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Essential oil and fatty acid composition of a Tunisian caraway (Carum carvi L.) seed ecotype cultivated under water deficit.

Introduction

Water deficit is considered to be a major environmental factor affecting agriculture productivity worldwide and causing considerable crop yield reductions [1,2]. This is particularly true in the Mediterranean Basin where the climate is typically characterized by high potential evaporation and low rainfall during the growing season. In the case of two agriculturally important Lamiaceae of the Mediterranean area, spearmint (Mentha spicata L.) and rosemary (Rosmarinus officinalis L.), increasing levels of water deficit reduced progressively their biomass, and such a reduction was mainly due to declining photosynthetic rates [3]. Thus, water deficit has a negative effect on plant growth and development of many medicinal and aromatic plants like sweet basil (Ocimum basilicum L.), american basil (Ocimum americanum L.) [4], parsley (Petroselinum crispum Mill.) [5], sage (Salvia officinalis L.) [6] etc.

At the cellular level, it has been shown that, under water deficit, plants undergo various physiological and biochemical modifications including changes in membrane composition [7]. These lasts are mainly constituted by fatty acids which are important in maintaining membrane fluidity, integrity and functionality in front of external changes [8].

Nevertheless, investigations dealing with the water deficit effect on biochemical responses of aromatic and medicinal plants are scarce. Generally, water deficit has a positive effect in the biosynthesis of secondary metabolites, enzyme activities and solute accumulation [9]. Thus, this constraint affects the essential oil yield and composition of various aromatic species belonging to the Apiaceae family [5,10].

Among these species, caraway (Carum carvi L.) is one of the most appreciate spices for its seed essential oil richness and its plethora of biologically active compounds. Indeed, it has been shown that Tunisian caraway essential oil is carvone chemotype [11]. This fact is of great economic interest due to the several applications of carvone in the alimentary and medicinal industries [12]. In addition, the fatty acid composition revealed that Tunisian caraway seed oil is rich in an unusual fatty acid--petroselinic acid --[11] which is of potential industrial significance. Use of this oil may also serve in improving human nutrition and health [13,14].

In a previous work dealing with the water deficit effects on Tunisian caraway seed ecotype collected from the region of Haouaria, we have demonstrated that this constraint induced a significant reduction in growth parameters and fatty acid contents but an increase in the proportions of essential oil constituents [15].

Thus, the objective of this study was to determine the impact of water deficit on essential oil and fatty acid composition of a Tunisian caraway seed ecotype collected from the region of Menzel Temime and to compare the results to those obtained previously with the ecotype Haouaria.

Materials and methods

Plant material and growth conditions

Caraway seeds were collected from cultivated plants in the region of Menzel Temime (northeastern Tunisia; latitude 36[degrees] 46' 56" N; longitude 10[degrees] 59' 15" E, altitude 38 m) on July 2006. The field experiment was carried out in the experimental station of the National Agronomic Institute of Tunis, Tunisia (3 Km northwest Tunis; latitude 36[degrees] 55' N; longitude 10[degrees]11' E; altitude 10 m).

The site was characterized by a semi-arid climate with a mean annual precipitation of 500 mm (mainly during the winter) and an average temperature of 18[degrees]C. The soil has a clayey-loamy texture with pH 7.9 and consisted of 1.4% organic matter, 0.11% nitrogen, 0.034% phosphorus and 0.006% potassium.

Experimental design and water deficit treatment

A completely randomized experimental design was conducted as a three factorial blocs with three replications. In each bloc, three combinations of the caraway ecotype with water regimes were randomly distributed on three experimental plots. Plot area was of 2.8 [m.sup.2]. Seeds were sown directly in the field on March 01, 2007 with a row spacing of 0.4m and by respecting a density of 125 plants [m.sup.-2]. Fertilization consisted of 250, 200 and 100 Kg [ha.sup.-1] of [P.sub.2][O.sub.5], [K.sub.2]O and N respectively, incorporated uniformly into the soil before sowing, and supplemented by 100 Kg [ha.sup.-1] of N brought twice during the crop cycle. Drip irrigation was made with a flow of 3.8 l [h.sup.-1]. Pre-irrigation was done immediately after sowing for uniform emergence and establishment of seedlings before starting the water deficit treatment.

Then, plants were subjected to three different water levels: 100% (control (C)), 50% (moderate water deficit (MWD)) and 25% (severe water deficit (SWD)) of crop evapotranspiration (ETc) by means of the software MABIA, which is an irrigation scheduling computer program [16,17,18]. The calculation procedures used by this model are based on dual crop coefficient approach according to the United Nations Food and Agriculture Organization (FAO) Penman-Montheith equation [19]. In addition, weeds were controlled by hand when needed. Harvest was on June 29, 2007. Seeds harvested were air-dried and stored at 4[degrees]C until use for further analysis.

