Saponin Glycosides

Mrs. S.G.Gurunani PLCP, Nagpur. 1

 Saponin Glycosides
 Group of organic compounds that form
persistent froth when shaken with
water.
 The word Sapo means Soap like.
 Saponins cause haemolysis of red blood
cells.
 On hydrolysis gives aglycone i.e
Sapogenin
 Sapogenins on acetylation gives
crystals
Mrs. S.G.Gurunani PLCP, Nagpur. 2
 Properties:
 Solublein water, alcohol and mixture of them.
 Form persistent froth with water.
 Used as detergent and emulsifying agents.
 Aglycones are called Sapogenin.
 Cause haemolysis of RBC’s if reach the blood.
 Form complex with cholesterol.
 Only small part absorbed when taken orally.
 Enhance the absorption of other drugs.
Mrs. S.G.Gurunani PLCP, Nagpur. 3
 Classification:
 According to the nature of the aglycone
saponins are classified into Steroidal and
Triterpenoidal saponins.

Sug-O
Sug-O
Tetracyclic Mrs. S.G.Gurunani PLCP, Nagpur.
Pentacyclic 4

Steroidal Saponins Triterpenoidal Saponins

They are C-27 with 5 methyl groups.
Less distributed in nature comparing to
Triterpenoidal saponins.
Used mainly as precursors for the partial
synthesis of sex hormones and corticosteroids.
Drugs containing Steroidal saponins such as:
Discoria species ------- Diosgenin
Liquorice ---------------Glycerrhizin
Shatavari ------------- Shatavarin

Mrs. S.G.Gurunani PLCP, Nagpur. 5

 Diosgenin

Mrs. S.G.Gurunani PLCP, Nagpur. 6

 COO-

Glc Glc O
Glycyrrhetic acid

Glycyrrhizinic acid

Glycyrrhizin
Mrs. S.G.Gurunani PLCP, Nagpur. 7
 Dioscorea
Synonym : Yam
Biological Source : It is the
dried underground roots and
tubers of Dioscorea
deltoidea,
D. Composita &
D.villosa.
Belonging to the family :
Dioscoreaceae
Geographical Source: USA ,
N.W Himalayas , Mrs. S.G.Gurunani PLCP, Nagpur. 8

cultivation in J& K
Constituents
Steroidal saponin : dioscin
Hydrolysis

Dioscin Diosgenin + 2 Rhamnose +

1 glucose
(4-6 % )

Yamogenin
Phytosterols, alkaloids, tannins, starch.

The sugar-free (aglycone), diosgenin is used for

the commercial synthesis of cortisone,
pregnenolone, progesterone, and other steroid
products.
Mrs. S.G.Gurunani PLCP, Nagpur. 9
Rhamnose

Glucose Diosgenin

Rhamnose

Mrs. S.G.Gurunani PLCP, Nagpur. 10

 Anti-spasmodic,
USES :
anti-inflammatory, anti-rheumatic,
diaphoretic, diuretic, tonic, expectorant
A starting material in synthesis of
Steroidal harmones
Dioscin
Coticosteroids
Dioscin Diosgenin 16-DPA Pregnenolone
Androsterones
19 Non steroids
Vitamins

Mrs. S.G.Gurunani PLCP, Nagpur. 11

Mrs. S.G.Gurunani PLCP, Nagpur. 12
Mrs. S.G.Gurunani PLCP, Nagpur. 13
 Steroidal Saponins

 They are C-27 with 5 methyl groups.

 Less distributed in nature compared to
Triterpenoidal saponins.
 Used mainly as precursors for the partial synthesis
of sex hormones and corticosteroids.
 Drugs containing Steroidal saponins such as:
 Dioscorea species Diosgenin
 Sarsaparilla Roots Sarsapogenin
Mrs. S.G.Gurunani PLCP, Nagpur. 14
 Ginseng Saponins
(Ginsenosides)
 Synonyms : Ninjin, pannag, panax
 Origin: Ginseng is the dried root of various species
of Panax, like P.ginseng (Korean ginseng), P.
japonica (Japanese ginseng) , P. notoginseng (Chinese
ginseng) and P. quinquefolium (American ginseng),
belonging to family araliaceae
 Geographical Source
It grows widely in India, Korea, china, and Russia.
Presently, ginseng is commercially cultivated in
Korea, China, Japan, Canada and United States of
America.

Mrs. S.G.Gurunani PLCP, Nagpur. 15

Panax indicates curve
all (Pan and axos), while
ginseng is derived from
Chinese words shen
sang, which stands for
manroot, because the
shape of the root
resembles the human
body.

