2° METABOLITES

PART II

Semester - 3
Pharmacognosy & Phytochemistry I

Prepared By:
Ms. Priya Shah
Department of Pharmacognosy
L.J. Institute of Pharmacy
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TANNINS

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Definition
 Tannins are complex, organic, non nitrogenous, poly
phenolic substances.

 They having high molecular weight.

 They are widely distributed in Plants.

 They are used as antiseptics and in GIT diseases like

diarrhoea and also used in leather industries.

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Properties- Physical
Non crystalline, amorphous compounds
Pale yellow to light brown-red in color
Astringent Property
Unstable in presence of light and moisture
Forms colloidal solution with water and they have acidic
reaction due to polyphenols.
 Widely used in tanning leather, dyeing fabric, and
making ink.
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Properties- Chemical

Soluble in dilute alkalis and alcohol

Insoluble in organic solvent

It precipitates with heavy metals

It also precipitates with potassium dichromate solution

It shows color reaction with Fe salts

Anti oxidizing agents

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Importance
Medicinal Biological Industrial
Uses Activities Uses
Antidote Inhibition of Lipid
Ink manufacturing
peroxidation

Antioxidant
Decrease nitrogen
content in blood Preservative
urea
Antiseptic

Inhibition of
Leather industry
Astringent Plasmin

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Classification
Tannins

True Tannins Pseudo tannins

Hydrolysable Condensed Complex

Tannins Tannins Tannins

Galli tannins Ellagi Tannins

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Structure

Gallic Acid Ellagic Acid Pyrogallol

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Difference
Hydrolysable Tannin Condensed Tannin

Non Hydrolysable tannins, Catechol

Hydrolysable Tannins, Pyrogallol tannins
tannins, Phloba tannins
Sugar moiety is present attached by ester
Sugar moiety is absent
linkage

Hydrolysed by enzyme or acid and on Treated with mineral acid and enzyme
hydrolysis produced Gallic acid and Ellagic forms polymerized complex known as
acid. Phlobaphenes.

On distillation Gallic acid converted to

They produce Catechol or Catechin
Pyrogallol.
With FeCl3 , it gives blue color. It gives brownish green color.

On basis of Phenolic acid it produces Catechin is Flavan 3-ol having similar

Gallotannins and Ellagitannins. structure like Proanthocynidine.
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Identification tests
1. Gold beater’s skin test:
Gold beater’s skin is a membrane prepared from intestine
of Ox. Soak a small piece of Gold beater’s skin in 2%
hydrochloric acid. Rinse it with distilled water. Place it in
solution to be tested for 5 minutes. Wash in water and
transfer to 1% solution of ferrous sulphate.
Black or brown color of skin indicates presence of
tannins.
It is a quantitative test and +ve only for true tannins 10
2. Matchstick test:

 Dip matchstick in plant extract. Dry it. Moisten it with

hydrochloric acid. And warm near flame.

 Wood will turn pink or red in color due to

Phloroglucinol.

3. Gelatin test:

 Solution of tannin (0.5%-1%) precipitates 1% solution

of gelatin containing 10% sodium chloride.
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4. Catechin test:
 Catechin when heated with acid produce
phloroglucinol.
 Phloroglucinol can be detected with matchstick test.
5. Test for Chlorogenic acid:
 Treat extract containing chlorogenic acid with
aqueous ammonia and expose it to air.
Green color will appear gradually.

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Chemical Tests for Pale Catechu
1. Gambier fluorescin test:

Take alcohol extract of drug, a little sodium hydroxide

is added and shaken with petroleum ether.

The petroleum ether layer shows green fluorescence.

Black catechu gives negative test.

2. A matchstick test : Positive

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3. Vanillin-hydrochloric acid test:

Drug shows pink or red colour with a mixture of

vanillin:alcohol:dilute HCl in the ratio 1:10:10.

The reaction produces phloroglucinol which along with

vanillin gives pink or red colour.

4.Test for chlorogenic acid: Positive

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Questions
1. Define tannins. Write a note on properties and
chemical tests of it.

2. Differentiate between Hydrolysable tannins and

Condensed tannins.

3. Differentiate between True tannins and Pseudo tannins.

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RESINS

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Introduction
 The term ‘resin’ is amorphous, transparent or
translucent solid, semisolid or liquid products of
complex chemical nature.
 These are amorphous mixtures of essential oils,
oxygenated products of terpenes and carboxylic acids.
 On heating get soften then melt & form clear adhesive
fluids.
 Occur in schizogenous or schizolysigenous cavities or
ducts.
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General properties-Physical
 All resins are heavier than water , they are usually
amorphous, hard, and brittle solids.
 They are insoluble in water and usually insoluble in
petroleum ether but soluble in organic solvents like
alcohol, ether, acetone, chloroform and ether.
 They are hard, electrically non-conductive &
combustible (flammable) masses.
 High molecular wt. compound.
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Chemical Properties
 Resins are often associated with volatile oils (oleoresins),
with gums (gum-resins) or with oil and gum (oleo-gum-
resins).
 Chemically, resins are complex mixtures of resin acids,
resin alcohols (resinols), resin phenols (resinotannols),
esters and chemically inert compounds known as resenes.
 Many resins ,when boiled with alkalies yield soaps which
are called as resin soaps.

