Rutin

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Structural formula
Structural formula of rutin
General
Surname Rutin
other names
  • Rutoside
  • Sophorin
  • Quercetin 3- O rutinoside
  • Quercetin 3 O -glucorhamnoside
  • 3,3 ', 4', 5,7-pentahydroxyflavone-3- O- rutinoside
  • CI 75730
  • CI Natural Yellow 10
  • Pseudovitamin P
Molecular formula C 27 H 30 O 16
Brief description

pale yellow to greenish needles (trihydrate)

External identifiers / databases
CAS number
  • 153-18-4
  • 207671-50-9 (hydrate)
  • 250249-75-3 (trihydrate)
EC number 205-814-1
ECHA InfoCard 100.005.287
PubChem 5280805
ChemSpider 4444362
DrugBank DB01698
Wikidata Q407857
Drug information
ATC code

C05 CA01

properties
Molar mass 610.52 g mol −1
Physical state

firmly

Melting point

214–215 ° C (decomposition)

solubility
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances

hydrate

07 - Warning

Caution

H and P phrases H: 302
P: no P-phrases
Toxicological data

950 mg kg −1 ( LD 50 ,  mouse ,  iv )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Rutin is a flavonoid and a glycoside of quercetin with the disaccharide rutinose , which is composed of rhamnose and glucose . Many plants produce rutin as a dye to protect against UV radiation. As with many flavonoids, antioxidant effects on humans have been demonstrated; The blood vessels and intestines in particular are the starting points of rutin.

Chemical properties

Rutin

Rutin is a pale yellow to yellow powder that dissolves poorly in water (<5 g / l) and well in hot alcohol, generally better in polar than non-polar solvents. Rutin is stable in the air and has an antioxidant effect; it is able to absorb dissolved vitamin C , e.g. B. to stabilize in fruit juices. Rutin melts at a temperature around 200 ° C. Quercetin is formed by splitting off the sugar residue . Rutin forms complex compounds with metal ions, especially with iron, copper and aluminum; it should therefore not be kept in such containers. In general, rutin reacts similarly to the other flavonoids .

Biosynthesis and Occurrence

Many plants produce large quantities of rutin to protect against UV radiation ; the cane content of many plant species is therefore dependent on the height above sea level of the place of growth and is many times higher in the above-ground parts of the plant. In addition, the plant benefits from the weakly antimicrobial properties of the substance. As a flavonoid , it arises from the phenylpropanoid metabolism and the polyketide metabolism. Specifically, the naringenin (flavanone) formed in the flavonoid metabolism is hydrogenated to flavonol , this is hydroxylated to dihydroquercetin and then dehydrated to quercetin , which is finally glycosylated.

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

Wild pansy ( Viola tricolor )
White Mulberry ( Morus alba )

Wild pansy ( Viola tricolor , 25%, flower), Japanese pagoda tree ( Styphnolobium japonicum , 15–20% flower or flower buds, 4% leaves), buckwheat ( Fagopyrum esculentum , 2–8% leaves, 4–12% flower) , white mulberry ( Morus alba , 6%, leaves), Sambucus canadensis ( Sambucus nigra subsp. canadensis , 3.5%, flowers), parsley ( Petroselinum crispum , 3% leaves), smartweed ( Persicaria hydropiper , 3% sheets). St. John's wort ( Hypericum perforatum , 2%, upper parts of the plant)

Even in buckwheat flour still 0.27 percent rutin were nevertheless included in an analysis.

Extraction

Pure rutin is currently mainly exported from China and Brazil. In China, despite the large cultivation area for buckwheat, until recently rutin was extracted from the buds of the Japanese pagoda tree ( Styphnolobium japonicum ) and mainly processed into troxerutin . In Brazil, a native forest plant is used only there.

In traditional production, plant material is extracted with 70 to 85 percent isopropanol and the fat is then removed from the solution. After concentration, the product crystallizes.

The cane content in buckwheat varies depending on the intensity of UV-B radiation . Flowers have the highest content, followed by leaves and stem.

