Drugs Containing Saponin

glycosides

General Characters of Saponins

1. Widely distributed in higher plants.
2. Bitter, acrid taste & sternutatory (irritant to mucous
membranes).
3. Form colloidal solutions in H2O 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.

Chemical Characters
1. O-glycosides

hydrolysis
(sapogenin) + sugar moiety.

aglycone

2. Aglycone:
triterpenoidal (C-30) [mainly in Dicotyledons]
steroidal (C-27) [mainly in Monocotyledons]

3. Sugar moiety:
Often contain uronic acids or acyl residues.
Usually glycosylation is at C-3.

21

20

11
19
2

10

A
3

5
4

17
13 D

14
8

22
E

25

23

12

24
11

16
1

15

14

2
10

15
7

21

17

22

16

Steroidal saponin aglycone

18

20

13

25

30

26
19

18
12

29

27

Triterpenoidal saponin aglycone

Economical & Medicinal Importance

Economical uses
1. Cleaning industrial equipment & fine fabrics.
2. Powerful emulsifier.
3. Steroidal sapogenins used
cortisone & sex hormones.

in

Medicinal uses
1. Expectorant
2. Immunostimulant
3. Control of schistosomiasis snails
4. Hypoglycemic.

semisynthesis

of

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 ).

Licorice Root
(RADIX GLYCYRRHIZAE)
-

Botanical origin: The dried peeled or

unpeeled roots and stolons of
Glycyrrhiza glabra L. and its
varieties (Family Leguminosae =
Fabaceae).
Geographical Source: Licorice is
native to the Mideterranean region,
as Spain, Italy, England, France,
Germany, U.S.A. ,Russia and Egypt.

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 fibres accompanied by
crystal sheath.
Dark yellow fragments of borded-pitted vessels .
Prismatic crystals of calcium oxalate.
Numerous starch granules, free or in parenchyma
cells, mostly simple, oval, round or fusiform, with
no striations but occasionally showing hilum
Cork may be present

Licorice

Active Constituents of Licorice

1- Saponins
Rhizomes & roots of licorice contains 2-6 % of the triterpenoid
saponin Glycyrrhizin
Glycyrrhizin = mixture of K+ & Ca++ salts of Glycyrrhizic acid
COOH
O

Glycyrrhizic acid = Glycoside of

Glycyrrhetic acid

HO
Glycyrrhetic acid
(aglycone)

2-Major non-saponin constituents of

Licorice
Flavonoid glycosides: major liquiritin (flavanone).
Coumarins: herniarin & umbelliferone.
Others: asparagine, dihydrostigmasterol, glucose,
mannitol & starch.

Licorice - Uses
1.

Expectorant & demulcent by stimulation of tracheal mucous

secretion due to glycyrrhizin.

2.

Antiinflamatory & adrenocorticotropic activity due to steroidallike 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.

Contraindications
The drug is contraindicated in
hypertension, hypokalaemia, or
insufficiency, and during pregnancy.

patients with
chronic renal

The drug should not be taken concurrently with

corticosteroid treatment.

Side effects
Aldosterone-like effects: sodium and water retention,
potassium depletion, hypertension.

Ginseng Root
Source
Roots of Panax quinquefolius (American
ginseng) & P. ginseng (Asian ginseng),
Araliaceae.
Contains a complex mixture of triterpenoidal
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).
Roots

Aerial parts

Ginseng saponins
Ginsenosides:
1.Major saponins of ginseng (0.7-3 %
calculated as ginsenosides).
2.Aglycones of most ginsenosides have a
tetracyclic steroidal structure.

Ginsenosides
HO

R2O

CH3
HO

R 1O

R2 O

CH3

HO
O R1

20(S)-Protopanaxadiols
Ginsenoside
Rb1
Rb2
Rc
Rd

R1

-glc (2-1)glc
-glc (2-1)glc
-glc (2-1)glc
-glc (2-1)glc

R2
-glc (6-1)glc
-glc (6-1)arab
-glc (2-1)arab
-glc

20(S)-Protopanaxatriols
Ginsenoside
Re
Rf
Rg1
Rg2

R1

-glc (2-1)rha
-glc (2-1)glc
-glc
-glc (2-1)rha

R2
-glc
-H
-glc
-H

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.

