Sei sulla pagina 1di 9

Available online at http://www.urpjournals.

com

International Journal of Agricultural and Food Science


Universal Research Publications. All rights reserved

ISSN 2249-8516
Original Article
ISOLATION AND SEPARATION OF PHENOLIC COMPOUND FROM
CORIANDER FLOWERS
Dr. P. Nazni* and R. Dharmaligam
Department of Food science and Nutrition, Periyar University, Salem, Tamilnadu, India.
raiseandrich@gmail.com
*
Corresponding author: naznifsn@gamil.com
Received 16 January 2014; accepted 21 January 2014
Abstract
The present study is carried out with coriander flowers; A simple and fast method was developed for simultaneous
quantitative determination of three biologically active phenolic compounds such as apigenin, quercetin, keamphferol in
flowers of Coriandrum sativum separation using by flash column chromatography then purification were conducted by
preparative chromatography and HPLC. The phenolic compound determine with different spectroscopic method such as
LC-MS, HC NMR, FTIR and Melting point. The present method is being reported first time and may be used for routine
quality control of the flowers of Coriandrum sativum.
2014 Universal Research Publications. All rights reserved
Key words: Apigenin, Quercetin, Keamphferol, Chromatography.
effects as well as their potential estrogenic and anticancer
Introduction
Extracts of aromatic herbs, spices, and medicinal plants are activities (Springob and Saito, 2002). Quercetin belongs to
used in food and pharmaceutical processing to impart this group of plant pigments called flavonoids that are
flavor or other functional properties, as well as ingredients largely responsible for the colours of many fruits, flowers
in the pharmaceutical products. Plant based natural and vegetables. Quercetin works as anti-inflammatory,
constituents can be derived from any part of the plant like
antioxidant, anticancer agents. (Lamson and Brignale
bark, leaves, flowers, roots, fruits, seeds, etc (Gordon and (2000) and Mahesh Chand Meena and Vidya Patni 2008).
David, 2001) i.e. any part of the plant may contain active Flavonoids possess a variety of biological activities that are
components. The beneficial medicinal effects of plant thought to contribute towards protecting humans against
materials typically result from the combinations of degenerative diseases. Quercetin, kaempferol and
secondary products present in the plant. The medicinal isorhamnetin have been shown to have an antiactions of plants are unique to particular plant species or inflammatory effect on activated macrophages. In addition,
groups and are consistent with this concept as the quercetin and kaempferol show chemopreventive properties
combination of secondary products in a particular plant is in brain tumours (medulloblastoma) and synergistically
taxonomically distinct (Wink, 1999). They are usually suppress cell proliferation in human gut cancer lines.
subdivided according to their substituents into flavanols Quercetin a main aglycone in human nutrition is a potent
(kaempferol, quercetin), anthocyanins, flavones, flavonones free radical scavenger and antioxidant, which is why it is
and chalcones. These flavonoids display a remarkable array thought to protect humans against several types of cancer
of biochemical and pharmacological actions viz.,anti - and cardiovascular diseases. Antioxidant effects of
inflammatory, antioxidant, anti -allergic, hepatoprotective, quercetin on the mucosa of the nasal turbinate were
antithrombotic, antiviral and anticarcinogenic activities demonstrated. Higher intakes of kaempferol resulted in a
(Middleton and Kandaswami, 1993). These compounds lower risk of coronary heart disease. In addition,
appear to play vital roles in defence against pathogens and isorhamnetin revealed distinct vasodilatory effects in
predators and contribute to physiological functions such as animal models, suggesting vascular protective effects in
seed maturation and dormancy (Winkel-Shirley, 2002). human cardiovascular diseases. (Susanne Schmidt1,
They are synthesized from phenyl propanoid and acetate Michaela Zietz).
derived precursors. Flavonoids are important for human Flavonoids are polyphenolic compounds that occur
beings due to their antioxidative and radical scavenging ubiquitously in plant foods. Flavonols and flavones are
International Journal of Agricultural and Food Science 2014, 4(1): 13-21