Mrs. S.G.Gurunani PLCP, Nagpur. 16

Cultivation and collectionrequires
loam soil
clay loam or sandy

Seed propagation , in nursery beds altitudes from 100-800 metres

soil with high amount of
Transplanted into open fields potassium gives better result

Ripe seeds are collected from four year old plants.

After attaining sufficient growth, seedlings are dug up in the following May
and transplanted to permanent beds for next 3-5 years.

plants are harvested 3-5 years after transplantation between July to October

ginseng is obtained by removing the outer layers of the roots

Red ginseng is obtained by first steaming the roots and after that they are dried
But, removal of outer layers may lead to loss of active constituents.

Mrs. S.G.Gurunani PLCP, Nagpur. 17

Macroscopic Characters

Color : yellowish brown, white or red

Ginseng roots are tuberous corpulent roots.
They are translucent and possess the stem
scars.

Chemical Constituents
Ginsenosides ;
Panaxosides and
Chikusetsusaponin
Ginsenosides contain aglycone dammarol while
panaxosides have oleanolic acid as aglycone.
About 13 ginsenosides have been identified.
Panaxosides give oleanolic acid, panaxadiol and
Mrs. S.G.Gurunani PLCP, Nagpur. 18
panaxatriol on decomposition.
Nature: They are C-30 compounds
but they have typical Steroidal
skeleton.
Classification: a- Protopanaxdiols
b- Protopanaxtriols

Protopanaxdiols Protopanaxatrion

OH OH
Sug-O Sug-O

Sug-O Sug-O
O-Sug

Mrs. S.G.Gurunani PLCP, Nagpur. 19

Standards
Foreign organic ≥ 2.0%
matter
Total ash ≥ 4.2%
Acid insoluble ash ≥ 1.0%
Sulfated ash ≥ 12.0%
Alcohol soluble ≤ 14.0%
extractive

Mrs. S.G.Gurunani PLCP, Nagpur. 20

 Uses:
1.Ginseng is an immunomodulatory drug.
2.It increases the natural resistance (non- specific resistance)
and enhances the power to overcome the lines or exhaustion.
3.It has both stimulant and sedative properties.
4.It is used as aphrodisiac.
5.It is believed to be useful in adrenal and thyroid
dysfunctioning.
6.Ginseng was used for a number of ailments, like curing the
giddiness and prolonging life of elderly and diabetic persons.
7.It is given as demulcent and in gastritis and anemia.
8.Although, ginseng shows a low toxicity, long term use
leads to poisoning, similar to that of corticosteroids.
9.Ginseng extracts are also used externally in cosmetics.
Mrs. S.G.Gurunani PLCP, Nagpur. 21
Interactions:
Warfarin - INR
Anticoagulants, anti – platelets -  effect
Antidiabetes, insulin -  hypoglycemic effect
Drugs metabolized by CYP 3A4 – ginseng
inhibits enzyme
MAO inhibitors

Mrs. S.G.Gurunani PLCP, Nagpur. 22

 Fenugreek
Synonym: bird’s foot, Greek hay seed
Origin : seeds of Trigonella foenum -
graecum
( Fabaceae)
History :
The name fenugreek or foenum-graecum is
from Latin for "Greek hay". The plant's
similarity to wild clover has likely spawned
Its Swedish name: "bock horns klöver“
meaning: "ram's horn clover".
Fenugreek seeds are used as a medicinal in
Traditional Chinese Medicine under the
name
Hu Lu Ba, where they are considered to
warm and tonify kidneys, disperse cold and
alleviate pain
Mrs. S.G.Gurunani PLCP, Nagpur. 23
Constituent:
Fenugreek seeds are a rich source of the polysaccharide
galactomannan.
They are also a source of saponins ---diosgenin,
yamogenin, gitogenin, tigogenin, and neotigogens.
Other constituents ---- mucilage, volatile oils, and
alkaloids (pyridine alkaloid) ----choline and trigonelline.

Use: spice, source of diosgenin; lowers cholesterol,

blood
glucose, insulin, appetite stimulant and anticancer
galactagogue
- topical skin inflammation, muscle pain and gout
Note: Adverse effect causes hepatotoxicity, causes angioedema
( inhalation or ingestion of topical anesthesia

Mrs. S.G.Gurunani PLCP, Nagpur. 24

 Triterpenoidal Saponins
(Pentacyclic triterpenoid saponins)
 They are C-30 compounds.
 Much more distributed in nature.
 Have pentacyclic skeleton with 8 methyl groups.

