1560 CHEMISTRY & BIODIVERSITY – Vol.

8 (2011)

Chemical Composition of the Leaf and Flower Essential Oils of Tunisian

Lavandula dentata L. (Lamiaceae)
by Bechir Touati* a ) d ), Hnia Chograni b ), Imed Hassen c ), Mohamed Boussad b ), Lamjed Toumi d ), and
Nadia Ben Brahim a )
a
) Laboratory of Botany and Ornamental Plants, National Institute of Agronomical Research of Tunisia,
Street of Heddy Karry, 2049, Ariana, Tunisia (e-mail: touatibechirl@yahoo.fr)
b
) Laboratory of Plant Biotechnology, National Institute of Applied Science and Technology, Tunisia
c
) Unit of Physicochemical Research Studies of Substances and Natural Mediums, National Institute of
Research and Physicochemical Analysis, Tunisia
d
) Laboratory of Genetic and Forester Plant, Forestry and Pastoral Institute of Tabarka, Tunisia

Essential oils of Lavandula dentata, a Tunisian native plant, were isolated from leaves and flowers by
hydrodistillation in a Clevenger-type apparatus and characterized by GC-FID and GC/MS analyses. The
average essential oil yields, means of five replicates, were higher for the flowers (8.60 mg/g) than for the
leaves (6.56 mg/g). A total of 72 compounds were identified, accounting for 98.1 and 97.7% of the total oil
composition of the leaves and flowers, respectively. The main essential oil constituents were 1,8-cineole,
camphor, and l-fenchone, accounting for 33.54, 18.89, and 8.36% in the leaf oils and for 19.85, 23.33, and
7.13% in the flower oils, respectively. Besides this quantitative variation, the results also showed
considerable qualitative variation between the essential oils of the two plant parts analyzed. These
differences might be adaptative responses to ecological exigencies.

Introduction. – The genus Lavandula (Lamiaceae) includes 38 species known for

their aromatic and medicinal properties and their high yield of essential oil [1]. The
genus is endemic to the Mediterranean region, the Arabian Peninsula, the Canary
Islands, and India. However, many Lavandula species are now cultivated all over the
world, not only for their therapeutic purposes and their economic values, but also for
ornamental and decorative uses.
Lavandula species are of great interest due to their content of essential oil, which is
important in the perfume, cosmetic, flavoring, and pharmaceutical industries [2 – 4].
Recent studies have reported their value as a medicinal plant, and the pharmacological
effects of their essential oil have been revealed as antioxidant, antimutagenic,
antiplatelet, antithrombotic, anticonvulsant, anxiolytic, anti-inflammatory, and analge-
sic [5 – 11].
The chemical composition of Lavandula species has been widely investigated, and it
varied according to the part of the plant analyzed [12] [13], the method of extraction
[14] [15], the genetic determination, and the environmental factors [16], but above all
according to the species. Thus, the essential oils of Lavandula species showed many
chemotypes. L. angustifolia was found to produce a higher quality of essential oil due to
the richness in linalyl acetate (43.1%) and linalool (32.7%) [6]. The essential oil
isolated from the leaves of L. latifolia was mainly composed of 1,8-cineole (46.8 –

