FLAVOUR AND FRAGRANCE JOURNAL

Flavour Fragr. J. 2001; 16: 107–109

The essential oil of Micromeria graeca (L.) Bentham et

Reichenb. growing in Greece
O. Tzakou∗ and M. Couladis
Department of Pharmacognosy, School of Pharmacy, University of Athens, Panepistimioupolis Zografou, 157 71 Athens, Greece
Received 15 March 2000
Revised 6 July 2000
Accepted 27 September 2000

ABSTRACT: The essential oils of Micromeria graeca (L.) Bentham ex Reichenb. collected from two different
locations of Attiki (Greece) Mt Parnes (sample A) and Mt Penteli (sample B), were obtained by hydrodistillation
and analysed by means of GC and GC–MS. Sixty-two constituents were identified. Caryophyllene oxide (17.0%)
and epi-˛-bisabolol (12.8%) were the major constituents of sample A. The main constituents found for sample B
were linalool (18.1%) and ˇ-chamigrene (12.5%). Copyright  2001 John Wiley & Sons, Ltd.
KEY WORDS: Micromeria graeca (L.) Bentham ex Reichenb.; Lamiaceae; essential oil composition; caryophyl-
lene oxide; linalool; epi -˛-bisabolol; ˇ-chamigrene

Introduction Penteli (sample B) at Attiki (Greece) in June 1998. The

Micromeria graeca (L.) Bentham ex Reichenb. (syn. Sat-
ureja graeca L.) is herbaceous perennial species, slightly
aromatic, widely distributed in the Mediterranean area.1,2
According to a recent taxonomic treatment of the
Mediterranean genera of the Lamiaceae,3 Satureja
includes the species previously described as the genera
Acinos, Micromeria, Calamintha and Clinopodium.
Because of this taxonomic treatment, the morphological
differences among these five genera are not sufficiently
clear and this attracted our attention. Moreover, it
seems that the separation of M. graeca into several
subspecies is questioned3 and further study is needed
before reaching definitive conclusions.
Members of the genera Satureja and Micromeria
have been used as remedies for a number of medical
problems.4 – 6 Analyses of several Micromeria species
showed that the plants accumulate terpenoids.5 – 10 There
are few phytochemical works reported in the literature
on M. graeca 11 – 14 and none on the composition of the
oil. In our continuing research on the essential oils of
the plants of Greece, we have investigated the essential
oil of the aerial parts of M. graeca.
Experimental
first population is found in a humid area at an altitude
of 500 m, whereas the second is located in an area with
poor vegetation at 700 m. Dr A. Yannitsaros identified
the plant material; voucher specimens are kept in the
Laboratory of Pharmacognosy, University of Athens
(Reference Nos. OT-29 and OT-30).
Isolation of Oils
Semi-crushed air-dried plant material (mainly leaves and
flowers) was subjected to hydrodistillation for 3 h using
a modified Clevenger-type apparatus to yield 0.58% and
0.23% of yellowish oils for samples A and B, respec-
tively. The oils obtained were dried over anhydrous
sodium sulphate and stored at 4–6 ° C until they were
submitted to GC and GC–MS analysis.
Identification of the Components
The identification of the chemical constituents was based
on comparison of their Kováts indices (KI), retention
times (RT) and mass spectra with those obtained from
authentic samples and/or the NIST/NBS, Wiley libraries
and the literature.15

Plant Material
Aerial parts of wild-growing M. graeca were collected at
the flowering stage from Mt Parnes (sample A) and Mt
*Correspondence to: O. Tzakou, Department of Pharmacognosy,
School of Pharmacy, University of Athens, Panepistimioupolis Zogra-
fou, 157 71 Athens, Greece. E-mail: tzakou@pharm.uoa.gr
Gas Chromatography
Capillary GC was carried out using a Perkin-Elmer
8500 instrument equipped with a Supelcowax 10 column
(30 m ð 0.32 mm i.d.; film thickness 0.25 µm) with
a flame ionization detector. Oven temperature was
programmed as follows: 75 ° C to 230 ° C at 3 ° C/min.

Copyright  2001 John Wiley & Sons, Ltd.