Rutin was isolated for the first time in 1842 by the Nuremberg pharmacist Weiss, who named the substance after the rue , from which rutin was previously obtained for the treatment of chronic venous insufficiency, but was then replaced by plant species that are more rich in rutin.

metabolism

When given orally, rutin is not absorbed as such by the body in the bloodstream. Rather, rutin is partly broken down by the intestinal flora , and it is these breakdown products that act outside the intestine. The maximum availability is reached after six to nine hours after ingestion.

Rutin is initially retained in the mucosa in the small intestine and converted into quercetin-3-glucoside by the intestinal flora there , which is partially transferred into the blood and converted to quercetin-3-glucuronide in the microsomes of the mucosa, but also in the liver. The remaining part of the rutin acts locally in the intestine and is transported into the ileum , where it is finally broken down by a certain type of intestinal flora there ( Eubacterium ramulus ) into derivatives of phenylacetic acid and excreted in the urine. Only 3,4-dihydroxyphenylacetic acid (3,4-DHPAA), which is said to have anti-cancer properties, is physiologically significant .

effect

There is a clinical study with 69 patients that seems to prove the effectiveness of rutin in gestational edema . Several cases of healing of purpura , a vascular disease, by oral administration of rutin and vitamin C are known. In animal experiments, it has an anti-inflammatory effect on chemically induced colitis , in concentrations of 0.01 percent in the feed.

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

Rutosid (rutin) and troxerutin are approved as active ingredients in antihemorrhagics and venous therapeutics.

application

Rutin, mostly in the form of the acidic sodium salts, is pharmacologically similar to hesperidin used against capillary bleeding and all conditions associated with increased capillary fragility and membrane permeability (for these reasons, rutin was previously often referred to as the so-called antipermeability factor or vitamin P ) - however, in the USA 1970 FDA withdrew approval for rutin and other bioflavonoids due to a lack of proof of their effectiveness. In 1944, rutin was introduced into therapy as a venous drug . Synthetic rutin derivatives such as troxerutin and monoxerutin are often used to treat venous diseases and circulatory disorders .

