1. Glycosides
By
Subject Teacher : Mr. Dattaprasad N. Vikhe
Designation : Assistant Professor
Department of Pharmacognosy
Course: B Pharmacy
Subject :- P’cog & Phyto - II Class : Third Year B.
Pharmacy
2. Organic natural compounds present in a lot of plants and
some animals, these compounds upon hydrolysis give one
or more sugars (glycone) moieties and non sugar
(aglycone) moietyd
Glycoside=sugar group+ nonsugar group
(glycone) (aglycone or genin)
Glycone and aglycone are linked by glycosidic linkage
defination
3. Glycosidic linkage is formed between –
OH group of sugar and –H group of non
sugar moieties OR other sugar with loss
of water molecule glycoside bond
glycoside=glycone{---o---}aglycon
4. Sugar in glycosides is mostly beta-D glucose but other
sugars like galactose, mannose, rhamnose, digitoxose can
present.
Glycosides can be alpha or beta but plants contains only
beta glycosides
therapeutic effect of glycosides is only due to aglycon part
only and suger moiety facilitate absorption of glycoside,
transportation of aglycone to site of action .
so glycosides are hydrolysed to give aglycon part for action
5. Glycosides have therapeutic effect in human and
animals
they are used in traditional and modern medicines
as
cardio tonic
purgative
Analgesic
anti- rheumatic
demulcent
many other uses.
6. Classification
1-classification based on type of aglycone in
glycoside
Anthraquinone or anthracene glycoside
Sterols or cardiac glycoside
Saponin glycoside
Cyanogenic glycoside
Isothiocynate glycoside
Coumarins and furanocoumarins
Aldehyde glycoside
phenol glycoside
Steroidal
Miscellaneous glycosides
7. 2-classification based on type of sugar (glycone) part
glucose- glucoside
Rhamnose –rhamnoside
Digitoxose-digitoxoside
Glucose and rhamnose-glucorhamnoside
Rhamnose and glucose-rhamnoglucoside
8. 3-classification based on type of linkage between glycone
and aglycone
Linkage between –OH group of glycone and –H group of RADICALS
LIKE –CH,-OH,-SH,-NH of aglycone. glycoside is named by perfix like
C-glycoside,-sugar linked to carbon atom of aglycone
N-glycoside,- sugar linked to nitrogen atom of aglycone
O-glycoside,- sugar linked to oxygen atom of aglycone
S- glycoside- sugar linked to sulfur atom of aglycone
4-classification based on there use
Cathartics, cardio tonics, analgesics, anti-rheumatics, anti-
ulcer etc
9. Physical & chemical properties
Colorless, solid, amorphous, nonvolatile
(flavonoid- yellow, anthraquinone-red or
orange.)
Give positive reaction with Molisch's and
Fehling's solution test (after hydrolysis).
They are water soluble compounds, insoluble in
organic solvents
Most of them have bitter taste
(except: populin, glycyrrhizin, stevioside)
10. Odorless except saponin (glycyrrhizin).
when a glycosides has a lot of sugars its solubility in water decrease.
Glycosides hydrolyzed by using mineral acids and temperature or
by using enzymes
11. General extraction method of glycosides
Sta-otto method
The drug containing glycoside is finely powdered and subjected
to successive extraction in a soxhlet apparatus with alcohol or
suitable solvent.
first take drug containing glycoside, finely powdered that, and it
is extracted with alcohol or water by using soxhlet apparatus.
After extraction, collect the extract and treat with lead acetate to
precipitate tannins
12. after that filter it and to the filtrate pass H2S gas, to precipitated excess
of lead acetate and convert it to ppt of lead sulphide as this is toxic.
Now the extract again filter.
The filtrate is subjected to fractional crystallization, distillation or
chromatography gives pure component
And molecular structure of component is determined by the
spectrophotometer, Ultra Red assays, Infra red , NMR and mass
spectroscopy etc.
13. Saponins glycosides
They contain aglycon part sapogenin. harmful
safogenins are called sapotoxins.
This aglycone part have foaming action when shaked with water
and yields colloidal solution.
