Glycosides are organic compounds that contain a sugar and non-sugar component. Upon hydrolysis, they separate into a sugar and aglycone. Glycosides are classified based on their aglycone component and sugar linkage. Examples discussed include cardiac glycosides like digitoxin, anthraquinone glycosides like aloe, saponin glycosides like glycyrrhiza, and others. The document provides details on the botanical source, parts used, constituents, and uses of various important glycosides.

2. GLYCOSIDES
BY ; RABIA SALEEM

3. GLYCOSIDES
 DEFINATION:
Glycosides are non-reducing organic compounds, upon
hydrolysis they yield;
1. A sugar ; (or glycone, formed of one or more sugar units)
2. A non-sugar moiety; (also called aglycone or genin)
ROH + HOX ROX + H2O
(sugar) (aglycone) (glycoside)
The sugars which are commonly found in glycosides are glucose,
digitoxose (in digitoxin) and rhamnose.

4. GLYCOSIDES
 PROPERTIES:
Chemically glycosides are sugar ethers. In pure,state glycosides
are mostly levorotatory, crystalline, colourless, bitter.They are soluble in
alcohol and water. Insoluble in other organic solvents (pet.ether,
chloroform)
 FUNCTIONS:
They play important role in the life of plants involving
regulatory, transportary and protective functions.
 HYDROLYSIS:
• They are hydrolyzed by acids, alkalis or enzymes resulting in cleavage
of glycosidic linkage.
• The therapeutic efficacy of glycosides is due to Aglycon.The sugar
helps to carry the aglycone to the site of organ or tissue where action
is required.

5. GLYCOSIDES
 NAMING OF GLYCOSIDES:
• Most glycosides may be named according to the plant from which
they are isolated from & include suffix “_in ”:
 Aloin from Aloe vera
 Barbaloin from Aloe barbadensis
 Frangulin from frangula
 Glycyrrizin from glycyrrhiza
 Digitoxin from digitalis
 Cascaroside from cascara
• Depending upon the stereochemistry of glycosidic linkage, there
are two isomeric forms…..α & β. In plants, only the β-form of
glycosides occurs.

6. CLASSIFICATION OF GLYCOSIDES
(on the basis of Glycosidic linkage)
 O- Glycosides ; In these glycosides the sugar part is linked with a
Oxygen atom of aglycone. E.g. Digitoxin (cardiac), sennoside
(anthraquinone), Salicin.
 S- Glycosides; In these glycosides the sugar part is linked with a
Sulfar atom of thiol group of aglycone. E.g. Sinigrin (Isothiocyanate
glycosides)
 N- Glycosides; In these glycosides the sugar part is linked with a
Nitrogen atom of amino group of aglycone. E.g. Snucleosides,DNA,RNA.
 C- Glycosides; In these glycosides the sugar part is linked
(condenced) directly to Carbon atom of aglycone. E.g. aloin, Barbaloin,
Cascaroside, flavonoids.

7. CLASSIFICATION OF GLYCOSIDES
(on the basis of aglycone part, chemical classification)
(a) Cardioactive glycosides: Digitalis, Strophanthus and white squill
(b) Anthraquinone glycosides: Cascara, Aloe, Rhubarb, Cochineal and
Senna
(c) Saponin glycosides: Glycyrrhiza, Sarsaparilla
(d) Cyanophore glycosides: Wild cherry
(e) Isothiocyanate glycosides: Black Mustard
(f) Lactone glycosides: Cantharide
(g) Aldehyde glycosides: Vanilla
(h) Miscellaneous glycosides: Gentian, Quassia, Dioscorea

8. CLASSIFICATION OF GLYCOSIDES
(on the basis of therapeutic activity of aglycone)
 Cathartics------Senna, Casia, Cascara bark,
aloe.
 Cardiotonics----- Strophanthus, Digitalis.

9. CLASSIFICATION OF GLYCOSIDES
(on the basis of sugar uses)
 If the sugar is glucose the glycosides are
called….”GLUCOSIDES”
 Similarly “RHAMNOSIDES”…..Rhamnose.
 “GLACTOSIDE”…..Galactose etc.
 “RIBOSIDES”
 “FRUCTOSIDES”

10. A) CARDOACTIVE GLYCOSIDES; STEROLS
 MACHANISM OF ACTION;
 Function of sugar
AGLYCONE
a. Cardenolide
b. Bufanolid
Drugs include;
i. Digitalis
ii. Strophanthus
iii. White squill

11. Cardioactive Glycosides (Cardiotonics)
 Function of sugar; The sugar part renders the
compound more soluble and increase the
power of fixation of glycosides to heart
muscles.
AGYCON; Aglycon have steroidal skeleton.
Two types of aglycon can be distinguished
depending upon whether they are 5-membered
or 6-membered Lactone ring is attached.
Cardenolide (5-membered lactone at place of R)
Bufanolide (6-membered lactone at place of R)