Sug-O
Sug-O

Steroidal Saponins Mrs. S.G.Gurunani PLCP, Nagpur. Triterpenoidal Saponins 25

Mrs. S.G.Gurunani PLCP, Nagpur. 26
 Liquorice
 Synonym: Glycyrrhiza, liquorice root, glycyrrhize radix,
mulethi.
 Source: consists of dried, peeled or unpeeled, root &
stolon of Glycyrrhiza glabra Linn. , belonging to family
Leguminosae.
It is also obtained from other species of glycyrrhiza, giving a drug
with sweet taste. Liquorice should have a water-soluble extractive
not less than 20% w/w.
 Geographical Source:
Commercially cultivated in Spain and England.
G. glabra var. glandulifera
(Russian liquorice) grows in Russia
and G. glabra var. violacea from Iran.
Mrs. S.G.Gurunani PLCP, Nagpur. 27
Different varieties of G. glabra
1.G. glabra var. typica (Spanish liquorice) :
This plant has purplish blue coloured
papilionaceous flowers. It gives out large number
of stolons.

2. G. glabra var. glandulifera (Russian

liquorice) : It has a big root stock along with a
number of elongated roots, but does not bear
stolons.

3. G. glabra var. violacea (Persian liquorice) :

This plant shows violet flowers.
Mrs. S.G.Gurunani PLCP, Nagpur. 28
Cultivation and Collection:

Propagation by young pieces of stolons

planted in March at 2′ × 3′ distance

drug is harvested 3 -4 years after planting

Rhizomes and roots are dug up in October

Buds and rootles are removed, drug is

washed

peeled and divided into small pieces

dried first under sun and then in shades

,
Mrs. S.G.Gurunani PLCP, Nagpur. 29
Macroscopic Characters:
Colour : Unpeeled-yellowish- or dark brown externally,
yellowish internally, Peeled - pale yellow
Odour : Faint and characteristic.
Taste : Sweet.
Size : Length 20 to 50 cm and 2 cm in diameter.
Shape : Cylindrical pieces which are straight may be
peeled or
unpeeled. Peeled liquorice is angular.
Fracture
Extra : Fibrous
Features in the
: Unpeeled bark
show and
sthe splintery
presence in wood.
of small buds
encircling scaly leaves
longitudinally the drug is wrinkled,
peeled drugMrs.isS.G.Gurunani
fibrous PLCP, with
Nagpur. wrinkles 30
Mrs. S.G.Gurunani PLCP, Nagpur. 31
Chemical Constituents:
Triterpenoid saponin known as glycyrrhin(glycyrrhic acid),
Spanish -- 5 to 10 %, Russian --10%, Persian 7.5 to 13%
a potassium and calcium salt of glycyrrhizinic acid.
Glycyrrhizinic acid is glycoside
on hydrolysis yields glycyrrhetinic acid (glycyrrhetic acid), which has
a triterpenoid structure
bitter principle glycyramarin resins,
asparagin (2 to 4 %) , fat.
Glucose (up to 4%); sucrose (2.5 to 6.5 %);

The flavonoids, yellow in colour, are liquiritin and isoliquiritin.

The Indain liquorice roots contains 2 – methylisoflavones and
a coumarin viz. Carbenoxolone , possesses significant minerocorticoid
activity.
Mrs. S.G.Gurunani PLCP, Nagpur. 32
 COO-

Glc Glc O
Glycyrrhetic acid

Glycyrrhizinic acid

Glycyrrhizin
Mrs. S.G.Gurunani PLCP, Nagpur. 33
Mrs. S.G.Gurunani PLCP, Nagpur. 34
Standards:
1. Ash value
1.Peeled drug : NMT 6 %
2.Unpeeled drug : NMT 10 %
2. Acid insoluble ash
1.Peeled drug : NMT 1 %
2.Unpeeled drug : NMT 2.0 %
3. Water-soluble extractive : NLT 20%, including 7%
of glycyrrhizin.
4. Dilute alcohol soluble extractive : NLT 25.0 %.

Chemical Test:
On addition of 80% sulphuric acid, the thick section
of drug or powder shows deep yellow colour.
Mrs. S.G.Gurunani PLCP, Nagpur. 35
Uses:
1.Traditionally, expectorant and demulcent , in cough
mixtures,
sweetener and as a flavourant in formulations with
nauseous drugs like, ammonium chloride, alkali iodides,
quinine, cascara, etc. and in beverages, confectionery and
pharmaceuticals.

