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Drugs Containing Saponin
glycosides
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General Characters of Saponins
1.
Widely distributed in higher plants.
2.
Bitter, acrid taste & sternutatory (irritant to mucous
membranes).
3.
Form colloidal solutions in H
2
O
foam on shaking
lower of surface tension in aqueous solution.
4. Destroy RBCs blood haemolysis.
5. Toxic to cold- blood animals (fishes & frogs).
6.
Toxic by i.v. injection & harmless by oral
route.
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Chemical Characters
1.
O-glycosides
hydrolysis
aglycone
(sapogenin) + sugar moiety.
2.
Aglycone:
–
triterpenoidal(C-30) [mainly in Dicotyledons]
– steroidal(C-27) [mainly in Monocotyledons]
3. Sugar moiety:
– Often containuronic acids or acyl residues
.
– Usuallyglycosylation is at C-3.
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O
O
A B
C
D
1
2
3
4
56
7
89
10
11
12
13
1425
21
22
19
15
16
1718
20
1
2
3
45
6
7
89
10
11
12
13
1415
16
17
18
19
2021
22
23 24
25
26
27
E
Steroidal saponin aglycone Triterpenoidal saponin aglycone
3029
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Economical & Medicinal Importance
Economical uses
1. Cleaning industrial equipment & fine fabrics.
2. Powerful emulsifier.
3. Steroidal sapogenins used in semisynthesis of
cortisone & sex hormones.
Medicinal uses
1. Expectorant
2. Immunostimulant
3. Control of schistosomiasis snails
4. Hypoglycemic.
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Tests for Identification
1. Froth test:
1 ml of aqueous solution of saponin or plant
extract + shake persistent & voluminous
froth.
2. Haemolysis test:
Suspension of RBCs in normal saline + equal
volume of plant extract in normal saline +
shake gently
clear red solution indicating
heamolysis of RBCs (compared with blank ).
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Licorice Root
(RADIX GLYCYRRHIZAE)
ل رذ
-قزل
• Botanical origin: The dried peeled or
unpeeled roots and stolons of
Glycyrrhiza glabra L. and itsvarieties (Family Leguminosae =
Fabaceae).
•
Geographical Source:
Licorice isnative to the Mideterranean region,
as Spain, Italy, England, France,
Germany, U.S.A. ,Russia and Egypt.
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Licorice Powder
• Powdered licorice, is light yellow, having a faint
characteristic odor and a very sweetish taste,.
Powdered licorice is characterised by:
• Numerous fragments of fibresaccompanied by
crystal sheath.
• Dark yellow fragments of borded-pitted vessels.
• Prismatic crystals of calcium oxalate.
• Numerous starch granules, free or in parenchymacells, mostly simple, oval, round or fusiform, with
no striations but occasionally showing hilum• Cork may be present
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Licorice
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Active Constituents of Licorice
1- Saponins
Rhizomes & roots of licorice contains 2-6 of the triterpenoid
saponin Glycyrrhizin
Glycyrrhizic acid = Glycoside of
Glycyrrhetic acid
HO
COOH
Glycyrrhetic acid
aglycone)
O
3
Glycyrrhizin = mixture of K+ & Ca++ salts of Glycyrrhizic acid
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2-Major non-saponin constituents of
Licorice
Flavonoid glycosides: major liquiritin (flavanone).
Coumarins: herniarin & umbelliferone.
Others: asparagine, dihydrostigmasterol, glucose,
mannitol & starch.
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Licorice - Uses1. Expectorant & demulcent by stimulation of tracheal mucous
secretiondue to glycyrrhizin.
2. Antiinflamatory & adrenocorticotropic activity due to steroidal-
like activity of glycyrrhizin &/or glycyrrhetic acid.
3. Antihepatotoxic, antibacterial, antirheumatic, antitumour &
antiviral.
4. Used in treatment of gastric & duodenal ulcers by increasing the
rate of healing of gastric mucosa mainly due to liquiritin.
