Glycosides are compounds containing a carbohydrate and a noncarbohydrate residue in the same molecule. The carbohydrate residue is attached by an acetal linkage at carbon atom 1 to a noncarbohydrate residue or AGLYCONE. The nonsugar component is known as the AGLYCONE. The sugar component is called the GLYCONE.

1. SAPONINS WITH
BIOLOGICAL &
PHARMACOLOGICAL
ACTIONS
STEROIDS & TRITERPENOID
SAPONINS

2. PRESENTERS
Nimra Noor ………………PHRM51F20R027
Sadaf Raza …...……………PHRM51F20R028
Zaima Imran ………………PHRM51F20R029
[5TH SEMESTER, Fall , 2022]
 Presented to;
Sir Dr. Shahid Rasool, College of Pharmacy, UOS

3. Introduction
Glycosides are compounds containing a carbohydrate and a noncarbohydrate residue
in the same molecule.
The carbohydrate residue is attached by an acetal linkage at carbon atom 1 to a
noncarbohydrate residue or AGLYCONE.
The nonsugar component is known as the AGLYCONE. The sugar component is called
the GLYCONE.
An example is the methyl glucoside formed when a solution of glucose in boiling methyl
alcohol is treated with 0.5% HCl as a catalyst.
The aglycone may be methyl alcohol, glycerol, a sterol, a phenol, etc.

4. CLASSIFICATION OF GLYCOSIDES
When the chemical nature of the aglycone group is used as the basis of systematization,
the classification is as follows:

5. Saponins
 Saponins consist of a polycyclic aglycones
attached to one or more sugar side chains. The
aglycone part, which is also called sapogenin, is
either steroid (C27) or a triterpene (C30).
 Saponins are glycosides with foaming
characteristics. The foaming ability of saponins
is caused by the combination of a hydrophobic
(fat-soluble) sapogenin and a hydrophilic (water-
soluble) sugar part.
 Saponins have a bitter taste. Some saponins are
toxic and are known as sapotoxin.

6. SOURCES :
 Saponins are phytochemicals which can be
found in most vegetables, beans and herbs.
 The best known sources of saponins are
peas, soybeans, and some herbs with names
indicating foaming properties such as
soapwort, saoproot, soapbark and soapberry.
 Commercial saponins are extracted mainly
from Yucca schidigera and Quillaja
saponaria.

7. CLASSIFICATION
SAPONIN GLYCOSIDES
Saponin glycosides are divided into 2 types based on the chemical structure of their
aglycones (sapogenins). The so-called NEUTRAL saponins are derivatives of
STEROIDS with spiroketal side chains. The ACID saponins possess triterpenoid
structures.

8. BIOSYNTHESIS
The main pathway leading to both types of sapogenins is similar
and involves the head-to-tail coupling of acetate units.
However, a branch occurs, after the formation of the
triterpenoid hydrocarbon, squalene, that leads to steroids in one
direction and to cyclic triterpenoids in the other.

9. BIOLOGICAL ACTION OF
SAPONINS
 Cholesterol reduction: Saponins bind with bile salt and
cholesterol in the intestinal tract. Bile salts form small micelles
with cholesterol facilitating its absorption. Saponins cause a
reduction of blood cholesterol by preventing its re-absorption
also called "bile acid sequestrants".
 Immunity booster: Plants produce saponins to fight infections
by parasites. When ingested by humans, saponins also seem to
help our immune system and to protect against viruses and
bacteria.Saponins have the ability to bind with pathogens
entering the body forming molecules too large to be absorbed
through the intestional wall. These pathogen molecules are then
carried through the digestive system, forcing them to be
eliminated.
 Saponins also relieve stress from the body's vital immune system.
This enables the body's natural immune factors and antibodies to
be more efficient in combatting low grade inflammation that is
so very important in reducing progressive heart disease.

