2. 1 • Introduction
2 • Classification
3 • Physical Properties
4 • Chemical Properties
5 • Distribution
6 • Extraction
7 • General Chemical test
8 • Examples of glycoside
Contents
3. General Introduction
Definition
Glycosides are the condensation products of sugars with a
host of different varieties of organic hydroxy (occasionally
thiol) compounds (invariably monohydrate in character), in
such a manner that the hemiacetal entity of the carbohydrate
must essentially take part in the condensation.
Introduction
4. Classification on the basis of Glycon moeity
Classification on the basis of Aglycon moeity
Classification on the basis of Glycosidic linkage
Classification on the basis of Pharmacological action
Classification
5. Glucoside
Fructoside
Glucouronoids
Arabinoside
Riboside
Digitoxoside (Digitoxose)
Glucorhamnoside (Glucose and rhamnose)
Rhamnoglucoside (Rhamnose and glucose)
Pentoside
Hexoside
Classification on the basis of Glycon moeity
7. Oxygen (O-glycoside)
Sugar molecule is combined with phenol or –OH group of
aglycon. (Amygdaline, Arbutin, Salicin, cardiac glycosides,
Anthraquinone glycosides etc. )
Classification on the basis of Glycosidic linkage
10. Carbon (Cglycoside)
Sugar molecule is directly attached withC—atom of
aglycon, Anthraquinone glycosides like Aloin,
Barbaloin, Cascaroside and Flavan glycosides, etc.
11. Anti-malarial
Cardiovascular
Anti-cancer
Cathartic
Purgative
Anti ulcer
etc
Classification on the basis of Pharmacological action
12. Optical active
Colorless (flavonoid- yellow, anthraquinone-red)
Odorless except saponin (glycyrrhizin)
Bitter taste (except: populin, glycyrrhizin, stevioside)
solid, semi solid
Amorphous
Nonvolatile
water soluble (lot of sugars its solubility in water decrease)
Alcohol soluble
Insoluble in organic solvents
Physical properties
13. Complex structure
High molecular weight
Glycosidic linkage
Hydrolyzed by
Mineral acids
Temperature
Enzymes
Alkali
Gives test for carbohydrate after hydrolysis
Chemical properties
17. (Latin sapo— soap).
They get their name from the soap wort plant (Saponaria), the
root of which was used historically as a soap.
Saponin
Sapogenin
Sapotoxin
Hemolytic activity,
Sneezing effect,
Toxicity
Complex formation with cholesterol
Antibiotic properties
Saponin Glycoside (Natural Detergent)
18. Haemolysis test
A drop blood on slide was mixed with few drops of aq.
Saponin solution, RBC’s becomes ruptured in presence
of saponins.
Foam test
To 1 gm of drug add 10–20 ml of water, shake for few
minutes, formation frothing which persists for 60–120 s
in presence of saponins.
Chemical test
19. Monocot Plants
Amaryllidaceae, Dioscoreaceae and Liliaceae
Dicot Plant
Apocynaceae, Leguminosae and Solanceae
Leaf
Root
Stem
Fruit
Distribution
21. Synonyms: yam, rheumatism root
Biological source
It consist of dried tubers of plant Dioscorea deltoidea,
D.composita, and other species of dioscorea belonging to
family Dioscoreaceae.
Geographical source
North America, Mexico, India (Himalayas from Kashmir and
Punjab up to an altitude of 3,000 m), Nepal and China.
Daiscorea
22. Cultivation Collection
It is a perennial climber growing to 3 m.
sandy, loamy and clay soils and well-drained soil.
acid, neutral and basic (alkaline) soils.
Cultivated in three methods
sowing seeds, stem cuttings, tubercles.
March to April 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.
Irrigation done every 10 days
fresh tubers are harvested after two years of crop.
Dried and they loose 50% weight after drying.
