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Chemical Compound Review

Barosmin     5-hydroxy-2-(3-hydroxy-4- methoxy-phenyl)-7...

Synonyms: Diosmine, Diovenor, Diosmil, Diosminum, Flebosten, ...
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Disease relevance of diosmin

  • These findings suggest that supplementation with the flavonoids diosmin and hesperidin, individually and in combination, is effective in inhibiting the development of oral neoplasms induced by 4-NQO, and such inhibition might be related to suppression of increased cell proliferation caused by 4-NQO in the oral mucosa [1].
  • A number of oesophageal neoplasms developed in rats treated with MNAN alone (75% and 100% incidences of carcinoma and papilloma, respectively). 'Initiation' feeding of diosmin significantly decreased the incidence of squamous cell carcinoma (P < 0.05) [2].
  • At the end of the study (32 weeks), the incidence and multiplicity of neoplasms (adenoma and adenocarcinoma) in the large intestine of rats initiated with AOM together with, or followed by, a diet containing diosmin or hesperidin were significantly smaller than those of rats given AOM alone (P <0.001) [3].
  • The diosmin and placebo groups, with 50 patients each, were comparable in age, sex, symptoms, and the severity of the underlying hemorrhoids [4].
  • Anti-inflammatory activity of diosmin and hesperidin in rat colitis induced by TNBS [5].

High impact information on diosmin


Chemical compound and disease context of diosmin


Biological context of diosmin

  • IQ induced mutagenesis was significantly inhibited by each flavonoid except diosmin at all three doses [9].
  • 1. The kinetics and metabolism of diosmin and diosmetin were investigated in the isolated perfused rat liver in order to assess the role of the liver [13].
  • That means, the IC50 value of LPS in the combination with 8 mumol/l diosmin was shifted from 31 to 70 ng/ml in a concentration dependent manner [14].
  • This modulation can be obtained with flavonoids, such as S 5682, a precise fraction of diosmin and hesperidin, which reduces the vascular permeability of the rabbit skin and increases the resistance of rat microvessels [15].
  • Pharmacokinetics and metabolism of oral diosmin in healthy volunteers [16].

Anatomical context of diosmin


Associations of diosmin with other chemical compounds

  • Distribution of Flavone Glycoside Diosmin in Hyssopus officinalis Plants: Changes During Growth [21].
  • Simultaneous reversed-phase high-performance liquid chromatographic method for the determination of diosmin, hesperidin and naringin in different citrus fruit juices and pharmaceutical formulations [22].
  • In the NNK metabolism experiments in vitro incubations contained 3 microCi [5-H3] NNK, 0.5 mg microsomal protein and 0.5 mumole of the citrus phytochemical diosmin, naringin, naringenin, quercetin or rutin [23].
  • The greatest reduction in the number of metastatic nodules (52%) was obtained with diosmin; similarly, the percentages of implantation, growth index, and invasion index (79.40, 67.44, and 45.23%, respectively), were all compared with those of the ethanol group, considered to be an effective control group [24].
  • Catechin inhibited the in vitro O-deethylation of EFC only in microsomes from 6-month-old rats whereas diosmin inhibited the reaction only in microsomes from 20-month-old rats [25].

