Flavonoids: Introduction

Flavonoids
•The flavonoids are polyphenolic compounds possessing 15 carbon atoms;
two benzene rings joined by a linear three carbon chain having the carbon
skeleton C6 - C3 - C6 and they are the plant pigments and they are having
polar in nature and soluble in methanol and water.

• Flavonoids constitute one of the most characteristic classes of compounds

in higher plants. Many flavonoids are easily recognized as flower pigments
in most angiosperm families (flowering plants).

•However, their occurrence is not restricted to flowers but include all parts
of the plant.

•They are secondary metabolite and effective in CNS disorders.

 Tests for flavonoids

 The extracts were dissolved in ethanol, filtered and

subjected to following tests.

 Shinoda test: The dried extracts were dissolved in 95%

ethanol (5ml) and few drops of concentrated hydrochloric
acid (HCL) were added. Then the magnesium turnings
were put into the solution and observed for appearance of
pink color.
 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.
 Flavonoids
The Most Important Classes of Flavonoids and their Biological
Significance

number of known biological significance

class
members (so far as known)

 Polyphenolic compounds anthocyanin(s) 250 red and blue pigments

with 15 C atoms, 2 benzene
rings on linear 3 C chain chalcons 60 yellow pigments

 Over 4,000 flavonoids

aurones 20 yellow pigments
 Easily recognized as flower
pigments in most angiosperm cream-coloured
flavones 350
plants but are not always flower pigments of flowers

pigments feeding repellents (?)

flavonols 350
 In plants they repair damage in leaves
and shield from environmental
dihydrochalcons 10 some taste bitter
toxins
proanthocyanidins 50 astringent substances

some have properties

catechins 40
like those of tannins

oestrogen effect, toxic

isoflavonoids 15
for fungi
 Core structures and nomenclature
A
OH
B

Chalcone

• The nomenclature of flavonoids proper is

straight-forward with the aromatic ring A O
B
O O

condensed to the heterocyclic ring C and A C

OH OH
the aromatic ring B most often attached at O O
the C2 position. The various substituents Flavanone Dihydroflavonol Flavan-3-ol
are listed first for the A and C ring and -
as primed numbers - for the B ring (note
that the numbering for the aromatic rings +
O O O
of the open-chained precursor chalcones
is reversed). OH OH
O O

Flavon-3-ol Anthocyanidin
• (Harborne JB, ed. (1988) The Flavonoids. Flavone

Advances in Research. Chapman & Hall.)

O O

Isoflavone

Neoflavone
 Flavonoids example

 Flavone:- Luteolin, Apigenin, Tangeritin

 Flavonol:- Quercetin, Kaempferol, Myricetin,
Fisetin, Isorhamnetin,
Pachypodol, Rhamnazin
 Flavanone:- Hesperetin, Naringenin,
Eriodictyol, Homoeriodictyol
 Flavanonol- Taxifolin, Dihydrokaempferol
 Other flavonoids
 Chalcone
Chalcone is derived from three acetates and cinnamic acid as shown
below.

 Anthocyanidin
is an extended conjugation made up of the aglycone of the glycoside
anthocyanins. Next to chlorophyll, anthocyanins are the most important
group of plant pigments visible to the human eye.
 The anthocyanodins constitute a large family of differently coloured
compounds and occur in countless mixtures in practically all parts of most
higher plants. They are of great economic importance as fruit pigments
and thus are used to colour fruit juices, wine and some beverages.
 The anthocyanidins in Hydrangea, colours it RED in acid soil and BLUE in
alkali soil.
 Ground plant material
Maceration (3 times)

Aqueous layer
Purification with Chloroform (3 times)

Aqueous layer
Dropwise addition of 10% NaCl solution
and centrifugation

Flavonoids in supernant
Precipitate of tannins liquid
Partioning with ethyl
acetate

Flavonoid obtained by evaporation of ethylacetate layer