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Chemical Composition and Antioxidant Activities of Buds and Leaves of

Capers (Capparis ovata Desf. var. canescens) Cultivated in Turkey

Article in Journal of Essential Oil Research · January 2007

DOI: 10.1080/10412905.2007.9699233

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 J. Essent. Oil Res.,El-Ghorab et al.
19, 72–77 (January/February 2007)

Chemical Composition and Antioxidant Activities

of Buds and Leaves of Capers (Capparis ovata
Desf. var. canescens) Cultivated in Turkey

Ahmed El-Ghorab
Flavor and Aromatic Department, National Research Center, Dokki, Cairo, Egypt
Takayuki Shibamoto*
Department of Environmental Toxicology, University of California, Davis, CA 95616
Mehmet Musa ÖZCAN
Faculty of Agriculture, Department of Food Engineering, Selcuk Universty, 42031 Konya/Turkey

Abstract
Essential oils of caper (Capparis ovata Desf. var. canescens) buds and leaves obtained by steam distillation fol-
lowed by solvent extraction were analyzed by GC and GC/MS. Eighty-six compounds were identified from the caper
bud extract and 100 from the caper leaf oil. The major volatile compounds found in caper bud oil were benzyl alco-
hol (20.4%), furfural (7.4%), ethanal methyl pentyl acetal (5.9%), 4-vinyl guaiacol (5.3%), thymol (5.1%), octanoic
acid (4.8%) and methyl isothiocyanate (4.5%). The major volatile compounds found in caper leaves were methyl
isothiocyanate (20.0%), thymol (15.5%), 4-vinyl guaiacol (4.3%), hexyl acetate (3.6%) and trans-theaspirane (2.6%).
These oils inhibited hexanal oxidation by 80% over 40 days at the level of 200 µg/mL. Also, they inhibited oxidation
of 1,1-diphenyl-2-picrylhydrazyl hydrate by over 70% at the 500 µg/mL level. The dichloromethane and methanol
extracts from caper buds and leaves exhibited higher antioxidant activities than those of their essential oils in both
testing systems.

Key Word Index

Capparis ovata Desf. var. canescens, Cappasidaceae, capers, essential oil composition, methyl isothiocyanate,
benzyl alcohol, thymol, antioxidant activity.

Introduction Chemical studies on Capparis spinosa L. have reported the

presence of glycosides, such as quercetin and kaempferol (7)
Capparis ovata Desf. var. canescens is one of the most com-
and an anti-inflammatory principle (8). A few other substances
monly used seasoning ingredients in Mediterranean kitchens.
such as alkaloids, glucosinolate, lipids flavonoids and miscel-
Certain species and varieties of capers have been cultivated
laneous isothiocyanate glucosides have also been identified in
in special regions of the Mediterranean. These plants show
different species of genus Capparis (9–13).
strong resistance to harsh environmental conditions and have
Recently, the presence of antioxidants in natural plants,
become an important economic resource in Southern Europe
including herbs and spices, has received much attention as
in recent decades (1–3). The main producers and exporters of
a disease preventive substance (14). Natural antioxidants
capers are Spain, Morocco and Italy. Recently, packed brined
of plant origin are generally classified as vitamins, phenolic
caper products have been exported from Turky to European
compounds, or flavonoids. In addition to the use of the plant
countries (4,5).
per se, volatile or flavor chemicals isolated from various plants
Capers are used for flavoring foods such as anchovies,
have been shown to have certain antioxidative activities.
pasta, pizza and commerical frozen foods. Various parts of the
The volatile compounds and antioxidative activity of caper
caper plant, especially the buds and leaves, have been used in
buds and leaves have not been reported prior to this study.
drugs, cosmetics and foods (4). The flavor intensity is directly
Therefore, in the present study, the chemical compositions
related to bud maturity, and capers as large as 1 cm are com-
and antioxidant activities of the essential oils obtained from
monly used. Caper leaves steeped in vinegar have been used
both caper (Capparis ovata Desf. var. canescens) buds and
to treat ulcers (6).
leaves were investigated.

