全 文 ： 2010, Vol. 31, No. 07 食品科学 ※基础研究154
Essential Oil Compositions and Antioxidant Activities of Two
Ziziphora Species in Xinjiang
XING Si-lei，ZHANG Pi-hong，JI Qiao-ling*，JIA Hong-li，WANG Xue-hua
(College of Life Science and Technology, Xinjiang University, Urumqi 830046, China)
Abstract：The chemical composition of essential oils isolated by hydrodistillation from the aerial parts of Ziziphora
clinopodioides Lam. and Ziziphora pamiroalaica Juz. were analyzed by gas chromatography/mass spectrometry (GC-MS). Ten
constituents representing 99.7% of the Z. clinopodioides oils were identified, which contained (+)-(R)-Pulegone (80.7%),
Menthone (8.3%), Piperitenone (4.9%) and (+)-Isomenthone (2.6%) as the major components; On the other hand, twenty-nine
constituents representing 99.8% of the oils from Z. pamiroalaica. were identified, the major compounds consisted of (+)-(R)-
Pulegone (45.9%), (+)-Isomenthone (24.1%), (+)-Neomenthol(10.1%), Thymol (9.4%). The antioxidant activity of the oils was
assessed by measurement of the free radical scavenging (DPPH) activity, the reductive potential, Superoxide anion scavenging
activity, NaNO2 scavenging ability and by the TBARS assay, compared with that of synthetic antioxidants: Thymol, Vitamin
C (VC) and butylated hydroxytoluene (BHT). Results showed that the oil from Z. pamiroalaica. was better than that from Z.
clinopodioides in antioxidant abilities.
Key words ：Ziziphora clinopodioide Lam.；Ziziphora pamiroalaica Juz.；essential oils；GC-MS analysis；antioxidant
activity
新疆芳香和帕米尔新塔花精油组成及其抗氧化的研究
邢思雷，张丕鸿，计巧灵 *，贾红丽，王雪华
(新疆大学生命科学与技术学院，新疆 乌鲁木齐 830046)
摘 要：优化水蒸气蒸馏法提取新疆芳香和帕米尔两种新塔花挥发油的最佳条件，利用气相色谱 -质谱联用技术分
析两种新塔花挥发油的化学成分和组成，研究两种新塔花挥发油的抗氧化能力。从芳香新塔花的地上部分提取的挥
发油中分离鉴定出 10种成分，占挥发油总量的 99.7%以上。芳香新塔花的主要成分为长叶薄荷酮(80.7%)、薄荷酮
(8.3%)、胡椒烯酮(4.9%)及异薄荷酮(2.6%)。从帕米尔新塔花的地上部分提取的挥发油中分离鉴定出 29种成分，占
挥发油总量的 99.8%以上。帕米尔新塔花精油中主要含有长叶薄荷酮(45.9%)、异薄荷酮(24.1%)、(+)-新薄荷醇
(10.1%)和百里香酚(9.4%)。通过与百里香酚，VC和 BHT的对比，新塔花精油具有一定的抗氧化能力，能够有效
清除 DPPH·，超氧阴离子自由基和羟自由基；能够保护脂质体，抑制其过氧化；并且具有明显的清除亚硝酸
盐的作用。结果表明，帕米尔新塔花精油的抗氧化效果优于芳香新塔花精油。
关键词：芳香新塔花；帕米尔新塔花；精油；G C - M S 分析；抗氧化活性
中图分类号：TS264.3 文献标识码：A 文章编号：1002-6630(2010)07-0154-06
收稿日期：2009-10-29
作者简介：邢思雷(1983—)，男，硕士研究生，研究方向为植物生物技术。E-mail：168xsl@sina.com
*通信作者：计巧灵(1956—)，女，教授，研究方向为植物细胞生物学。E-mail：Wji1118@yahoo.com
Global interest in biopreservation of food systems has
recently been increased because of great economic costs of
deterioration and poisoning of food products by food
pathogens. Essential oils and extracts of various species of
edible and medicinal plants, herbs, and spices constitute of
very potent natural biologically active agents. Biological
activities of Ziziphora essential oils depend on their chemical
composition which is determined by the genotype and influ-
enced by environmental conditions. Recent studies have
showed that Ziziphora species have strong antimicrobial and
... .
