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Chemical Compound Review

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

Synonyms: AGN-PC-00YHT7, SureCN765367, NSC-44184, AC1Q6OSJ, NSC44184, ...
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Disease relevance of hesperidin

  • When fed the test compounds singly or the combination regimen after 4-NQO exposure, the frequency of tongue cancer was also decreased [diosmin, 77% reduction (P < 0.005); hesperidin, 62% reduction (P < 0.05); and the combination regimen, 77% (P < 0.005)] [1].
  • The combination regimen during the initiation and post-initiation stages also inhibited the development of colonic neoplasms, but the tumor data did not indicate any beneficial effect of diosmin and hesperidin administered together as compared with when these agents were given individually [2].
  • The current results suggest that hesperidin and naringin both play important roles in preventing the progression of hyperglycemia, partly by increasing hepatic glycolysis and glycogen concentration and/or by lowering hepatic gluconeogenesis [3].
  • The purpose of this study was to examine whether hesperidin inhibits bone loss in ovariectomized mice (OVX), an animal model of postmenopausal osteoporosis [4].
  • Daflon 500 mg, is a micronized purified flavonoid fraction, containing 90% w/w diosmin and 10% w/w of flavonoids expressed as hesperidin, used clinically in the treatment of chronic venous insufficiency and hemorrhoidal disease [5].

High impact information on hesperidin

  • The modifying effects of the two flavonoids diosmin and hesperidin given during the initiation and postinitiation phases of oral carcinogenesis initiated with 4-nitroquinoline 1-oxide (4-NQO) were investigated in male F344 rats [1].
  • At 6 weeks of age, rats were divided into experimental and control groups and fed the diet containing beta-carotene, hesperidin, or curcumin at a dose of 0.5 g/kg diet (500 ppm) [6].
  • Cumulative urinary recovery indicated low bioavailability ( < 25%) of naringin and hesperidin [7].
  • Micronised purified flavonoid fraction (MPFF) [Daflon 500 mg], an oral phlebotropic drug consisting of 90% micronised diosmin and 10% flavonoids expressed as hesperidin, improves venous tone and lymphatic drainage, and reduces capillary hyperpermeability by protecting the microcirculation from inflammatory processes [8].
  • In the present study, we investigated the modifying effects of a commercial Satsuma mandarin (Citrus unshiu Marc.) juice (MJ) and those of MJ2 and MJ5, which were prepared from MJ and are richer in beta-cryptoxanthin and hesperidin than MJ, on the occurrence of colonic tumors induced by AOM in male F344 rats [9].

Chemical compound and disease context of hesperidin


Biological context of hesperidin

  • These results indicate that diosmin and hesperidin, both alone and in combination, act as a chemopreventive agent against colon carcinogenesis, and such effects may be partly due to suppression of cell proliferation in the colonic crypts, although precise mechanisms should be clarified [2].
  • The AUC for hesperetin after consuming the hesperetin-7-glucoside juice was improved to the level of the "high" dose hesperidin juice [4.16+/-1.50 mmol/(L.h)] [15].
  • Two other flavonoids tested, rutin and hesperidin, were ineffective in inhibiting cell growth [16].
  • In OVX mice, the bone mineral density of the femur was lower than in the sham group (P < 0.05) and this bone loss was significantly prevented by dietary hesperidin or alpha-glucosylhesperidin [4].
  • Crude flavonoids, eriocitrin, and hesperidin suppressed the oxidative stress in the diabetic rats [17].

Anatomical context of hesperidin


Associations of hesperidin with other chemical compounds

  • We have reported protective effects of dietary administration of a powder "CHRP" containing high amounts of beta-cryptoxanthin and hesperidin prepared from a Satsuma mandarin (Citrus unshiu Marc.) juice on azoxymethane (AOM)-induced rat aberrant crypt foci through suppression of crypt cell proliferation and/or induction of detoxifying enzymes [9].
  • We conclude that berberine, curcumin and hesperidin can increase mucin release by directly acting on airway mucin-secreting cells and suggest that these agents be further studied for possible use as mild expectorants during the treatment of chronic airway diseases [21].
  • The oxidative stress of eriocitrin (eriodictyol 7-O-beta-rutinoside) and hesperidin (hesperetin 7-O-beta-rutinoside) on streptozotocin-induced diabetic rats was investigated [17].
  • Attempts to cure pAM1 failed, however a mutant with reduced plasmid content was obtained, which showed reduced ability to degrade the flavonoid rutinosides rutin and hesperidin [22].
  • HPLC/UV (diode array detector) analysis demonstrated that hesperidin was the major flavanone and nobiletin and heptamethoxyflavone were the major polymethoxylated flavones [23].