13

subclasses of flavonoids (Khnau J 1976, Markham KR


1989, Herrmann K 1988, and 1979). In 1992 the average
daily intake of the flavonols quercetin, kaempferol, and
myricetin from the Dutch diet was 16, 4, and 1 mg,
respectively; the average intake of the flavones apigenin
and luteolin was 1 mg each (. Hertog MGL et al 1993). The
intake of these five dietary flavonoids was associated with
a reduced risk for ischemic heart disease and stroke in
several (Keli SO et al 1996, Knekt P et al 1996 Hertog
MGL, 1995-93,) although not all (Rimm ER, et al 1996,
Hertog MGL, et al 1997 ), epidemiologic studies. Two
types of mechanisms have been proposed to explain this
protective effect: inhibition of LDL oxidation and
inhibition of platelet aggregation (Hertog MGL and
Hollman PCH et al 1996). Results obtained by incubation
of human platelets or animal cells with isolated isolated
flavonoids suggest that flavonoids inhibit platelet
aggregation probably by inhibition of cyclooxygenase
activity (P Mensink1997).
In addition, many studies have demonstrated the potential
of plant products as antioxidants against various diseases
induced by free radicals (Hou et al., 2003), and it has been
determined that the antioxidant effect of plants is mainly
attributed to phenolic compounds, such as flavonoids,
phenolic acids, tannins, and phenolic diterpenes (Pietta,
2000). The aim of the present study is to deals with the
isolation and identification of flavonoid "quercetin"
keamphferol and apigenin from coriander flower.
Materials and Methods
Plant materials
The plant materials of C. sativum were collected from the
plants grown in and around Salem district, Tamilnadu,
India. The plant materials were dried in shade separately.
Reagents
Reagents and chemicals Methanol and acetic acid were of
HPLC grade and were purchased from Merck Company.
Deionized water was prepared by a Milli-Q Water
Purification system.
Extraction and separation of crude sample
The dried samples (flower 250 g) were chopped into small
pieces and extracted with methanol: water (80:20) by
soaking for 48 Hrs at room temperature (25C). The
methanolic extract was decanted, filtered under vacuum,
concentrated in a rotary evaporator (40C.). The resulting
crude extract from the flower of CF (25.0g) was
fractionated successively with ethyl acetate (EtOAc), nbutanol (BuOH), and the yield of soluble fractions of
EtOAc (2.0g), BuOH (1.0g), and water (20.g). (Janmejai K
Srivastava et. al 2009, Tereschuk et.al. Naira Nayeem and
Karvekar MD 2010). The ethyl acetate (methanol) soluble
fraction from flower of CF (2.0g) was loaded into a flash
chromatography column (silica gel for mesh 260-400
revelries grace column silisep) and eluted with different
solvent system for gradient programme (like, EtOAc/nhexane and MeOH/chloroform solvent systems). For this
separation were separated by 5 sub fractions (EA5 EA10
and methanol: chloroform 7-10). Frequently each fraction
was checked with TLC. S. (OREVI, M. CAKI, S.
AMR 2001, hui-ling cheng et al 2013 and jolanta nazaruk
and jan gudej 2001) for different mobile phase to getting

14

single spot using by iodine vapour (solvent system for


t1and t2 chloroform: methanol; acetic acid; water 95:5;5:2
and t3).
Analysis of Crude Extract by HPLC
The resultant flavonoid aglycons were qualified by using
reversed-phase HPLC series 6330 from Agilent
technologies. Solvent A consisted of 100% water and 0.5%
acetic acid; solvent B was 100% acetonitrile. The following
gradient was used for eluent B: 57% (012 min), 79%
(1225 min), 9 12% (2545 min), 1215% (45100 min),
15% isocratic (100 150 min), 1550% (150155 min),
50% isocratic (155165 min), 505% (165170 min), 5%
isocratic (170175 min) ( Susanne Schmidt et.al 2010). The
flow rate used was 0.8mL/min, and the measured detector
wavelengths were set at 280, 320, 330, 340 and 370 nm.
Purification of phenolic compound by using Pre-HPLC
The fraction sample collected from chloroform methonal
solvent system, collected sample purified through semi
preparative HPLC (using a PU-2080 pump (Jasco, Japan)
equipped with a MD-2010 multi wave length detector
(Jasco, Japan) and a 250 -10.0 mm i.d., 4- lm Synergi
Polar-RP column (Phenomenex, Torrance, CA). The
mobile phase was solvent A, 100% ACN; and solvent B,
ultrapure water. Elution condition was 080 min of 20
100% AB (linear gradient) at a flow rate of 4 ml/min
(Shang-Tse Ho et.al., 2010).
The structures of compounds were identified by LC-MS
(Agilent 6330 Ion Trap ),FT-IR and NMR (Varian Unity
Inova-600, USA), and all spectral data were consistent with
the literature (Baderschneider & Winterhalter, 2001; Jiang
et al., 2001; Villegas & Kojima, 1985; Yoshida, Ahmed,
Memon, Okusa, 1991& Shang-Tse Ho et.al., 2010, Nedime
Durust et .al 1999 and).
Purified CF flower extract samples were subjected to LCMS and NMR for the structural elucidation and
identification of constituents were performed, three
compounds were separated at different retention time.
Moreover the particular compounds were determined by
FTIR and DSC.
Result and discussion
The fresh flower harvested to under our study director
guidelines and dried with room temperature. The dried
material soaking with methanol: water (80:20) for 24hrs.
After completion of soaking filter to whattmen paper and
concentrated by rotary vapor at 40c. The crude sample
subject to inject HPLC and separated to all peak using
different gradient programmed based on that separation to
developed for column chromatography method.
The methanolic extract was subjected to column
chromatography on silica gel using solvents of increasing
polarities starting from petroleum ether, chloroform, ethyl
acetate and methanol in different ratios to yield several
Sub-fractions. Fractions 10-20 (40% chloroform in
methanol) were mixed due to their similar TLC pattern this
fraction was coded as T1corander flower. The solvent
system methanol: acetic acid: water in the ratio 95:5:5. This
fraction compound 1 was eluted with chloroform and
methanol in different ratios to get fractions of 20ml
.Fraction 5 showed a single spot. This fraction was
collected dried and was recrystallized using methanol to get

