Essential Oil of Daucus glaber Forssk
El-Sayed S. Mansour*, Galal T. Maatooq, Ashraf T. Khalil, El-Sayed M. Marwan*,
and Amal A. Sallam
Pharmacognosy Department, Faculty of Pharmacy, Mansoura University, Mansoura 35516,
Egypt. Fax: 02-0 50-2 24 74 96. E-mail: sayed50002000@yahoo.com
* Authors for correspondence and reprint requests
Z. Naturforsch. 59 c, 373Ð378 (2004); received February 24/April 25, 2003
The composition of the essential oil of the fruits, leaves and stems of Daucus glaber Forssk
has been studied by GC/MS. It was found that, the essential oil of the fruits consists of
monoterpene hydrocarbons (limonene and sylvestrene are the majors) and phenylpropanoids
(elemicin is the major). Sylvestrene has never been reported before in the essential oil of
any Daucus species. The study of the essential oil of the leaves revealed the presence of
monoterpene hydrocarbons; limonene and γ-terpinene are the majors and a small amount
of sylvestrene. The essential oil of stems consists of monoterpene hydrocarbons (γ-terpinene
is the major), terpene alcohols (mainly 4-terpineol) and phenylpropanoids (myristicin and
elemicin are the majors). It is interesting that, the essential oil of the fruits is free from any
oxygenated terpenes while that of the stems is free from limonene and sylvestrene which are
present in the essential oil of the fruits and leaves in fairly large amounts. The essential oil
of the fruits, leaves and stems shows broad antimicrobial activities against both gram positive
and gram negative bacteria. In addition, the volatile oil of the stem, particularly, show activities against Candida albicans (yeast). Also, the prepared oils have variable cytotoxic activities
with LC50 21.52, 36.01 and 42.34 µg/ml, respectively.
Key words: Daucus glaber, Essential Oil, GC/MS
Introduction
The genus Daucus, Apiaceae, comprises about
60 annual and biennial species mostly distributed
in Europe, Africa, West Asia, few ones in North
America and Australia. The genus Daucus is represented in Egypt by 8 species (Tackholm, 1972).
Many of these plants have been used by natives
as diuretics, emollient, vermifuge, carminative and
stomachic (Keith, 1965; Jafri El-Gadi, 1977) and
some have edible roots, Daucus carota.
It is reported that the genus Daucus is the richest genus of the Apiaceae concerning its essential
oil content. The essential oil pattern of the fruits
was found to be very useful for separating and
characterizing the genus within the family (Harborne, 1971; Williams and Harborne, 1972). Monoterpene hydrocarbons were found to be predominant (Lewis and Elvin-Lewis, 1977; Watt and
Wijik, 1961). Limonene was reported in the essential oil of the above ground part of Daucus carota
cultivated in Moldavia (Bakina et al., 1972), Daucus carota var. boissieri (Halim et al., 1988), Daucus syrticus Murb. (El-Alfy et al., 1994) and Daucus capillifolus Gilli. (Haman et al., 1989). Also,
limonene was found in the essential oil of the
0939Ð5075/2004/0500Ð0373 $ 06.00
fruits, leaves and stems of Daucus carota var. maximus (Saad et al., 1995).
Phenylpropanoids, especially elemicin, were reported in the essential oils of the fruits of Daucus
syrticus Murb. (El-Alfy et al., 1994) and Daucus
capillifolius Gilli (Haman et al., 1989).
The monoterpene alcohol geraniol was reported
in the essential oil of the fruits of Daucus syrticus
Murb. (Halim et al., 1988) and Daucus capillifolius
Gilli (El-Alfy et al., 1994).
The sesquiterpene alcohol carotol was found in
the essential oil of the fruits of Daucus syrticus
Murb. (El-Alfy et al., 1994), but geraniol, nerol
and carotol were detected in that of Daucus carota
var. boissieri cultivated in Egypt (Halim et al.,
1988), wild red, black and yellow varieties of Daucus carota growing in Pakistan (Ashraf et al.,
1977).
The monoterpene ester, geranyl acetate was detected in the essential oil of the fruits of several
varieties of Daucus carota (Pigulevskii and Kovaleva, 1955a; Pigulevskii and Kovaleva, 1955b; Pigulevskii et al., 1960; Ashraf et al., 1979), neryl acetate was found as a main constituent of the
essential oil of the fruits of Daucus carota ssp.
(wild carrot) and Daucus carota ssp. sativus (cultivated carrot) (Kilibarda et al., 1996).