Gene context of hesperidin

  • Our data indicate hesperidin as a COX-2 and iNOS inhibitor, which might be related to the anti-inflammatory and anti-tumorigenic efficacies [24].
  • Inhibition of inducible isoforms of cyclooxygenase and nitric oxide synthase by flavonoid hesperidin in mouse macrophage cell line [24].
  • Male C57BL/KsJ-db/db mice (db/db mice, 5 wk old), an animal model for type 2 diabetes, were fed a nonpurified diet for 2 wk and then were fed an AIN-76 control diet or the control diet supplemented with hesperidin (0.2 g/kg diet) or naringin (0.2 g/kg diet) [3].
  • Colony stimulating factor-inducing activity of hesperidin [25].
  • Treatment with hesperidin suppressed production of PGE2, nitrogen dioxide (NO2), and expression of iNOS protein [24].

Analytical, diagnostic and therapeutic context of hesperidin

  • Eriocitrin and hesperidin could be identified as characteristic flavanones and chiral separation of their diastereomers could be achieved according to the developed chiral method by capillary electrophoresis using a 0.2 M borate buffer at pH 10.0 and with 5 mM gamma-CD as chiral selector [26].
  • CONCLUSIONS: A vascular protector such as micronized diosmine hesperidine with recommended corticosteroid premedication and benzopyrones may be useful in preventing and treating docetaxel-induced fluid retention [27].
  • Determination of hesperidin in Pericarpium Citri Reticulatae by semi-micro HPLC with electrochemical detection [28].
  • Determination of hesperidin contents in Pericarpium Citri Reticulatae was performed by a simple extraction with methanol and semi-micro high-performance liquid chromatography with electrochemical detection (muHPLC-ECD) [28].
  • In the present study, we identified the chemical structures and concentrations of the major conjugated metabolites in rat plasma after oral administration of hesperidin [29].


