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The present study attempts to explore the phytochemical constituents of different extracts from Cynara cornigera and Cichorium endivia plant materials. The two species studied are native in Egypt. Five different solvents, viz., aqueous, methylene chloride, petroleum ether, ethyl acetate, and n-butanol were used. Phytochemical analysis revealed the presence of phenols, flavonoids, sterols (stigmasterol and beta-sitosterol), terpenes (α-amyrin, ursolic and oleanolic acid), and hydrocarbons (n-alkane), the latter found in low amount. The ethyl acetate and water extracts of C. cornigera root showed lower mass fractions of phenolic compounds ranged from 20 to 81 g/100 g, and higher amounts in ethyl acetate extract of the inflorescences and butanol extract of the root where values ranged from 195 to 399 g/100 g. The β-sitosterol and stigmasterol were present in all plant extracts. Oleanolic and ursolic acids were detected in roots, leaves and inflorescences of C. cornigera and in C. endivia shoot. The ethyl acetate extracts from C. cornigera leaf and inflorescence attained higher chemical diversity than the other extracts. Alternatively, sterols and triterpenes were the major constituents. The high chemical diversity of active constituents justifies the future potential use of the two species at commercial level.
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Acta Biologica Hungarica 66(1), pp. 103–118 (2015)
DOI: 10.1556/ABiol.66.2015.1.9
0236-5383/$ 20.00 © 2015 Akadémiai Kiadó, Budapest
AhmAd K. hegAzy,1,2 * Shahira M. Ezzat,3 iMan B. QaSEM,4
MohaMEd S. ali-ShtayEh,5
MohaMMEd o. BaSalah,1 haySSaM M. ali1 and aShraf a. hataMlEh1
1Department of Botany and Microbiology, College of Science, King Saud University,
Riyadh 11451, Saudi Arabia
2Department of Botany, Faculty of Science, Cairo University, Giza 12613, Egypt
3Department of Pharmacognosy, Faculty of Pharmacy, Cairo University, Cairo 11562, Egypt
4Biodiversity and Environmental Research Center (BERC)/ Til, POB 696 Nablus, West Bank, Palestine
5Department of Biology, Faculty of Science, An-Najah University, West Bank, Palestine
(Received: February 25, 2014; accepted: June 16, 2014)
The present study attempts to explore the phytochemical constituents of different extracts from Cynara
cornigera and Cichorium endivia plant materials. The two species studied are native in Egypt. Five dif-
ferent solvents, viz., aqueous, methylene chloride, petroleum ether, ethyl acetate, and n-butanol were
used. Phytochemical analysis revealed the presence of phenols, avonoids, sterols (stigmasterol and beta-
sitosterol), terpenes (α-amyrin, ursolic and oleanolic acid), and hydrocarbons (n-alkane), the latter found
in low amount. The ethyl acetate and water extracts of C. cornigera root showed lower mass fractions of
phenolic compounds ranged from 20 to 81 g/100 g, and higher amounts in ethyl acetate extract of the
inorescences and butanol extract of the root where values ranged from 195 to 399 g/100 g. The
β-sitosterol and stigmasterol were present in all plant extracts. Oleanolic and ursolic acids were detected
in roots, leaves and inorescences of C. cornigera and in C. endivia shoot. The ethyl acetate extracts from
C. cornigera leaf and inorescence attained higher chemical diversity than the other extracts.
Alternatively, sterols and triterpenes were the major constituents. The high chemical diversity of active
constituents justies the future potential use of the two species at commercial level.
Keywords: Sterols – triterpenes – avonoids – phenolic acids – Egypt
The increasing use of plant extracts in food, cosmetic and pharmaceutical industries
suggests a systematic study of medicinal plants around the world [49]. Biotic and
abiotic stresses exert a considerable inuence on the secondary metabolite pool espe-
cially the qualitative and quantitative phenolic composition [1]. Polyphenols when
associated with various carbohydrates and organic acids exhibit a wide range of
pharmaceutical properties including antiallergic, antiatherogenic, antiinammatory,
antimicrobial, antioxidant, antithrombotic, cardioprotective, antioxidants, and vasodi-
latory effects [2, 5, 36].
* Corresponding author; e-mail address:
104 AhmAd K. hegAzy et al.
Acta Biologica Hungarica 66, 2015
The wild cichory or endive, Cichorium endivia L. (Asteraceae) is a Mediterranean
perennial herb indigenous to Europe, Western Asia and North Africa [17]. The genus
Cichorium comprises seven species native to the Mediterranean basin [42]. Strong
antioxidant activities were found in the polyphenolic fraction of two Cichorium vari-
eties; Cichorium endivia var. crispum and var. latifolium [41], where both varieties
contain chlorogenic acid derivatives [14, 26]. Alternatively, different active constitu-
ents of other Cichorium spp. were reported [27, 36a], and few other studies reported
different active constituents and medicinal uses of Cichorium endivia [29, 45, 54].
The wild artichoke, Cynara cornigera Lindl. (Asteraceae) is a perennial herba-
ceous species, originating from the Mediterranean region. The species is widely cul-
tivated for economic purposes all over the world [15]. Cynaroside, apigenin-7-O-
glucoside, and scolymoside and two sesquiterpens, viz., grosheimin and solstitalin A
were identied from the leaf extracts [6, 15, 52, 57]. Extracts from C. scolymus are
used in folk medicine against liver complaints and to improve liver regeneration after
partial hepatectomy [9, 19]. Flower head of C. cornigera is eaten as a vegetable and
prepared for different value-added products such as salad, concentrate, and canned
beverages [56]. The avonoid kaempferol 3-O-(6-O-malonyl) was reported from the
root extracts of the two species [14].