Reagents and standards

All solvents used in our experiments (hexane, ethanol and methanol) were purchased from Merck (Darmstadt, Germany). The homologous series of [C.sub.7]-[C.sub.22] n-alkanes used for identification were obtained from Sigma Aldrich (Steinheim, Germany). Essential oil and fatty acid standards were purchased from Fluka (Riedel-de Haen, Switzerland) and Sigma Aldrich.

Total lipids extraction

Total lipids from seeds were extracted by the modified method of Bligh and Dyer, [20] according to Marzouk and Cherif, [21]. Thus, 1 g air-dried seed were fixed in boiling water for 5 min and then ground manually with chloroform/methanol/hexane mixture (4:3:2, v/v/v). After washing with water of fixation and decantation during 24 h at + 4 [degrees]C, the organic phase containing total lipids was dried under a stream of nitrogen, dissolved in toluene-ethanol (4:1, v/v) and stored at -20 [degrees]C for further analyses. Total lipid extraction was made in triplicate.

Fatty acid methylation

Total fatty acids of total lipids were converted into their methyl esters using the sodium methylate at 3% (Sigma, Aldrich, St Louis, MO, USA) in methanol according to the method described by Cecchi et al., [22]. Methyl heptadecanoate (C17:0) was used as an internal standard in order to quantify fatty acids. Fatty acid methyl esters (FAMEs) obtained were subsequently analysed.

Essential oil isolation

Whole air-dried seeds (50 g) were subjected to hydrodistillation for 90 min (time fixed after a kinetic survey during 30, 60, 90 and 120 min. The optimal yield was obtained at 90 min). The hydrodistillation was performed by a simple laboratory Quik-fit apparatus which consisted of a 1000 ml steam generator flask, a distillation flask, a condenser and a receiving vessel. Essential oils were extracted from the distillate using diethyl-ether as solvent (v/v) dried over anhydrous sodium sulphate then concentrated at + 35[degrees]C using a Vigreux column and stored at -20[degrees]C prior to analysis. All experiments were done in triplicates and results were expressed on the basis of dry matter weight (DMW).

Gas chromatography (GC-FID) analyses

Essential oil analysis was performed using a Hewlett-Packard 6890 gas chromatograph (Agilent Palo Alto, CA, USA) equipped with a flame ionization detector (FID) and an electronic pressure control (EPC) injector. A polar HP Innowax (PEG) column and an apolar HP-5 one (30 m x 0.25 mm, 0.25 Lim film thickness) were used. The carrier gas ([N.sub.2], U) flow was 1.6 ml [min.sup.-1]. The split ratio was 60:1. The analyses were performed using the following temperature program: oven temperature

isotherm at 35[degrees]C for 10 min, from 35 to 205[degrees]C at the rate of 3[degrees]C [min.sup.-1] and isotherm at 225[degrees]C during 10 min. Injector and detector temperatures were held at 250 and 300[degrees]C, respectively.

FAMEs were analyzed using the same apparatus previously described and separated on a RT-2560 capillary column (100 m x 0.25 mm, 0.20 mm film thickness). The oven temperature was kept at 170[degrees]C for 2 min, followed by a 3[degrees]C [min.sup.-1] ramp to 240[degrees]C and finally held there for an additional 15 min period. Nitrogen was used as carrier gas at a flow rate of 1.2 ml [min.sup.-1]. The injector and detector temperatures were maintained at 225[degrees]C.

Gas chromatography-mass spectrometry (GC-MS) analyses

The GC-MS analyses were performed on a gas chromatograph HP 6890 (II) interfaced with a HP 5973 mass spectrometer (Agilent Technologies, Palo Alto, California, USA) with electron impact ionization (70 eV). A HP-5MS capillary column (60 m x 0.25 mm, 0.25 [micro]m film thickness) was used. The column temperature was programmed to rise from 40 to 280[degrees]C at a rate of 5[degrees]C [min.sup.-1]. The carrier gas was helium with a flow rate of 1.2 ml [min.sup.-]1. Scan time and mass range were 1 s and 50-550 m/z, respectively. The injected volume was 1 [micro]L.

Compounds identification

FAMEs were identified by comparison of their retention times with those of authentic standards. The identification of essential oil components was based on a comparison of their retention indices (RI) relative to (C7-C20) n-alkanes with those of literature or with those of authentic compounds available in our laboratory. Further identification was made by matching their recorded mass spectra with those stored in the Wiley/NBS mass spectral library of the GC-MS data system and other published mass spectra [23]. Quantitative data were obtained from the electronic integration of the FID peak areas.

