Furocoumarins of Psoralea drupaceae


Abubakirov, N.K.; Khalmurzaev, U.F.

Khimiya Prirodnykh Soedinenii 3(2): 137-138

1967


The composition of the furocoumarins of Psoralea drupaceae Bge. (drupe scurfpea), family Leguminosae has been studied. It has been found photometrically that the kernel of the seeds contains 1.36%, the seed hull 0.07%, the seed as a whole 0.92%, the leaves 0. 06%, and the roots 0.36% of total furocoumarins on the air-dry weight of the raw material.

BRIEF
COMMUNICATIONS
FUROCOUMARINS
OF
PSORALEA
DRUPACEAE
N.
K.
Abubakirov
and
U.
F.
Khalmurzaev
Khimiya
Prirodnykh
Soedinenii,
Vol.
3,
No.
2,
pp.
137-138,
1967
The
composition
of
the
furocoumarins
of
Psoralea
drupaceae
Bge.
(drupe
scurfpea),
family
Leguminosae
has
been
studied.
It
has
been
found
photometrically
that
the
kernel
of
the
seeds
contains
1.36%,
the
seed
hull
0.07%,
the
seed
as
a
whole
0.92%,
the
leaves
0.
06%
,
and
the
roots
0.36%
of
total
furocoumarins
on
the
air-dry
weight
of
the
raw
material.
To
obtain
the
furocoumarins,
a
methanolic
extract
of
the
plant
raw
material
was
concentrated
and
was
freed
from
resinous
substances
by
shaking
with
gasoline,
the
furocoumarins
were
transferred
into
benzene,
and
the
benzene
solution
was
filtered
through
a
layer
of
alumina
and
evaporated
to
dryness.
The
mixture
of
coumarins
obtained
in
this
way
was
dissolved
in
a
100
-fold
volume
of
ether.
A
crystalline
com-
pound
with
the
composition
C
11
H
6
0
3
and
mp
161
°
-16
i
i
°
0
C
H
(from
ethanol)
deposited.
(Found,
ID:
C
71.00;
H
3.32).
The
substance
was
optically
inactive.
UV
spectrum:
X
C
m
2
ax
5
243, 295,
330
mil
(log
e
4.56,
4.21,
3.96);
IR
spectrum
[1]:
1361,
3122,
3064
(C
—H
bond),
1732
(CO),
=
1636
(
C),
1581
(aromatic
ring)
cm
-1
.
All
these
properties
correspond
to
psoralen
[2,
q.
The
ethereal
solution
after
the
elimination
of
the
psoralen
was
evaporated
and
the
residue
was
transferred
to
a
column
of
alumina.
When
the
column
was
eluted
with
benzene,
the
first
fractions
yielded
an
optically
inactive
crystal-
line
compound
with
the
composition
C
11
H
6
0
3
having
mp
139
°
-140"
C
(Found,
%:
C
71.02;
H
3.20).
UV
spectrum:
x
C
2
H
5
OH
max
246,
298
mu
(loge
4.62,
4.18).
IR
spectrum:
3161,
3122,
3064
(C—
H
bond),
1743
(C=0),
1622(C=
C),
1583,
1543
(aromatic
ring)
cm
-1
.
All
these
properties
correspond
to
angelicin
(isopsoralen)
[3,
4].
The
individuality
of
the
furocoumarins
obtained
was
confirmed
by
paper
chromatography
in
the
n
-hexane—
ben-
zene—
methanol
(5:
4:1)
system.
On
treatment
with
diazotized
sulfanilic
acid,
the
psoralen
spot
was
lilac
and
that
of
angelicin
orange.
The
NMR
spectra
of
the
compounds
that
we
isolated
have
been
given
previously
[5].
The
ratio
between
the
psoralen
and
angelicin
is
approximately
the
same
in
all
the
organs
of
the
plant
(1:1).
The
mixture
of
psoralen
and
isopsoralen
from
P.
drupaceae
[6]
is
used
as
a
medicinal
preparation
in
the
treatment
of
vitiligo
[7].
Sucrose
has
also
been
isolated
from
the
roots
of
the
plant
with
a
yield
of
1%.
REFERENCES
1.
M.
E.
Perel'son,
ZhOKh,
33,
952,
1963.
2.
H.
S.
Jois,
B.
L.
Manjunath,
and
S.
V.
Rao,
J.
Ind.
Chem.
Soc.,
10,
41,
1933;
C.,
2,
77,
1933;
E.
Spath,
B.
L.
Manjunath,
M.
Pailer,
and
H.
S.
lois,
Ber.,
69,
1087,
1936.
3.
E.
Spath
and
0.
Pesta,
Ber.,
67,
853,
1934;
H.
S.
Jois
and
B.
L.
Manjunath,
Ber.,
69,
964,
1936.
4.
H.
K,
Khastgir,
P.
C.
Duttagupta,
and
P.
Sengupta,
Ind.
J.
Appl.
Chem.,
22,
82,
1959.
5.
Yu.
N.
Sheinker,
G.
Yu.
Pek,
and
M.
E.
Perel'son,
DAN
SSSR,
158,
1382,
1964.
6.
N.
K.
Abubakirov
and
U.
F.
Khalmurzaev,
USSR
author's
certificate
no.
164411,
1964;
Byull
isobr.
no.
15,
53,
1964.
7.
A.
A.
Akovbyan
and
K.
P.
Kamzolova,
Vest.
dermat.
i
vener.
,
no.
5,
33,
1961.
4
November
1966
Institute
of
the
Chemistry
of
Plant
Substances,
AS
UzSSR
115