Anti-inflammatory new coumarin from the Ammi majus L.


Selim, Y.A.; Ouf, N.H.

Organic and Medicinal Chemistry Letters 2(1): 1-1

2012


Investigation of the aerial parts of the Egyptian medicinal plant Ammi majus L. led to isolation of new coumarin, 6-hydroxy-7-methoxy-4 methyl coumarin and 6-hydroxy-7-methoxy coumarin; this is the first time they have been isolated from this plant. The structures of the compounds were elucidated by spectroscopic data interpretation and showed anti-inflammatory and anti-viral activity.

Selim
and
Ouf
Organic
and
Medicinal
Chemistry
Letters
2012,
2:1
http://www.orgmedchemlett.com/content/2/1/1
0
Organic
and
Medicinal
Chemistry
Letters
a
SpringerOpen
Journal
ORIGINAL
ARTICLE
Open
Access
Anti-inflammatory
new
coumarin
from
the
Ammi
majus
L
Yasser
Abdelaal
Selim"
and
Nabi
l
Hassan
Ouf
2
Abstract
Investigation
of
the
aerial
parts
of
the
Egyptian
medicinal
plant
Ammi
majus
L.
led
to
isolation
of
new
coumarin,
6-
hydroxy-7-methoxy-4
methyl
coumarin
(2)
and
6-hydroxy-7-methoxy
coumarin
(3);
this
is
the
first
time
they
have
been
isolated
from
this
plant.
The
structures
of
the
compounds
(2
&3)
were
elucidated
by
spectroscopic
data
interpretation
and
showed
anti-inflammatory
and
anti
-viral
activity.
Graphical
abstract:
An
efficient,
one
-new
coumarin
(2)
was
isolated
from
the
aerial
parts
of
the
A.
Majus
L.
was
evaluated
for
their
anti
-viral
and
anti-inflammatory
activities.
Keywords:
phytochemistry,
Ammi
majus
L.,
anti
-viral
activity,
natural
products,
anti-inflammatory
activity,
steroids
1.
Introduction
Fructus
Ammi
Majoris
consists
of
the
dried
ripe
fruits
of
Ammi
majus
L.
(Apiaceae)
[1,2];
originating
Egypt,
and
widely
distributed
in
Europe,
the
Mediterranean
region,
and
western
Asia,
now
cultivated
in
India
[2].
This
is
widely
used
for
the
treatment
of
skin
disorders
such
as
psoriasis
and
vitiligo
(acquired
leukoderma)
[1,3-6],
and
of
vitiligo
[1].
It
is
used
as
an
emmenagogue
to
regulate
menstruation,
as
a
diuretic,
and
for
treat-
ment
of
leprosy,
kidney
stones,
and
urinary
tract
infec-
tions
[7].
Numerous
clinical
trials
have
assessed
the
efficacy
of
Fructus
Ammi
Majoris
andxanthotoxin
for
the
treatment
of
vitiligo,
psoriasis,
and
hypopigmenta-
tion
tinea
versicolor
[4-6,8-11].
2.
Results
and
discussion
2.1.
Chemistry
The
use
of
natural
products
in
drug
manufacturing
is
an
ancient
and
well
-established
practice
[12].
Egyptian
medicinal
plants
are
well
known
by
their
diverse
uses
in
traditional
folk
medicine
to
cure
various
ailments
including
infectious
diseases
and
known
producers
of
pharmacological
and
anti
-viral
agents
[13]A.
majus
L.
is
contraindicated
in
diseases
associated
with
photosensi-
tivity,
cataract,
invasive
squamous-cell
cancer,
known
sensitivity
to
xanthotoxin
(psoralens),
and
in
children
*
Correspondence:
y2selem@yahoo.com
'Faculty
of
Specific
Education,
Zagazig
University,
Zagazig,
Egypt
Ful
l l
ist
of
author
information
is
avai
lable
at
the
end
of
the
article
Springer
under
the
age
of
12
years
[14].
