Drugs Containing Flavonoids

Drugs Containing Flavonoids

FOLIA BETULAE (Birch)

The drug consist of the dried leaves of Betula pendula or B. pubescens (Ph EUR)

Birch leaf contains many flavonoids (2-3%); rutin, quercitrin, hyperine, and other glycosides of quercetin, metylated flavones, and more, as well as phenolic acids and triterpenes.

O O OH OH OH OH OH OR h 7 5 3' 4' 5' 3 MIRSITROZIT O OH OH OH OGal 7 3' 4' 3

FOLIA BETULAE (Ph. E.)

In France the drug is traditionally used orally to enhance urinary and digestive elimination functions.

Is is used for the adjunctive treatment of rheumatism pain.

Betulinic acid is cytotoxic in vitro and in vivo: it inhibits the growth of human melanoma in mice, selectively, by inducing apoptosis.

FLOS CRATAEGI, Hawthorn

Hawthorn berry and Hawthorn flowers and flowering tops are obtained from Crataegus sp. (C.oxyacantha &

C.monogyna)(Rosaceae)

Hawthorn is a thorny shrub common in almost all of the temperate areas of the northern hemisphere. In Turkey, 20 of Crataegus species grown, the most common species is C.monogyna.

FLOS CRATAEGI

The chief flavonoid constituent of the leaves is hyperin, the 3- galactoside of quercetin.

Flavone C-glycosides are also found: Viteksin, orientin, and most of all, their 2’’-O-ramnosylated derivatives.

O O OH OH OH Gl 7 5 4' 8

O

OH OH

3 4

FLOS CRATAEGI

Pharmacological properties;

Flowering tops and flowers are traditionally used to treat abnormalities of the cardiac rhytm in the adult ,

and in the symptomatic treatment of neurotonic disorders in the adult and in the child (eg. Minor sleeplessness)

Antispasmodic action

Hypotensive activity

Decrease peripheral vascular resistance This drug has no acute toxicity.

FLOS CRATAEGI

In France, hawthorn flowering tops and flowers may be used in the

formulation of plant-based phytomedicines containind flavonoids (%2.2) and proanthocyanins (%18.75) in doses 160-900 mg/daily.

CORTEX VIBURNI (TK)

Viburnum prunifolium (Caprifoliaceae)

Common in northern America

The bark of the plant is dark reddish.

In Turkey, there are 4 Viburnum species; V.opulus,

CORTEX VIBURNI (TK)

Biflavonoids ---Amentoflavon

Phenolic glycosides (Salycosides) (Salisil alkol heteroziti) taşır

Uterine spasmolitic (activity of 1g drug equal to 500 µg papaverin activity)

The plant has antiinflammatory effect (responsible constituen is amentoflavon)

O O OH OH OH OH OH OH O O 5' 8 AME NTOFLAVON (BIFLAVONOIT) CH₂OH OGl S ALIKOZIT (FE NOL HE T.)

FLOS SAMBUCI (TK), Mürver çiçeği

_{Sambucus nigra (Caprifoliaceae) çiçek açma zamanı} toplanan çiçek durumlarıdır.

Avrupa, K.Afrika, Batı Asya’da yetişir.

_{K.Anadolu başta olmak üzere Türkiye’de yaygındır.} _{10m, beyaz çiçekli ağaççıktır.}

Müsilaj UY (%0.3)

FLOS SAMBUCI

Elder flower is traditionally used orally to enhance the urinary and digestive elimination functions.



Increase in bronchial secretions (due to mucilage)

High doses of the drog can cause minor gastrointestinal distress.

HERBA VIOLAE TRICOLORIS (VIOLET)

Viola tricolor is common in Turkey and Europe (Violaceae)

The drug is the dried aerial parts of the plant.

Flavonols ---Violanthine (quercetin-3-O-rutinoside).

