134 G.

FIGUÉRÉDO
FLAVOUR ET AL.
AND FRAGRANCE JOURNAL
Flavour Fragr. J. 2006; 21: 134–139
Published online 5 September 2005 in Wiley InterScience (www.interscience.wiley.com). DOI: 10.1002/ffj.1543

Studies of Mediterranean oregano populations.

VIII—Chemical composition of essential oils of
oreganos of various origins
Gilles Figuérédo,1,2 Patrick Cabassu,1,2 Jean-Claude Chalchat1,2* and Bernard Pasquier3
1
Laboratoire de Chimie des Huiles Essentielles, Université Blaise Pascal de Clermont, Campus des Cézeaux, 63177 Aubière,
France
2
AVAHEA, 38 Avenue de Clémensat, 63540 Romagnat, France
3
Conservatoire National des Plantes à Parfum, Médicinales, Aromatiques et Industrielles (CNPPMAI), Route de Nemours, 91490
Milly-la-Forêt, France
Received 19 March 2004; Revised 30 June 2004; Accepted 9 August 2004

ABSTRACT: The essential oils of nine species of oregano (Oreganum calcaratum Jussieu, Oreganum lævigatum Boissier,
Oreganum majorana var. majorana Linné, Oreganum majorana var. tenuifolium L., Oreganum microphyllum Vogel,
Oreganum ramonense Danin, Oreganum rotondifolium Boissier, Oreganum vulgare ssp. virens L., Oreganum vulgare ssp.
vulgare L.) were studied by GC and GC–MS; 134 constituents were identified. Essential oils compositions are generally
close to those described in the literature. This study reveals new compositions. Copyright © 2005 John Wiley & Sons, Ltd.

KEY WORDS: Oreganum calcaratum; Oreganum lævigatum; Oreganum majorana var. majorana; Oreganum majorana var.
tenuifolium; Oreganum microphyllum; Oreganum ramonense; Oreganum rotondifolium; Oreganum vulgare ssp. virens; Oreganum
vulgare ssp. vulgare; Lamiaceae; essential oil composition; p-cymene; limonene; linalool; cis-sabinene hydrate; terpinen-4-ol;
α-terpineol; carvacrol; thymol; sabinene; trans-sabinene hydrate; β -caryophyllene; germacrene-D; spathulenol; caryophyllene oxide