They are considerd as haemotoxic because they causes
haemolysis of erythrocytes, hence some of them used as fish
poisons
Saponins are categorized in to two groups
1-steroidal saponins(tetracyclic triterpenoid saponins) 2-
pentacyclic triterpenoid saponins
14. Chemical tests for saponin glycosides
Haemolysis test-a drop of blood on slide was mixed with few drops of
aq. Saponin solution,RBCs becomes ruptured in presence of saponins
Foam test- to 1gm of drug add 10-20 ml of water, shake for few min,
formation of froth which persist for 60-120 seconds
16. Liquorice roots
marathi- jestha madhu
Synonyms
Glycyrrhiza, mulethi, yasti,
Biological source-
It consist dried ,unpeeled roots and stolons of Glycyrrhiza
glabra linn
Family –leguminosae
It should contain not less than 3% of glycyrrhinic acid.
17. Geographical source
Commercially cultivated in Spain, Sicily and England
Varieties of glycyrrhiza glabra
G.Glabra var. typica ( spanish liquorice)
G.Glabra var. glandulifera (russian liquorice)
G.Glabra var. violacea ( persian liquorice)
18. Cultivation and collection
Propogation of plant is done by using pieces of stolons.
each piece should have 2-3 buds of aerial shoot.
Plant grow well in deep sandy soil with manures or fertilizers.
pieces of stolon planted in march at 2*3 distance.
Crop is kept free from weeds.
Roots harvested after 3-5 years of planting,they are obtained from
plants by dugging befor fruiting.
Drug is washed with water.
Large pices are cut in small one and dried under sun and then in shade
19. Macroscopic charecters
Colour- unpeeled drug yellowish brown or dark
brown externally and yellowish internally
Odour- faint and characteristic
Taste- sweet
size- length 20 to 50 cm, diameter 2cm
Shape- unpeeled pieces are straight
Fracture- fibrous in bark and splintery ( small, thin,
sharp piece of wood) in wood
Extra feature- unpeeled pieces show presence of
small buds and longitudinal wrinkles
21. Cork cells- polyhedral tubular brownish colour
thick, lignified, partially lignified fibers in phloem
and xylem
Starch and cal oxalate crystals present in
parenchyma
Stolon contains pith while root do not contain pith
Pith, or medulla, is a tissue in the stems of vascular
plants. Pith is composed of soft, spongy parenchyma
cells, which store and transport nutrients throughout
the plant
22. Chemical constituents
Main constituent is glycyrrhizin( glycyrrhizic acid) glycoside
on hydrolysis it yields glycyrrhetinic acid(triterpenoide)
other constituents are sucrose, glycyramarin(bitter principle), resins,
fat, asparagin
it contain flavonoids like liquiritin and isoliquiritin
24. Uses
Expectorent,
demulcent(agent that forms a soothing film over a
mucous membrane, relieving minor pain and
inflammation) ,
falvouring agent,
anti- inflammatory,
rheumatide arthritis,
due to flavonoid content with antigastric ulcer effect
it is used in peptic ulcer, antispasmodic
it is ingredient of liquorice compound powder which
is potentiate the effect of senna
25. Adulterants and substitutes
Manchurian liquorice ( glycyrrhiza
uralensis), it is free from sugar but contains
glycyrrhizin- pale chocklet brown colour
Russian liquorice( G glabra var
glandulifera), it have purplish colour
27. DIOSCOREA
SYNONYM- yam, rheumatism root
B.S-
it consist of dried tubers of plant Dioscorea
deltoidea,D.composita, and other species of
dioscorea.
family- dioscoreaceae
28. Geographical source-
North western Himalaya,Punjab to Nepal,
In China up to altitude of 1000 to 3000
meter.
it is cultivated in Jammu and Kashmir
29. Cultivation and collection
-Cultivated from tubers with crown of about 70-80 gm in weight.
-first sown in nursery bed.
-after 30-40 day tubers sprout.(germinate)
-after 2-3 month of growth transplanted in field at distance of 30*60cm.
-they required support for optimum growth as veins are weak andtender.
