Free Radicals and Antioxidants 3 (2013) 107e112

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Free Radicals and Antioxidants

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Short communication

Chemical constituents, in vitro antioxidant and antimicrobial potential

of Caryota urens L.
Devanesan Arul Ananth a, Thilagar Sivasudha a, *, Angappan Rameshkumar b,
Ramachandran Jeyadevi a, Smilin Bell Aseervatham a
a
Department of Environmental Biotechnology, Bharathidasan University, Tiruchirappalli 620 024, Tamil Nadu, India
b
Pesticide Residue Analysis Laboratory, Regional Plant Quarantine Station, Chennai 600 027, Tamil Nadu, India

a r t i c l e i n f o a b s t r a c t

Article history: Objective: To evaluate chemical constituents, in vitro antioxidant and antimicrobial potential of Caryota
Received 4 April 2013 urens L.
Accepted 23 May 2013 Methods: Qualitative analysis of crude extract of C. urens was carried out by gas chromatography mass
Available online 20 August 2013
spectrometry (GCeMS) method and their in vitro antioxidant activity was evaluated using DPPH, ABTS,
reducing power and nitric oxide scavenging assays. Antimicrobial activity was determined by disc
Keywords:
diffusion method.
C. urens
Results: GCeMS analysis showed the presence of fatty acids, aliphatic, aromatic and phenolic acids. The
Antioxidant activity
Antimicrobial activity
antioxidant activity of immature fruit and leaf extracts yielded high activity when compared to the fruit
ABTS skin. The fruit skin and immature fruit of C. urens exhibited strong antibacterial activity against the tested
GCeMS pathogens (Escherichia coli, Vibrio cholerae, Salmonella typhii, Staphylococcus aureus and Shigella flexneri)
when compared to leaf.
Conclusion: In our results, we suggest that C. urens extracts have strong antioxidant and antimicrobial
potential. The identified bioactive compounds of C. urens could be attributed to antioxidant and anti-
microbial property.
Copyright Ó 2013, SciBiolMed.Org and Phcog.Net, Published by Reed Elsevier India Pvt. Ltd. All rights
reserved.

1. Introduction suspected to be carcinogen. Moreover, the currently available

synthetic antibiotics exhibit certain demerits and side effects. It has
Free radicals are reactive oxygen and nitrogen species (ROS/ been demonstrated that the antimicrobial effects of the plant
RNS) that are continuously produced in human body as a byproduct derived compounds cause structural or functional damage to the
of cellular aerobic respiration. Over production of ROS/RNS leads an bacterial cell membrane through various mechanisms of actions
exposure to external oxidant substances, failure in the defense that attack the phospholipid bilayer of the cell membrane and
mechanism or damage to biomolecules such as DNA, lipids or disrupt enzyme systems.4 Therefore interest has been considerably
proteins.1 Antioxidants are the agents capable of effectively increased in finding naturally occurring antioxidant and antimi-
neutralizing these free radicals by interfering with oxidation pro- crobial compounds suitable for use in food and medicine.5e7
cess, chelating catalytic metals and also by acting as oxygen scav- Caryota urens belongs to the family Arecaceae (Palmae) and the
engers.2 Previous reports suggest that the natural plant genus Caryota consist of 27 species widely distributed throughout
phytocompounds are source of excellent antioxidant agent to Asia.8,9 C. urens was commonly known as wild coconut and wine
prevent oxidative damage caused by free radicals and thereby palm. The plant products have admirable medicinal properties, and
reduce the risk of several disorders including cancer, atheroscle- are used for the treatment of various ailments in the ayurvedic
rosis, arthritis, central nervous system injury and degenerative medical system practiced in Sri Lanka. The palm juices are used to
disorders.3 Since the currently used synthetic antioxidants butyl- treat seminal weakness and urinary disorders. In traditional med-
ated hydroxy anisole (BHA), butylated hydroxy toluene (BHT) were icine, porridge prepared from C. urens flower is used to treat gastric
ulcer; migraine headaches, root bark and the cabbage or terminal
bud of the palm to treat rheumatic swellings and snake bite.10 Bark
* Corresponding author. Tel.: þ91 431 2407088; fax: þ91 (0) 431 2407045. and seed used to treat boils and the root is used for tooth ailments.
E-mail addresses: [email protected], [email protected] (T. Sivasudha). Palm sap collected from the inflorescence is fermented with mixed