Statistical analyses

Data were subjected to statistical analysis using

statistical program package STATISTICA [24]. The one-way and multivariate analysis of variance (ANOVA) followed by Duncan's multiple range tests were employed and the differences between individual means were deemed to be significant at P < 0.05.

Results and discussion

Effect of water deficit on total fatty acids contents

As shown in Fig.1, the total fatty acid content in C. carvi seeds (mg [g.sup.-1] DW) subjected to increasing levels of water constraint declines significantly (P < 0.05) by about 29.01 and 47.53% under MWD and SWD, respectively, as compared to control plants.

These results are similar to those obtained in a previous work with Tunisian caraway seed ecotype from Haouaria which seed total fatty acid content decreased by about 35.17 and 56.59% under MWD and SWD, respectively, in comparison to the control. But, the decrease in the fatty acid content of this last ecotype is more pronounced [15].

In accordance with our findings, Bouchereau et al., [25] found a significant decrease in seed oil of Brassica napus L. genotypes. Besides, Rotundo and Westgate, [26] noted that water constraint imposed during seed filling decreased soybean oil content by about 35%. These findings were also similar to those reported by Bettaieb et al., [6] who noted that drought decreased significantly the foliar fatty acid content of sage (Salvia officinalis L.) by about 34% in moderate stressed plants; nevertheless, it declines sharply in severely stressed plants representing only 3.2% of the control.

[FIGURE 1 OMITTED]

Overall, these results showed that the reduction in TFA content are thought to be attributed to membrane lipid degradation under water deficit [27].

Effect of water deficit on total fatty acids proportion

Caraway seeds in control plants were characterized by a high proportion of monounsaturated fatty acids (MUFA) (56.82%) versus 27.41% of polyunsaturated (PUFA) and 15.77% of saturated ones (SFA) (Table 1). Petroselinic acid (C18:2n-12) was the major compound reaching over 34% of TFA, followed by linoleic (26.49%) and oleic (22.33%) acids.

In a previous work, we have found that the fraction of monounsaturated fatty acid in three Tunisian caraway seed ecotypes was mainly dominated by petroselinic acid which ranged from 31.53 to 38.36% [11].

Drought induced marked changes in fatty acid composition of caraway seeds and mainly that of the petroselinic one which is reduced by 15 and 20.3% compared with the control under moderate and severe water deficits, respectively. Linoleic and oleic acid proportions decreased significantly (P < 0.05) by 6.95 and 11.37% respectively at MWD whereas under SWD, their proportions declined of 12.16 and 19.97%, respectively.

Thus, our present results are slightly higher than those obtained in a previous work with Tunisian caraway seed ecotype originated from Haouaria; for example, we noted that petroselinic proportion decreased significantly by 12.7 and 18.47% under MWD and SWD, respectively [15].

In addition, we noted that water deficit increased the saturated acid proportions .Thus, under MWD, myristic, palmitic and stearic acids increased up to 59.44, 61.95 and 57.97%, respectively and 71.81, 105.81 and 256.52% under SWD, respectively. Thus, the major variation consisted in a decrease of the unsaturated acid proportion in favour of an increase in saturated ones.

These results are in agreement with those reported by Hamrouni et al., [28] who showed that the major variation of safflower (Carthamus tinctorius L.) aerial part lipids submitted to water deficit, consisted in a decrease of polyunsaturated fatty acid proportions (18:2 and 18:3) in favour of the saturated ones (16:0 and 18:0).

In the same context, Martins Junior et al., [29] noted that leaf fatty acid composition of bean (Phaseolus vulgaris L.) was affected by drought. This last decrerased polyunsaturated fatty acid contents (linoleic and linolenic acids) but increased saturated fatty acid ones (palmitic and stearic acids).

These results contrast with those of Bettaieb et al., [6] who reported that water deficit decreased the proportion of palmitic (16:0) and caused the disappearance of palmitoleic (16:1), stearic (18:0) and arachidic (20:0) acids.

Furthermore, the DBIs (double bond indexes) calculated according to Rie De Vos et al., [30] to evaluate the unsaturation degree of fatty acids pool, decreased significantly (P<0.05) in comparison to the control (Table 1). So, these results showed that water constraint tends to reduce the degree of unsaturation of C.carvi seed fatty acids. The same results were obtained by Hamrouni et al., [28] in safflower (Carthamus tinctorius L.) and Bettaieb et al., [6] in sage (Salvia officinalis L.) when these plants were subjected to water deficit.

