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Glycosides

Glycosides are molecules found in plants that contain a sugar component bound to another part. Many plants store important chemicals as inactive glycosides that are activated when the sugar is removed by water and enzymes. The sugar portion is called the glycone and the other part is the aglycone. Glycosides are classified based on the type of sugar or linkage between the sugar and other part. They are identified through tests like the Keller-Kiliani, Baljet, Legal, Raymond, and Kedde tests.

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935 views9 pages

Glycosides

Glycosides are molecules found in plants that contain a sugar component bound to another part. Many plants store important chemicals as inactive glycosides that are activated when the sugar is removed by water and enzymes. The sugar portion is called the glycone and the other part is the aglycone. Glycosides are classified based on the type of sugar or linkage between the sugar and other part. They are identified through tests like the Keller-Kiliani, Baljet, Legal, Raymond, and Kedde tests.

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nilumpharm
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We take content rights seriously. If you suspect this is your content, claim it here.
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GLYCOSIDES

• In chemistry, glycosides are certain molecules


in which a sugar part is bound to some other
part.
• Many plants store important chemicals in the
form of inactive glycosides; if these chemicals
are needed, the glycosides are brought in
contact with water and an enzyme, and the
sugar part is broken off, making the chemical
available for use. Many such plant glycosides
are used as medications.
• These are organic compounds from plants and animal
origin which on enzymatic or acidic hydrolysis gives one
or more sugar moiety (glycone) along with non sugar
moieties (aglycone or genin).

• Sugar moieties present may be single sugar moiety or


more than one but more common is up to 4, mostly
present sugars is β-D glucose.

e.g. for Diglycoside galactose.


Triglycoside digitoxose

• The activity of glycoside is due to the aglycone moiety


• The activity of glycoside increases with the increase
in the sugar moiety.

• A molecule with maximum number of aglycone


moiety is called primary glycoside. These are more
active than secondary and tertiary glycoside. But are
not stable. So we will isolate only secondary
glycosides which are more stable.

• Primary glycosides on hydrolysis yields secondary


(gives two sugar moiety) which on further hydrolysis
gives tertiary glycosides.
• Names of glycosides ends with osides or in, as in
sennoside, cascaroside or digitoxin, glycyrrhizin, aloin.

• Glycosides are crystalline or amorphous substances which are


soluble in water and dilute alcohol but insoluble in organic
solvents.
• Aglycone moiety is soluble in organic solvents like ether,
benzene etc.
• Glycosides are hydrolyzed by enzymes, water and mineral
acids.
• They are optically active many of them are levorotatory.

• They participate in growth regulation and protection of plant.


CLASSIFICATION OF GLYCOSIDES
• Anthracene glycosides : senna, rhubarb, cascara,aloe

• Cardiac glycosides : digitalis,squill, strophanthus, thevetia

• Saponin glycosides : licorice,ginseng, brahmi, shatavari, senega, gokhru

• Flavonol glycosides : citrus fruits, gingko, silamarin

• Cyanogenetic glycoside : bitter almond, wild cherry bark

• Isothiocyanate glycoside : black mustard

• Phenol glycoside : bearberry

• Coumarin & furanocoumarin glycosides : mylabris, visnaga, tonka bean

• Bitter glycoside : gentian, picrorrhiza, chirata, quassia, kalmegh, henna

• Aldehydic glycoside. : vanilla pods


Classification according to the linkage between
aglycone and glycone.

Linkage takes place between –OH group of glycone and hydrogen


from SH, NH,CH and OH to form:

1. C- glycoside :
Glycone –OH+CH-aglycone→glycone-C-aglycone +water.
e.g. anthracene glycoside - aloe,cascara.

2. O-glycoside : e.g. senna, rhubarb,frangula.

3. S-glycoside : Isothiocyanate glycoside , sinigrin from black


mustard

4. N- glycoside : Nucleoside, amino group of base reacts with OH


group of ribose or deoxy ribose to form N-glycoside.
IDENTIFICATION TESTS:
• KELLER KILIANI TEST:-
For deoxy sugars,
The sugar is dissolved in acetic acid containing a trace of ferric chloride
and transferred to conc. sulphuric acid. At the junction of the liquids
reddish-brown colour is produced which gradually becomes blue.

• BALJET TEST:
Substance + alkaline picrate solution →orange colour.

• LEGAL TEST:
Substance + sod nitropruside + pyridine→red colour.

• RAYMOND TEST:
Substance + m-dinitro benzene in methanolic KOH →purple colour.

• KEDDE TEST:
Substance+ 3,5-dinitrobenzoic acid + alkali→ deep blue color.

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