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Dr.S.Alexandar,M.Pharm,Ph.D,
Associate Professor
Vinayaka Missions College of
Pharmacy,
Yercaud main road,
Kondappanaickanpatty,
Salem, Tamilnadu,
Pin:636008
FlavonoidsFlavonoids
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 three-
carbon 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 (3-
benzopyranes) 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
Kaemferol
Quercetin
Myricetin
Rhamnetin
Isorhamnetin
Name
Name
Chalcones
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. Cyanidin test
2. Test with boric and citric acids
3. An azo coupling
4. The reaction of alkali
5. Concentrated sulphuric acid test
6. The reaction with vanillin in concentrated
hedrochloric acid
7. The reaction of iron III chloride
8. The reaction of lead acetate
Compounds Cyanidin test КОН 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
to blue
Yellow
residue
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, Lion’s Ear, Lion’s Tail.
BASBAS:: 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
Dosage forms:: infusion
included Mixture
antiasthmatlca Trascovi,
tincture included
CardioPhyt, Biovital,
Gerovital, Doppelherz#
Energotonic
Pharmacological activity: infusion and tincture as
sedative and hypotensive agent in cardiovascular
neurosis, the initial stages of hypertension,
cardiosclerosis, increased nervous excitability.
Hawthorn Fruit – Crataegi Fructus
Hawthorn Flower – Crataegi Flores
Hawthorn –Crataegus sanguinea Pall.,
Family Rosaceae– Rosaceae.
Syn.: May, mayblossom, maythorn
BAS: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 “Саrdiovalenum”. 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
BASBAS:: 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, незначний
послаблюючий ефект.
• Dosage forms: liquid extract
Redshank Herb – Polygoni persicariae herba
Redshank – Polygonum persicaria L.,
Family Polygonaceae. – Polygonaceae.
Syn.: Persicaria, Redleg, Lady’s-thumb, Adam’s 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 it’s
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. It’s 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.

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flavonoids

  • 1. Dr.S.Alexandar,M.Pharm,Ph.D, Associate Professor Vinayaka Missions College of Pharmacy, Yercaud main road, Kondappanaickanpatty, Salem, Tamilnadu, Pin:636008 FlavonoidsFlavonoids
  • 2. Chemical analysis of flavonoids. Medicinal plants and medical plant material that contain flavonoids with cardiovascular, P-vitamin and haemostatic action
  • 3. FLAVONOIDS are polyphenolic compounds comprising fifteen carbons, with two aromatic rings connected by a three- carbon bridge (C6-C3-C6). Flavan
  • 4. The B ring formation is produced by a shikimate pathway
  • 5. The A ring and propane fragment are formed via acetate pathway
  • 6.
  • 7. 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 (3- benzopyranes) and the neoflavonoids (2-benzopyranes)
  • 8. 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
  • 9.
  • 12.
  • 13. 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.
  • 14. Identification 1. Cyanidin test 2. Test with boric and citric acids 3. An azo coupling 4. The reaction of alkali 5. Concentrated sulphuric acid test 6. The reaction with vanillin in concentrated hedrochloric acid 7. The reaction of iron III chloride 8. The reaction of lead acetate
  • 15. Compounds Cyanidin test КОН 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 to blue Yellow residue
  • 16. 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.
  • 17. Motherwort Herb – Leonuri herba, EP Motherwort – Leonurus cardiaca L., Leonurus quinquelobatus Mint family- Lamiaceae Syn.: Throw-wort, Lion’s Ear, Lion’s Tail. BASBAS:: 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 Dosage forms:: infusion included Mixture antiasthmatlca Trascovi, tincture included CardioPhyt, Biovital, Gerovital, Doppelherz# Energotonic Pharmacological activity: infusion and tincture as sedative and hypotensive agent in cardiovascular neurosis, the initial stages of hypertension, cardiosclerosis, increased nervous excitability.
  • 18. Hawthorn Fruit – Crataegi Fructus Hawthorn Flower – Crataegi Flores Hawthorn –Crataegus sanguinea Pall., Family Rosaceae– Rosaceae. Syn.: May, mayblossom, maythorn BAS: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 “Саrdiovalenum”. Liquid extracts from flowers included to CardioPhyt, Biovital, Gerovital and Phytulventum
  • 19. Water pepper Herb – Polygoni hydropiperis Herba , Water pepper – Polygonum hydropiper L., Family Polygonacea– Polygonaceae. Syn.: Smartweed, Biting persicaria, Bity tongue, Pepper plant BASBAS:: 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, незначний послаблюючий ефект. • Dosage forms: liquid extract
  • 20. Redshank Herb – Polygoni persicariae herba Redshank – Polygonum persicaria L., Family Polygonaceae. – Polygonaceae. Syn.: Persicaria, Redleg, Lady’s-thumb, Adam’s 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
  • 21. MRM which contain flavonoids with P-vitamin activity P-vitamin activity means that medicine or herb strength capillaries.
  • 22. Black chokeberry fruit – Aroniae melanocarpae Fructus recentes Black chokeberry – Aronia melanocarpa (Michx) Elliot Rosaceae • Constituents. Cyanidin and it’s 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.
  • 23. 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.
  • 24. 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. It’s 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.
  • 25. 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.