The
fruits
are
also
con-
traindicated
in
pregnancy,
nursing,
tuberculosis,
liver
and
kidney
diseases,
human
immunodeficiency
virus
(HIV)
infections
and
other
autoimmune
diseases
[15].
In
this
study,
the
isolated
compounds
(2-4)
from
A.
majus
L.
were
evaluated
for
their
anti
-viral
activity
(Figure
1).
The
major
constituents
are
furanocoumarins,
the
princi-
pal
compound
beingxanthotoxin
(methoxsalen,
8-meth-
oxypsorale
[8-M01
3
])
ammoidin;
up
to,
imperatorin
(ammid-in)
and
bergapten
(heraclin,
majudin,
and
5-
methoxy
Psoralen
[5-M01
3
])
and
other
coumarins
of sig-
nificance
are
marmesin
(the
structure
of
isolated
com-
pounds)
isoimperatorin,
heraclenin,
and
isopimpinellin
constituents
of
interest
are
acetylated
fl
avonoids
[16-20].
The
dried
plant
(500
g)
of
A.
majus
L.
was
sequentially
extracted
with
hexane
and
methanol.
In
our
initial
bio-
logical
study
as
shown
in
Table
1
the
compounds
2,
3
showed
high
anti-inflammatory
activity
while
the
com-
pound
4
showed
moderate
activity.
This
effect
could
explain
the
medical
use
of
A.
majus
in
traditional
medi-
cine.
The
hexane
extract
was
chromatographed
to
give
f3-sitosterol
1
[21].
The
methanol
fraction
was
chroma-
tographed
on
silica
gel
to
give
new
coumarin
2
and
two
coumarins
3,
4.
Compound
2
showed
fl
uorescence
under
UV
indicating
it
to
be
coumarin.
The
IR
spec-
trum
of
the
compound
exhibited
the
presence
of
a
car-
bonyl
group
at
1710
cm
-1
which
was
a
further
support
toward
the
coumarin
nucleus.
MS
suggested
its
molecu-
lar
mass
to
be
206
in
agreement
with
the
formula
©
2012
Selim
and
Ouf;
licensee
Springer.
This
is
an
Open
Access
article
distributed
under
the
terms
of
the
Creative
Commons
Attribution
License
(http://creativecommons.org/licenses/by/2.0),
which
permits
unrestricted
use,
distribution,
and
reproduction
in
any
medium,
provided
the
original
work
is
properly
cited.
Selim
and
Ouf
Organic
and
Medicinal
Chemistry
Letters
2012,
2:1
Page
2
of
4
http://www.orgmedchemlett.com/content/2/1/1
HO
110
3
Figure
1
The
structure
of
isolated
compounds.
4
0
Gi
l
l
-
4
0
0
4
,
which
shows
fragments
at
m/z
193
and
162,
suggesting
that
fragmentation
is
occurring
in
the
man-
ner
associated
with
coumarin
nucleus.
'H
NMR
of
the
compound
in
CDC1
3
showed
that
no
band
was
typical
of
H-4
of
a
coumarin
and
singlet
at
6
6.25
was
assign-
able
to
H-3,
indicating
that
methyl
group
was
attached
at
position
4.
Another
doublet
was
observed
at
6
6.62,
which
could
be
H-5
of
a
coumarin.
There
was
a
singlet
at
6
6.43
and
6.82
for
two
protons
which
represented
H-6
and
H-8
of
the
nucleus.
The
13
C
NMR
spectrum
showed
resonance
for
all
11
carbon
atoms
in
the
mole-
cule.
The
spectra
revealed
the
presence
of
two
methyl,
three
methane
and
six
quaternary
carbon
atoms.
The
two
downfield
quaternary
carbon
signals
at
6,
162.5
(C-
3)
and
143.7
(C-6)
showed
the
presence
of
ketonic
and
one
hydroxyl
functionality
in
the
molecule.
The
analyti-
cal
results
obtained
from
'
3
C
NMR
spectrum
for
this
compound
was
tabulated
in
Table
2.
Compound
3
showed
fl
uorescence
under
UV
indicating
it
to
be
a
cou-
marin.