*Address for correspondence Received: September 2005

Revised: January 2006
1041-2905/07/0001-072$14.00/0­—© 2007 Allured Publishing Corp. Accepted: March 2006

72/Journal of Essential Oil Research Vol. 19, January/February 2007

 C. ovata

Experimental their inhibitory effect toward oxidation of aldehyde to acid

according to a previously published method (16–19). Various
Plant materials: The caper (Capparis ovata Desf. var.
concentrations of volatile and less-volatile extracts (50, 100,
canescens) plants were planted and harvested in Selcuklu-
and 200 µg/mL) were added to 2 mL of a dichloromethane
Konya, Turkey.
solution of hexanal (3 mg/mL) containing 0.2 mg/mL of un-
Isolation of volatile components: Each sample of dried
decane as a GC internal standard. The oxidation of the sample
ground caper buds or leaves (100 g) was placed in a 3 L round-
solution was initiated by heating at 60°C for 10 min in a sealed
bottom flask with 1 L deionized water. The solution was steam
vial, after which the vial was stored at room temperature. The
distilled for 4 h. The distillate (900 mL) was extracted with 100
headspace of each vial was purged with pure air (1.5 L/min, 3
mL dichloromethane using a liquid-liquid continuous extrac-
s) every 24 h for the first 10 days. The decrease in hexanal was
tor for 6 h. After the extract was dried over anhydrous sodium
monitored at eight-day intervals for 40 days. Standard antioxi-
sulfate, the solvent was removed by a rotary flash evaporator
dant BHT was also examined for the purpose of comparison
(BUCHI 461 SWITZERLAND). The distillation was stopped
with the antioxidative activity of the samples. The quantitative
when the volume of extract was reduced to approximately 1 mL
analysis of hexanal was conducted according to a GC internal
and then the solvent was further removed under a purified N2
standard method (20). All analyses were carried out in tripli-
stream until the volume was reduced to 0.5 mL. The volatile
cate. An Agilent model 5890 GC equipped with a 30 m x 0.25
samples obtained from caper buds and leaves were stored at
mm (df = 0.25 µm) DB-1 bonded-phase fused-silica capillary
5°C until analyzed.
column (J&W Scientific, Folsom, CA) and a FID were used
Direct sequential extraction of caper samples with
for hexanal analysis. The linear velocity of the He carrier gas
dichloromethane and methanol: Each sample of dried
was 30 cm/s at a split ratio of 20:1. The injector and detector
ground caper buds and leaves (200 g) was mixed with 100 mL
temperatures were 300°C and 280°C, respectively. The oven
dichloromethane in a 500 mL Erlenmeyer flask. The flask was
temperature was programmed from 40°–120°C at 10°C/min
shaken in a shaking water bath at room temperature for 7 h.
and held for 3 min.
After the solution was filtered, the filtrate was concentrated
DPPH radical scavenging assay: The radical scavenging
by a rotary flash evaporator at 50°C under reduced pressure.
activity of the samples against stable DPPH (1,1-diphenyl-2-
The residual materials were placed in a 500 mL Erlenmeyer
picrylhydrazyl hydrate) was determined by a Hewlett Packard
flask and 100 mL methanol was added. The flask was shaken
8452A Diode Array Spectrophotometer. The change in color
in a shaking water bath at room temperature for 7 h. After