 2011 Verlag Helvetica Chimica Acta AG, Zrich

 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011) 1561

54.6%) and camphor (31.5 – 43.5%), while the major components of the flower oil were
linalool (15.1 – 54.7%), 1,8-cineole (20.8 – 47.9%), and camphor (11.4 – 18.6%) [16]. L.
stoechas oils have been studied in different Mediterranean countries and showed
diverse compositions. Despite their quantitative variation, the major components of the
essential oils isolated from the leaves and flowers of this species were in foremost cases
fenchone, 1,8-cineole, and camphor [12] [17] [18].
A study of the chemical composition of L. luiseri oil showed that 2,3,4,4-
tetramethyl-5-methylenecyclopent-2-enone, 1,8-cineole, and camphor were the major
components [13] [19], while L. canariensis oil from the Canary Islands was mainly
composed of carvacrol (23.6 – 42.6%), b-bisabolene (7.5 – 20.8%), (E,E)-a-farnesene
(9.1 – 11.3%), carvacrol methyl ether (4.6 – 7.3%), and cis-hex-3-en-1-ol [20].
Previous phytochemical reports showed that the essential oil of L. dentata leaves
was rich in 1,8-cineole, accounting for 75% of the total oil [21]. Similar studies on the
same species native to Algeria showed that the main constituents were 1,8-cineole
(38.4%), cis-verbenol (4.3%), p-cymen-8-ol (3.8%), and fenchone (2.3%) [22]. In a L.
dentata leaf essential oil from Morocco, linalool (28.9%), linalyl acetate (43.5%), p-
cymene (9.6%), and camphor (2.3%) were the main components [23]. Nevertheless,
this species has received little attention, and previous studies have been focused mainly
on the essential oil isolated from the leaves, while, to our knowledge, no published data
is available on the composition of the flower oil.
In Tunisia, the genus Lavandula is represented by three species, L. stoechas, L.
multifida, and L. dentata. The latter species vanished from many parts of the country,
and only one cultivated population is still preserved in the research field of the National
Institute of Agronomical Research of Tunisia. Therefore, an investigation of this
genetic resource was needed for the assessment of its biochemical values. Thus, as a part
of our phytochemical investigation and genetic resource valorization of Tunisian
aromatic and medicinal plants, the chemical composition of the essential oils extracted
from the leaves and flowers of Tunisian native L. dentata, characterized by GC-FID and
GC/MS analyses, is reported.

Results and Discussion. – Essential Oil Yield. The average L. dentata essential oil
yields were 6.56 mg/g (dry weight) for the leaves and 8.60 mg/g (dry weight) for the
flowers. Therefore, the inflorescences produced a ca. 32.4% higher essential oil yield
than the leaves. Such differences were reported earlier for L. stoechas, whose flowers
contained ca. 60% more essential oil than the leaves, and also for L. latifolia [12] [16].
Identified Compounds and Their Variation According to the Plant Part. The contents
in percent of the constituents of the essential oils isolated from the leaves and
inflorescences are reported in Table 1. In addition to the difference in the essential oil
yield, the GC-FID and GC/MS analyses revealed qualitative and quantitative
differences in the composition between the oils of the two plant parts. The flower
essential oil was more complex, as 69 components were identified, representing 97.7%
of the whole volatile fraction, while 60 components, representing 98.1% of the total oil
composition, were identified in the leave oil.
Considering the fact that minor components of the essential oils are less important
for a comparison, only the major components, representing more than 3% of the
essential oil composition, are reported in Fig. 1, which illustrates the variation of the
1562 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011)

contents of those components between the flower and the leaf oils. 1,8-Cineole was the
major compound identified in the leaf oil (33.54%), whereas it represented 19.85% in
the flower oil. Moreover, the leaf oil contained more l-fenchone than that of the
inflorescences (8.36 vs. 7.13%). Alternatively, camphor was the major compound of the
flower oil (23.33%), with a content considerably higher than that found in the leaf oil
(18.89%).

Fig. 1. Quantitative variation of the contents of the main components between the leaf and flower oils of
Lavandula dentata

Comparative statistical analysis between the leaf and flower oils showed that the
variation of the quantity of the main components was significant for the major
compounds 1,8-cineole and camphor, but insignificant for the other main components,
i.e., l-fenchone, d-fenchyl alcohol, b-eudesmol, and b-selinene (8.36, 4.10, 3.46, and
3.01% in the leaves vs. 7.13, 4.04, 2.88, and 2.98% in the flowers, resp.).
In addition to the quantitative variations, there were also qualitative differences,
illustrated by the presence of some components in one of the oils that were not detected
in the other oil. Indeed, the leaf essential oil was characterized by the presence of
camphenilone, 4,7-dimethyl-1-tetralone, and a-cadinol, while the flower oil was
distinguished by the presence of hexan-1-ol, hexyl butyrat, isobornyl formate, cis-
carveol, hexyl 2-methylbutyrate, (Z)-hex-3-enyl tiglate, hexyl caproate, cis-b-farne-
sene, trans-b-farnesene, caryophyllenol II, longiverbenone, and phytone.
Principal Components Analysis (PCA). The chemical compositions of the leaf
essential oils of L. dentata from three North African regions, i.e., Tunisia (results of the
present study), Algeria [22], and Morocco [23], were subjected to PCA, to identify
which constituents allow to differentiate the populations from these countries. The
PCA was performed with the essential oil constituents that showed an average
percentage equal to or higher than 2.3% in at least one of the populations, i.e., 1,8-
cineole, fenchone, cis-verbenol, camphor, p-cymen-8-ol, l-fenchone, linalool, p-
cymene, and linalyl acetate (Table 2).
The PCA showed that the first two principal axes accounted for 92.739 and 7.261%
of the total variance, respectively. The plot established according to these two PCA
axes (Fig. 2) shows two distinct groups of essential oils. The oils of Group I, formed by
the populations from Algeria (Population A) and Tunisia (Population T) were rich in
 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011) 1563