HERBA VIOLAE TRICOLORIS (TK), Hercai

menekşe

Diuretic

OH OH OH O OH OH OH DE LFINIDOL (5,7,3',4',5'-PE NTAHIDROKSI ANTOSIYANIDOL) OH COOH P-KUMARIK AS IT TÜRE Vİ O O OH OH OH O rutinoz OH 3' 4' 5 7 KE RSE TOL-3-0-RUTINOZ

Lespedeza capitata (Leguminosae)

The leaves of the plant are used as drog.

This plant is not grown in Turkey.

North American plant

It cn be cultivated in Mediterranean region.

O O OH OH OH OH holozit 3' 4' 5 7 6

Lespedeza capitata (Leguminosae)

Antiiuremic

Against venous inflammation

Hesperetin (Citrin, Citroflavonoids)

Citrus (Rutaceae) are trees of oriental origin, of which many species, varieties and hybrids are cultivated for their fruits and their edible endocarp. These are very abundant in the pericarp, and are mainly flavonone glycosides (hesperidin or hesperetin 7-O-rutinoside, naringin, eriodyctin.

Citroflavonoids are to improve the symptoms of venous and lymphatic vessel insufficiency, for the

O O OCH₃ OH O OH 3' 4' 5 7 R h Gl

HE SPE RIDOZIT(HE SPE RE TOL 7-O-RAMNOZIDO GLUKOZIT) 7 5 4' 3' O OCH₃ OH OH

Isolation of Hesperetine

Method A: Orange peels + Petroleum ether (essential oils) Pericaps + MeOH extraction –evaporation ---with CH₃COOH HESPERETINE is precipitate

Method B: Orange peels + alkali extraction

---+CH₃COOH ----Precipitate (Glicoside) ----+ dissolve in formamide --- purification with active carbon

----HESPERETINE is precipitate

Luteoline

5,7,3’,4’- tetrahydroxy flavone

-Olive leaves

- Digitalis leaves

Labiatae family (F.Mentahae, F. Rosmarini, F. Thymi, F. Salviae)

Compositae family (Fl. Chamomillae romanae, Fl. Chamomillae matricariae, Cynara scolymus)

7 5 4' 3' O O OH OH OH OH LUTE OLOL (5,7,3',4' TE TRAHIDROKSI FLAVON)

RADIX DERRIDIS

Derris elliptica (Leguminosae)

Southern Asia

Roots contain Rotenone (%8)

Insectisidal activity

Rotenone cause respiratory depression Antihelmintic

O O O OCH₃ OCH₃ O A _B C ROTE NON

(A,B,C HALKALARI IZOFLAVON ÇE KİRDE Ğ İ) furan

piron

piran

FOLIA MYRTILLI, FRUCTUS MYRTILLI,

Bilberry

Vaccinium myrtillus (Ericaceae)

Bilberry (or blueberry) well-known for its tasty fruits, it is used by the pharmaceutical industry for the extraction of anthocyanins.

The leaf and the dried fruit are used in phytotherapy. Blueberries are abundant in the woods that grow on siliceous soils in the mountains of the northern

FOLIA MYRTILLI, FRUCTUS MYRTILLI

The bilberry leaf contains;

Phenolic acids (quinic, malic, benzoic, succinic acids 2-5 %) Flavonoids (quercetin glycosides) and traces of quinolizidine alkaloids.

It is rich in proanthocyaniins and catechine (up to 10%), neomyrtilline Astringent and antidiarreic

FOLIA MYRTILLI, FRUCTUS MYRTILLI,

Çoban üzümü

Fruits;

Rich in anthocyanins (up to 5%) MIRTILLIN---Delphinidin glycoside

OH OH OH O OGl OH OH MIRTILLIN

(DE LFINIDOL GLUKOZITI)

FOLIA MYRTILLI, FRUCTUS MYRTILLI

Extracts obtained from the bilberry fruits

and enriched in anthocyanins are

ingredients of drugs used to treat the

functional symptoms of venous and

lymphatic vessel insufficiency, cutaneous

capillary fragility, and mesopic scotopic

vision (nyctalopia, myopia).

FOLIA MYRTILLI, FRUCTUS MYRTILLI

German Commision E considers the bilberry fruit to be an astringent, used as such for the symptomatic treatment of diarrhea and as a topical

anti-inflammatory in case of irritation of the mucous membranes of the mounth and throat.