Introduction characteristic constituents. Skoula et al.3 and Karousou6

In previous work we have studied the chemical com-
position of seven species of oregano characterized by
a high level of carvacrol.1 This work concerns nine
species of oregano of Mediterranean origin, grown at the
CNPPMAI from seeds collected in identified populations
(Fontainebleau forest). All these species have been stud-
ied and can be classified in the scheme of Ietswaart.2
Group A includes Oreganum calcaratum Jussieu (sec-
tion Amaracus) and O. rotundifolium Boissier (section
Brevifilamentum). Skoula et al.,3 in a CH2Cl2 extract of
O. calcaratum, identified p-cymene (45.7%), γ -terpinene
(8.6%) and thymol (20.4%), while Baser4 found cis-
sabinene hydrate (21.5%) and linalyl acetate (7.5%) in a
sample of essential oil of O. rotundifolium from Artin,
Turkey.
Group B includes Oreganum microphyllum Vogel (sec-
tion Chilocalix) and Oreganum majorana L. (section
Majorana). O. microphyllum Vogel from Crete was studied
by Gotsiou et al.5 Sixty-six compounds were identified in
the volatile fraction of wild and cultivated fractions, stud-
ied by head-space analysis. cis-Sabinene hydrate (≈30%),
sabinene (≈20%), trans-sabinene hydrate (≈14%), linalool,
p-cymene and γ -terpinene made up 1.4–5.6% of the
* Correspondence to: J. C. Chalchat, Laboratoire de Chimie des Huiles
Essentielles, Université Blaise Pascal de Clermont, Campus des Cézeaux,
63177 Aubière, France.
E-mail: j-claude.chalchat@univ-bpclermont.fr
also found cis- and trans-sabinene hydrate (20–30%) in
this species, accompanied by linalool or terpinen-4-ol.
Arnold et al.7 studied the essential oils of flowers,
leaves and stems of O. majorana L. ssp. tenuifolium from
two regions of Cyprus. cis-Sabinene hydrate, which was
more abundant in the flowers and leaves (24% and 33%)
than in the stems (7%), was accompanied by terpinen-
4-ol (16–21%) and γ -terpinene (8–11%) alongside α-
terpineol, trans-sabinene hydrate and linalool.
An analysis of the essential oil of Oreganum majorana
var. majorana L. from Cuba performed by Pino et al.8
found linalool (16.4%), terpinen-4-ol (17.7%) and thymol
(11.5%) but no carvacrol. This result is close to that
of Charai et al.9 in a study of a Moroccan essential oil
in which linalool (32.7%), terpinen-4-ol (22.3%) and
p-cymene (8.0%) were predominant.
The last four varieties belong to Group C; Oreganum
ramonense (section Campanulaticalix), O. vulgare ssp.
virens Ietswaart and O. vulgare ssp. vulgare Ietswaart
(section Oreganum) and O. laevigatum Boissier (section
Prolaticorolla).
Oreganum ramonense Danin, studied by Danin et al.,10
comes from the Negev desert in Israel. The essential oil
from the leaves, obtained by water distillation and by
trapping with dichloromethane and SPE, showed that
79.5% of the oil was composed of alcohols, among
which were α-terpineol (41.5%), terpinen-4-ol (16.8%),
cis-sabinene hydrate (13.2%) and eugenol (3.6%) in the

