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Chemical Compound Review

NARIGENIN     5,7-dihydroxy-2-(4- hydroxyphenyl)chroman-4...

Synonyms: naringenin, Naringenine, rac Naringenin, Prestwick_531, CHEMBL32571, ...
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Disease relevance of NSC 11855


Psychiatry related information on NSC 11855


High impact information on NSC 11855


Chemical compound and disease context of NSC 11855


Biological context of NSC 11855


Anatomical context of NSC 11855

  • We conclude that MAPK(erk) signaling in hepatocytes is critical for inhibition of apoB100 secretion by naringenin and insulin [8].
  • Two prenyltransferases, naringenin 8-dimethylallyltransferase and LG 2"-dimethylallyltransferase, were localized in the plastids, whereas 8-dimethylallylnaringenin 2'-hydroxylase, which catalyzes the crucial step in the lavandulyl-group formation, was associated with the endoplasmic reticulum [16].
  • In additional investigations, low concentrations (< 4 mumol/L) of naringenin glucuronides, but neither naringin nor naringenin were found in plasma samples from previous grapefruit juice interaction studies, and metabolization of naringin to naringenin occurred during 24 hours of incubation (37 degrees C) in three of five feces samples tested [2].
  • Furthermore, in McA-RH7777-derived cell lines, naringenin reduced secretion of hapoB72 and hapoB100, which require significant assembly with lipid to be secreted, but did not reduce secretion of hapoB17, hapoB23, and hapoB48, which require only minimal lipidation [17].
  • Inhibition of phenylalanine influx in guinea-pig small intestine by naringenin [proceedings] [18].

Associations of NSC 11855 with other chemical compounds


Gene context of NSC 11855

  • Insulin and naringenin induced PI3K-dependent increases in cytosolic and nuclear SREBP-1 and LDLr expression [1].
  • The increased bioavailability caused by the concomitant intake of grapefruit juice results from the inhibition of intestinal cytochrome P450(CYP)3A4, but not hepatic CYP3A4 or colon CYP3A5, which probably involves the bioflavonoid naringenin and furanocoumarins [23].
  • Secretion of hepatocyte apoB is inhibited by the flavonoids, naringenin and hesperetin, via reduced activity and expression of ACAT2 and MTP [24].
  • Moreover, naringenin selectively inhibited the transcription of Smad3, but not other Smads involved in TGF-beta1 signaling pathways [25].
  • METHODS: In this study, reverse transcription-polymerase chain reaction and Western blot assays were used to investigate the inhibitory effect of naringenin on ECM formation induced by TGF-beta1 in the HSC-T6 cells [25].

