Arabian Journal of Chemistry (2014)

xxx, xxxxxx

King Saud University

Arabian Journal ofChemistry

www.ksu.edu.sa
www.sciencedirect.com

ORIGINAL ARTICLE

Extraction,isolationandidenticationofavonoid
fromEuphorbia neriifolia
leaves
* , Pracheta Janmeda
Veena Sharma
Department of Bioscience and Biotechnology, Banasthali University, 304022 Banasthali, Rajasthan, India
Received 13 December 2012; accepted 20 August 2014

KEYWORDS
;
Euphorbia neriifolia
Flavonoids;
Chromatography

in
leaves were extracted, identied and
neriifolia
Abstract The avonoids contained Euphorbia
characterized.Directandsequentialsoxhletextractionanditsconcentratedfractionsweresubjected
to thin layer chromatography and high performance thin layer chromatography. The results
showed that maximum yield of the avonoid (6.53g) was obtained from ethanolic extract. The
Rf value of isolated avonoid and phytochemical screening has been compared with standard
1
Quercetin.CharacterizationosolatedavonoidwasdonebyIR, HNMR,andMS.Onthebasis
ofchemical and spectral analysis structure was elucidated as2-(3,4-dihydroxy-5-methoxy-phenyl)3,5-dihydroxy-6,7-dimethoxychromen-4-one, aavonoid.Thiscompoundwasisolatedfortherst
time from this plant.
2014Production and hosting by Elsevier B.V. on behalf of King Saud University.

for human health (Raskin et al., 2002; Reddy et al., 2003).

Compounds belonging to the terpenoids, alkaloids and avonoidsarecurrentlyusedasdrugsortopreventvariousdiseases
Phytochemistryreportsthousandsofnewerorganicmolecules
(Raskin et al., 2002) and in particular some of these comorcompoundseveryyear.Pharmacologicaltesting,modifying,
pounds seem to be efcient in preventing and inhibiting variderivatizingandresearchonthesenaturalproductsrepresenta
major strategy for discovering and developing new drugsous types of cancer (Reddy et al., 2003).
Flavonoidsareagroupofabout4000naturallypolypheno(Kayser et al., 2000). Moreover, plant secondary metabolites
liccompounds,founduniversallyinplantorigin.Accordingto
present chemical and pharmaceutical properties interesting
thedifferencesinfunctionalgroupsandtheirrelativepositions
of the 15-carbon skeleton (aglycons), avonoids are classied
* Correspondingauthorat:Lab-209,DepartmentofBioscienceand
into several subgroups including the following: avone, avaBiotechnology, Banasthali University, P.O. Banasthali, Distt.: Tonk
none, avonol, isoavonoid, anthocyanidin, and chalcones
304022, India. Tel.: +91 1438228386, +91 9352381260.
(Harborne, 1998).
E-mail addresses: drvshs@gmail.com (V. Sharma), pracheta25@
The plant Euphorbia neriifolia
, especially the leaves, has
gmail.com (P. Janmeda).
been reported to possess a wide range of medicinal properties
Peer review under responsibility of King Saud University.
(Ilyas et al., 1998; Janmeda et al., 2011; Pracheta et al., 2011;
Sharma etal., 2011a,b, 2012a,b), which has prompted acomprehensiveinvestigationoeavesof
. Anumberof
E. neriifolia
Production and hosting by Elsevier
compoundshavealreadybeenisolated(Chatterjeeetal.,1978;
1. Introduction

http://dx.doi.org/10.1016/j.arabjc.2014.08.019
2014Production and hosting by Elsevier B.V. on behalf of King Saud University.
1878-5352
Pleasecitethisarticleinpressas:Sharma,V.,Janmeda,P.Extraction, isolationandidenticationofavonoidfrom
Euphorbianeriifolia
leaves.ArabianJournalof
Chemistry (2014), http://dx.doi.org/10.1016/j.arabjc.2014.08.019

V. Sharma, P. Janmeda

Ng, 1990;Ilyas et al.,1998; Yadav etal., 2011)but this is the

brown bands that were produced after keeping the plates in
rst report to isolate avonoid from
E. neriifolialeaves. The iodine chamber were scratched and suspended in the mobile
purposeofthisstudywastoisolatethemostimportantgroup phase separately for 34days. After that mobile phase was
ofphytochemical classi.e.avonoids usingTLCandHPTLC sucked out, vacuum evaporated and the residue left was colastechniqueandwascharacterizedthroughtheirspectral(IR,lectedtillsufcientamountfordosingandspectrophotometric
1
H NMR and MS), as well as comparison with a reference analysiswasobtained.Theselectedpuriedmaterialwassubmaterials.
jected to its HPTLC and IR spectral.
2. Experimental

2.5.Phytochemical screening of the isolated compound

2.1.Chemicals and reagents

Chemical tests as described by Harborne (1998) were carried

out on the isolated compound using standard procedures.

