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Vol. 8(2), pp. 25-48, February 2016
DOI: 10.5897/JPP2015.0367
Article Number: D4478E557364
ISSN 2141-2502
Copyright © 2016
Author(s) retain the copyright of this article
http://www.academicjournals.org/JPP
Journal of Pharmacognosy and
Phytotherapy
Full Length Research Paper
Determination of metabolites products by Cassia
angustifolia and evaluate antimicobial activity
Ali Hussein Al-Marzoqi 1, Mohammed Yahya Hadi2 and Imad Hadi Hameed1*
1Department of Biology, Babylon University, Hilla City, Iraq.
2College of Biotechnology, Al-Qasim Green University, Iraq.
Received 26 August 2015; Accepted 20 October 2015
Phytochemicals are chemical compounds often referred to as secondary metabolites. Forty four
bioactive phytochemical compounds were identified in the methanolic leaves extract of Cassia
angustifolia. The identification of phytochemical compounds is based on the peak area, retention time
molecular weight and molecular formula. Gas chromatography-mass spectrometry (GC-MS) analysis of
C. angustifolia revealed the existence of the 2,5-dimethyl-4-hydroxy-3(2H)-furanon, 2-propyl-
tetrahydropyran-3-ol, estragole, benzene, 1-ethynyl-4-fluoro-, 5-hydroxymethylfurfural, anethole, 7-
oxabicyclo[4.1.0]heptan-2-one,6-methyl-3-(1-methylethyl)-, 2-methoxy-4-vinylphenol, 1,2,2-
trimethylcyclopentane-1,3-dicarboxylic acid, E-9-tetradecenoic acid, caryophyllene, cholestan-3-ol,2-
methylene-, (3ß,5α)-, Benzene, 1-(1,5-dimethyl-4-hexenyl)-4-methyl-, ß-curcumene, 7-epi-cis-
sesquisabinene hydrate, Cyclohexene, 3-(1,5-dimethyl-4-hexenyl)-6-methylene-,[S-(R*,S*)]-m,
octahydrobenzo[b]pyran, 4a-acetoxy-5,5,8a,-trimethyl, dodecanoic acid, 3-hydroxy, tetraacetyl-d-xylonic
nitrile, 1-ethenyl 3, trans(1,1-dimethylethyl)-4,cis-methoxycyclohexan-1-ol, phen-1,4-diol,2,3-dimethyl-5-
trifluoromethyl, 5-benzofuranacetic acid, 6-ethenyl-2,4,5,6,7,7a-hexahydro-3,6-dime, 5-benzofuranacetic
acid, 6-ethenyl-2,4,5,6,7,7a-hexahydro-3,6-dime, phytol, acetate, desulphosiniqrin, oxiraneundecanoic
acid, 3-pentyl-,methyl ester, cis,Phytol, 9,12,15-Octadecatrienoic acid, 2-phenyl-1,3-dioxan-5-yl ester,
butanoic acid, 1a,2,5,5a,6,9,10,10a-octahydro-5,5adihydroxy-4-(h), 9-Octadecenoic acid, 1,2,3-
propanetriyl ester, (E,E,E) and Diisooctyl phthalate. C. angustifolia was highly active against
Aspergillus terreus (6.01±0.27).
Key words: Antifungal, gas chromatography-mass spectrometry, fourier-transform infrared spectroscopy,
phytochemicals, Cassia angustifolia.
INTRODUCTION
Medicinal plants are those plants which contain
substances that can be used for the therapeutic purposes
in one or more of its organ or substances which are
precursors for the synthesis of useful drugs (Sofowora,
1982; Bako et al., 2005; Altameme et al., 2015a). The
use of medicinal herbs to relieve and treat diseases is
*Corresponding author. E-mail: imad_dna@yahoo.com. Tel: 009647716150716.