Gene context of diosmin


Analytical, diagnostic and therapeutic context of diosmin


  1. Chemoprevention of 4-nitroquinoline 1-oxide-induced oral carcinogenesis in rats by flavonoids diosmin and hesperidin, each alone and in combination. Tanaka, T., Makita, H., Ohnishi, M., Mori, H., Satoh, K., Hara, A., Sumida, T., Fukutani, K., Tanaka, T., Ogawa, H. Cancer Res. (1997) [Pubmed]
  2. Modulation of N-methyl-N-amylnitrosamine-induced rat oesophageal tumourigenesis by dietary feeding of diosmin and hesperidin, both alone and in combination. Tanaka, T., Makita, H., Kawabata, K., Mori, H., Kakumoto, M., Satoh, K., Hara, A., Sumida, T., Fukutani, K., Tanaka, T., Ogawa, H. Carcinogenesis (1997) [Pubmed]
  3. Chemoprevention of azoxymethane-induced rat colon carcinogenesis by the naturally occurring flavonoids, diosmin and hesperidin. Tanaka, T., Makita, H., Kawabata, K., Mori, H., Kakumoto, M., Satoh, K., Hara, A., Sumida, T., Tanaka, T., Ogawa, H. Carcinogenesis (1997) [Pubmed]
  4. Clinical trial of oral diosmin (Daflon) in the treatment of hemorrhoids. Thanapongsathorn, W., Vajrabukka, T. Dis. Colon Rectum (1992) [Pubmed]
  5. Anti-inflammatory activity of diosmin and hesperidin in rat colitis induced by TNBS. Crespo, M.E., Gálvez, J., Cruz, T., Ocete, M.A., Zarzuelo, A. Planta Med. (1999) [Pubmed]
  6. Diosmin and diosmetin are agonists of the aryl hydrocarbon receptor that differentially affect cytochrome P450 1A1 activity. Ciolino, H.P., Wang, T.T., Yeh, G.C. Cancer Res. (1998) [Pubmed]
  7. Chemopreventive effects of diosmin and hesperidin on N-butyl-N-(4-hydroxybutyl)nitrosamine-induced urinary-bladder carcinogenesis in male ICR mice. Yang, M., Tanaka, T., Hirose, Y., Deguchi, T., Mori, H., Kawada, Y. Int. J. Cancer (1997) [Pubmed]
  8. Flavonoid treatment in patients with healed venous ulcer: flow cytometry analysis suggests increased CD11b expression on neutrophil granulocytes in the circulation. Danielsson, G., Norgren, L., Truedsson, L., Andreasson, A., Danielsson, P., Nilsson, A., Swartbol, P. Vascular medicine (London, England) (2003) [Pubmed]
  9. Effects of citrus flavonoids on the mutagenicity of heterocyclic amines and on cytochrome P450 1A2 activity. Bear, W.L., Teel, R.W. Anticancer Res. (2000) [Pubmed]
  10. Protective effect of diosmetin on in vitro cell membrane damage and oxidative stress in cultured rat hepatocytes. Villa, P., Cova, D., De Francesco, L., Guaitani, A., Palladini, G., Perego, R. Toxicology (1992) [Pubmed]
  11. Amine uptake inhibition by diosmin and diosmetin in human neuronal and neuroendocrine cell lines. Sher, E., Codignola, A., Biancardi, E., Cova, D., Clementi, F. Pharmacol. Res. (1992) [Pubmed]
  12. Venoruton vs Daflon: evaluation of effects on quality of life in chronic venous insufficiency. Cesarone, M.R., Belcaro, G., Pellegrini, L., Ledda, A., Vinciguerra, G., Ricci, A., Di Renzo, A., Ruffini, I., Gizzi, G., Ippolito, E., Fano, F., Dugall, M., Acerbi, G., Cornelli, U., Hosoi, M., Cacchio, M. Angiology. (2006) [Pubmed]
  13. Pharmacokinetic studies of diosmin and diosmetin in perfused rat liver. Perego, R., Beccaglia, P., Angelini, M., Villa, P., Cova, D. Xenobiotica (1993) [Pubmed]
  14. Inhibition of lipopolysaccharide (LPS)-induced endothelial cytotoxicity by diosmin. Melzig, M.F., Loose, R. Die Pharmazie. (1999) [Pubmed]
