Download Coumarin and phenoli..

Coumarins
and Related Compounds
• Coumarins are derivatives of benzo--pyrone, or lactones of
o-hydroxycinnamic acid (o-coumaric acid).
• The parent compound is coumarin, umbelliferone is the 7-OH
derivative of Coumarin.
• The glycoside of umbelliferone is called skimmin.
• These compounds are used to protect skin from UV light as
they absorb short wave length (280- 366 nm).
O
Coumarin
O
RO
R= H
R= Glc
O
O
Umbelliferone
Skimin
COOH
cis-cinnamic acid
OH
COOH
o-hydroxycinnamic acid
O
coumarin
O
Dicoumarol
• It is a phytoalexin (phytochemical antibiotics) formed due
to fungal effect on Melilotus officinalis (Red Clover), an
example of microbial transformation.
• It is a dimer of 4-hydroxycoumarin that is now produced
synthetically under the trade name of Dicoumarol.
• Uses: anticoagulant and rodenticide.
OH
O
OH
O
O
O
Furanocoumarins
• They are coumarin derivatives with additional
furan ring.
• Ammi
majus
contain
a
group
of
furanocoumarins, the parent compound is called
Psoralene.
• They are used for the treatment of psoriases and
leucodermia.
O
O
Psoralene
O
Furanochromones
• They are benzo--pyrone derivatives resist alkalis.
• Ammi visnaga contain furanochromones, the major is
Khellin.
• Khellin is a smooth muscle relaxant used as:
•
•
•
•
Bronchodilator.
Antispasmodic.
Renal colic.
Coronary vasodilator.
OCH3
O
O
O
OCH3
Khellin
Flavonoidal Glycosides
• Flavonoids are C-15 compounds (C6-C3-C6)
• Flavonoids, constitute one of the most diverse and
widespread group of natural products.
• They are one of the most important constituents of the
human diet. They are found in fruits, vegetables, nuts,
seeds, stems, flowers and common drinks e.g. tea.
• Flavonoids bind to a range of cellular receptor sites and
show a wide range of biological activities.
• They are classified into many groups based on the oxidation
level at ring C.
• They are benzo--pyrone derivatives, so not open by
alkalis.
• They are responsible for the colours of flowers and
fruits.
B
O
C
A
O
Flavone
O
Ring B
2
A
4
Ring B
2
A
3 OH
O
Flavonol
O
O
O
Flavanonol
2
4
3 Ring B
O
Isoflavone
4
2
3
4
O
Flavanone
+
Ring B
A
Ring B
A
3 OH
4
2
A
O
O 2 Ring B
A
3
3
O
Chalcone
4
Anthocyanin
General Tests of flavonoids:
• Yellow colour with Alkalis.
• Yellow colour with AlCl3.
• Blue colour with FeCl3.!!!
Biological properties:
-Antibacterial, antifungal, antioxidant, hepato-protective,
anti-inflammatory, cytotoxic, anti-tumor, anti-ulcer, for capillary
fragility (vasotonic, vasoprotective), spasmolytic
Pharmaceuticals: Remanal jel®, Daflon® tablets, Ruta C®,
Diosmin tablets,……..
1- Diosmin
• Source: Buchu leaves (Barosma betulina).
• Nature: Flavone glycoside.
• Uses: varicose veins (vasoprotective, for capillary fragility))
OH
1
Glc Rh O
O
7
OCH3
2
4
5
OH
O
2- Hesperidin
• Source: Citrus fruits.
• Nature: Flavanone glycoside.
• Uses: varicose veins (vasoprotective, for capillay fragility)
OH
Glu Rh O
O
OH
O
OCH3
3- Rutin
• Source: Ruta graveolens (family Rutaceae)
• Nature: Flavonol glycoside.
• Uses: Cold, Influenza, varicose veins (vasoprotective).
Essential for vit C absorption.
OH
HO
O
OH
O-Rh-Glc
OH
O
4- Genistein and Genistin
• Source: Andria spp. (Genistein)
Genista and Lupinus spp., Soy bean
• Nature: Isoflavone & it Glycoside.
• Uses: Estrogenic activity, antioxidant, anti-aging
RO
O
1
2
3
4
OH
O
OH
R= OH
Genistein
R= Glucose Genistin
5- Anthocyanidin
• Source: Grape and Berries.
• Nature: Anthocyanidins (aglycones), cyanins
(glycosides), color depend on PH of cell sap..
• Uses:
Antioxidant, coloring matter
OH
+
O
HO
OH
OH
6- Rotenone
• Source: Derris Roots.
• Nature: Isoflavanone derivatives.
• Uses: Insecticides (interfere with oxidative phosphorylation).
O
O
O
O
OMe
OMe
7- Amentoflavone
• Source: Ginkgo biloba,
• Nature: Bioflavones.
• Uses: Antioxidant, Enhance cerebral circulationDelaying diabetic cataract and Diabetic neuropathies.
HO
O
OH
5'
OH
O
HO
8''
OH
O
O
OH
Flavano-lignans
1- Silymarin
• Source: Silybum marianum.
• Nature:
• Condensation product of flavanone with hemilignans.
• Silymarin is a mixture of isomers the major isomer is Silybin.
• Uses:
• Very effective hepatoprotective and antihepatotoxic agent.
O
HO
O
O
OH
OH O
OH
OCH3
OH
Mechanism of Action of silymarin:
• Antioxidant, so protect liver cells from free radicals.
• Stimulate liver cell regeneration.
• Anti-fibrotic and anti-cirrhotic activity.
Lignans
1- Podophyllotoxin
• Source: Podophyllum Rhizomes.
• Nature:
• Lignan derivatives.
• Lignans are C18 compounds resulted from condensation of two
hemilignans C9.
OH
• Uses:
• Anticancer.
• Treatment of skin warts
O
O
O
O
H3CO
OCH3
OCH3
Etoposide
podophyllotoxin
(Semisynthetic derivative)
OH
O
O
O
Me
O
O
O
HO
OH
O
O
H3CO
O
OCH3
OCH3
O
O
O
MeO
OMe
OH
• Side Effects of podophyllotoxin:
• GIT upset, Nausea and Vomiting.
• Semisynthetic Derivatives:
• Etoposide: Lung and testicular cancer
• Teniposide: Leukaemia and brain cancer in
children.