(from deep violet to light yellow) caused by a donation of
the solution was filtered, the filtrate was concentrated by a
hydrogen from an antioxidant to DPPH was measured at 517
rotary flash evaporator at 50°C. The samples obtained from
nm. The radical scavenging activity of samples was measured
caper buds and leaves were stored in dark containers at -18°C
according to a previously reported method (21).
until analyzed.
Various concentrations of each sample (50, 100, 200 and
Identification of volatile compounds: Volatile compounds
500 µg/mL methanol) were added to solutions (1 mL) of DPPH
in the samples were identified by comparison with the Kovats
in methanol. The mixtures were shaken vigorously and left to
gas chromatographic retention indices (15) and by the mass
stand at room temperature for 30 min. The absorbance of the
spectral fragmentation pattern of each component compared
resulting solutions was measured spectrophotometrically at
with those of authentic compounds. The identification of the
517 nm. The solution of DPPH in methanol (6 x 10–5 M) was
GC components was also conducted with NIST AMDIS ver-
prepared daily, before UV measurements.
sion 2.1 software.
An Agilent model 6890 GC equipped with a 30 m x 0.25
Results and Discussion
mm (df = 0.25 µm) DB-5 bonded-phase fused-silica capillary
column (J & W Scientific, Folsom, CA) and a flame ionization Volatile compounds identifed in the oils from caper
detector (FID) was used for routine analysis of the volatile buds and leaves: The yield of oils (relative to the dry caper
compounds. The injector and the detector temperatures sample) were 0.30 ± 0.1% from caper buds and 0.20 ± 0.0%
were 200ºC and 250ºC, respectively. The oven temperature from caper leaves obtained from the samples with steam distil-
was programmed from 35°–220ºC at 3ºC/min and held for lation followed by dichloromethane extraction; 1.5 ± 0.1% from
40 min. The linear He carrier gas velocity was 29 cm/s at the caper buds and 1.20 ± 0.1% from caper leaves obtained from
splitless mode. the samples with dichloromethane extraction; and 4.2 ± 0.3%
An Agilent model 6890 GC interfaced to an Agilent 5791A from caper buds and 3.2 ± 0.2% from caper leaves obtained
mass selective detector (GC/MS) was used for mass spectral from the samples with methanol extraction. The values are
identification of the GC components at MS ionization voltage mean ± SD (n = 3).
of 70 eV. A 30 m x 0.25 mm (df = 0.25 µm) DB-5 bonded-phase Table I shows the volatile compounds identified in the
fused-silica capillary column (J&W Scientific, Folsom, CA) was samples obtained from caper buds and leaves with steam
used for GC. The linear velocity of the He carrier gas was 30 distillation followed by solvent extraction. The numbers of
cm/s. The injector and the detector temperatures were 200°C compounds identified were 86 from the caper bud extract and
and 250°C, respectively. The oven temperature was programmed 100 from the caper leaf extract. The major volatile compounds
from 35°–220°C at 3°C/min and held for 40 min. found in caper buds were benzyl alcohol (20.4%), furfural
Aldehyde/carboxylic acid assay for antioxidative activ- (7.4%), ethanal methyl pentyl acetal (5.9%), 4-vinyl guaiacol
ity: Antioxidative activities of the samples were tested using (5.3%), thymol (5.1%), octanoic acid (4.8%) and methyl