Analytical, diagnostic and therapeutic context of NSC 11855


  1. Inhibition of net HepG2 cell apolipoprotein B secretion by the citrus flavonoid naringenin involves activation of phosphatidylinositol 3-kinase, independent of insulin receptor substrate-1 phosphorylation. Borradaile, N.M., de Dreu, L.E., Huff, M.W. Diabetes (2003) [Pubmed]
  2. The fate of naringin in humans: a key to grapefruit juice-drug interactions? Fuhr, U., Kummert, A.L. Clin. Pharmacol. Ther. (1995) [Pubmed]
  3. In vitro inhibition of dihydropyridine oxidation and aflatoxin B1 activation in human liver microsomes by naringenin and other flavonoids. Guengerich, F.P., Kim, D.H. Carcinogenesis (1990) [Pubmed]
  4. Rhizobia catabolize nod gene-inducing flavonoids via C-ring fission mechanisms. Rao, J.R., Cooper, J.E. J. Bacteriol. (1994) [Pubmed]
  5. Multiresistance genes of Rhizobium etli CFN42. González-Pasayo, R., Martínez-Romero, E. Mol. Plant Microbe Interact. (2000) [Pubmed]
  6. Naringenin from Citrus junos has an inhibitory effect on acetylcholinesterase and a mitigating effect on amnesia. Heo, H.J., Kim, M.J., Lee, J.M., Choi, S.J., Cho, H.Y., Hong, B., Kim, H.K., Kim, E., Shin, D.H. Dementia and geriatric cognitive disorders. (2004) [Pubmed]
  7. Phytoestrogens/flavonoids reverse breast cancer resistance protein/ABCG2-mediated multidrug resistance. Imai, Y., Tsukahara, S., Asada, S., Sugimoto, Y. Cancer Res. (2004) [Pubmed]
  8. Inhibition of microsomal triglyceride transfer protein expression and apolipoprotein B100 secretion by the citrus flavonoid naringenin and by insulin involves activation of the mitogen-activated protein kinase pathway in hepatocytes. Allister, E.M., Borradaile, N.M., Edwards, J.Y., Huff, M.W. Diabetes (2005) [Pubmed]
  9. The xylem of rice (Oryza sativa) is colonized by Azorhizobium caulinodans. Gopalaswamy, G., Kannaiyan, S., O'Callaghan, K.J., Davey, M.R., Cocking, E.C. Proc. Biol. Sci. (2000) [Pubmed]
  10. C-ring cleavage of flavonoids by human intestinal bacteria. Winter, J., Moore, L.H., Dowell, V.R., Bokkenheuser, V.D. Appl. Environ. Microbiol. (1989) [Pubmed]
  11. Naringenin: a weakly estrogenic bioflavonoid that exhibits antiestrogenic activity. Ruh, M.F., Zacharewski, T., Connor, K., Howell, J., Chen, I., Safe, S. Biochem. Pharmacol. (1995) [Pubmed]
  12. Naringenin inhibits glucose uptake in MCF-7 breast cancer cells: a mechanism for impaired cellular proliferation. Harmon, A.W., Patel, Y.M. Breast Cancer Res. Treat. (2004) [Pubmed]
  13. Enhancement of transglutaminase activity and polyamine depletion in B16-F10 melanoma cells by flavonoids naringenin and hesperitin correlate to reduction of the in vivo metastatic potential. Lentini, A., Forni, C., Provenzano, B., Beninati, S. Amino Acids (2007) [Pubmed]
  14. Chemical modification of chalcone isomerase by mercurials and tetrathionate. Evidence for a single cysteine residue in the active site. Bednar, R.A., Fried, W.B., Lock, Y.W., Pramanik, B. J. Biol. Chem. (1989) [Pubmed]
  15. Wild type Rhizobium etli, a bean symbiont, produces acetyl-fucosylated, N-methylated, and carbamoylated nodulation factors. Poupot, R., Martinez-Romero, E., Gautier, N., Promé, J.C. J. Biol. Chem. (1995) [Pubmed]
  16. Characterization of leachianone G 2"-dimethylallyltransferase, a novel prenyl side-chain elongation enzyme for the formation of the lavandulyl group of sophoraflavanone G in Sophora flavescens Ait. cell suspension cultures. Zhao, P., Inoue, K., Kouno, I., Yamamoto, H. Plant Physiol. (2003) [Pubmed]
  17. Hepatocyte apoB-containing lipoprotein secretion is decreased by the grapefruit flavonoid, naringenin, via inhibition of MTP-mediated microsomal triglyceride accumulation. Borradaile, N.M., de Dreu, L.E., Barrett, P.H., Behrsin, C.D., Huff, M.W. Biochemistry (2003) [Pubmed]
  18. Inhibition of phenylalanine influx in guinea-pig small intestine by naringenin [proceedings]. Robinson, J.W. J. Physiol. (Lond.) (1979) [Pubmed]
  19. A novel polar surface polysaccharide from Rhizobium leguminosarum binds host plant lectin. Laus, M.C., Logman, T.J., Lamers, G.E., Van Brussel, A.A., Carlson, R.W., Kijne, J.W. Mol. Microbiol. (2006) [Pubmed]
  20. 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]
  21. Modulation of multidrug resistance protein 1 (MRP1/ABCC1) transport and atpase activities by interaction with dietary flavonoids. Leslie, E.M., Mao, Q., Oleschuk, C.J., Deeley, R.G., Cole, S.P. Mol. Pharmacol. (2001) [Pubmed]
  22. Identification of amino acid residues important in the cyclization reactions of chalcone and stilbene synthases. Suh, D.Y., Fukuma, K., Kagami, J., Yamazaki, Y., Shibuya, M., Ebizuka, Y., Sankawa, U. Biochem. J. (2000) [Pubmed]
  23. Effects of food on clinical pharmacokinetics. Singh, B.N. Clinical pharmacokinetics. (1999) [Pubmed]
  24. Secretion of hepatocyte apoB is inhibited by the flavonoids, naringenin and hesperetin, via reduced activity and expression of ACAT2 and MTP. Wilcox, L.J., Borradaile, N.M., de Dreu, L.E., Huff, M.W. J. Lipid Res. (2001) [Pubmed]
  25. Smad3 specific inhibitor, naringenin, decreases the expression of extracellular matrix induced by TGF-beta1 in cultured rat hepatic stellate cells. Liu, X., Wang, W., Hu, H., Tang, N., Zhang, C., Liang, W., Wang, M. Pharm. Res. (2006) [Pubmed]
  26. High-performance liquid chromatographic separation and chiroptical properties of the enantiomers of naringenin and other flavanones. Caccamese, S., Caruso, C., Parrinello, N., Savarino, A. Journal of chromatography. A. (2005) [Pubmed]
  27. Anti-atherogenic effect of citrus flavonoids, naringin and naringenin, associated with hepatic ACAT and aortic VCAM-1 and MCP-1 in high cholesterol-fed rabbits. Lee, C.H., Jeong, T.S., Choi, Y.K., Hyun, B.H., Oh, G.T., Kim, E.H., Kim, J.R., Han, J.I., Bok, S.H. Biochem. Biophys. Res. Commun. (2001) [Pubmed]
  28. Effect of honey on naringin absorption from a decoction of the pericarps of Citrus grandis. Hou, Y.C., Hsiu, S.L., Yen, H.F., Chen, C.C., Chao, P.D. Planta Med. (2000) [Pubmed]
  29. Induction and characterization of a microsomal flavonoid 3'-hydroxylase from parsley cell cultures. Hagmann, M.L., Heller, W., Grisebach, H. Eur. J. Biochem. (1983) [Pubmed]
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