23. Morphology
Colour- slightly brown
Odour- odourless
Taste-bitter
Size – varying
Extra features- it is climber, rhizomes
are soft, horizontally arranged and
very close to soil, drug covered with
scattered roots.
24. Microscopy
shows the absence of epidermis,
the cork is made up of few layers
next to cork it has conical parenchymatous tissue with thin wall.
Stele consists of collateral type of fibrovascular bundles.
Indistinguishable endodermis and pericycle.
25. Chemical Constituents
75% non edible starch as it is bitter.
chief constituent is diosgenin {sugar-free (aglycone) . It is
hydrolytic product of saponin-dioscin}
Sapgenase enzyme
other Glycosides-
smilagenin,
epismilagenin,
yammogenin
26. Uses
Diosgenin is steroidal sapogenin
so used as precursor for synthesis of corticosteroids,
sex hormones,
oral contraceptive.
diosgenin used in treatment of rheumatoid arthritis and
asthama
Adulteration
D. flouribunda
D. villosa
D. prazeri
27. Synonyms: Glycyrrhiza, mulethi, yasti, marathi- jestha madhu
Biological source
Liquorice consists of subterranean peeled and unpeeled stolons,
roots and subterranean stems of Glycyrrhiza glabra Linn, and
other species of Glycytrhiza, belonging to family Leguminosae.
Geographical source
It is mainly found in China, Europe, India (sub-Himalayan tracts
and Baluchistan), Iraq, Japan, Kurdistan, Spain, Turkey, and the
United States.
Liquorice roots
28. The following are the three commonly grown varieties of
Glycyrrhiza glabra, namely:
(a) G. glabra var. violaceae (Persian Liquorice): violet flowers
(b) G. glabra var gladulifera ( Russian Liquorice): distinct big
stock together with a number of elongated roots, but it has not
got any stolon
(c) G. glabra var. typica (Spanish Liquorice): This specific plant
bears only purplish-blue coloured flowers. It possesses a large
number of stolons.
29. Cultivation 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
30. Morphology
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
31. Microscopy
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
32. Chemical Constituents
Main constituent is glycyrrhizin( glycyrrhizic acid) glycoside
Glycyrrhizin is found to be 50 times as sweet as sugar.
on hydrolysis it yields glycyrrhetinic acid (triterpenoide)
other constituents are sucrose, glycyramarin(bitter principle),
resins, fat, asparagin
it contain flavonoids like liquiritin and isoliquiritin
33. Chemical Test
When 80% sulphuric acid is added to a section or
powder of the drug orange yellow colour is produced
due to transformation of flavone glycoside liquiritin
to chalcone glycoside isoliquiritin.
34. Uses
Expectorant,
Demulcent
Falvouring agent,
anti- inflammatory
rheumatide arthritis,
due to flavonoid content with anti-gastric ulcer effect it is used
in peptic ulcer, antispasmodic
it is ingredient of liquorice compound powder which is
potentiate the effect of senna
35. Adulteration
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
36. These drugs all act by affecting the availability of intracellular
Ca+2 for myocardial contraction or increasing the sensitivity
of myocardial contractile proteins.
to enhance the tone, excitability and above all the
contractibility of the cardiac muscle; and
to increase the diuretic action, due principally to the enhanced
renal circulation (an inherent secondary action).
.
Sterol or Cardiac Glycoside
From 1500 B.C as arrow poision, emetics, diuretics and heart tonics.
37. The steroid nucleus has hydroxyls at 3- and 14-positions of
which the sugar attachment uses the 3-OH group. 14-OH is
normally unsubstituted. Many genins have OH groups at 12-
and 16-positions.
These additional hydroxyl groups influence the partitioning of
the cardiac glycosides into the aqueous media and greatly
affect the duration of action.
One to four sugars are found to be present in most cardiac
glycosides attached to the 3ß-OH group.
The sugars most commonly used include L-rhamnose, D-
glucose, D-digitoxose, D-digitalose, D-digginose, D-
sarmentose, L-vallarose and D-fructose.
