Flavonoids

Dr.S.Alexandar,M.Pharm,Ph.D,
Associate Professor
Vinayaka Missions College of
Pharmacy,
Yercaud main road,
Kondappanaickanpatty,
Salem, Tamilnadu,
Pin:636008

Chemical analysis of
flavonoids. Medicinal plants
and medical plant material that
contain flavonoids with
cardiovascular, P-vitamin and
haemostatic action

FLAVONOIDS
are polyphenolic compounds comprising fifteen
carbons, with two aromatic rings connected by a threecarbon bridge (C6-C3-C6).

Flavan

The B ring formation is produced by a shikimate pathway

The A ring and propane

fragment are formed via
acetate pathway

Classification of flavonoids
Depending on the position of the linkage of the aromatic ring to the
benzopyrano (chromano) moiety, this group of natural products
may be divided into three classes:
the true flavonoids (2-phenylbenzopyrans); the isoflavonoids (3benzopyranes) and the neoflavonoids (2-benzopyranes)

True Flavonoids
1.Chromane derivatives 2. Chromone derivatives
- catechins (flavan-3-ols);
- flavanons;
- leucoanthocyanidins
- flavanonols;
(flavan-3,4,-diols);
- flavones;
- anthocyanidins
- flavonols;
- chalcones;
- dihydrochalcones;
- aurones

Anthocyanidins
Name

Pelargonidin
Cyanidin
Delfinidin

Flavanones
Name

Liquiritigenin
Nanringenin
Eriodictyol
Hesperetin

Flavones
Name

Apigenin
Luteolin
Aquacetin
Diosmetin

Flavonols

Name
Kaemferol
Quercetin
Myricetin
Rhamnetin
Isorhamnetin
Chalcones
Name
Butein
Isoliquiritigenin

Extraction and investigation methods of flavonoids

Ethanol and methanol are mainly used for flavonoid
extraction. Spirituous extracts are evaporated to water residue,
then diluted with water and treated by chloroform for lipids
and lipoids (chlorophylls, carotenoids, waxes, etc.) separation.
Purified water residue is treated by diethyl ether, ethyl acetate,
propanol, butanol in series, getting fractions of aglycones,
mono-, di-, triglycosides.

Identification
1.
2.
3.
4.
5.
6.

Cyanidin test
Test with boric and citric acids
An azo coupling
The reaction of alkali
Concentrated sulphuric acid test
The reaction with vanillin in concentrated
hedrochloric acid
7. The reaction of iron III chloride
8. The reaction of lead acetate

Compounds

Cyanidin test

FeCl3

lead acetate

Flavanols

Red-violet

Yellow

Brown

Yellow residue

Flavonols

Red

Yellow

Green

Yellow residue

Flavones

Orange

Yellow

Red-brown

Yellow residue

Chalcones

Yellow

Yellow-orange

Brown

Yellow residue

Aurones

Yellow

Orange-red

Brown

Yellow residue

Catechins

Yellow

Colorless,
changing to
red

From brown Yellow residue

to blue

Quantitative analysis
There are plenty of methods for flavonoid assay: gravimetry,
titration, fluorimetry, polarography, photocolorimetry, but the
most widespread method is spectrometry. It is based on
reactions with metal ions, azo coupling, boric acid with further
determination of the optical density in UV and visible regions
of the spectrum at a proper wavelength.

Motherwort Herb Leonuri herba, EP

Motherwort Leonurus cardiaca L., Leonurus quinquelobatus
Mint family- Lamiaceae
Syn.: Throw-wort, Lions Ear, Lions Tail.
BAS: complex flavonoids, alkaloides (major is

stachydrine),irydoides, tannins, terpenoids. Major

flavonoids hyperoside, kaemferol-3-D-glucoside rutin,
quercetin, isoquercetin, tannins and a small amount of
essential oil. The EP requires a minimum flavonoid
content for the drug of 0,2 % expressed as hyperoside
and assayed by adsorbance at 425 nm

Pharmacological activity: infusion and tincture as

sedative and hypotensive agent in cardiovascular
neurosis, the initial stages of hypertension,
cardiosclerosis, increased nervous excitability.
Dosage forms: infusion
included Mixture
antiasthmatlca Trascovi,
tincture included
CardioPhyt, Biovital,
Gerovital, Doppelherz#
Energotonic

Hawthorn Fruit Crataegi Fructus

Hawthorn Flower Crataegi Flores
Hawthorn Crataegus sanguinea Pall.,
Family Rosaceae Rosaceae.
Syn.: May, mayblossom, maythorn
BAS: giperoside (0,7%), C-glycosides vitexin:, rutin,
dominate in the leaves.
The fruits contain epicatechin, oligomers
anthocyanidins, and also anthocyans, pectins,
ascorbic acid
Pharmacological activity : Galene drugs have
cardiotonic, hypotensive, sedative and
antispasmodic action, reduce the excitability of
the central nervous system, have tonics effect on
the heart muscle, enhanced blood circulation in
coronary heart and cerebrovascular, eliminate
tachycardia and arrhythmia
.

