FLAVONOIDS
• Class of plant secondary metabolites
• Word Flavonoids derived from latin word:
“Flavus”= yellow
• Group of polyphenolic compounds which are found
in fruits, flowers, seeds & vegetable
• Structure of flavonoids The flavonoids are
possessing 15 carbon atoms; two benzene rings
joined by a linear three carbon chain the skeleton
can be represented as the C6 - C3 - C6 system.
PROPERTIES OF FLAVONOIDS
Physical Properties Chemical properties:
1. Crystalline solids, sharp MP 1. 15 C skeleton, 2 benzene linked
2. Solubility: in H2O & alcohol by heterocyclic pyran ring
(Flavonoid glycoside) 2.Being phenolic, dissolves in
Non glycosidic flavonoid: alkalies → Yellow sol. +HCl →
Aglycon part-sol. in organic colorless
solvents 3.Glycosidic linkage located at
3. Color: Flavonones, Flavanol, 3 or 7 C
Isoflavones- Colorless
4.Flavanones, Flaonoes are
Flavonols, Flavones: Yellow, unstable compound , on oxidation
Chalchones, aurones: Y, Orange
→ Chalcones, leucocyanidines
Anthocyanidine acid med.: Red
5.Flavonoid + FeCl3→ green/
In basic: Blue
purple/ red brown color
4. Flavanols: optically active
FLAVONOIDS
• The three-carbon (-C3-) may be included through an oxygen
bond between the two phenyl rings into:
1- A five-membered heterocyclic ring (furan) as in aurones.
2- A six-membered heterocyclic ring (pyran) to give flavonoids
which constitute the largest group. The flavonoid aglycone
consists of a benzene ring (A) condensed with a six membered
ring (C) pyran ring, which at 2nd position adds a phenyl ring
(B) as a substituent. C6-C3-C6 structure
CLASSIFICATION OF FLAVONOIDS
• 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.
• B ring is linked in position 3 of the ring C are called isoavones;
• B ring is linked in position 4, neoavonoids,
• B ring is linked in position 2 further subdivided on the basis of the
structural features of the C ring.
• These subgroup are: avones, avonols, avanones, avanonols, avanols or
catechins and anthocyanins.
• Finally, avonoids with open C ring are called chalcones.
CLASSIFICATION OF FLAVONOIDS
1. Flavones (2-phenylchromen-4-one)
• Have a double bond between positions 2 and 3 and a ketone in
position 4 of the C ring. ex:- Apigenin, Luteolin
2. Flavonols (3-hydroxy-2-phenylchromen-4-one)
• Have a hydroxyl group in position 3 of the C ring, which may also be
glycosylated. Ex: Kaempferol, Rutin, Myricetin, Quercetin.
3. Flavanones/ dihydroavones (2,3-dihydro-2-phenylchromen-4- one
• Have C ring saturated; the double bond between positions 2 and 3 is
saturated, ex: Hesperetin, Hespereidin, Naringenin
Subclassified: furanoavanones, prenylated avanones, pyranoavanones
or benzylated avanones
4. Flavanonols (dihydroavonols)/ 3-hydroxy-2,3-dihydro-2-phenyl
chromen-4-one
• Are 3-hydroxy derivatives of avanones; ex:Taxifolin, Silymarin
CLASSIFICATION OF FLAVONOIDS
5. Isoflavones / phytoestrogens.3-Phenylchromen-4-one skeleton
• subgroup of avonoids in which the B ring is attached to position 3 of the C ring.
have structural similarities to estrogens, such as estradiol
6. Neoflavonoids , Isoflavonoids and the Neoflavonoids can be regarded as abnormal
flavonoids.
• They have the B ring attached to position 4 of the C ring.
7. Flavanols or avan-3-ols or catechins
• Also referred to avan-3-ols as the hydroxyl group is bound to position 3 of C ring
• Another important feature of avanols, particularly of catechin and epicatechin, is the
ability to form polymers called as proanthocyanidins or condensed tannins. Ex:
Catechin (β-OH) 2- Epicatechin (α-OH)
8. Anthocyanidins (Flavylium (2-Phenylchromenylium) ion skeleton
• Sugar units are bound mostly to position 3 of the C ring and they are often
conjugated with phenolic acids, such as ferulic acid.
• Color of the anthocyanins depends on pH, methylation or acylation at the hydroxyl
groups on the A and B rings. Ex: Cyanidin. 2- Delphenidin.
9. Chalcones Chalcones and dihydrochalcones are avonoids with open structure
IDENTIFICATION OF FLAVONOIDS
1. Reaction with AlCl3 : Give yellow color with AlCl3 but
fluoresce differently in UV as shown in the following table .
Light Flavones Flavonols Flavanones
Visible Yellow Yellow Yellow
UV Green Yellowish- Yell. Green Pale brown
2. Lead subacetate test:- all flavonoids give yellowish
precipitate with Pb subacetate.
3. Shinoda test for flavanones and flavonols:
alcoholic solution + Mg metal ⁄ HCl → orange, red or violet
color
4. Antimony pentachloride test for chalcones:
alcoholic solution + SbCl5⁄ CCl4 → red or violet color
