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The aerial part of Commiphora opobalsamum L. (Burseraceae) growing in Saudi Arabia was subjected to a phytopharmacological investigation in order to identify its major chemical constituents and to evaluate its extracts and isolated compounds in preliminary in vitro assays for antimicrobial, antimalarial, antitumor, anti-inflammatory (COX-2 inhibition), antioxidant and estrogenic activity. Six compounds were isolated and identified as the triterpenes friedelin, canophyllal, and oleanonic acid; the flavonols mearnsetin and quercetin; and syringic acid. The ethyl acetate extract was moderately active against Staphylococcus aureus, Pseudomonas aeruginosa, and Plasmodium falciparum; while the petroleum ether and chloroform extracts inhibited COX-2 at 5 and 10 microg mL(-1), respectively. Of the isolated compounds, syringic acid showed moderate antimalarial, anticandidal, and antimycobacterial activity; while mearnsetin and quercetin exhibited antioxidant activity comparable to ascorbic acid and trolox. This is the first detailed phytochemical investigation of C. opobalsamum L. growing in Saudi Arabia and elsewhere. The isolated compounds are reported from this plant for the first time and their full (1)H and (13)C NMR assignments are included.
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Phytochemical and biological studies on Saudi
Commiphora opobalsamum L.
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Natural Product Research, Vol. 21, No. 5, 1 May 2007, 383–391
Phytochemical and biological studies on Saudi
Commiphora opobalsamum L.
FAWKEYA A. ABBASy, SHAZA M. AL-MASSARANYy, SHABANA KHANz,
TAWFEQ A. AL-HOWIRINYy, JABER S. MOSSAyand
EHAB A. ABOURASHED*y
yDepartment of Pharmacognosy, College of Pharmacy, King Saud University,
PO Box 2457, Riyadh 11451, Saudi Arabia
zNational Center for Natural Products Research, School of Pharmacy,
University of Mississippi, MS 38677, USA
(Received 28 April 2006; in final form 4 August 2006)
The aerial part of Commiphora opobalsamum L. (Burseraceae) growing in Saudi Arabia was
subjected to a phytopharmacological investigation in order to identify its major chemical
constituents and to evaluate its extracts and isolated compounds in preliminary in vitro assays
for antimicrobial, antimalarial, antitumor, anti-inflammatory (COX-2 inhibition), antioxidant
and estrogenic activity. Six compounds were isolated and identified as the triterpenes friedelin,
canophyllal, and oleanonic acid; the flavonols mearnsetin and quercetin; and syringic acid.
The ethyl acetate extract was moderately active against Staphylococcus aureus,Pseudomonas
aeruginosa, and Plasmodium falciparum; while the petroleum ether and chloroform extracts
inhibited COX-2 at 5 and 10 mgmL
1
, respectively. Of the isolated compounds, syringic acid
showed moderate antimalarial, anticandidal, and antimycobacterial activity; while mearnsetin
and quercetin exhibited antioxidant activity comparable to ascorbic acid and trolox. This is the
first detailed phytochemical investigation of C. opobalsamum L. growing in Saudi Arabia and
elsewhere. The isolated compounds are reported from this plant for the first time and their full
1
H and
13
C NMR assignments are included.
Keywords: Commiphora opobalsamum; Burseraceae; Triterpenes; Flavonols; Antimicrobial;
Antimalarial; Antioxidant; COX-2 inhibition
1. Introduction
The genus Commiphora (Burseraceae) comprises over 150 species, most of which
are confined to Eastern Africa, with a few species that occur in Arabia and India [1].
Commiphora opobalsamum L. is a species of the genus found in Saudi Arabia [1].