Table 1. Composition of the Essential Oils Isolated from the Leaves and Inflorescences of Lavandula
dentata

Constituents RIHP-INNOWAX a ) RIHP-5MS b ) Content [%] F-Test c )

Leaf oil Fower oil
Hexan-1-ol 858 1345 – 0.152 207.03**
a-Pinene 923 1016 0.61 0.441 0.86ns
Camphene 937 1057 0.425 0.215 198.45**
b-Pinene 964 1103 1.942 1.376 144.16**
Oct-1-en-3-ol 971 1446 0.090 0.140 57.76**
p-Cymene 1016 1259 0.473 0.258 208.01**
d-Limonene 1022 1194 0.448 1.078 178.61**
1,8-Cineole 1022 1205 33.539 19.851 84.31**
cis-Thujan-4-ol 1057 1531 0.073 0.174 45.90**
cis-Linalool oxide 1064 1428 0.303 0.127 13.94**
Camphenilone 1072 1431 0.087 – 6.76**
l-Fenchone 1078 1378 8.356 7.131 67.53**
trans-Linalool oxide 1080 1456 0.260 0.209 11.70**
trans-Thujan-4-ol 1090 1459 0.058 0.098 7.20**
Linalool 1095 1542 0.678 0.483 17.11**
d-Fenchyl alcohol 1105 1570 4.096 4.039 14.62**
a-Campholenal 1117 1473 0.286 0.221 19.01**
Norinone 1126 1542 0.664 0.512 10.40**
trans-Pinocarveol 1129 1629 2.077 2.643 144.16**
Camphor 1134 1492 18.890 23.331 175.98**
cis-Verbenol 1135 1634 0.333 0.239 39.76**
trans-Verbenol 1136 1657 1.250 1.584 50.20**
Pinocarvone 1151 1536 0.670 0.772 98.24**
l-Borneol 1155 1680 1.446 2.072 176.34**
a-Terpieol 1157 1652 0.976 0.725 28.35**
4-Terpineol 1167 1584 0.423 1.064 184.90**
Melilotal 1175 1736 0.073 0.216 92.02**
Cryptone 1176 1629 0.227 0.720 109.37**
p-Cymen-8-ol 1177 1826 0.481 0.489 2.88ns
a-Terpineol 1181 1654 0.578 0.816 254.90**
Myrtenal 1185 1597 0.989 1.125 83.23**
Myrtenol 1187 1768 1.143 1.682 130.73**
Hexyl butyrate 1189 1410 – 0.331 98.41**
Isoverbenone 1198 1665 0.305 0.385 28.80**
trans-Carveol 1210 1810 0.364 0.443 28.08**
Isobornyl formate 1217 1810 – 0.120 12.89**
cis-Carveol 1222 1846 – 0.102 93.03**
Cuminaldehyde 1229 1744 0.203 0.360 11.09**
Carvone 1233 1701 0.331 0.563 24.22**
Hexyl 2-methylbutyrate 1238 1422 – 0.130 0.01*
Phellandral 1262 1718 0.075 0.112 61.61**
Cuminol 1282 2070 0.277 0.336 15.66**
Perillic alcohol 1289 1976 0.148 0.141 2.21**
( Z )-Hex-3-enyl tiglate 1318 1653 – 0.127 14.44**
Hexyl tiglate 1325 1606 0.145 0.503 57.67**
Hexyl caproate 1381 1604 – 0.130 15.13**
Caryophyllene 1404 1624 0.115 0.476 58.64**
1564 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011)