Considering the reported chemical constituents in other species of Asteraceae, this
study decided to screen for additional secondary metabolites that might be present in
the wild cichory and artichoke native to Egypt. The aim is to explore the active con-
stituents in the two species, particularly the phenolic compounds, terpenes and steroid
Plant extracts
Plant materials were collected from wadi Habis, about 30 km west of Matrouh city,
Mediterranean coast, Egypt. Individual plants were excavated and separated into dif-
ferent organ components, viz., roots, stems, leaves and inorescences (ower heads)
for wild artichoke and whole plant phytomasss for wild cichory. The plant materials
were cut into pieces and air-dried in shade at room temperature. The dry material (792
gm) of wild cichory; and leaves (675 gm), roots (864 gm) and ower heads (630 gm)
of wild artichoke were ground into powder. Extraction was performed in 90% ethyl
alcohol at room temperature till exhaustion, and was then concentrated under reduced
pressure to dry at 40 °C using a rotary evaporator. Materials were subjected to suc-
cessive extraction with petroleum ether, methylene chloride, ethyl acetate, and
n-butanol using separating funnel. The solvents were used in the order to increase
polarity. The residue obtained from each solvent was dried and weighed. The extracts
were kept at 4 °C till used for phytochemical screening.
Phytochemical components in Cichorium and Cynara 105
Acta Biologica Hungarica 66, 2015
Phenolic compounds
Qualitative and quantitative determinations of phenolic compounds were carried out
according to Dimitrios et al. [12]. The retention time (RT) of the compounds isolated
from C. endivia and C. cornigera was compared with that of corresponding standards
under the same conditions and further conrmed by co-injection with isolated stand-
ards. The compounds were then injected to a High Performance Liquid Chromatography
(HPLC) system at the same time as the solvent extracts and the chromatogram was
run with a gradient of CH3OH in acetic water (10 to 90% CH3OH in water in the
presence of 5% CH3COOH). Throughout the experiment each peak detected in the
range from 254 to 280 nm in 30 min at 20 °C corresponded, as a rule, to a single
molecule. Most compounds exhibited absorption peaks in the low-wavelength region
245 nm.
All the HPLC samples (one gram each) were prepared by extraction with 50 ml
methanol (Lab scan) and sub-coiled condensed for one hour. After evaporation, the
residue was dissolved in methanol to give a nal concentration of 0.0025–0.025%
(w/v). Filtration over acrodisc-CR removed the insoluble particles. The samples were
analysed at room temperature (20 °C) in a Brucker LC 42 (Brucker Franzen Analytic
Gmbh) whith UV diode array detection, LC 21 pump, LC 51 automatic sample ana-
lyzer, LC 211 oven, using a spherisorb C16 ODS column, 5 µm , 250 mm × 4.6 mm
(Bischoff, Leonberg). The ow rate was 1 ml/min, and the injection volume 5 µl. The
operating system was the Chromstar Data system of the Brucker LC 42 connected to
an Epson computer. Both the height and the area of a well-resolved peak in a chro-
matogram were proportional to the concentration of the compounds detected. For
quantication, either peak height or peak area was used.
Lipids and triterpenes
Plant extracts were used for the investigation of lipid and triterpene contents using
Unicam Pro-GC with [(Column: 3%OV-17(Methyl phenyl Silicone) on chromosorb-
WHP); (Mesh: 100–120) and (Dimensions: 1.5 × 4 mm)]. The percentage composi-
tion of the extracts was computed from GC peak areas without correction factors.
Qualitative analysis was based on a comparison of retention times, indices and mass
spectra with the corresponding data base. The condtions of GC used are shown in
Table 1.
Table 1
Separation conditions of unsaponiable matters during GC analysis
Temperature Programing Gases Flow Rate
temperature Rate Final
temperature Final
time Injector Detector N2H2Air
70 °C 10 °C/min 270 °C 50 min 250 °C 300 °C 30 ml/min 33 ml/min 330 ml/min
106 AhmAd K. hegAzy et al.
Acta Biologica Hungarica 66, 2015
The quantication of Oleanolic acid (OA) and Ursolic acid (UA) followed the
method described by Wang et al. [53]. Standard solutions of OA and UA were pre-
pared in nal concentration of 25 µg/ml of each compound. The petroleum ether
extracts were dissolved in 5 ml methanol then an aliquot of 50 µl extract was diluted
in 5 ml methanol. Sampels of 20 µl were injected in the HPLC apparatus. The peaks
in the chromatogram were identied in comparison to their retention time with the
corresponding standards under the same conditions.
Successive extracts yield
The yield of ethanolic extracts and the sucssive solvent extraction of C. endivia and
C. cornigera are presented in Table 2. The highest yield of C. endivia was obtained
from the ethanolic and water extracts with values 18.95 and 16.47 mg/100 g, respec-
tively. The highest yield from C. cornigera was obtained from the ethanolic extract of
roots (111.22 mg/100 g), followed by leaves (110.24 mg/100 g) and the least amounts
in the ower heads (86.38 mg/100 g). Considering the order of extract dependent yield
in C. cornigera, the order of root extract yield was ethanol > water > ethyl acetate >
n-butanol > methylene chloride > petroleum ether, while for leaf and ower the yields
were ethanol > water > n-butanol > ethyl acetate > methylene chloride > petroleum
Phenolic compounds and avonoids
Twenty phenolic compounds were detected in the two study species, eight avonoids,
viz., Catechin, apigenin, luteolin, luteolin-3-methoxy-7-rutinoside, rutin, quercetin,
chrysin and 5-7-dihydroxy-4-methisoavone and 12 phenolic acids (Tables 3 and 4).
Table 2
The yield (mg/100 g) of Cichorium endivia and Cynara cornigera extracts obtained
by the different solvents
Total extract of dry plant material
Dry weight
(g) Ethanol Petroleum
ether Methylene
chloride Ethyl
acetate n-Butanol Water
C. endivia 812 18.95 0.12 0.56 0.44 1.34 16.47
C. cornigera
roots 675 111.22 0.06 0.19 1.14 1.13 108.68
C. cornigera
leaves 864 110.24 0.05 0.59 1.13 1.96 106.48
C. cornigera
ower heads 630 86.38 0.05 0.40 1.48 1.85 84.44
Values rounded to the nearest two decimals.