Copyright © 2005 John Wiley & Sons, Ltd. Flavour Fragr. J. 2006; 21: 134–139

first case, but by SPE, the main constituents found were
1,8-cineole (17.5%), γ-terpinene (14.7%) terpinen-4-ol
(13.9%), α-terpinene (9.3%) and α-terpineol (6.8%).
Oreganum laevigatum Boissier from Turkey, analysed
by Tücker and Maciarello11 and Baser et al.12 was found
to be composed mainly of bicyclogermacrene (24%
and 38%), germacrene-D (20% and 22%) and β -
caryophyllene (14% and 17%).
A study of Oreganum vulgare ssp. virens Ietswaart,
by Melegari et al.13 (Italy), Chalchat and Pasquier14
(CNPPMAI) and Alves-Pereira and Fernandes-Ferrieras15
(Portugal), revealed markedly different chemical composi-
tions. The main constituents of the Italian oil were linalool
(10.1–70.1%), β -caryophyllene (2.9–18.8%), carvacrol
(<0.1–13.7%), terpinen-4-ol (<0.1–15.5%) and α-terpineol
(<0.1–68.3%); and of the French oil, thymol (3.7–9.6%),
β-caryophyllene (7.2–10.6%), sabinene (6.5–11.8%) and
germacrene D (22.1–25.7%). Oil from Portugal differed
from the others by the presence of greater amounts of the
non-functionalized hydrocarbons δ -elemene (12.9%), β -
caryophyllene (11.1%), α-terpineol (9.2%), germacrene B
(6.6%), (E)-β -ocimene (6.6%) and (Z)-β -ocimene (3.7%).
Oreganum vulgare L. ssp. vulgare from Turkey,
studied by Sezik et al.,16 was composed mainly of
terpinen-4-ol (21%) and germacrene-D (17.8%). Chalchat
and Pasquier17 demonstrated the chemical diversity of the
plant grown at the CNPPMAI; six chemical groups were
discerned in which hydrocarbons predominated. Mockute
et al.18 confirms these results in a study of Lithuanian
samples (β -caryophyllene, 10.8–15.4%; germacrene D,
10.0–16.9%; sabinene, 6.4–14.2%; (Z)-β -ocimene, 6.2–
11.0%; and (E)-β -ocimene, 7.0–11.5%. Lastly, an Indian
oil analysed by Pande and Mathela19 unusually contained
γ -muurolene (62.2%).
Experimental
Plant Materials
Seeds were collected in 1997–1999 at natural sites. They
were sown at the CNPPMAI at Milly-la-Forêt in March
1999, and set out in three replicates of 15 plants in a
Fischer block design. The plants were harvested in full
flower, dried in the shade at ambient temperature in a
ventilated room and extracted by water distillation, using
a Clevenger-type apparatus for 3 h. Specimens of each
species were conserved in the CNPPMAI Herbarium.
GC and GC–MS Analysis
GC
The gas phase chromatography analysis was carried out
using a Delsi DI 200 instrument equipped with a flame
Copyright © 2005 John Wiley & Sons, Ltd.
MEDITERRANEAN OREGANO POPULATIONS. VIII 135
ionization detector and a DB5 column (25 m × 0.25 mm
i.d., film thickness 0.25 µm); split flow rate, 60 ml/min;
carrier gas, nitrogen; temperature programming, 5 min at
50 °C, rising at 3 °C/min to 220 °C; injector and detector
temperatures, 220 °C and 235 °C, respectively.
GC–MS
The essential oil was analysed using a Hewlett-Packard
gas chromatograph Model 6890 coupled to a Hewlett-
Packard MS Model 5873 equipped with an HP5 column
(30 m × 0.25 mm i.d., film thickness 0.25 µm), pro-
grammed from 50 °C (5 min), rising at 5 °C/min to 300 °C
then held for 5 min; carrier gas, helium at 1.1 ml/min;
injection, split mode (1/10); injector and detector tem-
peratures were 250 °C and 280 °C, respectively. Ioniza-
tion was by electron impact at 70 eV; electron multiplier,
2200 V; ion source temperature, 230 °C. Mass spectral
data were acquired in the scan mode in the m/z range
33–450.
Identification was carried out by calculating the reten-
tion indices and comparing mass spectra with those
in data banks; personal, Adams,19 and McLafferty and
Stauffer.20
Results and Discussion
The yields of essential oil, physical and chemical
characteristics and chemical compositions are given
in Table 1. Only two species, O. majorana ssp.
tenuifolium and O. ramonense, gave oils in very interest-
ing yields (6.7% and 8.5%, respectively). A chemical
study of these nine species identified 134 compounds,
53 of which were present only in concentrations of at
most 0.1%.
O. calcaratum Jussieu was characterized by the pre-
sence of p-cymene (12%), γ -terpinene (9.1%), terpinen-
4-ol (3%), geraniol (3.6%), thymol (40.6%), carvacrol
(16.5%) and β -caryophyllene (2.5%). This composition is
quite different from that of the dichloromethane extract
reported by Skoula et al.,3 which contained twice as
much thymol and four times less p-cymene.
The oil of Oreganum rotundifolium Boissier showed
an unusual predominance of β -caryophyllene (15.7%)
and trans-sabinene hydrate (13.7%). Alongside these was
found a large percentage of sesquiterpenes (37.5%),
germacrene-D (8.9%), bicyclogermacrene (7.9%) and
many functionalized sesquiterpenes, caryophyllene oxide
(2.8%), globulol (2.7%) and spathulenol (1.5%). We note
the abundance of terpene derivatives, both functionalized
(borneol, 4.8%, and bornyl acetate, 0.6%) and non-
functionalized (about 20; camphene, 1.6%, and sabinene,
1.4%, being the most abundant). These results are similar
to those obtained by Baser et al.4 The difference lies in
the levels of linalyl acetate (7.5%) and β -caryophyllene
Flavour Fragr. J. 2006; 21: 134–139
136 G. FIGUÉRÉDO ET AL.

