曲克芦丁, Trihydroxyethylrutin

Troxerutin is a flavonoid that has been found in a variety of fruits and vegetables and has diverse biological activities. It reduces D-galactose-induced increases in renal malondialdehyde (MDA) levels and decreases in renal Cu/Zn superoxide dismutase (SOD), catalase, and glutathione peroxidase (GPX) activities in mice when administered at a dose of 150 mg/kg per day, as well as attenuates D-galactose-induced increases in renal levels of NF-κB p65, inducible nitric oxide synthase (iNOS), COX-2, and prostaglandin E2 receptor 2 (EP2). Troxerutin (150 mg/kg per day) reduces blood glucose levels, plasma triglyceride levels, heart rate, and blood pressure in a rat model of type 2 diabetes induced by streptozotocin (STZ;). Troxerutin (150 mg/kg per day) prevents the loss of dopaminergic neurons in the substantia nigra pars compacta (SNC) and reduces apomorphine-induced contralateral rotations in a rat model of Parkinson’s disease induced by 6-OHDA.

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Troxerutin, also known as venoruton or vitamin P4, belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Troxerutin exists as a solid, slightly soluble (in water), and a very weakly acidic compound (based on its pKa).

Troxerutin has been used in trials studying the treatment of Chronic Venous Insufficiency.

Troxerutin is a natural compound with a number of pharmacological properties. It is an inhibitor of oxidative phosphorylation, which inhibits the production of ATP from ADP and inorganic phosphate. Troxerutin also has high affinity for heme proteins, which are important for mitochondrial function. The effects on cellular physiology are due to its effect on control analysis and synchronous fluorescence. Troxerutin has been shown to protect against myocardial infarction by preventing the decrease in mitochondrial membrane potential.

Title: Troxerutin

CAS Registry Number: 7085-55-4

CAS Name: 2-[3,4-Bis(2-hydroxyethoxy)phenyl]-3-[[6-O-(6-deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl]oxy]-5-hydroxy-7-(2-hydroxyethoxy)-4H-1-benzopyran-4-one

Additional Names: 7,3¢,4¢-tris[O-(2-hydroxyethyl)]rutin; trioxyethylrutin; tri(hydroxyethyl)rutoside

Trademarks: Posorutin (Ursapharm); Ruven (Mepha); Vastribil (Farmasan); Veinamitol (NEGMA); Veniten (Wyeth)

Molecular Formula: C33H42O19

Molecular Weight: 742.675

Percent Composition: C 53.37%, H 5.70%, O 40.93%

Literature References: The principal component of a mixture, the O-(b-hydroxyethyl)rutosides, which also contains mono-, di-, tetra- and other trihydroxyethyl derivs of rutin, q.v. The mixture is prepd by the hydroxyethylation of the phenolic groups of rutin with glycochlorohydrin in alk medium: J. Favre, CH 349614 (1957); see also GB 833174 (1960 to Zyma), C.A. 54, 21135i (1960). Isolation and identification of major components of the mixture: P. Courbat et al., Helv. Chim. Acta 49, 1203, 1420 (1966). Prepn of troxerutin: P. J. Courbat, US 3420815 (1969 to Zyma). Metabolism in man: A. M. Hackett et al., Arzneim.-Forsch. 26, 925 (1976).

Properties: Yellow powder, mp 181°. Sol in water, glycerol, propylene glycol. Practically insol in cold ethanol, methanol (forms alcoholate), ether, benzene, chloroform.

Melting point: mp 181°

Derivative Type: O-(b-Hydroxyethyl)rutinosides (mixture)

CAS Registry Number: 55965-63-4

Additional Names: HR

Trademarks: Paroven (Zyma); Relvene (Pharmascience); Varemoid (Zyma); Venoruton (Zyma)

Properties: Yellow powder, mp 156°. Sol in water, methanol, glycerol, propylene glycol. Practically insol in cold ethanol (forms alcoholate), ether, benzene, chloroform.

Melting point: mp 156°

Therap-Cat: Treatment of venous disorders.

Keywords: Vasoprotectant.