Author(s) agree that this article remain permanently open access under the terms of the Creative Commons Attribution
License 4.0 International License
26 J. Pharmacognosy Phytother.
increasing because of their mild features and few side
effects (Basgel and Erdemoglu, 2006). These plants are
unlicensed and freely available, however, and there is no
requirement to demonstrate efficacy, safety or quality
(Ernst, 1998). The genus Cassia comprises 580 species
of shrubs and trees which are widely distributed
throughout the world, of which only twenty species are
indigenous to India which belongs to the family
Caesalpiniaceae, which generally consist of trees, shrubs
and a few woody herbs. Cassia angustifolia Vahl (Family:
Caesalpinaceae), popularly known as senna, is a
valuable plant drug in Ayurvedic and modern system of
medicine for the treatment of constipation. The pods and
leaves of senna, as well as the pharmaceutical
preparations containing sennosides A and B, are widely
used in medicine because of their laxative properties.
Senna is used in medicine as a cathartic; it is especially
useful in habitual constipation. The laxative property of
senna is based on two glycosides viz. sennoside A and
sennoside B, whereas sennoside C and D have also
been reported in the plant. Apart from sennoside, the pod
and leaf also contain glycosides of anthraquinones rhein
and chrysophenic acid, recently two naphthalene
glycosides have also been isolated from leaves and pods
(Gupta, 2010).
Antimicrobial activity has been reported in many plants
by various workers (Sarin, 2005; Bansal et al., 2010;
Chahal et al., 2010; Seth and Sarin, 2010; Malwal and
Sarin, 2011; Hameed et al., 2015a). A new
anthraquinone glycoside (emodin 8-0- sophorside) and
seven known glycosides were isolated from the leaves of
C. angustifolia and their structures were elucidated by
spectral analysis (Kinjo et al., 1994). It has anti-
inflammatory properties (Vanderperren et al., 2005),
detoxification ability (Bournemouth, 1992) and also helps
improve the function of the digestive system (Hoffmann,
1990). Cassia senna helps to reduce the nervous tension
(Mills, 1993) and also helps in aiding the spleen and liver
in production of blood and red blood cells (Spiller et al.,
2003; Altameme et al., 2015b; Hamza et al., 2015). The
present study was undertaken to investigate the
antimicrobial activity and phytochemical analysis of C.
angustifolia.
MATERIALS AND METHODS
Collection and preparation of plant material
C. angustifolia was purchased from local market in Hilla city, middle
of Iraq. After thorough cleaning and removal of foreign materials,
the seeds were stored in airtight container to avoid the effect of
humidity and then stored at room temperature until further use
(Hameed et al., 2015b; Jasim et al., 2015).
Preparation of sample
About fifteen grams of methanolic leaves extract of C. angustifolia
powdered was soaked in 30 ml methanol for ten hours in a
rotatory shaker. Whatman No.1 filter paper was used to separate
the extract of plant. The filtrates were used for further
phytochemical analysis. It was again filtered through sodium
sulphate in order to remove the traces of moisture (Hussein et al.,
2015; Hameed et al., 2015c).
Gas chromatography – mass spectrum analysis
The GC-MS analysis of the plant extract was made in a Agilent
7890 A instrument under computer control at 70 eV. About 1 μl of
the methanol extract was injected into the GC-MS using a micro
syringe and the scanning was done for 45 min. As the compounds
were separated, they eluted from the column and entered a
detector which was capable of creating an electronic signal
whenever a compound was detected (Imad et al., 2014a; Kareem
et al., 2015). The greater the concentration in the sample, the
bigger was the signal obtained which was then processed by a
computer. The time from when the injection was made (Initial time)
to when elution occurred is referred to as the retention time (RT).
While the instrument was run, the computer generated a graph from
the signal called chromatogram. Each of the peaks in the
chromatogram represented the signal created when a compound
eluted from the gas chromatography column into the detector
(Mohammed and Imad, 2013; Imad et al., 2014b). The X-axis
showed the RT and the Y-axis measured the intensity of the signal
to quantify the component in the sample injected. As individual
compounds eluted from the gas chromatographic column, they
entered the electron ionization (mass spectroscopy) detector,
where they were bombarded with a stream of electrons causing,
them to break apart into fragments. The fragments obtained were
actually charged ions with a certain mass (Hameed et al., 2015d).
The mass/charge (M/Z) ratio obtained was calibrated from the
graph obtained, which was called the mass spectrum graph which
is the fingerprint of a molecule. Before analyzing the extract using
gas chromatography and mass spectroscopy, the temperature of
the oven, the flow rate of the gas used and the electron gun were
programmed initially. The temperature of the oven was maintained
at 100°C. Helium gas was used as a carrier as well as an eluent.
