FLAVOUR AND FRAGRANCE JOURNAL

Flavour Fragr. J. 2001; 16: 201–203

DOI: 10.1002/ffj.978

Essential oils of Hypericum olympicum L. and Hypericum

perforatum L.
Branislav Gudžić,1 Siniša Dordević,2 Radosav Palić3 and Gordana Stojanović3 *
1 D. D. ‘Zdravlje’ Pharmaceutical and Chemical Company, 16 000 Leskovac, Yugoslavia
2 Faculty of Technology, 124 Bulevar Oslobodenja, 16 000 Leskovac, Yugoslavia
3 Department of Chemistry, Faculty of Science, 2 Ćirila and Metodija, 18 000 Niš, Yugoslavia

Received 22 June 2000

Revised 6 November 2000
Accepted 14 November 2000

ABSTRACT: The essential oil of Hypericum olympicum L. was analysed for the first time and was compared
to the essential oil of Hypericum perforatum L. from the same location. Eighteen components were common for
both species. The main components of H. olympicim oil were (E)-anethole (30.7%) and ˇ-farnesene (12.4%), and
for H. perforatum oil they were ˇ-caryophyllene (14.2%) and 2-methyl-octane (13.1%). Copyright  2001 John
Wiley & Sons, Ltd.

KEY WORDS: Hypericum olympicum L.; Hypericum perforatum L.; Hypericaceae; essential oil composition

Introduction Experimental

Herbs belonging to the genus Hypericum L. are very sig-
nificant in pharmacology, particularly H. perforatum.1
The oil maceration extract of H. perforatum flowers was
described in the first London pharmacopoeia (Pharma-
copoeia Londonesis, 1618). A great number of stud-
ies refer to the biologically active components isolated
from H. perforatum: hypericin,2 – 5 pseudohypericin,3,4
hyperforin,6 adhyperforin,7 procyandins,8 xantones9,10
and flavonoids.11 The essential oils are not used inde-
pendently in medicine. This is probably the reason
for the smaller number of studies on the composi-
tion of the essential oil of species belonging to this
genus. The distribution area of H. olympicum L. is lim-
ited to the Balkan12 where it grows in sparse popula-
tions on dry spots and rocky grounds. H. perforatum
is widely spread in Europe, Asia, North Africa, New
Zealand and America.13 Particularly rich deposits of this
herbal species are found in Germany, Ukraine and the
Balkan.
The aim of this paper was to determine the composi-
tion of the essential oil of wild-growing H. olympicum
for the first time and to compare it with the com-
position of H. perforatum essential oil from the same
location.
*Correspondence to: G. Stojanović, Department of Chemistry, Faculty
of Science, 2 Ćirila and Metodija, 18 000 Niš, Yugoslavia. E-mail:
goca@filfak.filfak.ni.ac.yu
The plant material was collected in 1998 on the Rujan
mountain, south-east Serbia, and dried for 10 days in a
cool place. Voucher specimens are deposited in Herbar-
ium Moesicum Doljevac (HMD; H. perforatum, No. 45;
H. olympicum, No. 49). Dried and ground drug was
hydrodistilled for 2.5 h using a Clevenger-type appara-
tus. The oil was extracted from the distillate with ether,
and then dried with anhydrous Na2 SO4 . The solvent was
removed by distillation at atmosphere pressure, and the
pure oil was kept at 4 ° C until analysis.
Identification Procedure
A Varian model 3700 Gas Chromatograph, equipped
with a 60 m ð 0.32 mm fused silica capillary column,
with a 0.3 µm film thickness of PTE-5 and FID was
used for GC measurements. The operating conditions
were as follows: temperature programme 60–285 ° C at
4.3 ° C min and an injector and detector temperature of
250 ° C; the carrier gas was H2 (2 ml/min). GC–MS anal-
yses were performed on a Finigan Mat, model 8230,
equipped with fused silica PTE-5 capillary column,
30 m ð 0.25 mm, film thickness 0.25 µm. The carrier
gas was H2 (2.5 ml/min) with the same temperature
programme as for analytical GC. Constituents were iden-
tified by comparison of their mass spectra to those
from MS libraries (Adams89, Nist92 and Amdis32) and
the results obtained were correlated with calculated and

Copyright  2001 John Wiley & Sons, Ltd.