DGL = (Deglycyrrhizinated extract) licorice preparation with very
low of glycyrrhizin (< 1 ) used as antiulcer for hypertensive
patients.
5. Used in laxative formulations.
6. Used as sweetener (glycyrrhizin 50 times > sweet than sucrose)
& as flavoring agent to mask the bitter taste of some drugs as
aloe, quinine & others.
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ContraindicationsThe drug is contraindicated in patients with
hypertension, hypokalaemia, or chronic renal
insufficiency, and during pregnancy.
The drug should not be taken concurrently with
corticosteroid treatment .
Aldosterone-like effects: sodium and water retention,
potassium depletion, hypertension.
Side effects
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Ginseng RootSource
Roots of Panax quinquefolius (American
ginseng) & P. ginseng (Asian ginseng),
Araliaceae.
Contains a complex mixture oftriterpenoidal
saponins with a tetracyclic ( steroids) or
pentacyclic structure (in its cork).
Classification
Classified into 2 types:
1. Ginsenosides,
2. Panaxosides ( differ
from ginsenosides
in the sugar moiety).
Aerial partsoots
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Ginseng saponins
Ginsenosides:
1.Major saponins of ginseng (0.7-3
calculated as ginsenosides).
2.Aglycones of most ginsenosides have a
tetracyclic steroidal structure.
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Ginsenosides
HO
R
2
O
HO
CH
3
O R
1
HO
R
2
O
R
1
O
CH
3
20 S)-Protopanaxadiols
20 S)-Protopanaxatriols
Ginsenoside R
1
R
2
Rb
1
-glc 2-1)glc -glc 6-1)glc
Rb
2
-glc 2-1)glc -glc 6-1)arab
Rc -glc 2-1)glc -glc 2-1)arab
Rd -glc 2-1)glc -glc
Ginsenoside R
1
R
2
Re -glc 2-1)rha -glc
Rf -glc 2-1)glc -H
Rg
1
-glc -glc
Rg
2
-glc 2-1)rha -H
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Ginseng -Therapeutic uses
1- Adaptogenic (antistress): enhances body nonspecific resistance
to external stress (physical, chemical or biological).
2- Improves physical & mental performance e.g. learning, memory
& physical capabilities.
•
Tonic, stimulant, diuretic & carminative.
• Improves immune function & metabolism.
• Used in anemia, Hepatoprotective (ginsenosides), diabetes
(saponins and polysaccharides), insomnia, gastritis, Antitumor
(polyacetylenes and polysaccharides) & sexual impotence.
6. Contraindicated in case of hypertension & during pregnancy.
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Preparation
Ginseng is often processed in two forms:
-White ginseng (peeled).
-Red ginseng (unpeeled).
There are many types and grades of ginseng and ginseng extracts
depending on the source, age; andparts of the root used, and themethods of preparation
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فزوة
ب رذب
Horse chestnut Seed
(Semen Hippocastani)
Names :
Aesculus kernel
Origin
:Horse chestnut is the dried and fresh kernel ofAesculus hippocostanum L. Family Hippocastamaceae.
Constituents
-Saponin
referred to as escin (which is a complex mixtureof over 30 individual pentacyclic triterpene diester
glycosides) is regarded as the main active constituent; α
and β-escin are the major glycosides.
-Flavones, caumarins and tannins
are also present.
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Horse-chestnut demonstrates anti-edema and anti-
inflammatory effects due to saponin content. Escin
stimulates the release of corticosteroids necessary for
the anti-inflammatory activity. Antioxidant ,
hypoglycemic and cyto-toxic activities were also
reported and attributed to the saponin content of the
extract.
Uses
The flavonoids of the horse-chestnut leaves normalize
the pathologically increased permeability of blood
vessels and reduce the fragility of vessel walls, whereas
their coumarins content, being a vitamin K antagonist,
inhibits prothrombin production.
Horse-chestnut has been used for the treatment of
varicose veins, haemorrhoids, diarrhea, fever and
enlargement of the prostate gland.