The flow rate of helium was set to 1 ml per minute. The electron
gun of mass detector liberated electrons having energy of about
70eV. The column employed here for the separation of components
was Elite 1 (100% dimethyl poly siloxane). The identity of the
components in the extracts was assigned by the comparison of
their retention indices and mass spectra fragmentation patterns with
those stored on the computer library and also with published
literatures (Imad et al., 2014c). Compounds were identified by
comparing their spectra to those of the Wiley and NIST/EPA/NIH
mass spectral libraries.
Determination of antifungal activity
Five-millimeter diameter wells were cut from the agar using a sterile
cork-borer, and 50 μl of the samples solutions (C. angustifolia) was
delivered into the wells. Antimicrobial activity was evaluated by
measuring the zone of inhibition against the test microorganisms.
Methanol was used as solvent control. Amphotericin B and
fluconazole were used as reference antifungal agent (Hameed et
al., 2015b). The tests were carried out in triplicate. The antifungal
activity was evaluated by measuring the inhibition-zone diameter
observed after 48 h of incubation.
Statistical analysis
Data were analyzed using analysis of variance (ANOVA), and
differences among the means were determined for significance at P
Al-Marzoqi et al. 27
Figure 1. GC-MS chromatogram of methanolic extract of Cassia angustifolia.
< 0.05, using Duncan’s multiple range test (by SPSS software)
Version 9.1.
RESULTS AND DISCUSSION
Gas chromatography and mass spectroscopy analysis of
compounds was carried out in methanolic extract of C.
angustifolia, as shown in Table 1. The GC-MS
chromatogram of the forty four peaks of the compounds
detected was shown in Figure 1. Chromatogram GC-MS
analysis of the methanol extract of Althaea rosea showed
the presence of 44 major peaks and the components
corresponding to the peaks were determined as follows.
The first set up peaks were determined to be 2,5-
dimethyl-4-hydroxy-3(2H)-furanon (Figure 2). The next
peaks considered to be 2-Propyl-tetrahydropyran-3-ol,
Estragole, Benzene, 1-ethynyl-4-fluoro-, 5-
Hydroxymethylfurfural, Anethole, 7-
Oxabicyclo[4.1.0]heptan-2-one,6-methyl-3-(1-
methylethyl)-, 2-Methoxy-4-vinylphenol, 1,2,2-
Trimethylcyclopentane-1,3-dicarboxylic acid, E-9-
Tetradecenoic acid, Caryophyllene, Cholestan-3-ol,2-
methylene-,(3ß,5α)-, Benzene, 1-(1,5-dimethyl-4-
hexenyl)-4-methyl-, ß-curcumene, 7-epi-cis-
sesquisabinene hydrate, Cyclohexene, 3-(1,5-dimethyl-4-
hexenyl)-6-methylene-,[S-(R*,S*)]-m, Octahydrobenzo[b]
pyran,4a-acetoxy-5,5,8a,-trimethyl, Dodecanoic acid, 3-
hydroxy, Tetraacetyl-d-xylonic nitrile, 1-Ethenyl
3,trans(1,1-dimethylethyl)-4,cis-methoxycyclohexan-1-ol,
Phen-1,4-diol,2,3-dimethyl-5-trifluoromethyl, 5-
Benzofuranacetic acid, 6-ethenyl-2,4,5,6,7,7a-hexahydro-
3,6-dime, 5-Benzofuranacetic acid, 6-ethenyl-
2,4,5,6,7,7a-hexahydro-3,6-dime, Phytol, acetate,
Desulphosiniqrin, Oxiraneundecanoic acid, 3-pentyl-
,methyl ester,cis, Phytol, 9,12,15-Octadecatrienoic acid,
2-phenyl-1,3-dioxan-5-yl ester, Butanoic acid,
1a,2,5,5a,6,9,10,10a-octahydro-5,5adihydroxy-4-(h), 9-
Octadecenoic acid, 1,2,3-propanetriyl ester, (E,E,E) and
Diisooctyl phthalate (Figures 3 to 45). Methanolic
extraction of plant showed notable antifungal activities
against Aspergillus niger, Aspergillus terreus, Aspergillus
flavus, and Aspergillus fumigatus (Table 2). C.
angustifolia was very highly active against A. terreus
(6.01±0.27). Aspergillus was found to be sensitive to all
test medicinal plants and mostly comparable to the
standard reference antifungal drug amphotericin B and
fluconazole to some extent.