10.  Nonsystemic : Saponin molecules are "nonsystemic", meaning
they do all their work within the intestinal tract and do not enter
the rest of the body. Therefore, damaging side effects to the liver
and other vital organs cannot take place. Saponins breaks down
and removes impacted rubber-like matter on the colon walls and
act favorably on flora organisms in the intestines, encouraging
growth of friendly bacteria and decreasing harmful bacteria. This
healthy balance triggers the body's own natural immune system
to help eliminate frequent bacterial and fungal infections as well
as constipation and digestive disorders.
 protoplasmic poison: If it is absorbed; is a protoplasmic
poison. In its excretion it irritates the bronchial mucous
membrane, and in poisoning produced from it, digitalis is
indicated, as it is antagonistic to Saponin.

11.  Reduce cancer risk: Studies have shown that saponins can lower
the risk of human cancers, by preventing cancer cells from
growing. Saponins seem to react with the cholesterol rich
membranes of cancer cells, thereby limiting their growth and
viability. Roa and colleagues found that saponins may help to
prevent colon cancer and as shown in their article "Saponins as
anti-carcinogens" published in The Journal of Nutrition (1995,
125, 717s-724S). Some studies have shown that saponins can
cause apoptosis of leukemia cells by inducing mitotic arrest.
 Reduce bone loss: Studies with ovariectomized induced rats have
shown that some saponins, such as the steroidal saponins from
Anemarrhena asphodeloides, a Chinese herb, have a protective
role on bone loss.
 Antioxidant: The non-sugar part of saponins have also a direct
antioxidant activity, which may results in other benefits such as
reduced risk of cancer and heart diseases.

12. STEROID SAPONINS

13. Dioscorea
Common Name :Wild Yam
Botanical Names : A number of diocorea species
have been researched including:
Dioscorea villosa
Dioscorea bulbifera
Dioscorea batatas
Dioscorea alata

14. Part Used : Root
Constituents : Saponin Diosgenin Diosgenin
is a steroidal saponin, which is extracted
from the root of dioscorea. Other plant
steroids include hecogenin and tigogenin.

15. Tigogenin
Hecogenin

16. Biological &Pharmacological Actions
Research Update
 Dioscorea is a yam steroid extract used in
commercial steroid synthesis and consumed
by people.
 Dioscorea alata feeding exhibited its
antioxidative effects including alleviating
lipid peroxidation, and oxidative stress.
 Antioxidant activity of dioscorea and
dehydroepiandrosterone (DHEA) in older
humans is established.

17.  Diosgenin has an obvious antitumor
activity on S-180, HepA, U14 transplant
mice in vivo and L929, HeLa, MCF cells in
vitro.
(Chung S, Nelson-White T, Eskelson C, Watson RR. University of Arizona, School of Medicine, Tucson)

18. Fenugreek
 Botanical Name: Foenum-graecum (LINN.)
Family: Leguminosae
 Synonyms: Bird's Foot. Greek Hay-seed.
 Habitat: North Africa, India, cultivated
worldwide.
 Part Used: Seeds.
 Constituents:
 Volatile oil, containing3-hydroxy-4, 5-dimethyl-2-
furanone, dihydrobenzofuran, dihydroactinidiolide,
muurolene, elemene, selinene
 Alkaloids, including trigonelline, gentianine and
carpaine
 Saponins, based mainly on the sapogenins
diosgenin and its isomer yamogenin, gitogenin and
tigogenin
 Flavonoids, including vitexin and its glycosides
and esters, isovitexin, orientin, vicenins l and 2,
quercetin and luteolin
 Mucilage; mostly a galactomannan
 Actions: Expectorant, demulcent, anti-
inflammatory, anti-spasmodic, , hypotensive.