Table 1 (cont.)
Constituents RIHP-INNOWAX a ) RIHP-5MS b ) Content [%] F-Test c )
Leaf oil Fower oil
a-Bergamotene 1425 1661 0.070 0.337 32.08**
cis-b-Farnesene 1433 1624 – 0.116 12.04**
b-Selinene 1470 1688 3.010 2.981 15.49**
trans-b-Farnesene 1472 1661 – 0.245 53.88**
a-Selinene 1479 1692 0.052 0.094 7.94**
b-Bisabolene 1498 1703 0.269 0.795 12.45**
d-Cadinene 1501 1724 0.191 0.593 72.72**
l-Calamenene 1507 1799 0.327 0.685 57.67**
4,7-Dimethyl-1-tetralone 1525 2174 0.187 – 31.36**
cis-a-Bisabolene 1533 1755 0.113 0.239 7.14**
Caryophyllene oxide 1565 1932 1.554 3.446 161.10**
Cubenol 1598 2014 0.117 0.163 9.52**
b-Eudesmol 1632 2189 3.455 2.883 147.23**
Bisabolol oxide B 1639 2094 0.298 0.512 20.61**
a-Cadinol 1642 2196 0.128 – 14.67**
8-Oxoneoisolongifolene 1644 2271 0.618 0.628 4.50**
a-Calacorene 1652 1878 0.196 0.207 5.45**
Caryophyllenol II 1655 2328 – 0.157 22.09**
Cadalene 1658 2176 0.288 0.367 28.08**
trans-Longipinocarveol 1662 2364 0.151 0.179 3.53**
14-Norcadin-5-en-4-one isomer B 1666 2210 1.136 1.286 10.13**
a-Bisabolol 1670 2192 0.450 0.951 112.95**
Longiverbenone 1713 2233 – 0.270 65.45**
cis-b-Santalol 1735 2402 1.513 1.949 85.54**
Phytone 1836 2423 – 0.382 131.10**
Total identified 98.133 97.703
a
) Retention indices ( RIs) determined relative to n-alkanes on the HP-INNOWAX capillary column.
b
) Retention indices determined relative to n-alkanes on the HP-5MS capillary column. c ) F-Test of the
variance analysis ( F 38/150 degrees of freedom): **, highly significant at P < 0.001; *, significant at
P < 0.01; ns, not significant at P > 0.05%.

1.8-cineole (38.4 and 33.5%, resp.). However, these oils differ by their concentrations
in camphor, since the Tunisian oil contained a high concentration (18.9%), while the
Algerian oil had a low content (1.6%) of this compound. Conversely, the oil of Group
II, composed by the population from Morocco (Population M), was characterized by
the lowest percentage of 1.8-cineole (2.0%), a low to intermediate concentration of
camphor (2.3%), and high concentrations of linalool (28.9%) and linalyl acetate 43.5%
(Table 2).
Briefly, the PCA classified the Tunisian and Algerian L. dentata leaf oils, both
characterized by the predominance of 1.8-cineole as major compound, into the same
group (Group I) and emphasized the distinctiveness of the Moroccan oil, rich in
linalool and linalyl acetate. Alternatively, despite their intra- and interspecific
variations, 1.8-cineole and camphor have been found to be present in higher amounts
in the essential oils of many other Lavandula species (Table 3), which is in good
 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011) 1565

Table 2. Comparison of the Contents of the Main Components of the Essential Oils of Lavendula dentata
from Three North African Populations

Main Components Content [%] a )

Tunisian L. dentata Algerian L. dentata Moroccan L. dentata
1,8-Cineole 33.54 38.40 2.00
Fenchone – 2.30 –
cis-Verbenol 0.33 4.30 –
Camphor 18.89 1.60 2.30
p-Cymen-8-ol 0.48 3.80 –
l-Fenchone 8.36 – –
Linalool – – 28.90
p-Cymene – – 9.60
Linalyl acetate – – 43.50
a
) The contents of the main components of the Tunisian, Algerian, and Moroccan L. dentata essential oils
were taken from the present study (leaf oil), Dob et al. [22] (oil isolated from the aerial parts), and
Bouchra et al. [23] (oil isolated from the aerial parts), respectively.

