Glycosides Classification

Classification
• On the basis of aglycone structure
• [3] Anthracene derivatives (purgatives)
• can cause side effects and adverse reactions but
not death
 Anthracene glycosides
• found in several plant drugs
• occur in glycoside form
– and less commonly in aglycone form
• based on anthracene molecule

Anthracene glycosides are chiefly found in dicot plants

but to some extent it is also found in monocot and lower
plants. It consists of glycosides formed from aglycone
moi-eties like anthraquinones, anthranols, anthrones
• 3 oxygenated or substituted forms of the
anthracene molecule exist

Anthraquinone Anthrone (reduced form

(most common) occurring in plant) Dianthrone
(reduced dimer)
• Examples

Rhein anthraquinone Chrysophanol…………

Chrysophanol is a 1,8-dihydroxy-3-methyl
derivative of the 9,10-anthracenedione
ring. This compound is widely distributed
in several organisms, including plants,
microbes, and insects
 Aloe-emodin………...
Aloe emodin (1,8-dihydroxy-3-
(hydroxymethyl)anthraquinone) is an
anthraquinone present in aloe latex, an
exudate from the aloe plant
Emodin……………..
Emodin (6-methyl-1,3,8-
trihydroxyanthraquinone) is a naturally
occurring anthraquinone derivative found in
roots and leaves of various plants, fungi.
For a long time it has been used in
traditional Chinese medicine as an active
ingredient in herbs
 Extraction
• most quite polar--due to phenols and sugars
• water or alcohol or mixtures of them used
• dried plant material percolation in industrial columns
with dilute alcohol
• tincture produced
• partitioned with chloroform/ether to clean up
(remove green pigment, fats, lipids)
• clean yellow tincture subjected to column
chromatography
• gradual elution of individual glycosides
• crystallized for purity
• Purification of glycoside makes them expensive
products
– use a clean tincture to make a dry extract
– used for granules in tablets
– standardize final tablet
 • Identification:

– easy – colored orange-yellow

– chemical test: Borntrager’s test

(in alkali (KOH/ NH3) phenolic groups -> phenate complex

(bright red))
Borntrager’s test
TLC using silica gel – plates do not have to be sprayed
since yellow but can confirm with KOH (red spot)
Potency:
Potency is an expression of the activity of a drug in terms of the
concentration or amount of the drug required to produce a
defined effect, whereas clinical efficacy judges the therapeutic
effectiveness of the drug in human

– anthrone > anthraquinone> dianthrone

 Assay

• An assay is an investigative or analytic

procedure for assessing or measuring the
presence, amount, or functional activity of a drug
(the analyte)

• Isolating each active component too expensive

– powdered plant material (tablets or capsules)
– or aqueous (fluid) extracts used
chemical assay
– spectroscopy – quick and cheap

• To remove aglycones
– make an extract, shake with ether
• discard ether phase containing free
aglycones
– then acid hydrolyse aqueous phase
containing glycosides
• with ferric chloride for direct C- bonds
• and with dilute HCl
– extract in CHCl3 (Chloroform)(using
separatory funnel)
• gives aglycones from glycosides
Senna
dimer can be split into two parts with FeCl 3 hydrolysis
Reduction of sennosides A and B to pharmacologically active rhein
 –O- and C- linkages
To get aglycones: use FeCl3 + HCl
Official anthraquinone drugs in B.P and U.S.P.:
1- Senna leaf & senna fruit (pod).
2- Aloes.
3- Cascara tablets, elixir, dry exract, liquid extract.
4- Rhubarb powdered, tincture.
5- Danthrone
6- Frangula bark
H.w: check them in google
Danthrone

Frangula bark ‫نبات النبق‬