2231-2536/$ e see front matter Copyright Ó 2013, SciBiolMed.Org and Phcog.Net, Published by Reed Elsevier India Pvt. Ltd. All rights reserved.
http://dx.doi.org/10.1016/j.fra.2013.05.008
108 D. Arul Ananth et al. / Free Radicals and Antioxidants 3 (2013) 107e112

inoculum of yeast to obtain toddy. However, no reports have been 2.4. Total flavonoid content
concerning the antioxidant and antimicrobial activity of C. urens.
Therefore, the aim of the present study was to compare and The total flavonoid content of plant extract was determined by
investigate chemical constituents and antimicrobial and antioxi- Liu et al method12 with slight modifications. Plant methanolic
dant activity of the leaves, immature fruits and mature fruit skin of extract (0.5 mL) was added with 2.5 mL of distilled water fol-
C. urens. lowed by addition of sodium nitrite (0.150 mL, 5%). This solution
mixture was incubated for 6 min at room temperature then
2. Materials and methods aluminum chloride (10%, 0.3 mL) was added and allowed to stand
for 5 min. Finally, 1 mL of 1 M sodium hydroxide was added and
2.1. Plant sample collection and extraction made up the volume to 5 mL with distilled water. The absorbance
was read at 510 nm using UV-Spectrophotometer. Total flavonoid
Fresh C. urens plant material (leaf, immature fruits and fruit content was expressed as milligram of rutin equivalents (mg of
skin) were collected from Bodi mettu (Western Ghats), Tamil Nadu, RE/g of extract).
India, which was authenticated by Dr. D. Stephen, Taxonomist, The
American College, Madurai, Tamil Nadu, India. The plant samples
were washed with distilled water and shade dried for three weeks
2.5. In vitro antioxidant activity
(Fig. 1). After shade drying, the samples were ground to fine pow-
der. 10 g of each sample powder extracted with 200 mL of methanol
2.5.1. DPPH radical scavenging activity
using Soxhlet apparatus for 14e16 h at solvent boiling temperature.
1,1-Diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activ-
Then the extract was concentrated using rotary evaporator at 50 C.
ity was estimated using the method of Liana-Pathirana and Sha-
Extracts were stored at 20 C until further use.
hidi.13 Appropriate dilutions of the extract (1 mg/mL) was mixed
with, 1 mL of 0.135 mM methanolic solution of DPPH radical.
2.2. GCeMS analysis
Absorbance was measured at 517 nm after 30 min of reaction. BHT
was used as reference standard and the inhibition percentage was
GC/MS analysis of the methanol extracts was performed using a
calculated using the following formula:
Shimadzu QP-2010 Plus with Thermal Desorption System TD 20. For
MS detection, the electron ionization mode with ionization energy
of 70 eV was used, with a mass range at m/z 50e550. An HP-5MS Percentage of inhibition ¼ ½ðAbs control
capillary column was used for GC/MS. Helium was used as carrier Abs sample=Abs controlÞ
gas. Essential compounds were identified by their retention times 100
and mass fragmentation patterns using data of standards at
WILEY8.LIB.

2.3. Total phenolics content 2.5.2. ABTS radical scavenging activity

Determination of 2, 2 -azino-bis (3-ethylbenzthiazoline)-6-
Plant total phenolics content was estimated using Singleton and sulfonic (ABTS) radical scavenging ability of plant extracts was
Rossi11 standard protocol with some modifications. FolineCiocalteu carried out by the method of Re et al.14 Previously, 7 mM ABTS
reagent (0.5 mL) was added to 0.1 mL of the methanol extract prior solution and 2.4 mM potassium persulphate solution were pre-
to the addition of 7 mL of distilled water. The mixture was incu- pared separately. Equal amount of two stock solutions were
bated in dark for 5 min at room temperature. To this mixture, 1.5 mL mixed and allowed to stand for 12 h in dark at room temperature.
of sodium carbonate solution was added and incubated for 2 h at About 1 mL of diluted ABTS.þ solution react with plant extract
room temperature. The absorbance of blue color was read at (5e25 mg/mL) after 10 min the absorbance was measured UV-
765 nm using UV-Spectrophotometer. Total phenolics content of spectrophotomatrically at 734 nm against the blank solution.
the methanol extract was calculated as gallic acid equivalents (mg ABTS free radical inhibition was calculated by following
of GAE/g of extract). equation:

Fig. 1. C. urens (Wine palm) Plant.