International Journal of Agricultural and Food Science 2014, 4(1): 13-21

0.20mg of compound 1 which was identified as keampferol


(Jolanta Nazaruk and Jan gudej 2001).
Compound 2 was isolated from fractions 89-93 (10%
methanol in ethyl acetate) and subjected to TLC using the
solvent system methanol: acetic acid: water in the ratio
5:3:5 which showed a single spot of the targeted compound
.The column was then eluted using methanol in ethyl
acetate in different ratios and fractions of 10 ml were
collected. Fraction 7 and 10 of the second column of
compound 2 showed single spot which was sensitive at UV
254. These fractions were collected mixed concentrated and
left overnight to obtain 0.12 mg pure compound 2 which
was identified as quercitin. (Hao Liu et.al., 2010, Fathy M.
Soliman et.al., 2002, Naira Nayeem, Karvekar MD 2010,
Jolanta Nazaruk and Jan Gudej2001).
Compound 3 was isolated from fractions % (20% methanol
in ethyl acetate). The solvent system ethyl acetate:
metahnol: formic acid in the ratio 95:5:5showed a major
spot .The fractions compound 3 was eluted using the ethyl
acetate and methanol in different ratios. Fractions of 20ml
each were collected. The compound started to elute at 15%
methanol in ethyl acetate. This was then allowed to stand
overnight. Yellowish color crystals were obtained. This
was further purified and recrystallized the yield of this
fraction 0.15 mg. Compound 3 identified as apigenin
(jolanta nazaruk and jan gudej 2001).
The known flavonoids: Apigenin, keampferol and qucertin
were identified by extensive UV spectrum analyses and
NMR spectroscopic analyses as well as by comparing their
spectroscopic data with those reported in the literature
comparison of the melting point(DSC), LC-MS, IR and l3C
NMR&1H NMR spectra with literature data.
The purified compounds were injected to HPLC. The
gradient elution of solvent A [water-acetic acid (25:1 v/v)]
and solvent B (Acetonitrile) had a significant effect on the
resolution of compounds. As a result, solvent gradients
were formed, using dual pumping system, by varying the
proportion of solvent A [water-acetic acid (25:1, v/v)] to
solvent B (methanol). Solvent B was increased to 50% in 5
min and subsequently increased to 80% in 10 min at a flow
rate of 1.0 mL/min. Detection wavelength was 254,
280,360,560 nm (Susanne Schmidt1, Michaela Zietz 2010).
LC- Ms parameter jolanta nazaruk and jan gudej 2001.
Table 1 showed the phenolic compounds identified in
coriander flower powder. They are arginine, qucertin,
keampferol. The HPLC peak purity per cent of all the 3
compounds are respectively 95%, 96% and 97%. Melting
points are found to be 360.66, 625.79, and 270.19. This
table also provides mass m/2, UV spectrum nm of all the
three compounds.
In nature apigenin also exists as a dimer, biapigenin,
mainly isolated from the buds and flowers of Hypericum
perforatum, which has neuroprotective effects (Cheung Z.H
et al., 2008). Apigenin is abundantly present in common
fruits such as grapefruit, plant-derived beverages and
vegetables such as parsley, onions, oranges, tea,
chamomile, wheat sprouts and in some seasonings. One of
the most common sources of apigenin consumed as single
ingredient herbal tea is chamomile, prepared from the dried
Flowers from Matricaria chamomilla (McKay DL,

15

Blumberg J.B, 2006 and Sanjeev Shukla and Sanjay Gupta


2010).
The structure and the presence of free hydroxyl groups in
the various phenolic compounds make them an important
class of compounds. The chemical activities of these
phenolic compounds in terms of their reducing properties
as electron or hydrogen donating is important for their antioxidant activity (Hui-Ling Cheng et al., 2013).The extract
possess significant wound healing, analgesic and antiinflammatory activity (Majumdar M et al.,2007, Nayeem N
and Karverkar MD 2010). This could be due to the nature
of the phytoconstituents present in the plants like phenolic
compounds, tannins sterols etc. This resulted in the
isolation of apigenin, keampferol and quercitin. For this
study was analysed melting point of the compound and The
DSC peak purity compare with HPLC peak purity.
The figures (1a-1f) of the compound were identified and
determined by using LC-MS, FTIP, NMR and DSC
methods. The obtained compound was off white powder
with a melting point of 279.19 C. Analysis by mass
spectroscopy (ESI) gave molecular mass at 286.6 m/z. The
IR, NMR, melting point and the chemical test of compound
1 can be correlated to the available literature data of the
flavonoid keampferol.

Figure -1a - Compound-1 a LC-MS

Figure 1b -Compound-1 b FTIR

International Journal of Agricultural and Food Science 2014, 4(1): 13-21

Figure 1 c -Compound-1 c 1H NMR

Figure 1 d- Compound-1 d 13C NMR

band is found, at approx. 3425cm-1, and the other at


approx. 3322 that is most probably the result of OH
vibrations of phenol OH groups. The other most important
set of bands are the aromatic ring vibrations centered
around 1600 and 1500 cm1, which usually appear as a
pair of band structures, often with some splitting. the C=C
band vibrations of C=C group from the aromatic ring ,the
C=C vibration should occurs at approxy.1508,1454 and
1442( stretch)cm (for confirming aromatic C-H peaks
slightly above 3000 cm. its occurring in spectrum rang
2995 and 2926 cm ). The appearance and ratio of these
band structures is strongly dependent on the position and
nature of substituents on the ring. The above spectral
characteristics indicate with high probability that the
compound is kaempferol(Gangwal A . et al., 2010 and
Shafaghat , F. Salimi 2008)
The figures (2a-2f) of the compound were identified and
determined by using LC-MS, FTIP, NMR and DSC
methods. The obtained compound was off white powder
yellow colour with a melting point of 326.79 C. Analysis
by mass spectroscopy (ESI) gave molecular mass at 301.2
m/z. The IR, NMR, melting point and the chemical test of
compound 2 can be correlated to the available literature
data of the flavonoid Qucetcetin.