Phytochemical components in Cichorium and Cynara 107
Acta Biologica Hungarica 66, 2015
Table 3
Retention time (min) and percentage (%) of phenolic compounds in Cynara cornigera extrcts
Ethyl acetate
(Flower head) Ethyl acetate
(Leaf) Ethyl acetate
(Root) n-Butanol
(Root) Water
Retention time
(min) %Retention time
(min) %Retention time
(min) %Retention time
(min) %Retention time
(min) %
Gallic acid 14.38 0.09 ND ND ND ND 14.68 0.14 14.68 8.52
Pyrogallic ND ND ND ND 17.87 0.11
Chlorogenic acid 22.02 1.75 ND ND ND ND ND ND ND ND
Resorcinol ND ND ND ND ND ND 22.80 1.11 22.43 5.55
Catechin 23.59 0.42 23.87 2.10 ND ND 23.83 3.60
p-Hydroxy benzoic acid 26.39 12.41 26.27 0.69 ND ND ND ND 26.41 1.23
rutinoside ND ND 27.01 2.46 26.89 1.30 27.06 0.17 ND ND
Caffeic acid 29.40 4.40 29.34 2.25 29.49 8.86 29.6 12.65 29.51 1.81
Vanillin 29.88 0.42 30.00 26.37 30.04 23.03 29.83 16.74 30.15 0.80
Ferulic acid 30.96 2.87 30.98 4.82 ND ND 30.86 16.33 ND ND
Rutin ND ND 31.53 0.23 31.47 4.81 ND ND ND ND
Phenol 32.16 0.95 32.16 7.70 32.21 2.12 32.22 0.41 32.25 0.36
p-Coumaric acid 32.39 4.07 32.72 1.33 ND ND ND ND ND ND
Luteoline ND ND 34.30 0.15 34.88 0.30 34.42 0.05 ND ND
Quercetin 36.32 0.57 36.54 2.71 36.44 1.67 ND ND 36.63 0.16
Salicylic acid ND ND 37.53 0.43 ND ND 37.35 1.11 ND ND
Euganol ND ND ND ND ND ND 41.44 0.03 ND ND
5,7-Dihydroy 4-methoxy
isoavone 43.68 0.35 43.60 0.38 43.49 0.63 ND ND ND ND
Chrysin ND ND ND ND ND ND ND ND 44.24 1.80
Values rounded to the nearest two decimals. ND = Not detected.
108 AhmAd K. hegAzy et al.
Acta Biologica Hungarica 66, 2015
All plant organs contained phenolic compounds in different concentrations, ranging
between 0.01 and 135.63 mg/100 g (Table 5). Ethyl acetate extracts displayed more
phenolic content (0.476–135.63 mg/100 g), while that of the water and n-butanol
extracts, only approached 38.03 mg/100 g, and 84.89 mg/100 g, respectively.
Only in the butanol root extract of C. cornigera the presence of euganol and pyro-
gallic acid was observed. Chlorogenic acid, ferulic acid, phenol and p-coumaric acid
were detected in the organic solvent extracts, while were absent in the aqueous
extract. Signicant amounts of chlorogenic acid, p-hydroxyl benzoic acid, p-coumar-
ic acid, caffeic acid, and ferulic acid were detected in ethyl acetate extract of the
ower heads, with values 135.63, 121.17, 56.66, 28.22 and 22.76 mg/100 g, respec-
tively. Caffeic acid, vanillin, phenol, and quercetin were present in all C. cornigera
Table 4
Retention time (min) and percentage (%) of phenolic compounds of Cichorium endivia extracts
Ethanol Ethyl acetate Water
Retention time
(min) %Retention time
(min) %Retention time
(min) %
Gallic acid 14.657 4.04 ND ND 14.62 6.26
Pyrogallic 17.70 2.33 ND ND 17.72 0.41
Chlorogenic acid 22.03 1.90 ND ND 21.95 0.51
Resorcinol ND ND ND 22.61 2.24
Catechin 23.69 2.10 ND ND 23.94 16.63
p-Hydroxy benzoic
acid 26.71 18.66 26.83 7.62 26.65 0.89
rutinoside ND ND ND ND 26.94 0.58
Caffeic acid 29.40 1.50 ND ND 27.31 0.76
Vanillin ND ND 30.06 1.65 29.69 5.35
Ferulic acid 30.98 0.65 30.96 0.60 ND ND
Rutin 31.23 1.31 ND ND 31.21 0.55
Phenol ND ND 32.02 2.29 ND ND
p-Coumaric acid 32.46 1.15 32.50 0.90 32.41 0.01
Luteoline 34.85 0.09 ND ND 34.73 0.06
Quercetin 36.28 3.10 ND ND ND ND
Salicylic acid 36.98 0.56 ND ND 37.36 0.08
Apigenin ND ND ND ND 39.75 0.06
Euganol ND ND 41.37 0.49 ND ND
4-methoxy isoavone ND ND 43.71 0.50 43.37 0.04
Chrysin 44.050 0.7659 ND ND ND ND
Values rounded to the nearest two decimals. ND = Not detected.