Fig. 2. Plot of the first two principal components (F1 and F2 ) for the PCA of the main essential oil
components of three Lavandula dentata populations from North Africa. The eigenvalues for each
principal component are given in parentheses. Population codes: T, Tunisian essential oil characterized in
this study; A, Algerian essential oil (data from [22]); M, Moroccan essential oil (data from [23]).

agreement with our findings for L. dentata. However, the chemical composition of the
essentials oils isolated from the flowers of L. dentata was reported for the first time and
provided data about the qualitative and quantitative constitution pattern of this
essential oil.
Overall, the quantitative and qualitative chemical composition of the essential oils
presented herein differed greatly between the leaves and flowers and the different
regions of origin of the same species. This tendency, which translates the complexity of
the secondary metabolism of this species, was obviously confirmed in other species
 1566 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011)

Table 3. Comparison of the Yields and Main Components of the Essential Oils Isolated from Different Lavendula
Species

Species Origin Plant part Yield [% (w/w)] Main components Reference

Compound name Content [%]
L. dentata Tunisia Leaves 0.66 1,8-Cineole 33.5 This work
Camphor 18.9
l-Fenchone 8.4
Flowers 0.86 1,8-Cineole 19.9
Camphor 23.3
l-Fenchone 7.1
L. dentata Algeria Aerial parts 0.79 1,8-Cineole 38.4 [22]
cis-Verbenol 4.3
p-Cymen-8-ol 3.8
L. dentata Morocco Aerial parts 0.70 Linalyl acetate 43.5 [23]
Linalool 28.9
p-Cymene 9.6
L. canariensis Canary Aerial parts 0.10 Carvacrol 23.6 [20]
Islands
b-Bisabolene 20.8
( E,E )-a-Farnesene 11.3
L. luisieri Spain Leaves 0.23 – 0.86 1,8-Cineole 0.6 – 3.2 [13]
5-Methylene-2,3,4,4- 12.2 – 38.3
tetramethyl-
cyclopent-2-enone
Camphor 1.8 – 3.7
Flowers 0.12 – 0.53 1,8-Cineole 0.4 – 8.3
5-Methylene-2,3,4,4- 5.8 – 14.6
tetramethyl-
cyclopent-2-enone
Camphor 1.8 – 51.8
L. stoechas Cyprus Aerial parts 1.50 – 4.70 Fenchone 35.8 [24]
L. ssp. stoechas
Camphor 18.5
a-Terpineol 12.9
L. stoechas Greece Aerial parts 1.30 Fenchone 30.9 [25]
Pinocarvyl acetate 10.2
Camphor 9.6
L. latifolia Spain Leaves 0.23 – 0.44 1,8-Cineole 46.8 – 4.6 [16]
Camphor 31.5 – 3.5
Flowers 5.49 – 6.61 1,8-Cineole 20.8 – 7.9
Linalool 15.1 – 4.7
Camphor 11.4 – 18.6
L. angustifolia Lithuania Aerial parts – Linalyl acetate 26.5 [4]
Mill.
Linalool 21.0
Lavandulyl acetate 5.5
 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011) 1567

from the genus Lavandula [12] [16]. Thus, previous reports have attributed the chemo-
variation of essential oils among varieties to genetic and environment factors [12] [26 –
30]. However, little is known on the determinism of the chemical diversity between leaf
and flower oils. These differences might be the results of a differential genetic
expression that allows an adaptation process to ecological functions, such as the
attraction of insect pollinators or the repellence of aggressors.

Conclusions. – Tunisian L. dentata occurs in small fragmented habitats. The leaf and
flower oils were dominated by 1,8-cineole and camphor. However, the contents of these
constituents differed according to the plant part. Thus, quantitative and qualitative
differences between the essential oils isolated from the leaves and flowers have been
revealed. According to the plant part and the dominant compounds, two chemotypes
could be distinguished in Tunisian L. dentata oils, a 1,8-cineole (33.54)/camphor (18.89)
chemotype for the leaves, and a camphor (23.33)/1,8-cineole (19.85) chemotype for the
flowers. These variations might be a response of the species to environmental
conditions.