These sugars predominantly exist in the cardiac glycosides in
the ß-conformation.
39. Keller-kiliani test
Alcoholic extract of drug + equal volume water and 0.5 ml
strong lead acetate solution. Shake and filtered. filtrat
extracted with equal volume of chloroform. Chloroform
extract evaporated to dryness and dried residue dissolved in 3
ml glacial acetic acid+ few drop of ferric chloride solution.
this solution transferred to test tube containing con. Sulphuric
acid. Reddish brown layer formed wich turnes bluish green
after standing due to presence of digitoxose.
.
Chemical test
40. Legal test
Alcoholic extract of drug + equal volume water and 0.5 ml
strong lead acetate solution. Shake and filtered. Filtrat
extracted with equal volume of chloroform. Chloroform
extract evaporated to dryness and dried residue was dissolved
in 2 ml pyridine+ 2 ml sodium nitroprusside + sodium
hydroxide solution ( to make alkaline).pink colour due to
glycoside or aglycone moiety.
Chemical test
41. Baljet test
T.S of digitalis leaves + sodium picrate solution= yellow to
orange colour due to aglycone or glycoside
3,5- dinitro benzoic acid test
alcoholic solution of drug + few drops of sodium hydroxide +
2% solution of 3,5 dinitrobenzoic acid= pink colour due to
cardiac glycosides
Chemical test
42. Synonyms: Digitalis leaves , foxglove leaves, purple foxglove,
finger flower, lady’s glove, Folia Digitalis, Digifortis; Digitora;
Pil-Digis; Neodigitalis.
Biological source
it consist dried leaves of Digitalis Purpurea belonging to family
Scrophulariaceae.
Geographical source
It is mainly found in England, Germany, France, North America,
India (Kashmir and Nilgiri Hills) , Iraq, Japan, Kurdistan,
Mexico, Nepal,Spain, Turkey
Digitalis
43. Cultivation Collection
It is propagated by seeds.
it requires calcarious, acidic, sandy soil for growth.
seeds are very small in size 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.
leaves immediately dried in vacuum driers.
Dried at 60 degree up to 5% moisture and packed in containers
with dehydrating agents.
44. Morphology
Colour- dark greyish green
Odour- faint and characteristic
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 crumbled.( break in small fragments)
45. Microscopy
Dorsiventral leaf. (two surfaces differing from each other in
appearance and structure,)
covering and glandular trichomes on boath surfaces.
covering trichomes are uniseriate 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.
anomocytic stomata
calcium oxalate crystals absent
Starch grains are present in endodermis.
collenchyma present at upper and lower epidermis
46.
47. Chemical Constituents
Purpurea glycoside A, Purpurea glycoside B, and Purpurea
glycoside C
other glycosides (e.g.; digitalin, diginin);
saponins (e.g.; digitonin, gitin and digitosaponin);
tannins, gallic, formic, acetic, succinic and benzoic acids; fatty
acids and enzyme digipuridase solely responsible for
hydrolysis of purpurea glycosides.
48.
49.
50.
51. 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)
It stimulate urine flow
52. Adulteration
Verbascum thapsus also known as Mullelin leaves. These
leaves are covered with large woolly branched candelabra
trichomes.
Primula vulgaris (Primrose leaves) can be detected by the
presence of long eight- to nine-celled covering trichomes in
them.
Symphytum officinale (Comfrey leaves), this leaves contains
multicellular trichomes forming hook at the top.
Inula conyza (Ploughman’s Spikenard), may be
distinguished by their greater roughness, the less-divided
margins, the teeth of which have horny points and odour
when rubbed.
54. 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.
55. 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.
56. Dicot: Ericaceae, Euphorbiaceae, Leguminoseae, Lythreaceae,
Polygonaceae, Rhamnaceae, Rubiaceae and Verbenaceae.
Monocot: Liliaceae,
fungi and lichens.
