1. WELCOME

2. CONTENTS
COUMARINS
CLASSIFICATION
PSORALEN
XANTHOTOXIN
REFERNCES

3. COUMARINS
Coumarin (2H-chromen-2-
one) is a fragrant organic
chemical compound in
the benzopyrone chemical
class, which is a colorless
crystalline substance in
its standard state It is found
naturally in many plants
Families : umbelliferae,
rutaceae, leguminaceae,etc
Carribean word : coumarou

4. CLASSIFICATION
1. Simple coumarins, such as coumarin
itself and dihydrocoumarin,
coumarin dihydroxycoumarin

5. 2.Furocoumarins are formed in result of
furan ring and coumarin condensation in
6,7 positions (psoralen-derivatives) or 7,8
(angelicin-derivatives). Substitutes may
occur within any of these rings
psoralen angelicin

6. 3. Pyranocoumarins are result of condensation of
coumarin with 2’2’-dimethylpyrane in positions 5,6
(dimethylxantyletin); 6,7 or 7,8 (visnadine) and may
have substitutes in any of rings.
2’2’dimethylxantyletin visnadin

7. 4. Benzocoumarins containing benzyl ring
condensed with coumarin in 3,4
positions occur Anacardiaceae and Rosaceae. Hy
droxyderivative of 3,4-benzocoumarin is a
structural component of ellagic acid.
3,4-benzocoumarin-hydroxy-derivative

9. PSORALEN
Synonym: Ficusin
Parent compound in
the family of
furanocoumarins
Umbeliferon
derivative
Linear furanocoumrin

10. BIOLOGICAL SOURCE
 Dried ripe fruits of
psoralea corylifolia
 Family :Leguminosae
 Content of the fruit:
◦ Psoralen
◦ Isopsoralen
 It is present up to 3-4 %
in the fruit

11. PSORALEA DERIVATIVES :
imperatoxin
xanthotoxin
bergapten
isomer :
angelicin

12. SOLUBILITY:
 Very soluble in chloroform
 Less soluble in alcohol
 Sparingly soluble in ether
 Insoluble in petroleum ether

13. STRUCTURE
OO O
7H-furo[3,2, benzopyran-7-one
Molecular formula :C11H6O3

14. CONSTITUTION
 Structure of psoralen is deduced by using
its degradation reaction
 It exhibits normal reactions of lactone of
coumarin such as ring opening by alkali to
give coumarinic acid or coumaric acid
derivatives
 potassium permanganate causes oxidation
of furan ring
 other oxidation produce furan 2,3-
dicarboxylic acid

15. ISOLATION
Dried fruits of Psoralea
corylifolea
Coarse
powder
To remove
essential oils
&resinous matter
present on outer
coat
Defatted with petroleum ether
Dried the
marc

16. Extracted with methanol
Methanolic extract (psoralen +other
coumarins +flavanoids)
Concentrate & dry
Chromatographed on silica gel
plate
Chloroform
as eluent
Psoralen in first few
fraction
Crystallised from
ethanol or solvent
ether
Concentrate to yield
psoralen

17. IDENTIFICATION TESTS
 1mg of psoralen in 5ml of ethanol+3 parts
of propylene glycol+43 parts of water
Blue fluoresence
 1mg psoralen in 2ml ethanol+2 drops of
0.1M NaOH Emits yellow
flourescence
Uv
light
Uv
light

18. 1mg of Psoralen
in1ml of
methanol
Spotted on
silicagel-G plates
Plates are eluted in
benzene:chloroform
(98:2)
Dried plates
observed under
UV light
Psoralen shows blue fluracent
spot with Rf value 0.25

19. USES
 In PUVA treatment for skin disease
◦ Psoriasis
◦ eczema
◦ vitiligo
 Recommended in the treatment of
alopecia
 Psoralen is a mutagen & is used in
molecular biology research
 Tannin activator in sun screens

20. SYNTHESIS
O OH
2,3-dihydrobenzofuran
CO, HCl
CuCl ,AlCl 3 O OH
O
H
(CH3CO) 2O CH3COONa
O O O
Pd
2+
O O O
psoralen
Guttermann Koch reacion
Perkin Condensation
dehydrogenation
7-hydroxy derivative of