Table 1. Chemical composition (%) of nine species of Mediterranean oreganos

Compounds KI A B C D E F G H I

3-Methyl-butanal 678 — tr — — — — tr tr tr
2-Methyl-butanal 682 — tr — — tr — tr tr tr
2-Ethyl furane 700 — — — — — — — — tr
3-Methyl-butane-1-ol 727 — — — — — — — — tr
2-Methyl-butane-1-ol 728 — — — — — — — — tr
Methyl butyrate 769 — tr — — — — — tr tr
Methyl-3-methyl-but-2-enoate 842 — tr — — — — — — —
3,5,5-Trimethyl-cyclopent-2-en-1-one 851 — tr — — — — — — —
(E)-Hex-2-enal 852 — tr — — tr — — tr tr
(Z)-Hex-2-enol 856 — — — — tr — — — tr
Isovaleric acid 864 — tr — — — — — — tr
(E)-Hex-2-enol 865 — — — — — — — — tr
Hexyl formiate 870 — — — — — — — — tr
3-Heptanone 886 — — — — — — tr — tr
2,5-Diethyltetrahydrofurane 896 — — — — — — tr — tr
Tricyclene 922 — tr tr tr tr 0.2 0.1 — tr
α-Thujene 926 0.6 0.2 0.2 0.5 0.4 0.3 0.1 0.2 0.1
α-Pinene 933 0.4 0.3 0.5 0.3 0.5 2.5 0.6 0.7 0.1
Thuja-2,4(10)-diene 944 tr tr — tr — — tr tr tr
Camphene 949 0.2 tr tr 0.3 0.2 4.9 1.6 0.1 0.3
Verbenene 953 — — — — — tr — tr tr
Benzaldehyde 964 tr tr tr — — tr 0.1 — —
Sabinene 972 0.1 8.2 4.9 3.8 6.0 2.8 1.4 16.3 0.2
β -Pinene 977 0.2 0.2 tr 0.1 1.8 0.2 tr 1.0 tr
1-Octen-3-one 978 — — tr — — — — — 0.5
1-Octen-3-ol 986 0.4 1.1 — 0.1 — — 0.1 0.2 —
3-Octanone 987 — — — tr — — 0.4 tr 0.1
Myrcene 990 0.8 2.5 1.1 0.6 0.2 0.9 0.2 0.5 0.3
3-Octanol 1002 — 2.9 — tr tr — 0.1 0.3 tr
p-Mentha-1(7),8-diene 1003 — — tr tr tr tr tr 0.1 —
α-Phellandrene 1006 0.2 tr tr tr tr 0.1 tr tr 0.1
δ -3-Carene 1007 0.1 — — tr — tr tr tr —
Hexyl acetate 1014 — — — — — — tr — —
α-Terpinene 1017 1.0 0.5 0.1 1.4 2.9 1.1 0.1 0.3 0.1
p-Cymene 1029 12.0 2.2 0.2 1.9 0.5 3.5 1.1 2.3 0.2