D. Arul Ananth et al. / Free Radicals and Antioxidants 3 (2013) 107e112 109

Table 1 2.7. Statistical analysis

Total phenolics and flavonoid content of methanolic extract of C. urens.

Plant extracts Total phenols Total flavonoids Experimental results were expressed as mean SD of three
(mg GAE/g dw)a (mg RE/g dw)a parallel measurements. The results were processed using Microsoft
Leaf 15.00 0.40 15.35 0.41 Excel 2007 and Origin 6.0.
Immature fruit 17.63 0.51 11.29 0.54
Fruit skin 10.23 0.40 13.58 0.40 Table 2
GAE/g dw e gallic acid equivalents/g dry weight; RE/g dw e rutin equivalents/g dry Profiling chemical constituents of C. urens through GCeMS analysis.
weight.
a Peak R.Ta %b MWc MFd Compound name
Data are presented as the mean standard deviation of three determinations.
(a) Leaf
1 11.160 0.19 112 C7H12O 4-Hexen-2-one, 3-Methyl-
Percentage of inhibition ¼ ½ðAbs control 2 12.147 0.84 114 C6H10O2 Hexanoic acid
3 15.499 3.15 273 C13H23NO5 Dodecanoic acid
Abs sample=Abs controlÞ 4 16.648 0.49 129 C6H11NO2 Nitrous acid
100 5 19.315 0.81 99 C5H9NO N-Ethyl acrylamide
6 20.683 0.34 188 C9H16O4 Butyl propyl ester
7 20.952 4.78 270 C17H34O2 Pentadecanoic acid
8 23.693 0.88 164 C9H8O3 Benzoic acid
9 25.096 1.39 382 C25H50O2 Lignoceric acid
2.5.3. Nitric oxide scavenging activity 10 25.577 1.25 296 C19H36O2 11-Octadecenoic acid
Garratt,15 method was adopted to determine the nitric oxide 11 26.836 0.59 294 C19H34O2 9,12-Octadecadienoic acid
radical scavenging activity of plant extract. The reaction mixture 12 28.512 1.79 292 C19H32O2 Linolenic acid
13 29.187 1.38 143 C6H9NO3 Pyroglutamic acid
contained 2 mL of 10 mM Sodium nitroprusside, 0.5 mL of phos-
14 29.549 10.27 398 C26H54O2 Palmitaldehyde
phate buffered saline (pH- 7.4) and plant extract (100e500 mg/mL). 15 30.508 0.23 116 C6H12D2N2 1,3-Cyclohexane-1,3-D2-diamine
The final volume of the solution was made up to 3 mL with 16 31.186 0.66 146 C8H18O2 3,4-Hexanediol
distilled water. After incubation for 150 min at 25 C, 0.5 mL of the 17 31.792 0.53 83 C5H9N Aziridine
incubated solution was taken and 1 mL sulphanilic acid (0.33% in 18 35.098 28.51 284 C18H36O2 Stearic acid
19 38.709 1.24 126 C7H10O2 2-Oxabicyclo[3.2.1]octan-3-one
20% glacial acetic acid) was added and allowed to stand for 5 min.
20 41.344 10.81 282 C18H34O2 Cyclohexyl ester
Then 1 mL of 0.1% of napthylethylenediamine dihydrochloride (w/ 21 42.448 12.00 282 C18H34O2 Oleic acid
v) was added and the mixture was incubated for 30 min at room 22 44.773 12.86 182 C11H18O2 10-Undecenoic acid
temperature. The pink color chromophore formed was measured 23 48.284 5.01 154 C9H14O2 8-Nonynoic acid
(b) Immature fruit
at 540 nm and the results were expressed as percentage of
1 12.109 1.50 98 C5H6O2 Cyclopentanone
inhibition. 2 13.959 0.58 140 C9H16O 1,8-Nonadien-4-Ol
3 16.795 0.39 94 C6H6O Phenol, Acide carbolique
2.5.4. Reducing power activity 4 20.418 0.50 150 C9H10O2 2-Methoxy-4-vinylphenol
Oyaizu16 standard method was used for determination of 5 20.949 1.21 270 C17H34O2 Pentadecanoic acid
6 21.656 0.38 154 C8H10O3 Pyrogallol 1,3-dimethyl ether