” 2004 Verlag der Zeitschrift für Naturforschung, Tübingen · http://www.znaturforsch.com · D
374
E. S. Mansour et al. · Essential Oil of Daucus glaber Forssk
Table I. Composition of the essential oil of the fruit.
Peak scan #
Retention
Relative
time tR [min] composition
(%)
M+
peak
Base
peak
Fragmentation peaks Component
(m/z)
Adams,
1995 (DB-S)
616
836
1248Ð1255
8:13
10:03
13:29Ð13:33
0.01
0.18a
18.08
136.1
93.1
41.1,77.1, 91, 121a
136.1
93.1
0307
0319
0474
1461Ð1696
15:16Ð17:13
37.02
136.1
93.1
limonene
0481
1725
17:28
2.91
136.1
93.1
γ-terpinene
0545
3180
29:36
2.51
178.1
178.1
3702Ð4200
33:58Ð38:07
32.69
208.1
208.1
41.1, 53.1, 67, 68.1,
79, 107, 121.1
41.2, 53.1, 67, 68.2,
77, 79, 107, 121
41.1, 51, 53, 65.1,
77.1, 91, 105, 121.1 g
41.1, 51, 65,77.1,
91.1, 103.1, 107.1, 115,
135.1, 147.1, 163.1
41.1, 55.1, 77.1, 91.1,
105.1, 133.1, 150.1,
177.1, 193.1
α-thujene
α-pinene
sylvestrene
Daucus glaber Forssk grows well in sand dunes
and sandy sea shores in the Northern region of the
Nile Delta and flowers from March to early May.
In previous publications, two triester phenylpropanoids, daucoglabrin and isodaucoglabrin were
separated (Halim and Mansour, 1989, 1990). Nothing was reported about the composition of the
essential oil of Daucus glaber Forssk, therefore, we
are concerned with studying the composition of
the essential oil content of Daucus glaber Forssk
using GC/MS technique and also, studying its
physical and biological properties.
Results and Discussion
The essential oil of the fruits, leaves and stems
of Daucus glaber Forssk was separately prepared
by steam distillation adopting the Egyptian pharmacopoeia method (1984). The essential oil of the
fruits (4 % v/w) is colorless, has disagreable odour
and optical rotation + 1.27∞, while that of the
leaves (0.67 % v/w) has pale yellow color, characteristic odour and optical rotation + 0.12∞ but the
essential oil of the stems (0.10 % v/w) has yellow
Constituent
Monoterpene hydrocarbons
Sesquiterpenc hydrocarbons
Total hydrocarbons
Monoterpene alcohols
Sesquiterpene alcohols
Phenylpropanoids
Terpene esters
methyleugenol 1403
elemicin
1772
color, characteristic odour and optical rotation Ð
0.31∞. Each oil was analyzed by GC/MS and the
results are listed in Tables IÐIV.
It was found that the essential oil of the fruits
(Table I) consists chiefly of monoterpene hydrocarbons and phenylpropanoids (Table II). Monoterpene hydrocarbons are present in a significant amount (58.3 %) and consist mainly of
limonene (37.0 %), sylvestrene (18 %) and a
smaller amount of γ-terpinene (2.9 %). Sylvestrene has never been reported before in the
essential oil of any Daucus species. Phenylpropanoids are also majors and consist mainly of elemicin (23.7 %) and methyl eugenol (2.5 %). It was
found that the essential oil of the fruits does not
contain any oxygenated terpenes, viz, monoterpene alcohols, sesquiterpene alcohols and monoterpene esters.
The essential oil of the leaves (Table II) consists
of monoterpene hydrocarbons (61.5 %), total hydrocarbons (61.8 %), phenylpropanoids (19.7 %),
monoterpene alcohols (8.2 %) and sesquiterpene
alcohols (1.2 %). The monoterpene hydrocarbons
Fruit
Leaf
Stem
58.3%
Ð
28.3%
Ð
Ð
35.2%
Ð
61.5%
0.4%
61.8%
8.2%
1.2%
19.7%
Ð
43.9%
3.0%
46.9%
25.8%
11.1%
1.1%
41.7%
Table II. Different major constituents
of the essential oil of fruits, leaves and
stems.
E. S. Mansour et al. · Essential Oil of Daucus glaber Forssk
375
Table III. Composition of the essential oil of the leaves.