Individual evidence

  1. ↑ a b c d e f Entry on Rutin. In: Römpp Online . Georg Thieme Verlag, accessed on October 1, 2014.
  2. ↑ a b Datasheet Rutin hydrate from Sigma-Aldrich , accessed on May 29, 2011 ( PDF ).
  3. ^ Entry on rutin in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  4. ^ S. Kreft et al .: Rutin in buckwheat herbs grown at different UV-B radiation levels: comparison of two UV spectrophotometric and an HPLC method. J. Exp. Bot. (2002) 53 (375): 1801-1804. doi : 10.1093 / jxb / erf032
  5. ↑ Dr. Duke's Phytochemical and Ethnobotanical Databases ( Memento of the original from August 19, 2007 in the Internet Archive ) Info: The archive link was automatically inserted and not yet checked. Please check the original and archive link according to the instructions and then remove this notice. @1@ 2Template: Webachiv / IABot / www.ars-grin.gov
  6. ↑ http://www.apotheken-umschau.de/heilpflanze/holunder
  7. ^ GG Franchi et al .: Composition and antioxidant activity in vitro of different St. John's Wort (Hypericum perforatum L.) extracts. Journal of Medicinal Plants Research Vol. 5 (17), pp. 4349-4353, September 9, 2011.
  8. ^ I. Kreft et al .: Rutin content in buckwheat (Fagopyrum esculentum Moench) food materials and products. In: Food Chem . 98/3/ 2006 . Pp. 508-512. doi : 10.1016 / j.foodchem.2005.05.081
  9. ↑ YPS Bajaj (Ed.): Medicinal and Aromatic Plants V. Vol. 24 in the series Biotechnology in Agriculture and Forestry. Springer 1993. p. 208. ISBN 978-3-540-56008-1
  10. ↑ Kreft, S., Štrukelj, B., Gaberščik, A., Kreft, I. (2002). Rutin in buckwheat herbs grown at different UV-B radiation levels: comparison of two UV spectrophotometric and an HPLC method. Journal of Experimental Botany, 53, 375: 1801-1804.
  11. ↑ Christina Becela-Deller: Ruta graveolens L. A medicinal plant in terms of art and cultural history. (Mathematical and natural science dissertation Würzburg 1994) Königshause & Neumann, Würzburg 1998 (= Würzburg medical historical research. Volume 65). ISBN 3-8260-1667-X , pp. 22 and 224.
  12. ↑ See also Chun-Li Yu, B. Swaminathan, LG Butler, DE Pratt: Isolation and identification of rutin as the major mutagen of red wine. In: Mutat. Res. Volume 170, No. 3, 1986, pp. 103-113.
  13. ^ C. Manach et al .: Polyphenols: food sources and bioavailability. Review. At the. J. Clin. Nutr. 79/5/ 2004 . Pp. 727-747. Online version
  14. ↑ H. Schneider, Anaerobic transformation of quercetin-3-glucoside by bacteria from the human intestinal tract. Arch. Microbiol. 171/2/ 1999 . Pp. 81-91 doi : 10.1007 / s002030050682
  15. ↑ C. Morand et al .: Respective bioavailability of quercetin aglycone and its glycosides in a rat model. Biofactors. 12 / 1-4 / 2000 . Pp. 169-174. PMID 11216481
  16. ↑ MR Olthof et al .: Chlorogenic acid, quercetin-3-rutinoside and black tea phenols are extensively metabolized in humans. J Nutr. 133/6/ 2003 . Pp. 1806-1814. PMID 12771321
  17. ^ IB Jaganath et al .: The relative contribution of the small and large intestine to the absorption and metabolism of rutin in man. Free Radic Res. 40/10/ 2006 . Pp. 1035-1046. PMID 17015248
  18. ↑ K. Gao et al .: Of the major phenolic acids formed during human microbial fermentation of tea, citrus, and soy flavonoid supplements, only 3,4-dihydroxyphenylacetic acid has antiproliferative activity. J Nutr. 136/1/ 2006 . Pp. 52-57. PMID 16365058
  19. ^ AA Bamigboye and GJ Hofmeier: Interventions for leg edema and varicosities in pregnancy. What evidence? EUR J Obstet Gynecol Reprod Biol. 129/1/ 2006 . Pp. 3-8. PMID 16678328
  20. ↑ U. Reinhold et al .: Treatment of progressive pigmented purpura with oral bioflavonoids and ascorbic acid: an open pilot study in 3 patients. J Am Acad Dermatol. 41/2/ 1999 . Pp. 207-208. PMID 10426890
  21. ^ F. Laufer: The treatment of progressive pigmented purpura with ascorbic acid and a bioflavonoid rutoside. In: Journal of Drugs in Dermatology . 2006 , Volume 5, pp. 290-293. PMID 16573267
  22. ↑ KH Kwon et al .: Dietary rutin, but not its aglycone quercetin, ameliorates dextran sulfate sodium-induced experimental colitis in mice: attenuation of pro-inflammatory gene expression. Biochem Pharmacol . 69/3/ 2005 . Pp. 395-406. PMID 15652231 . doi : 10.1016 / j.bcp.2004.10.015
  23. ↑ A. Kettaneh et al .: Pseudotumoral enterocolic phlebitis of the cecum and rutoside. A case report (original in French). Rev Med Internal. 23/5/ 2002 . Pp. 465-468. PMID 12064219
  24. ↑ Elof J. Johnson: Rutin and capillary fragility. In: American Journal of Pharmacology. Volume 118, 1946, pp. 164-175.
  25. ^ Franz Berger: Handbook of drug science. Volume 4. Vienna 1954, pp. 432-436.

literature

  • P. Schopfer, A. Brennicke: Plant physiology. 6th edition, Elsevier 2006.