Limonene 1031 0.4 0.7 14.3 0.8 2.8 3.0 0.6 0.4 0.1
β -phellandrene 1032 tr tr 1.8 — tr tr tr tr tr
1,8-Cineole 1033 tr 0.2 — tr tr tr tr 1.6 tr
(Z)-β -ocimene 1038 tr 3.4 0.1 0.1 1.0 0.1 0.4 1.5 1.5
(E)-β -ocimene 1048 tr 1.5 tr 0.1 0.1 tr tr 0.5 1.1
γ -Terpinene 1062 9.1 0.5 0.5 2.8 4.8 1.6 0.1 0.8 0.2
cis-Sabinene hydrate 1073 tr — — 18.3 3.4 1.7 0.9 — —
Terpinolene 1085 — tr tr 0.6 1.1 0.4 0.1 tr 0.8
cis-Linalool oxide 1088 tr tr tr 1.4 tr — tr tr 0.8
p-Cymenene 1091 tr tr tr tr — — tr tr —
Linalool 1103 — 1.1 2.3 31.2 2.2 0.5 8.5 4.1 76.8
cis-Thujone 1108 0.1 — — — — — — 0.1 —
trans-Sabinene hydrate 1109 tr — — 1.4 36.6 6.4 13.7 — —
trans-Thujone 1119 tr tr tr — — tr — 0.1 —
Octyl acetate 1122 — — — — — 0.8 — — —
cis-p-Menth-2-en-1-ol 1128 — tr 0.7 0.7 0.7 0.7 0.1 0.1 —
trans-Sabinol 1139 — — — — — — — 0.2 —
Camphor 1148 tr — — 0.6 — 0.6 — tr —
trans-p-Menth-2-en-1-ol 1152 — tr 0.2 tr 0.3 tr tr tr —
Sabinacetone 1159 — — — — — — — 0.2 —
Pinocarvone 1164 — — — — 0.7 — — — —
Borneol 1177 — — — 0.1 tr 0.1 4.8 0.3 0.3
Terpinen-4-ol 1184 3.0 4.1 47.1 10.1 11.4 10.1 1.7 4.8 tr
α-Terpineol 1195 tr 0.5 4.6 1.2 16.8 1.2 3.1 1.4 0.3
p-Menth-2-en-8-ol 1208 tr — — tr — tr — — —
trans-Piperitol 1220 — — tr — 0.1 — tr tr —
Nerol 1225 — — — — — — 0.2 — 0.1
Thymol methylether 1231 — — 0.5 0.5 — 0.5 0.1 tr tr
Carvacrol methylether 1239 — tr tr 0.2 — 0.2 0.3 — 0.5
Cuminaldehyde 1245 — — tr — — — — tr —
Linalyl acetate 1249 — — 2.2 0.8 2.6 0.8 tr tr 0.2
Geraniol 1265 3.6 — — 0.1 tr 0.1 tr tr tr
Bornyl acetate 1286 — — — 1.1 tr 1.1 0.6 tr —
Dihydroedulan I 1287 — — — — — — tr — 0.5
Cuminol 1295 1.1 — — — tr — — tr —