202 B. GUDŽIĆ ET AL.

Table 1. Chemical composition of the H. olympicum Table 2. Chemical composition of the H. perforatum
L. essential oil L. essential oil

Component Percentage Calculated RIŁ KI15 Component Percentage Calculated RIŁ KI15
Tricyclene 0.7 928 926 2-Methyl-octane 13.1 858 –
2,5,6-trimethyl-hepta-1,3,6- 0.2 953 — n-Nonane 1.4 900 900
triene ˇ-Pinene 2.2 982 980
ˇ-Pinene 0.3 982 980 ˇ-Myrcene 0.3 993 991
Myrcene 0.1 993 991 n-Decane 0.2 1000 1000
˛-Phellandrene t 1008 1005 p-Cymene 0.8 1024 1022
˛-Terpinene t 1020 1018 (E)-ˇ-Ocimene 0.3 1041 1040
p-Cymene t 1027 1026 2-Methyl-decane 7.9 1062 –
Limonene 0.3 1033 1031 p-Cymenene 0.2 1090 1089
Ocimene 0.2 1050 1050 n-Undecane 3.9 1100 1100
Fenchone 0.5 1090 1087 Campholenal 0.1 1126 1125
Undecane 0.3 1100 1100 iso-Nonanol 0.4 1173 1171
-Terpineol t 1178 1177 (E)-Pinocarveol 0.4 1139 1139
Estragole 0.5 1195 1195 Pinocarvone 0.1 1164 1162
Carvone 4.2 1245 1242 4-Terpineol 0.5 1180 1177
(E)-Anethole 30.7 1285 1283 p-Cumen-8-ol 0.2 1185 1183
˛-Cubebene 1.3 1353 1351 ˛-Terpineol 0.3 1191 1189
˛-Ylangene 0.6 1373 1372 Myrtenol t 1195 1194
˛-Copaene 2.7 1378 1376 Carvone 0.1 1243 1242
ˇ-Bourbonene 0.1 1387 1384 Geraniol t 1257 1255
ˇ-Cubebene 0.7 1389 1390 2-Methyl-dodecane 4.5 1267 –
˛-Gurjunene 0.1 1411 1409 (E)-Anethole 0.1 1285 1283
ˇ-Caryophyllene 2.1 1419 1418 n-Tridecane 1.3 1300 1300
ˇ-Gurjunene 1.1 1431 1432 ˛-Longipinene 0.4 1352 1351
Patchoulene 0.5 1440 1456 ˛-Copaene 0.2 1380 1376
Bicyclosesquiphellandrene 1.8 1448 — ˇ-Bourbonene 0.2 1386 1384
˛-Caryophyllene 0.3 1456 1454 ˇ-Caryophylene 14.2 1424 1418
ˇ-Farnesene 12.4 1461 1458 ˇ-Gurjunene 0.2 1436 1432
-Muurolene 7.5 1475 1477 ˛-Himachalene 0.4 1450 1447
Germacrene D 4.3 1481 1480 ˛-Caryophyllene 0.4 1456 1454
Eremophyllene 0.7 1490 1491 ˇ-Farnesene 3.2 1462 1458
˛-Muurolene 1.5 1450 1499 -Muurolene 3.5 1480 1477
˛-Farnesene 0.5 1511 1508 ˛-Farnesene 0.1 1510 1508
-Cadinene 4.2 1515 1513 -Cadinene 0.5 1518 1513
-Bisabolene t 1520 1515 υ-Cadinene 0.5 1530 1524
Calamenene 0.4 1522 1521 Nerolidol 0.8 1570 1564
υ-Cadinene 8.7 1525 1524 3-(Z)-Hexenyl-benzoate 0.5 1572 1570
Cadina-3,9-diene 0.7 1529 – Spathulenol 4.5 1580 1576
Cadina-1,4-diene 0.7 1535 1532 Humulene-epoxide 4.2 1610 1606
Muurola-4,9-diene 0.7 1540 — 1-epi-Cubenol 0.7 1631 1627
˛-Calacorene 0.3 1546 1542 n-Tetradecanol 4.1 1680 1676
Germacrene B 0.7 1560 1556 Benzyl benzoate 0.1 1768 1762
ˇ-Calacorene t 1565 1563 n-Hexadecanol 0.4 1882 1879
Spathulenol 0.4 1580 1576 n-Nonadecane 0.2 1900 1900
(1-epi)-Cubenol 0.1 1630 1627
Ł
˛-Elemene t 1635 — Determined from curve logarithm of corrected retenton time—retention
(epi -˛)-Cadinol 0.2 1642 1640 index.
(epi -˛-Muurolol t 1645 1641 t, Less than 0.1%.
˛-Cadinol 0.5 1658 1653
˛-Bisabolol 0.2 1690 1683
same as for the H. perforatum sample examined and
Ł Determined from curve logarithm of corrected retenton time—retention was very close to content of the leaf essential oil of
index.
t, less than 0.1%.
H. perforatum from India.17
Results of GC and GC-MS are given in Tables 1
and 2. Forty-nine components of H. olympicum oil
Adam’s retention indices.14,15 Area percent was obtained were identified, representing 94% of the oil. The four
electronically from the GC–FID response without the most abundant components [(E)-anethole, ˇ-farnesene,
use of an internal standard or correction factors. υ-cadinene and -muurolene] represented 59.3% of the
oil. The component with the highest content in H. olyim-
Results picum was anethole (30.7%). It was not registered in
the previously examined H. perforatum oil.16 We have
The oil content of the aerial dried parts of H. olympicum found it in a very low level in our H. perforatum
was 0.45% and for H. perforatum 0.32%. Both oils iso- oil (0.1%).
lated were yellow, with a specific odour. The previously Forty-four components of H. perforatum oil were
determined content of the H. perforatum 16 oil was the identified, representing 90.7% of the oil. Most of the