28 J. Pharmacognosy Phytother.
Table 1. Major phytochemical compounds identified in Cassia angustifolia.
Pharmacological actions
MS Fragment- ions
Chemical structure
Exact mass
Molecular
weight
Formula
RT (min)
Phytochemical compound
Serial
No.
Antimicrobial effect
57, 72, 85, 94, 109, 128
128.047344
128
C6H8O3
4.883
2,5-dimethyl-4-hydroxy-3(2H)-
furanone
1
Anti-infective agent in human
microbial infections.
55, 73, 87, 101, 116, 144
144.115029
144
C8H16O2
5.908
2-Propyl-tetrahydropyran-3-ol
2
Anti-inflammatory activity
51, 55, 63, 77, 91, 105, 121, 133,
148
148.088815
148
C10H12O
6.303
Estragole,
3
Antibacterial activity / Antifungal
activity
50, 63, 74, 81, 94, 100, 120
120.0375285
120
C8H5F
6.720
Benzene , 1-ethynyl-4- fluoro
4
Al-Marzoqi et al. 29
Table 1. Cont'd
Antioxidant and specific anti-cancer
agents
53, 69, 81, 84, 97, 109, 126
126.0311694
126
C6H6O3
7.247
5-Hydroxymethylfurfural
5
Antihyperglycemic effect
51, 55, 63, 74, 77, 91, 105, 117,
133, 148
148.088815
148
C10H12O
7.510
Anethole
6
New chemical compound
55, 69, 83, 97, 111, 126, 139,
150, 168
168.115029
168
C10H16O2
7.750
7-Oxabicyclo[4.1.0]heptan-2-
one,6-methyl -3-(1-
methylethyl)-
7
Antioxidant, anti microbial and anti
inflammatory
51, 77, 89, 107, 121, 135
150.06808
150
C9H10O2
7.933
2-Methoxy-4-vinylphenol
8
30 J. Pharmacognosy Phytother.
Table 1. Cont'd
Anti- fungal
55, 68, 82, 109, 136, 154, 182
200.104859
200
C10H16O4
8.431
1,2,2-Trimethylcyclopentane-
1,3-dicarboxylic acid
9
Analgesic and anti-inflammatory
effect
55, 69, 83, 97, 110, 166, 208
226.19328
226
C14H26O2
8.746
E-9-Tetradecenoic acid
10
Anti-inflammatory, antibiotic,
antioxidant, anticarcinogenic and
local anaesthetic
79, 93, 105, 120, 133, 147, 161,
175, 189, 204
204.1878
204
C15H24
9.301
Caryophyllene
11
Anti-oxidant
69, 81, 95, 175, 227, 260, 315,
400
400.370516
400
C28H48O
9.616
Cholestan-3-ol,2-methylene-
,(3ß,5α)-
12
Antimicrobial and anti-inflammatory
55, 65, 69, 77, 83, 91, 95, 105,
119, 132, 145, 159, 187, 202
202.172151
202
C15H22
10.010
Benzene , 1-(1,5-dimethyl-4-
hexenyl)-4-methyl-
13
Al-Marzoqi et al. 31
Table 1. Cont'd
Anti-tumor, anti-cancer, anti-
repellent, antitussive and anti-
platelet
55, 69, 77, 93, 105, 119, 133,
147, 161, 176, 189, 204
204.1878
204
C15H24
10.165
ß-curcumene
14
nti-cancer
55, 69, 82, 93, 105, 119, 161,
175, 204, 222
222.198365
222
C15H26O
10.274
7-epi-cis-sesquisabinene
hydrate
15
Anti-bacterial and antifungal
55, 69, 77, 93, 109, 133, 147,
161, 175, 189, 204
