Journal of Pharmacognosy and Phytochemistry 2019; 8(2): 1546-1551

E-ISSN: 2278-4136
P-ISSN: 2349-8234
JPP 2019; 8(2): 1546-1551 Comparative phytochemical and anti-oxidant (in
Received: 12-01-2019
Accepted: 15-02-2019 vitro) assessment of different aerial parts viz.
Ishita Gupta
leaves, bark and pods of Cassia fistula
Department of Chemistry,
School of Basic and Applied
Sciences, Maharaja Agrasen Ishita Gupta and Punita Sharma
University, Baddi, Solan,
Himachal Pradesh, India Abstract
Cassia fistula, also known as Indian Laburnum, is found throughout Asia including India. It is a
Punita Sharma
medicinal plant of great importance because of its power of healing countless disorders. The work
Department of Chemistry,
School of Basic and Applied
presented in this paper is performed keeping in mind the high therapeutic value of C. fistula. For
Sciences, Maharaja Agrasen achieving this objective, methanol extract of different parts viz. bark, pods and leaves of C. fistula were
University, Baddi, Solan, prepared and subjected to antioxidant assay employing in-vitro hydrogen peroxide scavenging assay and
Himachal Pradesh, India reducing power assay. Methanol extract of the pods showing maximum anti-oxidant activity was used for
isolation of bioactive compounds namely Rhein, Emodin and Chrysophanic acid (anthraquinones),
Catechin (tannin) and Luteolin (flavonoid).