155※基础研究 食品科学 2010, Vol. 31, No. 07
antioxidant activities. The genus Ziziphora consists of thirty
species all over the world locating from Mediterranean to
Central Asia and Afghanistan. In China, there are only three
species (Ziz iphora pamiroala ica Juz. ; Ziz iphora
clinopodioide Lam.and Ziziphora tenuior Linn.) just found
in Xinjiang[1]. Traditionally, Ziziphora plant has been widely
used in food as a flavoring agent, in medicine as a herbal drug
for treatment of gastrointestinal disorders and wound heal-
ing material[2-3]. In recent years, the chemical composition[4-5],
antibacterial activities[6]and antioxidant activities[7]of the es-
sential oils from Ziziphora genus have been studied quite
intensively. It was reported that the oils of Ziziphora genus
exhibited strong antioxidant and antibacterial activities, (+)-
(R)- Pulegone, Menthone-D3 and (+)-Isomenthone were de-
scribed as the main constituents in the essential oil. However,
the literatures on chemical composition and antioxidant ac-
tivity of the extracts from Ziziphora genus in Xinjiang are
rather scarce[8]. Especially, to the best of our knowledge, the
chemical composition and antioxidant activities of the es-
sential oils from Z. pamiroalaica. have not yet been reported.
The aims of this study were to determine the chemical
composition of the oils from Z. clinopodioides. and Z.
pamiroalaica. by GC-MS , and to evaluate the antioxidant
activities of the oils by comparison with the synthetic
antioxidants, such as BHT, VC and Thymol.
1 Materials and Methods
1.1 Materials
The plants (Z. clinopodioides Lam. and Z. pamiroalaica
Juz.) were collected during the flowering stage in August,
2007, from the Ya mountains (near Urumqi) and Jigen village
of Wuqia county (near Kashgar) in Xinjiang, respectively.
The identification of plant materials was confirmed by Pf.
Zhou Gui-ling, at the College of Forestry, Xinjiang Agricul-
tural University, China. The materials were dried in the dark
at room temperature before analysis.
1.2 Preparation of the extracts
The dried aerial parts of plant materials were submitted
to water distillation for 6 h in a full glass apparatus (1000 mL).
The oils were isolated by using a Clevenger-type apparatus,
and dried over hydrous sodium sulfate for 24 h, after filtration,
stored at 4 ℃ in the sealed brown glass vials until tested.
1.3 Analysis of the essential oils
According to the previous report[9], the gas chromatogra-
phy-mass spectrometry (Daojin GC-MS-QP2010) analysis were
carried out on a Rtx-5MS capillary column (30 m×0.32 mm,
0.25μm film thickness). The oven temperature was
programmed, 50－105 ℃ , at a rate of 1 ℃/min, subsequently,
at 5℃/min up to 210 ℃; and then held isothermal for 5 min;
injector and detector temperatures: 250 ℃ and 200 ℃,
respectively; carrier gas: nitrogen (1－ 2 mL/min); detector:
FID; The samples were injected using split sampling
technique, ratio 1:20; ionization energy: 70 eV; scan range:30
－500 u and scan time: 1 s. The chemical compositions of the
oils were obtained from the normalization method through
the GC peak areas , the identities of the components were
accomplished by cluster analysis using the Wiley & Nist
software (table 1), also referred to corresponding data of
components of relative oils.
