(MIDTERM) Extraction of Saponins Flashcards by Monica Anne Colina

A glycoside is any molecule in which a
sugar group is bonded through its
anomeric carbon to another group via
_______________

GLYCOSIDIC BOND

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The sugar group is known as the
_______ and the non-sugar group as the
_______ or _____ part of the glycoside.

GLYCONE
AGLYCONE
GENIN

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The glycone and aglycone portions can
be chemically separated by hydrolysis in the presence of ____.

ACID

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Classification of Glycosides

On the Basis of Glycone
On the Basis of Glycosidic Linkage
On the Basis of Aglycone

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Latin ____, meaning soap.

SAPO

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Characterized by their property of producing a frothing aqueous solution.

Saponins

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Have hemolytic properties, and when injected into the blood stream, are highly toxic.

Saponins

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Sternutatory

Saponins

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Generally, have acrid, bitter taste.

Saponins

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Have a high molecular weight and a high polarity and their isolation in a state of purity presents some difficulties.

Saponins

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Occur as complex mixtures with the components differing only slightly from one another in the nature of the sugars present, or in the structure of the aglycone.

Saponins

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According to the structure of the aglycone or sapogenin, two kinds of saponin are recognized:

the steroidal (commonly tetracyclic triterpenoids)
the pentacyclic triterpenoid types

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less widely distributed in nature than the pentacyclic triterpenoid type

Steroidal Saponins

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Phytochemical surveys have shown their presence in many families, particularly the:
* Dioscoreaceae (e.g. Dioscorea spp.)
* Agavaceae (e.g. Agave and Yucca spp.)
* Smilacaceae (Smilax spp.)
* Leguminosae (Fenugreek)
* Solanaceae (Steroidal alkaloids in Solanum)
* Species of Strophanthus and Digitalis contain both steroidal saponins and cardiac glycosides.

Steroidal Saponins

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e.g. Dioscorea spp.

Dioscoreaceae

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e.g. Agave and Yucca spp.

Agavaceae

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Smilax spp.

Smilacaceae

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Fenugreek

Leguminosae

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Steroidal alkaloids in Solanum

Solanaceae

Species of ___________________ contain both steroidal saponins and cardiac glycosides

Strophanthus and Digitalis

Rare in monocotyledons.

Pentacyclic Triterpenoid Saponins

In these saponins the sapogenin is attached to a chain of sugar or uronic acid units, or both, often in
the 3-position

Pentacyclic Triterpenoid Saponins

Abundant in many dicotyledonous families, particularly:
* Caryophyllaceae
* Sapindaceae
* Polygalaceae
* Sapotaceae

Pentacyclic Triterpenoid Saponins

Pentacyclic Triterpenoid Saponins
Abundant in many dicotyledonous families, particularly:

Caryophyllaceae
Sapindaceae
Polygalaceae
Sapotaceae

1. Weigh about 10 g of gogo bark and cut into small pieces. 2. Place the gogo bark in a beaker containing 30 ml of distilled water and allow to boil for 10 minutes. 3. Filter and decolorize the filtrate using animal charcoal. 4. Evaporate the clear filtrate to dryness. 5. Add 10 ml of ether, stir and decant off the ether. 6. Weigh the residue left in the evaporating dish

Extraction Process of Saponins

3 Identification Tests

* Based on physical properties of saponins (foam-forming). * Based on chemical properties of saponins (color and precipitation reactions). * Based on biological properties of saponins (hemolysis test).

Based on physical properties of saponins

foam-forming

Based on chemical properties of saponins

color and precipitation reactions

involves shaking an extract with water

Foam-foaming

Based on biological properties of saponins

hemolysis test

Foam-foaming: * involves shaking an extract with water * formation of ____________________

STABLE PERSISTENT HONEY-COMB FOAM (1-2 cm)

formation of STABLE PERSISTENT HONEY-COMB FOAM (1-2 cm)

Foam-foaming

BASED ON CHEMICAL PROPERTIES:

* Barium Hydroxide Test * Lead Acetate Test * Fehling’s Solution Test

formation of WHITE PPT.

Lead Acetate Test

formation of a WHITE PPT. OR THE DEVELOPMENT OF A STABLE FOAM

Barium Hydroxide Test

BASED ON CHEMICAL PROPERTIES:

Liebermann-Burchard Test

formation of RED, ORANGE, OR YELLOW PPT. (GENERALLY BRICK-RED PPT.)

Fehling’s Solution Test

- differential test for steroidal and triterpenoid saponins * Reagents: Acetic anhydride; concentrated sulfuric acid * Blue-green coloration - presence of STEROIDAL saponins * Purple coloration - presence of TRITERPENOID saponins

Liebermann-Burchard Test

Acetic anhydride; concentrated sulfuric acid

Liebermann-Burchard Test Reagents

1. Aglycone portion (hydrophobic) portion binds to lipids (cholesterol and phospholipids) on the RBC cell membrane 2. Increase in membrane permeability, leading to formation of pores (holes) on the lipid bilayer 3. Disrupts osmotic balance due to entry of water, leading to cell swelling 4. Resulting to cell lysis (bursting), leading to release of hemoglobin to solution

Mechanism of Hemolysis

Blue-green coloration

presence of STEROIDAL saponins

BASED ON BIOLOGICAL PROPERTIES:

Hemolytic Test

Purple coloration

presence of TRITERPENOID saponins

Hemolytic Test

* Deep Red Supernatant * Light Red Supernatant * Clear Supernatant

COMPLETE HEMOLYSIS (BETA-HEMOLYSIS)

Deep Red Supernatant

PARTIAL HEMOLYSIS (ALPHA - HEMOLYSIS)

Light Red Supernatant

No Hemolysis

Clear Supernatant