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Chemical Compound Review

rutoside     2-(3,4-dihydroxyphenyl)-5,7- dihydroxy-3...

Synonyms: Oxyritin, Rutabion, Rutosido, Sophorin, Tanrutin, ...
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Disease relevance of RUTIN


High impact information on RUTIN

  • Oral streptococci are described that hydrolyze the dietary glycoside rutin (CAS: 153-18-4), resulting in mutagenic activity [6].
  • Reversibility experiments demonstrated a religation of the bioflavonoid as well as the VP16-induced MLL cleavage site [7].
  • Exposure to UVB strongly increased COX-2 protein expression in mouse 308 keratinocytes, and this induction was inhibited by apigenin, a nonmutagenic bioflavonoid that has been shown to prevent mouse skin carcinogenesis induced by both chemical carcinogens and UV exposure [8].
  • This report describes a novel potential of bioflavonoid quercetin as an inhibitor of monocyte chemoattractant protein-1 (MCP-1) in glomerular cells [9].
  • Apigenin, a dietary bioflavonoid with anticarcinogenic properties, was highly cytotoxic for HeLa cells (incubated with 0.5% FBS) [10].

Chemical compound and disease context of RUTIN


Biological context of RUTIN


Anatomical context of RUTIN


Associations of RUTIN with other chemical compounds


Gene context of RUTIN


Analytical, diagnostic and therapeutic context of RUTIN


  1. o-(beta-Hydroxyethyl)-rutoside-mediated protection of renal injury associated with cis-diamminedichloroplatinum(II)/hyperthermia treatment. Bull, J.M., Strebel, F.R., Sunderland, B.A., Bulger, R.E., Edwards, M., Siddik, Z.H., Newman, R.A. Cancer Res. (1988) [Pubmed]
  2. Intestinal anti-inflammatory activity of morin on chronic experimental colitis in the rat. Gálvez, J., Coelho, G., Crespo, M.E., Cruz, T., Rodríguez-Cabezas, M.E., Concha, A., Gonzalez, M., Zarzuelo, A. Aliment. Pharmacol. Ther. (2001) [Pubmed]
  3. Quercetin, a bioflavonoid, attenuates haloperidol-induced orofacial dyskinesia. Naidu, P.S., Singh, A., Kulkarni, S.K. Neuropharmacology (2003) [Pubmed]
  4. Selective inhibition of NF-kappaB activation by the flavonoid hepatoprotector silymarin in HepG2. Evidence for different activating pathways. Saliou, C., Rihn, B., Cillard, J., Okamoto, T., Packer, L. FEBS Lett. (1998) [Pubmed]
  5. Reduction of plasma lipid and homocysteine levels by pyridoxine, folate, cobalamin, choline, riboflavin, and troxerutin in atherosclerosis. Olszewski, A.J., Szostak, W.B., Bialkowska, M., Rudnicki, S., McCully, K.S. Atherosclerosis (1989) [Pubmed]
  6. Characterization of oral streptococci that activate the dietary glycoside rutin to a mutagen. Shillitoe, E.J., Hoover, C.I., Fisher, S.J., Abdel-Salam, M., Greenspan, J.S. J. Natl. Cancer Inst. (1984) [Pubmed]
  7. Dietary bioflavonoids induce cleavage in the MLL gene and may contribute to infant leukemia. Strick, R., Strissel, P.L., Borgers, S., Smith, S.L., Rowley, J.D. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  8. Apigenin prevents UVB-induced cyclooxygenase 2 expression: coupled mRNA stabilization and translational inhibition. Tong, X., Van Dross, R.T., Abu-Yousif, A., Morrison, A.R., Pelling, J.C. Mol. Cell. Biol. (2007) [Pubmed]