2 Antioxidant Activity Evaluation
2.1 DPPH free radical scavenging assay
The effect of the essential oils on DPPH free radical was
estimated according to the procedure described by
Yamaguchi and others[10]. An aliquot of ethanol (0.1 mL)
containing different concentrations of the oils was added to
4 mL of 0.03 mmol/L DPPH ethanol solution. After incuba-
tion for 20 h at 25 ℃, in the dark, the absorbance of the
resulting solution was measured at 517 nm against a corre-
sponding blank. BHT and Thyme were taken as standard
antioxidants. The radical-scavenging activity (RSA) was
calculated by using the equation:

A0－Ai
RSA/% =—————× 100

A0
where A0 is the absorbance of the control reaction
(containing all reagents except the test compound), and Ai is
the absorbance of the test compound.
2.2 Reductive potential
The reductive potential was determined according to
the method of Oyaizu[11]. The oils with different concentra-
tions were mixed with 2.5 mL of 0.2 mol/L sodium phosphate
buffer (pH 6.6) and 2.5 mL of 1% potassium ferricyanide [K3Fe
(CN)6]. After incubated at 50 ℃for 20 min, 2.5 mL of 10g/100mL
trichloroacetic acid were added, the mixture was then centri-
fuged at 3000 r/min for 10 min. The upper layer (about 5 mL)
was carried out and mixed with 4 mL of distilled water and
1 mL of 0.1% ferric chloride. After 10 min, the absorbance
was measured at 700 nm against a blank. A higher absor-
bance indicates a higher reductive potential. BHT and Thyme
were tested for comparison.
. . ..
2010, Vol. 31, No. 07 食品科学 ※基础研究156
2.3 Superoxide anion scavenging activity
The improved assay method for superoxide dismutase
described by Liu et al[12] was used. Briefly, 2 mL of test
samples in different concentrations and 5 mL of Tris-HCl
buffer (0.05 mol/L, pH8.2) were prepared in test tubes, fol-
lowed by incubation at 25 ℃ for 30 min, then 1ml of incu-
bated pyrogallol solution (3 mmol/L) was added. After 5min,
1mL of HCl (10 mmol/L ) was added to stop the reaction. The
absorbance was measured at 320 nm. Mixture with 95% etha-
nol instead of the test sample was used as control and mix-
ture without pyrogallol was used as blank (Aj). The scaveng-
ing ability was calculated by the following equation:

Ai－Aj
Scavenging/%=(1－————)× 100

A0
where Ai was absorbance of the test sample. the A0 was
the absorbance of the control, Aj was the absorbance of the
blank.
2.4 TBARS assay
A modified thiobarbituric acid-reactive substances
(TBARS) assay was used to measure the potential antioxi-
dant capacity of Thymus.altaicus essential oils[13]. Egg yolk
homogenate was used as a lipid-rich media, an aliquot of
yolk material was mixed with phosphate buffer solution (pH
7.4) to produce a 1:25 (V/V) homogenate by ultrasonication for
5 min. Then 2.4mL of the homogenate was incubated with
the test sample in the presence of FeSO4 (25 mmol/L, 2.4 mL)
at 37 ℃ for 4 h, followed by addition of trichloroacetic acid
(50 %, V/V, 0.8 mL) and 2-thiobarbituric acid (TBA, 2 mL). The
mixture was heated at 100 ℃ for 10 min. After centrifugation
at 8000 g for 15 min, the absorbance (Ai) of the supernatant was
measured at 532 nm. Inhibition ratio was calculated by the
following formula:

A0－Ai
Inhibition ratio/%= ————× 100

A0
where A0 was the absorbance of the control sample
(without test sample) and Ai was the absorbance of the test
sample. The IC50 was calculated from the graph of antioxidant
activity percentage against extract concentration.