12. 1) DIGITALIS;(foxglove)
B.O; Digitalis purpurea
D. lanata
 FAMILY; Scrophulareaceae
 P.U; Dried leafs.
 COLLECTION;
CONSTITUENTS; 35 glycosides
Digitoxin, Gitoxin, Gitaloxin
Digoxin (only in Digitalis lanata)
Toxicity of Digitalis;
Adultrants of Digitalis;

15. D. lanataD. purpureaDerivatives
Acetyl digitoxin
Lanatoside A
(Acetyl digitoxin + 1 glucose)
Digitoxin
Glucodigitoxin
(Digitoxin + 1 glucose)
Digitoxigenin
Lanatoside B
(Acetyl gitoxin + 1 glucose)
Gitoxin
Glucogitoxin
(Gitoxin + 1 glucose)
Gitoxigenin
Lanatoside E
(Acetyl Gitatoxin + 1 glucose)
GitatoxinGitatoxigenin
Digoxin
Acetyl digoxin
Lanatoside C
(Acetyl digoxin + 1 glucose)
Deslanoside
(Digoxin + 1 glucose)
Digoxigenin

16. 2) STROPHANTHUS
B.O; Strophanthus kombe
S. hispidus
 FAMILY; Apocynaceae
 P.U; Dried ripe seeds.
VARITIES;
 COLLECTION;
 CONSTITUENTS; Strophanthin, fixed oils(30%)
Nitrogen bases(trigonellin, choline), Resins/ mucilage.
 USES;
1) Cardiac stimulant & Cardiac tonic
2) diuretic, arrow poison.

17. 3) WHITET SQUILL
B.O; Urginea maritima
 FAMILY; Liliaceae
 P.U; Dried fleshy scales of bulb.
 COLLECTION;
 CONSTITUENTS; Scillaren →
Scillarenin + sugar (glucose+ rhamnose)
 USES;
1) Cardiac tonic
2) diuretic.
3) Expectorant
4) emetic.

18. B) ANTHRAQUINONE GLYCOSIDES;
 Anthraquinone glycosides upon hydrolysis yield aglycone which are di,
tri or tetra hydroxyl anthraquinone or derivatives of these compounds.
 Mostly found in dicot plants.
These compounds are stimulant, cathartic or purgative and they are
exert their action by increasing the tone of muscles in wall of large
intestine.
Drugs include;
i. Aloe
ii. Rhubarb
iii. Cascara
iv. Senna

20. 4) ALOE;
 B.O; Aloe barbadensis
Aloe perryi
 FAMILY; Liliaceae
 P.U; Dried juice of leaves.
 COLLECTION;
 CONSTITUENTS; Aloin, barbaloin (C-glycoside)
 USES;
1) Purgative, Cathartic.
2) juice is used for skin burns & skin irritations.
3) used in sunscreen lotions, cosmatic preparations.
4) Benzoin tincture.

21. 5) CASCARA;
B.O; Rhamnus purshian
Cascara sagarada
 FAMILY; Rhamnaceae
 P.U; Dried bark.
 COLLECTION;
CONSTITUENTS; Chrysaloin,
CascarosideA & B,Cascaroside C & D
 USES;
1) Purgative, Cathartic.
2) Veternary medicines.

22. 6) RHUBARB;
B.O; Rheum officinale
Rheum emodi
 FAMILY; Rhamnaceae
 P.U; Dried Rhizome & roots.
 COLLECTION;
CONSTITUENTS; Rhein,Emodin,
aloe-emodin & chrysophenol.
 USES;
1) Purgative, Cathartic.
2) Veternary work.

23. 8) SENNA;
B.O; Cassia acutifolia
C. angustifolia
 FAMILY; Leguminoseae
 P.U; Dried leaflets
 COLLECTION;
CONSTITUENTS; Sennoside A& B,
Sennoside C & D.
 USES;
1) Purgative for chronic constipation.

24. C) SAPONIN GLYCOSIDES ;
 Plant containing Saponins have long been used as detergents e.g. roots of
Saponaria officinalis, bark of Quilaga saponaria.
 Diagnostic Characteristics of SAPONINS;
1. They form colloidal solutions with water.
2. They have bitter taste except Glycyrrhiza, which is very sweet in taste.
3. They destroy RBCs by hemolysis.
4. They are toxic specially to cold blooded animals… Fish poison.
 Classification; (On the basis of aglycones)
i. Steroidal saponins
ii. Pentacyclic triterpenoids.

25. C) SAPONIN GLYCOSIDES ;
Drugs include;
i. Glycyrrhiza
ii. Sarsaparilla
iii. Ginseng

26. 9) GLYCYRRHIZA;
B.O; Glycyrrhiza glabra
 FAMILY; Leguminoseae
 P.U; Dried roots & rhizomes.
VARITIES;
1. TYPICA ; Spanish liquorice
2. GLANDULIFERA ; Russian liquorice
3. VIOLUCON ; Persian Liquorice
 COLLECTION;
CONSTITUENTS; Glycyrrhizin, Liquiritin.
 USES;
Demulcent, laxative, Flav agent, expectorant.