Commiphora opobalsamum is a strong smelling, green, non thorny tree or large shrub
[2]. It stands 10–12 feet high, with wand-like spreading branches [2]. The bark is of a
rich brown color; leaves are trifoliate, small and scanty; flowers are unisexual, small,
*Corresponding author. Tel.: þ966-1-467-7256. Fax: þ966-1-467-7245. Email: abourashed@yahoo.com
Natural Product Research
ISSN 1478-6419 print/ISSN 1029-2349 online ß2007 Taylor & Francis
http://www.tandf.co.uk/journals
DOI: 10.1080/14786410600942025
Downloaded By: [Abourashed, Ehab A.] At: 13:57 14 May 2007
and reddish in color. The fruits are the size of a small pea with an agreeable aromatic
taste while the seeds are solitary, yellow, and grooved along one side [3]. The liquid
exudate of the plant is turbid, thick, grey and odorous, and solidifies on exposure.
In traditional Arabian medicine, C. opobalsamum extract is used to treat headache,
urinary retention, and constipation [4]. The total extract of C. opobalsamum was
recently shown to possess hypotensive, antiulcerogenic, and hepatoprotective effects in
rats [5–7]. Preliminary phytochemical screening of the aerial parts of C. opobalsamum
revealed the presence of flavonoids, sterols, triterpenes, saponins, volatile bases, and
volatile oil [8].
The diverse biological activities reported for C. opobalsamum and related species, in
addition to the absence of detailed chemical reports on C. opobalsamum, justified the
investigation of its phytochemical composition and biological activities in an attempt to
correlate the results with traditional use of this plant. In this article, we describe the
isolation and characterization of six compounds for the first time from C. opobalsamum.
The identified compounds are friedelin (1), canophyllal (2), oleanonic acid (3), syringic
acid (4), mearnsetin (5), and quercetin (6) (figure 1). The biological activities of different
extracts and some of the isolated compounds were evaluated in a number of in vitro
assays for antimicrobial, antimalarial, antitumor, anti-inflammatory, antioxidant, and
estrogenic activities.
O
OH
OOH
HO
OR
OH
R
O
R
5 R = CH3, R = OH
6 R = H, R = H
1 R = CH3
2 R = CHO
O
COOH
3
2
3
4
5
79
1 3
4
3
1
5
6
9
10
12
14
17
18
20
22
23
24
25
26
27
28
2930
10
11
12
13
18
19
17
27
28
HO O
OCH3
OH
4
H3CO
Figure 1. Chemical structures of compounds 16.
384 F. A. Abbas et al.
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2. Results and discussion
Three triterpenes were isolated by column chromatography of the petroleum ether
extract and were identified by comprehensive analysis of their MS and NMR spectra in
comparison with published data. Compound 1was obtained from the fractions eluted
with 5% ethyl acetate in n-hexane as an amorphous residue which on repeated
crystallization from methanol, yielded fine needles showing positive Lieberman’s test.
MS analysis of 1showed a molecular ion at m/z 426 suggesting a molecular formula of
C
30
H
50
O. The
13
C NMR and DEPT spectra of 1confirmed the presence of 30 carbons:
eight methyls, eleven methylenes, four methines, and seven quaternary carbons, one of
which at 213.2. The
1
H NMR spectrum of 1displayed seven tertiary methyl groups at
0.75, 0.90, 0.98, 1.02, 1.03, 1.07, and 1.20. The eighth methyl group appeared as a
doublet at 0.92. HMBC showed a clear correlation between the proton at 0.92 and
the carbonyl carbon at 213.2. Further investigation of the COSY and HMBC data
suggested a friedelane-type triterpene structure. Comparing these data with the
literature [9] confirmed the structure of 1as friedo-D:A-oleanon-3-one (friedelin).
Compound 2was isolated as colorless needles by repeated crystallization of the
residue obtained from fractions eluted with 10% ethyl acetate in n-hexane. MS analysis
of 2showed a molecular ion at m/z 440 suggesting a molecular formula of C
30
H
48
O
2
.
The
13
C NMR spectrum of 2was very similar to that of 1, showing two carbonyl signals
at 210.0 and 214.0, together with those of seven methyls, eleven methylenes, four
methines, and six quaternary carbons. The appearance of a singlet at 9.41 in
1
H NMR
indicated the presence of a CHO (210.0) attached to a quaternary carbon.