reducing power capacity of plant extract. The reaction mixture
7 23.688 0.79 222 C12H14O4 Phthalic acid
contains 2.5 mL of 0.2 M Phosphate buffered saline (pH-6.6) and 8 25.577 1.50 296 C19H36O2 11-Octadecenoic acid
2.5 mL of 1% potassium ferricyanide To this mixture, plant extract 9 26.844 0.97 156 C10H20O Decylenic alcohol
(100e500 mg/mL) was added and incubated for 20 min at 50 C. 10 29.179 0.71 143 C6H9NO3 Pyroglutamic acid
Then, 2.5 mL of 10% trichloro acetic acid was added. This mixture 11 31.144 20.01 222 C15H26O (2E,6E)-Farnesol
12 33.501 0.42 138 C10H18 1,5-Heptadiene
was centrifuged for 10 min at 3000 rpm. The upper layer (2.5 mL) 13 35.026 28.26 284 C18H36O2 Stearic acid
was collected and dissolved in 2.5 mL of distilled water. Finally, 14 36.020 1.23 254 C16H30O2 Cyclopentaneundecanoic acid
0.5 mL of 0.1% ferric chloride was added and absorbance was 15 37.956 0.36 114 C6H10O2 3-Butenoic acid
measured UV-Spectrophotometrically at 700 nm. 16 41.251 7.14 256 C16H32O2 Palmitic acid
17 42.318 15.96 282 C18H34O2 Oleic acid
18 44.571 18.09 182 C11H18O2 Hendecynoic acid
2.6. Antimicrobial activity (c) Fruit skin
1 9.877 1.75 298 C18H19FOSi 4-Fluorobenzoyl
2 12.182 0.36 70 C5H10 Cyclobutane
2.6.1. Test microorganisms 3 13.318 0.98 73 C3H7NO Isoxazolidine
Bacterial cultures such as Escherichia coli (MTCC 1687), Vibrio 4 13.943 1.12 103 C4H9NO2 Nitrous acid
cholerae (MTCC 3906), Salmonella typhii (MTCC 531), Staphylococcus 5 16.442 0.74 146 C7H18Osi 1-Propanol
6 17.972 0.59 326 C12H23IO2 Dodecanoic acid
aureus (MTCC 96) and Shigella flexneri (MTCC 1457) were obtained
7 19.384 0.74 404 C9H18Br2O4Si2 Propanedioic acid
from microbial type culture collection (MTCC), Indian Institute of 8 19.698 0.40 200 C10H16O4 Oxalic acid
Microbial Technology, Chandigarh, India. 9 20.966 1.39 130 C7H14O2 Hexanoic acid
10 21.745 0.72 58 C4H10 Isobutane
2.6.2. Disc diffusion method 11 22.147 0.64 404 C9H18Br2O4Si2 Bis(trimethylsilyl) ester
12 25.121 0.33 89 C3H7NO2 Isonitropropane
The antimicrobial activity of C. urens methanol extract was 13 25.609 0.71 100 C6H12O Oxetane
assessed by the disc diffusion technique.17 Mueller Hinton agar 14 26.869 0.81 182 C11H18O2 8-Nonynoic acid
plates were prepared and individually swabbed with pathogenic 15 29.217 0.34 146 C5H10N2O3 Levoglutamide
microorganisms. The sterile discs (6 mm) were placed over surface 16 29.668 0.90 264 C14H24OSi2 2,2-Bis(trimethylsilyl)styrene oxide
17 31.094 0.93 117 C5H11NO2 Amyl nitrite
of the agar plates. Plant extract (10 mg/mL) was added on the discs
18 31.841 2.66 83 C5H9N Aziridine
at various concentrations (300 and 500 mg/mL). Disc containing 19 31.941 1.27 165 C6H18B3N3 Borazine
standard concentrations of the antibiotic Kanamycin (30 mcg/disc) 20 32.944 0.54 88 C5H12O 1-Butanol
was used as positive control. The agar plates were incubated for 21 35.076 34.68 298 C19H38O2 Nonadecanoic acid
24 h at 37 C, and the inhibition zones were measured in millimeter 22 38.779 3.45 83 C5H9N 1-Propenyl-aziridine

in diameter. (continued on next page)