Copyright © 2005 John Wiley & Sons, Ltd. Flavour Fragr. J. 2006; 21: 134–139
 MEDITERRANEAN OREGANO POPULATIONS. VIII 137

Table 1. (Continued)

Compounds KI A B C D E F G H I

Thymol 1304 40.6 2.1 1.6 1.4 0.2 1.4 1.1 0.6 0.4
Carvacrol 1312 16.5 24.2 2.7 0.5 0.1 0.5 1.8 1.0 3.7
Bicycloelemene 1330 — — tr — — — tr — tr
α-Cubebene 1347 — tr — 0.1 — tr tr tr —
Eugenol 1358 — tr — 0.1 — 0.1 — — tr
Thymyl acetate 1364 tr tr — — — — tr — —
Carvacryl acetate 1368 tr tr — — — — — — —
α-Copaene 1376 — tr — 0.1 — 0.1 0.1 0.2 tr
Geranyl acetate 1378 — — — tr 0.1 tr — — tr
(Z)-β -Damascone 1378 — — — — — — — — tr
β -Bourbonene 1384 — 0.4 tr 0.1 tr 0.1 0.7 1.9 0.1
β -Cubebene 1387 — tr — 0.1 tr 0.1 0.1 0.1 —
β -Elemene 1389 — tr — 0.2 tr 0.2 0.2 — 0.1
cis-Jasmone 1394 — — — 0.2 tr 0.2 — — —
α-Gurjunene 1407 — tr — 0.1 — 0.1 tr — —
β -Caryophyllene 1422 2.5 4.1 1.8 5.9 1.7 5.9 15.7 10.7 0.9
β -Copaene 1430 — tr — — — — 0.2 0.3 tr
trans-α-Bergamotene 1432 — tr — 0.5 — 0.5 — — tr
(Z)-β -Farnesene 1433 — — — tr — 0.4 — — —
Aromadendrene 1439 — tr — — tr — — 0.1 tr
α-Humulene 1456 — 0.7 0.2 0.4 0.1 0.4 1.6 1.7 tr
allo-Aromadendrene 1460 — tr tr 0.3 tr 0.3 0.2 0.5 tr
α-Patchoulene 1462 — 0.3 — — — — — — —
γ -Muurolene 1474 tr tr — 0.1 — 0.1 — 0.1 tr
Germacrene D 1481 tr 11.8 0.2 0.8 0.1 0.8 8.9 13.4 2.2
(Z,E)-α-Farnesene 1488 — tr — — — — — 0.1 —
Ledene 1491 — — — — tr — 0.1 — tr
Bicyclosesquiphellandrene 1491 — — — — — — — 0.2 —
Valencene 1492 — — — 0.2 — 0.2 — — —
Bicyclogermacrene 1496 — 6.4 — 1.1 1.8 1.1 7.9 1.6 2.9
α-Muurolene 1498 — — tr — — — — — —
α-Bulsenene 1500 — — — 0.1 — 0.1 — — —
(E,E)-α-Farnesene 1502 — 4.7 — — tr — — 1.7 0.1
β -Bisabolene 1507 0.4 0.4 tr — tr — 1.1 0.3 1.9
Germacrene A 1507 — — — 0.4 — 0.4 0.2 — —
γ -Cadinene 1512 tr tr tr 0.4 tr 0.4 0.5 0.1 0.1
δ -Cadinene 1517 tr 1.5 0.2 0.3 tr 0.3 tr 0.9 0.2
cis-Calamenene 1519 — — tr tr — tr tr 0.1 —
β-Sesquiphellandrene 1523 tr tr — 0.1 — tr — — —
α-Cadinene 1536 — tr 0.1 tr — tr tr 0.1 —
(E)-α-Bisabolene 1538 tr 0.8 — — — — 0.1 0.2 0.1
α-Calacorene 1541 — — 0.1 — — — — — —
trans-Nerolidol 1561 — — — 0.1 — 0.1 — — —
β -Calacorene 1562 — — 0.1 — — — — — —
Ledol 1569 — 0.5 — — — — — 0.4 —
Hex-3-enyl benzoate 1571 — tr tr — tr — — — —
Germacrene-D-4-ol 1579 — — — 0.5 — 0.5 — 0.1 —
Spathulenol 1578 — 3.6 1.5 — tr — 1.5 8.6 0.2
Caryophyllene oxide 1584 0.9 — 1.3 0.5 tr 0.5 2.8 5.6 0.1
Globulol 1587 — 0.8 0.1 0.1 — 0.1 2.7 tr 0.1
epi-Globulol 1597 — 0.2 0.1 0.1 — tr 0.5 tr tr
Humulene-1,2-epoxide 1610 tr — 0.1 0.1 — 0.1 0.3 1.2 —
1,10-Diepicubenol 1614 — — — — — — 0.5 tr —
Norcopaanone 1622 — — — — — — — 0.2 —
1-epi-Cubenol 1628 — — 0.2 tr — tr — 0.1 —
Isospathulenol 1631 — — — — — — 0.6 — tr
epi-α-Muurolol 1645 — 1.3 0.5 0.9 tr 0.9 tr tr tr
α-Muurolol 1645 — — — — — — — 0.2 0.1
epi-α-Cadinol 1642 — 0.3 0.1 0.1 tr 0.1 tr 0.9 0.1
α-Cadinol 1656 — 2.2 0.1 0.4 tr 0.4 0.8 1.3 0.1
Intermedeol 1666 — — — 0.3 — 0.3 tr — —
Schyobunol 1697 — — — — — — 1.6 — —
Benzyl benzoate 1785 tr tr — tr — tr — — —
Phytone 1886 tr tr tr tr — tr tr — —
Yield (ml/100 g) dried matter 1.3 0.3 1.9 2.1 6.7 8.3 0.2 0.3 2.8
nD24 1.5088 1.5012 1.4845 1.4805 1.4874 1.4820 1.4893 — 1.4642
d 24
20 — — 0.888 — 0.989 — — — 0.856