1
H NMR
also showed the presence of six tertiary methyls at 0.59, 0.64, 0.77, 0.89, 0.91, and 1.00,
a secondary methyl at 0.80, in addition to a complex pattern around 1–2.4 due to
methylene and methine protons. These data suggested that 2had the same triterpene
skeleton of 1with the aldehydic group attached to either C-14 or C-17. Further analysis
of 1D and 2D-NMR spectra in comparison with those of 1suggested that the CHO
group was attached to C-17 as evidenced by: (i) the
13
C chemical shift deviation around
C-17 (C-16, C-18 & C-22) in 2compared to 1; and (ii) a 2-bond correlation
between H-28 (9.41) and C-17 (47.7). The structure of 2was thus assigned as
3-oxo-27-friedelanal, (canophyllal) [10,11].
Compound 3was isolated as colorless needles by repeated crystallization of the
residue obtained from fractions eluted with 20% ethyl acetate in n-hexane. MS analysis
of 3showed a molecular ion at m/z 454 suggesting a molecular formula of C
30
H
46
O
3
.
The
13
C NMR and DEPT spectra of 3confirmed the presence of 30 carbons: seven
methyls, eleven methylenes, four methines and eight quaternary carbons, one of which
was olefinic (143.6) and two were carbonyls (184.1 and 217.0). Further investigation
of the 1D and 2D-NMR spectra of 3indicated a 3-oxo triterpene skeleton with a
12,13
unsaturation and a free carboxylic acid group. Comparison of the NMR data with the
literature showed that 3was 3-oxo-olean-12-en-28-oic acid (oleanonic acid) [12].
Three phenolic compounds were obtained by column chromatography of the ethyl
acetate fraction. Compound 4eluted first to give a pale yellow powder on drying. Its
MS showed a molecular ion at m/z 198 corresponding to C
9
H
10
O
5
. The
13
C NMR of 4
showed two methoxyls, two olefinic methines and five quaternary carbons, including a
carboxy, and three oxygenated olefinic carbons. The only signals appearing in the
1
H NMR were a 6H singlet for the two methoxyls (3.90) and a 2H singlet for
two aromatic protons (7.35). Further analysis of the NMR data indicated
Phytochemical and biological studies on Saudi C. opobalsamum L. 385
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a symmetric trisubstituted phenolic acid. Two of the substituents were methoxyl
groups and the third a hydroxyl group. The data was found to fit well with that of
4-hydroxy-3,5-dimethoxybenzoic acid (syringic acid) [13,14]. Further evidence for the
structure of 4was provided by a 3-bond correlation between H-2/6 (7.35) and the
carboxy carbon (170.0). The possibility of 4-hydroxy-2,6-dimethoxybenzoic acid was
thus eliminated (table 1).
Compound 5was isolated as yellow needles whose MS had a molecular ion at
m/z 332 suggesting a pentahydroxymethoxy flavone with the formula C
16
H
12
O
8
. The
1
H NMR spectrum displayed two 1H doublets at 6.17 and 6.36 assigned to H-6 and
H-8, respectively. A 3H singlet at 3.87, and a 2H singlet at 7.30 were assigned to one
methoxy group at C-40and two equivalent aromatic protons at C-20/60, respectively;
typical for a symmetrically substituted myricetin-type B-ring. The position of the
methoxyl group was further supported by a 3-bond HMBC correlation between its
proton (3.87) and C-40(150.5). The UV spectrum of 5in MeOH also showed an
absorbance band at 360 nm indicating a 3-hydroxyflavone. The above data were in
accord with a 3,5,7,30,40,50oxygenation pattern with a methoxyl group at C-40and
identical to those reported for myricetin 40-methylether (mearnsetin) [15,16].