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; and
parts of the root used, and the
methods of preparation

Horse chestnut Seed

(Semen Hippocastani)

Names :Aesculus kernel

Origin :Horse chestnut is the dried and fresh kernel of

Aesculus hippocostanum L. Family Hippocastamaceae.
Constituents
-Saponin referred to as escin (which is a complex mixture
of over 30 individual pentacyclic triterpene diester
glycosides) is regarded as the main active constituent;
and -escin are the major glycosides.
-Flavones, caumarins and tannins are also present.

Uses
Horse-chestnut demonstrates anti-edema and antiinflammatory 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.
Horse-chestnut has been used for the treatment of
varicose veins, haemorrhoids, diarrhea, fever and
enlargement of the prostate gland.
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.

DRUGS CONTAINING
FLAVONOID GLYCOSIDES

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.

Flavonoids-Chemistry
3'
2'
8

B
7

H2 C

1
O

C
H2

Diphenyl propane skeleton

C6-C3-C6

5
Ring A

B
6'

CH2

1'

4'

Ring B

4
Pyran ring

Flavonoid skeleton

5'

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.

Buchu Leaves
Constituents:
1. Crystalline rhamnoglycoside diosmin
(flavone glycoside),found as spherocrystals (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.

OMe
Rh1-6Glc-O

Rutinose
OH

Diosmetin
Diosmin

OH

Uses:
1- Disinfectant to urinary tract, excreted
by 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
(Fructus Crataegi, Hawthorn)

Names: Hawthorn berry, Crataegus fruits, Fructus
oxycanthae
Origin: Hawthorn berry consists of the dried fruits of Crataegus monogyna
Jaq. ( = C. oxycantha L.), Family: Rosaceae.

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 ).

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.

Ginkgo Leaf
Ginkgo leaf consists of the dried leaf of Ginkgo biloba (Ginkgoaceae).
Major chemical constituents

1- The major constituents are flavonoids of which mono-, di-, and triglycosides and coumaric acid esters that are based on the flavonols
kaempferol and quercetin dominate.
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)

Echinacea
Echinaceae consists of the fresh or dried roots
or whole herb of Echinacea angustifolia or,
E.purpurea or E. pallida (Asteraceae).
Active constituents
1- Volatile oil.
2- More than 20 alkamides, mostly isobutylamides
3-Caffeic acid ester derivatives present include echinacoside,
cynarin, and chicoric acid.
4-Polysaccharides
Medicinal uses:

Preparations of Echinaceae are administered orally in supportive

therapy 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

Drugs containing Cyanogenic

(Cyanogenetic or Cyanophore)
glycosides

Cyanogenic glycosides
( Cyanogenetic or Cyanophore glycosides)
CN

sugar-O

R1

R2

General structure of cyanogenic 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)

Linseed

Names:
Linseed,
Flax Seed
Origin: Linseed is
the
dried
ripe
seeds of Linum

usitatissimum

Family: Linaceae.

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 (3060%).
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

 In folk medicine,
decoction
as demulcent in
Uses and
actions
acute or chronic gastritis.
Omega-3 fatty acids are anti-inflammatory.
Thus, used in rheumatoid arthritis and
psoriasis. They cause a significant reduction
of very low density lipoprotein (VLDL), and
low 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.

 Cake is used in poultices for boils 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.

Whats the economic and

commercial importance of linseed
plant and seeds?

H3C

Chemical tests

CN
C

CH3

Glc

Test for Cyanogenic glycosides: Linamarin

(Guignards 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.

Bitter almond seeds

Source

Kernels of bitter almond seeds (Prunus amygdalus var.

amara) , [Rosaceae] .

Constituent:
The kernel contains mainly Cyanogenic glycoside named
as Amygdalin

Peaches

Hydrolysis
Amygdalin + emulsin enzyme
2 glucose.

benzaldehyde +HCN +

Uses
Preparation of benzaldehyde (volatile oil of bitter
almond) which is used as sedative and
flavoring agent.

Kernels of apricots

Amygdalin-hydrolysis

CN
C
O

Glc-(1 - 6)-Glc
(gentiobiose)
Amygdalin

Bitter almond

CN

Amygdalin

Glc-(1 - 6)-Glc

hydrolyase

CN
C
+ Glucose

Glc

(Gentiobiose)

Prunasin

Amygdalin

Prunasin
hydrolyase
H

CHO

CN
C

Mandelonitrile lyase HO
HCN +

Benzaldehyde
(Volatile oil of bitter almond)

+ Glucose

Mandelonitrile

Drugs containing Glycosinolates

(containing sulphor and
nitrogen)

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 oil
allylisothiocyanate.