2. Due to flavonoid content (isoliquiritin) with antigastric

effects, it is used in peptic ulcer in the form of
deglycyrrhized liquorice (DGL).
This form has a reduced minerocorticoid activity and is
antispasmodic.

Mrs. S.G.Gurunani PLCP, Nagpur. 36

3. Because of minerocorticoid activity (due to glycyrrhetinic
acid), it is employed in place of corticosteroids for the
treatment of rheumatoid arthritis, inflammations and
addision’s disease. But, heavy doses may cause sodium
retention, consequently leading to hypertension, water
retention and servere electrolyte imbalance. Glycyrrhizin
is an established anti-inflammatory drug.
4. Residual matter remaining in the preparation of liquorice
liquid
extract is reported to have been used as a foam stabilizer
in
foam type of fire extinguisher.
5. Liquorice is an ingredient of liquorice compound powder
which is claimed to have a potentiating action of senna.
Mrs. S.G.Gurunani PLCP, Nagpur. 37
Other Preparations:
1. Liquorice powder : it is a powder of peeled
drug.
2. Liquorice compound powder : It contains
senns leaf, liquorice, sublimed sulphur and sucrose
and is used as laxative.
3. Liquorice liqid extract
4. Glycyrrhiza fluid extract: It contains liquorice,
ammonia and alcohol.
5. Liquorice lozenges : It contains liquorice
extract and anise oil along with a base.
6. Ammoniated glycyrrhizin : It is the ammonium
salt of glycyrrhizin and used as sweetening agent.
Mrs. S.G.Gurunani PLCP, Nagpur. 38
Adulterants and Substitutes:
Manchurin liquorice is obtained from
Glycyrrhiza uralensis. It is pale chocolate brown
in colour with exfoliated cork and wavy
medullary rays. It is free from suger, but
contains glycyrrhizin.

Russian liquorice may be peeled and obtained

from Glycyrrhiza glabra variety glandulifera.
The drug is purplish in colour with numerous
long roots, but no stolons.
Mrs. S.G.Gurunani PLCP, Nagpur. 39
Mrs. S.G.Gurunani PLCP, Nagpur. 40
 Quillaia
Synonym: Soap bark, Panama wood , China bark,

Biological source : dried inner bark of Quillaja

saponaria Molina , Rosaceae , the Bark is
stripped off from trunk, freed from rhytidoma
and dried .

Geographical source : Peru

In India , UP & Punjab , on
Nilgiris

Mrs. S.G.Gurunani PLCP, Nagpur. 41

Organoleptic properties:
Colour : Outer -Pale brownish or yellowish white
colour
Inner –Pale yellow to white
Odour: Odourless, sternutatory
Taste: Acrid , astringent and unpleasant
Size : Length -- 1 m
Breadth --10-20 cm
Thickness -- 3-10 mm
Shape : Large flat pieces
Fracture : Splintary

Mrs. S.G.Gurunani PLCP, Nagpur. 42

Constituent: contains a mixture of saponins 9-10 %
Quillaiic acid & Quillaia sapotoxin
Tannins , Starch and other polyphenols,
calcium oxalate.

Use: Medicine :- expectorant , diuretic , cleaning wounds,

emulsifying agent
Industry:- as detergent ,cleaning silk, in fire
extinguisher,
metal polish, in the manufacture of food
additives
Pharmaceutical: emulsifier - volatile oils, tars

It is used as a humectant in baked goods, frozen dairy

products, and puddings and as a foaming agent in soft drinks,
Shampoos , hair tonics, cosmetics ..
Mrs. S.G.Gurunani PLCP, Nagpur. 43
Mrs. S.G.Gurunani PLCP, Nagpur. 44

Polygala Senega: root

 Senega
 Synonym : Radix Senegae
 Source: It consists of the dried roots and root
crowns of
Polygala senega L., P. senega var. latifolia Torrey
Gray,
or other closely related Polygala species
(Polygalaceae)
NLT 29 % alcohol soluble extractive
 Geographical Source : cultivation –Japan
Indigenous to eastern Canada and north-
eastern USA, Mrs. S.G.Gurunani PLCP, Nagpur. 45
Description :
A perennial herbaceous plant with
numerous stems sprouting from a
single thick crown arising from a
conical, twisted, branched yellow
root .