In summary, these findings showed that this constraint tends to affect the quality and the stability of caraway seed oil and to reduce its degree of total fatty acids unsaturation as we have demonstrated in a previous work [15]. Indeed, water deficit causes degradative processes, an inhibition of lipid biosynthesis [31] and a stimulation of lipolytic and peroxidative activities [32,33] that are associated with decreased membrane lipid content.

Effect of water deficit on essential oil yield

Hydrodistillation of C. carvi seeds (control) offered an essential oil with an average yield of 0.38% (w/w the dry matter basis) (Fig.2). This yield is lower than that obtained with Tunisian caraway ecotype from Haouaria (0.47%) [15] and much lower than that reported by Bailer et al., [34] (2.8-3.3%) and even lower than that reported by Arganosa et al., [35] for the same species.

The essential oil yield is affected by the differents drought levels as we have found in a previous study [15]. Thus, it increased to 0.76 and 0.94% under MWD and SWD, respectively, in comparison to the control (Fig.2).

These results showed that water deficit enhances essential oil production in C.carvi seeds and this effect is more pronounced with water constraint sharpness. Since, MWD increased the essential oil yield by twice whereas this last was about 2.5 higher under SWD compared with the control.

In agreement with our findings, this increase is also observed in other aromatic plant species such as Pimpinella anisum L. [36], Petroselinum crispum [5] and Salvia officinalis [6].

Conversely, Fatima et al., [37] found that water deficit reduced essential oil content of two aromatic grasses species, Cymbopogon martinii and Cymbopogon winterianus. This decrease in essential oil yield could result from the effect of water constraint on plant growth and differentiation rather than a direct effect on essential oil biosynthesis.

Effect of water deficit on essential oil composition

Essential oil compounds identified in C. carvi seeds are listed in Table 2. In control plants, 41 compounds were identified out of which, carvone was the major compound (78.11%) followed by limonene (14.79%). Other minor constituents were noted such as [beta]-pinene, [beta]-myrcene, [gamma]-terpinene etc. Thus, carvone and limonene account for the main part and were commonly found in the essential oil of C. carvi seeds, but with different percentages depending on type of cultivars, sampling technique, extraction methods (supercritical fluid extraction and steam distillation), harvest time and storage period [38,39].

Water deficit induced an increase in the limonene percentage, estimated by 80.85 and 95.38% under MWD and SWD, respectively in comparison to the control. Besides, drought induced a decrease in the carvone proportion which was significantly estimated by 7.43 and 9.61% at MWD and SWD, respectively compared to the control (Table 2). However, carvone remained the major compound of caraway seed essential oil. Thus, drought had not affected the chemotype of caraway essential oil which is in agreement with our previous study on Tunisian caraway from Haouaria [15].

In spearmint (Mentha spicata L.), the content ([micro]g [g.sup.-1] DW) of the main compounds, which are limonene and carvone, increased by 50% in severely stressed as compared to well-watered leaves at the balsamic period. In rosemary (Rosmarinus officinalis L), the concentrations of a-pinene and camphor, the main monoterpenes, were more than 100% higher in severely stressed leaves than in well-watered leaves at balsamic period. Linalool showed the highest percentage increment respect to plant establishment [3].

The seed essential oil was characterized by the prevalence of ketones (86.88%) represented by carvone, trans-dihydrocarvone and cis-dihydrocarvone. The monoterpene hydrocarbons (8.21%) constitued the second main class and contained limonene as prominent constituent. The remaining fractions as aldehydes, oxygenated sesquiterpenes and esters formed the minor classes.

Hence, increasing levels of water deficit stimulated the biosynthesis of the monoterpene hydrocarbon class which proportion increased by 73.45 and 92.69% under MWD and SWD, respectively while ketone class decreased by 7.26 and 9.51% under MWD and SWD, respectively (Table 2). Thus, water deficit induced changes which were related to the relative proportions of C. carvi seed essential oil constituents but doesn't cause the appearance of new ones [15].

[FIGURE 2 OMITTED]

Conclusion

In conclusion, increasing levels of water constraint caused a significant reduction of the total fatty acid content and changes in their composition jugged by a decrease of the DBI under SWD. Moreover, a reduction in polyunsaturated fatty acids in favour of saturated ones was noticed.

Hence, the essential oil production were stimulated in response to water constraint. Consequently, the monoterpene compounds of the essential oil increased with the two levels of water deficit and were more pronounced at SWD.

In summary, the reduction in total fatty acids content and the increase of essential oil production induced by the water constraint may be a result of a new pattern of resource partitioning providing more carbon skeletons for the biosynthesis and accumulation of monoterpene compounds.

