FLAVONOIDS

SUBMITTED BY – SUBMITTED TO –

ABUZAR HURAIRA PROF. VIDHU AERI

M.PHARMA 1ST SEM. DEPARTMENT OF
PHARMACOGNOSY AND PHYTOCHEMISTRY
DEPARTMENT OF
SPER
PHARMACOGNOSY AND PHYTOCHEMISTRY
JAMIA HAMDARD
SPER
JAMIA HAMDARD
INTRODUCTION
Flavonoids are polyphenolic compounds that are found in a variety of dietary
sources such as fruits and berries, nuts, seeds, and herbs.

Flavonoids are a wide category of polyphenolic compounds that have a major

role in the treatment of various inflammatory diseases, including arthritis,
gastritis, nephritis, hepatitis, ulcerative colitis, Alzheimer's disease,
atherosclerosis, and many allergic reactions.

They are generally yellow-coloured pigments. They are a larger group of the
glycoside. They are 2-phenylbenzopyrones derivatives and produce a large
number of physiological activities.

STRUCTURE OF FLAVONOID -
 Physical Properties:

•They are crystalline substances with a certain melting point.

•Catechins , Flavones, Isoflavanes , Flavanones , Flavanonoles

are colourless crystals whereas Flavones, Flavonols , Chalcones
are yellow coloured crystals. Anthocyanidins are red in acidic
media and blue in alkaline media.

•Flavonoid glycosides are generally soluble in water and alcohol

but insoluble in organic solvents.

•Aglycone parts of flavonoids are soluble in diethyl ether, acetone,

alcohol etc.

•Flavanols are optically active.

Chemical Properties:

•Chemically flavonoids are based upon a fifteen-carbon

skeleton (C15) consisting of two benzene rings (A and B)
linked via a heterocyclic pyrene ring (C).

•They occur as aglycones, glycosides, and methylated

derivatives.

•The Six-member ring condensed with the benzene ring is

either an α-pyrone (flavonols and flavanones) or its dihydro
derivative (flavonols and flavanones).

•The position of the benzenoid substituent divides the

flavonoid class into flavonoids (2-position) and isoflavonoids
(3-position).
 RESVERATROL
Occurrence:
•Resveratrol (3,5,4'-trihydroxy-trans-stilbene) is a
stilbenoid, a type of natural phenol, and a phytoalexin
produced by several plants in response to injury or when
the plant is under attack by pathogens, such as bacteria or
fungi.
•Sources of resveratrol in food include the skin of grapes,
blueberries, raspberries, mulberries, and peanuts.

Extraction and Isolation:

Isolation of resveratrol is based on the chemical properties
of compounds in the 95% ethanol extract. The whole
process included reflux extraction, filtering, hydrolyzing,
liquid-liquid extraction and eluting.
Flow Chart Representative Of The Extraction and
Purification process of Resveratrol-

Powder Drug
 Different technologies for the extraction and
purification of resveratrol :

There are several different methods for the preparation of

resveratrol –

• The conventional methods such as macroporous resin or silica gel

column chromatography are simple, but they are time-consuming
and require a large amount of organic solvents.

• High-speed counter-current chromatography and supercritical fluid

extraction are of advanced technologies, but they need expensive
equipment.

• Acid hydrolysis combined with alkaline solution washing approach.

Because of no participation of precious instrument and less
consumption of organic solvents in this method, its cost is naturally
lower.
Filtering and Hydrolyzing :

•The 95% ethanol extract mentioned above was pulverized into

powder form (less than 0.9 mm).

• A milled sample and water in a proportion of 1:30 (w/v, g/mL) were

sealed in a vessel and placed into the ultrasonic cleaning bath for 20
min at 50 OC.

•The mixture finally becomes a uniform suspension solution, and

was immediately filtered at lower pressure. The aqueous solution
and the residue acquired were used for HPLC detection.

•In order to hydrolyze polydatin to resveratrol, the aqueous solution

was adjusted with hydrochloric acid to pH = 1 and hydrolyzed by
refluxing water bath for 8 h at 75 OC.
Liquid-liquid extraction :

• Liquid-liquid extraction was carried out in a separating funnel.

• The aqueous solution mentioned above was mixed with the same
volume of extraction solvent, and the separation between the
aqueous and organic phases was carried out by gravitational
sedimentation.

• To achieve a high recovery extraction was repeated three times.

The volumes of aqueous and organic phases were measured and
concentrations of resveratrol in each phase were analyzed with
HPLC.
Characteristic features :

• Resveratrol (3,5,4’-trihydroxy-trans-stilbene) belongs to

polyphenols’ stilbenoids group, possessing two phenol rings
linked to each other by an ethylene bridge.

•It is a phytoalexin that acts against pathogens, including

bacteria and fungi.

•As a natural food ingredient, numerous studies have

demonstrated that resveratrol possesses a very high antioxidant
potential.

•Resveratrol also exhibit anti-tumor activity, and is considered

a potential candidate for prevention and treatment of several
types of cancer.
CONT..
•Even more, other bioactive effects, namely as anti-inflammatory,
anti-carcinogenic, cardioprotective, phytoestrogenic and
neuroprotective have also been reported.