Allchemicalsandreagentsusedinthestudywereofanalytical
2.6.HPTLC method for the estimation of avonoids
grade and were purchased from reliable rms and institutes
[Sd-ne chemicals, SIGMA, SRL (India), MERCK, RANBAXY, and SUYOG]. Silica gel (G) 60F and 0.25 readymadeThe complete CAMAG TLC equipment consists of a fully
aluminum sheets (Merck KGaA, Germany). Silica gel 60 automatic sample Linomat Vsample applicator, adeveloping
chamber.Finally,aCamagTLCscannerisavailableallowing
20cm, Merck KGaA,
F254, HPTLC aluminium sheets 20
densitometricevaluationofchromatogramsandCATS4softGermany Ord. No. 1.05554.
wareforinterpretationofdata.About10mgoftheextractsof
theENwastakenanddissolvedinrespectivesolventsandthe
2.2.Procurement, authentication of plant material
volumewasmadeupto10mlinastandardask(1000
l g/ml).
Standard (10mg) was taken and dissolved in methanol. This
E. neriifolia(EN)leaveswerecollectedfrommedicinalgarden wastransferredintoastandardaskandthevolumewasmade
of the Banasthali University, Banasthali and nearby areasupto100mltoprepare100l
of
g/mlsolution.Silicagel60F254
00
Banasthali, Rajasthan, India (Latitude N2624014.8414
;
and
HPTLC aluminium sheets were used as adsorbent (sta0
00
Longitude E73529.7194), in the month of October, 2009 tionary phase). The extracts were applied point-wise from
and were taxonomically identied by Botanist of Krishi Vig1000l g/ml sample solution, l10
l of the sample was applied
yan Kendra, Banasthali University, Banasthali, Rajasthan,on HPTLC aluminium sheets as different tracks in the form
India. A voucher specimen was deposited in the herbarium
of6mmwidebandsbyusingaCamagsemi-automaticLinomof Department of Bioscience and Biotechnology, Banasthali
at5spotteratadistanceof12mm.NitrogengaswasalsosupUniversity (No. BVH780141A).
pliedforsimultaneousdryingofbandsandthenusingdrierfor
completely drying of bands. HPTLC of different extracts was
2.3.Extraction
performed by using the mobile phase n-butanol: acetic acid:
water (2:2:6). To saturate the chamber, 10ml mobile phase
Shade dried leaves were powdered (250g), soxhlet extracted
was placed in each at-bottomed Camag twin trough TLC
with 70% (v/v) ethanol and vacuum concentrated to dryness
chamber, 30min before the development of the PTLC plate.
under reduced pressure at60
1 C. After drying in hot air Thechamberwassealedwithparalmandcoveredwithasteel
oven (4045C), it was stored in an air tight container in lid.Thedevelopedplateswerethendriedandscannedusinga
refrigerator at 5C. The residue was designated as hydro- TLCscanner 3with Wincats software under364nm(Wagner
ethanolic extract E.
of neriifolia(HEEN).
and Bladt, 1996). All plates were visualized directly after dryDried leaves of
E. neriifolia(250g) were extracted succes-ing and a ngerprint prole was photo documented using a
sively with pet-ether, benzene, chloroform, ethyl acetate,Camag
and Reproster 3 under 254nm and 366nm in UV and
ethanol and nally macerated with distilled water (non-polar
visible light. The digital images of the chromatograms were
to polar) to get respective extracts. Flavonoid contents and
evaluatedwiththeprogrammeCAMAGVideoScan.Thecaptheir presence were determined by the method of Harborne
tured image was subjected to a visual inspection on the com(1998), using quercetin as a standard. The extracts were puter
ana- screen. The differences found, are specied by the
lysed by means of TLC.
HPTLC system in which the difference is detected and by
theRf value (and colour) of acompound in the system.
2.4.Thin layer chromatography (TLC)
2.7.Compound characterization
Thin layer chromatography was performed using standard
methods (Harborne, 1998). Small quantities of samples For characterization of compound IR, NMR and Mass
(2mg/ml)weredissolvedintheirrespectivesolvents.Quercetin
spectra were performed. IR was obtained for the isolated
(1mg) standard was dissolved in methanol. Different mobile
avonoid. The sample (12mg) was crushed in KBr
phases with varying concentrations were employed in the(34mg) pellets using a FTIR (Fourier transform Infrared
screeningprogrammeandselectedtheoneinwhichseparation
spectroscopy; Model - Varian 3600) with the help of mechanofavonoidwasclear:n-butanol:aceticacid:water(2:2:6).Allical pressure. They were recorded within the wavenumber
1
1
plateswerevisualizeddirectlyafterdryingandwiththehelpof range 4000400cm in an FTIR instrument. H NMR
UVat254nmand366nminUVTLCviewer.The Rf valueof
spectra was recorded on DRX-Bruker 300MHz (Mega Hz),
thedifferentspotsthatwereobservedwascalculated.Thedark
Switzerland. Nuclear magnetic eld was obtained for the