Figure 1 e -Compound-1 e DSC Melting point and Purity


by DSC
FTIR (KBr):3425, 3322,2955, 2926,2853, 2616,1660,
1613, 1569, 1508, 1454, 1442,UVmax (methanol) :
366,264,266 nm. 1H-NMR(dmso-d6 400 MHz) 6.1 (1H,d,
J=2.0 Hz,H-6),6.4(1H,d, J=2.0 Hz,H-8),8.0 (2H,dd,
J1=2,j2=8, Hz,H-3 and H-5),6.9 (2H,dd, J=2,j=8.0 Hz ,H2 and H-6),12.4(1h,s,h-4h-7),10.1(1h,s,h-5),9.4(1h,s,h4). 13C-NMR: (MeOH 300 MHz)158(C-8), 160 (C-6),
150(C-10), 130(C-3and C-5), 109(C-1), 116(C-2andC6), 145(C-3), 139(C-2), 165(C-9), 158.89(C-4), 123(C-5),
162(C-7), 177(C-4) (Fatma A. Ahmed et al 2011,v 2013).
The 1H-NMR spectrum of compound V displayed the
characteristic signals of the kaempferol nucleus: two
doublets at 6.1 and 6.4 ppm (J =2.3Hz), assigned to the
H-6 and H-8 protons respectively and a pair of A2B2
aromatic system protons at 6.86 and 7.97 ppm (J =8.0
Hz), assigned to H-3 and 5 and H-2,6 respectively. A
100% base peak [M]- for compound was observed at m/z
286.6 in the mass spectrum indicating the compound as
kaempferol. 13CNMRsignals were found to be in
agreement with reported values. The molecular formula
was deduced from 1H, 13C-NMR and mass spectrometry.
On the basis of spectral evidence, the structure was decided
to be kaempferol (C15H10O6, 286.6).
FTIR spectr m1660-1620 cm that is probably the result
C=C vibrations of olifinic structure from that spectrum
occurring approx. at 1660 cm( strong C=C stretch
absorption band). In the spectrum of OH vibrations two a

16

Figure 1 f- Compound-1 f HPLC Chromatogram

Figure 2 a- Compound-2 a LC-MS

Figure 2 b - Compound-2 b FTIR

International Journal of Agricultural and Food Science 2014, 4(1): 13-21

Figure 2 c - Compound-2 c DSC thermogram Melting


point and Purity by DSC

Figure 2d - Compound-2 d HPLC Chromatogram

range between 1600 and 1400 cm-1, which denotes the


axial deformation of the aromatic C=C. IR spectrum
showed characteristic peak position of active ingredientquercetin.3411 cm :O-H stretching vibration of phenol
,1663 cm :C=O aryl ketonic stretch ,1612 cm 1522cm
,1462,1450,1408:c-c aromatic ring stretch , 14101310 cm
band region occurring for Phenol or tertiary alcohol, OH
bend. the intensive band its showing approx. at 1383 cm :in
plane bending of O-H bond in aromatic hydrocarbon,1264
cm :C-O stretch of aryl ether , 1200cm:c-o stretch of
phenol , 1169 cm: C-O-C stretch and bending in
ketone,942,824,681,604cm:out of plane C-H bending of
aromatic hydrocarbon group of alcohol respectively,
present in the molecular of quercetin(. Zuhal guvenalp, l.
omur demirezer 2005, Aarti chourasiya et al.,2012,
K.Selvaraj et al ., 2013, Milena Kalegari et al., 2011,
silverstein et al., 1994).
This is an important fact, because the chemistry and
oxidation stability of the alcohol are strongly influenced by
the degree of substitution. Whether an alcohol is primary
(1), secondary (2) or tertiary (3), may be reflected in the
position of the OH stretch absorption, but typically this is
determined by the other absorptions, in particular the C-Ostretching frequency. Absorption of lower importance, but
often characteristic is assigned to another form of bending
vibration, the out-of-plane bend or wagging vibration of the
O-H. The OH bendingVibrations are broadened by
hydrogen bonding as is the stretching absorption, but often
to a lesser extent.
The figures (3a-3f) of the compound were identified and
determined by using LC-MS, FTIP, NMR and DSC
methods. The obtained compound was off white powder
with a melting point of 360.66 C. Analysis by mass
spectroscopy (ESI) gave molecular mass at 270.3 m/z. The
IR, NMR, melting point and the chemical test of compound
3 can be correlated to the available literature data of the
flavonoid apigenin.