Compound 6was isolated as yellow crystals with a molecular weight of 302
corresponding to C
15
H
10
O
7
and suggesting a pentahydroxyflavone. The NMR
spectrum exhibited the aromatic signals at 7.73, 6.87 and 7.62 attributable to H-20,
H-50and H-60, respectively. Two m-coupled doublets at 6.17 and 6.37 were assigned to
H-6 and H-8, respectively. The UV spectrum of 6in MeOH also showed absorption
maxima at 259 nm (band II) and 368 nm (band I) indicating a 3-hydroxyflavone.
These data, along with literature comparison, confirmed the structure of 6as
30,40,5,7-tetrahydroxyflavonol (quercetin) [17,18].
The fractions obtained by successive solvent extraction of the dry plant material
were subjected to a panel of in vitro bioassays for antibacterial, antifungal, antimalarial,
Table 1.
1
H and
13
C NMR assignments of the phenolic acid and flavonoid compounds 4,5and 6
in CD
3
OD.
45 6
C
C
H
(m, JHz)
C
H
(m, JHz)
C
H
(m, JHz)
1 121.9 –––– –
2 108.4 7.35 (s) 145.8 147.6
3 148.9 – 137.3 – 136.0
4 141.8 – 176.3 – 176.1
5 148.9 – 161.3 – 161.3
6 108.4 7.35 (s) 98.2 6.17 (d, 2.5) 98.1 6.17 (d, 2.5)
7 164.7 – 164.4
8 93.3 6.36 (d, 2.5) 93.2 6.37 (d, 2.5)
9 157.1 – 157.1
10 103.4 – 103.3
10126.8 – 123.0
20107.5 7.30 (s) 114.8 7.73 (d, 2.5)
30150.5 – 147.6
40137.3 – 145.0
50150.5 115.1 6.88 (d, 9)
60107.5 7.30 (s) 120.5 7.62 (dd, 9, 2.5)
OCH
3
56.8 3.90 (s) 59.7 3.87 (s)
COOH 170.0 –––– –
386 F. A. Abbas et al.
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anticancer, anti-inflammatory, and estrogenic activity. While petroleum ether and
aqueous fractions showed moderate antimalarial activity, the ethyl acetate fraction
exhibited promising antimalarial activity against chloroquin-sensitive (D6) and
chloroquin-resistant (W2) strains of Plasmodium. falciparum with IC
50
of 0.75 and
2.2 mgmL
1
, respectively (table 2). The same fraction also exhibited antibacterial
activity against Startylococus. aureus, MRSA and Pseudomonas aeruginosa with IC
50
of
75, 95, and 150 mgmL
1
, respectively. The chloroform (fraction 1) and petroleum ether
(fraction 2a) fractions inhibited COX-2 enzyme activity at IC
50
of 10 and 5 mgmL
1
,
respectively. Of the isolated compounds, only 4exhibited weak antimicrobial activity
against Candida glabrata and Mycobacterium intracellulare with IC
50
values of 10 and
15 mgmL
1
, respectively, in comparison to amphotericin B at 0.15 mgmL
1
, for C.
glabrata and ciprofloxacin at 0.3 mgmL
1
, for M. intracellulare. Compound 4also
exhibited weak antimalarial activity in comparison to chloroquin and artemisinin
against the tested strains as shown in table 2. On the other hand, triterpene (1) and the
two flavonols (5) and (6) showed antioxidant activitities without exhibiting any
cytotoxic effects on HL-60 cells. The activity of 5and 6was comparable to the positive
controls ascorbic acid and trolox. Results are shown in table 3.
This is the first in-depth phytochemical study to be conducted on C. opobalsamum L.
and the isolated compounds are reported in this species for the first time. The COX-2
inhibition of the petroleum ether and chloroform fractions supports the traditional use
of this species for treating headaches. Although none of the triterpenes exhibited any
biological activity in the screening assays, except the antioxidant activity of 1, the
petroleum ether and chloroform fractions displayed promising COX-2 inhibitory effect
which may be due to minor constituents present in these fractions. Further investigation
of these fractions and others is thus warranted.
Table 2. Antimalarial activity of C. opobalsamum fractions and compound 4against chloroquin-sensitive
(D6) and chloroquin-resistant (W2) strains of P. falciparum.