27. 10) SARSAPARILLA;
B.O; Smilax ornata
 FAMILY; Lilliaceae
 P.U; Dried roots & rhizomes.
CONSTITUENTS; Sarsaponin &
smilagenin are steroidal aglycon used for
semi-synthetic production of cortisone & steroidal hormones.
 USES;
1) As blood purifier.
2) Anti-rheumatic.
3) Flavouring agent.

28. D) CYANOPHORE GLYCOSIDES ;
Also called Cyanogenic glycosides.
They yield Hydrocyanic acid (HCN) upon hydrolysis, medicinal
activity is also due to HCN.
 Mostly present in plants of family Rosaceae.
 For examples Amygdalin obtained from bitter almonds,
Prunasin obtained from wild cherry bark.
Drugs include;
i. Almond
ii. Wild cherry

29. 11) WILD CHERRY;
B.O; Prunus serotina
 FAMILY; Rosaceae
 P.U; Dried bark.
COLLECTION;
CONSTITUENTS; Prunacin.
Scopoletin, starch,resins,tannins, Gallic acid.
Leaves also contain Amygdalin.
 USES;
1. Astringent tonic
2. Sedative
3. expectorant (has been used in bronchitis) & horrible cough.

30. E) ISOTHIOCYANATE GLYCOSIDES ;
These are sulpur-containing compound rich in family Cruciferae.
These glycosides are generally irritant and hence used externally
as counter irritant.
 For examples Sinigrin obtained from black mustard, Sinalbin
obtained from White mustard.
Drugs include;
i. Mustard.

31. 12) BLACK MUSTARD; Sarson
B.O; Brassica nigra
 FAMILY; Cruciferae(Brassicaceae)
 P.U; Dried riped seeds.
CONSTITUENTS; Sinigrin.
Allyl isothiocynate (V.oil), fixed oils.
 USES;
1. As edible oil after refining/ condiment.
2. Local irritant.
3. emetic
4. rubefacient & vesicant (externally)

32. F) LACTONE GLYCOSIDES ;
Drugs include;
i. Cantharide.

33. 13) CANTHARIDE;
Z.O; Cantharis vesicatoria
 FAMILY; R
 P.U; Dried insects.
 COLLECTION;
CONSTITUENTS; Cantharidine
Fats,Fixed oils, uric acid, acetic acid.
 USES;
1. Vasicant.
2. Counter irritant
3. Rubifacient.
4. Hair tonic to stimulate hair growth (Spanish oil)
5. As Keratolytic agent to treat warts.

34. G) ALDEHYDE GLYCOSIDES ;
Drugs include;
i. Vanilla.

35. 14) VANILLA;
B.O; Vanilla planifolia
 FAMILY; Orchidaceae
 P.U; Vanilla pods (cured fully grown but unripe fruits)
 PREPRATION;
CONSTITUENTS; Gluco-vanillin(vanilloside).
glucovanillinic acid (these are present before curing)
 USES;
1. In confectionery as flavouring agent.
2. In Perfumery.

36. H) MISCELLANEOUS GLYCOSIDES ;
Drugs include;
i. Gentian.
ii. Quassia.
iii. Dioscorea.

37. 15) GENTIAN;
B.O; Gentiana lutea
 FAMILY; Gentianaceae
 P.U; Dried unfermented rhizome & roots.
CONSTITUENTS; Gentiopicrin.
gentinin, fixed oils, tannins, sugars.
 USES;
1. As Bitter tonic (quickly dried drug) in anorexia & dyspepsia.
2. As flavouring agent (slowly dried drug).
3. anthelmintic, anti-inflamatory, antiseptic, emmenagogue,
febrifuge, cholagogue, refrigerant & stomachic.
4. prescribed for the patients with gastric & duodenal ulcers.

38. 16) QUASSIA; bitter wood,Jamaica quassia
B.O; Picrasma excelsa
 FAMILY; Simarubaceae
 P.U; Dried wood
COLLECTION;
CONSTITUENTS; Quassin, Neoquassin,
Isoquassin (picrasmin) , woody fiber, v.oils, pectin.
 USES;
1. Pure bitter tonic & stomachic.
2. As insecticide
3. As an enema for expulsion of thread worms (vermifuge).

39. 17) DIOSCOREA; YUM
B.O; Dioscorea spiculiflora
 FAMILY; Dioscoreaceae
 P.U; Dried roots & rhizome
COLLECTION;
CONSTITUENTS; Diosgenin (steroidal sapogenin)
Smilagenin, yammogenin, phenolic compounds & starch.
 USES;
1. Diosgenin is used as precursor for the production of progesterone &
other steroid drugs.
2. In disorders of genitary organs.
3. Asthma & arthritis.
4. Dioscorea is an imp staple food crop grown in west Africa.