WELCOME
CONTENTS
COUMARINS
CLASSIFICATION
PSORALEN
XANTHOTOXIN
REFERNCES
COUMARINS
Coumarin (2H-chromen-2-
one) is a fragrant organic
chemical compound in
the benzopyrone chemical
class, which is...
CLASSIFICATION
1. Simple coumarins, such as coumarin
itself and dihydrocoumarin,
coumarin dihydroxycoumarin
2.Furocoumarins are formed in result of
furan ring and coumarin condensation in
6,7 positions (psoralen-derivatives) or 7,...
3. Pyranocoumarins are result of condensation of
coumarin with 2’2’-dimethylpyrane in positions 5,6
(dimethylxantyletin); ...
4. Benzocoumarins containing benzyl ring
condensed with coumarin in 3,4
positions occur Anacardiaceae and Rosaceae. Hy
dro...
PSORALEN
Synonym: Ficusin
Parent compound in
the family of
furanocoumarins
Umbeliferon
derivative
Linear furanocoumrin
BIOLOGICAL SOURCE
 Dried ripe fruits of
psoralea corylifolia
 Family :Leguminosae
 Content of the fruit:
◦ Psoralen
◦ I...
PSORALEA DERIVATIVES :
imperatoxin
xanthotoxin
bergapten
isomer :
angelicin
SOLUBILITY:
 Very soluble in chloroform
 Less soluble in alcohol
 Sparingly soluble in ether
 Insoluble in petroleum e...
STRUCTURE
OO O
7H-furo[3,2, benzopyran-7-one
Molecular formula :C11H6O3
CONSTITUTION
 Structure of psoralen is deduced by using
its degradation reaction
 It exhibits normal reactions of lacton...
ISOLATION
Dried fruits of Psoralea
corylifolea
Coarse
powder
To remove
essential oils
&resinous matter
present on outer
co...
Extracted with methanol
Methanolic extract (psoralen +other
coumarins +flavanoids)
Concentrate & dry
Chromatographed on si...
IDENTIFICATION TESTS
 1mg of psoralen in 5ml of ethanol+3 parts
of propylene glycol+43 parts of water
Blue fluoresence
 ...
1mg of Psoralen
in1ml of
methanol
Spotted on
silicagel-G plates
Plates are eluted in
benzene:chloroform
(98:2)
Dried plate...
USES
 In PUVA treatment for skin disease
◦ Psoriasis
◦ eczema
◦ vitiligo
 Recommended in the treatment of
alopecia
 Pso...
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
Gutterma...
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...
Xanthotoxin or Methoxsalen is extracted
from Ammi majus, a plant of the family
Umbelliferae. It modifies the way skin
cell...
Introduction contd…
A tall plant originating in
the Nile River Valley
which has large, rounded,
10-15 cm flower heads
made...
Chemistry
Chemically, methoxsalen belongs to a
class of organic natural molecules known as
furanocoumarins. They consist o...
Chemistry contd…
O OO
OCH3
XANTHOTOXIN
Chemistry contd…
O O
O OO
COUMARIN
PSORALEN
O O
O ANGELICIN
O OO
O CH3
BERGAPTEN
Extraction and Purification
The pulverised coarse powder of the seed is used
for extraction with n-hexane.
Extraction is e...
Extraction and Purification contd…
The de alkylated material contains
Xanthotoxol and Xanthotoxin
The de alkylated materia...
Testing methods
HPTLC
Mobile phase: Acetonitrile in water (35ml in 100ml
solution)
Detector wavelength: 254 nm
Flow rate: ...
SYNTHESIS
Synthesis contd…
Synthesis contd…
Synthesis contd…
 The activation of dimethylallyl pyrophosphate
(DMAPP), produced via the mevalonate pathway, to
form a c...
BIOLOGICALACTIONS
Photosensitisation effect: when irradiated to
long wave length UV radiation
Killing bacteria: upon irr...
Properties and Uses
Used to treat psoriasis, eczema, vitiligo, and
some cutaneous Lymphomas in conjunction
with exposing t...
REFERNCES
 Pharmacognosy and pharmacobiotechnology
by Ashutoshkar, revised expanded 2nd edition
 Plant biosynthesis by D...
Coumarins
Coumarins
Coumarins
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Transcript of "Coumarins"

  1. 1. WELCOME
  2. 2. CONTENTS COUMARINS CLASSIFICATION PSORALEN XANTHOTOXIN REFERNCES
  3. 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. 4. CLASSIFICATION 1. Simple coumarins, such as coumarin itself and dihydrocoumarin, coumarin dihydroxycoumarin
  5. 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. 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. 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
  8. 8. PSORALEN Synonym: Ficusin Parent compound in the family of furanocoumarins Umbeliferon derivative Linear furanocoumrin
  9. 9. 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
  10. 10. PSORALEA DERIVATIVES : imperatoxin xanthotoxin bergapten isomer : angelicin
  11. 11. SOLUBILITY:  Very soluble in chloroform  Less soluble in alcohol  Sparingly soluble in ether  Insoluble in petroleum ether
  12. 12. STRUCTURE OO O 7H-furo[3,2, benzopyran-7-one Molecular formula :C11H6O3
  13. 13. 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
  14. 14. 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
  15. 15. 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
  16. 16. 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
  17. 17. 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
  18. 18. 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
  19. 19. 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
  20. 20. 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
  21. 21. 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
  22. 22. 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
  23. 23. 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.
  24. 24. Chemistry contd… O OO OCH3 XANTHOTOXIN
  25. 25. Chemistry contd… O O O OO COUMARIN PSORALEN O O O ANGELICIN O OO O CH3 BERGAPTEN
  26. 26. 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.
  27. 27. 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.
  28. 28. Testing methods HPTLC Mobile phase: Acetonitrile in water (35ml in 100ml solution) Detector wavelength: 254 nm Flow rate: 1.5ml/minute
  29. 29. SYNTHESIS
  30. 30. Synthesis contd…
  31. 31. Synthesis contd…
  32. 32. 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
  33. 33. 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
  34. 34. 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
  35. 35. 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
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