Vol. 19, January/February 2007 Journal of Essential Oil Research/73

 El-Ghorab et al.

Table I. Volatile compounds identified in essential oil from caper buds and leaves

GC peak area % in GC peak area % in

Compound RIa Buds Leaves Compound RIa Buds Leaves

methanethiol 525 0.1 0.2 hexanoic acid 1047 3.2 0.4
acetonitrile 527 0.1 0.3 cis-linalool oxide 1052 0.1 1.6
methyl isocyanideb 530 0.1 0.1 guaiacol (2-methoxy-phenol) 1071 1.2 2.0
methyl isothiocyanate 714 4.5 20.0 (E,E)-3,5-octadien-2-oneb 1076 0.1 1.7
ethyl thiocyanate 718 1.5 1.6 tetramethylpyrazine 1078 0.1 0.8
2-pentenolb 721 0.1 0.2 hexanal diethyl acetal 1082 0.2 1.1
hexanal 775 0.2 0.1 linalool 1092 2.5 0.4
furfural 798 7.4 1.1 isophorone (3,5,5-trimethyl
octane 800 1.3 0.2 2-cyclohexene-1-one) 1102 0.7 0.7
ethyl 2-hydroxypropionate 801 0.2 0.1 2-phenylethyl alcohol 1116 2.0 0.3
dimethyl sulfoxide 807 0.3 0.5 dipropyl disulfide 1140 0.1 0.5
isopropyl isothiocyanate 814 0.1 0.2 karahanaenone (2,2,5-trimethyl
ethyl methyl disulfide 821 0.6 0.1 4-cycloheptene-1-one) 1159 0.1 1.9
(E)-2-hexenal 833 3.3 0.1 2,4-dimethylbenzaldehyde 1166 0.1 0.2
(Z)-3-hexenol 835 0.8 0.3 4-propyl-anisole (4-propyl
furfuryl alcohol 851 0.2 1.0 methoxybenzene) 1184 0.4 0.1
2-ethyl thiophene 868 0.3 0.5 2-phenylethyl acetate 1193 0.1 1.2
isovaleric acid 869 - 0.2 benzoic acid 1200 - 0.2
γ-butyrolactone 870 - 0.5 3-phenylpropanol 1219 1.5 0.6
dimethylsulfone 872 - 0.1 octanoic acid 1237 4.8 2.5
heptanal 873 - 0.4 cinnamic aldehyde (3-phenyl
3-methyl thiopropanal 875 - 0.2 2-propenal) 1241 0.6 1.1
cyclohexanone 876 - 0.3 thymol 1275 5.1 15.5
butanal diethyl acetal 879 - 0.4 cis-theaspirane (cis-tetramethyl
2-heptanol 880 - 0.1 1-oxaspiro-6-decene) 1294 0.5 1.6
2-heptanone 884 0.7 0.3 4-vinyl guaiacol (4-ethenyl
2-ethyl pyrazine 889 0.2 0.7 2-methoxy phenol) 1306 5.3 4.3
2,3-dimethyl pyrazine 897 0.3 0.2 trans-theaspirane 1310 0.1 2.6
butyl isothiocyanate 906 0.1 0.5 2-methyl 1-benzopyran-4-oneb 1316 1.0 0.5
(E)- or (Z)-2-heptenal 912 1.6 0.2 decanoic acid 1335 0.1 0.3
benzaldehyde 915 0.9 0.2 2,5-bis(1-methyl ethyl)phenolb 1356 - 0.1
isobutyl isothiocyanate 919 0.2 0.3 vanillin (4-hydroxy-3-methoxy
6-methyl 5-hepten-2-one 928 0.1 0.5 benzaldehyde) 1359 2.2 2.3
2-propyl thiophene 934 0.3 0.1 benzyl isovalerate 1359 - 0.4
isopentanal diethyl acetal 936 - 0.2 (Ε)-α-ionone 1416 0.1 0.4
dimethyl trisulfide 946 0.2 0.2 dodecanol 1455 0.1 0.4
heptanol 954 - 0.3 (Ε)-β-ionone 1489 0.1 0.1
(E)-salvene [6-methyl frambinone [4-(4-hydroxy
5-methylene-(E)-2-heptene] 956 2.4 - phenyl)-2-butanone] 1512 0.1 0.8
ethanal methyl pentyl acetal 961 5.9 0.2 frambinyl alcoholb 1535 0.4 1.8
phenol 966 - 0.2 vanilic acid (4-hydroxy-3-methoxy
furfural diethyl acetal 966 3.5 0.2 benzoic acid) 1597 0.1 2.8
N-methyl pyrrole-2- 5,6,7,7a-tetrahydro-4,4,
carboxaldehydeb 976 0.1 0.1 7a-trimethyl 2-benzofuranoneb 1600 0.1 1.0
3-octanol 984 1.0 1.7 zingerone [4-(4-hydroxy-3-methoxy
2-acetylpyrazine 994 - 1.0 phenyl)-2-butanone] 1645 0.9 0.2
hexyl acetate 999 0.1 3.6 dodecanoic acid 1673 0.2 0.2
phenylacetaldehyde 1005 0.5 0.3 4-(3-hydroxy-2-methoxyphenyl)-2-
2-methyl-2-pentenoic acid 1011 0.3 0.7 butanone 1767 0.2 0.1
2-ethylhexanol 1016 0.2 0.5 methyl hexadecanoate 1935 0.1 0.1
benzyl alcohol 1043 20.4 1.0 cyclo-octasulfur 2113 0.1 -
tricosane 2300 0.1 -