The
IR
spectrum
of
the
compound
exhibited
the
presence
of
a
carbonyl
group
at
1700
cm
-1
which
was
a
further
support
towards
the
coumarin
nucleus.
MS
sug-
gested
its
molecular
mass
to
be
192
which
agreement
with
formula
C
10
H
8
0
4
.
NMR
of
the
compound
in
CDC1
3
showed
a
doublet
at
6
6.72
which
was
typical
of
Table
1
Anti-inflammatory
data
of
the
titled
coumarin's
compounds
Compounds
Thickness
of
rat
paw
(mm)
after
3
h
%
Inhibition
after
3
h
2
0.43
±
0.008
b
37.81
3
0.41
±
0.008
b
36.80
4
0.53
±
0.009
b
28.17
Indomethacin
0.25
±
0.1
b
60.50
Control
0.72
±
0.015
The
results
were
significant.
Compared
with
control
(carrogeenin
only),
'p
<
0.05
Compared
with
Indomethacin,
b
y
<
0.01
H-4
of
a
coumarin.
Another
doublet
was
observed
at
6
Table
2
'H
NMR
and
13
C
NMR
chemical
shifts
(6/ppm)
of
(2)
and
(3)
DMSO-d
6
as
the
solvents
(25°C)
Position
DMSO-d
6
2
3
1
H
'
3
C
1
11
13
C
1
C2(C
=
0)
162.5
161
.8
C3
6.29s
113.2
7.95d
117.05
C4
152.6
6.72d
147.3
C5
6.62d
109.3
5.35d
113.4
C6(OH)
6.43d
143.7
6.25d
143.6
C7
146.8
146.2
C8
6.82d
104.9
6.80d
104.2
C9
147.5
149.7
C10
112.5
111
.3
C11(CH
3
)
2.45s
19.8
C12(OCH
3
)
3.84s
56.3
3.79s
56.1
5.35
which
could
be
H-5
of
a
coumarin.
There
was
a
singlet
at
6
6.25
and
6.80
for
two
protons
which
repre-
sented
H-6
and
H-8
of
the
nucleus.
The
analytical
results
obtained
from
13
C
NMR
spectrum
for
this
com-
pound
were
tabulated
in
Table
2.
To
the
best
of
the
authors'
knowledge,
the
coumarin
compound
3
has
not
previously
been
isolated
from
this
family.
The
'H
NMR
data
of
furancoumarin
system
were
closely
similar
to
compound
4,
which
included
two
doublets
at
6
6.30
and
8.27
attributed
to
the
pyran
ring
protons
H-3
and
H-4,
two
other
doublets
at
6
7.19
and
7.80
corresponding
to
the
furan
ring
protons
H40
and
H-9,
and
one
olefinic
proton
at
6
7.20
(s)
for
H-8.
The
data
proposed
com-
pound
4
to
be
xanthotoxin
[16-20].
2.2.
Biological
studies
2.2.1.
Anti-inflammatory
activity
The
pharmacological
evaluation
of
the
tested
com-
pounds
(2-4)
was
carried
out
as
per
the
protocol
speci-
fied.
The
anti-inflammatory
activity
of
the
synthesized
compounds
was
carried
out
using
the
carrageenan-
induced
rat
paw
edema
method.
The
anti-inflammatory
activity
data
for
the
compounds
are
given
in
Table
1.
At
the
dose
level
of
0.01
mg/100
g,
(2,
3)
exhibited
appreci-
able
inhibition
of
edema,
especially
2,
which
exhibited
a
87%
of
edema
inhibition
of
37.81%,
which
was
compar-
able
to
that
of
the
standard
drug
indomethacin
(60.50%
at
0.01
mg/100
g
dose)
where
the
compound
4
exhibited
mild
anti-inflammatory
activity.
2.2.2.