108 O. TZAKOU AND M. COULADIS

Table 1. Composition of the essential oils of Micromeria graeca

Sample Aa Sample Bb
Compound KIŁ KIŁŁ (%) (%)
˛-Pinene 935 1029 3.3 0.9
Camphene 952 1060 t —
Sabinene 975 1121 t t
1-Octen-3-ol 978 — 1.1
ˇ-Pinene 980 1113 1.3 t
3-Octanone 985 t t
2-Octanol 997 1384 1.2 0.8
o-Cymene 1020 — t
p-Cymene 1024 1269 0.5 t
Limonene 1028 1200 1.0 t
1,8-Cineole 1030 1211 t —
Benzene acetaldehyde 1039 t t
(E)-ˇ-Ocimene 1048 — t
-Terpinene 1058 1245 t t
cis-Sabinene hydrate 1067 1450 t t
cis-Linalool oxide 1072 1435 2.2 1.5
trans-Linalool oxide 1088 1462 2.0 1.1
Linalool 1096 1535 9.0 18.1
˛-Thujone 1101 1421 t —
endo-Fenchol 1110 1574 t t
ˇ-Thujone 1112 1441 t —
˛-Campholenal 1125 1485 2.5 1.7
trans-Pinocarveol 1139 1652 4.2 2.2
cis-Verbenol 1140 2.7 1.6
trans-Verbenol 1144 1674 10.4 8.3
Borneol 1162 1696 — t
p-Mentha-1,5-dien-8-ol 1165 1.7 0.7
Terpinen-4-ol 1176 1592 0.9 t
˛-Terpineol 1186 1683 1.0 1.0
Myrtenol 1194 1783 3.3 1.8
Verbenone 1201 1730 0.7 t
trans-Carveol 1215 1780 1.2 t
Cumin aldehyde 1239 t t
Carvone 1242 1713 0.8 t
Eugenol 1354 t —
˛-Copaene 1376 1492 t t
ˇ-Bourbonene 1383 1546 0.9 —
ˇ-Cubebene 1390 1541 t —
˛-Gurjunene 1408 1529 t —
ˇ-Caryophyllene 1418 1599 1.8 1.0
˛-Humulene 1452 t —
(E)-ˇ-Farnesene 1456 1667 t —
allo-Aromadendrene 1459 1660 — 2.8
9-epi-(E)-Caryophyllene 1465 t —
ˇ-Chamigrene 1472 1735 — 12.5
-Muurolene 1475 1695 0.6 —
Germacrene D 1479 1710 0.7 7.5
ˇ-Selinene 1483 1727 — t
Valencene 1489 1721 — 5.9
epi-Cubebol 1492 t —
ˇ-Bisabolene 1509 1724 1.3 —
υ-Cadinene 1521 1761 0.5 t
(E)- -Bisabolene 1530 — 2.2
˛-Calacorene 1540 1916 0.8 —
Selina-3,7(11)-diene 1542 1789 — 1.2
Germacrene B 1553 1.6 —
Germacrene D-4-ol 1572 t —
Caryophyllene oxide 1580 1983 17.0 7.1
Humulene epoxide II 1604 2010 1.9 —
Cubenol 1640 t —
Cadalene 1671 2188 2.2 —
epi-˛-Bisabolol 1683 2547 12.8 5.6
Unknown (1)† 1754 t 9.6
KI, Kováts indices relative to C9 –C24 n-alkanes on the HP-5MSŁ and on the HP InnowaxŁŁ capillary
columns.
a Attiki: Mt Parnes; b Attiki: Mt Penteli.

% relative percentage obtained from peak area.

t D< 0.01.
†
(1) MS data: m/z (%) 218 (81), 203 (43), 185 (15), 175 (61), 161 (82), 147 (96), 133 (70), 121
(77), 107 (72), 91 (100), 79 (66), 67 (50), 55 (55), 41 (64).

Copyright  2001 John Wiley & Sons, Ltd. Flavour Fragr. J. 2001; 16: 107–109

Injector temperature 230 ° C. Detector temperature
280 ° C. Carrier gas, He. Split ratio, 1 : 15.
Gas Chromatography–Mass Spectrometry
GC–MS analyses were carried out using a Hewlett-
Packard 5973-6890 GC–MS system operating in the EI
mode at 70 eV, equipped with a split/splitless injector
(220 ° C), a split ratio of 1 : 10, using two different cap-
illary columns a HP-5MS (30 m ð 0.25 mm; film thick-
ness 0.25 µm) and a HP Innowax (30 m ð 0.25 mm;
film thickness 0.50 µm). The temperature programme for
the first column was 60 ° C to 280 ° C at a take of 3 ° C/min
and for the second 60 ° C to 260 ° C at a rate of 3 ° C/min.
Carrier gas, He; flow rate, 1 ml/min.
Results and Discussion
The percentage composition of the oils is given in
Table 1. Constituents are listed in order of their elu-
tion from the HP-5MS column. Sixty-two components
were identified, accounting for 92.0% of sample A
and 86.6% of sample B. Both the samples contained
mainly oxygenated monoterpenes (42.6% in sample A
and 39.7% in sample B). The main constituents of
this fraction were trans-verbenol (10.4%, 8.3%) and
linalool (9.0%, 18.1%). The oxygenated sesquiterpene
fraction was 33.9% for sample A, with caryophyllene
oxide (17.0%) and epi -˛-bisabolol (12.8%) being the
major compounds, while for sample B the fraction was
22.3%. The oil of sample B was richer in sesquiter-
pene hydrocarbons (33.1%) than sample A (8.2%), with
Copyright  2001 John Wiley & Sons, Ltd.
ESSENTIAL OIL OF MICROMERIA GRAECA 109
ˇ-chamigrene (12.5%) being the dominant constituent.
Due to the frequent occurrence of chemotypes in the
family Lamiaceae, different patterns in the composition
of oils of the same species are common. More investi-
gation on the oil of this taxon is needed to confirm the
indicated infraspecific variability.
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