Kovats Index on DB-5; btentatively identified due to lack of authentic compound

a

74/Journal of Essential Oil Research Vol. 19, January/February 2007

 C. ovata

isothiocyanate (4.5%). The major volatile compounds found
in caper leaves were methyl isothiocyanate (20.0%), thymol
(15.5%), 4-vinyl guaiacol (4.3%), hexyl acetate (3.6%) and
trans-theaspirane (2.6%).
The presence of high levels of benzyl alcohol in caper bud
oil may be related to the presence of many benzene derivatives.
The high level of methyl isothiocyanate in caper leaf oil may
come from isothiocyanate glucosides found in caper leaves (22).
Also, many isothiocyanate compounds were found in both bud
and leaf oils. Many aromatic compounds with characteristic
fragrances were found both in bud and leaf oils. For example,
guaiacol has been used in certain floral perfume compounds
as well as in flavor compounds for imitation coffee, vanilla, and
many fruit and spice complexes (23). Vanillin, which possesses
a sweet creamy flavor, has been widely used in many flavor
compounds, including butter, chocolate, ice cream, root-beer
and cream-soda (23). The numbers of terpenes found were
rather low, but thymol, which has been used in flavorings in
toothpaste, cough drops, mouth washes and chewing gums,
was present in high levels (5.08% in bud oil and 15.50% in
leaf oil). Therefore, these oils could be a source of flavor and
fragrance materials.
Results of the aldehyde/carboxylic acid assay: The
antioxidative activities of samples were examined using a previ-
ously reported aldehyde/carboxylic acid assay (23–26). Figures
1 and 2 show the relative amounts of hexanal remaining in
samples with caper bud oil and leaf oil, respectively, over 40
(Hexanal/Internal standard)
GC peak area ratio
days. The values are mean ± standard deviation (n = 3). Hexanal
without oil (control) oxidized into hexanoic acid over 98% after
40 days. Samples with other extracts show consistent patterns
with these figures. Therefore, the inhibitory effects of samples
were discussed using only the results from after 40 days.
Figure 3 shows the inhibitory effects of various samples
from caper buds (A) and caper leaves (B). In the case of
samples from caper buds, dichloromethane extracts exhibited
the highest activity, inhibiting hexanal oxidation by 92 ± 6.0%
at the 200 µg/mL level over 40 days. Both extracts with dichlo-
romethane and methanol inhibited hexanal oxidation nearly
90% at the 50 µg/L level. The oils from caper buds exhibited
somewhat lower activities than those of dichloromethane and
methanol extracts. However, it inhibited hexanal oxidation by
64 ± 5.8% and 86.2 ± 9.3% at the 50 µg/mL level and the 200
µg/mL level, respectively.
The activities from different caper leaf samples (B) showed
similar results to those of the samples from caper buds. In the
cases of the dichloromethane extract and methanol extract,
the lowest level tested (50 µg/mL) exhibited the highest ef-
fect (93.9 ± 5.3% and 93.8 ± 4.1%, respectively). On the other
hand, the sample with the oil showed the lowest activity at the
same level (60.2 ± 2.0%).
Results of the scavenging effect on the DPPH radical:
Figure 4 shows the results of radical scavenging activities by
the samples from caper buds (A) and leaves (B). All samples
exhibited dose-response activity. The methanol extracts exhib-
ited the greatest scavenging activities among three different

A
BHT (50 µg/mL)

Methanol 200 µg/mL

extract
100 µg/mL

50 µg/mL
Dichlormethane
extract

Essential
oil
Figure 1. Relative amounts of hexanal remaining in
samples with essential oil from caper buds over 40 days
0 20 40 60 80 100