References

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Corresponding Author

Bochra Laribi, Institut National Agronomique de Tunis. 43, Av. Charles Nicolle-1082, Tunis, Tunisia. E.mail: bochra_laribi@yahoo.fr

(1) Bochra Laribi, (1) Karima Kouki, (1) Ali Sahli, (1) Abdelaziz Mougou and (2) Brahim Marzouk

(1) Institut National Agronomique de Tunis. 43, Av. Charles Nicolle-1082, Tunis, Tunisia.

(2) Laboratoire des substances bioactives, CBBC, BP 901, 2050- Hammam-Lif, Tunisia.

Bochra Laribi, Karima Kouki, Ali Sahli, Abdelaziz Mougou and Brahim Marzouk; Essential oil and fatty acid composition of a Tunisian caraway (Carum carvi L.) seed ecotype cultivated under water deficit
Table 1: Effect of water deficit on fatty acid composition (%) and
DBI changes of a Tunisian caraway (Carum carvi L.) seed ecotype
[C: control, MWD: moderate water deficit, SWD: severe water deficit
(Means of three replicates)].

                                 C

Myristic acid (C14:0)            10.43 [+ or -] 0.13 (c)
Palmitic acid (C16:0)             3.96 [+ or -] 0.01 (c)
Stearic acid (C18:0)              1.38 [+ or -] 0.01 (c)
Oleic acid (C18:1 n-9)           22.33 [+ or -] 0.01 (a)
Petroselinic acid (C18:1 n-12)   34.49 [+ or -] 0.07 (a)
Linoleic acid (C18:2)            26.49 [+ or -] 0.02 (a)
Linolenic acid (C18:3)            0.92 [+ or -] 0.00 (a)
SFA                              15.77 [+ or -] 4.66 (c)
MUFA                             56.82 [+ or -] 3.60 (a)
PUFA                             27.41 [+ or -] 1.08 (a)
* DBI                             1.13 [+ or -] 0.01 (a)

                                 MWD

Myristic acid (C14:0)            16.63 [+ or -] 0.24 (b)
Palmitic acid (C16:0)             6.73 [+ or -] 0.01 (b)
Stearic acid (C18:0)              2.18 [+ or -] 0.01 (b)
Oleic acid (C18:1 n-9)           19.79 [+ or -] 0.17 (b)
Petroselinic acid (C18:1 n-12)   29.32 [+ or -] 0.10 (b)
Linoleic acid (C18:2)            24.65 [+ or -] 0.47 (b)
Linolenic acid (C18:3)            0.71 [+ or -] 0.03 (b)
SFA                              25.54 [+ or -] 1.39 (b)
MUFA                             49.11 [+ or -] 1.74 (b)
PUFA                             25.36 [+ or -] 0.93 (b)
* DBI                             1.01 [+ or -] 0.02 (b)

                                 SWD

Myristic acid (C14:0)            17.92 [+ or -] 0.08 (a)
Palmitic acid (C16:0)             8.15 [+ or -] 0.03 (a)
Stearic acid (C18:0)              4.92 [+ or -] 0.04 (a)
Oleic acid (C18:1 n-9)           17.87 [+ or -] 0.02 (c)
Petroselinic acid (C18:1 n-12)   27.49 [+ or -] 0.03 (c)
Linoleic acid (C18:2)            23.27 [+ or -] 0.07 (b)
Linolenic acid (C18:3)            0.38 [+ or -] 0.00 (c)
SFA                              30.99 [+ or -] 3.77 (a)
MUFA                             45.36 [+ or -] 1.80 (c)
PUFA                             23.65 [+ or -] 1.19 (b)
* DBI                             0.93 [+ or -] 0.01 (c)

Values (means of three replicates [+ or -] SD) with different
superscripts (a-c) are significantly different at P < 0.05.
(SFA: saturated fatty acids; MUFA: monounsaturated fatty acids;
PUFA: polyunsaturated fatty acids; DBI: double bond index).

Table 2: Effect of water deficit on essential oil composition (%) of a
Tunisian caraway (Carum carvi L.) seed ecotype [C: control,
MWD: moderate water deficit, SWD: severe water deficit (Means of three
replicates)].