Phytochemical components in Cichorium and Cynara 109
Acta Biologica Hungarica 66, 2015
Table 5
The quantitative determination of phenolic compounds (mg/100 g) in different extracts of Cynara cornigera and Cichorium indivia
Phenolic compound
Cynara cornigera Cichorium indivia
Ethyl acetate Butanol Water Ethyl acetate Water Ethanol
Flower head Leaf Root Root Root
Gallic acid 1.65 ND ND 1.64 5.84 ND 6.05 20.35
Pyrogallic ND ND ND 9.66 ND ND 2.94 86.26
Chlorogenic acid 135.63 ND ND ND ND ND 2.26 44.03
Resorcinol ND ND ND 2.43 7.49 ND 4.27 ND
Catechin 16.99 ND 15.65 ND 5.84 ND 38.03 25.14
p-Hydroxy benzoic acid 121.17 3.24 ND ND 0.49 41.01 0.50 54.45
rutinoside ND 6.92 1.42 0.68 ND ND 0.19 ND
Caffeic acid 28.22 6.93 10.56 53.14 0.47 ND 0.27 2.87
Vanillin 2.67 79.79 27.06 69.31 0.20 5.76 1.93 ND
Ferulic acid 22.76 18.32 ND 84.89 ND 2.64 ND 1.55
Rutin ND 2.22 17.58 ND ND ND 0.62 7.71
Phenol 12.43 48.01 5.14 3.50 0.19 16.41 ND ND
p-Coumaric acid 56.66 8.87 ND ND ND 6.92 0.01 4.81
Luteoline ND 0.63 0.47 0.32 ND ND 0.03 0.23
Quercetin 5.09 11.57 2.77 ND 0.06 ND ND 8.27
Salicylic acid ND 8.27 ND ND ND ND ND ND
Apigenin ND ND ND ND ND ND 0.01 ND
Euganol ND ND ND 0.45 ND 5.96 ND ND
5,7-Dihydroy 4-methoxy
isoavone 1.53 0.79 0.50 ND ND 1.19 0.01 ND
Chrysin ND ND ND ND 0.72 ND ND 2.25
Sum of compounds 404.84 195.61 81.20 255.34 21.33 79.91 57.38 264.76
ND = Not detected.
110 AhmAd K. hegAzy et al.
Acta Biologica Hungarica 66, 2015
organs while gallic acid, luteoline, luteolin-3-methoxy-7-rutinoside, p-hydroxyl ben-
zoic acid, 5-7-dihydroxy-4-methisoavone and ferulic acid detected in three out of
ve extracts of C. cornigera (Table 5).
The avonoid composition including catechin rutin and quercetin was the most
abundant in C. endivia, while chrycin, 5,7-dihydroy 4-methoxy isoavone, luteolin,
luteolin-3-methoxy-7-rutinoside and apigenin detected as traces. On the other hand,
the total avonoids content found in C. endivia was 43.61 mg/100 g and 38.90
mg/100 g in ethanol and water extracts, respectively, followed by ethyl acetate in
C. cornigera root (38.43 mg/100 g).
The order of yield in the most abundant constituents of different C. cornigera
extracts was catechin > luteolin-3-methoxy-7-rutinoside > rutin > quercetin >
5.7-dihydroy 4-methoxy isoavone, followed by, luteolin-3-methoxy-7-rutinoside,
luteoline and chrycin. Flavonoid content ranged from traces to 38.039 mg/100 g
(Table 5). It was abundant in ethyl acetate root extract except for quercetin in leaf
extract and 5,7-dihydroy 4-methoxy isoavone in ower head extract. Total avo-
noids of plant organs are in the order of root (54.59 mg/100 g) > ower head (23.62
mg/100 g) > leaf (22.15 mg/100 g). Luteolin was extremely low in all organs of
C. cornigera and also showed an almost zero level of apigenin. Phenolic compounds
were abundant in ethanolic extract of C. endivia with about 19 out of 20 compounds.
In general, C. cornigera extracts had higher phenol concentration than C. endivia.
The most abundant compounds were pyrogallic acid in the ethanolic extract
(86.26 mg/100 g) and catechin in the aqueous extract of C. endivia (38.03 mg/100 g).
Lipids and triterpenes
The plant extracts contained 22 n-alkane hydrocarbons (Tables 6 and 7). The identi-
ed compounds of methylene chloride formed 75.2–84.7%, where eicosane, octade-
cane, tridecane and heneicosane were found to be the major constituents in C. corni-
gera (Table 6). The petroleum ether fractions of the leaf and root were present in quite
similar amounts, like the methylene chloride fractions. The amounts of octadecane
(C17, C18) and tridecane were signicantly higher in the roots (13.97, 12.18 and
11.85%, respectively) than ower heads (4.41, 5.77% and 4.54%, respectively), fol-
lowed by leaves. The amount of eicosane was higher in leaves (18.99%) than in the
ower heads (10.27%). Petroleum ether extract of the ower heads contained eight
compounds higher than the leaves & roots which were characterized by high content
of eicosane, C18 and docosane (18.02, 16.6 and 11.7%), while the roots contained
high amounts of tridecane and tetradecane (16.2–11.2%). The identied compounds
in petroleum ether extract constituted 83.4–95.1% of the total content. Octadecane,
eicosane, docosane, tridecane and tetracosane were the major constituents in C. endi-
via (Table 7). The petroleum ether extract contains more hydrocarbons (93.43%) than
the crude ethanol extract (62.60%).