204.1878
204
C15H24
10.508
Cyclohexene ,3-(1,5-dimethyl-
4-hexenyl)-6-methylene-,[S-
(R*,S*)]-
16
Anti-Candida and anti-inflammatory
55, 69, 97, 111, 124, 137, 151,
165, 180, 197, 240
240.1725445
240
C14H24O3
10.771
Octahydrobenzo[b]pyran,4a-
acetoxy-5,5,8a,-trimethyl
17
Antifungal activity
55, 69, 83, 96, 112, 126, 138,
151, 180, 200, 215
216.1725445
216
C12H24O3
11.218
Dodecanoic acid , 3-hydroxy
18
32 J. Pharmacognosy Phytother.
Table 1. Cont'd
Have anti-viral effects
60, 73, 112, 133, 164, 197, 226,
270
343.090332
343
C14H17NO9
11.012
Tetraacetyl-d-xylonic nitrile
19
Unknown
57, 70, 79, 91, 104, 121, 137,
151, 163, 192, 210
210.16198
210
C13H22O2
11.246
1-Ethenyl 3,trans(1,1-
dimethylethyl)-4,cis-
methoxycyclohexan-1-ol
20
Antimicrobial effect
57, 69, 83, 91, 123, 149, 206
206.055464
206
C9H9F3O2
11.378
Phen-1,4-diol,2,3-dimethyl-5-
trifluoromethyl
21
New chemical compound
53, 77, 91, 105, 121, 148, 176,
216, 244, 276
276.13616
276
C16H20O4
12.036
5-Benzofuranacetic acid,6-
ethenyl -2,4,5,6,7,7a-
hexahydro-3,6-dime
22
Al-Marzoqi et al. 33
Table 1. Cont'd
Antitumor, anti-inflammatory,
antifungal, pesticidal and insecticidal
58, 71, 81, 91, 109, 123, 149,
166, 185, 204, 219, 233, 248
336.241293
336
C19H32N203
12.877
2H-Benzo[f]oxireno[2,3-
E]benzofuran-8(9H)-one,9-
[[[2-(dimethylamin
23
Anti-inflammatory, antileishmanial
and antitrypanosomal
57, 68, 81, 95, 109, 123, 137,
151, 179, 208, 249, 278
338.318481
338
C22H42O2
13.953
Phytol, acetate
24
New chemical compound
60, 73, 85, 103, 127, 145, 163,
213, 262
279.077658
279
C10H17NO6S
14.399
Desulphosiniqrin
25
Anti-oxidant
55, 74, 87, 97, 111, 127, 155,
183, 199, 227, 264, 294
312.266445
312
C19H36O3
16.482
Oxiraneundecanoic acid ,3-
pentyl-,methyl ester , cis
26
Anti-cancer activities
57, 71, 81, 95, 111, 123, 137,
196, 221, 249, 278
296.307917
296
C20H40O
16.665
Phytol
27
34 J. Pharmacognosy Phytother.
Table 1. Cont'd
Antiviral and anti-obesity properties
55, 67, 79, 105, 129, 165, 185,
219, 265, 334, 440
440.29266
440
C28H40O4
18.296
9,12,15-Octadecatrienoic acid
, 2-phenyl-1,3-dioxan-5-yl
ester
28
Unknown
71, 91, 107, 122, 135, 151, 177,
213, 241, 299, 387, 418
440.29266
440
C24H34O6
18.874
Butanoic acid
,1a,2,5,5a,6,9,10,10a-
octahydro-5,5adihydroxy-4-(h)
29
Anti-spasmodic and immune
modulators
55, 69, 83, 98, 220, 264, 282,
339, 356, 393, 449, 489
884.78329
884
C57H104O6
19.846
9-Octadecenoic acid , 1,2,3-
propanetriyl ester , (E,E,E)-
30
Antimicrobial activity and Anti
oxidant.
