coumarin glycosides and related compounds coumarins are derivatives of benzo- -pyrone, or lactones...
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Coumarin Glycosides Coumarin Glycosides and Related Compoundsand Related Compounds
Coumarins are Coumarins are derivatives of benzo-derivatives of benzo--pyrone-pyrone, or lactones of , or lactones of oo-hydroxycinnamic acid-hydroxycinnamic acid ( (oo-coumaric acid). -coumaric acid).
The parent compound is coumarin, umbelliferone is the 7-OH The parent compound is coumarin, umbelliferone is the 7-OH derivative of Coumrin.derivative of Coumrin.
The glycoside of umbelliferone is called skimmin.The glycoside of umbelliferone is called skimmin.
These compounds are used to protect skin from UV light as These compounds are used to protect skin from UV light as they absorb short wave length (280- 315 nm).they absorb short wave length (280- 315 nm).
O ORO
R= H UmbelliferoneR= Glc Skimin
O O
Coumarin
DicoumarolDicoumarolIt is a phytoalexin formed due to fungal effect on It is a phytoalexin formed due to fungal effect on Melilotus officinalisMelilotus officinalis (Red Clover) (Red Clover)
It is a dimer of 4-hydroxycoumarin that is now produced It is a dimer of 4-hydroxycoumarin that is now produced synthetically under the trade name of Dicoumarol.synthetically under the trade name of Dicoumarol.
Uses:Uses: anticoagulant anticoagulant and and rodenticiderodenticide..
O O
OH
O
OH
O
FuranocoumarinsFuranocoumarins
They are coumarin derivatives with additional They are coumarin derivatives with additional furan ring.furan ring.
Ammi majus contain a group of Ammi majus contain a group of furanocoumarins, the parent compound is called furanocoumarins, the parent compound is called Psoralene.Psoralene.
They are used for the treatment of psoriases and They are used for the treatment of psoriases and leucodermia.leucodermia.
O OO
Psoralene
FuranochromonesFuranochromonesThey are benzo-They are benzo--pyrone derivatives resist alkalis.-pyrone derivatives resist alkalis.
Ammi visnaga contain furanochromones, the major is Ammi visnaga contain furanochromones, the major is Khellin.Khellin.
Khellinis a smooth muscle relaxant used as:Khellinis a smooth muscle relaxant used as:Bronchodilator.Bronchodilator.
Antispasmodic.Antispasmodic.
Renal colic.Renal colic.
Coronary vasodilator.Coronary vasodilator.
O
O
O
OCH3
OCH3
Flavonoidal GlycosidesFlavonoidal GlycosidesFlavonoids are C-15 compounds.Flavonoids are C-15 compounds.
FlavonoidsFlavonoids, constitute one of the most diverse and , constitute one of the most diverse and widespread group of natural products. widespread group of natural products.
They are one of the most important constituents of the They are one of the most important constituents of the human diet. They are found in fruits, vegetables, nuts, human diet. They are found in fruits, vegetables, nuts, seeds, stems, flowers and common drinks e.g. tea.seeds, stems, flowers and common drinks e.g. tea.
Flavonoids bind to a range of cellular receptor sites and Flavonoids bind to a range of cellular receptor sites and show a show a wide range of biological activitieswide range of biological activities. .
They are classified into many groups based on the oxidation They are classified into many groups based on the oxidation level at ring C.level at ring C.
They are They are benzo-benzo--pyrone derivatives so not open by -pyrone derivatives so not open by alkalis.alkalis.
They are responsible for the colours of flowers and They are responsible for the colours of flowers and fruits.fruits.
O Ring B
O
3
2
4
O Ring B
OH
O
3
2
4
O Ring B
OH
O
3
2
4
O
Ring B
O
3
2
4
O Ring B
3
2
4
Ring B
O
3
2
4
+
AAA
A A A
FlavanoneFlavanonol
Flavone
Flavonol
Isoflavone Chalcone Anthocyanin
O
O
C
B
A
General Tests:General Tests:
Blue colour with FeClBlue colour with FeCl33..
Yellow colour with Alkalis.Yellow colour with Alkalis.
Yellow colour with AlClYellow colour with AlCl33..
1- Diosmin1- DiosminSource:Source: Buchu leaves.Buchu leaves.
Nature:Nature: Flavone glycoside.Flavone glycoside.