  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. 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]
  3. 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]
  4. Hesperidin, a citrus flavonoid, inhibits bone loss and decreases serum and hepatic lipids in ovariectomized mice. Chiba, H., Uehara, M., Wu, J., Wang, X., Masuyama, R., Suzuki, K., Kanazawa, K., Ishimi, Y. J. Nutr. (2003) [Pubmed]
  5. Comparison of the absorption of micronized (Daflon 500 mg) and nonmicronized 14C-diosmin tablets after oral administration to healthy volunteers by accelerator mass spectrometry and liquid scintillation counting. Garner, R.C., Garner, J.V., Gregory, S., Whattam, M., Calam, A., Leong, D. Journal of pharmaceutical sciences. (2002) [Pubmed]
  6. Chemoprevention of 4-nitroquinoline 1-oxide-induced oral carcinogenesis by dietary curcumin and hesperidin: comparison with the protective effect of beta-carotene. Tanaka, T., Makita, H., Ohnishi, M., Hirose, Y., Wang, A., Mori, H., Satoh, K., Hara, A., Ogawa, H. Cancer Res. (1994) [Pubmed]
  7. Flavanone absorption after naringin, hesperidin, and citrus administration. Ameer, B., Weintraub, R.A., Johnson, J.V., Yost, R.A., Rouseff, R.L. Clin. Pharmacol. Ther. (1996) [Pubmed]
  8. Micronised purified flavonoid fraction: a review of its use in chronic venous insufficiency, venous ulcers and haemorrhoids. Lyseng-Williamson, K.A., Perry, C.M. Drugs (2003) [Pubmed]
  9. Suppression of azoxymethane-induced colon carcinogenesis in male F344 rats by mandarin juices rich in beta-cryptoxanthin and hesperidin. Tanaka, T., Kohno, H., Murakami, M., Shimada, R., Kagami, S., Sumida, T., Azuma, Y., Ogawa, H. Int. J. Cancer (2000) [Pubmed]
  10. Effect of citrus flavonoids on lipid metabolism and glucose-regulating enzyme mRNA levels in type-2 diabetic mice. Jung, U.J., Lee, M.K., Park, Y.B., Kang, M.A., Choi, M.S. Int. J. Biochem. Cell Biol. (2006) [Pubmed]
  11. 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]
  12. Subchronic toxicity study of methyl hesperidin in mice. Kawabe, M., Tamano, S., Shibata, M.A., Hirose, M., Fukushima, S., Ito, N. Toxicol. Lett. (1993) [Pubmed]
  13. Protective activity of hesperidin and lipoic acid against sodium arsenite acute toxicity in mice. das Neves, R.N., Carvalho, F., Carvalho, M., Fernandes, E., Soares, E., de Bastos, M.L., de Pereira, M.L. Toxicologic pathology. (2004) [Pubmed]
  14. Oral administration of purified micronized flavonoid fraction suppresses leukocyte adhesion in ischemia-reperfusion injury: in vivo observations in the hamster skin fold. Friesenecker, B., Tsai, A.G., Allegra, C., Intaglietta, M. International journal of microcirculation, clinical and experimental / sponsored by the European Society for Microcirculation. (1994) [Pubmed]
  15. Bioavailability is improved by enzymatic modification of the citrus flavonoid hesperidin in humans: a randomized, double-blind, crossover trial. Nielsen, I.L., Chee, W.S., Poulsen, L., Offord-Cavin, E., Rasmussen, S.E., Frederiksen, H., Enslen, M., Barron, D., Horcajada, M.N., Williamson, G. J. Nutr. (2006) [Pubmed]
  16. Inhibitory effect of quercetin on OVCA 433 cells and presence of type II oestrogen binding sites in primary ovarian tumours and cultured cells. Scambia, G., Ranelletti, F.O., Panici, P.B., Piantelli, M., Bonanno, G., De Vincenzo, R., Ferrandina, G., Rumi, C., Larocca, L.M., Mancuso, S. Br. J. Cancer (1990) [Pubmed]
  17. Protective effects of lemon flavonoids on oxidative stress in diabetic rats. Miyake, Y., Yamamoto, K., Tsujihara, N., Osawa, T. Lipids (1998) [Pubmed]
  18. 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]
  19. Rutinoside at C7 attenuates the apoptosis-inducing activity of flavonoids. Chen, Y.C., Shen, S.C., Lin, H.Y. Biochem. Pharmacol. (2003) [Pubmed]
  20. Effect of hyaluronidase, beta-glucuronidase and beta-N-acetylglucosaminidase inhibitors on sperm penetration of the mouse oocyte. Joyce, C.L., Mack, S.R., Anderson, R.A., Zaneveld, L.J. Biol. Reprod. (1986) [Pubmed]
  21. Effects of baicalein, berberine, curcumin and hesperidin on mucin release from airway goblet cells. Lee, C.J., Lee, J.H., Seok, J.H., Hur, G.M., Park, Y.C., Seol, I.C., Kim, Y.H. Planta Med. (2003) [Pubmed]
  22. Identification of linear plasmid pAM1 in the flavonoid degrading strain Actinoplanes missouriensis(T) (DSM 43046). Rose, K., Fetzner, S. Plasmid (2006) [Pubmed]
  23. Effect of gamma-irradiation on phenolic compounds and phenylalanine ammonia-lyase activity during storage in relation to peel injury from peel of Citrus clementina hort. Ex. tanaka. Oufedjikh, H., Mahrouz, M., Amiot, M.J., Lacroix, M. J. Agric. Food Chem. (2000) [Pubmed]
  24. Inhibition of inducible isoforms of cyclooxygenase and nitric oxide synthase by flavonoid hesperidin in mouse macrophage cell line. Sakata, K., Hirose, Y., Qiao, Z., Tanaka, T., Mori, H. Cancer Lett. (2003) [Pubmed]
  25. Colony stimulating factor-inducing activity of hesperidin. Kawaguchi, K., Kikuchi, S., Takayanagi, K., Yoshikawa, T., Kumazawa, Y. Planta Med. (1999) [Pubmed]
  26. Chiral separation of six diastereomeric flavanone-7-O-glycosides by capillary electrophoresis and analysis of lemon juice. Gel-Moreto, N., Streich, R., Galensa, R. Journal of chromatography. A. (2001) [Pubmed]
  27. The pathophysiological mechanism of fluid retention in advanced cancer patients treated with docetaxel, but not receiving corticosteroid comedication. Béhar, A., Pujade-Lauraine, E., Maurel, A., Brun, M.D., Chauvin, F.F., Feuilhade de Chauvin, F., Oulid-Aissa, D., Hille, D. British journal of clinical pharmacology. (1997) [Pubmed]
  28. Determination of hesperidin in Pericarpium Citri Reticulatae by semi-micro HPLC with electrochemical detection. Xia, J., Kotani, A., Hakamata, H., Kusu, F. Journal of pharmaceutical and biomedical analysis. (2006) [Pubmed]
  29. Identification and quantification of the conjugated metabolites derived from orally administered hesperidin in rat plasma. Matsumoto, H., Ikoma, Y., Sugiura, M., Yano, M., Hasegawa, Y. J. Agric. Food Chem. (2004) [Pubmed]
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