pharmacognosy

3rd stage/1stterm

Saponin Glycosides
&
Flavonoid Glycosides

Dr. Zahraa Shubber

Lec .6
Saponins are a group of glycosides which is widely distributed in
the higher plants.
The aglycones of this glycosides are referred to as sapogenins.
This group of plants glycosides have two common
characteristics:
1. They foam in aqueous solution upon shaking, therefore they are
called saponin (from latin: sapo,soap)
2. They cause hemolysis of red blood cells when injected into blood
stream, but when taken by mouth saponins are comparatively
harmless.
Plants materials containing saponins have long been used
in many parts of the world for their detergent properties
and as fish poisons.

Much of the research conducted on the saponin-

containing plants was used to discover precursors for
steroid hormones as cortisone.
This substance was originally isolated from the adrenal
cortex and later synthesized from certain bile acids of the
cattles.
Since animal sources are in limited supply, so many
investigations had been performed and the most important
plant steroid for the partial synthesis of steroid hormones
are: diosgenin, botogenin, hecogenin, gitogenin,
sarsapogenin and smilagenin
Some of our valuable food materials contain significant
amount of saponins eg. Beans, lentils , ‫ﻋﺪس‬soybeans,
spinach and oats . ‫اﻟﺸﻮﻓﺎن‬
Toxicity is minimized during ingestion by low
absorption and by hydrolysis.
According to the structure of the aglycon or sapogenin,
saponins can be classified into either

1. Neutral saponins: steroidal commonly tetracyclic

triterpinoids C27.
2. Acid saponins: are pentacyclic triterpenoid C30.

Both types of saponins have the glycosidic linkage at

position 3.
Steroida triterpenoid Pentacyclic triterpenoid
The steroidal saponins are less widely distributed in
nature than pentacyclic triterpenoid type.