•Nonetheless, resveratrol application is still being a major challenge

for pharmaceutical industry, due to its poor solubility and
bioavailability, as well as adverse effects.

Structure :
 RUTIN

Rutin is a citrus flavonoid glycoside, which is a low molecular

weight polyphenolic compound. There are various physiological
functions of rutin and related flavonoids in the human body and
other species, including plants. Rutin is one of the best natural
antioxidants in the known natural class.

Occurrence :
•It is found in various fruits and fruit rinds, especially citrus fruits
and berries such as Ruta graveolens and Morus alba.
•Rutin is also called vitamin P, which is widely distributed in
vegetables, fruits, and medicinal herbs such as asparagus and
buckwheat.
•Further, buckwheat (Fagopyrum esculentum) is considered to be
one of the best dietary sources of rutin.
Isolation -
 Characteristic features:

•Rutin (quercetin rutinoside), like quercitrin , is a glycoside of the

flavonoid quercetin.
•As such, the chemical structures of both are very similar, with the
difference existing in the hydroxyl functional group.
 QUERCETIN

•Quercetin is a plant flavonol from the flavonoid group of

polyphenols.
•It is found in many fruits, vegetables, leaves, seeds, and grains; red
onions and kale are common foods containing appreciable content
of quercetin.
•Quercetin has a bitter flavor and is used as an ingredient in dietary
supplements, beverages, and foods.
 HESPERIDIN

•Hesperidin is a flavan-on glycoside found in citrus fruits. Its

aglycone form is called hesperetin.

•Its name is derived from the word "hesperidium", for fruit produced
by citrus trees.

•Hesperidin was first isolated in 1828 by French chemist Lebreton

from the white inner layer of citrus peels (mesocarp, albedo).
Occurrence :
•Hesperidin, a polyphenolic bioflavonoid, is the predominant flavonoid
in orange peel and other citrus fruits.

•The highest concentration of hesperidin can be found in the white

parts and pulps of the citrus peels.

•Hesperidin can also be found in green vegetables. Hesperidin is a

flavanone glycoside consisting of the flavone hesperitin bound to the
disaccharide rutinose.

•The sugar causes hesperidin to be more soluble than hesperitin

Figure shows its structure. Hesperidin is an antioxidant that enhances
the action of vitamin C to lower cholesterol levels.

•It is also known to have pharmacological action as an anti-

inflammatoryand antiviral agent.
 Isolation:

Hesperidin can be isolated by two different methods:

•The first method involves extracting the dried citrus peel successively
with petroleum ether followed by methanol. The petroleum ether
removes the essential oils in the peel and the methanol will extract the
glycoside (hesperidin).

•The second method uses an alkaline extraction of chopped orange

peel and acidification of the extract. The hesperidin can then be
crystallized from the acidified extract. Because of its highly insoluble,
crystalline nature, hesperidin is one of the easiest flavonoids to isolate.
Characteristic features:

•Ferric chloride test: Addition of ferric chloride Solution to hesperidin produces a

wine red color.
• Magnesium-hydrochloric acid reduction test: Drop wise addition of concentrated
hydrochloric acid to an ethanolic solution of hesperidin containing magnesium
develops a bright violet color.
Acidic degradation of hesperidin.

Uses:
•It is thought to have beneficial effects on the blood vessels.
•It used as a natural remedy for a number of health problems , including : allergies,
hemorrhoids, chronic venous insufficiency, high blodd pressure, high cholesterol,
cancer, anti-oxidant.
•It may trigger a no. of side effects, including abdominal pain, diarrhoea and nausea.
 NARINGIN
Naringin belongs to the flavonoid family.

• Flavonoids consist of 15 carbon atoms in 3 rings, 2 of which must be

benzene rings connected by 3 carbon chain.

•Naringin contains the basic flavonoid structure along with two

rhamnose units attached with its aglycone portion, called naringenin,
at the 7- carbon position.

•The steric hindrance provided by the two rhamnose units makes

naringin less potent than its aglycone counterpart, naringenin.
Occurrence:

•Naringin is a flavanone-7-0-glycoside between the flavanone

naringenin and the disaccharide neohesperidose.

•The flavonoid naringin occurs naturally in citrus fruits, especially

in grapefruit, where naringin is responsible for the fruit's bitter taste.

•In commercial grapefruit juice production, the enzyme naringinase

can be used to remove the bitterness created by naringin.

•In humans naringin is metabolized to the aglycone naringenin (not

bitter) by naringinase present in the gut.
Characteristic features:
•Naringin is an important water soluble flavonoid isolated from the
citrus fruits.
•It has a molecular weight of 580.4 g/mol and molecular formula is
C27H23014.
•It has antioxidant potential and plays an important role in the
development of leaves, flowers, buds and fruits of plants.
•It has further induces bitterness to the fruits as in grape fruit.
•However, the bitterness can be reduced upon reduction by the
enzyme naringinase.
THANK YOU