Chemical composition and antimicrobial activity of essential oil from Daucus carota sativa seeds

Abstract

The contents of EO components were calculated using GC peak areas without correlation coefficients. Components were identified based on a comparison of retention times and full mass spectra with those of standard EO components and pure compounds and a search of the NBS, NIST, and Wiley mass spectrometric libraries. A total of 18 chemical components consisting of 99.98% of the EO were identified in seeds of Daucus carota sativa. According to the GC/MS results, the main components of carrot-seed EO were β-bisabolene (80.49%), α-asarone (8.8%), and cis-α-bergamoten (5.51%). The total amount of main components was 95.72% of the total EO content. Table 1 gives the chemical components and their molecular formulas and relative percent contents according to the mass spectrometric analyses. The main components of carrot-seed EO from France and Hungary were α-pinene (13%), β-pinene (18%), carotol (18%), and β-bisabolene [5, 6]. However, the main components of EO from Uzbekistan were β-bisabolene (80.49%), asarone (8.8%), and cis-α-bergamoten (5.51%). The variation in the EO component compositions is probably due to growing conditions. The antiicrobial activity of the EO fractions against Candida albican and Staphylococcus aureus was determined by a modified Barry test method [7]. Table 2 gives the results. Table 2 shows that mixtures of terpenes and sesquiterpenes from carrot-seed EO exhibited a high antimicrobial activity and possibly protect seeds from bacterial and fungal infection. Pure α-asarone exhibited sedative and antipyretic properties; α-humulene, anticancer activity against MCF-7, PC-3, A-549, DLD-1, M4BEU, and CT-26 tumor cells [8]. According to the results, carrot-seed EO is a valuable natural substance and an object for investigation of further practical applications.

Full text

1) Pharmaceutical Institute, Xinjiang Medical University, Urumchi, PRC, 830054; 2) Xinjiang Technical Institute of
Physics and Chemistry, Academy of Sciences, PRC, Urumchi, Xinjiang, PRC, 830011, Beijing South Road 40-2, fax (+86-991)
383 56 79, e-mail: abulimitiyili@hotmail.com; 3) A. S. Sadykov Institute of Bioorganic Chemistry, Academy of Sciences of
the Republic of Uzbekistan, Tashkent, e-mail: ibchem@uzsci.net. Translated from Khimiya Prirodnykh Soedinenii, No. 4,
pp. 404-405, July-August, 2007. Original article submitted April 19, 2007.
0009-3130/07/4304-0495
©
2007 Springer Science+Business Media, Inc.
495
Chemistry of Natural Compounds, Vol. 43, No. 4, 2007
CHEMICAL COMPOSITION AND ANTIMICROBIAL ACTIVITY
OF ESSENTIAL OIL FROM Daucus carota sativa SEEDS
X. Imamu,
1
A. Yili,
2
H. A. Aisa,
2
V. V. Maksimov,
3
UDC 633.81
O. N. Veshkurova,
3
and Sh. I. Salikhov
3
Essential oils from many plants are known to exhibit antimicrobial activity that can act as a chemical protectant against
pathogenic plant diseases [1, 2]. Essential oils (EO) from carrot seeds contain biologically active compounds [3, 4] and,
although their biological activity has been known for a long time, the chemical composition and biological activity of essential
oil from seeds of carrots growing in Uzbekistan have not yet been studied.
Commercially available carrot seeds (
Daucus carota sativa
, 100 g) were extracted for 4 h by steam distillation. The
amber-colored essential oil was separated from water by ether and dried overnight over anhydrous Na
2
SO
4
to afford essential
oil in 2.2% yield.
The chemical composition of EO was studied by GC/MS on a Perkin—Elmer Turbo Mass Aid System XL
gas chromatograph with a quadrupole mass spectrometer as the detector. We used a quartz capillary column (PE-5MS,
30 m × 0.25 mm) with a deposited stationary phase of copolymer (5% phenylmethylsilicone) 0.25 µm thick. The He carrier
gas flow rate was 1 mL/min. The column temperature thermostat was programmed as follows: hold for 2 min at 75°C, heat
to 100°C at 2°C/min, to 160°C at 4°C/min; and to 220°C at 2°C/min; hold at this temperature for 2 min. The duration of the
final isothermal regime was 20 min at 230°C. Samples (0.2 µL) were injected with vaporizer temperature 180°C, detector
220°C, ionization potential 70 eV, and
m
/
z
30-550.
The contents of EO components were calculated using GC peak areas without correlation coefficients. Components
were identified based on a comparison of retention times and full mass spectra with those of standard EO components and pure
compounds and a search of the NBS, NIST, and Wiley mass spectrometric libraries.
A total of 18 chemical components consisting of 99.98% of the EO were identified in seeds of
Daucus carota sativa
.
According to the GC/MS results, the main components of carrot-seed EO were
β
-bisabolene (80.49%),
α
-asarone (8.8%), and
cis-
α
-bergamoten (5.51%). The total amount of main components was 95.72% of the total EO content.
Table 1 gives the chemical components and their molecular formulas and relative percent contents according to the
mass spectrometric analyses.
The main components of carrot-seed EO from France and Hungary were
α
-pinene (13%),
β
-pinene (18%), carotol
(18%), and
β
-bisabolene [5, 6]. However, the main components of EO from Uzbekistan were
β
-bisabolene (80.49%), asarone
(8.8%), and cis-
α
-bergamoten (5.51%). The variation in the EO component compositions is probably due to growing conditions.
The antiicrobial activity of the EO fractions against Candida albican and Staphylococcus aureus was determined by
a modified Barry test method [7]. Table 2 gives the results.
Table 2 shows that mixtures of terpenes and sesquiterpenes from carrot-seed EO exhibited a high antimicrobial activity
and possibly protect seeds from bacterial and fungal infection. Pure
α
-asarone exhibited sedative and antipyretic properties;
α
-humulene, anticancer activity against MCF-7, PC-3, A-549, DLD-1, M4BEU, and CT-26 tumor cells [8]. According to the
results, carrot-seed EO is a valuable natural substance and an object for investigation of further practical applications.