Steroidal saponins are of great pharmaceutical importance

because of their relationship to compounds such as the sex
hormones, cortisone, vitamin D and cardiac glycosides.
Medicinal importance of saponins:
1. The steroidal saponins are structurally related to modern
synthetic compounds that have a therapeutic significance,
such as adrenocortecoids and the sex hormones. So, they
are a suitable precursors in the partial synthesis of these
hormones, e.g., Diosgenin (sapogenins) isolated from the
rhizome of Dioscoria species.
2. Saponins increase the rate of absorption of many
pharmacological active substances (e.g., cardiac
glycosides).
3. Many saponin-containing drugs are used as expectorants
(e.g., Ipeca, Senaga and liquorice) as their contents of
saponins stimulate bronchial secretion and also activate the
ciliary epithelium of the bronchi.
4. The triterpenoidal saponin glycoside, glycyrrhizin, is the
main sweet principle of liquorice.
5. Beside being a valuable flavouring and sweetening agent,
liquorice has demulcent, expectorant and antispasmodic
action. All these activities attributed to the saponin,
glycyrrhizin.
6. Recently, glycyrrhizin was shown to be effectively in
gastric ulcer treatment and have a cortisone like action in
rheumatic arthritis and other inflammatory diseases.
Biosynthesis:
the pathway may be considered to be the same for both types
and involved a head to tail coupling of acetate units.
Drugs containing saponin glycosides:
1. Glycyrrhiza (licorice root)
Is the dried rhizome and roots of Glycyrrhiza glabra
(Fam: Fabaceae).
Glycyrrhiza is of greek origin and means sweet root,
glabra means smooth.
Glycyrrhiza contains saponin like glycoside, glycyrrhizin
(glycyrrhizic acid) which is 50 times as sweet as sugar.
 Upon hydrolysis, the glycoside loses its sweet taste and
it converted to the aglycon glycyrrhizic acid plus two
molecules of glucuronic acid. Other constituents include
flavonoid glycosides.
Glycyrrhetic acid
Uses:
Glycyrrhiza possesses demulcent and expectorant
properties.
It's used as flavoring agent and masks the taste of bitter
drugs such as aloe and ammonium chlorid.
 Commercially licorice is added to chewing gums,
chocolate candy, cigarettes, smoking mixture, chewing
tobacco, its added to beer, it increases foaminess.
glycyrrhetic acid is utilized for its anti-inflammatory
properties in dermatogical practice and licorice root extract
is employed in the treatment of peptic ulcer and
Addisons disease.
2. Ginseng
Is the root of the perennial herbs Panax quinquefolius
and Panax ginseng (Fam: Araliaceae).
Ginseng contains a complex mixture of triterpenoid
saponins that can be either steroidal Triterpenes or
pentacyclic related to oleanoic acid.
These glycosides include: ginsenosides with a steroidal
triterpene aglycone, and panaxosides.
Ginseng has tonic, stimulant, diuretics and carminative
properties.
it has antistress activity and also act on central nervous
system and endocrine secretions.
 its employed in the treatment of anemia, diabetes,
insomnia, gastritis and sexual impotence.
 Flavonoid Glycosides
Flavonoid is one of the largest class of naturally
occurring plant products, they present either in the free
state or as their respective glycosides.
 According to their name, they are usually yellow-
coloured compounds (flavous is a latin word yellow
colour).
Flavonoids are found in fruits, vegetables, grains, bark,
roots, stems, flowers, tea and wine.
 These natural products were known for their beneficial
effects on health long before flavonoids were isolated as
the effective compounds.
All derived from the same parent nucleus, 2-phenyl-
benzopyran (flavan), thus they have a basic C-15
skeleton.
According to the oxidation level of central pyran ring, they
can be classified into: flavones, flavonols, , isoflavones,
flavanones, and anthocyanidins.
In certain specific instances either the 6-membered
heterocyclic ring (pyrones) is replaced by a 5 membered
heterocyclic ring (aurones) or exists in an open-chain
isomeric form (chalcones).
Chalcones, have no central pyrone ring, so they are not
true flavonoidal compounds.
Aurones are oxidized forms that are obtained by
enzymatic oxidation. they have five membered pyrone
ring.
Properties of flavonoids:
Flavonoidal glycosides are soluble in water and alcohol.
Ethylacetate is the solvent of choice for the extraction of
flavonoids from aqueous solution.
 Flavonoids dissolve in alkalis give intense yellow color
solution, on the addition of acid become colorless.
Flavonoids exhibit strong fluorescence under UV light.
Flavonoids biosynthesis is derived from shikimate
pathways.
Examples of flavonoid glycosides:
1. Diosmin: flavone glycoside
Occurance: Barosma crenulata F. Rutaceae.
It has diuretic and diaphoretic action.
Upon hydrolysis, diosmin yields rhamnose, glucose
and diosmetin.
2. Rutin and quercetrin: are examples of flavonol
glycosides
a. Rutin occurs in the leaves of buckwheat.
 It is the 3-rhamnoglucoside (called rutinose) of the genin
quercitin.
 It gives on hydrolysis the aglycone (quercitin) beside one
molecule of glucose, and one molecule of rhamnose.
 Rutin is used to decrease capillary fragility.
b. Quercitrin
is quercitin 3-O-rhamnoside.
It occurs in the bark of Quercus tinctoria.
Quercitrin yield upon acid hydrolysis rhamnose and
quercetin.
The aglycone quercetin has a diuretic action.
3. Hesperidin: it is an example of flavanones. It is the main
flavonoidal glycoside of citrus fruits.
Upon hydrolysis by acid, hesperidin gives rhamnose,
glucose and hesperitin.
Uses: Hesperidin is necessary for absorption and
retention of vit C that lead to decrease capillary fragility.
4. Silymarin
The leaves and fruits of Silybum marianum family
Compositae contain silymarin (silybin).
Uses:
1. Silymarin is a very effective lipotropic and hepato
protective therapy.
2. It is a free radical scavenger.
3. Supportive treatment of acute and chronic alcoholic
poisoning and toxin induce hepatitis.
4. It is used for treatment of liver cirrhosis
caused by plant toxins (mushroom),
silymarin is applied as
Intravenous injection.
Thank you