D6 W2
Fraction IC
50a
SI
b
IC
50
SI
Petroleum ether 11.0 49.1 6.9 414.5
Ethylacetate 0.75 4133 2.2 445.5
Aqueous 9.6 410.4 12 48.3
Syringic acid (4) 3.5 42.86 3.2 43.12
Chloroquin 10.75 ng mL
1
–90ngmL
1
Artemisinin 9.0 ng mL
1
10.5 ng mL
1
a
IC
50
values are in mgmL
1
for samples.
b
SI, selectivity index ¼IC
50
for vero cells/IC
50
for Plasmodium (samples were not cytotoxic to vero cells at 100 mgmL
1
for
fractions and 10 mgmL
1
for syringic acid).
Table 3. Antioxidant effect of compounds 1,5and 6in HL-60 cells.
Compound IC
50
(mgmL
1
) Cytotoxicity to HL-60 IC
50
(mgmL
1
)
Friedelin (1) 5.00 431.25
Mearnsetin (5) 0.70 462.50
Quercetin (6) 0.55 462.50
Ascorbic acid 0.39 NC
Trolox 0.67 NC
Phytochemical and biological studies on Saudi C. opobalsamum L. 387
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3. Experimental
3.1. General procedures
Melting points were recorded on Mettler FP800 and are uncorrected. IR spectra were
obtained in KBr discs using Perkin-Elmer FTIR 1600 spectrophotometer. UV spectra
were recorded in MeOH on Unicam UV-vis spectrophotometer. Mass spectra were
obtained on a Shimadzu QP-5000.
1
H and
13
C NMR spectra were recorded on a
Bruker Avance 500 running at 500 and 125 MHz, respectively. Chemical shifts are
reported in units relative to TMS. All column chromatographic separations were
performed on silica gel 60 (230–400 mesh), while thin layer chromatography (TLC)
was performed on silica gel-coated aluminum plates (Merck kieselgel 60 F254). All
solvents used for extraction and chromatography were of general-purpose and
analytical grades, respectively.
3.2. Plant material
The aerial parts of C. opobalsamum L. were collected in 2003 near the city of
Abha, Southern Saudi Arabia. The plant was identified by Dr Ateeq-ur-Rahman of
the Research Center for Medicinal, Aromatic and Poisonous Plants, College of
Pharmacy, King Saud University and a voucher specimen was deposited in its
herbarium.
3.3. Extraction and isolation
Powdered plant material (500 g) was defatted with petroleum ether (60–80C, 5 L).
The petroleum ether extract was filtered and evaporated to dryness (fraction 1,
20 g). The defatted powder was air-dried and macerated at room temperature with
95% ethanol (5 1.5 L) and the ethanolic extract was evaporated to dryness at
40Cin vacuo (fraction 2, 18 g). Fraction 2 was suspended in water (0.5 L) and
extracted successively with chloroform (3 200 mL), then with ethyl acetate
(3 200 mL). The combined chloroformic fractions were evaporated in vacuo to
yield 3.5 g of a brownish residue (fraction 2a). The same was done with the ethyl
acetate fractions to yield 3.8 g of residue (fraction 2b). The remaining aqueous
solution was freeze dried to yield 9.1 g of fraction 3. Fraction 1 was subjected to
CC (600 g silica gel 60, 100 4 cm) using increasing polarity of n-hexane ethyl
acetate. The collected fractions (500 mL each) were monitored by TLC and similar
ones were combined together. Fractions eluted with 5% ethyl acetate (1.4 g) in
hexane afforded 1(16 mg) after crystallization from MeOH. Compounds 2(46 mg)
and 3(62 mg) were obtained by direct crystallization from the 10 and 20% ethyl
acetate fractions, respectively. Fraction 2b (3 g) was applied to a silica gel column
(150 g, 60 4 cm) and eluted with increasing polarity of ethyl acetate in chloroform.