Figure 2 e- Compound-2 e 13C NMR


The 1H- and 13C-NMR spectra of compound 2 exhibited
resonances due to aromatic systems. In the 1H-NMR
spectrum of 2, the aromatic region exhibited an ABX
system at 7.6 (1H, d, J = 2.0 Hz, H-2), 7.62 (1H, dd, J =
2.2 and 2.2 Hz, H-6), and 6.8 (1H, d, J = 8.48 Hz, H-5)
due to a 3, 4 disubstitution of ring B and a typical metacoupled pattern for H-6 and H-8 protons ( 6.1and 6.3, d, J
= 2.0 Hz). The 13C NMR spectrum showed the presence of
15 aromatic carbon signals. Based on the NMR data and
comparison of the data given in the literature, the structure
of compound 2 was identified as quercetin.The melting
point and other recorded properties of the isolated
constituents were presented.melting point of quercetin as
325 C.
The infrared spectrum revealed two absorption bands in
3409and 3324 cm-1 that typically result from the OH link
axial deformation. Moreover, the existence of an aromatic
ring may be observed, evidenced by a set of bands that

17

Figure 2f - Compound-2 f 1H NMR

Figure 3 a -Compound-3 a LC-MS


In the 1H NMR spectrum of 3, the aromatic proton signals
of two m-coupled doublets at H 6.4 and 6.1(each,J = 2.8
International Journal of Agricultural and Food Science 2014, 4(1): 13-21

Hz) showing HMQC correlations to the carbon resonances


at C6 164.5 (d) and C-8 161.9 (d),and 7.9 (3and5) and
6.9(2and 6)showing doublets(each j=12.1Hz). Phenolic
Compounds from Scutellaria pontica, T. ERS OZ, et al.,
respectively, were attributed to the H-6 and H-8 of the Aring. Two vicinally coupled doublets at H 7.9 and 6.9
(each, 2H, J = 12.1 Hz) showed long-range couplings with
the 13C NMR signal at C 128.9 (C-4) and, therefore,
were assigned to H-2/6 and H-3/5, respectively, of the
B-ring. Additionally, a singlet at H 6.7 was ascribed to H3. The assignment of H-3 was confirmed by its heteronuclear long-range correlations to C-2 ( C 121.6) and C-1

( C 121.6). The 13C NMR resonance at C 103.3 which


showed HMBC correlations with H-6 and H-8 was
attributed to C-7. Based on the above-mentioned data and
comparison of 1H and 13C NMR data with those given in
the literature, the structure was identified as apigenin. For
both flavones the vicinal CH couplings in Ring B obey the
following rules: ca. 8-9 Hz (Cq-CH-CH pathway); ca. 7 Hz
(CH-Cq-CH or Cq-COH-CH); ca. 3-5 (CH-COH-CH)(
Tayfun ERS OZ et al., 2002, Wild.TIAN Ying et al.,2009,
T.J. Mabryet et al., 1970, K.R. Markham 1982, J.B.
Harborne and T.J. Mabry 1982).

Table: 1
Compound name
Apigenin
Qucertin
keampferol

HPLC peak
purity%
95%
96%
97%

Meting point by
DSC C
360.66
326.79
279.19

Peak purity by
DSC %
96.86
98.40
98.13

Mass
m\z
270
302
286

Uv-spectrum
Nm
212,266,336
370,254,230,228
366,264,266

Figure 3 b- Compound-3 c FTIR

Figure 3c -Compound-3 DSC Thermogram melting point


and DSC by purity

Figure 3d -Compound-3 c HPLC Chromatogram

Figure 3e -Compound-3 d 1H NMR

18

Figure 3f- Compound-3 e 13C NMR


The other most important set of bands are the aromatic ring
vibrations centered around 1600 and 1500 cm1, which
usually appear as a pair of band structures, often with some
splitting. The appearance and ratio of these band structures
is strongly dependent on the position and nature of
substituents on the ring.
In the spectrum of OH vibrations one bands (stretchbonded broad strong OH alcohol) are found, one at approx.
3324 cm- 1.the intensive band at 3130-3070 cm is probably
the result of c-h vibration of aryl group from the aromatic
ring, c-h band at occurs in approx.3095 cm. The intensive
band at 1609 cm-1 is most probably the result of C=O
vibrations of C=O group from the central heterocyclic ring,
while the C-O vibration should occur at approx.
1163.8cm-1(strong). The other most important set of bands
are the aromatic ring vibrations centered around 1600 and
1500 cm1, which usually appear as a pair of band
structures, often with some splitting. The C=C band
vibrations of C=C group from the aromatic ring, the C=C
vibration should occurs at approxy.1502, 1444 and
1400(stretch) cm (for confirming aromatic C-H peaks
slightly above 3000 cm. its occurring in spectrum rang3095
cm). The appearance and ratio of these band structures is
strongly dependent on the position and nature of
substituents on the ring. The above spectral characteristics
indicate with high probability that the compound is
apigenin(jordan Sinia orevi et al., 2000, Charlie
Corredor a etal., 2009, Mabry, T. J., et al., 19