  15. Biochemical mediators involved in the inflammatory reaction. Protective activity of S 5682. Vargaftig, B.B. International angiology : a journal of the International Union of Angiology. (1988) [Pubmed]
  16. Pharmacokinetics and metabolism of oral diosmin in healthy volunteers. Cova, D., De Angelis, L., Giavarini, F., Palladini, G., Perego, R. International journal of clinical pharmacology, therapy, and toxicology. (1992) [Pubmed]
  17. Diosmin-induced increase in sensitivity to Ca2+ of the smooth muscle contractile apparatus in the rat isolated femoral vein. Savineau, J.P., Marthan, R. Br. J. Pharmacol. (1994) [Pubmed]
  18. Antioxidant activity of micronized diosmin on oxygen species from stimulated human neutrophils. Cypriani, B., Limasset, B., Carrié, M.L., Le Doucen, C., Roussie, M., de Paulet, A.C., Damon, M. Biochem. Pharmacol. (1993) [Pubmed]
  19. Effects of the phlebotropic drug Daflon 500 mg on postischemic reperfusion injury in striated skin muscle: a histomorphologic study in the hamster. Pickelmann, S., Nolte, D., Leiderer, R., Möllmann, M., Schütze, E., Messmer, K. J. Lab. Clin. Med. (1999) [Pubmed]
  20. The effect of the flavonoid diosmin, grape seed extract and red wine on the pulmonary metastatic B16F10 melanoma. Martínez, C., Vicente, V., Yáñez, J., Alcaraz, M., Castells, M.T., Canteras, M., Benavente-García, O., Castillo, J. Histol. Histopathol. (2005) [Pubmed]
  21. Distribution of Flavone Glycoside Diosmin in Hyssopus officinalis Plants: Changes During Growth. Marin, F.R., Ortuño, A., Benavente-Garcia, O., Del Rio, J.A. Planta Med. (1998) [Pubmed]
  22. Simultaneous reversed-phase high-performance liquid chromatographic method for the determination of diosmin, hesperidin and naringin in different citrus fruit juices and pharmaceutical formulations. Kanaze, F.I., Gabrieli, C., Kokkalou, E., Georgarakis, M., Niopas, I. Journal of pharmaceutical and biomedical analysis. (2003) [Pubmed]
  23. Effects of citrus phytochemicals on liver and lung cytochrome P450 activity and on the in vitro metabolism of the tobacco-specific nitrosamine NNK. Bear, W.L., Teel, R.W. Anticancer Res. (2000) [Pubmed]
  24. Treatment of metastatic melanoma B16F10 by the flavonoids tangeretin, rutin, and diosmin. Martínez Conesa, C., Vicente Ortega, V., Yáñez Gascón, M.J., Alcaraz Baños, M., Canteras Jordana, M., Benavente-García, O., Castillo, J. J. Agric. Food Chem. (2005) [Pubmed]
  25. Effects of plant-derived phenols on rat liver cytochrome P450 2B1 activity. Huynh, H.T., Teel, R.W. Anticancer Res. (2002) [Pubmed]
  26. The influence of the fibrinolytic system on the affinity of fibrinogen for the endothelial-plasma interface. Witte, S. Thromb. Res. (1988) [Pubmed]
  27. Comparative effect of tropolone and diosmin on venous COMT and sympathetic activity in rat. Boudet, C., Peyrin, L. Archives internationales de pharmacodynamie et de thérapie. (1986) [Pubmed]
  28. Leukocyte adhesion after oxidant challenge in the hamster cheek pouch microcirculation. Bouskela, E., Cyrino, F.Z., Lerond, L. J. Vasc. Res. (1999) [Pubmed]
  29. Clinical efficacy of micronized purified flavonoid fraction: an overview. Struckmann, J.R. J. Vasc. Res. (1999) [Pubmed]
  30. The effect of diosmin hesperidin on intestinal ischaemia--reperfusion injury. Pehlivan, M., Hazinedaroglu, S.M., Kayaoglu, H.A., Erkek, A.B., Keklik, T., Canbolat, O., Kocak, S. Acta chirurgica Belgica. (2004) [Pubmed]
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