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Coumarin Glycosides
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 Coumrin.
The glycoside of umbelliferone is called skimmin.
These compounds are used to protect skin from UV light as
they absorb short wave length (280- 315 nm).
O
Coumarin
O
RO
R= H
R= Glc
O
O
Umbelliferone
Skimin
Dicoumarol
It is a phytoalexin formed due to fungal effect on
Melilotus officinalis (Red Clover)
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.
Khellinis a smooth muscle relaxant used as:
Bronchodilator.
Antispasmodic.
Renal colic.
Coronary vasodilator.
OCH3
O
O
O
OCH3
Flavonoidal Glycosides
Flavonoids are C-15 compounds.
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
A
O
Flavonol
2
3
O
Isoflavone
3
4
Ring B
O
2
4
2
3
4
O
Flavanone
+
Ring B
A
Ring B
A
OH
O
Flavanonol
A
4
Ring B
2
OH
3
O
O
O 2 Ring B
A
3
3
O
Chalcone
4
Anthocyanin
General Tests:
Blue colour with FeCl3.
Yellow colour with Alkalis.
Yellow colour with AlCl3.
1- Diosmin
Source: Buchu leaves.
Nature: Flavone glycoside.
Uses: Diuretic- Diaphoretic- varicose veins (vasoprotective)
OH
Glc Rh O
O
OH
O
OCH 3
2- Hesperidin
Source: Citrus fruits.
Nature: Flavanone glycoside.
Uses: Diuretic- Diaphoretic- varicose veins (vasoprotective)
OH
Glu Rh O
O
OH
O
OCH3
3- Rutin
Source: Ruta graveolens and Nicotiana tabacum
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.
Nature: Isoflavone & it Glycoside.
Uses: Estrogenic activity.
RO
O
OH
O
OH
R= OH
Genistein
R= Glucose Genistin
5- Anthocyanidin
Source: Grape and Berries.
Nature: Anthocyanidins.
Uses: Antioxidant.
OH
+
O
HO
OH
OH
6- Rotenone
Source: Derris Roots.
Nature: Rotenoids (Isoflavone derivatives).
Uses: Insecticides.
O
O
O
O
OMe
OMe
7- Amentoflavone
Source: Ginkgo biloba.
Nature: Biflavones.
Uses: Uterine antispasmodic- Enhance cerebral circulationDelaying diabetic cataract and Diabetic neuropathies.
HO
O
OH
5'
OH
O
HO
8''
OH
O
O
OH
Flavono-lignans
1- Silymarin
Source: Silybum marianum.
Nature:
Condensation product of flavones 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
OCH 3
OH
Mechanism of Action:
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.
O
O
O
O
OCH3
H3CO
OCH3
Side Effects:
GIT upset, Nausea and Vomiting.
Semisynthetic Derivatives:
Etoposide: Lung and testicular cancer
Teniposide: Leukaemia and brain cancer in
children.