Chemical analysis of flavonoids. Medicinal plants

and medical plant material that contain flavonoids with

cardiovascular, P-vitamin and haemostatic action

FLAVONOIDSare 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

PelargonidinCyanidinDelfinidin

Flavanones

Name

LiquiritigeninNanringeninEriodictyolHesperetin

Flavones

Name

ApigeninLuteolinAquacetinDiosmetin

Flavonols

KaemferolQuercetinMyricetinRhamnetinIsorhamnetin

Name

Name

Chalcones

ButeinIsoliquiritigenin

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, maythornBAS: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 recentesBlack 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 foliaTea – 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.