Lab No. 2 - Flavonoids + Anthracenes

LAB NO: 2
Glycosides
 Glycosides are products of the secondary metabolism of plants by the sugar (glycone
part) is bound to other organic molecules (aglycone) by a glycosidic bond. Glycosides
gives one unit of water molecule when they form.
 The first glycoside found is Salicin. It is obtained from the bark of the willow tree (Salix purpurea
L.)
 Glycosides are found in vacuoles in dissolved form in cell sap. (Fluid found in the vacuoles)
 They are generally solid, crystalline or amorphous, non-colored, bitter-tasting

substances. But some glycosides can have color like; antracenes have yellow-orange,
flavonoids have yellow color and anthocyanins are purple-red.
 Glycosides generally dissolves in water, methanol, ethanol aceton and ethyl acetate but
not dissolved in petroleum ether or ether.
 Almost all glycosides are soluble in 70-90° alcohol.
 The solubility of glycosides in water is different, i.e. they dissolve rapidly in water
containing 2-3 molecules of sugar, whereas glycosides with more sugar molecules
dissolve slowly in water.
 The most important common feature of glycosides is that they all are hydrolyzed with acids
and enzymes. The hydrolysation in acids takes a short time, has quick results, and total
hydrolysis. 1%, 5%, and 10% diluted solutions of acid hydrolyzed mineral acids (hydrochloric
acid, sulfuric acid) are used for acid hydrolysation of glycosides.
 In glycosides, if the saccharide’s reduction unit is bound with the -OH group of an aglycone
(alcohol or phenol), then, these are called “O”-glycosides. If bound with a -SH group of an
aglycone (thiole), then, “S”-glycoside and if bound with a -NH2 (amine) group, then, it is called
“N”-glycoside. Later studies on glycosides have shown that glycosides with a carbon atom
linkage exist as well. These are than called “C”-glycosides.
Page |1
 Glycosides can be classified according to glycone, aglycone part and type of glycosidic bond.
*Hydrolysis: By using H2O larger molecules are breaking down into smaller molecules.
Page |2
Classification of Glycosides according to type of glycosidic bond:
I. Oxygen Glycosides
I. a. Alcohol Glycosides
• Cyanogenic Glycosides
I. b. Phenol Glycosides
• Simple Phenol
• Anthracene Glycosides
• Flavone Glycosides
• Anthocyanins
• Coumarins
• Lignans
I. c. Steroid Glycosides
• Cardioactive Glycosides
• Saponin
Steriodal and Triterpenic Saponins
II. Nitrogen Glycosides

III. Carbon Glycosides
IV. Sulphur Glycosides
Page |3
How to determine sugar, aglycone and glycosidic bond of a glycoside?
Page |4
What is the difference between alcohol and phenol glycoside?
Page |5
Anthracene Derived Glycosides
 Anthracene glycoside (also called as anthraquinone glycosides) consists of glycogen
(sugar) asglucose, rhamnose or either.
 Aglycone parts can be anthraquinones, anthranols, anthrones. Anthracenes naturally

occurs in Rhamnaceae, Rubiaceae, Fabaceae families.
 Anthracene glycosides are found in three types in plants; oxantrone,

anthron and anthraquinone.
Page |6
 Upon hydrolysis they yield their aglycone parts.
 Anthraquinones take about 10hours to produce an effect.
 Should not be used for more than 10 days.
 Should not be used by children, pregnant and lactating women.
 Aloe, senna (senna contains mainly two anthraquinone glycosides called as Sennoside
A and Sennoside B) are two commonly known plant example and they have laxative
effect because oftheir anthracene composition.
Adding Alkali
 To identify Anthracenes mostly 2 chemical tests are used
Borntrager Test
General Anthracene structure
Glycone (Sugar part)
General structure of Anthracene Examples for Anthracene Glycosid
Page |7
Flavonoid Glycosides
 Flavonoids are a group of plant secondary metabolites.
 Flavone glycosides are the glycosides of flavonoids, which are the derivatives of chromones.
Chromones are benzo-γ-pyrones and cannot be found as a free molecule in plants.
Chromone
 These substances forms the many colored compounds in plants. More the hydroxyl groups in a
compound, higher the pH of the medium, darker the color to be observed.
 Yellow coloration increases when OH and pH increases.
 Mostly they’re found in Rutaceae, Fabaceae, Apiaceae families.
 They are plant pigments.
 Flavonoids are responsible for color of flowers, fruits or sometimes leaves.
 They provide tissue protection against UV and have antioxidant effects
 Flavonoids are polyphenolic molecules containing 15 carbon atoms and are soluble in
water and alcohol.
 Aglycone parts are dissolved more in ether and less in water.

Page |8
 Dissolves in alkalines by giving yellow color and after adding acid color disappears.
 Classified depending on degree of oxidation of central pyran ring.
1
2
Flavon means; 2-phenylchromone;
Page |9
P a g e | 10
Lab No 6
Anthracene Derived Glycosides
Microsublimination Test
Plant Sample: Sennae folium
Senna + NaOH gives red color after heating. Free anthraquinone (aglycone part in anthracene)
soluble inalkali and turns to red color.
Flavonoids:
Plant sample: Citrus sinensis
 General test for flavonoids (depend on color changes):

• Flavonoid + FeCl3 Green or blue black
• Flavonoid + NaOH Bright yellow
• Flavonoid + Lead acetate Yellow to orange
• Cyanidin Reaction: Test to identify flavonoid groups. Flavonoids (color pigments) are
decomposed in alcoholic solution with HCl and Mg.
Orange color Flavons
Red Flavonols
Purple Flavonones
P a g e | 11
Cyanidin – Shinoda test is type of reduction reaction (Clemmensen reduction). The metal
supplies the electrons and the HCl acid supplies the protons to achieve the carbonyl reduction.
This test is based on the reduction reaction of flavonoids in the presence of Mg-HCl. Shinoda
chemical test convert flavonoidsinto their flavylium salt.
P a g e | 12

Lab No. 2 - Flavonoids + Anthracenes

Uploaded by

Copyright:

Available Formats

Lab No. 2 - Flavonoids + Anthracenes

Uploaded by

Document Information

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Lab No. 2 - Flavonoids + Anthracenes

Uploaded by

Copyright:

Available Formats

LAB NO: 2

 They are generally solid, crystalline or amorphous, non-colored, bitter-tasting

 Almost all glycosides are soluble in 70-90° alcohol.

Steriodal and Triterpenic Saponins

II. Nitrogen Glycosides

 Anthracene glycoside (also called as anthraquinone glycosides) consists of glycogen

(sugar) asglucose, rhamnose or either.

 Aglycone parts can be anthraquinones, anthranols, anthrones. Anthracenes naturally

 Anthracene glycosides are found in three types in plants; oxantrone,

 Anthraquinones take about 10hours to produce an effect.

 Should not be used for more than 10 days.

 Should not be used by children, pregnant and lactating women.

Glycone (Sugar part)

General structure of Anthracene Examples for Anthracene Glycosid

 Flavonoids are a group of plant secondary metabolites.

 Yellow coloration increases when OH and pH increases.

 Mostly they’re found in Rutaceae, Fabaceae, Apiaceae families.

 They are plant pigments.

 Flavonoids are responsible for color of flowers, fruits or sometimes leaves.

 They provide tissue protection against UV and have antioxidant effects

 Aglycone parts are dissolved more in ether and less in water.

 Classified depending on degree of oxidation of central pyran ring.

Plant Sample: Sennae folium

Plant sample: Citrus sinensis

 General test for flavonoids (depend on color changes):

Orange color Flavons

You might also like