Two sterol compounds were identied as stigmasterol and β-sitosterol. The lowest
contents were measured in the methylene chloride leaf extract. The major sterol
Phytochemical components in Cichorium and Cynara 111
Acta Biologica Hungarica 66, 2015
components in C. cornigera were 4.33% in petroleum ether ower head extract, fol-
lowed by root extract (4.08%) then leaf extract (3.99%). The main component of
methylene chloride extract is α-amyrin found in the ower head (1.36%), followed by
β-sitosterol and stigmasterol (1.35% and 1.30%, respectively). α-Amyrin was not
found in petroleum ether ower head extract, while β-sitosterol was detected in
ower head and root extracts with values1.84% and 1.52%, respectively. Stigmasterol
Table 6
Percentage composition of hydrocarbon and sterol components in Cynara cornigera obtained by GC
Relative %
Root Leaf Flower head
ether Methylene
chloride Petroleum
ether Methylene
chloride Petroleum
ether Methylene
n-Nonane (C9) ND ND ND 4.99 ND 3.26
n-Decane (C10) ND 2.64 1.32 4.95 ND 1.28
n-Henedecane (C11) 1.15 2.22 1.26 2.25 ND 4.67
n-Dodecane (C12) 2.40 2.71 2.07 3.11 ND 6.70
n-Tridecane (C13) 16.19 11.85 4.55 4.23 ND 4.54
n-Tetradecane (C14) 11.17 1.92 7.53 2.06 2.87 2.56
n-Pentadecane (C15) 4.25 1.02 9.34 7.67 7.71 6.72
n-Hexadecane (C16) 1.66 1.32 3.47 3.75 10.43 4.45
n-Heptadecane (C17) 0.73 13.97 1.51 2.88 ND 4.41
n-Octadecane (C18) 12.95 12.18 14.49 4.52 16.63 5.76
n-Nonadecane (C19) 0.65 2.11 0.53 4.23 3.72 3.16
n-Eicosane (C20) 12.92 3.72 12.48 18.99 18.02 10.26
n-Heneicosane (C21) ND 9.50 0.30 4.98 1.21 4.07
n-Docosane (C22) 8.06 2.54 10.10 4.33 11.71 3.17
n-Tricosane (C23) 1.98 ND 0.34 3.37 ND 4.75
n-Tetracosane (C24) 6.96 6.07 7.09 2.91 9.55 2.66
n-Pentacosane (C25) 0.48 1.95 0.52 2.14 ND 2.44
n-Hexacosane (C26) 4.30 3.67 4.30 1.32 5.91 1.77
n-Heptacosane (C27) 0.21 1.24 0.55 1.51 ND 1.75
n-Octacosane (C28) 3.03 2.37 3.48 1.20 3.70 1.29
n-Triacontane (C30) 0.32 ND 2.55 ND ND 1.90
n-Hentriacontane (C31) ND ND 1.54 ND 1.23 ND
Total 89.50 83.09 89.42 85.50 92.75 81.66
Sterols and triterpene
α-Amyrin 0.36 0.90 0.49 0.71 ND 1.32
β-Setosterol 1.52 0.68 0.45 0.96 1.84 1.35
Stigmasterol 2.19 1.20 3.05 0.19 2.49 1.30
Values rounded to the nearest two decimals. ND = Not detected.
112 AhmAd K. hegAzy et al.
Acta Biologica Hungarica 66, 2015
was high in petroleum ether shoot extract of C. endivia (3.05%), followed by that of
the ower head extract (2.49%) and root extract (2.19%) of C. cornigera.
Two types of triterpenes were detected in both C. cornigera and C. endivia
extracts. Petroleum ether extract of C. cornigera ower heads showed the highest
amount (54.7%) of oleanolic acid (Table 8), while C. endivia had the highest amount
of ursolic acid (88.5%) (Table 9).
Table 7
Percentage composition of hydrocarbon and sterol components
in Cichorium endivia obtained by GC
Hydrocarbons Relative %
Ethanol Petroleum ether
n-Octane (C8) ND 2.59
n-Nonane (C9) ND 7.44
n-Decane (C10) ND 9.24
n-Henedecane (C11) 10.72 11.12
n-Dodecane (C12) 5.20 8.71
n-Tridecane (C13) 1.70 7.38
n-Tetradecane (C14) 2.29 5.85
n-Pentadecane (C15) 4.01 ND
n-Hexadecane (C16) 2.15 7.38
n-Heptadecane (C17) 2.88 0.37
n-Octadecane (C18) 3.80 7.51
n-Nonadecane (C19) 2.11 ND
n-Eicosane (C20) 4.19 5.77
n-Heneicosane (C21) 2.75 1.67
n-Docosane (C22) 1.41 4.62
n-Tricosane (C23) 1.93 ND
n-Tetracosane (C24) 5.68 4.20
n-Pentacosane (C25) 1.45 3.40
n-Hexacosane (C26) 6.03 1.30
n-Heptacosane (C27) 2.51 2.48
n-Octacosane (C28) 3.65 1.69
n-Triacontane (C30) ND 0.63
n-Hentriacontane (C31) ND ND
Total 93.43 62.60
Sterols and triterpene
α-Amyrin 11.33 1.17
β-Setosterol 6.76 0.97
Stigmasterol 3.27 1.61
Values rounded to the nearest two decimals. ND = Not detected.
Phytochemical components in Cichorium and Cynara 113
Acta Biologica Hungarica 66, 2015
The results of phenolic compounds and avonoids showed that apigenin was not
detected in the extracts of C. cornigera, while traces of chrysin was found in water
extract of the root. These two compounds are reported here for the rst time in the
two species studied. Apigenin and luteolin were identied in C. cardunculus [31].
The chlorogenic acid was identied in the aqueous and alcoholic extracts of Aster
ageratoides ower buds [11].
The results indicate that C. cornigera organs, especially the ower heads could
represent an important source of polyphenols with therapeutic activity [34].
According to Gupta et al. [22], avonoids are generally found in substantial concen-
trations in plant leaves or owers. Brás et al. [8] reported the presence of quercetin
and rutin in the leaves of Eupatorium littorale (Asteraceae). Twelve biologically
active avonoids, mainly avonol and avone derivatives, including two glycosides
were detected in the glandular trichomes of Chromolaena species [25], while a total
of 135 different compounds were reported from the Cichorieae (Lactuceae) tribe of
the Asteraceae [44]. In C. cornigera and C. endivia, the high and variable active
compound concentrations are related to the arid climate conditions, such as, hot tem-
perature, high solar exposure, drought and salinity which stimulate the biosynthesis
of secondary metabolites as polyphenols [13].
The presence of biologically active secondary metabolites such as tannins (gallic
acid and catechin), sterols and terpenes contributes to its medicinal value [47].