-Manures and organic fertilizers are supplied.
-Irrigation done every 10 days
-fresh tubers are harvested by deep ploughing after two years of crop.
-Dried and they loose 50% weight after drying.
30. Macroscopic charecterstics
Colour- slightly brown
Odour- odourless
Taste-bitter
Extra features- it is climber, rhizomes are soft,
horizontally arranged and very close to soil, drug
covered with scattered roots.
31. Microscopic characteristics-
Epidermis is absent in TS.
cork consist few layers.
and few layers of cortical parenchyma tissue.
stele
( primary vascular tissue in the stem or root of a vascular p
lant, consisting of the xylem and
Phloem together with supporting tissues, such as pith.) is
major part of drug consisting collateral fibro-vasculer
bundles.
endodermis and pericyle are indistinguishable.
32. CHEMICAL CONSTITUENTS
75% non edible starch as it is bitter.
chief constituent is diosgenin {sugar-free (aglycone) . It is
hydrolytic product of saponin-dioscin}
other Glycosides-
smilagenin,
epismilagenin,
yammogenin
33. Uses
Diosgenin is steroidal sapogenin
so used as precursor for synthesis of
corticosteroids,
sex hormones,
oral contraceptive.
diosgenin used in treatment of rheumatoid
arthritis
34. Isolation of diosgenin
dried tubers are powdered
and dioscin is hydrolysed by mineral acids
to obtain diosgenin,
then it is extracted by non polar solvents
like benzene or solvent ether
35. Allied species
Dioscorea flouribunda- india,
central america -D.villosa-
USA-D,deltoidea wall var
. sikkimensis prain
Himalayas, Nepal, Sikkim
Cheilocostus speciosus or crêpe ginger is alternate source
of diosgenin (1.5%)
37. SYNONYMS
Digitalis leaves , foxglove leaves
B S
it consist dried leaves of Digitalis Purpurea
family
Scrophulariaceae
Should contain not more than 5% moisture,
dried below 60 0 C
39. CULTIVATION AND COLLECTION
It is propagated by seeds.
it requires calcarious, acidic, sandy soil for growth.
seeds are very small in size i.e 100 seeds weigh 40 to 70 mg.
seeds are mixed with fine sand and sown in nursery beds in march/april.
young seedlings are transplanted in sep/november.
crop is manured and kept free from weeds.
In first year plant bears rosette leaves and in second year sessile leaves.
Leaves collected in second year by handpicking when 2/3 rd of flowers
are fully developed.
40. leaves immediately dried in vacuum driers.
dried leaves containing not more than 5% moisture are
packed in airtight containers with dehydrating agents.
Presence of moisture deteriorates glycosides. If dried above
60 0 C potency lost due to chemical degradation.
41. MACROSCOPIC CHARECTERS
Colour- dark greyish green
odour- slight
taste- bitter
size- 10 to 40 cm long and 4 to 20 cm wide
shape- ovate- lanceolate(shape like lance head or tapering to a point at
each end) to broadly ovate( like egg)
Extra feature
Leaves are slightly pubescent on both surfaces, pinnate venation,(one
main vein extending from the base to the tip of the leaf and smaller
veins branching off the main vein.) generally leaves are broken and
42. Microscopic characters
Dorsiventral leaf.(two surfaces differing from each other in
appearance and structure,)
covering and glandular trichomes on boath surfaces.
covering trichomes are uniseriate,( arranged in single series)
3 to 4 cells long, having collapsed cells, acute apex and
warty( hard rough lump growing on) cutical.
glandular trichomes are short, unicellular stalk and bicellular
or unicellular head.
it have anomocytic stomata (irregular celled)
43. Starch grains are present in endodermis.
collenchyma present at upper and lower
epidermis and pericyclic ( is a cylinder of
parenchyma or sclerenchyma cells that lies just
inside the endodermis and is the outer most
part of the stele of plants.)part.
44. Chemical constituents
0.2 to0.45% cardenolides.
purpurea glycoside A and B,
glucogitaloxin.