2.5 NaNO2 scavenging ability
The method described by Jia and others[14] was per-
formed with a slight modification. An aliquot of 0.1mL of test
sample with different concentrations was added to 0.8 mL
of 0.5mol/L sodium citrate-HCl buffer (pH 3.0) mixed with
0.1 mL of 100 mg/kg NaNO2. After incubation at 37 ℃ for 1h,
2 mL of 1% sulfanilic acid solution and 1mL of 0.4% n-1-
Naphthalene ethylene diamine hydrochloride solution
were added in order. After 15 min, the absorbance (Ai) was
measured at 540 nm. A control was performed without the
test sample (A0). NaNO2 scavenging ability was calculated
with the equation:

A0－Ai
NaNO2 inhibition ratio/%=—————× 100

A0
The IC50 was calculated according to the relationship of
concentration and scavenging ability. Thymol was used as
reference compound.
2.6 Statistical analysis
For each experiment, three replications were made. The
data statistical analysis was performed by analysis of vari-
ance (ANOVA) using STATISTICA 5.5 (Stat, Tulsa, OK, USA)
software. Datas are presented as mean values ± standard
deviation.
3 Results and Discussions
3.1 Essential oil yields and composition
Peak No.
Z. pamiroalaica Z. clinopodioides
Components Composition/% Components Composition/%
1 alpha-Thujene 0.2 Limonene 0.5
2 (-)-alpha-Pinene 0.2 (+)-Isomenthone 2.6
3 Camphene 0.2 Menthone-D3 8.3
4 beta-Phellandrene 0.2 trans-Isopulegone 1.1
5 beta-Pinene 0.4 (+)-(R)- Pulegone 80.7
6 beta-Myrcene 0.3 Phenol,4-ethenyl-2-methoxy 0.2
7 3-Octanol 0.1
Bicyclo[3.2.1]octan-2-
0.2one,1,6,6-trimethyl-8-oxa
8 alpha-Terpinene 0.1 Piperitenone 4.9
9 Cymene 1.7 p-Menthan-2-one,3,4-epoxy 0.3
10 Limonene 0.6 Citronellic acid 0.9
11 1,8-Cineole 0.5
12 gamma-Terpinene 0.2
13 (+)-Isomenthone 24.1
14 Menthone-D3 1.8
15 (+)-Neomenthol 10.1
16 Borneol 1.6
17 trans-Isopulegone 0.2
18 (+)-(R)- Pulegone 45.9
19 Piperitone 0.2
20 Bornyl acetate 0.2
21 Thymol 9.4
22 Geranyl formate 0.1
23 Carvacrol 0.2
24 Piperitenone 0.6
25 beta-Bourbonene 0.1
26 cis-Jasmone 0.1
27 trans-Caryophyllene 0.1
28 Germacrene-D 0.3
29 Spathulenol 0.1
Table 1 Chemical components and composition of essential oils
from Ziziphora clinopodioides Lam. and Ziziphora pamiroalaica
Juz. (Composition percentages＜ 0.05 as traces )
157※基础研究 食品科学 2010, Vol. 31, No. 07
The results obtained by GC-MS analysis of the essential
oils of Z. clinopodioides and Z. pamiroalaica are listed in
Table 1. The essential oil yields ranged from 0.9% to 1.2%, The
higher oil yield was obtained from Z. clinopodioides, while
the lower one was obtained from Z. pamiroalaica. The oil
yields in the present study were comparable to reports by
Liu, who found the essential oil yield from aerial parts of
Z. clinopodioides to be 0.6%, and Zhang, who reported the
essential oil content of Z. clinopodioides grown in Buerjin
county (Xinjiang) to be 0.7%. Such variations in the oil yields
may be attributed to the varied climatic and geographical
conditions of the regions.
Ten and twenty-nine components were identified from
the essential oils of Z. clinopodioides and Z. pamiroalaica,
respectively, amounting to 99.7%－ 99.8% of the total oils.