Tannins have been reported to have several pharmacological activities such as spas-
Table 8
Retention time (min) and percentage (%) of triterpene compounds in Cynara cornigera extracts
of petroleum ether and ethanol
Cynara cornigera
Root Leaf Flower head
Retention time
(min) %Retention time
(min) %Retention time
(min) %
Oleanolic acid 2.21 1.70 2.60 2.20 0.98 54.70
Ursolic acid 0.98 95.5 0.96 96.3 0.26 32.00
Table 9
Retention time (min) and percentage (%) of triterpene compounds
in Cichorium endivia extracts of petroleum ether and ethanol
Cichorium endivia
Petroleum ether Ethanol
Retention time (min) %Retention time (min) %
Oleanolic acid 2.58 3.40 2.26 4.40
Ursolic acid 0.93 96.60 0.93 88.50
114 AhmAd K. hegAzy et al.
Acta Biologica Hungarica 66, 2015
molytic activity in smooth muscle cells [50]. Gallic acid has antineoplastic and bac-
teriostatic activities and anticancer properties in prostate carcinoma cells [28], and
anti-inammatory and antibacterial activity [46]. The present study revealed that
gallic acid is in range from 1.64 mg/100 g in C. cornigera parts to 20.35 mg/100 g in
C. endivia. There were variations in total phenolic content of different aromatic and
medicinal plants ranging between 6.80–32.10 mg gallic acid/g dry weight bases [4,
21]. p-Coumaric and ferulic acids are also present in combination with betanidin
monoglucoside in fruits of Basella rubra [20]. Hydroxycinnamic acid derivatives
were found in C. endivia var. crispum and var. latifolium; three derivatives
(5-O-caffeoylquinic acid, 3,4-di-O-caffeoylquinic acid, and 5-O-feruloylquinic acid)
were found in both chicories, while 3,5-di-O-caffeoylquinic acid was typical of var.
crispum and cis-caftaric acid of var. latifolium [40].
The presence of kaempferol 3-O-(6-O-malonyl) glucoside in endive is reported
here for the rst time. Methanol extract of Lactuca sativa L. varieties (Romaine,
Iceberg and Baby) and C. endivia L. variety “escarole” have yielded a high phenolic
content, where chicory extracts being the richest with 50 mg phenolics/g of freeze-
dried extract [14, 35]. Tannins, sesquiterpene lactones, cinnamic acid, caffeic and
chlorogenic acids were reported in chicory [27]. Monocaffeoyl tartaric acid, chloro-
genic acid, and chicoric acid were detected in different varieties of Cichorium inty-
bus, while cyanidin 3-O-glucoside, delphinidin 3-O-glucoside, and cyanidin
3-O-glucoside were the main phenolic compounds in the red varieties [26]. Also,
apigenin and apigenin-7-0-α-1-arabinoside were isolated from Cichorium intybus
aerial parts [55].
The p-hydroxybenzoic acid (4-hydroxybenzoic acid) found in C. cornigera
showed a broad range of pharmacological activities, for instance, antifungal, anti-
mutagenic, antisickling, estrogenic and antimicrobial effects [10, 43]. Chlorogonic
acid has been reported to have a number of biological properties, such as antibacte-
rial, antioxidant, hepatocyte protective and antimutagenic activity [51]. Artichoke
capitula was characterized by signicant amounts of chlorogenic acid and various
dicaffeoylquinic esters, especially 1,3-dicaffeoylquinic acid, known as cynarin [7].
Eight phenolic compounds were isolated from n-butanol leaf fraction of Cynara
scolymus which is known for its antimicrobial activity [56, 57]. Also, Orlovskaya et
al. [39] have previously reported qualitative and quantitative results on phenolic com-
pounds on raw material and extracts of C. scolymus leaves. The phenolic contents in
leaf and seed of Cynara cardunculus were similar and two times higher than those in
ower heads [16]. The organic subfraction of artichoke is rich in polyphenolic com-
pounds, with caffeoylquinic acids and avonoids as the major chemical constituent
[32]. In leaf extracts of commercially available artichoke (C. scolymus) a number of
compounds were identied, including 8-deoxy-11-hydroxy-13-chlorogrosheimin,
cryptochlorogenic acid, chlorogenic acid, neochlorogenic acid, cynarin, cynaratriol
(tentatively), grosheimin, 8-deoxy-11,13-dihydroxygrosheimin, luteolin-7-O-rutino-
side, luteolin-7-O-glucoside, and cynaropicrin [18]. Phenolic acids, up to 2%, caffeic
acid, mono- and dicaffeoylquinic acid derivatives, e.g., cynarin, and chlorogenic acid
Phytochemical components in Cichorium and Cynara 115
Acta Biologica Hungarica 66, 2015
were reported to be present in artichoke [24]. The avonoids, triterpenoids and sapo-
nines were reported to possess hepatoprotective activity in animals [3].
As for lipid and triterpene content, twenty-two compounds of the hydrocarbons
were identied in petroleum ether of C. cornigera parts. The major components con-
stitute up to 85% of the plant chemical composition, while the minor components
reported in trace amounts [37]. A high content of derivatives was also characteristic
in C. endivia extracts, including henedecane, decane, dodecane, octane and heptade-
cane. The presence of terpenoids in C. cornigera and C. endivia has also been
reported to show several biological and pharmacological activities such as antioxida-
tive [48], anti-inammatory [38], hepato-protective effects [33]. The mechanism of
action of terpenes is not fully understood but it is speculated to involve membrane
disruption by the lipophilic compounds [23].
In conclusion, our ndings indicate that C. cornigera and C. endivia are rich
sources of eight important biologically active avonoids, twelve phenolic acids, tow
triterpenes and three steroids, which were detected for the rst time in the two species
studied. Considering that chlorogenic acid and rutin are highly valuable natural poly-
phenol compounds used as medical and industrial materials, the identication and
quantication of these main polyphenols in the present study can be important for
potential use at commercial level in the pharmaceutical industry.
We thank the Deanship of Scientic Research, College of Science Research Center, King Saud University,
Riyadh, Saudi Arabia for supporting this publication.
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... C. endivia is a cheap edible plant with a high nutritional value [3] used traditionally as a digestive aid [2], as well as for the treatment of chronic diseases such as rheumatism [5] and diabetes [6]. The plant is known to accumulate terpenoids [7][8][9][10], phenolics [8,9,[11][12][13][14][15][16][17][18][19], and nitrogenous compounds [12,20,21]. In addition, several reports have shown evidence of C. endivia's diverse bioactivities [1,6,12,16,19,[22][23][24][25][26][27]. ...