Other,
odoroside H,
gitaloxin,
verodoxin,
glucoverodoxin
Saponin glycosides
digitonin,
gitonin
45. Hydrolysis products of purpurea glycosides
Purpurea glycoside A Purpurea glycoside B
hydrolysis hydrolysis
digitoxigenin + 3 digitoxose gitoxigenin +3 digitoxose
digitoxigenin
gitoxigenin
46. Uses
Congestive heart failure,( heart is unable to pump
sufficiently to maintain blood flow to meet the needs of the body)
artrial fibrillation( common type of abnormal heartbeat. The
heart rhythm is fast and irregular in this condition.),
artrial flutter, ( abnormal heart rhythm that occurs in the atria of
the heart. When it first occurs, it is usually associated with a fast heart rate
or tachycardia (beats over 100 per minute))
supraventricular tachycardia
47. Adulterants
Verbascum Thapsus ( mullelin leaves)- large wooly branched candelabra(large
branched candlestick or holder for several candles) trichomes.
Primula Vulgaris (comfrey leaves)-multicellular trichomes forming hook at top.
Symphytum Officinale( primrose leaves)-uniseriate covering trichomes 8 to 9 cell long.
48. Anthraqiunone glycosides
Anthraquinone is derivative of anthracene.( C14H10, consisting of three
fused benzene rings)
Natural anthraquinone derivative have laxative effects
These glycosides contains anthraquinone, anthrone, anthranol,
dianthranol, oxanthrone, dianthrone etc as aglycone part.
parent molecule for all these aglycones is anthraquinone. In reduced
form anthraquinone is present as anthranol or anthrone wich are
isomeric to each other.
49. oxanthrone is intermediate substance from anthraquinone to anthranol.
Bimeric form of anthrone is dianthrone.
in fresh drug these aglycones are present in reduced form witch are
biologically more active but during drying and storage they hydrolyzed
, oxidized.
Sugar part can be glucose, rhamnose, arabinose, primeverose
etc.
51. Chemical tests
1 borntrager,s test
To1 gm of drug add 5-10 ml of dil HCl, boil on water
bath for 10 min and filter. Filtrate then extracted with
CCl4/ benzene and add equal amount of ammonia
solution to filtrate and shake. Ammonical layer
becomes pink or red due to presence of
anthraquinone.
52. 2 .modified borntrager,s test
to 1 gm drug add 5 ml dil HCl + 5 ml
ferric chloride( 5%w/v). Boil on water
bath for 10 min, cool , filter. Filtrate then
extracted with CCl4/benzene and add
equal volume of ammonia solution. Pink
or red colour forms due to
anthraquinone . This test used for C- type
anthraquinone glycoside
54. Senna
Synonym
senai- ki- patti, tinnevelley senna, cassia senna
B.S
It consist of dried leaflets of Cassia Angustifolia known
as indian senna or Cassia Senna vahl
family
Leguminosae
it should contain note less than 1 % of sennoside A
and B on dried basis
55. GEOGRAPHICAL SOURCE
inndian senna cultivated in
tinnevelley, madurai, ramnathpuram districs in
Tamilnadu
, kaddapa dist in Anthrapradesh
, Kutch in Gujarat and Rajasthan
56. cultivation collection and preparation
sowing is done by seed broadcasting method .
for earlier germination seed surface is triturated with sand .
seeds are sown thinly.
it required red loamy or coarse gravelly soil( high proportion of small stones).
First sowing done in feb- march.
Second sowing done in oct- november.
It required semi irrigation or light irrigation..
Once flowers are grown cutting given to flower stalk for further branching to occur.
leaves are harvested after 2-3 months of planting.
57. First plucking done when leaflets fully grown, second plucking after
one month of first
plucking. Last plucking done after 4-6 weeks of second.
Plant is uprooted after third plucking.
Leaflets are dried in shade for 7-10 days.
leaves are tossed( move from side to side or back and forth) to separate
pods.
Then packed in to large bundles under hydraulic pressure.
Pressing produce transverse line on Indian senna witch are absent on
Alexandrian senna leaves.