The chemical components of Z. clinopodioides essential oils
identified were less than that reported by Ozturk[15]. (+)-(R)-
Pulegone was the main component attaining 80.7%, 45.9% in
the oils of Z. clinopodioides and Z. pamiroalaica ,
respectively, which is in accordance with the predominant
portion (45.8%) of the Z. clinopodioides oils in Iran[16]. In
addition, Menthone (8.3%), Piperitenone (4.9%) and (+)-
Isomenthone (2.6%) were present in Z. clinopodioides oils,
while (+)-Isomenthone (24.1%), (+)-Neomenthol (10.1%),
Thymol (9.4%) were special compounds in Z. pamiroalaica
oils. Also some compounds, such as Menthofuran, Borneol
and Cymene, were only found in Z. pamiroalaica, which
haven t been reported yet.
3.2 Antioxidants activities of essential oils
DPPH radicals. The IC50 of BHT, Thymol, Z. clinopodioides
and Z. pamiroalaica were 0.043, 0.020, 8.604 mg/mL and 5.266
mg/mL, respectively, so the scavenging activities were as
follows: Thymol＞ BHT＞ Z. pamiroalaica essential oils
＞ Z.clinopodioides essential oils. The results showed that
the scavenging ability of Z. pamiroalaica was higher than
that of Z. clinopodioides, which may be respect that the
extracts of Z. pamiroalaica contain some special components,
such as Thymol.
As can be seen from Fig. 1, BHT, Thymol and the extracts
of Z. bungeana all showed good scavenging activities on
Values are mean of triplicate determination± SD.
Fig.2 The reductive potential of BHT, Thymol and essential oils
from Z. clinopodioides and Z. pamiroalaica
18000
16000
14000
12000
10000
8000
6000
4000
100
80
60
56
48
40
32
24
20
16
0
BHT
Thymol
C
on
ce
nt
ra
tio
n/
(μ
g/
m
L
)
A700nm
0 0.2 0.4 0.6 0.8 1.0
Z.clinopodioides
Z.pamiroalaica
Fig.1 The DPPH·scavenging effects of BHT, Thymol and
essential oils from Z. clinopodioides and Z. pamiroalaica
20000
15000
10000
5000
2000
1000
500
400
300
200
100
75
50
40
25
20
10
7.5
5
4
2.5
2
1
0.5
0
BHT
Thymol
C
on
ce
nt
ra
tio
n/
(μ
g/
m
L
)
Clearance/%
0 10 20 30 40 50 60 70 80 90 100
Z.clinopodioides
Z.pamiroalaica
Values are mean of triplicate determination± SD.
,
Generally, the reductive potential of the essential oils
from Zizphora genus increased steadily with increasing
oil concentrations in the range of 2 mg/mL to 20 mg/mL
(P＜ 0.05). Z. pamiroalaica and Z.clinopodioides essential
oils showed the maximum reductive potential of 0.78, 0.77, at
16 mg/mL and 18 mg/mL, respectively. On the other hand, BHT
showed a reductive potential of 0.79 at 0.06 mg/mL and re-
ductive potential of Thymol was 0.77 at 0.1 mg/mL (Fig. 2).
Thereby, with regard to reductive potential, the oils extracted
from Z. pamiroalaica were more effective than those of
Z. clinopodioides. Apparently, high reductive potential
might be due to some special components in Z. pamiroalaica
essential oils.
The scavenging abilities of the oils compared with that
of Vitamin C (VC) for superoxide anion are shown in Fig. 3. The
scavenging ability initially increased with increasing con-
centrations before 1.4mg/mL and 1mg/mL for the essential
oils from Z. clinopodioides and Z. pamiroalaica, which was
in correspondence with the highest scavenging activities
(15% and 24%, respectively), then decreased. The scaveng-
ing ability of VC increased with increasing concentrations,
2010, Vol. 31, No. 07 食品科学 ※基础研究158
which showed 100% scavenging ability for superoxide radi-
cals at 0.25 mg/mL. Therefore, the highest scavenging activ-
ity of these samples followed the order: VC＞Z. pamiroalaica
essential oils＞ Z. clinopodioides essential oils.
oils, BHT, Thymol was 7.9, 5.7, 2.54 ×10-3 mg/mL and 0.1 mg/
mL, respectively. The capacity of inhibiting lipid peroxidation
of these samples followed the order: BHT＞ Thymol＞ Z.
pamiroalaica essential oils ＞ Z. clinopodioides essential oils.