57, 71, 83, 113, 132, 149, 167,
279, 390
390.27701
390
C24H38O4
20.373
Diisooctyl phthalate
31
New chemical compound
55, 69, 83, 96, 111, 149, 177,
209, 265, 304, 360, 420
420.251188
420
C24H36O6
21.449
8,14-Seco -3,19-
epoxyandrostane-8,14-
dione,17-acetoxy-3ß-methoxy
32
Al-Marzoqi et al. 35
Table 1. Cont'd
Widely used in the cosmetics
industry as an anti-wrinkle agent
69, 81, 95, 121, 149, 175, 203,
231, 257, 285, 341, 367, 395
410.391253
410
C20H50
22.604
Squalene
33
Used as a poultice as an anti-
inflammatory
74, 121, 227, 270, 298, 334
374.318481
374
C25H42O2
22.845
Cyclopropanebutanoic acid
,2-[[2-[[2-[(2-
pentylcyclopropyl)methyl]cycl
o
34
New chemical compound
55, 81, 125, 183, 239, 279, 321,
337, 379, 419, 458
476.38656
476
C30H52O4
23.159
Cyclotriaconta-1,7,16,22,-
tetraone
35
Antimicrobials and anti-virals
555, 91, 135, 173, 187, 239, 324
324.245316
324
C23H32O
23.451
2-[4-methyl-6-(2,6,6-
trimethylcyclohex-1-
enyl)hexa-1,3,5-trienyl]cyclo
36
Anti-diarrhoeal activity
69, 81, 95, 135, 203, 231, 271,
299, 357, 426
426.386166
426
C30H50O
23.657
Oxirane ,2,2-dimethyl-3-
(3,7,12,16,20-pentamethyl-
3,7,11,15,19,-hen
37
Anti mosquito larvicidal activity
55, 69, 81, 95, 109, 135, 203,
217, 286, 311, 365, 408, 424
468.39673
468
C32H52O2
23.686
9,19-Cyclolanost-24-en-3-
ol,acetate , (3ß)-
38
36 J. Pharmacognosy Phytother.
Table 1. Cont'd
Anti- inflammatory effects
55, 69, 122, 207, 236, 297357,
417, 477
536.262146
536
C28H40O10
25.025
9-Desoxo-9-x-acetoxy-3,8,12-
tri-O-acetylingol
39
anti-oxidant activity
57, 107, 151, 191, 205, 246, 274,
303, 344, 373, 416
416.365543
416
C28H48O2
25.236
y-Tocopherol
40
Anti-tumourogenic properties
135, 190, 207, 231, 249, 280,
298, 334, 352, 384, 439, 506
506.360739
506
C30H50O6
25.683
Olean-12-ene-
3,15,16,21,22,28-
hexol,(3ß,15α,16α,21ß,22α)-
41
Anti-oxidant activity
57, 69, 91, 121, 165, 205, 246,
274, 302, 330, 358, 386
430.38108
430
C29H50O2
26.581
Vitamin E
42
Campesterol is a phytosterol whose
chemical structure is similar to that
of cholesterol.
have anti-inflammatory effects.
55, 71, 81, 145, 161, 213, 255,
289, 315, 382, 400
400.370516
400
C28H80O
28.315
Campesterol
43
Anti-inflammatory
55, 70, 82, 98, 112, 171
171.064391
171
C6H9N3O3
3.224
Carbonic acid , ( ethyl)(1,2,4-
triazol-1-ylmethyl)diester
44
Al-Marzoqi et al. 37
Table 2. Zone of inhibition (mm) of Aspergillus Spp. test to Cassia angustifolia bioactive compounds and standard
antibiotics.
Plant/ antibiotics
Aspergillus spp.
Aspergillus niger
Aspergillus terreus
Aspergillus flavus
Aspergillus fumigatus
Cassia angustifolia
3.08±0.10
6.01±0.27
5.00±0.16
4.03±0.20
Amphotericin B
2.01±0.20
2.99±0.16
4.05±0.10
4.90±0.30
Fluconazol
4.08±0.61
2.96±0.14
3.00±0.81
4.90±0.40
Control
0.00
0.00
0.00
0.00
Figure 2. Structure of 2,5-dimethyl-4-hydroxy-3(2H)-
furanone present in Cassia angustifolia with RT= 4.883
using GC-MS analysis.
Figure 3. Structure of 2-Propyl-tetrahydropyran-3-ol
present in Cassia angustifolia with RT= 5.908 using GC-
MS analysis.