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Classification

Resin

Chemical Occurrence of
Taxonomical Classification Resin with
Resin Association of other group of
Chemical group Compounds

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1. Taxonomical classification,

Examples

 Berberidaceae resins. (Podophyllum)

 Coniferous resin( Colophony)

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2. Classification according to chemical constituent;
Examples
 Acid resins (Colophony),
Ester resins (Benzoin),
Resin phenols (Tolu Balsum),
Resin Alcohol (Peru),
Glycoresin (Podophyllum),
Resene resins (Asafoetida) , etc.

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3. Occurrence or association of resin with other
group of compounds

Oleo resin- Ginger, Turmeric

Gum Resin- Gamboage

Oleo Gum Resin- Myrrh, Asafoetida

Gluco Resin- Jalap

Balsams- Balsam of Peru, Balsam of Tolu

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Preparation
1.Natural resins:
The resins are called preformed or normal or
physiological resin.
Examples:
Schizogenous gland in Clove
2. Abnormal Resins:
The resin is known as abnormal, pathological resin.
Examples: Benzoin, Tolu balsams, Storax
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Isolation methods
 Extraction with alcohol and precipitation with water:
E.g. Jalap, Ipomoea

 By steam Distillation for seperation of oil.

E.g.: Colophony

 By heating the plant part. E.g.: Guaiacum

 Collecting Fossil resin. E.g. Copal

 Processing the encrustraction. E.g. Shellac

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Identification Tests

 Physical Parameters

 Examination of powder

 Chemical identification: Iodine value,

Saponification value, Acid value etc..

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FLAVANOIDS

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Introduction
 They are polyphenolic compounds possessing 15
carbon atoms; two benzene rings joined by a linear
three carbon chain having the carbon skeleton C6 -
C3 - C6.

They are the plant pigments

Having polar nature and

It is solouble in methanol and water.

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Contd…
Many flavonoids are easily recognised as flower
pigments in most angiosperm families (flowering
plants).

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Structure

Their basic structure is a skeleton of diphenylpropane,

namely, two benzene rings (ring A and B, see figure)
linked by a three carbon chain that forms a closed
pyran ring (heterocyclic ring containing oxygen,the C
ring) with benzenic A ring.
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Classification
Flavonoids are classified in 6 major subgroups
depending on the carbon of the C ring on which B ring
is attached, and the degree of unsaturation and
oxidation of the C ring.

Classification and Chemistry of Flavonoids.

B ring is linked in position 3

of the ring C isoflavones.

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Contd…
If B ring is linked in position 4- Neoflavonoids.

If C ring is opened –Chalcone.

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Contd...
If B ring is linked in position 2 , flavones, flavonols,

Flavanones, flavanols,catechin, and anthocyanidin.

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Flavonoids & their examples
 Flavone:- Luteolin, Apigenin, Tangeritin

 Flavonol:- Quercetin, Kaempferol, Myricetin,

Fisetin, Isorhamnetin, Pachypodol, Rhamnazin

 Flavanone:- Hesperetin, Naringenin, Eriodictyol,

Homoeriodictyol

 Flavanonol- Taxifolin, Dihydrokaempferol

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Souces

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Role of flavanoids in plants
 Phenylpropanoids, act as key chemical modulators of
plant communication with insects and microbes,
either as attractants or repellants , or as phytoalexins
against pathogens and herbivores.

 Induce root nodulation when excreted by symbiotic

nitrogen-fixing Rhizhobia.

 Role of Flavonoids In Plant Defense

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Role of flavanoids in plants
 Derivatives of the initial phenylpropanoid play vital
roles in plant structural integrity, protection against
UV radiation and phytopathogens, internal regulation
of plant cell physiology and signaling.

 Some flavonoids provide stress protection, for

example act as scavengers of free radicals such as
reactive oxygen species (ROS), as well as metal
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chelating agents that generate ROS.
Chemical Tests
Shinoda test:

dried extracts/ powders + in 95% ethanol (5ml) + few

drops of concentrated hydrochloric acid (HCL)+
magnesium turnings pink color.

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Contd…
Lead acetate solution test: To small quantity of above

residue, lead acetate solution was added and observed

for appearance of formation of yellow colored
precipitates.

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Benefits
 Reduced risk of cardiovascular diseases.

 Reduction in Blood Pressure due to its vasodilatory

effect.

 Delays or prevents the onset of diseases caused by

free radicals

 Best antioxidant

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Contd…
Anti-inflammatory activity

Improvement of endothelial functions

Inhibits LDL oxidation by free radicals

Inhibits platelet Aggregation

Antiviral

Antibacterial

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FAQs
1. Define resins. Give properties, classification and
isolation method of it. (May 2011) (January 2016,
December 14, January 2016, June 2015, June 2013)
2. Define and explain Resin, Rosin, Resenes and
Resinols with proper examples. (January 2013)
3. Write a note on flavanoids.

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THANK YOU

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