Pleasecitethisarticle inpressas:Sharma,V.,Janmeda,P.Extraction, isolationandidenticationofavonoid Euphorbianeriifolia

from
leaves.ArabianJournalof
Chemistry (2014), http://dx.doi.org/10.1016/j.arabjc.2014.08.019

Extraction, isolation and identication of avonoidEuphorbia

from
neriifolia
leaves

isolatedavonoid.IsolatedcompoundwasdissolvedinrespecTable 1 Percentage yield of compounds isolated from 500g

tivesolventCDCl3 andabout600l lwaspouredinNMRtube
ethanolic extract E.
of neriifolia
.
andobservedontheappliedmagneticeld.Masswasobtained
IC
Yield of IC (g)
% yield of IC
Rf Value
by TOF MS ES+5.18e4, TOF MS ES+477 and TOF MS
ES+174.80ES+3 (ABHAY_BIOTECH 28).
IF 1
0.60
2.121
0.424
3. Results and discussion

IF 2
IF 3

0.79
0.90

6.532
5.263

1.306
1.052

IC: Isolated compounds.

Chromatographic methods (TLC & HPTLC) for detection of

avonoids fromE. neriifolia
, have not been reported in the
ethanol extract which coincides with
value of standard
Rfthe
literature.
quercetin. 2F carefully crystallized with ethanol, gives solid
pale yellow crystal, soluble in water and in organic solvents
3.1.Chromatographic separation
and was designed as
E. neriifoliaisolated avonoid (ENF).
ENFcompoundwasselectedforfurtherstudywhichincludes
Among all, the yield of ethanol (48.9g) and aqueous (89.5g)
repeated TLC, identifying the nature of compound by perextractwasfoundinexcesscomparedtoall(Fig.1).Available
forming several qualitative tests, conrmation by HPTLC
allsevenextracts,ethanolextractcontainedbulkofavonoids
and IR of this compound. Meena and Patni (2008) adopted
and dark brown sticky semi solid ethanol extract (48.9g) was
same procedure for the isolation & identication of avonoid
used for chromatographic separation using quercetin as stanquercetin from
Citrullus colocynthis.
(See Fig. 2)
dard.Initially,varioussolventphaseswithvaryingratioswere
tried (Sharma and Janmeda, 2013a), for all fractions
E.of
3.2.Phytochemical screening of the isolated compound (ENF)
neriifolia
. Out of all the n-butanol: acetic acid: water (BAW,
2: 2: 6) was found to be the most appropriate solvent system
forseparationofavonoidsfromethanolextractofEN.After The results of various qualitative tests performed in the laboratory are outlined in Table 2. The presence of avonoids
TLC three spots resolved that were nomenclatured
1
2 as F ,F
and F3 haveRf values of 0.60, 0.79 and 0.90 respectively(ENF) was conrmed by screening tests, which illustrated a
(Fig1).Percentageyieldofcompoundsisolatedfromethanolicpositive test for avonoids and negative for steroids, terpeextract of EN is depicted in Table 1. Maximum yield was noids and alkaloids.
obtained in F2 fraction (0.65g). The standard
Rf value of
3.3.HPTLC ngerprinting prole
kaempferol was greater than quercetin and rutin, thus suspectedthattheF3 (0.90)compoundwasrelatedtokaempferol
and F1coincides with rutin. When the developed plates were
Authentic marker of avonol (quercetin) obtained commersprayedwithammoniaandiodinevapours,itshoweddeepyel-cially was co-chromatographed.
HPTLC chromatogram
lowcolourofquercetin.Rf value(0.79)ofF2 isolatedfromthe showed that a maximum number of components were

