ROLE OF FOOD IN PREVENTION OF DIABETES & ASTHMA

CH.MYTHILI PRIYANKA
M.PHARMACY IST YEAR II SEM ( PHARMACOGNOSY ) G. PULLA REDDY COLLEGE OF PHARMACY

CONTENTS
1. 2. 3. 4. 5. 6. 7.

Introduction Nomenclature Flavnoids Biosynthesis Isoflavnoids Neoflavnoids Minor flavnoids

3 3 4 6 8 10 10

Flavanoids are the largest group of naturally occurring phenolic compounds, Flavanoids are also known as plant pigments The term flavonoid is generally used to describe a broad collection of natural products that include a C6-C3-C6 carbon framework, or more specifically a phenylbenzopyran functionality.

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B
O

NOMENCLATURE Depending on the position of the linkage of the aromatic ring to the benzopyran (chromane) moiety, this group of natural products may be divided into three classes:

flavonoids (2-phenylbenzopyrans) isoflavonoids (3-benzopyrans) neoflavonoids (4-benzopyrans)

the flavonoids

the isoflavonoids (3-benzopyrans)

the neoflavonoids (4-benzopyrans)

(2-phenylbenzopyrans)

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5' 6'

O
4' 3'
3

B
8 7 6 5 4

O 2

2'

Flavanoids Flavanoids are the largest group of naturally occurring phenolic compounds, which occur in different plant parts both in free state and as glycosides.

Flavanoids are also known as plant pigments or co-pigments. responsible for the various colors and combination of colors exhibited by bark, leaves, flowers, fruits and seeds of plants. - exhibit various biological activities in mammals, the most important one being the antioxidant activity.

Occurrence : Flavonoids are widely distributed in nature and are especially common in higher plants belonging families Leguminoseae, Rutacee, Primulaceae, Polygonaceae, Pinaceae, Rosaceae, Asteraceae, Lamiaceae Moraceae, Betulaceae, Rubiaceae etc

Flavonoids are found to occur in different parts of the plants ( roots, bark, heartwood, leaves, flowers, fruits and seeds).

FUNCTIONS OF FLAVONOIDS IN PLANTS

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Flavonoids are the most important plant pigments for flower coloration producing yellow or red/blue pigmentation in petals designed to attract pollinator animals. In addition, some flavonoids have inhibitory activity against organisms that cause plant disease eg. Fusarium oxysporum.

BIOLOGICAL ACTIVITIES They are venoactive- decreses capillary permeability, fragility vit C deficiency vit p Antioxidant activity -Anti inflammatory activity, cancer & anoxia protein kinase inhibition,- the amino acids phosphorylation is inhibited by acting on tyrosine Enzyme inhibition-histidine decarboxylase quercetin, hyaluronidase - proanthicynidins prostaglandin-synthesis inhibition, antiulcer, antiarthritic, antimicrobial topoisomerase inhibition. PROPERTIES Water soluble compounds Present as glycosides Present as mixtures Gives colour change with base Shows absorption bands in UV and visible regions of spectrum Can be separated by chromatography

THERAPEUTIC USES Treatment of symptoms of venous & lymphatic vessel insufficiency :tiredness, fullness of legs Dysfunctions linked to acute attack of piles Treat capillary & venous disorder THE BIOSYNTHESIS OF FLAVONOIDS PHENYLPROPANOID METABOLIC PATHWAY-

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phenylalanine 4-coumaroyl-CoA +malonyl-CoA chalcones, which contain two phenyl rings. Conjugate ring-closure of chalcones results in the formation a flavone. The metabolic pathway continues through a series of enzymatic modifications to yield flavanones dihydroflavonols anthocyanins. Along this pathway, many products can be formed, including the flavonols, flavan-3-ols, proanthocyanidins

Based on the degree of oxidation and saturation present in the heterocyclic C-ring, the flavonoids may be divided into the following groups:
5' 6'

B
8 7 6 5

4' 3'

C
4

2'

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GROUP

DISCREPTION

3hydr oxyl

Flavone

2phenylchromen4-one 3-hydroxy-2phenylchromen4-one 2,3-dihydro-2phenylchromen4-one 3-hydroxy-2,3dihydro-2phenylchromen4-one

2,3dih ydr o

Structural formula

Examples

Luteolin, Apigenin,

Flavonol

Quercetin, Kaempferol , Myricetin, Hesperetin,

Flavanone

Flavanonol

Taxifolin

ISOFLAVONOIDS

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O
3

Isoflavonoids are colourless. They occur in free form rather as a glycoside In contrast to most other flavonoids, isoflavonoids have a rather limited taxonomic distribution, mainly within Leguminosae & Fabaceae Sources- SoybeanMilk Fermented products DerrisRotenoids Daidzein

ESTABLISHMENT OF STRUCTURE It has been established that acetate gives rise to ring A and that phenylalanine, cinnamate and cinnamate derivatives are incorporated into ring B and C-2, -3, and -4 of the heterocyclic ring.

Since chalcones and flavanones are precursors of isoflavonoids, the required aryl migration of ring B from the former 2 to the 3 of the precursor must take place after formation of the basic C15 skeleton.
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Isoflavonoids possess a 3-phenylchroman skeleton

8

2 2'

6 4

isoflavan
O

isoflavone
O

isoflavanone

OH

isoflav-3-ene

isoflavanol

BIOLOGICAL ACTIVITIES They act as phytoalexins Bind to estrogen receptor Anti carcinogenic Have preventive effect on prostate, breast colorectal cancer NEOFLAVONOIDS (4-BENZOPYRANS) Neoflavnoids are isolates from DALBERGIA ( Fabaceae) CALOPHYLLUM(Clusiaceae)
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CALOPHYLLUM shows a anti viral property because of presence of 4- aryl coumarin

O O O O O

4-arylcoumarin

3,4-dihydro-4-arylcoumarin

neoflavene

MINOR FLAVONOIDS

Natural products such as chalcones and aurones also contain a C6-C3-C6 backbone and are considered to be minor flavonoids. AURONES CHALCONE

In a few cases, the six-membered Chalcones donot have central hetrocyclic heterocyclic ring C is replaced by a five - nucleus membered ring. & characterized by a 3 c chain Eg- Hispidol 3- OH- Butein

ANTHOCYANINS(FLAVNOID)

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R-OH

Next to chlorophyll, anthocyanins are the plant pigments visible to the human eye. They are of great economic importance as fruit pigments and thus are used to colour fruit juices, wine and some beverages. EXAMPLES
OH O
+ +

RO OH HO O

PELARGONIDIN

OH OH

Orange-red flowersdahlia,pelargoni um Crimson-bluish, red flowersroses, blue corn Red peony Violet-blue flowersdelphinium Light blue flowers primula viscosa

OH OH

CYANIDIN

pelargonidin
RO OH HO O
+

cyanidin R=H peonidin R=Me

PEONIDIN
HO OH HO O
+

R'O OH

DELPHINIDIN

OH

MALVIDIN
O---Glc

delphinidin R=R'=H petunidin R=Me,R'=H malvidin R=R'=Me

OH

PROPERTIES water soluble Amphoteric In different media they show different colours

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ACIDIC-

Red

NEUTRAL- Purple BASICBlue

USES Causes increase in osmotic pressure of cell sap Attracting insects & thus helps increases pollination In respiration & photosynthesis they play a vital role they act as light filters thus preventing the decomposition of chlorophyll

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