110 D. Arul Ananth et al. / Free Radicals and Antioxidants 3 (2013) 107e112

Table 2 (continued ) anti carcinogenic, antioxidant, chemopreventive activities and

Peak R.Ta %b MWc MFd Compound name antiviral antidiabetic activities.19 In addition, 10-undecenoic acid
has effective fungicidal activity against Candida albicans, thus helps
23 41.484 22.12 194 C8H10N4O2 Caffeine
24 42.415 10.86 254 C16H30O2 Cyclopentaneundecanoic acid
achieve a healthy balance of normal intestinal and vaginal flora.20
25 44.672 10.96 182 C11H18O2 10-Undecynoic acid Phenolic compounds were considered to be the major contrib-
a utors to the antioxidant capacity of the plants. The total phenolics
R.T e retention time.
b
Area % content of the C. urens methanolic extract was found to be
c
MW e molecular weight. 10.23 0.40, 15.00 0.40 and 17.63 0.51 mg of GAE/g in the fruit
d
MF e molecular formula. skin, leaf and immature fruit respectively (Table 1). The highest
amount of phenolic content was found in immature fruit
(17.63 0.51 mg GAE/g) while the lowest was in fruit skin
3. Results and discussion (10.23 0.40 mg GAE/g). On the other hand, the amount of flavo-
noids was found to be higher in leaf (15.35 0.41 mg RE/g) when
The chemical compounds of methanol extract of C. urens were compared to immature fruit (11.29 0.54 mg RE/g) and fruit skin
analyzed by GCeMS method and they were represented in (13.58 0.40 mg RE/g) respectively. The phenolics and flavonoids
(Table 2aec). By comparing the mass spectra of the plant extract naturally originate in medicinal plant extracts and have been re-
with the WILEY8.LIB. library, 23 compounds were identified in ported to have major biological activities such as antioxidant and
methanolic extract of C. urens leaf, 18 compounds in immature fruit antimicrobial properties.21 A highly positive relationship between
and 25 compounds in fruit skin extract. Of the 66 compounds total phenolics and antioxidant activity appears to be the trend in
identified, the most prevailing compounds were stearic acid many aromatic and medicinal plant species with reference to Oktay
(octadeconoic acid) (28.51%) 10-undecenoic acid (12.86%), 2E,6E- et al22 Phenolic compounds of medicinal as well as aromatic plants
farnesol (20.01%), hendecynoic acid (18.09%) and caffeine (22.12%). might be responsible to cure some inflammatory disease, like
Previous reports suggest that the similar compounds were also rheumatoid arthritis and nephrotoxicity.23,24
present in date palm leaf extracts.18 Catechins and 10-undecenoic Fig. 2a shows the dose response curve of DPPH radical scav-
acid have been reported to have an anti microbial effect, as well as enging activity of the methanol extracts of C. urens compared with

Fig. 2. Determination of antioxidant and reducing power activity of C. urens methanol extracts. (a) DPPH radical scavenging activity, (b) ABTS radical scavenging activity, (c) Nitric
oxide scavenging activity, (d) Reducing power activity.
D. Arul Ananth et al. / Free Radicals and Antioxidants 3 (2013) 107e112 111

Fig. 3. Antimicrobial activity of C. urens methanol extracts. Zone of inhibition (mm).