Keywords: Phytoconstituents, H2O2 scavenging, reduction potential, anti-oxidant

Introduction
Majority of the population of developing countries depends on their traditional medicinal
system, especially plant-based, as they are less toxic and has no/less side effects [1]. Cassia
fistula is among 3000 medicinal plants that have been used in Unani, Ayurvedic and traditional
herbal medicinal system of India for curing various disorders/ailments because of its high
therapeutic potential [2]. Cassia fistula (Amaltas) belongs to the Leguminosae family, grows
throughout India and is also known as golden shower because of its beautiful bunch of yellow
flowers. A moderate sized tree that grows up to 24m, ascending up to an altitude of 1,220-
1300m in the sub Himalayan tract and outer Himalayas. The fruits of C. fistula are long
cylindrical pods filled with dark brown sweet, sticky pulp consisting of seeds. C. fistula tree
has rough and dark brown bark and its bright green leaves are pinnate. It is found in
Bangladesh, China, Hong Kong, Sri Lanka, Burma, Philippines, Malaysia, Indonesia,
Thailand, South Africa, Mexico, East Africa and Brazil. C. fistula has been reported to treat
many skin, liver and gastro-intestinal disorders. It is also used to cure tumors of abdomen,
glands, throat cancer, convulsions, dysuria, epilepsy, tumours, leprosy and syphilis and treats
rheumatism [3-4]. Previous studies show that the plant contains anthraquinones and its
derivatives, tannins, flavonoids and sterols possessing different biological activities isolated
from different parts of C. fistula [5-9]. Rhein is the major constituent isolated from different
parts of this plant and is reported to have anti-cancer activity [10]. Flavonoids and chromones
exhibiting anti-tobacco mosaic virus activity (anti-TMV) were reported from the bark and
stems of C. fistula [11-13]. Essential oil from the flowers, leaves, pulp and seeds possesses
hemolytic and anti-fungal activity [12-15]. Amentoflavone, a biflavonoid, present in the leaf
extract of Cassia fistula possesses cytotoxicity and anti-oxidant potential [16]. The plant has
also been reported to possess anti-diabetic, anthelmintic, anti-tussive, anti-pyretic, anti-
oxidant, hepatoprotective, anti-microbial, anti-fertility, anti-leishmmaniatic, neuroprotective,
anti-ulcer activities, anti-aging properties and nephroprotective effect [17-23]. Plant extracts,
now-a-days, are finding applications in various fields of research like nanoparticle synthesis,
polymer synthesis etc. Synthesis of Silver nanoparticles from C. fistula leaf extract has been
reported, which shows anti-microbial, anti-oxidant and anti-cancer properties besides their
application in chemical sensors [24-25].
On the basis of phytochemical screening done previously, it was found that the pods, bark,
Correspondence
Punita Sharma leaves and seeds collected from the Baddi region of Himachal Pradesh are rich in phenolic
Department of Chemistry, compounds like Tannins, Terpenoids, Flavonoids, Steroids and Anthraquinones. However,
School of Basic and Applied Saponins are completely absent in the plant [26]. It was concluded that the pods of C. fistula is
Sciences, Maharaja Agrasen enriched with phenolic components, which is our major area of concern. So, present study
University, Baddi, Solan,
aims at exploring bark, leaves and pods of C. fistula phytochemically and biologically.
Himachal Pradesh, India
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This paper presents the preliminary anti-oxidant assessment Isolation of Pure Compounds
of crude extracts of different parts of Cassia fistula viz. bark, For the isolation of phytoconstituents, the crude methanol
leaves and pods and isolation of the phenolic constituents extract of the pods of Cassia fistula was subjected to repeated
responsible for the anti-oxidant potential of the plant column chromatography over silica gel (60-120 mesh,
employing in-vitro methods like reducing power assay and stationary phase) and eluted with solvents (mobile phase) of
hydrogen peroxide scavenging assays. varying polarity, starting initially with petroleum ether,
followed by combination of petroleum ether: ethyl acetate
Material and Methods ranging from 95:5 then increasing 5 parts of ethyl acetate each
All the chemicals and organic solvents used were of LR/AR time. Polarity of solvent system was further increased by
grade purchased from SD Fine-Chemicals. Ceric ammonium adding 5 parts of Chloroform to 95 parts of ethyl acetate and
sulphate and iodine (SD Fine) were used as visualizing spray increasing the Chloroform part in multiples of 5. Further,
reagents. Silica Gel (60-120; 100-200 mesh, SD Fine) used polarity was increased by eluting the column with the
for column chromatography; precoated TLC aluminium combination of Chloroform: Methanol ranging from 95:5 and
sheets (Merck) were used for qualitative and quantitative increasing concentration of methanol in multiples of 5 to give
TLC. Melting points were determined in soft glass capillaries a total of 318 fractions of 250 ml each. Fractions were dried
in an electrothermal melting point apparatus. Double beam on rotary vacuum evaporator and subjected to TLC.
UV-VIS Spectrophotometer (LABTRONICS model LT-2700) Fractions 80-96 eluted in chloroform: ethyl acetate:: 1:1
ranging between 190-1100 nm was used. The 1H-NMR showed similar pattern on TLC giving a major single spot,
spectra was recorded on Bruker Avance- II, 400 MHz NMR fractions 110-119 eluted in CHCl3: methanol:: 4:1 showed
instrument. The chemical shifts (δ) were expressed as parts similar pattern on TLC giving major single spot, fractions
per million (ppm) and the coupling constants (J) were 139-156 eluted in CHCl3: Methanol:: 3:2 showed similar
recorded as hertz (Hz). DMSO, CDCl3 and Methanol were pattern on TLC giving major single spot, fractions 229-256
used as solvent and TMS was used as internal standard. eluted in CHCl3: Methanol:: 1:4 showed similar pattern on
TLC giving a major single spot and fractions 310-316 eluted
Collection, Processing and Extraction of Plant Material in methanol showed major single spot on TLC. The spots
Aerial parts of Cassia fistula viz. bark, pods and leaves were were analyzed using iodine vapors and ceric ammonium
collected from the campus of Maharaja Agrasen University, sulfate as visualizing reagents and TLCs were monitored
Baddi, India. Plant material was shade dried and kept free under UV cabinet. Fractions showing similar pattern were
from unwanted matter and contaminants. The shade dried pooled, dried, purified on preparative TLC and recrystallized
plant material was crushed into coarse powder and was giving a total of five pure compounds namely Rhein, Emodin,
extracted with methanol in soxhlet for forty-eight hours and Chrysophanic acid, Catechin and Luteolin and their melting
dried under reduced pressure to yield hot methanol extract. points were recorded further which were subjected to
The dried methanol extract of the pods of Cassia fistula was spectroscopical analysis (Fig.1).
taken for isolation of pure compounds using various
chromatographic techniques like column chromatography,
TLC and preparative TLC.

Fig 1: Structures of compounds isolated

In-Vitro Assessment of Anti-Oxidant Activity spectrophotometer. The methanol extract samples of different
Hydrogen Peroxide Scavenging Assay aerial parts of C. fistula were prepared at concentrations
The ability of plant extracts (containing a large number of varying from 10, 20, 30, 40, 50 mg/ml by dissolving them in
phenolics) to scavange H2O2 was estimated according to the distilled water and mixture of hydrogen peroxide and
method of Ruch et al. described by Alam et al. [27-28]. A phosphate buffer was added. The absorbance of the reaction
40mM solution of Hydrogen Peroxide was prepared in 50mM mixture at 230 nm was determined after 10 minutes. The
phosphate buffer (pH 7.4) whose concentration was percentage of Hydrogen Peroxide Scavenging by the extracts
determined from Hydrogen peroxide calibration curve by was calculated as follows:
measuring absorbance at 230 nm using UV-VIS
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% scavenged (H2O2) = [(Ac – As)/Ac] x 100 (dd, 1H, H-4a), 2.70 (dd, 1H, H-4e), 4.43 (d, 1H, J = 7.91 Hz,
H-2),4.61 (m, 1H, H-3),5.55 (d, 1H, J= 2.51 Hz, H-6), 5.77
Where Ac is the absorbance of the control (without test (d, 1H, J= 2.51 Hz, H-8), 6.71 (dd, 1H, H-6′), 6.79 (d, 1H, J =
sample) and As is the absorbance of the test sample. All 1.81 Hz, H-2ʹ), 6.89 (d, 1H, J = 8.21 Hz, H-5′) and 8.16 (m,
experiments were performed in triplicates. 5H, -OH).