FOLIA MYRTILLI, FRUCTUS MYRTILLI

The first step in the manufacturing process is the biological

elimination of the sugars by Saccharomyces oviformis; the medium

recovered from fermentors is clarified by on-line centrifugation and concentrated under vacuum at low temperature.

The purification of this crude extract entails repeated treatment with boiling ethanol.

Upon cooling of the ethanol solution, the insoluble anthocyanins precipitate and are recovered by centrifugation ( the free

FOLIA MYRTILLI, FRUCTUS MYRTILLI

CYNARA SCOLYMUS (ARTICHOKE)

The artichoke is a large herbaceous perennial plant, with a rosette of pinnatisect leaves, with prominent veins, but not spiny.

The flowers (which appear in the 2 nd year) are grouped in big capitulums of 10-15 cm in diameter, borne by

hardy ramified grooved stems, with sessile and almost entire leaves.

The receptacle and the base of the bracts constitute the edible part of this vegetable.

CYNARA SCOLYMUS (ARTICHOKE)

Cynara scolymus is an improved cardoon unknown in the

wild and only cultivated. (C. scolymus var.sativa)

To fulfill pharmaceutical needs, the first year rosette of leaves is preferred and is harvested from plants produced especially for this purpose.

When dried under good conditions (ventilation, low

temperature 400_{C) the drug retains its original colours:} greenish-grey top side and whitish underside.

CYNARA SCOLYMUS (ARTICHOKE)

The active constituents of Artichoke are phenolic acids and phenolic alcohols.

The former are esters of caffeic acid (1%):

5-caffeoilquinic acid (or chlorogenic acid) and 1,5-dicaffeoilquinic acid (Cynarine) in the fresh drug.

Flavonoids; Luteolin dervatives;

1- Cynaroside----luteolin-7-monoglucosyl

O OH GlO OH OH O SINAROZIT 7 7 O OH O OH OH O R h Gl SKOLIMOZIT 7 O OH O OH OGl O R h Gl 4' SINARATRIOZIT

COOH OH OH KAFE IK AS IT OH OH OH OH COOH KINIK AS IT O COOH OH OH O C O CH CH OH OH C O CH CH OH OH + 1 5

OH OH CH CH C O O OH OH OH COOH 1 5 3 KLOROJ E NIK AS IT OH O OH OH ₁ COOH 5 C O CH CH OH OH NE OKLOROJ E NIK AS IT

CYNARA SCOLYMUS (ARTICHOKE)

This drug traditionally used to enhance urinary and digestive elimination

functions, as a choloretic or cholagogue, and to enhance the renal elimination of water.

Cynarine displays a clear activity on the biliary flow rate.

Patients allergic to Asteraceae are at risk for an allergic reaction to products containing artichoke.

CYNARA SCOLYMUS (ARTICHOKE)

There are a lot of pharmaceuticals in European countries. Diuretic

Choleretic and chollagogue Lower blood cholesterols Hepatoprotective

CYNARA SCOLYMUS (ARTICHOKE)

FLORES CARTHAMI (SAFFLOWER)

Carthamus tinctorius (Compositae)

Annual, yellow flowers Leaves are sessile

Arabia

Cultivated in Europe, America and Asia Naturally grown in Turkey

FLORES CARTHAMI (SAFFLOWER)

Chalcones ---Carthamine (yellow colour) enzymatic oxidation ---Cathamone (red colour)

Extracts of the plant are red due to oxidation Flavanons --- Cartamidine (colourless), luteolin

OH OH OH OGl O OH KARTAMIN (S ARI) OH OH OH O O OH

KARTAMIDIN (RE NKS IZ) O O OGl O OH OH KARTAMON (KIRMIZI-TURUNCU) E NZ.OKS IDAS YON

FLORES CARTHAMI (SAFFL53OWER)

Flowers used as drug Used in cosmetics

Used as dying material in food industry. Emmenagogue and abortifacients