19. Biological &Pharmacological Actions
Research Update
 In Cairo it is used under the name of Helba. This is an Egyptian preparation,
made by soaking the seeds in water till they swell into a thick paste. Said to be
equal to quinine in preventing fevers; is comforting to the stomach and has
been utilized for diabetes.
 Alcoholic extracts of seeds are employed in the preparation of emollient
cataplasms, ointments and plasters.
 The decoction of 1 OZ. seeds to 1 pint water give a strong mucilage, which is
emollient is used internally in inflamed conditions of the stomach and
intestines.
 Externally it is used as a poultice for abscesses, boils, carbuncles, etc.
 It can be employed as a substitute for cod-liver oil in rickets, anaemia,
debility following infectious diseases.
 The ground seeds are used also to give a maple-flavouring to confectionery.
The powder is also employed as a spice in curry.
 It has a powerful odour of coumarin and is largely used for flavouring cattle
foods and to make damaged hay palatable.
 In India the fresh plant is employed as an esculent.
 Fenugreek seeds help balance blood sugar in diabetics. Fenugreek may also
have beneficial effects on triglycerides.

20. Ginseng
 Botanical: Panax quinquefolium (LINN.)
Family: N.O. Araliaceae
 Synonyms: Aralia quinquefolia. Five Fingers. Tartar Root. Red Berry. Man's
Health.
 Part Used Root.
 Habitat Ginseng is distinguished as Asiatic or Chinese Ginseng. It is a native
of Manchuria, Chinese Tartary and other parts of eastern Asia, and is largely
cultivated there as well as in Korea and Japan.
 Constituents A large amount of starch and gum, some resin, a very small
amount of volatile oil and the peculiar sweetish body, Panaquilon. This occurs
as a yellow powder, precipitating with water a white, amorphous substance,
which has been called Panacon.

21. Biological &Pharmacological Actions
Research Update
 In China, used particularly for dyspepsia, vomiting and nervous disorders. A decoction of 1/2
oz. of the root, boiled in tea or soup and taken every morning, is commonly held a remedy for
constipation and other diseases.
 In Western medicine, it is considered a mild stomachic tonic and stimulant, useful in loss of
appetite and in digestive affections that arise from mental and nervous exhaustion.
 Serum total cholesterol (TC), triglyceride (TG), low density lipoprotein (LDL) levels were
decreased by administration of ginseng extract for 8 weeks (6g per day), however, high density
lipoprotein (HDL) was increased. These findings support scientific claims that ginseng has the
hypolipidemic potential.
 Have potential in the prevention and treatment of diseases of the heart and circulatory system.
For instance, they inhibit the formation of lipid peroxides (fat oxidation) in cardiac muscle or in
the liver, they influence the function of enzymes contained in them, they decrease blood
coagulation, cholesterol, and sugar levels in blood, and they stimulate the immune system.
 Ginseng and Cognitive functioning :Various tests of mental performance were carried out under
double-blind conditions. A favorable effect of ginseng was observed in attention, mental
arithmetic, logical deduction, and auditory reaction time.
 Adaptogen : Improvement in energy, vitality, enjoyment, mental clarity & wellbeing, etc
 Also used as aphrodisiac.

22. Alfalfa
 Botanical Name: Foenum-graecum (LINN.)
 Family: Leguminosae
 Common Names: Alfalfa, Lucerne, Jatt, Kaba Yonca, Yonja
 Part Used: Whole plant Parts Used: Leaves - Aerial parts - sprouting seeds
 Constituents: A good source of protein, it contains up to 50% in addition
to having a good amount of beta carotene, octacosanol, and chlorophyll.
Contains amino acids, saponins, isoflavins, sugars, sterols, acids, minerals (Ca,
K, P, Mg, Fe, Zn, Cu), coumarins, alkaloids, porphyrins, and vitamins (A, B1,
B6, B12, C, D, E, K, niacin, biotin, folic acid, pantothenic acid).
 Actions: Nutrition/Cardiovascular/Astringent Tonic, Antifungal, Laxative,
Diuretic, Detoxifier, Anti-inflammatory, Febrifuge, Hepatoprotective,
Digestive, Nutritive, Anodyne, Anti-Arthritic