Determination of the Reducing Power Luteolin: Yellow solid, Melting point- 259 °C, Molecular
Previous reports show that the reducing power was associated formula [C15H10O6], IUPAC name- 3ʹ,4ʹ,5,7-
with anti-oxidant activity which was due to the presence of tetrahydroxyflavone. 1H-NMR (400 MHz, DMSO):- δ 6.14 (s,
anthraquinones, flavonoids and other polyphenolic 1H, H-6), 6.36 (s, 1H, H-8), 6.67 (s, 1H, H-3), 6.81 (d, 1H, J=
compounds. For determination of reducing potential of 8.91 Hz, H-5ʹ), 7.03 (d, 1H, J= 2.16 Hz, H-2ʹ), 7.28 (m, 1H,
methanol extracts of bark, leaves and pods of C. fistula, H-6ʹ) and 8.07 (m, 4H, -OH).
method described by Oyaizu was applied [28-30]. Substances
having reduction potential can react with potassium Hydrogen Peroxide Assay
ferricyanide (Fe3+) to form potassium ferrocyanide (Fe2+). The ability of the plant extracts to scavenge hydrogen
When ferric-chloride (FeCl2) was added to reaction mixture, peroxide may be attributed to their phenolic contents that can
the potassium ferrocyanide (Fe2+) reacts with it and produces donate electrons to hydrogen peroxide, thus neutralizing it to
a ferric-ferrous complex which can be spectrophotometrically water. The extracts were capable of scavenging hydrogen
measured at 700 nm. Various concentrations of plant extracts peroxide in a concentration-dependent manner. Although
ranging from 10µg-50µg (10, 20, 30, 40 and 50µg) were hydrogen peroxide itself is not very reactive, it can sometimes
prepared in methanol. Mixture of 0.2 M Phosphate Buffer cause cytotoxicity by giving rise to hydroxyl radicals in the
(5ml, pH 6.6) and plant extract was added to 1% potassium cell. Thus, removal of H2O2 from food systems is an
ferricyanide (5ml) and incubated for 20 min at 50 °C. 5ml of important issue.
10% trichloroacetic acid (TCA) solution was added to the The scavenging activity of methanol extract of bark, leaves
incubated reaction mixture and centrifuged for 10 min at and pods of C. fistula at different concentrations is shown in
3000g. Supernatant (5ml) was mixed with distilled water Fig. 2. The results clearly depicts that all the extracts can
(5ml) and 1% ferric chloride (1ml). Absorbance of the scavenge H2O2 to good extent. The scavenging potential of
resulting reaction mixture was measured at 700nm. Increase H2O2 increases with the increase in the concentration for all
in the absorbance indicated increase in reducing power which the aerial plant parts. At 30mg/ml, the percentage inhibition is
is associated with anti-oxidant activity. All the tests were above 50% for all the methanol extracts of aerial parts of the
carried out in triplicates. plant. At 10mg/ml, 20mg/ml concentration, all the methanol
extracts except that of leaves exhibit more than 50%
Results scavenging activity. The pods showed good scavenging
Methanol extract of pods of C. fistula contains rhein, emodin, activity at almost all the concentrations but at 40mg/ml and
chrysophanic acid, catechin and luteolin that were isolated 50mg/ml it almost scavenged H2O2 completely indicating
and identified by using various chromatographic and these to be a good antioxidant. The inhibiting percentage of
spectroscopical techniques (Fig. 1).The experimental data of methanol extracts of all the parts is in the following order:
isolated compounds is as under:- pods > bark> leaves.