Compound *                        RI (a)   RI (b)   Identification

[alpha]-Pinene                    934      1032     GC/MS
Camphene                          951      1086     GC/MS.Co GC
[beta]-Pinene                     980      1123     GC/MS.Co GC
[beta]-Myrcene                    991      1166     GC/MS
Limonene                          1030     1206     GC/MS
[gamma]-Terpinene                 1062     1255     GC/MS.Co GC
(E)-[beta]-Ocimene                1050     1266     GC/MS.Co GC
p-Cymene                          1026     1280     GC/MS.Co GC
Terpinolene                       1092     1290     GC/MS.Co GC
Z-3-Hexenol                       855      1370     GC/MS.Co GC
Trans-limonene oxide              1136     1463     GC/MS
Camphor                           1143     1532     GC/MS.Co GC
Linalool                          1100     1545     GC/MS.Co GC
Linalyl acetate                   1257     1556     GC/MS.Co GC
[beta]-Elemene                    1594     1600     GC/MS.Co GC
Terpinene-4-ol                    1178     1611     GC/MS.Co GC
[beta]-Caryophyllene              1419     1612     GC/MS.Co GC
Trans-dihydrocarvone              1204     1627     GC/MS
Cis-dihydrocarvone                1197     1645     GC/MS
Allo-aromadendrene                1474     1661     GC/MS.Co GC
[alpha]-Terpineol                 1189     1700     GC/MS.Co GC
Germacrene-D                      1480     1719     GC/MS.Co GC
Dihydrocarveol                    1253     1720     GC/MS
Carvone                           1241     1740     GC/MS
[beta]-Selinene                   1481     1742     GC/MS.Co GC
[alpha]-Selinene                  1485     1745     GC/MS.Co GC
[alpha]- Farnesene                1508     1755     GC/MS.Co GC
Citronellol                       1229     1766     GC/MS.Co GC
[delta]-Cadinene                  1517     1772     GC/MS.Co GC
[gamma]-Cadinene                  1511     1776     GC/MS.Co GC
Cuminaldhyde                      1238     1785     GC/MS.Co GC
Perill[alpha]-aldehyde            1272     1789     GC/MS.Co GC
Nerol                             1228     1797     GC/MS.Co GC
Trans-carveol                     1218     1841     GC/MS
Cis-carveol                       1230     1869     GC/MS
Nonadecane                        1900     1900     GC/MS.Co GC
Perill[alpha]-alcool              1296     2001     GC/MS.Co GC
Spathulenol                       1575     2125     GC/MS.Co GC
Eugenol                           1356     2192     GC/MS.Co GC
Thymol                            1290     2198     GC/MS.Co GC
Carvacrol                         1296     2215     GC/MS.Co GC

Chemical classes

Monoterpene hydrocarbons (%)
Aldehydes (%)
Ketones (%)
Oxygenated monoterpenes (%)
Sesquiterpene hydrocarbons (%)
Oxygenated sesquiterpenes (%)
Esters (%)
Others (%)

Compound *                        Water deficit

                                  C

[alpha]-Pinene                    0.25 [+ or -] 0.00 (a)
Camphene                          0.13 [+ or -] 0.00 (b)
[beta]-Pinene                     0.09 [+ or -] 0.00 (b)
[beta]-Myrcene                    0.08 [+ or -] 0.00 (b)
Limonene                          7.57 [+ or -] 3.28 (c)
[gamma]-Terpinene                 0.03 [+ or -] 0.03 (b)
(E)-[beta]-Ocimene                0.03 [+ or -] 0.03 (b)
p-Cymene                          0.02 [+ or -] 0.00 (b)
Terpinolene                       0.02 [+ or -] 0.02 (b)
Z-3-Hexenol                       0.02 [+ or -] 0.02 (b)
Trans-limonene oxide              0.07 [+ or -] 0.07 (c)
Camphor                           0.02 [+ or -] 0.02 (b)
Linalool                          0.02 [+ or -] 0.02 (b)
Linalyl acetate                   0.15 [+ or -] 0.03 (b)
[beta]-Elemene                    0.02 [+ or -] 0.02 (c)
Terpinene-4-ol                    0.05 [+ or -] 0.05 (c)
[beta]-Caryophyllene              0.02 [+ or -] 0.02 (c)
Trans-dihydrocarvone              0.10 [+ or -] 0.10 (c)
Cis-dihydrocarvone                0.37 [+ or -] 0.06 (a)
Allo-aromadendrene                0.27 [+ or -] 0.01 (a)
[alpha]-Terpineol                 0.02 [+ or -] 0.02 (b)
Germacrene-D                      0.15 [+ or -] 0.15 (c)
Dihydrocarveol                    0.08 [+ or -] 0.01 (b)
Carvone                           86.41 [+ or -] 2.04 (a)
[beta]-Selinene                   0.22 [+ or -] 0.02 (b)
[alpha]-Selinene                  0.13 [+ or -] 0.13 (b)
[alpha]- Farnesene                0.34 [+ or -] 0.02 (c)
Citronellol                       0.04 [+ or -] 0.00 (b)
[delta]-Cadinene                  0.43 [+ or -] 0.03 (a)
[gamma]-Cadinene                  0.61 [+ or -] 0.07 (a)
Cuminaldhyde                      0.03 [+ or -] 0.00 (a)
Perill[alpha]-aldehyde            0.27 [+ or -] 0.00 (a)
Nerol                             0.03 [+ or -] 0.03 (b)
Trans-carveol                     0.27 [+ or -] 0.04 (b)
Cis-carveol                       0.10 [+ or -] 0.02 (c)
Nonadecane                        0.11 [+ or -] 0.07 (a)
Perill[alpha]-alcool              0.15 [+ or -] 0.04 (b)
Spathulenol                       0.27 [+ or -] 0.08 (b)
Eugenol                           0.49 [+ or -] 0.37 (a)
Thymol                            0.41 [+ or -] 0.17 (a)
Carvacrol                         0.42 [+ or -] 0.31 (a)