Anti
-viral
activity
The
compounds
(2-4)
found
to
have
antiviral
activity,
[13]
against
vesicular
stomatitis
virus
(VSV)
in
a
con-
centration
-dependent
manner
at
complete
non-toxic
concentration
range
10400
µg/ml
(Rf
10(5)),
10400
lig/
ml
(Rf
10(4)),
and
50400
µg/ml
(Rf
10(3)),
respectively.
Selim
and
Ouf
Organic
and
Medicinal
Chemistry
Letters
2012,
2:1
Page
3
of
4
http://www.orgmedchemlett.com/content/2/1/1
All
these
compounds
are
found
to
have
no
reliable
anti-
viral
activity
against
herpes
simplex
virus
(HSV).
3.
Materials
and
methods
3.1.
General
The
1
H
NMR
and
13
C
NMR
spectra
were
recorded
at
270
and
68.5
MHz,
respectively,
with
TMS
as
an
inter-
nal
standard
using
a
270
-MHz
JEOLJNM
Ex
-270/4000
NMR
instrument.
Optical
rotations
were
determined
on
a
JASCO
P-1020
polarimeter
using
a
100
-mm
glass
microcell.
IR
spectra
(KBr)
were
recorded
on
a
Perkin-
Elmer
1650
FT-IR
spectrometer.
The
UV
spectra
were
recorded
with
a
Perkin-Elmer
Lambda
2UV/VIS
spec-
trophotometer.
The
melting
points
were
determined
using
a
Digital
Melting
Point
Apparatus
(model
IA
8103,
Electro
thermal
Engineering
Ltd,
Soutthend-on-
Sea,
Essex,
UK).
MS
were
measured
on
a
GSMS-QP-
1000EX
gas
chromatograph-mass
spectrometer
SHI-
MADZU-Japan.
For
column
chromatography,
silica
gel
(Merk.
63-200
pm
particle
size)
was
used.
TLC
was
car-
ried
out
with
Merl<
silica
gel
60F254
Plates.
UV
light
(245
and
366
mm)
and
spraying
with
vanillin
-sulfuric
acid
reagent
followed
by
heating
(120
C)
were
used
for
detection.
3.2.
Plant
material
The
aerial
parts
of
the
A.
Majus
L.
were
obtained
from
local
market,
Egypt,
in
March
2010.
The
plant
material
has
been
deposited
at
the
Laboratory
of
Botany,
Faculty
of
Science,
and
Zagazig
University,
Egypt.
3.3.
Extraction
and
isolation
The
air-dried
plant
(500
g)
was
powdered
and
extracted
with
hexane
(1.6
1)
at
room
temperature
(25°
C)
for
30
min,
and
the
hexane
solution
was
evaporated
in
vacuo
to
give
a
residue
(21
g).
The
methanol
extract
(32
g)
was
obtained
by
the
same
procedure.
The
hex-
ane
(20
g)
was
chromatographed
over
silica
gel
(200
g)
using
hexane
with
increasing
amounts
of
ethyl
acetate
(5:1)
to
f3-sitosterol
(1
C
29
H
50
0).
It
is
crystallized
from
methanol
(20
mg;
from
Hexane-EtOAc
9:1,
R
f
=
0.22
Light
petroleum:
EtOAc
2:1);
mp
136°C
(literature
mp
136-137°C)
[22].
It
responded
to
Liebermann-Burchard
Reaction.
IRv
max
(KBr,
cm
-1
)
3427;
1
H
NMR
(6,
DMSO),
5.34
(1H,
br,
H-6),
3.51
(1H,
m,
H-3),
2.28-
1.13
(29H,
m,
11*CH
2
,
7*CH),
0.92
(6H,
s,
2*CH3),
0.83
(3H,
s,
CH
3
),
0.80
(3H,
s,
CH
3
),
0.78
(3H,
s,
CH
3
),
0.68
(3H,
s,
CH
3
);
GCMS:
414
(M+).
This
data
con-
firmed
compound
1
to
be
f3-sitosterol
1
[21]
using
a
direct
comparison.
The
methanol
extract
(30
g)
was
chromatographed
on
a
silica
gel
column
using
succes-
sively
hexane
-ethyl
acetates
eluent
to
give
three
cou-
marin
compounds
(2-4).