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DRUGS CONTAININGFLAVONOID GLYCOSIDES
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Flavonoids’ Chemistry
Variety of structural forms
Free aglycones or glycosides
Skeleton contains 15 carbon atoms:
C6-C3-C6 [2 phenyl rings linked by a
three-carbon chain = diphenyl propane
derivatives].
*** Flavonoids give yellow color with
alkali as well as with aluminium
chloride.
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Flavonoids-Chemistry
O
A
B
Ring A
Ring B
Pyran ring
O
1
2
3
45
6
7
8 1'
2'
3'
4'
5'
6'
C
H
2
CH
2
H
2
C
A
B
Diphenyl propane skeleton
C6-C3-C6
Flavonoid skeleton
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Buchu Leaves
Origin of The Pant:
Buchu is the dired leaves of Barosma betulina
Family Rutaceae . Known as short buchu,
round buchu or diosma.
Origin of the name:
Buchu is a Zulu name of the drug. Barosma
refers to the heavy odor of the leaves.
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Buchu Leaves
Constituents:
1. Crystalline rhamnoglycoside diosmin
(flavone glycoside),found as sphero-
crystals (in the epidermal cells) and
hesperidin.
2. Volatile oil which is contained in the
oil glands cotains up to 30%
diosphenol.
3. Mucilage which is deposited on the
inner walls of the epidermal cells.
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O
O
H
OH
OMe
Rh
1
-
6
Glc-O
Rutinose
Diosmetin
Diosmin
7
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Uses:
1- Disinfectant to urinary tract , excretedby the kidney rendering the urine
antiseptic due to diosphenol.
2- Diuretic and Diaphoretic due to
diosphenol.
3-Diosmin is used to treat peripheral
vascular disorders (capillary fragility)
just like varicose veins and piles
(hemorrhoids).
Crataegus Fruits
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Crataegus Fruits
(Fructus Crataegi, Hawthorn)
ل روزعسد
Names: Hawthorn berry, Crataegus fruits, Fructus
oxycanthae
Origin:
Hawthorn berry consists of the dried fruits ofCrataegus monogyna
Jaq. ( = C. oxycantha L.), Family: Rosaceae.
Constituents:
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Uses and Actions:
It has been claimed that preparations of hawthorn berry
have been applied to the treatment of :•Early forms of cardiac insufficiency and angina pectoris.
•Nervous heart complications.
•Heart and circulatory disturbances.
•
Hypotension, and atherosclerosis.
Constituents:
1- Oligomeric procyanidins (1-3%).
2- Flavonoids (1-2%) named: Hyperoside, vitexin 2-rhamnoside
and rutin.3- Amines ( some with cardiotonic action).
4-Catechins and epicatechins.
5- Phenol-carboxylic acids (especially chlorogenic acid ).
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Ginkgo Leaf
Ginkgo leaf consists of the dried leaf of Ginkgo biloba (Ginkgoaceae).
1- The major constituents are flavonoids of which mono-, di-, and tri-
glycosides and coumaric acid esters that are based on the flavonols
kaempferol and quercetin dominate.
Major chemical constituents
2- Diterpene lactones ginkgolides A, B, C, J, and M and the
sesquiterpene lactone bilobalide
Medicinal uses
Extracts have been used for symptomatic treatment of mild to moderate
cerebrovascular insufficiency (memory deficit, disturbance in concentration,
depressive emotional condition, dizziness, and headache)
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1- Volatile oil.2- More than 20 alkamides, mostly isobutylamides
3-Caffeic acid ester derivatives present include echinacoside,
cynarin, and chicoric acid.
4-Polysaccharides
Active constituents
Preparations of Echinaceae are administered orally in supportivetherapy for colds and infections of the respiratory and urinary tract.
Beneficial effects in the treatment of these infections are generally
thought to be brought about by stimulation of the immune response
Medicinal uses:
Echinacea
Echinaceae consists of the fresh or dried roots
or whole herb of Echinacea angustifolia or,E.purpurea or E. pallida (Asteraceae).