Chemical classes

Monoterpene hydrocarbons (%)      8.21 [+ or -] 2.50 (b)
Aldehydes (%)                     0.38 [+ or -] 0.12 (a)
Ketones (%)                       86.88 [+ or -] 9.75 (a)
Oxygenated monoterpenes (%)       0.79 [+ or -] 0.08 (b)
Sesquiterpene hydrocarbons (%)    2.18 [+ or -] 0.19 (a)
Oxygenated sesquiterpenes (%)     0.58 [+ or -] 0.09 (a)
Esters (%)                        0.15 [+ or -] 0.00 (a)
Others (%)                        0.11 [+ or -] 0.00 (a)

Compound *                        Water deficit

                                  MWD

[alpha]-Pinene                    0.18 [+ or -] 0.06 (b)
Camphene                          0.08 [+ or -] 0.02 (c)
[beta]-Pinene                     0.05 [+ or -] 0.03 (c)
[beta]-Myrcene                    0.10 [+ or -] 0.03 (a)
Limonene                          13.69 [+ or -] 2.87 (b)
[gamma]-Terpinene                 0.03 [+ or -] 0.01 (b)
(E)-[beta]-Ocimene                0.03 [+ or -] 0.01 (b)
p-Cymene                          0.04 [+ or -] 0.00 (a)
Terpinolene                       0.03 [+ or -] 0.01 (b)
Z-3-Hexenol                       0.03 [+ or -] 0.01 (b)
Trans-limonene oxide              0.12 [+ or -] 0.01 (a)
Camphor                           0.04 [+ or -] 0.00 (a)
Linalool                          0.07 [+ or -] 0.01 (a)
Linalyl acetate                   0.07 [+ or -] 0.00 (c)
[beta]-Elemene                    0.06 [+ or -] 0.00 (b)
Terpinene-4-ol                    0.13 [+ or -] 0.04 (a)
[beta]-Caryophyllene              0.06 [+ or -] 0.00 (a)
Trans-dihydrocarvone              0.27 [+ or -] 0.02 (a)
Cis-dihydrocarvone                0.31 [+ or -] 0.03 (b)
Allo-aromadendrene                0.21 [+ or -] 0.02 (b)
[alpha]-Terpineol                 0.04 [+ or -] 0.00 (a)
Germacrene-D                      0.46 [+ or -] 0.28 (a)
Dihydrocarveol                    0.17 [+ or -] 0.03 (a)
Carvone                           79.99 [+ or -] 2.51 (b)
[beta]-Selinene                   0.40 [+ or -] 0.06 (a)
[alpha]-Selinene                  0.24 [+ or -] 0.07 (a)
[alpha]- Farnesene                0.39 [+ or -] 0.04 (a)
Citronellol                       0.07[+ or -] 0.00 (a)
[delta]-Cadinene                  0.38 [+ or -] 0.00 (b)
[gamma]-Cadinene                  0.53 [+ or -] 0.02 (b)
Cuminaldhyde                      0.05 [+ or -] 0.01 (a)
Perill[alpha]-aldehyde            0.23 [+ or -] 0.02 (b)
Nerol                             0.05 [+ or -] 0.00 (a)
Trans-carveol                     0.29 [+ or -] 0.02 (b)
Cis-carveol                       0.29 [+ or -] 0.02 (b)
Nonadecane                        0.05 [+ or -] 0.00 (b)
Perill[alpha]-alcool              0.12 [+ or -] 0.02 (c)
Spathulenol                       0.29 [+ or -] 0.05 (b)
Eugenol                           0.10 [+ or -] 0.03 (c)
Thymol                            0.19 [+ or -] 0.13 (c)
Carvacrol                         0.07 [+ or -] 0.03 (c)