A, O. calcaratum; B, O. lœvigatum; C, O. majorana var. majorana; D, O. microphyllum; E, O. majorana var. tenuifolium; F, O. ramonense; G, O.
rotondifolium; H, O. vulgare ssp. vulgare; I, O. vulgare ssp. virens.
tr, traces (0.05% or less).

Copyright © 2005 John Wiley & Sons, Ltd. Flavour Fragr. J. 2006; 21: 134–139
138 G. FIGUÉRÉDO ET AL.
(6.1%); the first was present here only in trace amounts,
while the second was the main constituent.
Linalool was the main constituent (31.2%) in the oil
of Oreganum microphyllum Vogel, accompanied by
92 identified compounds including α-terpinene (1.4%),
sabinene (3.8%), p-cymene (1.9%), γ -terpinene (2.8%),
trans-sabinene hydrate (18.3%), linalool (31.2%) and
terpinen-4-ol (10.1%) and the sesquiterpenes bicyclo-
germacrene (1.1%) and β -caryophyllene (5.9%), Small
amounts of carvacrol methylether (0.2%), thymol (1.5%)
and eugenol (0.1%) were also found. These results are
at variance with those reported by Skoula et al.3 for
dichloromethane extracts and near to those of Karousou6.
The oil of Oreganum majorana L. ssp. tenuifolium was
rich in trans-sabinene hydrate (36.6%), terpinen-4-ol
(11.4%) and α-terpineol (16.8%). Alongside these three
main constituents, we found 25% of terpenes character-
ized by sabinene (6.0%), γ -terpinene (4.8%), cis-sabinene
hydrate (3.4%) and limonene (2.8%). We note the tiny
amount of carvacrol (0.1%). Arnold et al.7 obtained dif-
ferent results.
Oreganum majorana var. majorana L. yielded an
oil characterized by 47.1% terpinen-4-ol, alongside
which were found 13 compounds in amounts greater than
1% (sabinene, 4.9%; β -phellandrene, 1.8%; linalool,
2.3%; α-terpinene, 4.5%; myrcene, 1.1%; carvacrol,
2.7%; and limonene, 14.3%) in large amounts for the
first time. We note the presence of functionalized
terpenes and sesquiterpenes (cis-p-menth-2-en-1-ol, 0.7%;
trans-p-menth-2-en-1-ol, 0.2%; spathulenol, 1.5%; and
caryophyllene oxide, 1.3%). The number of sesquiter-
penes was important; however, β -caryophyllene, the most
abundant, represented only 1.8% of the compounds iden-
tified. These results were only partly consistent with the
results of Vera and Chane-Ming22 (terpinen-4-ol, 38.4%)
and Baser et al.23 (carvacrol, 78.2%). Pino8 obtained dif-
ferent results from Cuban oil (linalool, 16.4%; terpinen-
4-ol, 17.7%; thymol, 11.6%; and γ -terpinene, 8.3%). This
disparity in the results points to the existence of several
chemotypes and argues for sorting the species by variety
or sub-species to obtain consistent results.
The Oreganum ramonense Danin that we analysed dif-
fered from earlier samples by the presence of large
amounts of α-terpineol (21.9%), terpinen-4-ol (15.1%)
and borneol (13.1%). Many terpenes were present,
such as camphene (4.9%), p-cymene (3.5%), sabinene
(2.8%), cis-sabinene hydrate (1.7%), trans-sabinene
hydrate (6.4%) and bornyl acetate (2.6%), and numerous
sesquiterpenes : β -caryophyllene (3.8%), β -bisabolene
(1.0%) and germacrene-D (0.5%). Danin et al.10 have
described same composition in oil from the Negev desert
in Israel.
The oil of Oreganum laevigatum Boissier contained
no strongly predominant components. Carvacrol (24.2%)
was the main constituent. Numerous sesquiterpenes were