Though the capacity of inhibiting lipid peroxidation of the oils
is lower than that of BHT and Thymol, it may be enough to
inhibit lipid peroxidation, which may answer for its food use.
Fig.5 showed that the NaNO2 scavenging abilities of
Thymol and the essential oils. Both of them had NaNO2 scav-
enging ability in a dose-dependent manner (P＜ 0.05). The
oils from Z. clinopodioides and Z. pamiroalaica showed a
high scavenging ability of 81.6% and 98.5%, respectively, at
40 mg/mL. However, Thymol, used as a positive control,
exhibited the strongest NaNO2 scavenging activity of 99.2%
at 0.2 mg/mL. The IC50 of Thymol, Z. pamiroalaica essential
oils, Z. clinopodioides essential oils was 0.03, 0.5 mg/mL and
3 mg/mL, respectively. Results revealed that Thymol and the
oils had the scavenging ability to some degree. The NaNO2
scavenging effect of the extracts and the standards followed
the order: Thymol＞ Z. pamiroalaica essential oils＞
Z. clinopodioides essential oils.
Values are mean of triplicate determination± SD.
Fig.4 Inhibition effects of BHT, Thymol and essential oils from
Z. clinopodioides and Z. pamiroalaica on oxidation of phospholipid
20000
10000
8000
5000
2000
1000
600
200
100
50
20
15
10
5
2
1.5
1
0.5
0
C
on
ce
nt
ra
tio
n/
(μ
g/
m
L
)
Inhibition/%
0 10 20 30 40 50 60 70 80 90
BHT
Thymol
Z.clinopodioides
Z.pamiroalaica
Values are mean of triplicate determination± SD.
Fig.5 The NaNO2 scavenging abilities of Thymol and essential
oils from Z. clinopodioides and Z. pamiroalaica
40000
30000
20000
10000
4000
3000
2000
1000
400
300
200
100
40
30
20
10
4
2
0
C
on
ce
nt
ra
tio
n/
(μ
g/
m
L
)
Clearance/%
0 10 20 30 40 50 60 70 80 90 100
Thymol
Z.clinopodioides
Z.pamiroalaica
4 Conclusions
Ziziphora plants in Xinjiang have been widely used in
the country as aromatic herbs in cooking, and also for their
medicinal properties in folk medicine, not only to improve or
modify the flavour of foods, but also to avoid its deterioration.
Th e e x t r ac t s o b ta ine d f rom Z. pa mir oa l a ic a an d
Z. clinopodioides exhibited good antioxidants activities. The
results obtained indicate a high potential of application for the
Ziziphora essential oils.
Values are mean of triplicate determination± SD.
Fig.3 Inhibition effects of VC, oils from Z. clinopodioides and
Z. pamiroalaica on pyrogallol autoxidation
2200
2000
1800
1600
1400
1200
1000
800
400
300
250
200
160
120
80
20
10
0
C
on
ce
nt
ra
tio
n/
(μ
g/
m
L
)
VC
Z.clinopodioides
Z.pamiroalaica
Inhibition/%
0 10 20 30 40 50 60 70 80 90 100
Inhibition of lipid peroxidation was evaluated by using
thiobarbituric acid-reactive substances (TBARS), and the
antioxidant activity was detected by decreased TBARS
formation, which can come out by antioxidant donation of
hydrogen or electron to the radical or by direct reaction with
it. This is a highly sensitive method, the results being fully
dependent on efficient centrifugation to remove the precipi-
tated protein. As can be seen from Fig. 4, the inhibition
potential of the oils was dose-dependent, the best ac t iv i -
t ies were observed at high concentrations. The IC 50
of Z. clinopodioides essential oils, Z. pamiroalaica essential
159※基础研究 食品科学 2010, Vol. 31, No. 07
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