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Chemical Compound Review

Galangin     3,5,7-trihydroxy-2-phenyl- chromen-4-one

Synonyms: Norizalpinin, teptochrysin, PubChem9856, AC1NQYQM, CHEMBL309490, ...
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Disease relevance of TNP00099


High impact information on TNP00099


Chemical compound and disease context of TNP00099


Biological context of TNP00099


Anatomical context of TNP00099

  • Galangin caused a potent, dose-dependent inhibition of CYP1A1 activity, as measured by ethoxyresorufin-O-deethylase activity, in intact cells and in microsomes isolated from DMBA-treated cells [14].
  • CONCLUSIONS: Galangin, at high concentrations, exerts an inhibitory effect on pig bladder smooth muscle contractility through the inhibition of calcium influx and the modulation of intracellular calcium movement [18].
  • We investigated the suppressive effect of galangin on the induction of micronucleated reticulocytes (MNRETs) by mitomycin C (MMC) in mouse peripheral blood [19].
  • When galangin metabolism was examined in fresh plated hepatocytes from six donors, glucuronidation clearly predominated followed by sulfation [20].
  • Galangin, in contrast, did significantly increase the micronucleus frequency in bone marrow and blood erythrocytes under certain conditions, but the largest increases were only between 2 and 3 times control values and these were observed at highly toxic doses [21].

Associations of TNP00099 with other chemical compounds


Gene context of TNP00099

  • Sulfation of galangin by the human liver cytosol, mediated mainly but not exclusively by sulfotransferase (SULT) 1A1, also appeared to be efficient [20].
  • The inhibition by galangin of the methoxyresorufin O-demethylase activity of CYP1A2 was mixed-type, with a Ki value of 0.008 microM [25].
  • Thus, galangin is a potent inhibitor of DMBA metabolism and an agonist/antagonist of the AhR, and may prove to be an effective chemopreventive agent [14].
  • This study for the first time establishes that glucuronidation and sulfation of galangin, and maybe other flavonoids, are more efficient than P450-mediated oxidation, clearly being the metabolic pathways of choice in intact cells and therefore likely also in vivo [20].
  • The tested phenolic compounds significantly decreased the IL-1beta mRNA level and IL-1beta protein concentration (P<0.05) (excluding galangin), iNOS mRNA level and NO production (P<0.001) [26].