M+
peak
Base
peak
0.16
2.04
136.1
136.1
91.1
93.0
11:29 to 11:35
13:44 to 13:48
1.52
3.56
Ð
136.1
Ð
93.0
1301
13:56
2.76
136.1
93.0
1346
14:18
2.51
136.1
1363 to 1504
14:27 to 15:37
5.33
136.1
1595
16:23
21.73
136
1647
16:49
21.88
136.0
1661
16:56
1.60
154.1
1732
17:32
0.79
154
2033 to 2090
20:02 to 20:31
5.31
154
2112
3020 to 3027
20:42
28:16 to 28:20
0.45
1.55
Ð
178
3163
29:28
0.30
204
3568 to 3775
32:51 to 34:35
18.16
208
3794
34:44
0.39
220
3931
35:53
5198
46:28
Peak scan #
Retention
time tR [min]
634
950 to 959
8:22
11:00 to 11:04
1009 to 1021
1278 to 1285
Relative
composition
(%)
0.83
90.30
222
296
Fragmentation peaks
(m/z)
Component
Adams,
1995 (DB-S)
41.1, 77.1, 91, 121a
41.1, 56.1, 69.1, 77.1,
79, 91, 105, 107, 121.1
Ð
41.1, 53, 77.1, 79, 91,
107, 121.1
α-thujene
sabinene
0307
0379
β-terpinene
mentha-2,8diene
2-carene
Ð
0388 transmeta
0395 cis-meta
0427
3-carene
0444
sylvesterene
0474
limonene
0481
γ-terpinene
0545
41.1, 53, 77.1, 79, 91,
107, 121.1
93.0
41.1, 53, 77.1, 79, 91,
107, 121.1.
93.0
41.1, 53, 67, 68,1, 79,
91, 107, 121.1
93.1
41.1, 3, 67.1, 68, 79,
91, 107, 121.0
93.0
43.1, 65.1, 77.1, 79,
91, 105, 121.0
71.1
43.0, 55.1, 69.1, 81,
111, 121.1, 136.1, 139
43.1
41, 55.1, 71.1, 79, 81.1,
93, 111.1, 121.1, 139.1
71
41, 43.1, 55.1, 93.1,
111.1, 136.1
Ð
Ð
178
41.1, 65.1, 177.1, 91.1,
103.1, 107, 1115.1, 135,
147.1, 163.1
91.1 & 41.1, 55.1, 77, 79.1,
161.1
91.1, 93, 105, 107, 119,
133.1, 161.1, 189.2a
208
41, 53, 65.1, 71.1, 91.1,
105, 118, 133.1, 150.1,
165, 177.1, 193.1
43.1 & 41, 55.1, 67.1, 77, 79.1,
91.1
91.1, 93, 105, 119, 131,
147.2, 159.1, 162.2,
187.1, 205.2
59.1
41,43,55, 79.1, 91.1,
93, 109.1, 121.1, 149.2,
164.2, 189.2, 204.2b
71.1
41, 43.1, 55.1, 57, 81.1,
95.1, 123.1
(61.5 %) consist mainly of limonene and γ-terpinene nearly in equal amounts (21.7 %) (Table III).
Also, there are small amounts of sylvestrene
(5.3 %), mentha-2,8-diene (3.6 %), 2-carene
(2.8 %) and 3-carene (2.5 %). The phenylpropanoid fraction resembles that of the fruit and is
characterized by the presence of elemicin (18.2 %)
and a small amount of methyleugenol (1.6 %). It
is evident that the essential oil of the leaves is free
from myristicin. The sesquiterpene hydrocarbon
menth-2-en-1-ol 0682
(cis-para)
menth-2-en-1-ol 0725
(trans-para)
4-terpineol
0820
γ-terpineol
methyleugenol
Ð
1403
α-gurjunene
Ð
1421
elemicin
1772
spathulenol
1825
β-eudesmol
1993
phytol
2636
fraction of the oil of the leaves consists of α-gurjunene (0.3 %), while the sesquiterpene alcohol fraction is represented by β-eudesmol (0.9 %) and
spathulenol (0.4 %), which have never been reported before in the essential oil of any Daucus
species.
The essential oil of the stems (Table II) consists
chiefly of monoterpene hydrocarbons, terpene alcohols and phenylpropanoids (43.9 %, 25.8 % and
11 % of the oil composition, respectively), as well
376
E. S. Mansour et al. · Essential Oil of Daucus glaber Forssk
Table IV. Composition of the essential oil of the stem.