present, including germacrene D (11.8%) and bicyclo-
Copyright © 2005 John Wiley & Sons, Ltd.
germacrene (6.4%). In the terpene family (Z)- and
(E)-β -ocimenes (3.4% and 1.5%, respectively) and
sabinene (8.1%) were the most abundant. Lastly, some
functionalized sesquiterpenes, such as spathulenol (3.6%),
α-cadinol (2.2%) and epi-α-muurolol (1.3%) were iden-
tified. These results agree only partly with those of
Tücker and Maciarello11 and Baser et al.12 This work
was hampered by the appearance of numerous hybrids
after the sowing carried out in 1999, indicating that the
prospected population was heterogeneous.
O. vulgare ssp. virens Ietswaart yielded an oil com-
posed principally of linalool (76.8%). Carvacrol, the next
abundant constituent, accounted for only 3.7%. The other
constituents, represented by numerous terpenes, were
dominated by (E)- and (Z)-β -ocimenes (1.5% and 1.1%,
respectively) and terpinolene (0.8%). We found a large
number of sesquiterpenes: bicyclogermacrene (2.9%),
germacrene-D (2.2%), β -bisabolene (1.9%) and β -
caryophyllene (0.9%). These results partly confirm those
of Melegari et al.13 Lastly, the samples we examined in
this work differed from those analysed previously.14,15
The sum of work carried out points to the existence of
several chemotypes in this species: a linalool type, an α-
terpineol type, and a sesquiterpene type in which either
germacrene-D or δ -elemene predominated.
Oreganum vulgare ssp. vulgare, unlike the previous
species, contained non-negligible amounts of function-
alized sesquiterpenes: epi-α-cadinol (0.9%), α-cadinol
(1.2%), humulene-1,2-epoxide (1.2%), caryophyllene
oxide (5.6%) and spathulenol (8.6%). This oil was par-
ticularly rich in the terpene hydrocarbons sabinene
(16.3%), p-cymene (2.3%) and (Z)-β -ocimene (1.5%) and
the sesquiterpene hydrocarbons germacrene-D (13.3%),
β -caryophyllene (10.7%) and β -bourbonene (1.9%).
These hydrocarbons were accompanied by the function-
alized terpenes linalool (4.0%) and terpinen-4-ol (4.8%).
This species has been well studied and, as it grows
native over an extremely wide area, various composi-
tions have been found.16,17,18,19 The levels of func-
tionalized sesquiterpenes were often high, e.g. 20.4%
caryophyllene oxide. O. vulgare ssp. vulgare yielded
an oil in which hydrocarbons predominated, either
terpenes (sabinene, (Z)- and (E)-β -ocimenes), sometimes
functionalized (terpinen-4-ol), or sesquiterpenes (γ -
muurolene, germacrene-D or β -bourbonene), demonstrat-
ing a high degree of chemical variability.
This work made it possible to highlight original
compositions for O. calcaratum, rich in thymol, and
O. majorana var. tenuifolium, rich in trans-sabinene
hydrate. The species O. rotundifolium, O. ramonense and
O. microphyllum have compositions close to those already
described. The study of O. majorana var. majorana, O.
vulgare ssp. virens and O. vulgare ssp. vulgare show and
confirm the existence of many chemotypes. In addition,
the study of O. laevigatum highlights the heterogeneity of
its populations.
Flavour Fragr. J. 2006; 21: 134–139
 MEDITERRANEAN OREGANO POPULATIONS. VIII 139

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