Analytical, diagnostic and therapeutic context of TNP00099


  1. Antigenotoxicity of galangin against N-methyl-N-nitrosourea. Sohn, S.J., Huh, I.H., Au, W.W., Heo, M.Y. Mutat. Res. (1998) [Pubmed]
  2. Anticlastogenic effects of galangin against bleomycin-induced chromosomal aberrations in mouse spleen lymphocytes. Heo, M.Y., Lee, S.J., Kwon, C.H., Kim, S.W., Sohn, D.H., Au, W.W. Mutat. Res. (1994) [Pubmed]
  3. Vancomycin resistance reversal in enterococci by flavonoids. Liu, L.X., Durham, D.G., Richards, R.M. J. Pharm. Pharmacol. (2001) [Pubmed]
  4. Galangin expresses bactericidal activity against multiple-resistant bacteria: MRSA, Enterococcus spp. and Pseudomonas aeruginosa. Pepeljnjak, S., Kosalec, I. FEMS Microbiol. Lett. (2004) [Pubmed]
  5. Combinatorial biosynthesis of flavones and flavonols in Escherichia coli. Miyahisa, I., Funa, N., Ohnishi, Y., Martens, S., Moriguchi, T., Horinouchi, S. Appl. Microbiol. Biotechnol. (2006) [Pubmed]
  6. Flavonol-stimulated efflux of 7,12-dimethylbenz(a)anthracene in multidrug-resistant breast cancer cells. Phang, J.M., Poore, C.M., Lopaczynska, J., Yeh, G.C. Cancer Res. (1993) [Pubmed]
  7. The bioflavonoid galangin blocks aryl hydrocarbon receptor activation and polycyclic aromatic hydrocarbon-induced pre-B cell apoptosis. Quadri, S.A., Qadri, A.N., Hahn, M.E., Mann, K.K., Sherr, D.H. Mol. Pharmacol. (2000) [Pubmed]
  8. Interactions of flavonoids and other phytochemicals with adenosine receptors. Ji, X.D., Melman, N., Jacobson, K.A. J. Med. Chem. (1996) [Pubmed]
  9. Structural requirements for the flavonoid-mediated modulation of glutathione S-transferase P1-1 and GS-X pump activity in MCF7 breast cancer cells. van Zanden, J.J., Geraets, L., Wortelboer, H.M., van Bladeren, P.J., Rietjens, I.M., Cnubben, N.H. Biochem. Pharmacol. (2004) [Pubmed]
  10. Effects of flavonoids on glutathione and glutathione-related enzymes in cisplatin-treated L1210 leukemia cells. Cipák, L., Berczeliová, E., Paulíková, H. Neoplasma (2003) [Pubmed]
  11. Galangin protects pig detrusor nerves from repetitive field stimulation and anoxia/glucopenia injury. Dambros, M., de Jongh, R., van Koeveringe, G.A., Bast, A., van Kerrebroeck, P.E. Urology (2005) [Pubmed]
  12. Dietary flavonoids: effects on xenobiotic and carcinogen metabolism. Moon, Y.J., Wang, X., Morris, M.E. Toxicology in vitro : an international journal published in association with BIBRA. (2006) [Pubmed]
  13. Assessment of the antibacterial activity of selected flavonoids and consideration of discrepancies between previous reports. Cushnie, T.P., Hamilton, V.E., Lamb, A.J. Microbiol. Res. (2003) [Pubmed]
  14. The flavonoid galangin is an inhibitor of CYP1A1 activity and an agonist/antagonist of the aryl hydrocarbon receptor. Ciolino, H.P., Yeh, G.C. Br. J. Cancer (1999) [Pubmed]
  15. Flavonoids, potent inhibitors of the human P-form phenolsulfotransferase. Potential role in drug metabolism and chemoprevention. Eaton, E.A., Walle, U.K., Lewis, A.J., Hudson, T., Wilson, A.A., Walle, T. Drug Metab. Dispos. (1996) [Pubmed]
  16. The flavonoid galangin inhibits the L1 metallo-beta-lactamase from Stenotrophomonas maltophilia. Denny, B.J., Lambert, P.A., West, P.W. FEMS Microbiol. Lett. (2002) [Pubmed]
  17. Influence of galangin on HL-60 cell proliferation and survival. Bestwick, C.S., Milne, L. Cancer Lett. (2006) [Pubmed]
  18. Multiple-signaling pathways are involved in the inhibitory effects of galangin on urinary bladder contractility. Dambros, M., de Jongh, R., van Koeveringe, G.A., van Deutekom, M., De Mey, J.G., Palma, P.C., van Kerrebroeck, P.E. Neurourology and urodynamics. (2005) [Pubmed]
  19. Anticlastogenic effects of galangin against mitomycin C-induced micronuclei in reticulocytes of mice. Heo, M.Y., Jae, L.H., Jung, S.S., Au, W.W. Mutat. Res. (1996) [Pubmed]
  20. Glucuronidation versus oxidation of the flavonoid galangin by human liver microsomes and hepatocytes. Otake, Y., Hsieh, F., Walle, T. Drug Metab. Dispos. (2002) [Pubmed]
  21. In vivo exposure to plant flavonols. Influence on frequencies of micronuclei in mouse erythrocytes and sister-chromatid exchange in rabbit lymphocytes. MacGregor, J.T., Wehr, C.M., Manners, G.D., Jurd, L., Minkler, J.L., Carrano, A.V. Mutat. Res. (1983) [Pubmed]
  22. Interaction of organotins with a vacuolar-type H(+)-ATPase. Apps, D.K., Webster, L.C. Biochem. Biophys. Res. Commun. (1996) [Pubmed]
  23. Biochemical studies of a new class of alcohol dehydrogenase inhibitors from Radix puerariae. Keung, W.M. Alcohol. Clin. Exp. Res. (1993) [Pubmed]
  24. Inhibition of rat vas deferens contractions by flavonoids in-vitro. Capasso, R., Fiorino, F., Ascione, V., Frecentese, F., Borrelli, F. J. Pharm. Pharmacol. (2006) [Pubmed]
  25. Comparative inhibition of human cytochromes P450 1A1 and 1A2 by flavonoids. Zhai, S., Dai, R., Friedman, F.K., Vestal, R.E. Drug Metab. Dispos. (1998) [Pubmed]
  26. Effects of ethanol extract of propolis (EEP) and its flavones on inducible gene expression in J774A.1 macrophages. Blonska, M., Bronikowska, J., Pietsz, G., Czuba, Z.P., Scheller, S., Krol, W. Journal of ethnopharmacology. (2004) [Pubmed]
  27. Anti-genotoxicity of galangin as a cancer chemopreventive agent candidate. Heo, M.Y., Sohn, S.J., Au, W.W. Mutat. Res. (2001) [Pubmed]
  28. In vitro activity of propolis against Streptococcus pyogenes. Bosio, K., Avanzini, C., D'Avolio, A., Ozino, O., Savoia, D. Lett. Appl. Microbiol. (2000) [Pubmed]
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