Chemical classes

Monoterpene hydrocarbons (%)      14.24 [+ or -] 1.54 (a)
Aldehydes (%)                     0.42 [+ or -] 0.09 (a)
Ketones (%)                       80.57 [+ or -] 6.02 (b)
Oxygenated monoterpenes (%)       1.26 [+ or -] 0.09 (a)
Sesquiterpene hydrocarbons (%)    2.73 [+ or -] 0.17 (a)
Oxygenated sesquiterpenes (%)     0.66 [+ or -] 0.10 (c)
Esters (%)                        0.07 [+ or -] 0.00 (c)
Others (%)                        0.05 [+ or -] 0.00 (b)

Compound *                        Water deficit

                                  SWD

[alpha]-Pinene                    0.16 [+ or -] 0.06 (c)
Camphene                          0.24 [+ or -] 0.16 (a)
[beta]-Pinene                     0.18 [+ or -] 0.18 (a)
[beta]-Myrcene                    0.12 [+ or -] 0.07 (a)
Limonene                          14.79 [+ or -] 1.11 (a)
[gamma]-Terpinene                 0.11[+ or -] 0.01 (a)
(E)-[beta]-Ocimene                0.12 [+ or -] 0.02 (a)
p-Cymene                          0.02 [+ or -] 0.00 (b)
Terpinolene                       0.08 [+ or -] 0.01 (a)
Z-3-Hexenol                       0.07 [+ or -] 0.01 (a)
Trans-limonene oxide              0.09 [+ or -] 0.02 (b)
Camphor                           0.03 [+ or -] 0.00 (ab)
Linalool                          0.06 [+ or -] 0.01 (a)
Linalyl acetate                   0.18 [+ or -] 0.02 (a)
[beta]-Elemene                    0.19 [+ or -] 0.19 (a)
Terpinene-4-ol                    0.10 [+ or -] 0.01 (b)
[beta]-Caryophyllene              0.04 [+ or -] 0.04 (b)
Trans-dihydrocarvone              0.24 [+ or -] 0.06 (b)
Cis-dihydrocarvone                0.27 [+ or -] 0.08 (c)
Allo-aromadendrene                0.18 [+ or -] 0.06 (c)
[alpha]-Terpineol                 0.02 [+ or -] 0.00 (b)
Germacrene-D                      0.24 [+ or -] 0.09 (b)
Dihydrocarveol                    0.16 [+ or -] 0.00 (a)
Carvone                           78.11 [+ or -] 1.13 (b)
[beta]-Selinene                   0.20 [+ or -] 0.13 (b)
[alpha]-Selinene                  0.08 [+ or -] 0.08 (c)
[alpha]- Farnesene                0.36 [+ or -] 0.04 (b)
Citronellol                       0.04 [+ or -] 0.00 (b)
[delta]-Cadinene                  0.31 [+ or -] 0.10 (c)
[gamma]-Cadinene                  0.45 [+ or -] 0.07 (c)
Cuminaldhyde                      0.03 [+ or -] 0.00 (a)
Perill[alpha]-aldehyde            0.17 [+ or -] 0.06 (c)
Nerol                             0.02 [+ or -] 0.02 (b)
Trans-carveol                     0.52 [+ or -] 0.40 (a)
Cis-carveol                       0.32 [+ or -] 0.19 (a)
Nonadecane                        0.07 [+ or -] 0.01 (b)
Perill[alpha]-alcool              0.23 [+ or -] 0.16 (a)
Spathulenol                       0.32 [+ or -] 0.04 (a)
Eugenol                           0.42 [+ or -] 0.06 (b)
Thymol                            0.32 [+ or -] 0.11 (b)
Carvacrol                         0.33 [+ or -] 0.08 (b)

Chemical classes

Monoterpene hydrocarbons (%)      15.82 [+ or -] 1.89 (a)
Aldehydes (%)                     0.36 [+ or -] 0.06 (a)
Ketones (%)                       78.62 [+ or -] 4.95 (b)
Oxygenated monoterpenes (%)       1.50 [+ or -] 0.07 (a)
Sesquiterpene hydrocarbons (%)    2.05 [+ or -] 0.13 (a)
Oxygenated sesquiterpenes (%)     0.91 [+ or -] 0.04 (b)
Esters (%)                        0.18 [+ or -] 0.00 (a)
Others (%)                        0.07 [+ or -] 0.00 (b)

* Components are listed in order of elution in polar column
(HP-Innowax). Values with different letters (a-c) are significantly
different at P < 0.05.

Note: RI (a) and RI (b): retention indices relatives to n-alcanes,
on (a) apolar column (HP-5) and (b) polar column (HP-Innowax).
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Title Annotation:Original Article
Author:Laribi, Bochra; Kouki, Karima; Sahli, Ali; Mougou, Abdelaziz; Marzouk, Brahim
Publication:Advances in Environmental Biology
Article Type:Report
Geographic Code:6TUNI
Date:Jan 1, 2011
Words:6320
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