Dosage forms : Liquid extract of the fruit

included to rdiovalenum. Liquid
extracts from flowers included to
CardioPhyt, Biovital, Gerovital and
Phytulventum

Water pepper Herb Polygoni hydropiperis Herba ,

Water pepper Polygonum hydropiper L.,
Family Polygonacea Polygonaceae.
Syn.: Smartweed, Biting persicaria, Bity tongue, Pepper plant
BAS: rutin, quercetin, hiperosed,
cemppherol, tannins, vitamins
K and C.
Raw materials containing
substances such as colored
phagopirin causing
phagopiryzm (sensitivity to
light).
Pharmacological activity :
hemostatic,
.

Dosage forms: liquid extract

Redshank Herb Polygoni persicariae herba

Redshank Polygonum persicaria L.,
Family Polygonaceae. Polygonaceae.
Syn.: Persicaria, Redleg, Ladys-thumb, Adams plaster
BAS: hiperosed, isoquercetin,,
tetrametilquercetin. Herb
containing vitamin K, tannin,
flobafen free galou acid,,
essential oil, pectins.
Pharmacological activity :
hemostatic, a slight laxativ
effect.

Dosage forms: tea, extract

MRM which contain flavonoids with

P-vitamin activity
P-vitamin activity means that
medicine or herb strength capillaries.

Black chokeberry fruit Aroniae melanocarpae Fructus recentes

Black chokeberry Aronia melanocarpa (Michx) Elliot
Rosaceae
Constituents. Cyanidin and its
glycosides, phenolic acids,
flavonoids- rutin, quercetin,
gesperidin; pectines; ascorbic acid;
big amount of iodine (5-6
mcg/100g), Folic acid, riboflavin,
tocopherol, carotinoids; lipids, wax,
paraffin.

Uses. Fresh fruits and juice are

used for prevention of vitamin P
insufficiency, they are useful for
those with hypertension. Lipophilic
substances are the part of Aromelin
which has restorative action.

Pagoda tree buds Sophorae japonicae Alabastrae

Pagoda tree fruit Sophorae japonicae Fructus
Pagoda tree Sophora japonica
Syn.: Chinese Scholar, Japanese pagoda tree.
Fabaceae

Constituents. Up to 20% of
rutin.
Uses. As the main constituent
is rutin the plant is used in the
treatment of circulatory
diseases (Ascorutin, Vikalin,
Rutes). Tincture has antiseptic
properties.

Lemon peel Citri Exocarpium

Lemon - Citrus limon
Rutaceae
Constituents: flavonoids, especially
neohesperidosides and rutinosides of
hesperetin and naringenin (rutin, eriocitrin,
neohesperidin, hesperidin) along with many
other flavonoids (44 flavone glycoside were
detected); essential oil (+ limonene as the
principle component, citral determine the
odour); carotenoids, citric acid and many
other plant acids, coumarin derivatives,
pectins.
Uses. Its used chiefly as an aromatic and stomachic. The efficacy of
lemon flavonoids in treating varicose veins is related to their ability to reduce
capillary fragility, increase integrity of the venous wall and increase the
muscular tone of the vein.
The raw material and its extracts are used to treat diseases of the blood vessels
and lymph system, including haemorrhoids, chronic venous insufficiency, leg
ulcers, nosebleeds.

Tea leaf Theae folia

Tea Thea sinensis (syn. Camellia sinensis) (L.)
Theaceae
Constituents: abundant flavonoids, including the
apigenin derivatives isoschaftoside and vicetin-3,
catechols, leucoanthicyanidins, theaflavins,
condensed tannins (10-20 %), 4-gallocatechol,
phenolic carboxilic acids (gallic, chlorogenic);
methylxanthines (caffeine, theobromine,
theophylline, adenine, xanthine); the flavour and
aroma substances, some of which arise during the
fermentation stage (hex-3-en-1-ol, benzyl
alcohol, linalool in black tea and geraniol in grean
tea); triterpenoid saponins.

Uses. Owing to its caffeine content, tea serves as a stimulant, and bacause of its
tannin content it can be used an anthidiarrhoeic. Polyphenols have P-vitamin
and the antioxidant activity. Strong tea is given in poisonings caused by central
nervous system inhibitors, alcohol, heavy metals.