International Journal of Agricultural and Food Science 2014, 4(1): 13-21

Conclusion
For this article were studied and identified flavonoids and
phenolic acid etc., compare to this leaves, flower are also
having same compounds ,there is no any significant
changes from this plant. Methanolic extract of coriander
flower Out of ten fractions have been isolated instead of
these only three and purified and achieved above 95%
purity. And moreover, HPLC peak purity were compare to
DSC peak purity, its more or less counterpart to HPLC
peak purity .A significant phenolic content in agreement
with good radical Scavenging activity and therapeutically
value for health.
References
1. Mahesh Chand Meena and Vidya Patni. 2008.
Isolation and Identification of Flavonoid "Quercetin"
from Citrullus colocynthis (Linn.) Schrad. Asian J.
Exp. Sci., Vol. 22, No. 1; 137-142.
2. Susanne Schmidt1, Michaela Zietz, Monika
Schreiner1, Sascha Rohn, Lothar W. Kroh and
Angelika Krumbein. 2010. Identification of complex,
naturally occurring flavonoid glycosides in kale
(Brassica oleracea var. sabellica) by high-performance
liquid
chromatography
diode-array
detection/
electrospray ionization multi-stage mass spectrometry.
3. Shang-Tse Ho, Yu-Tang Tung, Kai-Chung Cheng,
Jyh-Horng Wu. 2010. Screening, determination and
quantification of major antioxidants from Balanophora
laxiflora flowers, Food Chemistry, 122; 584588.
4. Pietta, P. G. 2000. Flavonoids as antioxidants. Journal
of Natural Products, 63, 10351042
5. Haslam E .1998. Practical Polyphenolics: From
Structure to Molecular Recognition and Physiological
Action. Cambridge: Cambridge University Press.
6. Harborne JB .1994. The Flavonoids: Advances in
Research Since 1986. London: Chapman & Hall.
7. PLTM Karin Janssen, Ronald P Mensink, Frank JJ
Cox, Jan L Harryvan, Robert Hovenier, Peter CH
Hollman, and Martijn B Katan .1997. Effects of the
flavonoids quercetin and apigenin on hemostasis in
healthy volunteers: results from an in vitro and a
dietary supplement study13 1.
8. Khnau J. 1976. The flavonoids. A class of semiessential food components: their role in human
nutrition. World Rev Nutr Diet; 24:11791.
9. Markham .KR. 1989. Flavones, flavonols and their
glycosides. Methods Plant Biochem; 1:197235.
10. Herrmann K. 1988. On the occurrence of flavonol and
flavone glycosides in vegetables. Z Lebensm Unters
Forsch; 186:15.
11. Herrmann K. 1976. Flavonols and flavones in food
plants: a review. J Food Technol; 11:43348.
12. Hertog MGL, Hollman PCH, Katan MB, Kromhout D.
1993. Intake of potentially anticarcinogenic flavonoids
and their determinants in adults in The Netherlands.
Nutr Cancer; 20:219.
13. Keli SO, Hertog MGL, Feskens EJM, Kromhout D.
1996. Dietary flavonoids, antioxidant vitamins, and
incidence of stroke. Arch Intern Med; 156:63742.
14. Knekt P, Reunanen RJ, Maatela J. Flavonoid intake
and coronary mortality in Finland: a cohort study. Br

19

Med J 1996; 312:47881.


15. Hertog MGL, Kromhout D, Aravanis C, et.al. 1995.
Flavonoid intake and long-term risk of coronary heart
disease and cancer in the seven countries. Arch Intern
Med; 155:3816.
16. Hertog MGL, Feskens EJ, Hollman PCH, Katan MB,
Kromhout D. 1993. Dietary antioxidant flavonoids and
risk of coronary heart disease: the Zutphen Elderly
Study. Lancet; 342: 100711.
17. Rimm ER, Katan MB, Ascherio A, Stampfer MJ,
Willett WC. 1996. Relation between intake of
flavonoids and risk for coronary heart disease in male
health professionals. Arch Intern Med; 125:3849.
18. Hertog MGL, Sweetnam PM, Fehily AM, Elwood PC,
Kromhout D. 1997. Antioxidant flavonols and
ischemic heart disease in a Welsh population of men:
the Caerphilly Study. Am J Clin Nutr; 65:1489- 94.
19. Hollman PCH, Hertog MGL, Katan MB. 1996. Role of
dietary flavonoids in protection against cancer and
coronary heart disease. Biochem Soc Trans; 24:7859.
20. Hertog MGL, Hollman PCH. 1996. Potential health
effects of the dietary flavonol quercetin. Eur J Clin
Nutr; 50:6371
21. Gordon M.C. and David J.N. 2001. Natural product
drug discovery in the next millennium. Pharm. Biol.,
39, 8-17.
22. Lamson D.W. and Brignale M.S. 2000. Antioxidants
and cancer III: quercetin. Alt.Med. Rev., 5, 196-208.
23. Middleton E. and Kandaswami C. 1993. The impact of
plant flavonoids on mammalian
24. Biology: Implications for immunity
25. Wink M. 1999. Introduction Biochemistry, role and
biotechnology of secondary products. In: M Wink, Ed,
and Biochemistry of Secondary Product Metabolism.
CRC Press, Boca Ratom, FL, pp. 1-16.
26. Winkel-Shirley, B. 2002. Biosynthesis of flavonoids
and effects of stress. Curr. Opin.
27. Plant Biol., 5, 218-223.
28. Springob K. and Saito K. 2002. Metabolic engineering
of plant secondary metabolism: Promising approach to
the production of pharmaceuticals. Sci. Cul., 68, 76-85.
29. Long-Ze Lin, James M. Harnly.2010. Identification of
the phenolic components of chrysanthemum flower
(Chrysanthemum morifolium Ramat) Food Chemistry
120; 319326.
30. Hao Liu, Yan Mou, Jianglin Zhao, Jihua Wang, Ligang
Zhou, Mingan Wang Daoquan Wang, Jianguo Han,
Zhu Yu and Fuyu Yang . 2010. Flavonoids from
Halostachys caspica and Their Antimicrobialand
Antioxidant Activities Molecules, 15, 7933-7945; doi:
10.3390/molecules15117933.
31. Fathy M. Soliman, Afaf H. Shehata, Amal E. Khaleel
and Shahera M. Ezzat . 2002. An Acylated Kaempferol
Glycoside from Flowers of Foeniculumvulgare and F.
DulceMolecules, 7, 245.251.
32. Franois N. Muanda, Rachid Soulimani, Amadou
Dicko. 2011. Study on biological activities and
chemical composition of extracts from Desmodium
adscendens leaves Journal of Natural Products, Vol. 4,
100-107.