3.4.
6-Hydroxy-7-methoxy-4
methyl
coumarin
(2
C11111004)
White,
amorphous
solid
(53
mg;
from
CH
2
C1
2
-EtOAc
8:2,
R
f
=
0.19
Light
petroleum:
EtOAc
2:1);
mp
204-206°
C;
+41.4
(CHC1
3
);
UV
218;
IR
(KBr)
Yrnax
3620
(OH),
1710
(C
=
0)
cm
-1
;
1
H
NMR
and
13
C
NMR,
see
Table
2;
m/z
206
191(100),
160(17), 143(24);
anal.
calcd
for
C
11
I
-
1
10
0
4
%
C
64.06,
%
H
4.9,
%
0
31.3;
found
%
C
64.03,
%
H
4.21,
%
0
31.1.
3.5.
6-Hydroxy-7-methoxy-coumarin
(3
C10H804)
White,
amorphous
powder
(61
mg;
from
CH
2
C1
2
-EtOAc
3:1,
R
f
=
0.16
Light
petroleum:
EtOAc
2:1);
mp
183-185°
C;
[c]p
+46.6
(CHC1
3
);
UV
220;
IR
(KBr)
Yrnax
3640
(OH),
1700
(C
=
0);
1
H
NMR
and
13
C
NMR,
see
Table
2;
m/z
192
177(17),
161(100)
144(25);
anal.
calcd
for
C
1
oH
8
0
4
%
C
62.04,
%
H
4.21,
%
0
33.2;
found
%
C
61.9,
%
H
4.43,
%
0
32.8.
3.6.
Xanthotoxin
(4
C12H804)
White,
amorphous
powder
(26
mg;
from
CH
2
C1
2
-EtOAc
1:1);
mp
158-160°C;
[a]p
+46.6
(CHC1
3
).
The
data
from
IR
(KBr),
1
H
NMR
and
13
C
NMR
proposed
that
com-
pound
3
is
xanthotoxin
[16-20];
anal.
calcd
for
C121
-
1804
%
C
66.64,
%
H
3.71,
%
0
29.2;
found
%
C
66.49,
%
H
3.43,
%
0
29.8.
3.7.
Biological
studies
3.7.1.
Anti-inflammatory
activity
The
anti-inflammatory
activity
was
evaluated
by
hind
paw
oedema
method
[23].
Albino
rats
of
weighing
100-
150
g,
of
either
three
compounds
(2-4),
using
Indo-
methacin
as
a
standard,
were
divided
into
five
groups
of
six
animals.
The
animals
were
maintained
under
normal
environmental
conditions.
To
each
group,
with
the
exception
of
the
control
group,
the
tested
compounds
(0.01
mg/100
g
of
body
weight)
were
administered,
injected.
To
one
group,
the
standard
drug
Indomethacin
(0.01
mg/100
g)
was
administered.
After
1
h,
carragee-
nan
(0.1
ml,
1%
w/v
solution
in
sterile
saline)
was
injected
into
the
sub
-plantar
tissue
of
the
left
paw
of
all
the
animals.
The
right
paw
served
as
the
reference
non
-
inflamed
paw
for
comparison.
The
initial
paw
volume
was
measured
using
a
plethysmograph
within
30
s
of
the
injection.
After
3
h,
the
final
paw
volume
of
each
animal
was
measured.
The
percentage
of
reduction
in
the
paw
volume
was
calculated
by
subtracting
the
differ-
ence
between
the
right
and
left
hind
paw
volumes
in
the
treated
group
from
the
difference
in
the
control
group
and
dividing
it
by
the
difference
in
the
control
group.
The
anti-inflammatory
tivity
of
the
tested
compounds
and
the
standard
reference
drug
was
determined
using
the
formula,
%
anti-inflammatory
activity
=
(1
-
Vj/I7c)
Selim
and
Ouf
Organic
and
Medicinal
Chemistry
Letters
2012,
2:1
Page
4
of
4
http://www.orgmedchemlett.com/content/2/1/1
x
100,
where
14
represented
the
mean
increase
in
paw
volume
of
rats
treated
with
test
compounds
and
17,
represented
the
mean
increase
in
paw
volume
in
the
control
group
of
rats.