Figure 4. Structure of Estragole present in Cassia
angustifolia with RT= 6.303 using GC-MS analysis.
Figure 5. Structure of Benzene, 1-ethynyl-4- fluoro present in
Cassia angustifolia with RT= 6.720 using GC-MS analysis.
38 J. Pharmacognosy Phytother.
Figure 6. Structure of 5-Hydroxymethylfurfural present in Cassia
angustifolia with RT= 7.247 using GC-MS analysis.
Figure 7. Structure of Anethole present in Cassia angustifolia
with RT= 7.510 using GC-MS analysis.
Conclusion
From the results obtained in this study, it could be
concluded that C. angustifolia possesses remarkable
antimicrobial activity which is mainly due to 2-Propyl-
tetrahydropyran-3-ol, 1,2,2-Trimethylcyclopentane-1,3-
dicarboxylic acid and Diisooctyl phthalate. According to
these findings, it could be said that the methanol extract
act as antifungal agent.
Figure 8. Structure of 7-Oxabicyclo[4.1.0]heptan-2-one,6-
methyl -3-(1-methylethyl) present in Cassia angustifolia with
RT = 7.750 using GC-MS analysis.
Figure 9. Structure of 2-Methoxy-4-vinylphenol present in Cassia
angustifolia with RT= 7.933 using GC-MS analysis.
Conflict of Interests
The authors have not declared any conflict of interests.
Figure 10. Structure of 1,2,2-Trimethylcyclopentane-1,3-
dicarboxylic acid present in Cassia angustifolia with RT= 8.431
using GC-MS analysis.
Figure 11. Structure of E-9-Tetradecenoic acid present in Cassia
angustifolia with RT= 8.746 using GC-MS analysis.
Al-Marzoqi et al. 39
Figure 12. Structure of Caryophyllene present in Cassia
angustifolia with RT= 9.301 using GC-MS analysis.
Figure 13. Structure of Cholestan-3-ol,2-methylene-,(3ß,5α)
present in Cassia angustifolia with RT= 9.616 using GC-MS
analysis.
40 J. Pharmacognosy Phytother.
Figure 14. Structure of Benzene , 1-(1,5-dimethyl-4-hexenyl)-4-
methyl present in Cassia angustifolia with RT= 10.010 using GC-
MS analysis.
Figure 15. Structure of ß-curcumene present in Cassia angustifolia
with RT= 10.165 using GC-MS analysis.
Figure 16. Structure of 7-epi-cis-sesquisabinene hydrate present in
Cassia angustifolia with RT = 10.274 using GC-MS analysis.
Figure 17. Structure of Cyclohexene ,3-(1,5-dimethyl-4-hexenyl)-6-
methylene-,[S-(R*,S*)] present in Cassia angustifolia with RT=
10.508 using GC-MS analysis.
Figure 18. Structure of Octahydrobenzo[b]pyran,4a-acetoxy-
5,5,8a,-trimethyl present in Cassia angustifolia with RT= 10.771
using GC-MS analysis.
Figure 19. Structure of Dodecanoic acid , 3-hydroxy present in
Cassia angustifolia with RT= 11.218 using GC-MS analysis.
Al-Marzoqi et al. 41
Figure 20. Structure of Tetraacetyl-d-xylonic nitrile present in
Cassia angustifolia with RT= 11.012 using GC-MS analysis.
Figure 21. Structure of 1-Ethenyl 3,trans(1,1-dimethylethyl)-4,cis-
methoxycyclohexan-1-ol present in Cassia angustifolia with RT=
11.246 using GC-MS analysis.
42 J. Pharmacognosy Phytother.
Figure 22. Structure of Phen-1,4-diol,2,3-dimethyl-5-trifluoromethyl
present in Cassia angustifolia with RT= 11.378 using GC-MS
analysis.
Figure 23. Structure of 5-Benzofuranacetic acid,6-ethenyl -
2,4,5,6,7,7a-hexahydro-3,6-dime present in Cassia angustifolia with
RT= 12.036 using GC-MS analysis.
Figure 24. Structure of 2H-Benzo[f]oxireno[2,3-E]benzofuran-
8(9H)-one,9-[[[2-(dimethylamin present in Cassia angustifolia with
RT= 12.877 using GC-MS analysis.