Rhein: Yellowish orange solid, Melting Point- 328 °C, Reducing Power Assay
Molecular Formula [C15H8O6], IUPAC name- 1,8- The higher value of absorbance at 700 nm indicates stronger
dihydroxyanthraquinone-3-carboxylic acid. 1H-NMR (400 reducing power of the samples. The reduction potential of
MHz, DMSO) :- δ 7.34 (d, 1H, J = 8.58 Hz, H-5), 7.62 (m, different parts of C. fistula viz. bark, leaves and pods and that
1H, H-6), 7.65 (s, 1H, H-4), 7.76 (d, 1H, J = 8.17 Hz, H-7), of L-ascorbic acid at various concentrations is illustrated in
8.02 (s, 1H, H-2), 11.43 (s, 1H, -OH), 11.81 (s, 1H, -OH). Fig. 3. At low concentration, all the methanol extracts of
different parts of the plant have shown good reducing power
Emodin: Orange solid, Melting Point- 236oC, Molecular as compared to that of standard i.e. L-ascorbic acid, but at
Formula [C15H10O5], IUPAC Name- 6-methyl-1,3,8- high concentration, reducing power of extracts is less as
trihydroxyanthraquinone. 1H-NMR (400 MHz, DMSO):- δ compared to L-ascorbic acid. The reducing powers of the
2.58 (s, 3H, -CH3), 6.78 (s, 1H, H-2), 7.45 (d, 1H, J= 2.68 Hz, samples are in the following order: pods > bark > leaves. The
H-7), 7.91 (d, 1H, J= 2.68 Hz, H-5), 7.99 (s, 1H, H-4), 8.31 reducing power of pods of C. fistula is better than bark and
(s, 1H, -OH), 12.03 (s, 1H, -OH), 12.18 (s, 1H, -OH). leaves and comparable with L-ascorbic acid at every
concentration indicating it to be a good reducing agent as
Chrysophanic Acid: Yellow solid, Melting Point- 324 °C, compared to bark and leaves. There is continuous increase in
Molecular Formula [C15H10O4], IUPAC name- 1,8-dihyrdoxy- the absorbance of methanol extracts of the all the parts of
3-methyl-9,10-anthraquinone. 1H-NMR (400 MHz, DMSO):- Cassia fistula with the increase in its concentration which has
δ 2.51 (s, 3H, -CH3), 7.06 (s, 1H, H-2), 7.14 (s, 1H, H-4), 7.41 same pattern as that of L-ascorbic acid. Present investigation
(d, 1H, J = 8.0 Hz, H-5), 7.58 (m, 1H, H-6), 7.82 (d, 1H, J = reveals that the reducing powers of the methanol extracts of
8.0 Hz, H-7), 11.55 (s, 1H, -OH), 11.68 (s, 1H, -OH) all the parts of C. fistula also increases with the increase in
their concentrations. So, it can be concluded that all the parts
Catechin: Pale yellow solid, Melting point- 181 °C, of the plant exhibited increase in their reducing potential in
Molecular Formula [C15H14O6], IUPAC name- 3ʹ,4ʹ,5,7- concentration dependent manner.
tetrahyroxyflavan-3-ol. 1H-NMR (400MHz, DMSO):- δ 2.38

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Journal of Pharmacognosy and Phytochemistry

Fig 2: Percentage H2O2 Scavenging activity exhibited by methanol extracts of bark, pods and leaves at different concentrations

Fig 3: Reducing potentials of extracts of bark, leaves and pods of C. fistula at different concentrations.

Discussion were characterized using various spectroscopic techniques

The results of the H2O2 scavenging assay and reducing power and comparing them with Literature [6, 7, 31].
assay shows that bark, leaves and pods of C. fistula possesses
good free radical scavenging potential against H2O2 and Rhein: The 1H-NMR spectrum shows single peaks at δ11.81
reducing potential because all the aerial parts (bark, leaves (s) and 11.43 (s) attributed to hydrogen of hydroxyl group
and pods) have shown positive results for the bioactivities attached at position C-8 of ring A and C-1 of ring C
employed, indicating these to be good anti-oxidants. The respectively of the anthraquinones moiety. Singlet at δ8.02
maximum scavenging potential against H2O2 and reducing corresponds to H -2 which is downfield due to deshielding
potential was displayed by the pods of C. fistula. As a result, effect of –OH group and –COOH groups attached to
methanol extract of C. fistula pods was taken for isolation of neighouring carbons at C-1 and C-3 respectively. Singlet at
secondary metabolites targeting anthraquinones, flavonoids δ7.65 corresponds to H-4 of aromatic ring C showing
and tannins using chromatographic techniques which results downfield shift due to the presence of neighbouring –COOH
in isolation of pure compounds namely Rhein, Emodin, group. Multiplet at δ7.62 corresponds to H-6 and doublet at
Chrysophanic acid, Catechin and Luteolin whose structures δ7.76 and δ 7.34 corresponds to H-7 and H-5 of ring A
respectively.
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Journal of Pharmacognosy and Phytochemistry

Emodin: The 1H-NMR spectrum show peaks at δ12.18 (s) Chrysophanic acid), tannin (Catechin) and flavonoids
and 12.03 (s) that correspond to hydrogen of hydroxyl group (Luteolin).
attached at C-8 and C-1 of rings A and C respectively. Singlet
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