International Journal of Agricultural and Food Science 2014, 4(1): 13-21

33. Naira Nayeem, Karvekar MD. 2010. Isolation of


phenolic compounds from the methanolic extract of
Tectona Grandis April June, RJPBCS Volume 1
Issue 2.
34. Kamran G, Yosef G,Mohammed Ali. Pak J Pharm Sci
2009; 22(3) 277-28.
35. Sarvanakumar A,Venkateshwaran K,Vanitha J,Ganesh
M et al. Pak J Pharm Sci 2009; 22(3): 282-286.
36. Marian N,Fereidoon S. J Chroma A 2004;1054:94-111.
37. Majumdar M, Nayeem N, Kamath JV, Asad M. Pak J
Pharm Sci 2007; 20(2):120-4.
38. Nayeem N and Karverkar MD. Internet J Pharmacol
2010; 8 (1).
39. Fatma A.Ahmed Inas M .Abd Ei-wahab khamis and
samar y.desoukey flavonoid of neotorularia aculeolata
plant jouranal of pharmacy and nutrition science. 2011,
1,134-138.
40. Rutinoside and vicianoside of quercetin,apigenin and
luteolin from symphorcarpus albus l. blanke
(caprifoliaceae)wieslawa
bylaka
and
irena
matlawskadrug research vol 56 no.3 pp-249-252-1999.
41. Muhammad Khalid Saeed, Yulin Deng, Zahida
Perveen, Waqar Ahmad, Rongji Dai And Yuhong Yu
Optimal recovery of Apigenin from Torreya grandis by
extraction, fractionation and structure elucidation
Proceedings of the 2006 WSEAS Int. Conf. on Cellular
& Molecular Biology, Biophysics & Bioengineering,
Athens, Greece, July 14-16, pp32-38.
42. Nawal, H. Mohamed and Atta, E. M. 2006. Cytotoxic
and Antioxidant Activity of Marrubium vulgare and its
Flavonoid Constituents 2nd International Conference on
Chemical, Environmental and Biological Sciences
(ICCEBS'2013) March 17-18, 2013 Dubai (UAE)
43. antiinflamatory and antioxidant flavonoid and phenols
from cardiospermum halicacabum.hui-ling cheng et
al., journal of traditional and complementary medicine
vol.3 no.1 pp+33-40 2013.
44. Medicinal benefits of coriander (Coriandrum Sativum
L) Kiniin (Coriandrum Sativum L) Faydalar sapuula
Ullagaddi Rajeshwari, Bondada AndalluTbbi dd2011-1(1):51-58
45. http://www.medical encyclopedia.com [Access date:
10.11. 2010].
46. Sanjeev Shukla and Sanjay Gupta Apigenin: A
Promising Molecule for Cancer Prevention Pharm Res.
2010 June ; 27(6): 962978. Doi: 10.1007/s11095-0100089-7.
47. McKay DL, Blumberg JB. A review of the bioactivity
and potential health benefits of chamomile tea
(Matricaria recutita L.). Phytother Res 2006; 20:519
530. [PubMed: 16628544]
48. Cheung ZH, Leung MC, Yip HK, Wu W, Siu FK, So
KF. 2008. A neuroprotective herbal mixture inhibits
caspase-3-independent apoptosis in retinal ganglion
cells. Cell Mol Neurobiol; 28:137155.
49. The Isolation of Carboxylic Acids from the Flowers of
Delphinium formosum Received Nedime DURUST_
et al 06.09.1999.
50. Susanne Schmidt, Michaela Zietz, Monika Schreiner1,
Sascha Rohn, Lothar W. Kroh and Angelika

20

51.

52.

53.

54.

55.

56.
57.

58.

59.

60.

61.

62.

63.

