of plants and many aromatic plants are used in traditional
medicine. In the framework of our investigations18 – 21
towards the discovery of pharmacologically important
oils, we report here the chemical composition of H. per-
foliatum from two different geographic localities. To the
best of our knowledge, this is the first report on the
essential oil composition of H. perfoliatum.
Experimental
Collection of Plant Material
Two different populations of H. perfoliatum (five to
seven plants from each population) were collected during
(65 g sample A) was collected in Preveza, Epirus. The
second population (50 g sample B) was collected in
Diminio, Peloponnesos. Voucher specimens are depo-
sited in the Laboratory of Pharmacognosy, University of
Athens, under Accession Mos Couladis 101 (sample A)
and 102 (sample B).
Isolation of the Essential Oils
Air-dried plant material was subjected to hydrodistilla-
tion using a Clevenger-type apparatus for 3 h to yield
0.30% and 0.20% of yellowish oils of samples A and B,
respectively.
Gas Chromatography–Mass Spectrometry
GC–MS analyses were carried out using a Hewlett-
Packard 6890-5973 GC–MS system operating in the
EI mode at 70 eV, using two different columns, an
HP Innowax (30 m ð 0.25 mm, film thickness 0.50 µm)
capillary column and an HP 5MS (30 m ð 0.25 mm,
film thickness 0.25 µm) capillary column. The temper-
ature programme for HP Innowax was 60–260 ° C at a
take of 3 ° C/min, held for 10 min, and for the HP 5MS
it was 60–300 ° C at a rate of 3 ° C/min. Helium was used
as the carrier gas, flow rate 1 ml/min. Split ratio, 1 : 10.
Identification of the Components

The identification of the compounds was based on com-

*Correspondence to: M. Couladis, University of Athens, School of
Pharmacy Department of Pharmacognosy, Panepistimioupolis Zogra- parison of their Kovats indices (KI), their retention
fou 157 71 Athens, Greece. E-mail: kouladi@pharm.uoa.gr times (RT) and mass spectra with those obtained from

Copyright  2001 John Wiley & Sons, Ltd.

 ESSENTIAL OIL OF HYPERICUM PERFOLIATUM 205

Table 1. Composition of the essential oils of Hypericum perfoliatum

Compound RIŁ RIŁŁ Sample A (%) Sample B (%) Identification
n-Nonane 902 1045 8.5 3.3 GC–MS, Co–GC
˛-Pinene 940 1038 48.6 34.2 GC–MS, Co–GC
Camphene 948 1083 0.8 t GC–MS, Co–GC
Verbenene 951 t — GC–MS
ˇ-Pinene 977 1118 3.9 9.2 GC–MS, Co–GC
6-methyl-5-hepten-2-one 985 t — GC–MS
ˇ-Myrcene 990 1163 0.9 1.2 GC–MS, Co–GC
n-Decane 999 1051 t — GC–MS, Co–GC
˛-Terpinene 1008 1189 t — GC–MS, Co–GC
p-Cymene 1022 0.5 — GC–MS, Co–GC
Limonene 1027 1204 1.8 1.7 GC–MS, Co–GC
1,8 -Cineole 1029 1228 t — GC–MS, Co–GC
(Z )-ˇ-Ocimene 1035 1237 t t GC–MS
(E )-ˇ-Ocimene 1040 1256 — t GC–MS
-Terpinene 1056 1247 t — GC–MS, Co–GC
Terpinolene 1087 1279 t t GC–MS, Co–GC
n-Undecane 1101 2.9 3.8 GC–MS
n-Nonanal 1104 0.3 — GC–MS, Co–GC
exo-Fenchol 1112 t — GC–MS
˛-Campholenal 1125 0.3 — GC–MS
trans-Pinocarveol 1136 t — GC–MS, Co–GC
Borneol 1163 1689 t — GC–MS, Co–GC
Naphtalene 1179 t — GC–MS
˛-Longipinene 1347 t — GC–MS, Co–GC
Cyclosativene 1362 t — GC–MS
˛-Ylangene 1370 t t GC–MS
˛-Copaene 1375 1494 2.5 2.9 GC–MS
ˇ-Patchoulene 1377 t — GC–MS
(E )-Caryophyllene 1418 1610 1.9 3.8 GC–MS
ˇ-Gurjunene 1423 — t GC–MS
Aromadendrene 1437 0.7 1.8 GC–MS
˛-Humulene 1452 1675 0.7 t GC–MS
allo-Aromadendrene 1459 1660 0.7 3.5 GC–MS
-Muurolene 1477 1690 2.3 6.0 GC–MS
Germacrene D 1481 1713 3.1 1.6 GC–MS
(E )-ˇ-Ionone 1484 1938 t 1.5 GC–MS
Viridiflorene 1494 1698 1.3 3.5 GC–MS
Bicyclogermacrene 1496 t t GC–MS
˛-Muurolene 1499 0.7 2.1 GC–MS
-Cadinene 1513 1765 1.7 3.3 GC–MS
υ-Cadinene 1524 1763 4.6 8.1 GC–MS
Cadina-1,4-diene 1532 t t GC–MS
˛-Cadinene 1536 t t GC–MS
˛-Calacorene 1542 1920 0.8 1.1 GC–MS
(Z )-3-hexenyl-benzoate 1570 t t GC–MS
Spathulenol 1577 2149 1.0 3.0 GC–MS, Co–GC
Caryophyllene oxide 1582 2000 2.2 3.5 GC–MS, Co–GC
1-epi -Cubenol 1627 0.5 t GC–MS
Cubenol 1641 0.6 — GC–MS
˛-Muurolol 1646 t t GC–MS, Co–GC
˛-Cadinol 1654 0.4 — GC–MS
Cadalene 1674 0.8 — GC–MS
Identification: (%) (%)
Monoterpene hydrocarbons 56.5 46.3
Oxygenated-monoterpenes 0.3 0
Sesquiterpene hydrocarbons 21.8 37.7
Oxygenated sesquiterpenes 4.7 6.5
Others 11.7 8.6
Total identified 95.0 99.1