3.7.2.
Anti
-viral
activity
In
this
study,
the
compounds
(2-4)
were
evaluated
for
their
anti
-viral
activity.
These
compounds
were
tested
against
two
mammalian
viruses,
HSV-1
and
VSV.
The
antiviral
activity
were
determined
by
means
of
the
end
titration
technique
that
depends
on
the
ability
of
plant
extract
dilutions
to
inhibit
the
produced
cytopathogenic
effect
and
expressed
as
reduction
factor
(R
f
)
of
the
viral
titer.
4.
Conclusion
Ammi
majus
L.
being
local
medicinal
plants
with
great
abundance
in
west
of
Egypt
are
shown
in
rich
in
anti-
viral
and
anti-inflammatory
activities,
including
phyto-
chemicals
coumarin.{}
These
results
give
them
the
privi-
lege
to
start
intensive
studies
for
isolation
of
these
biologically
active
compounds
for
local
drug
-design
pro-
grams.
In
addition,
A.
majus
L.
is
considered
as
a
good
source
of
6-hydroxy-7-methoxy
coumarin
(3)
which
was
identified
as
the
major
coumarin.
Also,
this
is
the
first
study
to
report
the
occurrence
of
compound
(3).
Acknowledgements
The
authors
are
very
grateful
to
the
Botany
Department,
Faculty
of
Science
and
Pharmacology
Department,
Faculty
of
Pharmacy,
Zagazig
University,
for
their
help
in
identification
of
the
plants
and
farmacological
testes.
Author
details
'Faculty
of
Specific
Education,
Zagazig
University,
Zagazig,
Egypt
2
Chemistry
Department,
Faculty
of
Science,
Zagazig
University,
Zagazig,
Egypt
Competing
interests
The
authors
declare
that
they
have
no
competing
interests.
Received:
3
October
2011
Accepted:
12
January
2012
Published:
12
January
2012
References
1
.
Egyptian
Pharmacopoeia
(1972)
General
Organization
for
Government
Printing,
Cairo,
32
2.
Central
Council
for
Research
in
Unani
Medicine
(1987)
Standardisation
of
single
drugs
of
Unani
medicine
-Part
I.
Ministry
of
Health
and
Family
Welfare,
New
Delhi
3.
Hakim
RE
(1969)
Rediscovery
of
a
treatment
for
vitiligo.
Clio
Medica
4:277-289
4.
El-Mafty
AM
(1948)
A
preliminary
clinical
report
on
the
treatment
of
leucodermia
with
Ammi
majus
Linn.
J
Egypt
Med
Assoc
31
:651-665
5.
Fahmy
IR,
Abu
-Shady
H
(1948)
The
isolation
and
properties
of
ammoidin,
ammidin
and
majudin
and
their
effect
in
the
treatment
of
leukodermia.
Q
J
Pharm
Pharmacol
21
:499-503
6.
El-Mafty
AM
(1952)
Further
study
on
treatment
of
leucodermia
with
Ammi
majus
Linn.
J
R
Egypt
Med
Assoc
35:1-19
7.
NAPRALERT
database
University
of
Illinois
at
Chicago, Chicago,
IL
(an
online
database
available
directly
through
the
University
of
Illinois
at
Chica
g
o
or
through
the
Scientific
and
Technical
Network
(STN)
of
Chemical
Abstracts
Services)
Accessed
9
February
2001
8.
Parrish
JA
(1974)
Photachemotherapy
of
psoriasis
with
oral
methoxsalen
and
long
wave
ultraviolet
light.
N
Engl
J
Med
291
:1207-121
1
.
doi:10.1056/
NEJM197412052912301
.
9.
El-Mafty
AM,
El-Mafty
M
(1980)
Psoralen
photachemotherapy
in
contrast
to
chemotherapy
of
psoriasis.