M+
peak
Base
peak
0.13
1.84
0.84
2.56
2.86
6.28
3.77
136.1
136.1
93.1
93.1
136.1
136.1
136.1
136
6.18
19.48
136
136.1
93.0
93.0
93.0
93.1
and
119.1
119.1
93.0
4.58
136.1
93.1
22.13
154
71.1
22:11
22:14
1.77
0.77
Ð
154
Ð
59.1
22:23Ð22:34
1.09
154
Peak scan #
Retention
time tR [min]
666
983Ð994
1013
1060Ð1116
1189
1291
1367Ð1407
8:37
11:16Ð11:21
11:31
11:54Ð12:23
12:59
13:50
14:28Ð14:48
1447Ð1468
1589
15:08 Ð 15:19
16:20
1653
16:52
2230Ð2275
21:40Ð22:03
2291
2296
2315Ð2336
Relative
composition
(%)
84.1
+
2398
23:05
0.56
2432
23:22
0.52
2785
2828
26:18
26:40
0.36
0.66
152 (M
119.1
acetate)
152 (M+- 91.1
acetate)
204
161
204
2949
27:40
0.45
204
41.1
3254
30:13
0.55
204
121 &
193.1
3266
30:19
0.35
204
3281
30:26
0.65
204.2
3538
32:35
5.05
192
192
3589
33:01
6.04
208
208
3679
33:46
1.98
220.2
43.1
3920
35:47
1.78
222
59
93.1
Fragmentation peaks
(m/z)
Component
Adams,
1995 (DB-S)
41.1,
41.1,
Ð
41.1,
41.1,
41.1,
41.1,
α-thujene
sabinene
β-terpinene
2-carene
3-carene
β-phellandrene
4-carene
0307
0379
Ð
0427
0444
0482
ocimene
γ-terpinene
Ð
0545
ocimene allo
0701
4-terpineol
0820
γ-terpineol
α-terpineol
Ð
0852
piperitol
0865
77.1, 91, 121
77.1, 91, 121
77.1,
77.1,
77.1,
68.1,
91,
91,
91,
91,
121
121
121
121
41, 68.2, 91, 121, 134
41, 43.1, 65.1, 77.1, 79,
91, 105, 121.1
41, 53.1, 77, 79.1, 91,
105, 121.1
41, 43, 55.1, 69.1, 93.1,
111.1, 136.1
Ð
43, 81.1, 93.1, 95.1,
121.1, 136.1
41.1, 55.1, 79.1, 83,
93.1, 111.1, 139.1
43.1, 79.1, 81.1, 91.1,
134.1
43.1, 79.1, 92, 119.1
chysanthenyl ac-0967
etate (trans)
4-thujen-2α-yl- Ð
acetate
α-copaene
1334
β-cubebene
1371
41.1, 43, 55.1, 77.1,
91.1, 93, 105.1, 119.1,
133.1, 161.2, 189.2, 41.1,
43, 55.1, 79.1, 91.1, 105.1,
119.1, 133.1, 189.2
55, 57.1, 79, 91.1, 93,
caryophyllene
105, 133.1, 161.2,
178.1, 189.2
41.1, 53, 67.1, 79.1, 91, γ-elemene
105, 107, 123.1, 147,
161.2, 189.2
41.1, 55, 67.1, 77, 79.1, γ-gurjunene
91, 93.1, 105, 107, 119,
121, 137, 161.2
41.1, 55, 67.1, 77, 79.1, α-selinene
91, 105, 107, 119, 121,
137, 161.2, 189.
53, 65, 77.1, 191.1,
myristicin
119.1, 131.1, 133.1,
147, 165.1
65.1, 77.1, 91.1, 105,
elemicin
150.1, 165, 177.1, 193.1
41, 55.1, 69.1, 79.1,
spathulenol
91.1, 105, 119.1, 131,
147.1, 159.1, 162.2,
187.2, 205.2
41, 43, 62, 79.1, 91.1,
β-eudesmol
95.1, 109.1, 121.1, 149.2,
164.2, 189.2, 204.2
1442
1476
1575
1631
1691
1772
1825
1993
E. S. Mansour et al. · Essential Oil of Daucus glaber Forssk
377
Table V. Antimicrobial activity of the essential oil of fruits, leaves and stems.
Microorganism
Staphylococcus aureus
Bacillus subtilis
Escherichia coli
Candida albicans
Fruit oil
80 mg/ml
Leaf oil
80 mg/ml
Stem oil
80 mg/ml
Control
(ampicillin)
5 mg/ml
Control
(clotrimazole)
5 mg/ml
2.5 mm
2.0 mm
Ð
Ð
0.5 mm
2.5 mm
Ð
Ð
0.5 mm
Ð
Ð
3.5 mm
10.5 mm
13.0 mm
Ð
Ð
Ð
Ð
Ð
9.0 mm
Table VI. Cytotoxic activity of the essential oil of fruits,
leaves and stems.