23. Biological &Pharmacological Actions
Research Update
 Alfalfa is a rich source of the minerals calcium, magnesium, phosphorous,
iron, potassium, and trace minerals. Specifically, it is one of the best sources
for protein and is very high in chlorophyll, carotene, the vitamins A, D, E, B-
6, K, and several digestive enzymes. This may be why it is said to help
reconstitute bone and when fresh, is beneficial for rickets. Alfalfa is one of
the most studied plants. The ashes of the leaves are 99% pure calcium..
 Alfalfa is used topically to help heal infections after surgery, or caused from
bed sores. It is commonly used for bladder infections.
 Known to reduce cholesterol and aid in preventing heart disease and stroke
 Alfalfa has been studied recently to for its ability to help diabetic patients who
do not respond well to insulin.

24.  High in chlorophyll and nutrients. Alkalizes the body
and detoxifies the body, especially the liver.
 Research suggests that it may inactivate dietary chemical
carcinogens in the liver and small intestine before they
have a chance to do the body any harm.
 Alfalfa reduce fatigue or muscle tenderness.
 It is also used to reduce the pain and inflammation of
rheumatism and arthritis.
 Alfalfa is used as an appetite stimulant, a vitality
augmenter (tonic), a digestive stimulant, for insomnia,
and to relax the nervous system."

25.  Promotes pituitary gland function.
 Contains an antifungus agent."
 The plant is a kidney tonic, prostatic tonic, reproductive tonic,
musculoskeletal tonic, glandular tonic and so forth.
 Alfalfa has traditionally been one of the best herbal treatments for arthritis,
gout, and rheumatism.
 Alfalfa has a proven cholesterol-lowering effect.
 Steriodal anti-inflammatory action is suggested by its content of plant
steriods.
 Alfalfa has also been shown to possess antibacterial action against gram-
negative bacteria (such as Salmonella typhi), and it contains atleast one protein
with known antitumor activity."

26. TRITERPENOID SAPONINS

27. Sarsaparilla
Botanical Name: Smilax officinalis
Family: Liliaceae
 Habitat: The plants are climbing vines native to tropical America andthe West Indies.
 Part Used: Root and rhizome.
 Constituents: Saponins, based on the aglycones sarsapogenin and smilagenin; the
major one being parillin (sarsaponin), with smilasaponin (smilacin) and sarsaparilloside
,sitosterol, stigmasterol and their glucosides.
 Uses: Alterative, anti-rheumatic, diuretic, diaphoretic.
 Preparations & Dosage: Decoction: pour l-2 teaspoonfuls of the root in a cup of
water, bring to the boil and simmer l0-l5 minutes. This should be drunk three times a
day.
 Tincture: take l-2 ml of the tincture three times a day.

28. Biological &Pharmacological Actions
Research Update
 Sarsaparilla is a widely applicable alterative. It may be used to
aid proper functioning of the body as a whole.
 It is particularly useful in scaling skin conditions such as
psoriasis, especially where there is much irritation.
 As part of a wider treatment for chronic rheumatism it should
be considered and is especially useful for rheumatoid arthritis.
 It has been shown that Sarsaparilla contains constituents with
properties that aid testosterone activity in the body.
 In secondary syphillis , cutaneous disease, and gouty
conditions.
 In chronic hepatic disorders.

29. Soap Tree
 Botanical Name: Quillaja saponaria
Family: Rosaceae
 Synonyms---Soap Bark, Panama Bark, Cullay.
 Part Used---Dried inner bark
 Habitat---Peru and Chile, and cultivated in Northern Hindustan.
 Constituents---Its chief constituent is saponin, which is a mixture of two
glucosides, quillaic acid and quillaia-sapotoxin. The latter is very poisonous
and possesses marked foam-producing properties. Calcium oxalate is also
present in the bark. The drug also contains cane-sugar and a non-toxic
modification of quillaic acid.
 Uses---It can be used as a stimulating expectorant. Quillaia bark is used in its
native country for washing clothes. For washing hair.
In the production of foam on non-alcoholic beverages, but its use in this way
is now generally prohibited by law.
 Doses of Quillaia Bark---As a decoction (5 parts to 200), adult-dose 1
tablespoonful.