57. borntrager,s test
To 1 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.
58. 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
59. Synonyms: senai- ki- patti, tinnevelley senna, cassia senna
Biological source
It consist of dried leaflets of Cassia angustifolia known as
indian senna belonging tofamily Leguminosae
.
Geographical Source
inndian senna cultivated in
tinnevelley, madurai, ramnathpuram districs in Tamilnadu
, kaddapa dist in Anthrapradesh
, Kutch in Gujarat and Rajasthan
Senna
60. 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.
61. 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.
62. colour- yellowish green
odour- none
taste- mucilaginous, bitter and charecterstic
shape- lance-ovoid flattened, obtusely edged( not pointed)
size- 7-8 mm width, 25-60 mm length
63.
64.
65. (a) Dog senna ie; Cassia abovata,
(b) Palthe senna ie; Cassia auriculata d, and
(c) Arabian Senna or Mecea senna or Bombay senna
i.e.; wild variety of Cassia angustifolia Vahl. from
Southern Arabia.
Dog senna: It contains approximately 1% of
anthraquinone derivatives.
Palthe senna: It contains no anthraquinone glycosides
Arabian senna : It is brownish-green in appearance.
66. Synonyms: Musabbar, Kumari, Korfad, Aloe vera
Biological source
Aloe is the dried latex of leaves of various species of Aloes,
namely:
Aloe vera Linn (Indian Aloe)
Aloe barbadensis Miller (or Curacao Aloe);
Aloe ferox Miller (or Cape Aloe);
Aloe africana Miller and Aloe spicata Baker (or Cape Aloe).
Aloe perryi Baker (or Socotrine Aloe);
All these species belong to the family Liliaceae.
Aloe
67. Geographical Source
Curacao, Barbados, Aruba and Bonaire (West Indian Islands)
Curacao Aloes or Barbados Aloes
Cape Town (South Africa): Cape Aloes
Socotra and Zanzibar Islands: Socotrine or Zanzibar Aloes
68. Cultivation and collection
Propagation is done from 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.
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.
69. Preparation
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.
70. Preparation
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.
71. Preparation 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.
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.
72.
73.
74. Microscopy
It is useful for identification of powdered aloes. it is studied in
lacto phenol reagent to gradually solubilize particles so
crystals can clearly seen
curacao aloes
fragments consist of large number of very small needle or
slender prisms
cape aloes
transparent, brown, angular or irregular fragments.
socotrine aloes
fragments consist of large prisms in group or dispersed form.
zanzibar aloes
irregular lumps in with modular masses are embedded.
78. Chemical tests
general chemical tests
For this prepare a 0.1% (w/v) aqueous solution of aloes by gentle
heating, add to it 0.5g of Kiesulgur and filter through. Whatman Filter
Paper No. 42 and preserve the filtrate for the following tests:
bromine test- filtrate+ freshly prepared bromin solution= pale yellow
ppt of tetrabromalin
schoenteten,s test (Borax test)- filtrate+ borax shake well until borax
dissolves. few drop of this soluition added in test tube filled with water=
green fluorescence appears.
Modified brontragers test
Brontragers test
79. Special test
these test are to distinguish between varieties of aloe
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
80. 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
81. 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
82. Uses
purgative.
Stronger purgative than all anthraquinon glycosides.
To prevent gripping action carminative can be given.
it is ingredient of compound tincture of benzoin
aloe gel is used for topical application and many cosmetic uses.
83. 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.
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. Chemical constituents
40-50% bland fixed oil,
20% protien,
bitter glycoside -amygdalin(1-3%),
0.5% volatile oil
Amygdalin hydrolyzed to produce benzaldehyde+ hydrocyanic
acid.
Hydrocyanic acid is very poisonous hence it is not used
internally.
sweet almond do not contain amygdalin
88. Uses
oil is demulcent ,
In perfumary,
in preparation of bitter almond water,
sedative
91. 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