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Drugs containing Cyanogenic
(Cyanogenetic or Cyanophore)
glycosides
Cyanogenic glycosides
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Cyanogenic glycosides
( Cyanogenetic or Cyanophore glycosides)
-hydroxynitrile derivatives = cyanohydrins.
Fairly unstable, stabilized by -D-linked sugar chains with -D-glucose as first
sugar attached to the aglycone.
O-glycosides
hydrolysis
HCN gas.
Examples (Linseed & Bitter almond seed)
C
R
2
sugar-O
R
1
CN
General structure of cyanogenic glycosides
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•
Names
: Linseed,Flax Seed
• Origin
: Linseed is
the dried ripeseeds of Linum
usitatissimum
Family: Linaceae.
Linseed بذر لكتان
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Constituents• 30 to 40% of fixed oil. The oil is rich in
unsaturated fatty acids : oleic acid (39%),linoleic acid (15%) and a-linolenic acid (30-
60%).
Linoleic acid ( Omega-6- fatty acid), and
alinolenic acid
(Omega-3 fatty acids) are
essential fatty acids.
• 25% of protein.
• 3-6% of mucilage
• Small amount of a cyanogenic glycoside
(linamarin).
•
Unripe seeds contain starch but the ripe seeds
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Uses and actions• In folk medicine, decoction as demulcent in
acute or chronic gastritis.• Omega-3 fatty acidsare anti inflammatory.
Thus, used in rheumatoid arthritis and
psoriasis. They cause a significant reduction
of very low density lipoprotein (VLDL), andlow density lipoprotein (LDL). They may be
used to reduce the blood pressure
,
especially in hypercholesterolaemia
and
hypertension
. They offer protection against
angina
and thrombosis
as they reduce the
blood viscosity.
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• Cake is used inpoultices
forboils
and
carbuncles.
• As a laxative in habitual constipation, due to
its mucilage. (crushed seeds). The laxative
action is due to increase in the volume of the
intestinal bowel contents and stimulation of
peristalsis (bulk laxative).• Linseed is used as antitussive due to its
cyanogenic glycoside content.
Toxicity:
• Linseed is advisable with plenty of fluids
otherwise it may cause flatulence.
• Liberation of HCN.
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commercial importance of linseed
plant and seeds?
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Chemical tests
• Test for Cyanogenic glycosides:
Guignard’s paper test):
Crushed seeds in test tube moistened
with water covered with a piece of
cork having a sodium picrate paper
(yellow color), leave in a warm place for 30 min., HCN will be evolved
converting the yellow colored paper to
brick red color.
H
3
C
CH
3
C
O
CN
Glc
Linamarin
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Bitter almond seeds بذر لس لمز
Source
Kernels of bitter almond seeds (
Prunus amygdalus
var.
amara) , [Rosaceae] .
Constituent:
The kernel contains mainly Cyanogenic glycoside named
as Amygdalin
Hydrolysis
Amygdalin + emulsin enzyme benzaldehyde +HCN +
2 glucose.
Uses
Preparation of benzaldehyde (volatile oil of bitter
almond) which is used as sedative and
flavoring agent.
Peaches
Kernels of apricots
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Amygdalin-hydrolysis C
O
CN
Glc- 1 - 6)-Glc
H
gentiobiose)
Amygdalin
C
O
CN
Glc- 1 - 6)-Glc
C
O
CN
Glc
C
HO
CN
CHO
HCN
+ Glucose
Mandelonitrile
Prunasin
Amygdalin
Benzaldehyde
hydrolyase
Prunasin
hydrolyase
Mandelonitrile lyase
H
H
H
Gentiobiose)
Amygdalin
+ Glucose
+
Volatile oil of bitter almond)
Bitter almond
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Drugs containing Glycosinolates
(containing sulphor and
nitrogen)
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Drugs containing glycosinolates
• Black mustard seeds (Brassica nigra,
containing sinigrin glycoside).
• White mustard seeds ( Brassica alba,
containing sinalbin glycoside).
• The two drugs are mentioned under drugs
containing volatile oils as sinigrin glycoside
on hydrolysis gives the volatile oilallylisothiocyanate.