... They were the triterpenes: stigmasterol, β-amyrin, and ursolic acid; the megastigmane-type norisoprenoid: (6S, 7E)-6-hydroxy-4,7-megastigmadien-3,9dione (S (+)-dehydrovomifoliol) and vomifoliol; the phenolic acids: ferulic, p-coumaric, protocatechuic, vanillic, and 4-hydroxy phenyl acetic acids; the flavonoids: kaempferol and luteolin; and the dicarboxylic acid: azelaic acid. All the isolated compounds were reported previously in the plant [12][13][14][15][16]18,45] except azelaic acid and vomifoliol, which are isolated for the first time from C. endivia. ...
Full-text available
Cichorium endivia L. (Asteraceae) is a wide edible plant that grows in the Mediterranean region. In this study, a phytochemical investigation of C. endivia L. ethanolic extract led to the isolation of stigmasterol (1), ursolic acid (2), β-amyrin (3), azelaic acid (4), vanillic acid (5), (6S, 7E)-6-hydroxy-4,7-megastigmadien-3,9-dione (S(+)-dehydrovomifoliol) (6), 4-hydroxy phenyl acetic acid (7), vomifoliol (8), ferulic acid (9), protocatechuic acid (10), kaempferol (11), p. coumaric acid (12), and luteolin (13). In addition, the total phenolic content as well as the in vitro antioxidant activity of C. endivia L. extract were estimated. Moreover, we inspected the potential gonado-protective effect of C. endivia crude extract, its phenolic fraction, and the isolated coumaric, vanillic, and ferulic acids against methotrexate (MTX)-induced testicular injury in mice. There were seven groups: normal control, MTX control, MTX + C. endivia crude extract, MTX + C. endivia phenolic fraction, MTX + isolated coumaric acid, MTX + isolated vanillic acid, and MTX + isolated ferulic acid. MTX was given by i.p. injection of a 20 mg/kg single dose. The crude extract and phenolic fraction were given with a dose of 100 mg/kg/day, whereas the compounds were given at a dose of 10 mg/kg/day. A histopathological examination was done. The testosterone level was detected in serum together with the testicular content of malondialdehyde (MDA), catalase (CAT), superoxide dismutase (SOD), interleukin 1β (IL-1β), IL-6, tumor necrosis factor alpha (TNF-α), nuclear factor kappa B (NF-κB), B-cell lymphoma 2 (Bcl-2), Bcl-2 associated x protein (Bax), p53, and miR-29a. C. endivia crude extract, the phenolic fraction, and the isolated compounds showed significant elevation in their levels of testosterone, CAT, SOD, Bcl-2 with a significant decrease in their levels of MDA, TNF-α, IL-1β, IL-6, NF-κB, Bax, P53, and miR-29a compared to those of the MTX control group. In conclusion, C. endivia mitigated MTX-induced germ cell toxicity via anti-inflammatory, antioxidant, and antiapoptotic effects.
... Among these, the structurally close related phenolic acids: chicoric, chlorogenic and caffeic (Fig. 12). [91,92,93]. ...
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In the first two parts of this series of review articles, we presented the anticancer and anti-inflammatory activities of the most important wild edible plants of eastern Mediterranean region, which we named as the "Deca-plants" (D-P). In this review article, we will present the antidiabetic activities of these very important plants. Comparing with anticancer and anti-inflammatory activities, the overall antidiabetic activity of the D-P is moderate, but there are clear differences between the ten species. Based on this fact and on the knowledge that the D-P contain several natural products with proven antidiabetic activity, in the discussion section (4), possible future research directions will be indicated. In addition to presenting the reported antidiabetic activity of the plants, some important statistical facts about diabetes will be presented, as well as ethnomedicinal use of these plants for diabetes treatment, in the reviewed region. For the purpose of comparison and comprehensiveness, in the last part of this article, four Non-Deca-Plants with reported antidiabetic activity will be shortly reviewed, when the criteria of selection are wild and edible.
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Plants of genus Cichorium (Asteraceae) can be used as vegetables with higher nutritional value and as medicinal plants. This genus has beneficial properties owing to the presence of a number of specialized metabolites such as alkaloids, sesquiterpene lactones, coumarins, unsaturated fatty acids, flavonoids, saponins, and tannins. Cichorium endivia L., known as escarole, has achieved a common food status due to its nutritionary value, bitter taste, and the presence of healthy components, and is eaten cooked or raw in salads. Presently, wastes derived from the horticultural crops supply chain are generated in very large amounts. Vegetable waste comprises the discarded leaves of food sources produced during collection, handling, transportation, and processing. The external leaves of Cichorium endivia L. are a horticultural crop that is discarded. In this work, the phytochemical profile, antioxidant, and anti-inflammatory activities of hydroalcoholic extract obtained from discarded leaves of three cultivars of escarole (C. endivia var. crispum ‘Capriccio’, C. endivia var. latifolium ‘Performance’ and ‘Leonida’) typical horticultural crop of the Campania region were investigated. In order to describe a metabolite profile of C. endivia cultivars, the extracts were analysed by HR/ESI/Qexactive/MS/MS and NMR. The careful analysis of the accurate masses, the ESI/MS spectra, and the 1H NMR chemical shifts allowed for the identification of small molecules belonging to phenolic, flavonoid, sesquiterpene, amino acids, and unsaturated fatty acid classes. In addition, the antioxidant potential of the extracts was evaluated using cell-free and cell-based assays, as well as their cytotoxic and anti-inflammatory activity. All the extracts showed similar radical-scavenging ability while significant differences between the three investigated cultivars emerged in the cell-based assays. The obtained data were ascribed to the content of polyphenols and sesquiterpenes in the extracts. Accordingly, C. endivia by-products can be deemed an interesting material for healthy product formulations.