Med
J
Cairo
Univ
48:71-83
10.
El-Mafty
AM,
EI-Sawalhy
H,
El-Mafty
M
(1994)
Clinical
study
of
a
new
preparation
of
8-methoxypsoralen
in
photachemotherapy.
Int
J
Dermatol
33:588-592.
doi:10.1
1 1
14.1365-4362.1994.tb02904.x.
1 1
.
El-Mafty
AM,
EI-Sawalhy
H,
El-Mafty
M
(1995)
Photachemotherapy
in
the
treatment
of
post
tinea
versicolor
hypopigmentation.
Med
J
Cairo
Univ
61(4):632-637
12.
Yasuhara-Bell
J,
Yang
Y,
Barlow
R,
Trapido-Rosenthal
H,
Lu
Y
(2010)
In
vitro
evaluation
of
marine
-microorganism
extracts
for
anti
-viral
activity.
Virol
7:182.
doi:10.1
186/1743-422X-7-182.
13.
Soltan
MM,
Zaki
Al"
(2009)
Antimicrobial
and
antiviral
activities
of
some
Egyptian
medicinal
plants.
J
Ethnopharmacol
126(1):102-107.
doi:10.1016/j.
jep.2009.08.001
.
14.
Lacy
C
(2000)
Drug
information
handbook.
Lexicomp,
Hudson,
OH,
6
15.
Wagner
H,
Wisenauer
ML
(1995)
Phytotherapie.
[Phytotherapy.1.
Gustav
Fischer,
Stuttgart
16.
Abu-Mustafa
EA,
Fayez
MBE
(1961)
Natural
coumarins.
I.
Marmesin
and
marmesinin,
further products
from
the
fruits
of
Ammi
majus
L.
J
Org
Chem
26:161-166.
doi:10.10214001060a039.
17.
Hilal
SH,
Haggag
MY
(1975)
A
thin
-layer
chromatography
(TLC)
calorimetric
assay
of
furocaumarins.
Egypt
J
Pharm
Sci
16:495-499
18.
Abdulla
WA
(1978)
Preliminary
studies
on
the
anti-schistosomal
effect
of
Ammi
majus
L.
Egypt
J
Bilharziasis
4:19-26
19.
Ivie
GW
(1978)
Linear
furocaumarins
(psoralens)
from
the
seed
of
Texas
Ammi
majus
L.
(Bishop's
weed).
J
Agric
Food
Chem
26:1394-1403.
doi:10.1021/jf60220a023.
20.
Singab
ANB
(1998)
Acetylated
fl
avonal
triglycosides
from
Ammi
majus
L.
Phytochemistry
49:2177-2180.
doi:1
aioi
cvs0031-9422(98)00417-8.
21
.
Meera
M,
Kumar
5,
Kalidhar
SB
(1999)
Phytochemical
investigation
of
Parkinsonia
ff
uleata.
Indian
J
Pharm
Sci
61
:315-316
22.
Heilbron
I,
Cook
AH,
Bunbury
HM,
Hey
DH
(1965)
Dictionary
of
organic
compounds.
Eyre
and
Spottiswoode,
London
23.
Winter
CA,
Risley
EA,
Nuss
GW
(1962)
Carrageenan-induced
oedema
in
hind
paw
of
the
rat
as
an
assay
for
anti-inflammatory
drugs.
Proc
Sac
Exp
Biol
Med
1 1 1
:544-547
doi:10.1186/2191-2858-2-1
Cite
this
article
as:
Selim
and
Ouf:
Anti-inflammatory
new
coumarin
from
the
Ammi
majus
L.
Organic
and
Medicinal
Chemistry
Letters
2012
2:1.
Submit
your
manuscript
to
a
SpringerOpen
0
journal
and
benefit
from:
Convenient
online
submission
Rigorous
peer
review
Immediate
publication
on
acceptance
Open
access:
articles
freely
available
online
High
visibility
within
the
fi
eld
Retaining
the
copyright
to
your
article
Submit
your
next
manuscript
at
springeropen.com