B
BHT (50 µg/mL)

Methanol
(Hexanal/Internal standard)

extract
GC peak area ratio

Dichlormethane
extract

Essential
oil

0 20 40 60 80 100
Inhibitory Effect (%)

Time (days)
Figure 3. Inhibitory effects of caper bud (A) and leaf (B)
Figure 2. Relative amounts of hexanal remaining in samples measured by the aldehyde/carboxylic acid assay
samples with essential oil from caper leaves over 40 days after 40 days

Vol. 19, January/February 2007 Journal of Essential Oil Research/75

 El-Ghorab et al.

Phenolic compounds are well known to exhibit antioxidant

A activity (30, 31). Therefore, the antioxidative activities of the
BHT (50 µg/mL) oils both from caper buds and leaves are partially due to the
presence of phenolic compounds, such as guaiacol, 4-vinyl
Methanol
extract
guaiacol, thymol and vanillin. Also, thymol inhibited hexanal
500 µg/mL oxidation by 100% at the level of 50 µg/mL over 40 days (28).
200 µg/mL Benzyl alcohol inhibited hexanal oxidation by 82% at the level
Dichlormethane
extract
100 µg/mL of 500 µg/mL (16).
50 µg/mL Heterocyclic compounds are classified as artifact compo-
nents formed by heat treatment in the essential oils. However,
Essential
oil some heterocyclic compounds have appreciable antioxidant
activity. For example, furfural inhibited hexanal oxidation by
0 20 40 60 80 100 70% at the level of 500 µg/mL for 40 days (24). Also, N-methyl
B pyrrole-2-carboxaldehyde and 2-ethylthiophene inhibited
BHT (50 µg/mL)
hexanal oxidation by 95% and 100%, respectively, at the level
of 500 µg/mL for 40 days (24).
Methanol
Extracts from dichloromethane and methanol were not ana-
extract lyzed. However, the antioxidant activities of these extracts—in
particular, methanol extracts—might be due to polyphenols,
Dichlormethane
which are not readily recovered by steam distillation or dichlo-
extract romethane extraction.
The results from the present study suggest that caper buds
and leaves can be used as a source of fragrance compounds
Essential
oil and as medicinal plants.

0 20 40 60 80 100
Inhibitory Effect (%)
Figure 4. Inhibitory effects of caper bud (A) and leaf (B)
samples measured by the DPPH assay
samples—94.6 ± 3.2% from bud samples at the 500 µg/mL
level, and 99.6 ± 1.3% from leaf samples at the 500 µg/mL level.
The methanolic extract of Capparis spinosa has been reported
to show strong antioxidant activity (27). The oils of buds and
leaves exhibited 88.5 ± 0.1% and 73.5 ± 0.1%, respectively,
at the 500 µg/mL level. In the case of samples from caper
buds, the dichloromethane extracts exhibited the lowest level
of activity among the three different samples—75.1 ± 4.8%
at the 500 µg/mL level. On the other hand, the oil samples
from caper leaves showed the lowest level of activity among
the three different samples.
Antioxidant activities of samples: It is generally recog-
nized practice to use two different methods for the investiga-
tion of antioxidant activities of samples. Two different methods
exhibited consistent antioxidant activities in the present study.
The above results demonstrated that the different extracts of
caper buds and leaves are effective as hydrogen donors and as a
primary antioxidant by reacting with the lipid radicals. This may
be responsible for the main cause of suppression of autoxidation
in the aldehyde/carboxylic acid and the DPPH assays.
There have been many reports on the antioxidative activities
of essential oils from various plants, including beans (18, 19),
clove buds (16), eucalyptus (17), teas (28) and thyme leaves
(29). The oils from caper buds and leaves also exhibited anti-
oxidative activities. It is difficult to pinpoint the compounds
giving antioxidant activities to the samples because these oils
contained numerous compounds. However, some compounds
identified in the present study have been reported to possess
antioxidant activity.
76/Journal of Essential Oil Research
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