RI Retention Indices relative to C9 –C24 n-alkanes on the HP-5MSŁ column and on the HP Innowax capillary columnsŁŁ .23
Sample A, Preveza; sample B, Diminio.
GC–MS D identification based on comparison of mass spectra.
Co–GC D retention time identical to authentic compounds.
%, Relative percentage obtained from peak area.
t D< 0.01.

Copyright  2001 John Wiley & Sons, Ltd. Flavour Fragr. J. 2001; 16: 204–206
206 M. COULADIS ET AL.
authentic samples and/or the NIST/NBS, Wiley libraries
and the literature.22
Results and Discussion
The complete chemical composition of the oil sam-
ples is summarized in Table 1. Fifty components were
identified from the plant material collected in Preveza
(sample A), amounting to 95.0% (area percent) of the
total oil. The monoterpene hydrocarbons had the high-
est contribution (56.5%). This fraction was dominated
by ˛-pinene (48.6%). The sesquiterpene hydrocarbons
represented 21.8% of the total oil, υ-cadinene 4.6%
being the major component. The oxygenated monoter-
penes fraction was relatively poor; it represented 0.3%
of the total oil. The oxygenated sesquiterpenes consti-
tuted 4.7%, caryophyllene oxide (2.2%) being the major
constituent of this fraction.
Thirty-three constituents were identified from the plant
material collected in Diminio (sample B), amounting to
99.1% of the total oil. The monoterpene hydrocarbons
formed the main fraction, amounting to (46.3%) of the
oil; ˛-pinene (34.2%) and ˇ-pinene (9.2%) were the
major components. The sesquiterpene hydrocarbon frac-
tion richer than that of the oil sample A, constituted 37.7%
of the total oil; -muurolene (6.0%) and υ-cadinene (8.1%)
werethemaincomponents,whiletheoxygenatedsesquiter-
penes amounted to 6.5% of the total oil, caryophyllene
oxide (3.5%) again being the major component.
Both oils were similar regarding the qualitative pattern
but displayed some quantitative differences. The concen-
tration of monoterpene hydrocarbons in the oil of sam-
ple A was higher than that of sample B. The oil of sam-
ple B was richer in sesquiterpene hydrocarbons (37.7%)
than the oil of sample A (21.8%). Both oils isolated
from H. perfoliatum showed that the major component
was ˛-pinene, in agreement with literature reports on the
essential oils of other Hypericum species.9 – 12
Copyright  2001 John Wiley & Sons, Ltd.
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