  9. Bioflavonoid quercetin inhibits interleukin-1-induced transcriptional expression of monocyte chemoattractant protein-1 in glomerular cells via suppression of nuclear factor-kappaB. Ishikawa, Y., Sugiyama, H., Stylianou, E., Kitamura, M. J. Am. Soc. Nephrol. (1999) [Pubmed]
  10. Unbalanced activation of ERK1/2 and MEK1/2 in apigenin-induced HeLa cell death. Llorens, F., Miró, F.A., Casañas, A., Roher, N., Garcia, L., Plana, M., Gómez, N., Itarte, E. Exp. Cell Res. (2004) [Pubmed]
  11. The intestinal anti-inflammatory effect of quercitrin is associated with an inhibition in iNOS expression. Camuesco, D., Comalada, M., Rodríguez-Cabezas, M.E., Nieto, A., Lorente, M.D., Concha, A., Zarzuelo, A., Gálvez, J. Br. J. Pharmacol. (2004) [Pubmed]
  12. Homocysteine content of plasma in ischemic heart disease, the reducing effect of pyridoxine, folate, cobalamin, choline, riboflavin and troxerutin. Correction of a calculation error. Olszewski, A.J. Atherosclerosis (1991) [Pubmed]
  13. Evaluation of the safety of a coumarin-troxerutin combination. Bruppacher, R., Rieckemann, B., Naser-Hijazi, B., Wüstenberg, P. Pharmacoepidemiology and drug safety. (1998) [Pubmed]
  14. Antithrombotics in view of thrombosis models. Hladovec, J. Thromb. Res. (1986) [Pubmed]
  15. Protective effect of natural flavonoids on rat peritoneal macrophages injury caused by asbestos fibers. Kostyuk, V.A., Potapovich, A.I., Speransky, S.D., Maslova, G.T. Free Radic. Biol. Med. (1996) [Pubmed]
  16. Inhibition of heat-induced phosphorylation of stathmin by the bioflavonoid quercetin. Nagasaka, Y., Fijimoto, M., Arai, H., Nakamura, K. Electrophoresis (2002) [Pubmed]
  17. Effect of rutin and its copper complex on superoxide formation and lipid peroxidation in rat liver microsomes. Afanas'ev, I.B., Ostrachovich, E.A., Korkina, L.G. FEBS Lett. (1998) [Pubmed]
  18. A novel endocrine-disrupting agent in corn with mitogenic activity in human breast and prostatic cancer cells. Markaverich, B., Mani, S., Alejandro, M.A., Mitchell, A., Markaverich, D., Brown, T., Velez-Trippe, C., Murchison, C., O'Malley, B., Faith, R. Environ. Health Perspect. (2002) [Pubmed]
  19. Selective inhibition of a cyclic nucleotide independent protein kinase (G type casein kinase) by quercetin and related polyphenols. Cochet, C., Feige, J.J., Pirollet, F., Keramidas, M., Chambaz, E.M. Biochem. Pharmacol. (1982) [Pubmed]
  20. Inhibition of (Na+, K+)adenosine triphosphatase and its partial reactions by quercetin. Kuriki, Y., Racker, E. Biochemistry (1976) [Pubmed]
  21. Effects of quercetin on single Ca(2+) release channel behavior of skeletal muscle. Lee, E.H., Meissner, G., Kim, d.o. .H. Biophys. J. (2002) [Pubmed]
  22. Inhibition of N-formylmethionyl-leucyl-phenylalanine-stimulated tyrosine phosphorylation and phospholipase D activation by quercetin in rabbit neutrophils. Takemura, O.S., Banno, Y., Nozawa, Y. Biochem. Pharmacol. (1997) [Pubmed]
  23. Bioflavonoid effects on in vitro cultures of Plasmodium falciparum. Inhibition of permeation pathways induced in the host cell membrane by the intraerythrocytic parasite. Silfen, J., Yanai, P., Cabantchik, Z.I. Biochem. Pharmacol. (1988) [Pubmed]