Krumbein1.2010. Identification of complex, naturally


occurring flavonoid glycosides in kale (Brassica
oleracea var. sabellica) by high-performance liquid
chromatography diode-array detection/electrospray
ionization multi-stage mass spectrometry.
Shang-Tse Ho, Yu-Tang Tung, Kai-Chung Cheng,
Jyh-Horng Wu Screening, determination and
quantification of major antioxidants Food Chemistry
122 (2010) 584588.from Balanophora laxiflora
flowers
Sinia orevi1, Milorad Caki1, Salameh Amr the
Extraction of Apigenin and Luteolin from the Sage
Salvia Officinalis L. FROM JORDAN 2001.
Janmejai K Srivastava and Sanjay Gupta. 2009.
Extraction, Characterization, Stability and Biological
Activity of Flavonoids Isolated from Chamomile
Flowers Mol Cell Pharmacol. January 1; 1(3): 138.
Mara L. Tereschuk, Mario D. Baigor, Lucia I. C. de
Figueroa, and Lidia R. Abdala Flavonoids From
Argentine Tagetes (Asteraceae) With Antimicrobial
Activity Methods in Molecular Biology, vol. 268.
Jolanta Nazaruk and Jan Gudej .2001.Qualitative and
Quantitiescharomatographicinvestigation of flavonoids
in bellis perennis l., durg reach vol.58 no.5 pp401-40.
http://www.wangfei.ac.cn/notes/1/27.html
Triterpenoid, flavonoids and sterols from Lagenaria
siceraria fruits Gangwal A., Parmar S. K., Sheth N. R.
Department of Pharmaceutical Sciences, Saurashtra
University, Rajkot, India Der Pharmacia Lettre, 2010:
2 (1) 307-317 (http://scholarsresearchlibrary.com/
archive.html)
Shafaghat , F. Salimi Extraction and Determining of
Chemical Structure of Flavonoids in Tanacetum
parthenium (L.) Schultz. Bip. from IranJ. Sci. I. A. U
(JSIAU), Vol 18, No. 68, Summer 2008 39.
Flavonol Glycosides from Asperula arvensis L. Zuhal
GUVENALP, L. Omur DEMIREZER Turk J Chem
29 (2005), 163 {169.C TUBITAK.
Aarti chourasiya, Anil Upadhayay , R.N. shukla. To
Assess Isolation of quercetin- from the leaves of
Azadirachta indica and antidiabetic study of The crude
extracts. Journal of pharmaceutical and biomedical
sciences (J Pharm Biomed Sci.) 2012, December;
25(25); 179-181. (Article no 11).
K. Selvaraj, Ranjana Chowdhury, Chiranjib
Bhattacharjee.Isolation and structural elucidation of
flavonoids from aquatic fern azolla microphylla and
evaluation of free radical scavenging activity
International Journal of Pharmacy and Pharmaceutical
Sciences ISSN- 0975-1491 Vol 5, Suppl 3, 2013.
Phytochemical constituents and preliminary toxicity
evaluation of leaves from Rourea induta Planch.
(Connaraceae) Milena Kalegari, Marilis Dallarmi
Miguel, Josiane de Ftima Gaspari Dias, Ana Lusa
Lacava Lordello, Cristina Peitz de Lima, Cristina
Mayumi SasakiMiyazaki, Sandra Maria Warumby
Zanin1, Maria Christina dos Santos Verdam1, Obdulio
Gomes MiguelBrazilian Journal of Pharmaceutical
Sciences vol. 47, n. 3, jul./sep., 2011.
Silverstein, R.M.; Bassler, F.X.; Morril, T.C. Identifi-

International Journal of Agricultural and Food Science 2014, 4(1): 13-21

64.
65.
66.

67.

68.

69.

cao espectromtrica de compostos orgnicos. 5.ed.


Rio de Janeiro: Guanabara Koogan, 1994. 387.
P.K. Agrawal, \Carbon-13 NMR of Flavonoids",
Elsevier Science, New York, (1989).
J.B. Harborne, \The Flavonoids", Chapman & Hall,
(1994).
Interpretation of Infrared Spectra, A Practical
Approach John Coates John Wiley & Sons Ltd,
Chichester, 2000.
Phenolic Compounds from Scutellaria pontica Tayfun
ERS OZ, U. Sebnem HARPUT, Iclal SARACOGLU,
Ihsan CALIS Turk J Chem 26 (2002), 581 -588.
Apigenin glycosides from Euphorbia humifusa
Wild.TIAN Ying, LIU Xi-qiao, DONG Jun-xing Acta
Pharm Sin, 2009, 44: 496-499.
T.J. Mabry, K.R. Markham and M.B. Thomas, \The
Systematic Identi_cation of Flavonoids", SpringerVerlag, Berlin (1970).

70. K.R.
Markham,
\Techniques
of
Flavonoid
Identi_cation", Academic Press, London (1982).
71. J.B. Harborne and T.J. Mabry, \The Flavonoids:
Advances in Research", Chapman and Hall Ltd.,
London (1982).
72. The extraction of apigenin and luteolin from the sage
salvia officinalis l. from jordan Sinia orevi,
Milorad Caki, Salameh Amr Working and Living
Environmental Protection Vol.1,No5,2000, pp. 87 93
73. Raman and surface-enhanced Raman spectra of
chrysin, apigenin and luteolin Charlie Corredor a,
Tatyana Teslova a,1, Maria Vega Canamares a,
Zhanguo Chen a, Jie Zhang a, John R. Lombardi a,
Marco Leona Vibrational Spectroscopy 49 (2009)
190195.
74. Mabry, T. J., K. R. Markham and M. B. Thomas, The
Systematic Identification of Flavonoides, Springer
Verlag, New York-Heidelberg-Berlin 1970.

Source of support: Nil; Conflict of interest: None declared

21

International Journal of Agricultural and Food Science 2014, 4(1): 13-21

Potrebbero piacerti anche