The aim of this study is to explore the chemical composition and potentiality (such as antimicrobial, antioxidant and antidiabetic substances) of Cynara cornigera L. shoot system extract harvested from the Turkish Republic of Northern Cyprus. Methanolic extract of C.cornigera shoot system displayed no antibacterial effect on all tested microorganisms. Although the methanolic extract possessed a significant radical scavenging activity for TPC, TFC, DPPH˙, ferric reducing capacity, metal chelating and phosphomolybdenum assay, it did not show any antidiabetic activity. In addition, no essential oil was determined in the chemical composition of the extract. These results indicated that the presence of antioxidant substances of shoot system extract of C. cornigera can be effective against harmful effects of free radicals. Due to this property, its use in human nutrition in Northern Cyprus becomes even more important.
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The relationship between the structural characteristics of 29 flavonoids and their antiradical activity was studied. The obtained results suggest that the free radical scavenger potential of these polyphenolic compounds closely depends on the particular substitution pattern of free hydroxyl groups on the flavonoid skeleton. The possible mechanism of action of flavonoids lacking B ring OHs as free radical scavengers has been proposed.
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Five compounds have been recognized as cynaroside 1, apigenin-7-O-glucoside 2 and scolymoside 3 and two sesquiterpens viz. grosheimin 4 and solstitalinA 5. Their structures were elucidated by spectral methods. Compounds 4 and 5 were isolated from Cynara cornigera for the first time. The antioxidant potential was found to be (89.8%), for EtOAc fraction, (88.46%) for MeOH extract and (74.8%) for mother liquor fraction. Compounds 1 and 3 were isolated as the active principles from the EtOAc fraction with antioxidant activities 90.2, & 90.5% respectively using DPPH° assay comparing to the reference trolox (91.6 %). Compound 2 gave weak activity. No antioxidant activity was noticed for compounds 4 and 5. The EtOAc fraction and the 80% methanolic extract exhibited hepatoprotective activity at a concentration of 12.5 μg/mL. Compounds 1 and compound 3 showed hepatoprotective activity at a concentration of 50 and 25 μg/mL, respectively on using the monolayer hepatocytes assay.
Objective To address the effects of a novel synthetic triterpenoid, 2‐cyano‐3,12‐dioxoolean‐1,9‐dien‐28‐oic acid (CDDO), on the induction of matrix metalloproteinases 1 and 13 (MMP‐1, MMP‐13) by inflammatory cytokines. Methods Human chondrosarcoma cells stimulated with inflammatory cytokines (interleukin‐1β [IL‐1β], tumor necrosis factor α) were used to study the effects of CDDO on the induction of MMPs and the invasion of cells through a collagen matrix. Results CDDO selectively reduced the induction of MMP‐1 and MMP‐13 at the levels of messenger RNA and protein. Treatment with CDDO prior to cytokine stimulation enhanced this inhibition, and we demonstrated that CDDO functions at the level of transcription. Additionally, CDDO reduced IL‐1β–mediated invasion of cells through a collagen matrix. Conclusion This study demonstrates that CDDO is a novel inhibitor of MMP‐1 and MMP‐13 gene expression mediated by inflammatory cytokines. Thus, CDDO may have therapeutic potential for the inhibition of joint degradation in osteoarthritis.
The antifungal activity of methanolic crude extract of Acorus calamus, Tinospora cordifolia and Celestrus paniculatus were investigated against Alternaria solani, Curvularia lunata, Fusarium sp., Bipolaris sp. and Helminthosporium sp. at different concentrations (1000, 2000, 3000, 4000 and 5000 µg/ml). At 5000 µg/ml crude extract of Tinospora cordifolia is found to be highly effective against Helminthosporium sp. followed by Acorus calamus against Alternaria solani. On the other hand at 5000 ug/ml, Celestrus paniculatus showed better activity against Alternaria solani and Helminthosporium followed by Acorus calamus against Alternaria solani at 4000 ug/ml. At 5000 ug/ml, all the three crude extracts showed least activity against fungus Curvularia lunata and Fusarium sp. except Acorus calamus that showed better activity against Curvularia lunata. The increase in the production of phenolics in the extract can be correlated with the induction of resistance in treated plants against phytopathogenic fungi. HPLC analysis of the crude extract of medicinal plants showed six different phenolic acids (Benzoic acid, Cinnamic acid, Caffeic acid, Ferulic acid, Gallic acid and Tannic acid) present in varying amount. The results of the study provide scientific basis for the use of the plant extract in the future development as antioxidant, antibacterial, antifungal and anti-inflammatory agent.
Ion spray mass spectrometry and tandem mass spectrometry of the fresh juice from Basella rubra fruits revealed the presence of betanidin monoglucoside as the major betacyanin and its 4-coumaroyl and feruloyl derivatives as minor components. Co-chromatography (TLC, HPLC) with betacyanin standards identified the betacyanins as gomphrenin I (15S-betanidin 6-O-β-glucoside), gomphrenin II (15S-betanidin 6-O-[6′-O-(4-coumaroyl)-β-glucoside]) together with small amounts of the respective R forms (isogomphrenin I and II) and gomphrenin III (15S-betanidin 6-O-[6′-O-feruloyl-β-glucoside]).
Cynara cardunculus is a diploid (2n=2x=34) species, native to the Mediterranean basin, which belongs to the family of Asteraceae. It includes globe artichoke, cultivated cardoon, as well as their progenitor wild cardoon. The species is a source of biophenols and its leaf extracts have been widely used in herbal medicine as hepatoprotectors and choleretics since ancient times. Globe artichoke leaves have been found to be rich in compounds originating from the metabolism of phenylpropanoids however, to our knowledge, the leaf polyphenolic composition of the two other forms within the species, cultivated and wild cardoon, have not yet been properly investigated. Two main classes of polyphenols have been detected by HPLC/DAD and HPLC/MS analyses: caffeoyl esters and flavonoids. The compounds which are the result of esterification of caffeoylquinic acid moiety with succinic acid, previously detected in other members of the Asteraceae family, were detected in cardoon leaves for the first time.