  24. Preliminary assessment of luteolin as an affinity ligand for type II estrogen--binding sites in rat uterine nuclear extracts. Markaverich, B.M., Gregory, R.R. Steroids (1993) [Pubmed]
  25. Consumption of high doses of chlorogenic acid, present in coffee, or of black tea increases plasma total homocysteine concentrations in humans. Olthof, M.R., Hollman, P.C., Zock, P.L., Katan, M.B. Am. J. Clin. Nutr. (2001) [Pubmed]
  26. Interaction between quercetin, TPA and DDT in the V79 metabolic cooperation assay. Wärngård, L., Flodström, S., Ljungquist, S., Ahlborg, U.G. Carcinogenesis (1987) [Pubmed]
  27. Influence of O-(beta-hydroxyethyl)-rutoside or venoruton on lactate dehydrogenase of human cultured varicose veins. Matagne, D., Hamoir, G. Biochem. Pharmacol. (1975) [Pubmed]
  28. Quercetin, a bioflavonoid, inhibits the increase of human multidrug resistance gene (MDR1) expression caused by arsenite. Kioka, N., Hosokawa, N., Komano, T., Hirayoshi, K., Nagata, K., Ueda, K. FEBS Lett. (1992) [Pubmed]
  29. Endothelial nitric oxide production stimulated by the bioflavonoid chrysin in rat isolated aorta. Villar, I.C., Vera, R., Galisteo, M., O'Valle, F., Romero, M., Zarzuelo, A., Duarte, J. Planta Med. (2005) [Pubmed]
  30. Quercetin inhibits Shc- and phosphatidylinositol 3-kinase-mediated c-Jun N-terminal kinase activation by angiotensin II in cultured rat aortic smooth muscle cells. Yoshizumi, M., Tsuchiya, K., Kirima, K., Kyaw, M., Suzaki, Y., Tamaki, T. Mol. Pharmacol. (2001) [Pubmed]
  31. Quercetin, a bioflavonoid, inhibits the induction of interleukin 8 and monocyte chemoattractant protein-1 expression by tumor necrosis factor-alpha in cultured human synovial cells. Sato, M., Miyazaki, T., Kambe, F., Maeda, K., Seo, H. J. Rheumatol. (1997) [Pubmed]
  32. The antiproliferative effect of Quercetin in cancer cells is mediated via inhibition of the PI3K-Akt/PKB pathway. Gulati, N., Laudet, B., Zohrabian, V.M., Murali, R., Jhanwar-Uniyal, M. Anticancer Res. (2006) [Pubmed]
  33. Glucuronidation of bioflavonoids by human UGT1A10: structure-function relationships. Lewinsky, R.H., Smith, P.A., Mackenzie, P.I. Xenobiotica (2005) [Pubmed]
  34. Growth of a human mammary tumor cell line is blocked by galangin, a naturally occurring bioflavonoid, and is accompanied by down-regulation of cyclins D3, E, and A. Murray, T.J., Yang, X., Sherr, D.H. Breast Cancer Res. (2006) [Pubmed]
  35. The hypoglycemic effects of hesperidin and naringin are partly mediated by hepatic glucose-regulating enzymes in C57BL/KsJ-db/db mice. Jung, U.J., Lee, M.K., Jeong, K.S., Choi, M.S. J. Nutr. (2004) [Pubmed]
  36. Liquid chromatography/tandem mass spectrometry assay for the quantification of troxerutin in human plasma. Liu, F., Xu, Y., Rui, L., Gao, S., Dong, H., Guo, Q. Rapid Commun. Mass Spectrom. (2006) [Pubmed]
  37. Purification and characterization of nuclear type II [(3)H]estradiol binding sites from the rat uterus: covalent labeling with [(3)H]luteolin. Markaverich, B.M., Shoulars, K., Brown, M.A. Steroids (2001) [Pubmed]
  38. Study on the polarographic catalytic wave of vitamin P in the presence of persulfate and its application. Song, J.F., He, P., Guo, W. Anal. Biochem. (2002) [Pubmed]
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