Experimental Part
Plant Material. The leaves and inflorescences of L. dentata L. were collected in March 2008,
corresponding to the flowering stage, from cultivated plants in the research field of the National Institute
of Agronomical Research of Tunisia. The plant material was botanically characterized by Dr. N. B. B.
(Laboratory of Botany and Ornamental Plants, National Institute of Agronomical Research of Tunisia)
according to the morphological description presented in the Tunisian Flora [31].
Isolation of Essential Oils. The leaves and flowers were air-dried (for 30 d) at r.t. in a shady place,
protected from direct light. Each sample was powdered and mixed to ensure sample uniformity. The
essential oils were obtained by hydrodistillation for 3 h of ca. 100 g (dry weight) of plant material using a
Clevenger-type apparatus. The hydrodistillations were done in five replicates, and the oils were stored at
48 until analysis by GC and GC/MS. The average oil yields were estimated on the basis of the dry weight
of the plant material.
GC Analysis. The GC-FID analyses were carried out with an Agilent 6980 Series II apparatus
equipped with a flame ionization detector (FID) and a HP-INNOWAX cap. column (30 m  0.25 mm
i.d., film thickness 0.25 mm). The oven temp. was programmed rising from 50 to 2508 at 88/min and then
held isothermal at 2508 for 10 min; injector temp., 2208; detector temp., 2808; carrier gas, He (2.0 ml/
min). The samples (2 ml) were injected using a split sampling technique.
GC/MS Analysis. The oils were analyzed with a Hewlett-Packard 6890N/5975B inert GC-MSD
system (Agilent, USA) equipped with two cap. columns, a HP-INNOWAX (30 m  0.25 mm i.d., film
thickness 0.25 mm) and a HP-5MS (30 m  0.25 mm i.d., film thickness 0.25 mm) column (J&W Scientific,
USA). The oven temp. was programmed isothermal at 508 for 1 min, then rising from 50 to 2508 at 28/
min, and finally held isothermal at 2508 for 15 min; injector temp., 2508; ion source temp., 2308; carrier
gas, He (high purity, 99.99%; 1.2 ml/min); injection volume, 0.2 ml; split ratio, 100 : 1. The electron impact
ionization mode was used with an ionization voltage of 70 eV. Total ion chromatograms were obtained
over the scan range of 30 – 800 amu in the full-scan acquisition mode, and the compounds were identified
using the NIST05 and Wiley 7 databases with a resemblance percentage above 85%.
Semi-quant. data were calculated from the GC peak areas without using correction factors and were
expressed as relative percentage (peak area %) of the total volatile constituents identified. Retention
indices (RI) were determined for all the detected compounds rel. to the retention times (tR ) of a
homologous series of n-alkanes (C8 – C30).
Compound Identification. The components of the essential oils were identified by comparison of
their EI mass spectra with those of the Wiley-275 library, or with those of authentic compounds, and
1568 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011)

confirmed by comparison of their RI with those of authentic compounds or with the corresponding data
published in the literature [30] [31]. Further confirmation was obtained from the Kovats indices
generated by a homologous series of n-alkanes (C9 – C28 ) on a HP-5MS column.
Statistical Analysis. The percentage of each constituent in the oils of each plant part (PL, percentage
in the leaves; PF, percentage in the flowers), at the species level was
N 
P
PL (or PF) ¼ P /n,
1

where n is the number of repetitions. The variation of the constituents according to the plant part was
assessed by a variance analysis (ANOVA) [32], according to the equation Xik ¼ m þ ai þ Dik , where Xik is
the compound variable, m the overall mean for the leaves or inflorescences, ai the plant part effect, and
Dik the residual effect within the two plant parts. The significance of the F-test was estimated at the P <
0.01 and P < 0.001 levels.
The chemical population structure was assessed by a principal component analysis (PCA) performed
on the contents of the identified constituents for all populations, using the multi-variate statistical
package (MVSP) ver. 3.1 [32]. An UPGMA based on the matrix of pairwise squared Euclidean distances
among the populations was also constructed, to estimate the divergence among the populations [32]. The
Euclidean distance between the population pairs was calculated as D2(i,i’) ¼ S(xij  xi’j)2, where xij and
xi’j are the values of the j th variable of the populations i and i’ [32].