21. O OOH
Umbellliferone
OPPCH3
CH3
attack of DMAPP
CH3
OH O O
CH3
O2
NADPH
OO O
Demethylsuberosin
Marmesin
O2
NADPH
OO O
OO O
OCH 3
O
O
O
Psoralen
Angelicin
O2
NADPH
BIOSYNTHESIS

23. Xanthotoxin or Methoxsalen is extracted
from Ammi majus, a plant of the family
Umbelliferae. It modifies the way skin
cells receive the UV radiation.
AMMI MAJUS - Bishops flower, Queen
Anne’s Lace
Also known as Bishopsweed, Bishop’s
weed, Bullwort, Greater ammi, Lady’s
lace, Laceflowe

24. Introduction contd…
A tall plant originating in
the Nile River Valley
which has large, rounded,
10-15 cm flower heads
made up of hundreds of
tiny, snow-white florets.
It is cultivated in North
India also.
The Seed of the plant
contains Xanthotoxin

25. Chemistry
Chemically, methoxsalen belongs to a
class of organic natural molecules known as
furanocoumarins. They consist of coumarin
annulated with furan. Xanthotoxin is 8-
methoxy psoralen or 8-methoxy 3’,2’-6,7
furocoumarin.

26. Chemistry contd…
O OO
OCH3
XANTHOTOXIN

27. Chemistry contd…
O O
O OO
COUMARIN
PSORALEN
O O
O ANGELICIN
O OO
O CH3
BERGAPTEN

28. Extraction and Purification
The pulverised coarse powder of the seed is used
for extraction with n-hexane.
Extraction is effected in 2-3 hrs and 3-4 washings
are done.
All the washings are combined and the solvent is
distilled off. The separated solid is dried and de
alkylated using HCl and methanol.

29. Extraction and Purification contd…
The de alkylated material contains
Xanthotoxol and Xanthotoxin
The de alkylated material is refluxed with
benzene for 2 hrs and cooled to room
temp. Xanthotoxol is separated
Xanthotoxin is crystallised from the
filtrate at 10-150C.

30. Testing methods
HPTLC
Mobile phase: Acetonitrile in water (35ml in 100ml
solution)
Detector wavelength: 254 nm
Flow rate: 1.5ml/minute

31. SYNTHESIS

32. Synthesis contd…

33. Synthesis contd…

34. Synthesis contd…
 The activation of dimethylallyl pyrophosphate
(DMAPP), produced via the mevalonate pathway, to
form a carbo-cation via the cleavage of the
diphosphates.
Once activated, the enzyme umbelliferone 6-
prenyltransferase catalyzes a C-alkylation between
DMAPP and umbelliferone at the activated position
ortho to the phenol, yielding demethylsuberosin. This
is then followed by a hydroxylation catalyzed by the
enzyme marmesin synthase to yield marmesin.
Another hydroxylation is catalyzed by psoralen
synthase to yield psoralen. A third hydroxylation by the
enzyme psoralen 8-monooxygenase yields xanthotoxol
which is followed by a methylation via the enzyme
xanthotoxol O-methyltransferase and S-adenosyl

35. BIOLOGICALACTIONS
Photosensitisation effect: when irradiated to
long wave length UV radiation
Killing bacteria: upon irradiation
Formation of mutants: Mutagenic effect is seen
in E Coli and Sarcina lutea
Inactivation of tumour cells
Inactivation of viruses

36. Properties and Uses
Used to treat psoriasis, eczema, vitiligo, and
some cutaneous Lymphomas in conjunction
with exposing the skin to sunlight.
Tonic, carminative and diuretic
Relaxes smooth muscles
Useful in kidney calculi and for angina pectoris
In formulations of sun-tan lotions
To increase the tolerance of sunlight

37. REFERNCES
 Pharmacognosy and pharmacobiotechnology
by Ashutoshkar, revised expanded 2nd edition
 Plant biosynthesis by Dr.S.S.Khadabadi
,S.L.Deore ,B.A.Baviskar
 Pharmacognosy &phytochemistry by
Vinod.D.Rangari ,volume 2