58. Macroscopic characteristics
colour- yellowish green
odour- slight
taste- mucilaginous, bitter and charecterstic
size- 7-8 mm width, 25-60 mm length
shape- lanceolate, apex acute with spine at
top.trichomes present on both surfaces.
60. it is isobilateral leaf.( divided into symmetrical halves )
trichomes present on both surfaces.
Trichome,s are unicellular, conical, thick walled warty,
slightly curved at base
.palisade tissue present on upper and lower surface,
they contain cluster crystals of cal oxalate
.
Pricyclic fibers present towards upper epidermis and
above xylem
61. Chemical constituents
sennoside A , sennoside B . they have rhein( cassic acid) dianthrone as
aglycone.
other anthraquinone
sennoside C,D,
rhein ,
kaempferol,
aloe- emodin,
isorhamnetin,
mucilase ,
resin,
myricyl alcohol,
salicylic acid,
crysophagic acid,
Cal. oxalate.
tinnevelley glucoside
62.
63. USES
purgative
MOA-
anthraquinone glycosides absorbed first in
intestinal tract, then aglycone is separated and
excreted in colon. it causes irritation and
stimulation of colon, so movement( peristalsis)
of colon increases, peristalsis also reduce water
absorption hence soft and bulky faeces are
formed. due to resin and emodin content
griping occurs hence drug is given with
carminatives.
64. ADULTERANTS AND SUBSTITUTES
Dog senna (c. obovata)- shape of leaves is
obovate(ovate with the narrower end at the base.)
with tapering apex. Papillose( nipple-like structure)
cells in lower epidermis
Palthe senna- anthraquinone glycosides
absent.leaflets have long hairs and when boiled with
chloral hydrate solution crimson colour occurs.
bombay senna, mecca senna, arabian senna etc
have leaflets brownish green colour and more
elongated and narrower in shape.
65. Alexandrian senna
synonym
folia sennae alexandrina, egyptian senna, cassia
senna
B.S
it consist dried leaflets of Cassia Acutifolia delile
family
Leguminosa
66. Macroscopic and microscopic charecters
are same like indian senna.
colour is pale greyish green.
Base is more symmetrical, more
pubescent.
Chemical constituents and adulterants are
same like Indian senna
68. Aloes
Synonym
Aloe, Hindi-musabbar, kumari. Marathi- korphad
BS
It is dried juice of leaves of Aloe Barbadensis miller known as
curacao aloe or ALoe Perryi baker known as socotrine aloes
or Aloe Ferox miller, and hybrids of this species Aloe Africana
miller and Aloe Spicatya baker known as cape aloes
family
Liliaceae
69. Geographical source
it is indigenous to estern and southern Africa.
Cultivated in Caribben Island,
Europe,
India
70. Cultivation and collection
Propagation is done from root suckers.
Root suckers planted in rows about 50 cm apart.
Plant grow in dry climate and poor grade soil.
Roots do not penetrate much in soil.
Manure is provided.
Leaves are cut first time after second year of planting and drug is obtained from
leaves for 12 years.
After 12 years plant is uprooted and new crop is taken.
during collection cut is given at base of leaves so juice located in parenchymatous cells
of pericycle exudes out.
71. Preparation of aloe
1 barbados or curacao aloes
it is obtained by giving cut on leaves of aloe barbadensis.
because of spines on leaves it is put in to kerosene tins immediately
after cutting .
Then kept in tilted position on V- shaped wooden troughs to drain out
juice.
juice is boil in copper pans for evaporation to obtain thick juice.
Then it is poured it to metal containers , where it hardens.
72. 2 cape aloes
Obtained from aloe ferox and its hybrid species.
Leaves are cut transversely and kept in circular manner in basin shaped
depression lined with goat skin or canvas.
They are kept in this position for 5-6 hours till all juice exudes out and
collected in goat skin.
juice is boiled in iron kettle with continuous stirring with wooden
paddle.
Once juice is thick it is poured in to wooden cases where it solidify.
73. 3 socotrin aloes
It is obtained from aloe perryi in east Africa.
juice is collected in goat skin and allowed to become semisolid in nature.