Fractions 13–16 (CHCl
3
) afforded 47 mg of 4after crystallization from MeOH;
while fractions 30–34 and 45–52 (CHCl
3
) afforded 5(30 mg) and 6(32 mg),
respectively, after crystallization from MeOH.
388 F. A. Abbas et al.
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Friedelin (D:A-friedo-oleanan-3-one) (1). Fine white needles (16 mg); m.p. 262C; TLC
R
f
0.80 (CHCl
3
–MeOH–acetic acid, 50 : 1 : one drop);
1
H and
13
C NMR data (table 4);
LRMS m/z 426 [M
þ
].
Canophyllal (27-ol-D:A-friedo-oleanan-3-one) (2). Colorless needles (46 mg); m.p.
252–253C; TLC R
f
0.60 (CHCl
3
–MeOH–acetic acid, 50 : 1 : one drop);
1
H and
13
C
NMR data (table 4); LRMS m/z 440 [M
þ
].
Oleanonic acid (3-oxo-olean-12-en-28-oic acid) (3). Needles (62 mg); m.p. 160C; TLC R
f
0.51 (hexane–EtOAc, 2 : 1);
1
H and
13
C NMR data (table 4); LRMS m/z 454 [M
þ
].
Syringic acid (4-hydroxy-3,5-dimethoxybenzoic acid) (4). Pale yellow crystals (47 mg);
m.p. 210C; TLC R
f
0.60 (CHCl
3
–MeOH, 9 : 1);
1
H and
13
C NMR data (table 4);
LRMS m/z 198 [M
þ
].
Mearnsetin (3,5,7,30,50-pentahydroxy-40-methoxyflavone) (5). Yellow needles (30 mg);
m.p. 208–210C; TLC R
f
0.46 (CHCl
3
–MeOH, 9 : 1);
1
H and
13
C NMR data (table 4);
LRMS m/z 332 [M
þ
].
Quercetin (3,5,7,30-tetrahydroxyflavone) (6). Yellow crystals (32 mg); m.p. 258C; TLC R
f
0.40 (CHCl
3
–MeOH, 9 : 1);
1
H and
13
C NMR data (table 4); LRMS m/z 302 [M
þ
].
Table 4.
1
H and
13
C NMR assignments of the triterpenes 1,2and 3in CDCl
3
.
123
C
C
H
(m, JHz)
C
H
(m, JHz)
C
H
(m, JHz)
1 22.3 1.71 (m), 1.97 (m) 22.3 1.60 (m), 1.89 (m) 39.3 1.43 (m), 1.91 (m)
2 41.5 2.31 (m), 2.41 (dd, 3.5, 13) 41.5 2.22 (m), 2.32 (m) 34.2 2.38 (m), 2.56 (m)
3 213.2 – 214.0 – 217.0 –
4 58.2 2.28 (m) 58.2 2.16 (q, 6.7) 47.4 –
5 42.2 – 42.0 – 55.3 1.35 (m)
6 41.3 1.31 (m), 1.78 (m) 41.0 1.20 (m), 1.67 (m) 19.5 1.50 (m)
7 18.2 1.41 (m), 1.51 (m) 18.1 1.3 (m) 32.1 1.37 (m), 1.49 (m)
8 53.1 1.41 (m) 52.8 1.31 (m) 39.1 –
9 37.4 – 37.1 – 46.9 1.65 (m)
10 59.5 1.55 (m) 59.2 1.45 (m) 36.8 –
11 35.6 1.4 (m) 35.4 1.42 (m) 23.5 1.93 (m), 2.00 (m)
12 30.5 1.28 (m), 1.3 (m) 30.6 1.18 (m) 122.4 5.32 (brs)
13 39.7 – 38.7 – 143.6 –
14 38.3 – 37.7 – 41.7 –
15 32.4 1.3 (m), 1.5 (m) 32.4 1.18 (m) 27.7 1.14 (m), 1.77 (m)
16 36.0 1.4-1.6 (m) 34.9 1.2 (m) 22.9 1.66 (m), 1.99 (m)
17 30.0 – 47.7 – 46.6 –
18 42.8 1.4 (m), 1.6 (m) 36.4 2.12 (m) 41.0 2.85 (dd, 13, 3)
19 35.3 1.6 (m) 35.4 1.42 (m) 45.8 1.16 (m), 1.64 (m)
20 28.2 – 28.3 – 30.7 –
21 32.8 1.31 (m), 1.51 (m) 32.4 1.18 (m) 33.8 1.24 (m), 1.36 (m)
22 39.3 0.97 (m), 1.51 (m) 28.0 1.56 (m), 2.00 (m) 32.4 1.6 (m), 1.80 (m)