Concentration
Corrected mortality* (%)
Fruit oil Leaf oil Stem oil
1
mg/ml
0.1 mg/ml
0.01 mg/ml
100
56.7
46.6
100
59.6
54.1
96.4
76.4
20
and then finely powdered. The plant was kindly
identified by Dr. I. Mashaly, Associate Professor
of Systematic Botany, Department of Botany, Faculty of Science, Mansoura University, Mansoura,
Egypt and the identification was further confirmed
by Botanical Center Kew, London, England. A
voucher specimen is kept at the Department of
Pharmacognosy, Faculty of Pharmacy, Mansoura
University, Mansoura, Egypt.
* Using Abbot’s formula.
Preparation of the volatile oils
as small amounts of sesquiterpenes: hydrocarbons
(3 %), alcohols (3.8 %) and esters (1 %). It is evident from the composition of the stem oil (Table
IV) that sylvestrene is absent from the essential
oil of the stems while it is present in a significant
amount in the essential oil of both the fruits and
the leaves. Also, there are small amounts of chrysanthenyl acetate (0.6 %) and 4-thujen-2α-yl acetate (0.5 %), which have never been reported before in the essential oil of any Daucus species.
The essential oil of the fruits, leaves and stems
showed a weak antimicrobial activity against both
gram positive and gram negative bacteria (Table
V). This was explained by the presence of high
percentage of phenolic and/or oxygenated compounds. At the same time, the prepared oils
showed cytotoxic activity with LC50 21.52, 36.01
and 42.34 µg/ml, respectively (Table VI) which
may be attributed also to the presence of high percentage of phenolic and/ or oxygenated compounds.
Experimental
Plant material
Ripe and mature fruits as well as leaves and
stems of Daucus glaber Forssk, growing wild on
El-Narges mountains, Balteem, Kafr El-Shiekh,
north region of the Nile Delta, Egypt, were separately collected in May 2001, air-dried in shade
Powdered fruits, leaves and stems (100 g, each)
were separately subjected to steam distillation for
8 h adopting the Egyptian pharmacopoeia (1984)
method. Each oil was collected, dried over anhydrous sodium sulfate and kept in the freezer until
analysis.
The GC/MS analysis was carried out at the National Research Center, Dokki, Cairo, Egypt on
GC/MS Fenningan Mat SSQ 7000 with Digital
DEC 3000 workstation fitted with a fused silica
DB-5 (30 m ¥ 0.25 mm ID, 5 % phenyl methyl polysiloxane) capillary column with helium as a carriergas at a flow rate of 1.6 ml/min, column head
pressure 13 psi. The gas chromatography was coupled to a mass selective detector (MS) at 70 eV in
EI ionization mode. The sample was injected in
1 µl size in splitless mode. The temperature was
programmed initially at 50 ∞C for 1 min, and then
increased with a rate of 4 ∞C/min up to 250 ∞C.
Identification of the components was based on
matching their retention time and spectral indices
with some reference samples and with those published in literature (Adams, 1989, 1995) and also
by using NST mass spectral database of the gas
chromatograph computer.
Determination of physical constants
Specific rotation was performed on the methanolic solution of the oil (0.1 %) and measured in
378
E. S. Mansour et al. · Essential Oil of Daucus glaber Forssk
1 dM tubes at the sodium D line using Perkin-Elmer 141 polarimeter.
Screening for the cytotoxic activity of the oils
The prepared oils under investigation were
tested for their antimicrobial activity. The discagar diffusion method (Cruickshank et al., 1975)
was applied. Different bacteria and yeast (as test
organisms) and ampecillin and clotrimazole (as
control) were used. The susceptibility of various
microorganisms to the inhibitory effect of the oils
and the control is presented in Table I.
The brine shrimp eggs (Artemia salina Leach,
available in pet shops, Cairo, Egypt) were hatched
in a shallow rectangular dish (22 cm ¥ 32 cm) filled
with artificial sea water and double-distilled water.
The eggs (ca. 50 mg) were sprinkled. After 48 h,
the phototropic nauplii were collected and separated by the divider from their shells. The brine
shrimp technique was applied (Meyer et al., 1982).
The rate of mortality was determined and corrected for the negative control mortality by Abbot’s formula. The LC50 was obtained by making
a linear regression of the corrected rate of mortality (Y) versus log concentration (X), then the Xintercept when Y = 50 % is found and the antilog
was determined. The results are listed in Table II.
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Screening for the antimicrobial activity of the
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