It is exported in past like consistency.
4 zanzibar aloes
it is verity of socotrine aloe.
Juice is placed in skin of small carnivorous animals, where it solidify.
Then packed in wooden boxes.
It is also called monkey skin aloe, although skin is not of monkey.
74. Description
1 curacao aloes
Odour-strong odour resembling to iodoform.
Taste is bitter.
Colour is brownish black, opaque mass.
Fracture-uneven fractured surface
2 cape aloes
colour- dark brown or greenish brown to olive brown mass.
Taste – nauseating and bitter.
Odour - sour but distinct.
Fracture - glassy
75. 3 socotrine aloes
colour- brownish yellow, opaque mass with pasty consistency.
Taste- extremely bitter, nauseous.
Odour –unpleasant
4 zanziber aloes
colour- liver brown.
Odour- characteristic but not disagreeable.
taste bitter.
Fracture – dull, waxy, smooth, even
76. Microscopic charecterstics-
TS shows
outermost cuticle followed by epidermis, palisade tissue, mucilaginous
parenchyma mesophyll.
mesophyll contains vascular bundle covered with pericycle fibers layer.
Inside pericycle ,aloetic cells are located witch contains aloe gel (
viscous yellow).
Calcium oxalate crystals present in parenchyma.
leaves are sessile
77. Microscopic chrecters of aloe powder
It is useful for identification of powdered aloes. it is studied in lacto phenol reagent to gradually
solubilize particles so crystals can clearly seen
1 curacao aloes
fragments consist of large number of very small needle or slender prisms
2 cape aloes
transparent, brown, angular or irregular fragments.
3 socotrine aloes
fragments consist of large prisms in group or dispersed form.
4 zanzibar aloes
irregular lumps in with modular masses are embedded.
81. Chemical teasts
general chemical tests
1 gm aloe is powder boiled with 10 ml water, filtered. Filtrate
used for bromine test and schoenteten,s reaction.
1bromine test- filtrate+ freshly prepared bromin solution=
pale yellow ppt of tetrabromalin
2schoenteten,s test- filtrate+ borax shake well until borax
dissolves.few drop of this soluition added in test tube filled
with water= green fluorescence appears.
82. Special test
these test are to distinguish between varieties of aloe
1 nitrous acid test-
aqueous solution of aloe + sodium nitrate crystals + acetic
acid
curacao aloes-sharp pink to carmine colour
cape aloes- faint pink colour
socotrine and zanzibar aloes- very less change in colour
83. 2-Nitric acid test-
nitric acid applied to drug or its aqueous solution
curacao aloes- deep brownish red colour
cape aloe- brownish colour changes to green
socotrine aloes- pale brownish- yellow colour
zanzibar aloes- yellowish brown colour
84. 3 kupraloin test( klunge,s isobarbaloin test)-
Dil. aqueous solution of aloe+ drop of copper sulphat+
sodium chloride + excess 90% alcohol
Curacao aloes-wine red colour persist for 4 hours
Cape aloes- faint colour rapidly changes to yellow
Socotrine aloes-no colour
zanziber aloes- no colour
85. Uses
purgative.
Stronger purgative than all anthraquinon glycosides.
Toprevent gripping action carminative can be given.
it is ingredient of compound tincture of benzoin(
friar,s balsam)
aloe gel is used for topical application and many
cosmetic uses.
86. Aloe gel-
it is obtained from inner
parenchyma cells of leaf.
Slightly viscous and clear
liquid. It should not be
contaminated with aloe juice
87. Adulterants and substitutes
Natal aloes-it contains natalion, homonatalion, resin,
it is weak purgative
Mocha aloes- brittle, black and glossy with strong
odour
Aloe can be adulterated with black catechu.
Alcoholic extract of aloe gives deep brown colour
while black catechu gives black colour.
90. Macroscopic characteristics
colour- rhizomes are yellowish-brown
Odour-peculiar( different)
Taste- sweet taste followed by intense bitter
Fracture- short and smooth in dried drug but
tough and flexible in moist drug