23 6.8 0.92 (d, 7.0) 6.9 0.80 (d, 6.5) 21.4 1.05 (s)
24 14.7 0.75 (s) 14.6 0.64 (s) 26.4 1.10 (s)
25 18.0 0.90 (s) 17.2 0.77 (s) 15.0 1.07 (s)
26 20.3 1.03 (s) 20.0 0.59 (s) 17.0 0.83 (s)
27 18.7 1.07 (s) 18.8 1.00 (s) 25.8 1.16 (s)
28 32.1 1.20 (s) 210.0 9.41 (s) 184.1 –
29 35.0 0.98 (s) 34.5 0.89 (s) 33.1 0.93 (s)
30 31.8 1.02 (s) 29.4 0.91 (s) 23.6 0.95 (s)
Phytochemical and biological studies on Saudi C. opobalsamum L. 389
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3.4. Biological evaluation
3.4.1. Antimicrobial assays. These were conducted as described earlier [19] against
S. aureus (normal & methicillin-resistant), P. aeruginosa,M. intracellulare,Candida
albicans,C. glabrata and Candida krusei,Cryptococcus neoformans, and Aspergillus
fumigatus. Amphotericin B and ciprofloxacin were used as controls drugs.
3.4.2. Antimalarial assay. It was conducted as described earlier [19] against two
strains of P. falciparum (D6 strain: chloroquine-sensitive & W2 strain: chloroquine-
resistant). Chloroquin and artemisinin were used as control drugs.
3.4.3. Assay for cytotoxicity. Cytotoxicity to mammalian kidney fibroblasts (vero
cells) and antitumor activity against four human tumor cell lines: malignant melanoma
(SK-MEL), oral epidermal carcinoma (KB), breast ductal carcinoma (BT549) and
ovary carcinoma (SK-OV3) was determined as described earlier [20].
3.4.4. Assay for antioxidant activity. Antioxidant activity was determined by the
DCFH-DA (20,70-dichlorofluorescin diacetate) method in Myelomonocytic HL-60 cells
as described earlier [21]. Briefly, for the assay, cells were plated at a density of 1.25 10
5
cells per well in 96-well plates. After treatment with different concentrations of
the test samples for 30 min, cells were stimulated with 100 ng mL
1
phorbol
12-myristate-13-acetate (PMA, Sigma) for 30 min. DCFH-DA (molecular probes,
5mgmL
1
) was added and further incubated for 15 min. Plates were read on a PolarStar
at an excitation wavelength of 485 nm and emission at 530 nm to measure level of DCF
production.
3.4.5. Assay for estrogenic activity. This was conducted in recombinant yeast
expressing human estrogen receptor according to the method of Routledge and
Sumpter [22,23].
3.4.6. Assay for inhibition of COX-2 activity. Mouse macrophages (RAW 264.7,
ATCC, USA) were cultured in 75 cm
2
culture flask in RPMI-1640 medium (Gibco
TM
,
Invitrogen Corp. USA) supplemented with 10% bovine calf serum (Hyclone) and
60 mg L
1
amikacin (Sigma), at 37C in an atmosphere of 95% humidity and 5% CO
2
.