.
neriifolia
Figure 1 Schematic diagram for the isolation of avonoidsE.from

Pleasecitethisarticleinpressas:Sharma,V.,Janmeda,P.Extraction, isolationandidenticationofavonoidfrom
Euphorbianeriifolia
leaves.ArabianJournalof
Chemistry (2014), http://dx.doi.org/10.1016/j.arabjc.2014.08.019

V. Sharma, P. Janmeda

HPTLC
baseline display of ethyl acetate, ethanol, aqueous extract and isolated avonoid (ENF) compared with quercetin.
Figure
2

observed under UV and orescence absorbance mode. Fig. 2

Table 2 Analysis of phytochemicals in compound isolated conrmed the results obtained by TLC, in which the chromatogram spectral clearly showedRthat
from ethanolic extractE.
ofneriifolialeaves and standard.
f values of all menS. no.

Phytochemicals

ENF

Standard (quercetin)

1
2
3
4
5

Phenols
Steroids
Alkaloids
Flavonoids
Terpenoids

++

+++

++

+++

tioned extracts and isolated compound (ENF) coincided with

thatofstandardquercetin.Theresultsaresupportedbyprevious reports (Lakshmi et al., 2012; Sharma and Janmeda,
2013a; Sharma and Pracheta, 2013a). Putative therapeutic
effects of many traditional medicines might be ascribed to
the presence of avonoids (Schultz et al., 2008). The presence
of anti-carcinogenic (Janmeda et al., 2011; Sharma et al.,
2011b; Sharma et al., 2012b) and antioxidative (Pracheta

Figure 3 Mass spectrum of isolated compound.

Pleasecitethisarticle inpressas:Sharma,V.,Janmeda,P.Extraction, isolationandidenticationofavonoid Euphorbianeriifolia

from
leaves.ArabianJournalof
Chemistry (2014), http://dx.doi.org/10.1016/j.arabjc.2014.08.019

