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Chemical Compound Review

AC1L8SMG     5-hydroxy-7-[[5-hydroxy-6- (hydroxymethyl)...

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Disease relevance of Naringoside

  • RESULTS: After adjusting for smoking and intakes of saturated fat and beta-carotene, we found statistically significant inverse associations between lung cancer risk and the main food sources of the flavonoids quercetin (onions and apples) and naringin (white grapefruit) [1].
  • The cytoprotective effect of naringin was apparently limited to normal hepatocytes, since the toxin-induced apoptosis of hepatoma cells, rat or human, was not prevented by the flavonoid [2].
  • Overall, the glycosylated flavonoids (i.e., naringin, a constituent of citrus fruits, and rutin, a constituent of cranberries) induced the greatest response to treatment at the lowest concentration in MDA human breast cancer cells [3].
  • 0, 0.5, 1, 2, 4, 6 and 8 mg/kg body weight of naringin (NIN) (a citrus flavanone) was studied on the alteration in the radiation-induced micronucleated polychromatic (MPCE) and normochromatic (MNCE) erythrocytes in mouse bone marrow exposed to 2 Gy of 60Co gamma-radiation [4].
  • The protective effect of the Citrus flavanone naringin was demonstrated in an endotoxin shock model based on Salmonella infection [5].

High impact information on Naringoside


Chemical compound and disease context of Naringoside


Biological context of Naringoside


Anatomical context of Naringoside


Associations of Naringoside with other chemical compounds

  • To identify phosphoproteins that might play a role in naringin-sensitive hepatocellular cytoskeletal disruption and apoptosis induced by algal toxins, hepatocyte extracts were separated by gel electrophoresis and immunostained with a phosphothreonine-directed antibody [6].
  • The metabolism of chlorogenic acid, naringin, and rutin, representative members of three common families of dietary polyphenols, the hydroxycinnamates, the flavanones, and the flavonols, respectively, was studied in an in vitro mixed culture model of the human colonic microflora [20].
  • The pharmacokinetics of felodipine and its single primary oxidative metabolite, dehydrofelodipine, were studied after drug administration with 200 ml water, grapefruit juice, or naringin in water at the same concentration as the juice in a randomized crossover trial of nine healthy men [21].
  • Temperature- and pH-dependent enantiomerization or epimerization barriers of several flavanones (naringenin, homoeriodictyol) and flavanone-7-O-glycosides (naringin, neohesperidin, prunin, narirutin) in basic media (pH values of 9-11) have been observed [22].
  • This study evaluated the hypothesis that untreated and irradiated grapefruit as well as the isolated citrus compounds naringin and limonin would protect against azoxymethane (AOM)-induced aberrant crypt foci (ACF) by suppressing proliferation and elevating apoptosis through anti-inflammatory activities [23].