REFERENCES
[1] D. A. Chaytor, J. Linn. Soc., Bot. 1937, 51, 153.
[2] M. H. Boelens, Perfum. Flavor. 1995, 20, 23.
[3] E. A. Weiss, in Essential Oil Crops, CAB International, New York, 1997, p. 600.
[4] P. R. Venskutonis, A. Dapkevicius, M. Baranauskiene, J. Essent. Oil Res. 1997, 9, 107.
[5] Ì. GlÅin, İ. G. Şat, Ş. Beydemir, M. Elmastaş, . İ. Kfrevioğlu, Food Chem. 2004, 87, 393.
[6] M. G. Evandri, L. Battinelli, C. Daniele, S. Mastrangelo, P. Bolle, G. Mazzanti, Food Chem. Toxicol.
2005, 43, 1381.
[7] V. Ballabeni, M. Tognolini, M. Chiavarini, M. Impicciatore, R. Bruni, A. Bianchi, E. Barocelli,
Phytomedicine 2004, 11, 596.
[8] A. H. Gilani, N. Aziz, M. A. Khan, F. Shaheen, Q. Jabeen, B. S. Siddiqui, J. W. Herzig, J.
Ethnopharmacol. 2000, 71, 161.
[9] D. Shaw, J. M. Annett, B. Doherty, J. C. Leslie, Phytomedicine 2007, 14, 613.
[10] S. Sosa, G. Altinier, M. Politi, A. Braca, I. Morelli, R. Della Loggia, Phytomedicine 2005, 12, 271.
[11] V. Hajhashemi, A. Ghannadi, B. Sharif, J. Ethnopharmacol. 2003, 89, 67.
[12] M. Skoula, C. Abidi, E. Kokkalou, Biochem. Syst. Ecol. 1996, 24, 255.
[13] A. González-Coloma, D. Martn-Benito, N. Mohamed, M. C. Garca-Vallejo, A. C. Soria, Biochem.
Syst. Ecol. 2006, 34, 609.
[14] A. R. Fakhari, P. Salehi, R. Heydari, S. N. Ebrahimi, P. R. Haddad, J. Chromatogr., A 2005, 1098, 14.
[15] N. S. Kim, D. S. Lee, J. Chromatogr., A 2002, 982, 31.
[16] J. Munŏz-Bertomeu, I. Arrillaga, J. Segura, Biochem. Syst. Ecol. 2007, 35, 479.
[17] N. Bouzouita, F. Kachouri, M. Hamdi, M. M. Chaabouni, R. Ben Aissa, S. Zgoulli, R. Thonart, A.
Carlier, M. Marlier, G. C. Lognay, J. Essent. Oil Res. 2005, 17, 584.
[18] E. S. Giray, S. Kırıcı, D. A. Kaya, M. Trk, . Sçnmez, M. İnan, Talanta 2008, 74, 930.
[19] J. Sanz, A. C. Soria, M. C. Garca-Vallejo, J. Chromatogr., A 2004, 1024, 139.
[20] J. Palá-Paúl, J. J. Brophy, R. J. Goldsack, B. Fontaniella, Biochem. Syst. Ecol. 2004, 32, 55.
[21] M. J. Gàmez, J. Jiménez, C. Navarro, A. Zarzuelo, Pharmazie 1990, 45, 69.
[22] T. Dob, D. Dahmane, B. Tayeb, C. Chelghoum, Int. J. Aromather. 2005, 15, 110.
[23] C. Bouchra, M. Achouri, L. M. I. Hassani, M. Hmamouchi, J. Ethnopharmacol. 2003, 89, 165.
[24] G. Valentini, N. Arnold, B. Bellomaria, Plant. Med. Phytother. 1993, 224, 289.
[25] E. Kokkalou, Planta Med. 1988, 47, 58.
 CHEMISTRY & BIODIVERSITY – Vol. 8 (2011) 1569

[26] E. Cassel, R. M. F.Vargas, N. Martinez, D. Lorenzo, E. Dellacassa, Ind. Crop. Prod. 2009, 29, 171.
[27] C. Cavaleiro, L. R. Salgueiro, A. P. da Cunha, A. C. Figueiredo, J. G. Barroso, A. Bighelli, J.
Casanova, Biochem. Syst. Ecol. 2003, 31, 193.
[28] K. Ložienė, P. R. Venskutonis, Biochem. Syst. Ecol. 2005, 33, 517.
[29] M. Maksimović, D. Vidic, M. Miloš, M. E. Šolić, S. Abadžić, S. Siljak-Yakovlev, Biochem. Syst. Ecol.
2007, 35, 473.
[30] M. A. Curado, C. B. A. Oliveira, J. G. Jesus, S. C. Santos, J. C. Seraphin, P. H. Ferri, Phytochemistry
2006, 67, 2363.
[31] G. Pottier-Alapetite, Flore de la Tunisie: Angiospermes, Dicotylédones, Apétales-Dialypétales,
I. O. R. Tunisienne, 1981, Vol. 2, p. 654.
[32] SAS Users Guide: SAS STAT, SAS BASIC, version 6, 4th edn., SAS Institute Inc., Cary, NC,
1990.

Received December 14, 2010