Extraction, isolation and identication of avonoidEuphorbia

from
neriifolia
leaves

etal.,2011)propertiesofextractof
Euphorbianeriifolia
leaves
can be attributed due to the presence of avonoids.
3.4.Identication and Spectral analysis of isolated avonoid
Pale yellow needles were obtained after purication: m.p.
191193C, Rf: 0.79 (BAW). IR spectroscopy provides a
ngerprintofthedrugthroughwhichwecanidentifythenatureofbondingandtypesoffunctionalgroupsinthesamples.
All values of IR and NMR were in the decreasing order. IR
spectrum of ENF in KBr pellet exhibits peaks at 3624, 3473,
Figure 4 Structure of avonoid 2-(3,4-dihydroxy-5-methoxy1
1
1
3286cm
(OH), 1707cm
(>C O), 1649cm ,
phenyl)-3,5-dihydroxy-6,7-dimethoxychromen-4-one
18 18 (C
9 H O ).
1
1408cm 1 (CA C C), 1275, 1245, 1045cm
(OCH3), and
1
769.8cm (CA H). The peaks revealed the number of functional groups that have a great signicant towards medicinal
methods (Kiralj and Ferreira, 2009) and it helps to precisely
prospects of
.
E. neriifolia
1
predict the biological activities of newly designed analogues
The H NMR spectrum of ENF was taken as 300MHz
(de Melo et al., 2010). Successful prediction of anti-HIV
operatingfrequencyinCDCl
3 andspectrumofENFdisplayed
(Alves et al., 2001) and anti-tumour activities (Moriani et al.,
signals corresponding to a tri-substitutedb-ring of the
2002
) of avonoid compounds has been reported. According
avonoidnucleusat
d ppm:8.04(9H,s,OCH 3),7.27(3H,s,
tothesestudies,theantioxidantactivityofavonoidsdepends
ArH),6.73(4H,s,OH),and2.892.97(2H,d,Non-ArH).
1
stronglyonthenumberandpositionofhydroxylgroupsinthe
The H NMR spectrum of the extracted compound revealed
the signals of aromatic protons, which are close to those molecule. In the present ndings dihydroxylated B-ring (catechol structure), presence of hydroxyl and methoxy functional
reported for Quercetin moiety (Harborne and Mabry, 1982;
groups and in the C-ring presence of the hydroxyl group are
Agrawal and Bansal, 1989). Therefore, isolated compound
also presumed to increase the antioxidant capacity. Presence
ENF could be quercetin related avonoid which is not previofthehydroxylgroupon3,5,3 0and4 0isdepictedtoenhance
ouslyreportedinthetitledplant.
The molecular weight of the extracted compound was the antioxidant activity of isolated avonoid.
observedby TOFMS ES+ m/z 378.33 calculatedfor
C18
HO
378) as depicted in Fig. 3. The molecular ion 4. Conclusion
18(m/z
9
peak with base peak due to the most stable molecular ion
was observedat 240.25 calculatedfor C15
HO
12 3 (m/z
Concluding the aforementioned studies it was analysed that
240).The base ion peaks correspond to basic moiety of avothe studied plant contained avonoids. Isolated avonoid 2nol. The main component of the extract was characterized
as
(3,4-dihydroxy-5-methoxy-phenyl)-3,5-dihydroxy-6,7-dimeth2-(3,4-dihydroxy-5-methoxy-phenyl)-3,5-dihydroxy-6,7- oxychromen-4-one
(C18
HO
extractedfrom Euphorbia
18) 9
dimethoxychromen-4-one and designed as E.
ENF
neriifolia
(
neriifoliaposses signicant potential to scavenge free radicals,
avonoid) a avonoid by employing mass spectrometry as
ROS and also inhibits lipid peroxidation and hence have got
depicted in Fig. 4.
anticarcinogenicpotential.Thepresenceofhighconcentration
We have already seen the anticarcinogenic activity of this
ofavonoidsinEuphorbianeriifolia
whichisdepictedfromour
novelavonoidinmiceanditwasnoticedthattheisolateda- results,areresponsibleforimpartingtheantioxidativemechavonoid was able to protect the tissue architecture and was
nism that inturns are the causitive factors of various degenercapable of minimizing the abnormalities and carcinogenicity
ative diseases.
caused by N-nitrosodiethylamine (Sharma and Janmeda,
2013b; 2014). This might be due to ROS radical inhibition &
Contributors
neutralizingthefreeradicalswhichprovidesscienticevidence
ofethno-medicinaltherapeuticuseofENFfortreatingcancer.
IR spectra of isolated avonoid conrmed the presenceBoth
of authors have materially participated in the research
theOHgroupinfreeandbindingstateswhichactsasbinding and/or article preparation. Veena Sharma helped in designing
site of enzymes due to which isolated avonoid exhibitedthe experiment and in writing the article. Pracheta Janmeda
the experimental work.
anti-carcinogenic activity to the best extent by retarding performed
and
modulating the phase I enzymes (cytochrome P450 and b5)
peroxidation level, biochemical enzymes (catalase, superoxide
Acknowledgements
dismutase,aspartatetransaminase,alaninetransaminase,alkalinephosphates,totalproteinandtotalcholesterol)alteredbyThe authors are grateful to the CDRI, Lucknow for their
1
N-nitrosodiethylamine (Sharma and Janmeda 2013b; 2014;
help in providing the IR,
H NMR and mass spectra. One of
Sharma and Pracheta, 2013b).
the authors (P. Janmeda) is grateful to the University Grants
Quantitative structureactivity relationship (QSAR) is an
Commission (UGC) for providing nancial assistance (Grant
accepted means for establishing quantitative relationship/F. No. 37-68/2009; SR) and authorities of the Banasthali
betweenbiological activity and descriptorsrepresenting University, Rajasthan for providing the rest of necessary
physicochemical properties of thecompounds using statistical
facilities.

Pleasecitethisarticleinpressas:Sharma,V.,Janmeda,P.Extraction, isolationandidenticationofavonoidfrom
Euphorbianeriifolia
leaves.ArabianJournalof
Chemistry (2014), http://dx.doi.org/10.1016/j.arabjc.2014.08.019

V. Sharma, P. Janmeda

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Euphorbia neriifolia

Pleasecitethisarticle inpressas:Sharma,V.,Janmeda,P.Extraction, isolationandidenticationofavonoid Euphorbianeriifolia

from
leaves.ArabianJournalof
Chemistry (2014), http://dx.doi.org/10.1016/j.arabjc.2014.08.019