drugs containing saponin glycosides

7/23/2019 Drugs Containing Saponin Glycosides

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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 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.



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.



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



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.



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)

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.



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



Licorice



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



2-Major non-saponin constituents of

Licorice

Flavonoid glycosides: major liquiritin (flavanone).

Coumarins: herniarin & umbelliferone.

Others: asparagine, dihydrostigmasterol, glucose,

mannitol & starch.



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.



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



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



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

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



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; andparts of the root used, and themethods of preparation



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.



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.



DRUGS CONTAININGFLAVONOID 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

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



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 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.



O

O

H

OH

OMe

Rh

1

-

6

Glc-O

Rutinose

Diosmetin

Diosmin

7



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



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:



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 ).



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)



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).

http://www.falconridgefarms.ca/images/products/EchRootFresh.jpg



Drugs containing Cyanogenic

(Cyanogenetic or Cyanophore)

glycosides

Cyanogenic glycosides



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



•

Names

: Linseed,Flax Seed

• Origin

: Linseed is

the dried ripeseeds of Linum

usitatissimum

Family: Linaceae.

Linseed بذر لكتان



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



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.



• 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.



commercial importance of linseed

plant and seeds?



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



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



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



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 oilallylisothiocyanate.

drugs containing saponin glycosides

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