30. Biological &Pharmacological Actions
Research Update
 Might be useful in cases of aortic disease with hypertrophy, its efficacy
depending on its action on the cardiac ganglia and muscle.
 Saponin when applied locally, is a powerful irritant, local anesthetic and
muscular poison.
 On account of its local irritation, when injected hypodermically it causes
intense pain; sneezing when applied to the nose; vomiting, diarrhoea and
gastroenteritis if taken in large doses internally.
 Locally applied, it paralyses motor and sensory nerves, and voluntary and
involuntary muscular fiber; in the voluntary muscles it produces a condition
of rigor mortis, and the muscular substance becomes brittle and structure-less.
 Saponin acts as an cathartic and a diuretic if it is absorbed; in its excretion it
irritates the bronchial mucous membrane, and is a protoplasmic poison.
 Powdered Soap Tree bark, 100 parts; alcohol, 400 parts; essence of Bergamot,
20 drops; mix. It is said to promote the growth of the hair.

31. Liquorice
 Botanical: Glycyrrhiza glabra
 Family: N.O. Leguminosae
 Part Used: Root.
 Constituents: The chief constituent of Liquorice root, to which
its sweet taste is due, is Glycyrrhizin (6- 8 %), obtainable in the
form of a sweet, white crystalline powder, consisting of the
calcium and potassium salts of glycyrrhizic acid.
The drug also contains sugar, starch, gum, protein, fat, resin,
asparagin, yellow colouring matter, and 0.03 of volatile oil.

33. Glycyrrhizinic acid is 50 times sweeter than sugar (sucrose). Upon hydrolysis, the
glycoside loses its sweet taste and is converted to the aglycone glycyrrhetinic acid plus
two molecules of glucuronic acid.
Glycyrrhetinic acid is a pentacyclic triterpenoid derivative of the beta-amyrin type.

34.  Glycyrrhetinic acid has expectorant and
antitussive properties (Chandler,1985).
Expectorants are used to decrease the viscosity
of tenacious mucus, or to increase the secretion
of mucus in dry irritant unproductive cough,
thereby, lubricating the air passages and making
coughing more productive.
 It is used considerably as a flavoring agent and
is frequently employed to mask the taste of
bitter drugs such as aloe, quinine etc.

35.  Peptic ulcer: Glycyrrhetinic acid inhibits the enzymes
(15-hydroxyprostaglandin dehydrogenase & delta 13-
prostaglandin) that metabolize the prostaglandins. This
causes an increased level of prostaglandins in the
digestive system. Prostaglandins inhibit gastric secretion
but stimulate pancreatic secretion and mucous secretion
in the intestines and markedly increase intestinal
motility. They also cause cell proliferation in the
stomach. The effect on gastric acid secretion,
promotion of mucous secretion and cell proliferation
shows why licorice has potential in treating peptic ulcer.

36.  Glycyrrhizin inhibits liver cell injury caused by
many chemicals and is used in the treatment of
chronic hepatitis and cirrhosis in Japan.
 It also inhibits the growth of several DNA and
RNA viruses, inactivating herpes simplex virus
particles irreversibly.

37.  A metabolite of glycyrrhetinic acid inhibits 11-beta-
hydroxysteroid dehydrogenase which converts ACTIVE
cortisol to INACTIVE cortisone in the kidneys. The
increased amounts of cortisol binds to the unprotected,
unspecific mineralocorticoid receptors and induce
sodium and fluid retention, hypokalaemia, hypertension
and inhibition of the RENIN-ANGIOTENSIN-
ALDOSTERONE system. Licorice should not be
given to patients with a known history of high blood
pressure
 A prolonged usage of licorice can also cause the
formation of cataracts.