Figure 25. Structure of Phytol, acetate present in Cassia
angustifolia with RT= 13.953 using GC-MS analysis.
Figure 26. Structure of Desulphosiniqrin present in Cassia
angustifolia with RT= 14.399 using GC-MS analysis.
Figure 27. Structure of Oxiraneundecanoic acid ,3-pentyl-,methyl
ester , cis present in Cassia angustifolia with RT= 16.482 using GC-
MS analysis.
Al-Marzoqi et al. 43
Figure 28. Structure of Phytol present in Cassia angustifolia with
RT= 16.665 using GC-MS analysis.
Figure 29. Structure of 9,12,15-Octadecatrienoic acid , 2-phenyl-
1,3-dioxan-5-yl ester present in Cassia angustifolia with RT= 18.296
using GC-MS analysis.
44 J. Pharmacognosy Phytother.
Figure 30. Structure of Butanoic acid, 1a,2,5,5a,6,9,10,10a-
octahydro-5,5adihydroxy-4-(h) present in Cassia angustifolia with
RT= 18.874 using GC-MS analysis.
Figure 31. Structure of 9-Octadecenoic acid , 1,2,3-propanetriyl
ester , (E,E,E) present in Cassia angustifolia with RT= 19.846 using
GC-MS analysis.
Figure 32. Structure of Diisooctyl phthalate present in Cassia
angustifolia with RT= 20.373 using GC-MS analysis.
Figure 33. Structure of 8,14-Seco -3,19-epoxyandrostane-8,14-
dione,17-acetoxy-3ß-methoxy present in Cassia angustifolia with
RT= 21.449 using GC-MS analysis.
Figure 34. Structure of Squalene present in Cassia angustifolia
with RT= 22.604 using GC-MS analysis.
Figure 35. Structure of Cyclopropanebutanoic acid, 2-[[2-[[2-[(2-
pentylcyclopropyl)methyl]cyclo present in Cassia angustifolia with
RT= 22.845 using GC-MS analysis.
Al-Marzoqi et al. 45
Figure 36. Structure of Cyclotriaconta-1,7,16,22,-tetraone present
in Cassia angustifolia with RT= 23.159 using GC-MS analysis.
Figure 37. Structure of 2-[4-methyl-6-(2,6,6-trimethylcyclohex-1-
enyl)hexa-1,3,5-trienyl]cyclo present in Cassia angustifolia with RT=
23.451using GC-MS analysis.
46 J. Pharmacognosy Phytother.
Figure 38. Structure of Oxirane ,2,2-dimethyl-3-(3,7,12,16,20-
pentamethyl-3,7,11,15,19,-hen present in Cassia angustifolia with
RT= 23.657 using GC-MS analysis.
Figure 39. Structure of 9,19-Cyclolanost-24-en-3-ol,acetate , (3ß)
present in Cassia angustifolia with RT= 23.686 using GC-MS
analysis.
Figure 40. Structure of 9-Desoxo-9-x-acetoxy-3,8,12-tri-O-
acetylingol present in Cassia angustifolia with RT= 25.025 using
GC-MS analysis.
Figure 41. Structure of y-Tocopherol present in Cassia angustifolia
with RT= 25.236 using GC-MS analysis.
Figure 42. Structure of Olean-12-ene-3,15,16,21,22,28-
hexol,(3ß,15α,16α,21ß,22α) present in Cassia angustifolia with RT=
25.683 using GC-MS analysis.
Figure 43. Structure of Vitamin E present in Cassia angustifolia
with RT= 26.581 using GC-MS analysis.
Al-Marzoqi et al. 47
Figure 44. Structure of Campesterol present in Cassia angustifolia
with RT= 28.315 using GC-MS analysis.
Figure 45. Structure of Carbonic acid, ( ethyl)(1,2,4-triazol-1-
ylmethyl)diester present in Cassia angustifolia with RT= 3.224 using
GC-MS analysis.
48 J. Pharmacognosy Phytother.
ACKNOWLEDGEMENT
The authors thank Dr. Abdul-Kareem Al-Bermani,
Lecturer, Department of Biology, for valuable suggestions
and encouragement.
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