Copyright  2001 John Wiley & Sons, Ltd. Flavour Fragr. J. 2001; 16: 201–203

components were represented in small approximate per-
centages in the oil. Significant amounts of alkanes,
2-methyl-octane (13.1%) and 2-methyl-decane (7.9%),
were observed. ˇ-Caryophyllene was the main compo-
nent in the previously examined oil of H. perforatum16
(48.5%), while it was considerably lower in our H. per-
foratum oil (14.2%) and in H. olympicum (2.1%).
The contents of ˇ-farnesene in the oils of H. olym-
picum L. and H. perforatum L. previously examined
were similar (12.4% and 12.1%), while in our H. per-
foratum sample it was considerably lower (3.2%).
There were 18 common components for the H. olym-
picum L. and H. perforatum L oils. Comparing the
composition of the leaf essential oil of H. perforatum
from India17 and the examined essential oil of the aerial
parts of H. perforatum (leaves, flowers and stems), it can
be seen that:
ž ˛-Pinene was the main component in the oil from
India (67.3%), which was not registered in the oil
from Serbia.
ž ˇ-Caryophyllene was the main component (14.2%) in
the oil from Serbia, while its content in the leaf oil
from India was considerably lower (5.2%).
ž There were 15 common components from the oils
from India and Serbia.
The observed differences in the composition of the
examined essential oils of H. olympicum and H. per-
foratum from the same location are very likely geneti-
cally determined. On the other hand, there are significant
differences in the composition of oils originating from
different populations of the same species.16
Copyright  2001 John Wiley & Sons, Ltd.
ESSENTIAL OILS OF HYPERICUM SPP. 203
Further investigations of the composition and bio-
logical activity of essential oils of a larger number of
different populations of the same species, along with
more data about different species of the genus Hyper-
icum, could be helpful in chemotaxonomy and might
possibly be considered for eventual medical use.
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