BHT. The free radical DPPH possesses a characteristic absorption at effective in the treatment of infectious diseases with less or no side
517 nm, which decreases significantly on exposure to plant extract effects which are often associated with synthetic antibiotics.27 The
by providing hydrogen atom or electron donation.25 It was terpene alcohols damage the cell membranes of E. coli, S. aureus,
observed that the leaf showed higher activity than that of the and Listeria monocytogenes, resulting in leakage of potassium ions
immature fruit and fruit skin extract. The percentage of inhibition from cells, which cause death of the organism. Recent reports
of DPPH radicals by methanol extract of the leaves reached up to suggest that the sesquiterpene alcohol like farnesol has been
88.27% at the concentration of 100 mg/mL, where as the immature confirmed to reduce the growth of S. aureus and Streptococcus
fruit and fruit skin showed 66.19% and 62.67% at the same con- mutans.28,29 From these results, we have identified the major
centration respectively. Although the DPPH and ABTS radical antimicrobial compounds such as 10-undecenoic acid, caffeine and
scavenging are based on the same principle, the data obtained from 2E,6E-farnesol which may have many pharmacological activities
DPPH are lower than those obtained from the ABTS activity. Inter- and the results were supported by Zhonghui et al30 More over, it is
estingly, the inhibition percentage of ABTS radicals by immature also reported that compounds in lower quantities might be
fruit was found to be higher (96.12%) than the standard reference involved in some type of synergism with the active compound
BHT (87.74%), leaf (48%) and fruit skin (76.45%) at the concentration which might be the reason behind the high activity of antioxidant
of 25 mg/mL (Fig. 2b.). Reducing power assay revealed that assayed and antimicrobial in immature fruits when compared to the leaves
plant samples were able to reduce the ferric ions (Fe3þ) to ferrous and fruit skin of C. urens.
ions (Fe2þ) in concentration dependent manner.23 The leaf and
immature fruit methanol extracts shows moderate reducing power
4. Conclusion
capacity when compared to that of fruit skin and comparable with
that of the standard BHT Fig. 2d. Nitric oxide scavenging ability
The present work clearly demonstrated the antioxidant po-
assay revealed that all the extracts of different plant parts exhibited
tential and antimicrobial activity of C. urens. The GCeMS analysis
scavenging potential. Immature fruit showed better activity than
of methanolic extract of C. urens reveals the presence of major
leaf and fruit skin (Fig. 2c). At the concentration of 500 mg/mL, the
bioactive compounds such as phenolics, fatty acids, carboxylic
methanol extract of immature fruit exhibited 62.77% nitric oxide
acids, terpenoids and caffeine. The observed strong antioxidant
scavenging ability while comparing to that of leaves and fruit skin
and antimicrobial activity confirms the effectiveness of traditional
(52.59% and 60.74%) respectively.
use of this herbal drug against microbes which act as source of
Previous reports suggest that phenolic and flavonoid com-
natural antioxidant with potential use in pharmaceutical industry.
pounds (gallic acid, caffeic acid, p-coumaric acid, quercetin, rutin
Antioxidants are reported to possess antimicrobial activity. Hence,
and catechin) in plants possess strong antioxidant activity that
we suggest that antimicrobial activity exhibited by the extract
might contribute to antimicrobial potential.26 The disc diffusion
might be due to the presence of antioxidants. However, isolation
method was employed for the determination of antimicrobial ac-
of individual phytochemical constituents and subjecting it to the
tivity of plant extracts against human pathogens. The zone of in-
biological activity is in progress which will definitely give fruitful
hibition of the plant extract was found to be in the range from 7 to
results.
18 mm (Fig. 3) against the entire tested microorganisms. Meth-
anolic extract of fruit skin of C. urens showed maximum activity of
about 18 mm against E. coli and immature fruit showed about Conflicts of interest
16 mm diameter zone against V. cholerae. Plant based antibiotic
drugs have enormous therapeutic potential and have been proven All authors have none to declare.
112 D. Arul Ananth et al. / Free Radicals and Antioxidants 3 (2013) 107e112

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Kumar, Senior Technical Assistant, AIRF, JNU, New Delhi, for Trop Biomed; 2012:S895eS900.
18. Azmat S, Ifzal R, Rasheed M, Mohammad FV, Ahmad VV. GCeMS analysis of n-
excellent technical GCeMS support in these studies. hexane extract from seeds and leaves of Phoenix dactylifera L. J Chem Soc Pak.
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19. Bourne N, Ireland J, Stanberry LR, Bernstein DI. Effect of undecylenic acid as a
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