Gene context of Naringoside


Analytical, diagnostic and therapeutic context of Naringoside


  1. Intake of flavonoids and lung cancer. Le Marchand, L., Murphy, S.P., Hankin, J.H., Wilkens, L.R., Kolonel, L.N. J. Natl. Cancer Inst. (2000) [Pubmed]
  2. Prevention of toxin-induced cytoskeletal disruption and apoptotic liver cell death by the grapefruit flavonoid, naringin. Blankson, H., Grotterød, E.M., Seglen, P.O. Cell Death Differ. (2000) [Pubmed]
  3. Flavonoids and vitamin E reduce the release of the angiogenic peptide vascular endothelial growth factor from human tumor cells. Schindler, R., Mentlein, R. J. Nutr. (2006) [Pubmed]
  4. The grapefruit flavanone naringin protects against the radiation-induced genomic instability in the mice bone marrow: a micronucleus study. Jagetia, G.C., Reddy, T.K. Mutat. Res. (2002) [Pubmed]
  5. Suppression of infection-induced endotoxin shock in mice by a citrus flavanone naringin. Kawaguchi, K., Kikuchi, S., Hasunuma, R., Maruyama, H., Ryll, R., Kumazawa, Y. Planta Med. (2004) [Pubmed]
  6. Naringin-sensitive phosphorylation of plectin, a cytoskeletal cross-linking protein, in isolated rat hepatocytes. Larsen, A.K., Møller, M.T., Blankson, H., Samari, H.R., Holden, L., Seglen, P.O. J. Biol. Chem. (2002) [Pubmed]
  7. Protection by naringin and some other flavonoids of hepatocytic autophagy and endocytosis against inhibition by okadaic acid. Gordon, P.B., Holen, I., Seglen, P.O. J. Biol. Chem. (1995) [Pubmed]
  8. The effects of naringin and naringenin on endotoxin-induced uveitis in rats. Shiratori, K., Ohgami, K., Ilieva, I., Jin, X.H., Yoshida, K., Kase, S., Ohno, S. Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics. (2005) [Pubmed]
  9. Hypolipidemic effects and absorption of citrus polymethoxylated flavones in hamsters with diet-induced hypercholesterolemia. Kurowska, E.M., Manthey, J.A. J. Agric. Food Chem. (2004) [Pubmed]
  10. Naringin has an antiatherogenic effect with the inhibition of intercellular adhesion molecule-1 in hypercholesterolemic rabbits. Choe, S.C., Kim, H.S., Jeong, T.S., Bok, S.H., Park, Y.B. J. Cardiovasc. Pharmacol. (2001) [Pubmed]
  11. Preventive effect of naringin on lipids, lipoproteins and lipid metabolic enzymes in isoproterenol-induced myocardial infarction in Wistar rats. Rajadurai, M., Stanely Mainzen Prince, P. J. Biochem. Mol. Toxicol. (2006) [Pubmed]
  12. Role of four major components in the effect of Si-Ni-San, a traditional Chinese prescription, against contact sensitivity in mice. Zhang, L., Dong, Y., Sun, Y., Chen, T., Xu, Q. J. Pharm. Pharmacol. (2006) [Pubmed]
  13. Effect of grapefruit juice and naringin on nisoldipine pharmacokinetics. Bailey, D.G., Arnold, J.M., Strong, H.A., Munoz, C., Spence, J.D. Clin. Pharmacol. Ther. (1993) [Pubmed]
  14. Flavonoids as superoxide scavengers and antioxidants. Chen, Y.T., Zheng, R.L., Jia, Z.J., Ju, Y. Free Radic. Biol. Med. (1990) [Pubmed]
  15. The fate of naringin in humans: a key to grapefruit juice-drug interactions? Fuhr, U., Kummert, A.L. Clin. Pharmacol. Ther. (1995) [Pubmed]
  16. Quercetin, a potent and specific inhibitor of the human P-form phenosulfotransferase. Walle, T., Eaton, E.A., Walle, U.K. Biochem. Pharmacol. (1995) [Pubmed]
  17. 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]
  18. Inhibitory effect of grapefruit juice and its bitter principal, naringenin, on CYP1A2 dependent metabolism of caffeine in man. Fuhr, U., Klittich, K., Staib, A.H. British journal of clinical pharmacology. (1993) [Pubmed]
  19. Effect of honey and sugars on the metabolism and disposition of naringin in rabbits. Hou, Y.C., Hsiu, S.L., Huang, T.Y., Yang, C., Tsai, S.Y., Chao, P.D. Planta Med. (2001) [Pubmed]
  20. Colonic metabolism of dietary polyphenols: influence of structure on microbial fermentation products. Rechner, A.R., Smith, M.A., Kuhnle, G., Gibson, G.R., Debnam, E.S., Srai, S.K., Moore, K.P., Rice-Evans, C.A. Free Radic. Biol. Med. (2004) [Pubmed]
  21. Grapefruit juice--felodipine interaction: mechanism, predictability, and effect of naringin. Bailey, D.G., Arnold, J.M., Munoz, C., Spence, J.D. Clin. Pharmacol. Ther. (1993) [Pubmed]
  22. Stereoisomeric separation of flavanones and flavanone-7-O-glycosides by capillary electrophoresis and determination of interconversion barriers. Wistuba, D., Trapp, O., Gel-Moreto, N., Galensa, R., Schurig, V. Anal. Chem. (2006) [Pubmed]
  23. Suppression of colon carcinogenesis by bioactive compounds in grapefruit. Vanamala, J., Leonardi, T., Patil, B.S., Taddeo, S.S., Murphy, M.E., Pike, L.M., Chapkin, R.S., Lupton, J.R., Turner, N.D. Carcinogenesis (2006) [Pubmed]
  24. CYP1A1 genotype-selective inhibition of benzo[a]pyrene activation by quercetin. Schwarz, D., Kisselev, P., Roots, I. Eur. J. Cancer (2005) [Pubmed]
  25. Variation of flavonoids and furanocoumarins in grapefruit juices: a potential source of variability in grapefruit juice-drug interaction studies. De Castro, W.V., Mertens-Talcott, S., Rubner, A., Butterweck, V., Derendorf, H. J. Agric. Food Chem. (2006) [Pubmed]
  26. Okadaic acid-induced, naringin-sensitive phosphorylation of glycine N-methyltransferase in isolated rat hepatocytes. Møller, M.T., Samari, H.R., Fengsrud, M., Strømhaug, P.E., øStvold, A.C., Seglen, P.O. Biochem. J. (2003) [Pubmed]
  27. Flavonoids promote cell migration in nontumorigenic colon epithelial cells differing in Apc genotype: implications of matrix metalloproteinase activity. Fenton, J.I., Hord, N.G. Nutrition and cancer. (2004) [Pubmed]
  28. Grapefruit juice-felodipine interaction: effect of naringin and 6',7'-dihydroxybergamottin in humans. Bailey, D.G., Kreeft, J.H., Munoz, C., Freeman, D.J., Bend, J.R. Clin. Pharmacol. Ther. (1998) [Pubmed]
  29. 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]
  30. Effect of P-glycoprotein modulators on the pharmacokinetics of camptothecin using microdialysis. Tsai, T.H., Lee, C.H., Yeh, P.H. Br. J. Pharmacol. (2001) [Pubmed]
  31. Inhibition of human breast cancer cell proliferation and delay of mammary tumorigenesis by flavonoids and citrus juices. So, F.V., Guthrie, N., Chambers, A.F., Moussa, M., Carroll, K.K. Nutrition and cancer. (1996) [Pubmed]
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