496
TABLE 1. Chemical Composition of Essential Oil from Seeds of Daucus carota sativa
Component Formula MW
Content,
%
Component Formula MW
Content,
%
cis
-
α
-Bergamoten
Caryophyllene
β
-Sesquiphellandrene
β
-Bisabolene
α
-Humulene
trans
-Anethole
Caryophyllene oxide
p
-Menth-1(7),8(10)-dien-9-ol
Carotol
C
15
H
24
C
15
H
24
C
15
H
24
C
15
H
24
C
15
H
24
C
10
H
12
O
C
15
H
24
O
C
10
H
16
O
C
15
H
26
O
204
204
204
204
204
148
220
152
152
5.51
0.21
0.13
80.49
0.46
0.09
0.23
0.32
0.32
α
-Farnesene
Lanceol
Methylisoeugenol
Spatulenol
α
-Bisabolol
α
-Bergamoten
Bisabolene
2,6,10-Dodecatrien-1-ol 3,7,11-trimethyl
α
-Asarone
C
15
H
24
C
15
H
24
O
C
11
H
14
O
2
C
15
H
24
O
C
15
H
26
O
C
15
H
24
C
15
H
24
C
15
H
26
O
C
12
H
16
O
3
204
220
178
220
222
204
204
222
152
0.52
0.43
0.07
0.49
0.07
0.09
0.54
0.83
8.82
TABLE 2. Antimicrobial Activity of Daucus carota sativa Essential Oil*
Microorganism Dilution MIC, mg/mL MEC, mg/mL
Candida albican
Staphylococcus aureus
1:32
1:16
1:512
1:256
15.63
-
0.976
-
-
31.25
-
1.95
______
*After 48 h incubation at 30°C.
ACKNOWLEDGMENT
The work was performed with support from the Chinese Academy of Sciences. We thank the Head of the Laboratory
of the Chemistry of Natural Products of Xinjiang Technical Institute of Physics and Chemistry for financial support and the
Laboratory of Microorganisms of Xinjiang Medical University for determining the activities.
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