Uses:Uses: Diuretic- Diaphoretic- varicose veins (vasoprotective)Diuretic- Diaphoretic- varicose veins (vasoprotective)
O
O
OCH3
OH
OH
ORhGlc
2- Hesperidin2- HesperidinSource:Source: Citrus fruits.Citrus fruits.
Nature:Nature: Flavanone glycoside.Flavanone glycoside.
Uses:Uses: Diuretic- Diaphoretic- varicose veins (vasoprotective)Diuretic- Diaphoretic- varicose veins (vasoprotective)
O
O
OCH3
OH
OH
ORhGlu
3- Rutin3- RutinSource:Source: Ruta graveolens and Nicotiana tabacumRuta graveolens and Nicotiana tabacum
Nature:Nature: Flavonol glycoside.Flavonol glycoside.
Uses:Uses: Cold- Influenza- varicose veins (vasoprotective).Cold- Influenza- varicose veins (vasoprotective).
Essential for vit C absorption.Essential for vit C absorption.
O
O
OH
OH
OH
HO
O-Rh-Glc
4- Genistein and Genistin4- Genistein and GenistinSource:Source: Andria Andria spp. (Genistein)spp. (Genistein)
Genista Genista andand Lupinus Lupinus spp.spp.
Nature:Nature: Isoflavone & it Glycoside.Isoflavone & it Glycoside.
Uses:Uses: Estrogenic activity.Estrogenic activity.
O
OOH
RO
OH
R= OH GenisteinR= Glucose Genistin
5- Anthocyanidin5- AnthocyanidinSource:Source: Grape and BerriesGrape and Berries..
Nature:Nature: Anthocyanidins.Anthocyanidins.
Uses:Uses: Antioxidant.Antioxidant.
O OH
OH
OH
HO+
6- Rotenone6- RotenoneSource:Source: Derris Derris Roots.Roots.
Nature:Nature: Rotenoids (Isoflavone derivatives).Rotenoids (Isoflavone derivatives).
Uses:Uses: Insecticides.Insecticides.
OO
O
O
OMe
OMe
7- Amentoflavone7- AmentoflavoneSource:Source: Ginkgo bilobaGinkgo biloba..
Nature:Nature: Biflavones.Biflavones.
Uses:Uses: Uterine antispasmodic- Enhance cerebral circulation- Uterine antispasmodic- Enhance cerebral circulation- Delaying diabetic cataract and Diabetic Delaying diabetic cataract and Diabetic
neuropathies.neuropathies.
O
O
OH
OH
HO
OH
OH
HOO
O
5'
8''
Flavono-lignansFlavono-lignans1- Silymarin1- Silymarin
Source:Source: Silybum marianumSilybum marianum..
Nature:Nature: Condensation product of flavones with hemilignans.Condensation product of flavones with hemilignans.
Silymarin is a mixture of isomers the major isomer is Silybin.Silymarin is a mixture of isomers the major isomer is Silybin.
Uses:Uses: Very effective hepatoprotective and antihepatotoxic agent.Very effective hepatoprotective and antihepatotoxic agent.
O
OH
O
HO
OH
O
OOH
OCH3
OH
Mechanism of Action:Mechanism of Action:
Antioxidant so protect liver cells from free radicals.Antioxidant so protect liver cells from free radicals.
Stimulate liver cell regeneration.Stimulate liver cell regeneration.
Anti-fibrotic and anti-cirrhotic activity.Anti-fibrotic and anti-cirrhotic activity.
LignansLignans1- Podophyllotoxin1- Podophyllotoxin
Source:Source: Podophyllum Podophyllum Rhizomes.Rhizomes.
Nature:Nature: Lignan derivatives.Lignan derivatives.
Lignans are C18 compounds resulted from condensation of two Lignans are C18 compounds resulted from condensation of two hemilignans C9.hemilignans C9.
Uses:Uses: Anticancer.Anticancer.
O
O
O
OH
OCH3H3CO
OCH3
O
Side Effects:Side Effects:GIT upset, Nausea and Vomiting.GIT upset, Nausea and Vomiting.
Semisynthetic Derivatives:Semisynthetic Derivatives:Etoposide: Lung and testicular cancerEtoposide: Lung and testicular cancer
Teniposide: Leukaemia and brain cancer Teniposide: Leukaemia and brain cancer in children.in children.