Aerial portion consists of several

erect or ascending, smooth stems
up to 15-40 cm high, bearing
alternate, lanceolate or oblong-
lanceolate leaves with serrulate
margins. Mrs. S.G.Gurunani PLCP, Nagpur. 46
Organoleptic properties:
Colour : Greyish to Brownish yellow
Odour: Characteristic, faint, sweet,
slightly rancid due to methyl
salicylate,
Taste: Sweet then acrid and irritating to
the throat
Size : Thickness :- 3-6 mm towards
crown
Width :- 1-2 cm
Shape : It is keel with a sharp spiral portion
Mrs. S.G.Gurunani PLCP, Nagpur. 47

tapering
Microscopic characteristics
• Several rows of light-brown cork cells;
• secondary cortex composed of parenchyma cells and sieve
tubes.
• medullary rays, 1-3 cells wide.
• Phelloderm of slightly collenchymatous cells containing
droplets of oil.
•Phloem and xylem arrangement usually
normal, especially near the crown,
•Xylem usually central,
consists of vessels up to 60mm in dia.
associated with numerous thin walled
Tracheids and a few small lignified
parenchymatous cells.
•Starch grains and calcium oxalate
• crystals absent
Mrs. S.G.Gurunani PLCP, Nagpur. 48

Senega: transverse section magn

Constituent:
Two Saponins - senegin – 4 % and polygalic acid -5.5 %

Senegin senegenin + senegenic acid +presenegenin

polygalitol,
methyl salicylate (increasing with age),
fixed oil 8-9 %
volatile oil .12 %
resin,
sugar 7 %
pectin and albuminoids 18.40 %,
yellow coloring matter,
ash 4-5 p. c.

Mrs. S.G.Gurunani PLCP, Nagpur. 49

 Senegin –II

DMC
Glucose Fucose

Xylose
Rhamnose
Galactose Mrs. S.G.Gurunani PLCP, Nagpur. 50
 R1 R2 R3
(E)- H E-MC H
senegasaponin B

(Z)- H Z-MC H
senegasaponin B 3,4- dimethoxy cinnamic acid
(DMC )
senegin II H E- H /
Fucose
DMC /
galac —xyl— rham
(Z)-senegin II H Z- H
DMC
(E)-senegin III Rha E-MC H
(Z)-senegin III Rha Z-MC H
Mrs. S.G.Gurunani PLCP, Nagpur. 51
 3,4- dimethoxy cinnamic acid
(DMC )
/
Fucose
/
galac —xyl— rham

R1 R2 R3

(E)- H E-MC H
senegasaponin
B
(Z)- H Z-MC H
senegasaponin
B
senegin II H E- H
DMC
(Z)-senegin II H Z- H
DMC
(E)-senegin III Rha E-MC H
Mrs. S.G.Gurunani PLCP, Nagpur. 52

(Z)-senegin III Rha Z-MC H

 Uses:
 Stimulant expectorant in chronic bronchitis.
 Treatment of amenorrhea, asthma, constipation,
rheumatism and snake bites
 Precautions
Carcinogenesis, mutagenesis, impairment of fertility
Pregnancy: teratogenic effects
Overdose may cause nausea, diarrhoea and vomiting due to
gastrointestinal upset
 Dosage forms
Chopped crude drug for decoctions and extracts
Senega syrup 10% , Conc.Senega infusion in alc +ammonia
Store in a tightly closed container, protected from light and
humidity Mrs. S.G.Gurunani PLCP, Nagpur. 53
 Brahmi
 Synonym : Bacopa
 Source: It consists of the freash leaves and stems
of plant Bacopa moniera Linn. Belonging to
the family Scrophulariaceae
Should contain NLT 2.5 % of Bacoside A on
dried basis
 Geographical Source : In wet damp marshy
places

Mrs. S.G.Gurunani PLCP, Nagpur. 54

 Morphology :
Colour – Green
Odour - None
Taste - Bitter
Size - Leaves 2 cm
Shape – Fleshy , simple, Obovate , alternate,
Margin entire , Broad apex , sessile ,

Mrs. S.G.Gurunani PLCP, Nagpur. 55

Chemical constituents : Bacosides A & B , Hersaponin ,
Stigma sterol
Brahmine , Herpestine
Uses : Nervine tonic
Treatment for epilepsy and asthma
Plant has antianxiety effects
Diuretic & anti-cancer

CO

Mrs. S.G.Gurunani PLCP, Nagpur. 56

keukand Order: Zingiberales
Costus speciosus
Family: Costaceae

Mrs. S.G.Gurunani PLCP, Nagpur. 57