For the assay, cells were seeded in the wells of 96-well plates (50,000 cells per well) and
incubated at 37C for 24 h. Confluent cells were treated with 250 mM aspirin for 30 min
to completely inactivate COX-1 activity. After washing thoroughly with medium,
they were incubated with 5 mgmL
1
LPS (Sigma) for 16 h to induce the production of
COX-2. Induced cells were washed with medium to remove LPS completely and treated
with different concentrations of test samples (extracts or pure compounds) for 2 h.
Arachidonic acid (300 mM, Sigma) was added and the cells were further incubated for
30 min. The amount of PGE
2
released in the medium was determined using PGE
2
Enzyme Immunoassay kit (Cayman Chem. Co., USA). COX-2 activity was determined
by the conversion of exogenous arachidonic acid to PGE
2
and is expressed as % of the
vehicle control (DMSO, 0.5%). IC
50
values were calculated from the dose curves
390 F. A. Abbas et al.
Downloaded By: [Abourashed, Ehab A.] At: 13:57 14 May 2007
generated by plotting % inhibition of COX-2 against the test concentrations. NS-398
(Cayman Chem. Co.), a specific inhibitor of COX-2, was included as positive control in
each assay.
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Phytochemical and biological studies on Saudi C. opobalsamum L. 391
... Commiphora species are characterised as small trees or shrubs with spine scent branches, pale-grey bark, and reddish-brown resinous exudates. Terpenoids (Abbas et al. 2007, Shen et al. 2012a, flavonoids (Abbas et al. 2007) and lignans (Francis et al. 2004) are the major constituents of the plant. Additionally, the polypodane triterpenoids and steroids present in the resin were used as chemotaxonomic markers to identify plants belong to the Commiphora genus (Shen et al. 2012b). ...
... Commiphora species are characterised as small trees or shrubs with spine scent branches, pale-grey bark, and reddish-brown resinous exudates. Terpenoids (Abbas et al. 2007, Shen et al. 2012a, flavonoids (Abbas et al. 2007) and lignans (Francis et al. 2004) are the major constituents of the plant. Additionally, the polypodane triterpenoids and steroids present in the resin were used as chemotaxonomic markers to identify plants belong to the Commiphora genus (Shen et al. 2012b). ...
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Context: Hyperglycaemia plays an important role in the development of non-alcoholic fatty liver disease, which is a common complication in diabetics. Objective: The present study aimed to investigate the chemical composition and the efficacy of Commiphora opobalsamum stem bark butanol fraction in ameliorating liver injury associated with diabetes induced by streptozotocin (STZ) in rats. Materials and methods: The butanol fraction was applied to high-performance liquid chromatography-mass spectrometry (HPLC/MSn) to identify the most bioactive metabolites. Diabetes was induced by a single intraperitoneal injection of STZ (60 mg/kg body weight), while treatment with the plant extract was performed (100 mg/kg body weight) for three weeks after diabetic induction for one month. Results: Thirty eight metabolites were tentatively identified from the butanol fraction of C. opobalsamum stem bark. Insulin, glutathione, superoxide dismutase, and high density lipoprotein levels in diabetic rats were significantly low (p < 0.05), while glucose, α-amylase, malondialdehyde, aspartate and alanine aminotransferases, cholesterol, triglycerides, low density lipoprotein, tumour necrosis factor-α, interleukin-6, and DNA fragmentation levels were significantly high. Treatment with the plant extract showed improvements in the seleced parameters by variable degrees. Conclusion: The plant extract is considered as a promising natural therapeutic agent against liver injury, hyperglycemia, oxidative stress, inflammation, hyperlipidaemia, and DNA damage.
... UPLC-MS of Xihuang Pills, an anti-cancer TCM made of Commiphora myrrha Engl, Moschus, Boswellia carteri Birdwood and Bos taurus domesticus Gmelin [5], was conducted. The extract of Saudi Commiphora opobalsamum L has been shown to contain quercetin by MS and NMR spectra analysis [53]. The presence of polyphenols with possible anticancer effects in Commiphora leptophloeos extracts, such as rutin, vitexin, and quercetin diglycosides, was demonstrated by thin layer chromatography (TLC) and other analyses [54]. ...
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