Rutin

• Rutoside
• Sophorin
• Quercetin- 3-O- rutinoside
• Quercetin- 3-O- glucorhamnosid
• 3,3 ', 4' ,5,7- pentahydroxyflavone - 3-O- rutinoside
• C. I. 75730
• C. I. Natural Yellow 10
• Pseudo vitamin P

C05CA01

Pale yellow to greenish needles (trihydrate )

Fixed

214-215 ° C ( decomposition)

• Insoluble in chloroform, diethyl ether and petroleum ether
• Poorly in boiling water and ethanol
• Soluble in alkaline solutions, pyridine and formamide

Hydrate

Attention

950 mg · kg -1 ( LD50, mouse, i.v.)

Template: Infobox chemical / molecular formula search available

Rutin is a flavonoid glycoside and quercetin of the Dissacharid rutinose, which is composed of rhamnose and glucose. Rutin is formed by many plants as a dye for the protection against UV radiation. Antioxidant effects on humans, as with many flavonoids detected; Starting points of rutin in particular the blood vessels and the intestine.

Chemical Properties

Rutin is a pale yellow to yellow powder, insoluble in water (<5 g / l) and well, generally better dissolves in hot alcohol in polar and nonpolar solvents. Rutin is stable in air and has an antioxidant effect; it is capable of dissolved Vitamin C, such as to stabilize fruit juices. Rutin melts at a temperature around 200 ° C. Elimination of the sugar residue produced quercetin. Rutin together with metal ion complexes, especially iron, copper and aluminum; it should not be stored in such containers. General goes rutin similar reactions as the other flavonoids also.

Biosynthesis and occurrence

Rutin is produced by many plants in large amounts to protect against UV radiation; the rutin content is therefore dependent on many species of plants on the height above sea level of the growth site and is many times higher in the aboveground plant parts. In addition, the plant benefits from the weak antimicrobial properties of the substance. As a flavonoid, it arises from the Phenylpropanoidstoffwechsel and the polyketide. Specifically, the naringenin formed in Flavonoidstoffwechsel ( flavanone ) is hydrogenated to Flavononol this hydroxylation to dihydroquercetin and then dehydrated to quercetin, which is finally glycosylated.

The plants with the highest rutin content ( in dry matter ) are:

Wild pansy (Viola tricolor, 25 % flowering), Japanese pagoda tree ( Styphnolobium japonicum, 15-20 % bloom or flower buds, leaves 4% ), Buckwheat ( Fagopyrum esculentum, 2-8 % leaves, 4-12 % Flowering ), White Mulberry (Morus alba, 6%, leaves), Canadian elderberry (Sambucus nigra subsp. canadensis, 3.5%, leaves), parsley ( crispum Petroselinum, 3% leaves), smartweed ( Persicaria hydropiper, 3% leaves). St. John's wort (Hypericum perforatum, 2%, upper plant parts ).

Even in buckwheat flour or 0.27 percent rutin were included in an analysis, after all.

Extraction

Pure rutin is currently mainly exported from China and Brazil. In China, rutin was extracted in spite of the large acreage of buckwheat until recently from the leaf buds of the Japanese string tree ( Styphnolobium japonicum) and further processed primarily to Troxerutine. In Brazil, one only housed there jungle plant is used.

The traditional production plant material is 70 - to 85 -percent isopropanol extracted and the solution was then freed from fat ingredients. After concentration, the product crystallizes.

Metabolism

For oral administration rutin is not absorbed as such by the body in the bloodstream. Rather, rutin is partially degraded by the intestinal flora, and these degradation products are the ones who act outside of the intestine. Maximum availability is achieved after six to nine hours after ingestion.

Rutin is initially held in the small intestine in the mucosa and converted by the local flora in quercetin -3 -glucoside, which goes partly into the bloodstream and is converted in the microsomes of the mucosa, but also in the liver to quercetin -3 -glucuronide. The remaining part of rutin acts locally in the gut and is transported into the ileum, where it is eventually degraded by a specific type of local flora ( Eubacterium ramulus ) to derivatives of phenylacetic acid and excreted in the urine. Physiologically significant is only 3,4- dihydroxyphenylacetic acid (3,4- DHPAA ), the anti-cancer properties are attributed.

Effect

There is a clinical trial with 69 patients, which seems to prove for gestational edema, the efficacy of rutin. Several cases of healing of purpura, a vascular disease by oral administration of rutin and vitamin C are known. In animal experiments, it has anti-inflammatory for chemically generated colitis, and still in concentrations of 0.01 percent in the feed.

In 2002, however, five cases were known, which developed after ingestion of rutin an intestinal vein inflammation ( phlebitis ), an otherwise rare disease.

Rutoside ( rutin ) and Troxerutine are approved as an active ingredient in Antihaemorrhagics and veins therapeutics.

Application

Rutin, usually in the form of acid sodium salts, pharmacologically similar to hesperidin against capillary bleeding and any condition associated with increased capillary fragility and membrane permeability states ( for these reasons was rutin formerly often referred to as so-called Antipermeabilitätsfaktor or as vitamin P ) is hereby established - but was in the USA 1970, the approval of rutin and other bioflavonoids withdrawn due to lack of proof of efficacy by the FDA. For the treatment of venous diseases and circulatory disorders synthetic rutin derivatives such as Troxerutine and monoxerutin are often used.